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 .
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
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 13–17 and 23 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Yada et al. (U.S. Pub. 2004/0260122, hereafter US’122) in view of Ogawa et al. (U.S. Pub. 2006/0249365, hereafter US’365)
Claim 13
US’122 discloses a process for continuously distilling an acrylate by means of a rectification column. Figure 5 and paragraph [0096] disclose a distillation column 51 equipped with separating packing or trays 52, a reflux tank 56, a reboiler 58, a feed line 60, and bottom-liquid circulation lines 66 and 67. Paragraph [0119] explains that bottom liquid is removed from column 51 through line 66, heated in reboiler 58, and returned to the column bottom through line 67. The presence of separating packing, reflux, and a reboiler establishes that the disclosed distillation column operates as a rectification column. US’122 further states in paragraphs [0113]–[0114] that the distillation may be operated continuously.
More specifically, US’122’s Example 15 uses the Figure 5 apparatus to distill crude ethyl acrylate in a SUS304 column having a 13-meter packed separation region. See paragraph [0247]. The feed introduced through line 60 contains:
97.4 wt.% ethyl acrylate;
1.8 wt.% water;
0.4 wt.% acrylic acid;
0.4 wt.% ethanol; and
0.1 wt.% ethyl acetate.
The feed is supplied at 6,000 kg/h, and a hydroquinone inhibitor solution is supplied separately at 60 kg/h. US’122 reports stable continuous operation for one year. See paragraph [0248]. Thus, US’122 expressly teaches continuous rectification of a feed containing substantially more than the claimed minimum of 80 wt.% acrylate, with bottom liquid heated by an evaporator or reboiler.
US’122 does not expressly state that the parts of reboiler 58 that contact the product in Example 15 are made from stainless steel.
US’365 discloses reboilers used in distillation and evaporation columns handling readily polymerizable compounds, including acrylic acid and acrylates. Paragraph [0033] teaches that the materials for the column body, reboiler, tubes, and associated components are selected according to the compound and operating temperature. US’365 further teaches that stainless steels are commonly used in the production and purification of acrylic acid and acrylates and identifies SUS304, SUS304L, SUS316, SUS316L, SUS317, SUS317L, and SUS327 as suitable materials.
It would have been obvious to make the product-contacting portions of US’122’s reboiler 58 from one of the stainless steels taught by US’365. Both references concern distillation equipment processing the same class of readily polymerizable acrylic compounds, and US’365 expressly identifies stainless steel as a suitable material for the reboiler and its tubes in that service. The modification would have been the predictable use of a known construction material in a known component performing the same heat-transfer function, with a reasonable expectation of success.
Claim 14
Claim 14 further requires methyl acrylate, ethyl acrylate, n-butyl acrylate, or 2-ethylhexyl acrylate.
US’122’s Example 15 expressly uses ethyl acrylate. US’122 also identifies methyl acrylate, ethyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate among the acrylic esters to which its distillation process applies. See US’122, paragraph [0024] and Example 15, paragraphs [0247]–[0248].
Claims 15–17
Claims 15, 16, and 17 require feed acrylate contents of at least 85, 90, and 95 wt.%, respectively.
US’122 expressly discloses a feed containing 97.4 wt.% ethyl acrylate in Example 15, paragraph [0248]. That disclosure satisfies each of the claimed minimum concentrations.
Claim 23
Claim 23 further requires that the feed to the rectification column have an acid number of less than 10 mg KOH/g feed.
US’122’s principal feed contains 0.4 wt.% acrylic acid. The acid-number contribution from that acrylic acid is:
0.004 ((56.1056 g/mol KOH)/(72.0627 g/mol acrylic acid)) (1000) = 3.11 mg KOH/g
US’122 separately adds 60 kg/h of a 5 wt.% hydroquinone solution to the 6,000 kg/h principal feed. Even conservatively treating both phenolic hydrogens of the hydroquinone as titratable acid equivalents, the combined acrylic-acid and hydroquinone loading corresponds to approximately 3.59 mg KOH/g of total material introduced to the column. Both calculations are below the claimed 10 mg KOH/g maximum.
Claim 18
US’122 and US’365 teach the process of claim 13 as set forth above. Claim 18 further requires that the evaporator be a shell-and-tube heat exchanger.
US’365 teaches in paragraph [0027] that the reboiler may be a vertical fixed-tube-plate heat exchanger in which the liquid being processed flows through tubes and the heating medium flows through the surrounding shell. US’365 also identifies horizontal fixed-tube-plate and U-tube heat exchangers as suitable reboilers. The expressly disclosed arrangement of process-liquid tubes surrounded by a heating-medium shell is a shell-and-tube heat exchanger.
It would have been obvious to employ US’365’s shell-and-tube reboiler as reboiler 58 in US’122 because US’365 teaches that configuration for the identical bottom-liquid heating function in distillation columns handling the same class of acrylic compounds. The modification would have involved selecting one known reboiler configuration from a finite group of established heat-exchanger designs, with a reasonable expectation that it would heat and circulate the column-bottom liquid as intended.
Claims 19–22
Claims 19–22 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Yada et al. (U.S. Pub. 2004/0260122, hereafter US’122) in view of Ogawa et al. (U.S. Pub. 2006/0249365, hereafter US’365), and further in view of DE 10 2004 003 733 (hereafter DE’733).
US’122 and US’365 teach the continuous rectification process of claim 13, including the concentrated ethyl-acrylate feed, bottom-liquid heating by a reboiler, and stainless-steel product-contacting reboiler parts, for the reasons stated above.
DE’733 relates to producing and processing acrylic and methacrylic esters in apparatus constructed from selected stainless steels. Paragraph [0008] states that stainless steels under DIN EN 10088-1 contain at least 10.5 wt.% chromium. Paragraph [0011] discloses austenitic stainless steels having 16–28 wt.% chromium, 3.5–32 wt.% nickel, and optionally up to 7 wt.% molybdenum. Paragraph [0012] discloses austenitic-ferritic steels having 19–28 wt.% chromium, 3.5–8 wt.% nickel, and up to 4.5 wt.% molybdenum.
DE’733 also specifically identifies materials 1.4571, designated X6CrNiMoTi17-12-2; 1.4462, designated X2CrNiMoN22-5-3; and 1.4539, designated X1NiCrMoCuN25-20-5. These designations identify steels having nominal chromium, nickel, and molybdenum contents within the ranges recited in claims 19–21. See DE’733, paragraph [0013]. Paragraph [0122] expressly identifies evaporators, columns, and column internals as components suitably constructed from these stainless steels and states that evaporators are particularly preferred components.
It would have been obvious to use one of DE’733’s disclosed stainless-steel grades for the product-contacting parts of the evaporator taught by US’122 and US’365. DE’733 addresses materials for acrylic-ester processing apparatus and expressly identifies evaporators as suitable—and particularly preferred—components for those alloys. Selecting a disclosed corrosion-resistant stainless-steel grade for a known stainless-steel reboiler in the same acrylic-ester-processing environment would have been a predictable materials selection with a reasonable expectation of success.
Claim 19
Claim 19 requires that the product-contacting evaporator parts be made from stainless steel containing 10.5–30.0 wt.% chromium.
DE’733 discloses stainless steels containing 16–28 wt.% chromium and 19–28 wt.% chromium. Both disclosed ranges lie entirely within the claimed 10.5–30.0 wt.% range. DE’733’s specifically preferred material 1.4571 also has a nominal chromium content of approximately 17 wt.%. See paragraphs [0011]–[0013].
Construction applied to claims 20 and 21
Claims 20 and 21 recite “the parts of the condensation column” even though the dependency chain introduces a rectification column and an evaporator, not a condensation column. For purposes of prior-art examination only, “the condensation column” is construed as referring to the evaporator recited in claim 19, whose alloy composition appears to be further limited by claims 20 and 21. This construction does not resolve or withdraw the separate rejection under 35 U.S.C. § 112(b).
Claim 20
Claim 20 requires an additional nickel content of 2.0–35.0 wt.%. DE’733 discloses austenitic steels containing 3.5–32 wt.% nickel and austenitic-ferritic steels containing 3.5–8 wt.% nickel. Both ranges fall within the claimed range. DE’733’s specifically preferred material 1.4571 has a nominal nickel content of approximately 12 wt.%. See paragraphs [0011]–[0013].
Claim 21
Claim 21 requires an additional molybdenum content of 0.1–8.0 wt.%. DE’733’s specifically preferred material 1.4571, X6CrNiMoTi17-12-2, has a nominal molybdenum content of approximately 2 wt.%. Material 1.4462 has approximately 3 wt.% molybdenum, and material 1.4539 has approximately 5 wt.% molybdenum. Each disclosed amount falls within the claimed 0.1–8.0 wt.% range. See DE’733, paragraph [0013].
Claim 22
Claim 22 depends from claim 19 and further requires an acid number below 100 mg KOH/g feed. DE’733 supplies the chromium-containing stainless steel required by claim 19. US’122’s Example 15 feed has an acid number of approximately 3.11 mg KOH/g based on the expressly disclosed acrylic-acid concentration and no more than approximately 3.59 mg KOH/g under the conservative calculation that includes both potentially titratable hydrogens of the separately supplied hydroquinone. The disclosed feed therefore falls well below the claimed 100 mg KOH/g maximum.
Claim 24
Claim 24 is/are rejected under 35 U.S.C. § 103 as being unpatentable over EP 1 182 189 (hereafter EP’189), in view of DE 2 262 969 (hereafter DE’969), and further in view of Ogawa et al. (U.S. Pub. 2006/0249365, hereafter US’365).
EP’189 teaches a continuous process for producing and recovering n-butyl acrylate. After acrylic acid is neutralized and extracted, the acrylic-acid-free organic phase is dehydrated by distillation. Unreacted butanol is then removed overhead, and the bottom stream containing substantially pure butyl acrylate and inhibitors is passed to a final product-distillation column. Pure butyl acrylate is recovered overhead, with representative product purity exceeding 99.8 wt.%. See EP’189, paragraph [0029], corresponding to page 9, lines 472–480 of the B1 publication.
EP’189 therefore teaches a continuous acrylate-production and purification process in which a substantially pure—and thus at least 80 wt.%—n-butyl-acrylate stream is fed to a final rectification or distillation operation. EP’189 does not expressly quantify the acid number of that final-column feed as below 1 mg KOH/g.
DE’969 teaches continuous separation of n-butyl acrylate from acrylic-acid-containing mixtures. In Example 1, 820 g/h of n-butyl acrylate containing 1.5 wt.% acrylic acid is fed to a 50-tray column. The column bottom is heated to establish reflux, and the distillate and bottoms are continuously withdrawn. The distillate consists of n-butyl acrylate containing only 0.01 wt.% acid, calculated as acrylic acid. DE’969 further teaches in claim 2 that the separated acrylate stream may be subjected to further distillation to obtain pure acrylic ester.
The acid number corresponding to 0.01 wt.% acid calculated as acrylic acid is:
0.0001 (56.1056/72.0627) (1000) = 0.0779 mg KOH/g. The DE’969 stream therefore satisfies the claim 24 requirement of less than 1 mg KOH/g.
US’365 teaches that a conventional distillation column for readily polymerizable acrylic compounds contains trays or packing and a reboiler for heating and circulating the column-bottom liquid. Paragraphs [0027] and [0033] teach that the reboiler may be a shell-and-tube heat exchanger and that the reboiler and its tubes may be made from stainless steels such as SUS304, SUS316, and SUS317.
It would have been obvious to use the low-acid n-butyl-acrylate stream taught by DE’969 as the feed to EP’189’s final product-distillation column. EP’189 expressly teaches feeding substantially pure n-butyl acrylate to a final distillation step, while DE’969 teaches obtaining an n-butyl-acrylate stream containing only 0.01 wt.% acid and expressly contemplates further distillation of that stream to obtain pure ester. Both references concern sequential purification of n-butyl acrylate, and the proposed combination would predictably use a known low-acid feed in a known final-polishing distillation to obtain high-purity product.
It further would have been obvious to employ US’365’s stainless-steel reboiler in the combined EP’189-DE’969 final-distillation process because US’365 teaches that construction for the same bottom-liquid heating function in columns processing readily polymerizable acrylic esters. The modification would have been a predictable use of a known reboiler material and configuration, with a reasonable expectation of successful operation.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 20-21 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 20 recites “the parts of the condensation column that are in contact with product,” and claim 21 contains the same recitation. However, “the condensation column” lacks antecedent basis in the claims. Independent claim 13 introduces a “rectification column” and an “evaporator,” and claim 19 further limits the stainless-steel composition of “the parts of the evaporator that are in contact with product.” Neither claim 19 nor any preceding claim in the dependency chain introduces a condensation column.
The intended meaning of “the condensation column” also cannot be determined with reasonable certainty from the specification. The specification separately identifies a rectification column, an evaporator located in the bottom region of the rectification column, and a condenser located in the top region of the rectification column. It is therefore unclear whether the nickel limitation of claim 20 and the molybdenum limitation of claim 21 are intended to apply to the product-contacting portions of the rectification column, the evaporator, the condenser, or a separate condensation column that has not otherwise been defined.
Because the identity of the component having the recited alloy composition materially affects the scope of the claims, a person of ordinary skill in the art would not be able to determine the metes and bounds of claims 20 and 21 with reasonable certainty. Claims 20 and 21 are therefore indefinite.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691
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