DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application is being examined under the pre-AIA first to invent provisions.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 22 Sep. 2025 has been entered.
EXAMINER'S AMENDMENT
An examiner’s amendment to the record appears below. Should the changes and/or additions be unacceptable to applicant, an amendment may be filed as provided by 37 CFR 1.312. To ensure consideration of such an amendment, it MUST be submitted no later than the payment of the issue fee.
The application has been amended as follows:
[[11.]]1. (Withdrawn) A process of purifying 1,4-butanediol (1,4-BDO) comprising: (a) subjecting a crude 1,4-BDO mixture to a first column distillation procedure to remove materials with a boiling point lower than 1,4-BDO from the crude 1,4-BDO mixture to produce a first 1,4-BDO-containing product stream; and (b) subjecting the first 1,4-BDO-containing product stream to a second column distillation procedure to remove materials with boiling points higher than 1,4-BDO as a first high-boilers stream, to produce a purified 1,4-BDO product, wherein the purified 1,4-BDO product is collected from a side-draw of the second column distillation procedure.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 42 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Regarding claim 42, claim 17 recites “a crude bioderived 1,4-BDO mixture comprising a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water” and claim 42 recites “wherein the crude 1,4-BDO mixture is at least 50% (w/w), 60% (w/w), 70% (w/w), 80% (w/w), 85% (w/w) or 90% (w/w) 1,4-BDO”. The ranges in claim 42 encompass the entire ranges of claim 17 and thus does not further limit claim 17.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 17, 22, 40-44, 46-49, and 51-53 are rejected under 35 U.S.C. 103 as being unpatentable over Izawa et al. WO 2013/008686 published 17 Jan. 2013 and filed Jul. 3 2012 as translated by US 2014/0187740) and further in view of Van Dien et al. US 2012/0225463 (hereafter Dien), Okuyama US 5,981,810 (hereafter Okuyama), Cvengros et al. “Evaporator with wiped film as the reboiler of the vacuum rectifying column” Separation and Purification Technology 15 (1999) 95-100 published in 1999 (hereafter Cvengros), Ernst et al. US 4,383,895 (hereafter Ernst), and Clark et al. US 2011/0003355 (hereafter Clark).
Regarding claim 17, Izawa teaches a system for purifying (distillation, ¶26) bioderived 1,4-BDO (fermentation of 1,4BG, ¶24) comprising a first distillation column (¶26).
Izawa does not teach
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material;
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO;
a first distillation column receiving a crude bioderived 1,4-BDO mixture comprising a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth and generating a first stream of materials with boiling points lower than 1,4-BDO and a first bioderived 1,4-BDOcontaining product stream;
a first intermediate distillation column receiving the bioderived 1,4-BDO-containing product stream at a feed point and generating a first stream of materials with boiling points higher than 1,4-BDO, and a second bioderived 1,4-BDO-containing product stream; further comprising a hydrogenation reactor constructed to treat the second bioderived 1,4-BDOcontaining product stream generated by the first intermediate distillation column;
a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the first intermediate distillation column;
a second intermediate distillation column receiving the second bioderived 1,4-BDOcontaining product stream and generating a second stream of materials with boiling points lower than 1,4-BDO and a third bioderived 1,4-BDO-containing product stream; and
a second distillation column receiving the third bioderived 1,4-BDO-containing product stream at a feed point and generating a third stream of materials with boiling points lower than 1,4-BDO, and a purified bioderived 1,4-BDO product.
Dien teaches a system for purifying bioderived 1,4-BDO comprising a filtration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶206, ¶212 including ultrafiltration).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the purification (¶26) of Izawa by incorporating the microfiltration (¶206, ¶212 including ultrafiltration) in order to separate the product form other components in the culture (¶206, ¶212).
Clark teaches a system (Fig 16) for purifying (¶132) bioderived (fermentation in Fig 16) 1,4-BDO (¶132) comprising
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶132 where the filtration includes centrifugation; and/or ultrafiltration ¶134; where microfiltration is used to reduce membrane fouling as taught in ¶69, ¶75);
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO (¶134-135);
a first distillation column (Distillation #1); and
a second distillation column (Distillation #2).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the purification (¶26) of Izawa by incorporating the microfiltration (¶132-135; ¶69, ¶75) and nanofiltration (¶134-135) in order to separate the product form other components in the culture (¶132-135, such as solids and salts) and reduce membrane fouling (¶69, ¶75).
Okuyama teaches a system (Fig 2) for purifying 1,4-BDO (Okuyama: abstract) comprising:
a first distillation column (202 in Fig 2) receiving a crude 1,4-BDO mixture (from reactor 201) and generating a first stream (column 202 distillate) of materials with boiling points lower (low-boiling point substances shown in Fig 2) than 1,4-BDO and a first bioderived 1,4-BDO-containing product stream (column 202 bottoms which goes to tower 203);
a first intermediate distillation column (203) receiving the bioderived 1,4-BDOcontaining product stream at a feed point (feed point shown in Fig 2) and generating a first stream (column 203 bottoms going to tower 204) of materials with boiling points higher than 1,4-BDO, and a second bioderived 1,4-BDO-containing product stream (crude 1,4-butanediol from tower 203 to reactor 205); further comprising a hydrogenation reactor (205) constructed to treat the second bioderived 1,4-BDOcontaining product stream generated by the first intermediate distillation column (col 2 lines 1-14);
a separator/reboiler (204) receiving the first stream of materials with boiling points higher than 1,4-BDO (as shown in Fig 2) and generating a distillate (column 204 distillate to be mixed with the column 202 bottoms), wherein the distillate is fed to the first intermediate distillation column;
a second intermediate distillation column (208) receiving (via reactors 205/206 and separator 207) the second bioderived 1,4-BDO containing product stream and generating a third bioderived 1,4-BDO-containing product stream (stream transferred from column 208 to column 209); and
a second distillation column (209) receiving the third bioderived 1,4-BDO-containing product stream at a feed point (feed point shown in Fig 2) and generating a third stream of materials with boiling points lower than 1,4-BDO (column 209 distillate), and a purified bioderived 1,4-BDO product (column 209 1,4-butanediol).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the first distillation column (202 in Fig 2), second distillation column (203 in Fig 2), separator (Okuyama: 204 in Fig 2), and hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14).
Regarding wherein the 1,4-BDO is bioderived 1,4-BDO, the limitation is a method of using the apparatus. See MPEP §2114, §2115, §2173.05(g). One of ordinary skill in the art would have recognized that bioderived 1,4-BDO would be fully capable of being purified in the Okuyama system.
Cvengros teaches where distillation columns (Cvengros: page 95 col 2 lines 1-8) may employ wiped-film evaporation as a reboiler in order to concentrate the distillate (Cvengros: page 96 lines 30-47) minimize residence time (Cvengros: page 96 col 1 lines1-17) and reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24). The reboiler return the vapor from the reboiler to the distillation column (Cvengros: where the tube 7 in Fig 1 is both a reflux inlet and a vapor outlet).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the separator/reboiler of the Okuyama (204 in Fig 2) and Izawa combination by incorporating the wiped film evaporator of Cvengros (as shown above) in order to reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24; Ernst: col 2 lines 14-23) and concentrate the distillate (Cvengros: page 96 lines 30-47; Ernst: col 2 lines 23-27). The combination would result in a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the first intermediate distillation column.
Regarding wherein the second intermediate distillation column generates a second stream of materials with boiling points lower than 1,4-BDO, Okuyama teaches where the unpurified 1,4-BDO mixture contains lower and higher boiling point components (col 9 lines 34-35) and where a distillation column is known to separate a target from lower and higher boiling point components (see distillation columns 203, 204, and 209 in Fig 2). Okuyama does not teach streams from the second intermediate distillation column which are not the third bioderived 1,4-BDO-containing product stream.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the second intermediate distillation column of Okuyama (208) by incorporating a second stream of materials with boiling points lower than 1,4-BDO (column 208 distillate) in order to separate the 1,4-BDO from materials with boiling points lower than 1,4-BDO (col 9 lines 34-35, Fig 2).
MPEP §2115 recites ““[A]pparatus claims cover what a device is, not what a device does.” Hewlett-Packard Co.v.Bausch & Lomb Inc., 909 F.2d 1464, 1469, 15 USPQ2d 1525, 1528 (Fed. Cir. 1990) (emphasis in original). A claim containing a “recitation with respect to the manner in which a claimed apparatus is intended to be employed does not differentiate the claimed apparatus from a prior art apparatus” if the prior art apparatus teaches all the structural limitations of the claim. Ex parte Masham, 2 USPQ2d 1647 (Bd. Pat. App. & Inter. 1987) (The preamble of claim 1 recited that the apparatus was “for mixing flowing developer material” and the body of the claim recited “means for mixing ..., said mixing means being stationary and completely submerged in the developer material.” The claim was rejected over a reference which taught all the structural limitations of the claim for the intended use of mixing flowing developer. However, the mixer was only partially submerged in the developer material. The Board held that the amount of submersion is immaterial to the structure of the mixer and thus the claim was properly rejected.).” MPEP §2115 recites “Thus, “[i]nclusion of the material or article worked upon by a structure being claimed does not impart patentability to the claims.” In re Otto, 312 F.2d 937, 136 USPQ 458, 459 (CCPA 1963); see also In re Young, 75 F.2d 996, 25 USPQ 69 (CCPA 1935).” It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to input bioderived 1,4-BDO into the distillation tower 202 in order to purify bioderived 1,4-BDO, where the structure of the of the distillation system of Izawa/Dien/Okuyama/Cvengros would be fully capable of distilling the bioderived 1,4-BDO from the impurities.
Wherein the crude 1,4-BDO mixture comprises a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 17. See MPEP §2114, §2115, §2173.05(g). Izawa further teaches where the 1,4-BDO can be obtained by fermentation (¶24), where such a crude mixture would be within the expected bounds of a fermentation crude.
Regarding claim 22, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the second distillation column (Okuyama 209) further comprises a side draw (Okuyama where Fig 2 shows the 1,4-BDO stream as a side drawn from the column).
Regarding claim 40, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the crude 1,4-BDO mixture comprises 1,4-BDO and water (Okuyama col 2 lines 1-14) and the purified 1,4-BDO product is greater than 98% (w/w) 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the crude 1,4-BDO mixture comprises 80% to 85% 1,4-BDO with 1% to 25% water; recovery of the purified 1,4-BDO product from the crude 1,4-BDO mixture is greater than 98%; and the purified 1,4-BDO product is greater than 98% (w/w) 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 40. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 41, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the first distillation column (Okuyama 202) removes water (Okuyama col 2 lines 1-14).
Wherein the first distillation column removes water to below 0.5% is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 41. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 42, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the crude 1,4-BDO mixture allows high purity 1,4-BDO (Okuyama col 2 lines 53-57).
Wherein the crude 1,4-BDO mixture is at least 50% (w/w), 60% (w/w), 70% (w/w), 80% (w/w), 85% (w/w) or 90% (w/w) 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 42. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 43, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the purified 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the purified 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 43. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 44, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17.
Wherein recovery of 1,4-BDO in the purified 1,4-BDO product from the crude 1,4-BDO mixture is greater than 40%, 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98% or 99% is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 44. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 46, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17.
Wherein the first distillation column and the second distillation column comprise pressures equal to or less than atmospheric pressure is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 41. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 47, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 46.
Wherein the pressure of the first distillation column differs from the pressure of the second distillation column is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 47. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 48, Izawa teaches a system for purifying (distillation, ¶26) bioderived 1,4-BDO (fermentation of 1,4BG, ¶24) comprising a first distillation column (¶26).
Izawa does not teach
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material;
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO;
a first distillation column receiving a crude bioderived 1,4-BDO mixture comprising a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth, and generating a first stream of materials with boiling points lower than 1,4-BDO and a first bioderived 1,4-BDO-containing product stream;
an intermediate distillation column receiving the first bioderived 1,4-BDO-containing product stream generating a first stream of materials with boiling points higher than 1,4-BDO, and a second bioderived 1, 4-BDO-containing product stream;
a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the intermediate distillation column; and
a second distillation column receiving the second bioderived 1,4-BDO-containing product stream at a feed point and generating a second stream of materials with boiling points lower than 1,4-BDO, a second stream of materials with boiling points higher than 1,4-BDO, and a purified bioderived 1,4-BDO product from a side-draw.
Dien teaches a system for purifying bioderived 1,4-BDO comprising a filtration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶206, ¶212 including ultrafiltration).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the fermentation (¶24)/distillation (¶26) of Izawa by incorporating the filtration unit of Dien in order to filter the broth (¶206, ¶212 including ultrafiltration).
Clark teaches a system (Fig 16) for purifying (¶132) bioderived (fermentation in Fig 16) 1,4-BDO (¶132) comprising
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶132 where the filtration includes centrifugation; and/or ultrafiltration ¶134; where microfiltration is used to reduce membrane fouling as taught in ¶69, ¶75);
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO (¶134-135);
a first distillation column (Distillation #1); and
a second distillation column (Distillation #2).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the purification (¶26) of Izawa by incorporating the microfiltration (¶132-135) and nanofiltration (¶134-135) in order to separate the product form other components in the culture (¶132-135, such as solids and salts) and reduce membrane fouling (¶69, ¶75).
Okuyama teaches a system (Fig 2) for purifying 1,4-BDO (Okuyama: abstract) comprising:
a first distillation column (202) receiving a crude 1,4-BDO mixture (from reactor 201) generating a first stream (column 202 distillate) of materials with boiling points lower than 1,4-BDO and a first 1,4-BDO-containing product stream (column 202 bottoms);
an intermediate distillation column (203) receiving the first 1,4-BDO-containing product stream generating a first stream (column 203 bottoms going to tower 204) of materials with boiling points higher than 1,4-BDO, and a second 1, 4- BDO-containing product stream (crude 1,4-butanediol from tower 203 to reactor 205);
a separator/reboiler (204) receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate (column 204 distillate to be mixed with the column 202 bottoms), wherein the distillate is fed to the intermediate distillation column; and
a second distillation column (209) receiving the second 1,4-BDO-containing product stream at a feed point (feed point shown in Fig 2) and generating a second stream (low-boiling point substances in Fig 2) of materials with boiling points lower than 1,4- BDO, a second stream (column 209 bottoms) of materials with boiling points higher than 1,4-BDO, and a purified 1,4- BDO product (column 209 1,4-butanediol) from a side-draw (where Fig 2 shows the product from a side draw).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the first distillation column (202 in Fig 2), second distillation column (203 in Fig 2), separator (Okuyama: 204 in Fig 2), and hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14).
Regarding wherein the 1,4-BDO is bioderived 1,4-BDO, the limitation is a method of using the apparatus. See MPEP §2114, §2115, §2173.05(g). One of ordinary skill in the art would have recognized that bioderived 1,4-BDO would be fully capable of being purified in the Okuyama system.
Cvengros teaches where distillation columns (Cvengros: page 95 col 2 lines 1-8) may employ wiped-film evaporation as a reboiler in order to concentrate the distillate (Cvengros: page 96 lines 30-47) minimize residence time (Cvengros: page 96 col 1 lines1-17) and reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24). The reboiler return the vapor from the reboiler to the distillation column (Cvengros: where the tube 7 in Fig 1 is both a reflux inlet and a vapor outlet).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the separator/reboiler of Okuyama (204 in Fig 2) by incorporating the wiped film evaporator of Cvengros (as shown above) in order to reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24; Ernst: col 2 lines 14-23) and concentrate the distillate (Cvengros: page 96 lines 30-47; Ernst: col 2 lines 23-27). The combination would result in a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the intermediate distillation column.
Wherein the crude 1,4-BDO mixture comprises a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 48. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 49, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 48.
Izawa does not teach a hydrogenation reactor constructed to treat the second 1,4-BDO-containing product stream prior to the second 1,4-BDO-containing product stream being received by the second distillation column.
Okuyama teaches a hydrogenation reactor (205) constructed to treat the second 1,4-BDO-containing product stream prior to the second 1,4-BDO-containing product stream being received by the second distillation column (as shown in Fig 2 where the stream passes through the reactor after the intermediate distillation column 203 and before the second distillation column 209).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14). Izawa further teaches where the 1,4-BDO can be obtained by fermentation (¶24), where such a crude mixture would be within the expected bounds of a fermentation crude.
Regarding claim 51, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 48. The claim 48 modification further teaches wherein the purified bioderived 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the purified bioderived 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 51. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 52, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 17.
Wherein the purified bioderived 1,4-BDO product has no or less than 0.01 percent 2-methyl-3-buten-l-ol, and/or no or less than 0.01 percent 1,6-hexanediol, and/or less than 0.04 percent butanoic acid, propyl ester and/or less than 0.04 percent 2-( 4-hydroxybutoxy) tetrahydrofuran is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 52. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 53, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 48.
Wherein the purified bioderived 1,4-BDO product has no or less than 0.01 percent 2-methyl-3-buten-l-ol, and/or no or less than 0.01 percent 1,6-hexanediol, and/or less than 0.04 percent butanoic acid, propyl ester and/or less than 0.04 percent 2-( 4-hydroxybutoxy) tetrahydrofuran is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 53. See MPEP §2114, §2115, §2173.05(g).
Claim 45 is rejected under 35 U.S.C. 103 as being unpatentable over Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst as applied to claim 22 above, and further in view of Buckley et al. “Design of distillation column control systems” ISBN 0-71313551-4 published 1985 (hereafter Buckley).
Regarding claim 45, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 22.
Izawa does not teach wherein the purified 1,4-BDO product collected from the side draw is in a vapor phase.
Buckley teaches column design wherein the side-draw is located below the feed point of a distillation column in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
It would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the location of the side draw of Okuyama (as shown above) by collecting the side draw as a vapor in order to minimize high boilers (Buckley: page 169).
Claim 50 is rejected under 35 U.S.C. 103 as being unpatentable over Izawa in view of Dien, Cvengros, Okuyama, Clark, and Ernst as applied to claim 48 above, and further in view of Buckley et al. “Design of distillation column control systems” ISBN 0-71313551-4 published 1985 (hereafter Buckley).
Regarding claim 50, Izawa in view of Dien, Okuyama, Cvengros, Clark, and Ernst teaches all the limitations of claim 48.
Izawa does not teach wherein the side-draw is located below the feed point of the second distillation column.
Buckley teaches column design wherein the side-draw is located below the feed point of a distillation column in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
It would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the location of the side draw of Okuyama (as shown above) by locating the side draw below the feed point in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
Claims 17, 22, 40-44, 46-49, and 51-53 are rejected under 35 U.S.C. 103 as being unpatentable over Clark et al. US 2011/0003355 (hereafter Clark) and further in view of Okuyama US 5,981,810 (hereafter Okuyama), Cvengros et al. “Evaporator with wiped film as the reboiler of the vacuum rectifying column” Separation and Purification Technology 15 (1999) 95-100 published in 1999 (hereafter Cvengros), and Ernst et al. US 4,383,895 (hereafter Ernst).
Regarding claims 17, Clark teaches a system (Fig 16) for purifying (¶132) bioderived (fermentation in Fig 16) 1,4-BDO (¶132) comprising
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶132 where the filtration includes centrifugation; and/or ultrafiltration ¶134; where microfiltration is used to reduce membrane fouling as taught in ¶69, ¶75).
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO (¶134-135);
a first distillation column (Distillation #1); and
a second distillation column (Distillation #2).
Clark does not teach
a first distillation column receiving a crude bioderived 1,4-BDO mixture comprising a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth and generating a first stream of materials with boiling points lower than 1,4-BDO and a first bioderived 1,4-BDOcontaining product stream;
a first intermediate distillation column receiving the bioderived 1,4-BDO-containing product stream at a feed point and generating a first stream of materials with boiling points higher than 1,4-BDO, and a second bioderived 1,4-BDO-containing product stream; further comprising a hydrogenation reactor constructed to treat the second bioderived 1,4-BDOcontaining product stream generated by the first intermediate distillation column;
a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the first intermediate distillation column;
a second intermediate distillation column receiving the second bioderived 1,4-BDOcontaining product stream and generating a second stream of materials with boiling points lower than 1,4-BDO and a third bioderived 1,4-BDO-containing product stream; and
a second distillation column receiving the third bioderived 1,4-BDO-containing product stream at a feed point and generating a third stream of materials with boiling points lower than 1,4-BDO, and a purified bioderived 1,4-BDO product.
Okuyama teaches a system (Fig 2) for purifying 1,4-BDO (Okuyama: abstract) comprising:
a first distillation column (202) receiving a crude 1,4-BDO mixture (from reactor 201) and generating a first stream (column 202 distillate) of materials with boiling points lower than 1,4-BDO and a first bioderived 1,4-BDO-containing product stream (column 202 bottoms);
a first intermediate distillation column (203) receiving the bioderived 1,4-BDOcontaining product stream at a feed point (feed point shown in Fig 2) and generating a first stream (column 203 bottoms going to tower 204) of materials with boiling points higher than 1,4-BDO, and a second bioderived 1,4-BDO-containing product stream (crude 1,4-butanediol from tower 203 to reactor 205); further comprising a hydrogenation reactor (205) constructed to treat the second bioderived 1,4-BDOcontaining product stream generated by the first intermediate distillation column (col 2 lines 1-14);
a separator/reboiler (204) receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate (column 204 distillate to be mixed with the column 202 bottoms), wherein the distillate is fed to the first intermediate distillation column;
a second intermediate distillation column (208) receiving (via reactors 205/206 and separator 207) the second bioderived 1,4-BDO containing product stream and generating a third bioderived 1,4-BDO-containing product stream (stream transferred from column 208 to column 209); and
a second distillation column (209) receiving the third bioderived 1,4-BDO-containing product stream at a feed point (feed point shown in Fig 2) and generating a third stream of materials with boiling points lower than 1,4-BDO (column 209 distillate), and a purified bioderived 1,4-BDO product (column 209 1,4-butanediol).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the first distillation column (202 in Fig 2), second distillation column (203 in Fig 2), separator (Okuyama: 204 in Fig 2), and hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14).
Regarding wherein the 1,4-BDO is bioderived 1,4-BDO, the limitation is a method of using the apparatus. See MPEP §2114, §2115, §2173.05(g). One of ordinary skill in the art would have recognized that bioderived 1,4-BDO would be fully capable of being purified in the Okuyama system.
Cvengros teaches where distillation columns (Cvengros: page 95 col 2 lines 1-8) may employ wiped-film evaporation as a reboiler in order to concentrate the distillate (Cvengros: page 96 lines 30-47) minimize residence time (Cvengros: page 96 col 1 lines1-17) and reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24). The reboiler return the vapor from the reboiler to the distillation column (Cvengros: where the tube 7 in Fig 1 is both a reflux inlet and a vapor outlet).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the separator/reboiler of the Okuyama (204 in Fig 2) and Izawa combination by incorporating the wiped film evaporator of Cvengros (as shown above) in order to reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24; Ernst: col 2 lines 14-23) and concentrate the distillate (Cvengros: page 96 lines 30-47; Ernst: col 2 lines 23-27). The combination would result in a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the first intermediate distillation column.
Regarding wherein the second intermediate distillation column generates a second stream of materials with boiling points lower than 1,4-BDO, Okuyama teaches where the unpurified 1,4-BDO mixture contains lower and higher boiling point components (col 9 lines 34-35) and where a distillation column is known to separate a target from lower and higher boiling point components (see distillation columns 203, 204, and 209 in Fig 2). Okuyama does not teach streams from the second intermediate distillation column which are not the third bioderived 1,4-BDO-containing product stream.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the second intermediate distillation column of Okuyama (208) by incorporating a second stream of materials with boiling points lower than 1,4-BDO (column 208 distillate) in order to separate the 1,4-BDO from materials with boiling points lower than 1,4-BDO (col 9 lines 34-35, Fig 2).
Wherein the crude 1,4-BDO mixture comprises a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 17. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 22, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the second distillation column (Okuyama 209) further comprises a side draw (Okuyama where Fig 2 shows the 1,4-BDO stream as a side drawn from the column).
Regarding claim 40, Clark in view of Okuyama, Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the crude 1,4-BDO mixture comprises 1,4-BDO and water (Okuyama col 2 lines 1-14) and the purified 1,4-BDO product is greater than 98% (w/w) 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the crude 1,4-BDO mixture comprises 80% to 85% 1,4-BDO with 1% to 25% water; recovery of the purified 1,4-BDO product from the crude 1,4-BDO mixture is greater than 98%; and the purified 1,4-BDO product is greater than 98% (w/w) 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 40. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 41, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the first distillation column (Okuyama 202) removes water (Okuyama col 2 lines 1-14).
Wherein the first distillation column removes water to below 0.5% is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 41. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 42, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the crude 1,4-BDO mixture allows high purity 1,4-BDO (Okuyama col 2 lines 53-57).
Wherein the crude 1,4-BDO mixture is at least 50% (w/w), 60% (w/w), 70% (w/w), 80% (w/w), 85% (w/w) or 90% (w/w) 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 42. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 43, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17. The claim 17 modification further teaches wherein the purified 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the purified 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 43. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 44, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17.
Wherein recovery of 1,4-BDO in the purified 1,4-BDO product from the crude 1,4-BDO mixture is greater than 40%, 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98% or 99% is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 44. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 46, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17.
Wherein the first distillation column and the second distillation column comprise pressures equal to or less than atmospheric pressure is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 41. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 47, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 46.
Wherein the pressure of the first distillation column differs from the pressure of the second distillation column is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 47. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 48, Clark teaches a system (Fig 16) for purifying (¶132) bioderived (fermentation in Fig 16) 1,4-BDO (¶132) comprising
a microfiltration unit that achieves removal of cellular material from fermentation broth comprising bioderived 1,4-BDO and cellular material (¶132 where the filtration includes centrifugation; and/or ultrafiltration ¶134; where microfiltration is used to reduce membrane fouling as taught in ¶69, ¶75);
a nanofiltration unit that achieves: separation of salts, removal of color, desalination, and/or removal of retentate from said fermentation broth comprising said bioderived 1,4-BDO (¶134-135);
a first distillation column (Distillation #1); and
a second distillation column (Distillation #2).
Clark does not teach
a first distillation column receiving a crude bioderived 1,4-BDO mixture comprising a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth, and generating a first stream of materials with boiling points lower than 1,4-BDO and a first bioderived 1,4-BDO-containing product stream;
an intermediate distillation column receiving the first bioderived 1,4-BDO-containing product stream generating a first stream of materials with boiling points higher than 1,4-BDO, and a second bioderived 1, 4-BDO-containing product stream;
a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the intermediate distillation column; and
a second distillation column receiving the second bioderived 1,4-BDO-containing product stream at a feed point and generating a second stream of materials with boiling points lower than 1,4-BDO, a second stream of materials with boiling points higher than 1,4-BDO, and a purified bioderived 1,4-BDO product from a side-draw.
Okuyama teaches a system (Fig 2) for purifying 1,4-BDO (Okuyama: abstract) comprising:
a first distillation column (202) receiving a crude 1,4-BDO mixture (from reactor 201) generating a first stream (column 202 distillate) of materials with boiling points lower than 1,4-BDO and a first 1,4-BDO-containing product stream (column 202 bottoms);
an intermediate distillation column (203) receiving the first 1,4-BDO-containing product stream generating a first stream (column 203 bottoms going to tower 204) of materials with boiling points higher than 1,4-BDO, and a second 1, 4- BDO-containing product stream (crude 1,4-butanediol from tower 203 to reactor 205);
a separator/reboiler (204) receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate (column 204 distillate to be mixed with the column 202 bottoms), wherein the distillate is fed to the intermediate distillation column; and
a second distillation column (209) receiving the second 1,4-BDO-containing product stream at a feed point (feed point shown in Fig 2) and generating a second stream (low-boiling point substances in Fig 2) of materials with boiling points lower than 1,4- BDO, a second stream (column 209 bottoms) of materials with boiling points higher than 1,4-BDO, and a purified 1,4- BDO product (column 209 1,4-butanediol) from a side-draw (where Fig 2 shows the product from a side draw).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the first distillation column (202 in Fig 2), second distillation column (203 in Fig 2), separator (Okuyama: 204 in Fig 2), and hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14).
Regarding wherein the 1,4-BDO is bioderived 1,4-BDO, the limitation is a method of using the apparatus. See MPEP §2114, §2115, §2173.05(g). One of ordinary skill in the art would have recognized that bioderived 1,4-BDO would be fully capable of being purified in the Okuyama system.
Cvengros teaches where distillation columns (Cvengros: page 95 col 2 lines 1-8) may employ wiped-film evaporation as a reboiler in order to concentrate the distillate (Cvengros: page 96 lines 30-47) minimize residence time (Cvengros: page 96 col 1 lines1-17) and reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24). The reboiler return the vapor from the reboiler to the distillation column (Cvengros: where the tube 7 in Fig 1 is both a reflux inlet and a vapor outlet).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the separator/reboiler of Okuyama (204 in Fig 2) by incorporating the wiped film evaporator of Cvengros (as shown above) in order to reduce thermal degredation (Cvengros: page 95 col 2 lines 18-24; Ernst: col 2 lines 14-23) and concentrate the distillate (Cvengros: page 96 lines 30-47; Ernst: col 2 lines 23-27). The combination would result in a wiped-film evaporator receiving the first stream of materials with boiling points higher than 1,4-BDO and generating a distillate, wherein the distillate is fed to the intermediate distillation column.
Wherein the crude 1,4-BDO mixture comprises a mixture of 1,4-BDO that is about 50% to 90% 1,4-BDO and 50% to 1 % water with one more other impurities that are derived from the fermentation broth is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 48. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 49, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 48.
Clark does not teach a hydrogenation reactor constructed to treat the second 1,4-BDO-containing product stream prior to the second 1,4-BDO-containing product stream being received by the second distillation column.
Okuyama teaches a hydrogenation reactor (205) constructed to treat the second 1,4-BDO-containing product stream prior to the second 1,4-BDO-containing product stream being received by the second distillation column (as shown in Fig 2 where the stream passes through the reactor after the intermediate distillation column 203 and before the second distillation column 209).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the distillation (¶26) of Izawa by incorporating the hydrogenation reactor (Okuyama: 205 in Fig 2) of Okuyama in order to purify the product (Izawa ¶26, Okuyama col 2 lines 1-14).
Regarding claim 51, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 48. The claim 48 modification further teaches wherein the purified bioderived 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO (Okuyama col 12 lines 50-56).
Wherein the purified bioderived 1,4-BDO product is greater than 90% (w/w), 91 % (w/w), 92% (w/w), 93% (w/w), 94% (w/w), 95% (w/w), 96% (w/w), 97%, (w/w) 98% (w/w), 99% (w/w), 99.1 % (w/w), 99.2% (w/w), 99.3% (w/w), 99.4% (w/w), 99.5% (w/w), 99.6% (w/w), 99.7% (w/w), 99.8% (w/w) or 99.9% (w/w), 1,4-BDO is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 51. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 52, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 17.
Wherein the purified bioderived 1,4-BDO product has no or less than 0.01 percent 2-methyl-3-buten-l-ol, and/or no or less than 0.01 percent 1,6-hexanediol, and/or less than 0.04 percent butanoic acid, propyl ester and/or less than 0.04 percent 2-( 4-hydroxybutoxy) tetrahydrofuran is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 52. See MPEP §2114, §2115, §2173.05(g).
Regarding claim 53, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 48.
Wherein the purified bioderived 1,4-BDO product has no or less than 0.01 percent 2-methyl-3-buten-l-ol, and/or no or less than 0.01 percent 1,6-hexanediol, and/or less than 0.04 percent butanoic acid, propyl ester and/or less than 0.04 percent 2-( 4-hydroxybutoxy) tetrahydrofuran is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 53. See MPEP §2114, §2115, §2173.05(g).
Claim 45 is rejected under 35 U.S.C. 103 as being unpatentable over Clark in view of Okuyama, Cvengros, and Ernst as applied to claim 22 above, and further in view of Buckley et al. “Design of distillation column control systems” ISBN 0-71313551-4 published 1985 (hereafter Buckley).
Regarding claim 45, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 22.
Clark does not teach wherein the purified 1,4-BDO product collected from the side draw is in a vapor phase.
Buckley teaches column design wherein the side-draw is located below the feed point of a distillation column in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
It would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the location of the side draw of Okuyama (as shown above) by collecting the side draw as a vapor in order to minimize high boilers (Buckley: page 169).
Claim 50 is rejected under 35 U.S.C. 103 as being unpatentable over Clark in view of Okuyama, Cvengros, and Ernst as applied to claim 48 above, and further in view of Buckley et al. “Design of distillation column control systems” ISBN 0-71313551-4 published 1985 (hereafter Buckley).
Regarding claim 50, Clark in view of Okuyama, Cvengros, and Ernst teaches all the limitations of claim 48.
Clark does not teach wherein the side-draw is located below the feed point of the second distillation column.
Buckley teaches column design wherein the side-draw is located below the feed point of a distillation column in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
It would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the location of the side draw of Okuyama (as shown above) by locating the side draw below the feed point in order to take the product as a vapor and minimize high boilers (Buckley: page 169).
Response to Arguments
The following is a response to Applicant’s arguments filed 22 Sep. 2025:
In order to expedite prosecution, Examiner has amended claim 1 to recite “1.” rather than “11.” See MPEP 714.
Applicant argues that the cited prior does not teach or make obvious the claimed invention.
Examiner disagrees.
Regarding the Iwaza requires a concentration of 1,4-BDO of 99.00% or more (¶14) in contrast to the pending claims, the concentration of Iwaza is a final concentration and does not render nonobvious a crude 1,4-BDO of between 50-90%.
Regarding that Okuyama teaches a cruse that has impurities of 1% or more with at least one of a list of compounds (col 3), the teaching includes at least 10% impurities (where the range of 10% impurities is within the taught range of at least 1% impurities. Further, that water is not in the specific list cited by Applicant does not render the claimed invention nonobvious. One of ordinary skill would expect there to be impurities other than the 12 listed. For instance, Okuyama teaches in col 9 where water can be separated from the mixture in the distillation column.
Further, the claim limitation is a method of using the apparatus and the material worked upon by the apparatus. Because the prior art teaches the structure of the claimed invention, one of ordinary skill in the art would know that the prior art would be fully capable of being used in accordance with claim 48. See MPEP §2114, §2115, §2173.05(g).
Applicant argues that the Izawa process using the claimed crude range would render the system unsatisfactory.
Examiner disagrees. The 99.00% - 99.99% 1,4-BDO of Izawa paragraph 14 is the purified 1,4-BDO product. Izawa teaches "It is possible to obtain the 1,4BG which is contained in the 1,4-butanediol-containing composition of the present invention by production methods which have hitherto been known. For example, there are included ... 1,4BG obtained by means of direct fermentation from a biomass" (Izawa paragraph 24, emphasis added). Thus, the claimed crude 1,4BDO is analogous to the 1,4BG obtained by fermentation of Izawa and the claimed purified 1,4-BDO product is analogous to the 1,4-butanediol-containing composition of Izawa. Thus, the proposed modification would not render the system unsatisfactory.
Further, that Izawa recognized a cost/benefit of both higher and lower final concentrations does not render achieving those concentrations nonobvious. Rather, one of ordinary skill would optimize the concentration for cost and stability depending on the specific system requirements.
Applicant argues that the proposed modifications would render the system unsatisfactory because Izawa teaches in ¶12-16 that an amide from 1 to 50 ppm makes the product more stable.
Examiner disagrees. The stabilizing amide would still be present in the proposed modification.
Izawa teaches where the amide may be added at different stages of the process, for instance “It is possible to obtain the 1,4-butanediol-containing composition of the above-described concentration range by directly adding the amide compound to commercially available 1,4BG, 1,4BG obtained by the above-described conventionally known production method of 1,4BG, or 1,4BG after purifying the 1,4BG, followed by preparation.” (¶29).
Further, as taught by Izawa, the amide composition would be fully capable of being included in the distillation step because Izawa teaches distillation (¶26) and adding the amide before the distillation step: “Furthermore, it is also possible to obtain the 1,4-butanediol-containing composition by adding the amide compound to the raw material by the above-described conventionally known production method of 1,4BG or on the way of a process of production step of such 1,4BG, followed by preparation.” (¶29).
Applicant argues that the ultrafiltration as taught by Dien (¶206, ¶212) and Clark (¶132-134) do not teach the claimed microfiltration.
Examiner agrees and the rejection is withdrawn.
Ultrafiltration and microfiltration are known in the art to be two distinct types of filtration. Applicant’s specification defines neither microfiltration nor ultrafiltration and a consistent definition of either term is not established in the prior art. Further, the various definitions in the prior art show that microfiltration of some definitions overlap with ultrafiltration of other definitions. However, the Dien and Clark teachings of “ultrafiltration” itself does not teach microfiltration.
However, upon further search and/or consideration the claimed microfiltration is taught by Clark (¶69, ¶75).
Applicant argues that because Okuyama teaches melt crystallization to allow for milder distillation conditions and a purity of about 97.7% renders the Izawa system unsatisfactory.
Examiner disagrees. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981).
Applicant argues that the fermentation broth of Clark is not compatible with the crude 1,4-BDO of Izawa.
Examiner disagrees. The 99.00% - 99.99% 1,4-BDO of Izawa paragraph 14 is the purified 1,4-BDO product.
Applicant argues that any modification of Izawa by Ernst would render the system unsatisfactory.
Examiner disagrees. Ernst is used to show that reducing thermal degredation and concentrating the distillate are appropriate motivations for modifying Izawa with Cvengros.
Applicant argues that because Okuyama teaches a hydrogenation reactor and subjecting the hydrogenated material to further redistillation that a modification to Izawa would render the system unsatisfactory.
Examiner disagrees. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981).
Applicant argues that the modification by Cvengros would not have been obvious because Cvengros does not teach feeding the distillate to a second distillation column.
Examiner disagrees. Okuyama teaches a separator/reboiler which feeds the distillate to a second distillation column. The Cvengros modification replaces the separator/reboiler with a wiped film evaporator to serve a similar function.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to STEPHEN HOBSON whose telephone number is (571)272-9914. The examiner can normally be reached 9am-5pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Dieterle can be reached at 571-270-7872. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/STEPHEN HOBSON/Examiner, Art Unit 1776