DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 1, 3-6, 8, 10, 11, and 15 are pending.
Claim 10 is amended.
Claims 2, 7, 9, 12-14, and 16 are cancelled.
Terminal Disclaimer
The terminal disclaimer filed on 07 October 2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Patent Numbers 11578024 and 12286393, i.e., the granted patent of US Application Number 18155597, have been reviewed and are accepted. The terminal disclaimer has been recorded.
Due to the recorded terminal disclaimer the nonstatutory double patenting rejections over the claims of U.S. Patent No. 11578024 to Yuan (hereinafter Yuan ‘024) and copending Application No. 18155597 to Yuan (hereinafter Yuan ‘597) are withdrawn.
Response to Amendments
Applicant’s amendments filed 07 October 2025 are acknowledged.
Drawings
Applicant’s amendment to the drawings is sufficient to overcome the objection of
the drawings. The drawings have been amended to comply with 37 CFR 1.84 (u)(1). The
objection is withdrawn.
Specification
Applicant’s amendment to the specification is sufficient to overcome the
objection of the specification. The specification has been amended to match the
drawings in compliance with 37 CFR 1.84 (u)(1). The objection is withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s cancellation of claims 9 and 16 is sufficient to overcome the rejections of claims 9 and 16 under 35 U.S.C. 112(d) 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. The rejections are withdrawn.
Applicant’s amendment to claim 10 is sufficient to overcome the rejection of claim 10 under 35 U.S.C. 112(d) 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. Claim 10 is amended to further limit the subject matter of the claim 1. The rejection is withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s cancellation of claims 9 and 16 is sufficient to overcome the rejection of claims 9 and 16 under 35 U.S.C. 103 as being unpatentable over Xiao et al. (US20130284584, hereinafter Xiao) in view of Barnicki (US20120184783) and Ren et al. (WO2018089600, hereinafter Ren). Due to the cancellation of the claims the rejection is withdrawn.
Response to Arguments
Applicant’s arguments filed 07 October 2025 have been fully considered; however, some are persuasive and some are not persuasive.
Applicant’s argue that Xiao, Barnicki, Ren and Woods do not disclose the limitations as recited in the claims. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
Applicant’s arguments in the remarks filed on 07 October 2025 with respect to Xiao and Woods have been considered but are moot because the new ground of rejection does not rely on Xiao and Woods applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicants state on pages 11-12 of the remarks filed on 07 October 2025, “[a]s amended herein, claim 1 recites: …”. It appears claim 1 is not amended with the filed remarks; therefore, independent claim 1 is herein examined on the merits as previously presented.
In response to applicant’s argument on page 12 of the remarks filed on 07 October 2025 that the “purity and ultraviolet transmittance of the resulting ethylene glycol are increased”. It is noted that purity and UV transmittance increase are not currently claimed.
In response to applicant’s argument on pages 14-15 of the remarks filed on 07 October 2025 that “Barnicki teaches away from distillation methods to separate mixed diols streams”. Barnicki teaches mixed diol stream 8 is distilled in column 4 to separate stream 9 comprising “water, hydrophobic solvent, higher-carbon-number diols, and/or ethylene glycol” from stream 13 comprising “purified ethylene glycol”, see Fig. 1; Paras. [0153]-[0154]. Therefore, Barnicki teaches distillation methods to separate mixed diols streams. For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s argument on page 15 of the remarks filed on 07 October 2025 that Ren “does not disclose or suggest processes for the separation of ethylene glycol from other diols”, 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). Ren teaches it in known in the prior art that a non-petroleum based ethylene glycol produced from agricultural waste comprises pentanediol, hexanediol and
PNG
media_image1.png
12
47
media_image1.png
Greyscale
, see Paras. [0016]-[0022]. Since a chemical composition and its properties are inseparable, see MPEP 2112.01, a non-petroleum based ethylene glycol produced from agricultural waste will comprise pentanediol, hexanediol and
PNG
media_image1.png
12
47
media_image1.png
Greyscale
, as taught by Ren. For the reasons indicated above, applicant’s above argument is not persuasive.
New Grounds of Rejection
Claim Rejections - 35 USC § 103
Due to the below new grounds of rejection and cancellation of claims, the rejection of claims 1, 3, 4, 6, 8-11, 15, and 16 under 35 U.S.C. 103 as being unpatentable over Xiao et al. (US20130284584, hereinafter Xiao) in view of Barnicki (US20120184783) and Ren et al. (WO2018089600, hereinafter Ren) is withdrawn.
Due to the below new grounds of rejection, the rejection of claim 5 under 35 U.S.C. 103 as being unpatentable over Xiao et al. (US20130284584, hereinafter Xiao) in view of Barnicki (US20120184783), Ren et al. (WO2018089600, hereinafter Ren), and Woods et al. (US20130036660, hereinafter Woods) is withdrawn.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1, 3-6, 8, 10, 11, and 15 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Regarding claim 1, the parenthetical “(absolute)” renders the claim indefinite because it is unclear whether the limitation within the parenthetical is part of the claimed invention, see MPEP § 2173.05(d).
Claims 3-6, 8, 10, 11, and 15 depend from base claim 1 and are included in this rejection as they do not correct the informalities identified in base claim 1.
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 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.
Claims 1, 3, 4, 6, 8, 10, 11, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Barnicki (US20120184783, published 19 July 2012) in view of Ren et al. (WO2018089600, published 17 May 2018, hereinafter Ren).
Barnicki relates to the known prior art of the separation and purification of a mixed diol stream to obtain ethylene glycol, see Abstract; Fig. 1: Paras. [0007]-[0018].
Regarding instant application claim 1, Barnicki teaches a process for refining a carbohydrate based ethylene glycol from a mixture of diols, see Paras. [0004];[0056]-[0058], Fig. 1, comprising:
(i) mixing one or more azeotropic agent extractant hydrophobic solvents feeds 20 and 21, such as n-heptanol, octane, n-nonanol, and n-decanol, with non-petroleum based mixed diols containing ethylene glycol feed 6 to obtain an azeotrope-containing ethylene glycol feed 8, see Fig. 1; Paras. [0057];[0068]-[0070];[0088];[0090]-[0091] & Table;[0153]-[0154], meeting step (i) and the specific azeotrope agents in instant application claim 1;
(ii) subjecting the azeotrope-containing ethylene glycol feed 8 to reflux in an distillation tower 4, see Fig. 1; Paras. [0153]-[0154], where the distillation is conducted at 0.2 bar absolute or 150 torr aka 20 kPa, see Paras. [0251]-[0252];[0256]-[0257], meeting step (ii) and within the pressure range in instant application claim 1;
(iii) extracted stream 9 containing ethylene glycol exits from the top of the distillation tower 4, see Fig. 1; Paras. [0087]-[0088];[0153]-[0154], meeting step (iii) in instant application claim 1;
(iv) extracted stream 9 already contains water or water is added to the distillate product to assist in the generation of two liquid phases, where the ethylene glycol partitions/dissolves into the water, see Paras. [0090]-[0091];[0154], meeting step (iv) in instant application claim 1;
(v) extracted stream 9 is decanted/separated in decanter 5 to create azeotropic agent extractant hydrophobic solvents feed streams 10 and 12, and hydrophilic phase containing ethylene glycol stream 11, see Fig. 1; Paras. [0153]-[0154], meeting step (v) in instant application claim 1;
(vi) hydrophilic phase containing ethylene glycol stream 11 is sent for further processing, such as by distillation where water and hydrophobic solvents are separated from the ethylene glycol, see Paras. [0071];[0091];[0100];[0153]-[0154];[0187], meeting step (vi) in instant application claim 1; and,
The mixed diol stream comprises (i) 0.1 weight percent to 50 weight percent of one or more diols selected from ethylene glycol, 1,2-propanediol, 1,3-propanediol 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol; (ii) 5 weight percent to 90 weight percent glycerol; each based on the total weight of the mixed diol stream with an extractant, see Paras. [0025]-[0030], meeting the ethylene glycol comprising ethylene glycol and butanediol in instant application claim 1.
Regarding instant application claims 3 and 4, Barnicki teaches one or more azeotropic agent extractant hydrophobic solvents include n-heptanol, octane, n-nonanol, and n-decanol, see Paras. [0068]-[0070];[0234]-[0235], Table, meeting the specific azeotropic agents in instant application claim 3 and in instant application claim 4.
Regarding instant application claim 8, Barnicki teaches the mixed diol derived by the hydrogenolysis of sorbitol glycerol, comprises about 40 to 90 weight percent 1,2-propanediol, about 10 to about 60 weight percent ethylene glycol, and about 0.1 to about 10 weight percent 1,2-butanediol, see Paras. [0025]-[0030];[0059];[0127], meeting the ethylene glycol in instant application claim 8.
Regarding instant application claim 10, Barnicki teaches the mixed diol stream comprises (i) 0.1 weight percent to 50 weight percent of one or more diols selected from ethylene glycol, 1,2-propanediol, 1,3-propanediol 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol; (ii) 5 weight percent to 90 weight percent glycerol; each based on the total weight of the mixed diol stream with an extractant, see Paras. [0025]-[0030], meeting and within the ranges in instant application claim 10.
Barnicki does not teach:
The instant application claim 1 limitation of wherein the non-petroleum based ethylene glycol comprises pentanediol, hexanediol and
PNG
media_image2.png
83
239
media_image2.png
Greyscale
;
The limitations of instant application claims 6, 11, and 15.
Ren relates to the known prior art of producing bio-based ethylene glycol, see Abstract.
Regarding instant application claim 1, Ren teaches wherein the bio-based ethylene glycol produced from agricultural waste comprising pentanediol, hexanediol and
PNG
media_image1.png
12
47
media_image1.png
Greyscale
aka of 2-[(5- methyltetrahydro-2-furanyl)methoxy]ethanol, see Paras. [0016]-[0022], meeting the composition of the ethylene glycol in instant application claim 1.
Regarding instant application claims 6 and 15, Ren teaches the bio-based ethylene glycol is extracted from plant mass, such as sugar cane, corn wheat, cassava, agricultural waste, and wood chips, see Paras. [0005]-[0006];[0013];[0016]-[0018], meeting the limitations in instant application claim 6 and in instant application claim 15.
Regarding instant application claim 11, Ren teaches impurities in the ethylene glycol effect the transparency of PET materials made from the ethylene glycol, see Paras. [0023]-[0025];[0036], meeting the limitations in instant application claim 11.
In addition, since a chemical composition and its properties are inseparable, see MPEP 2112.01, the bio-based ethylene glycol of Ren will have the ultraviolet transmittance affect as instantly claimed.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the carbohydrate feed source of Barnicki to be the plant based mass having the ethylene glycol impurities as taught by Ren with a reasonable predictability of success for the purpose of efficiently producing bio-derived ethylene glycol with the desired transparency for making bio-derived polyesters, see Ren, Paras. [0006]-[0009];[0023]-[0025];[0036].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Barnicki and Ren teach bio-derived ethylene glycol, a person of ordinary skill in the art has good reason to purify a biomass-derived mixed diol stream with select impurities by pursuing the known options within their technical grasp before the effective filing date of the claimed invention for the benefit of efficiently producing bio-derived ethylene glycol with the desired transparency for making bio-derived polyesters, see Ren, Paras. [0006]-[0009];[0023]-[0025];[0036] and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of the chemicals in the mixed diol feedstock, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as a carbohydrate ethylene glycol source, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as distillation pressures, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Barnicki (US20120184783, published 19 July 2012) in view of Ren et al. (WO2018089600, published 17 May 2018, hereinafter Ren), as applied to claims 1, 3, 4, 6, 8, 10, 11, and 15 in the 35 USC 103 rejection above, in further view of Frank et al. (“Separation of Glycol Ethers and Similar LCST-Type Hydrogen-Bonding Organics from Aqueous Solution Using Distillation or Liquid-Liquid Extraction”, published 2007, Industrial & Engineering Chemistry Research, Vol. 46, Pgs. 3774-3786, hereinafter Frank).
Barnicki teaches wherein the one or more azeotropic agents is 5-ethyl-2-nonanone, see Para. [0234], Table.
Barnicki does not teach the instant application claim 5 limitation of wherein the one or more azeotropic agents is 2-nonanone.
Frank relates to the known prior art of the azeotropic solvent distillation or liquid-liquid extraction of glycol ethers, see Abstract.
Regarding instant application claim 5, Frank teaches 2-nonanone aka methyl heptyl ketone is an azeotropic agent for the extraction of glycol ethers, such as ethylene glycol, from mixed aqueous fluids, see Pg. 3774, Introduction-Pg. 3775, Materials and Methods; Pg. 3779-3782, Liquid-Liquid Extraction Using a Steam-Strippable Solvent, Col. 1; Fig. 4; Tables 10-13, meeting the limitation in instant application claim 5.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the nonanone of Barnicki to be 2-nonanone as taught by Frank with a reasonable predictability of success for the purpose of efficiently extracting ethylene glycol from a mixture of diols in an aqueous solution, see Frank, Pgs. 3774-3775, Introduction.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Barnicki and Frank teach nonanone extractants, a person of ordinary skill in the art has good reason to purify a mixed diol aqueous stream by pursuing the known options within their technical grasp before the effective filing date of the claimed invention for the benefit of efficiently extracting ethylene glycol from a mixture of diols in an aqueous solution, see Frank, Pgs. 3774-3775, Introduction and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as a nonanone isomer, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571)270-3456. The examiner can normally be reached Monday-Thursday, 8 a.m. - 6 p.m., EST, with Flex Time.
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, Scarlett Yen-Ye Goon can be reached at (571) 270-5241. 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.
/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699