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 § 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 54-64 are 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.
Regarding claims 54 and 59, the phrase "for example" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
The parenthetic expression in claims 54-64 render the claims indefinite under 35 USC 112 (b) because it is unclear whether the phrases in parentheses are intended as part of the claim limitations.
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.
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 54-64 (are rejected under 35 U.S.C. 103 as being unpatentable over Yingli Chemical Technology hereafter “Yingli” CN 1408697 A).
Applicants’ claimed invention is directed to a method for making a dialkyl malonate ester, the method comprising: e) acidifying a malonate composition comprising: at least 30 wt.% based on malonic acid equivalents of a compound of formula I
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wherein M+ is a Group I alkali metal cation or ammonium cation, and wherein the malonate composition optionally further comprises at least one of: a compound of formula II
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And malonic acid;
wherein the acidifying of the malonate composition comprises contacting an organic
alcohol and an inorganic acid with the malonate composition to solubilize the malonate
composition and to form a first acidified malonate composition comprising at least one of: a compound of formula IV
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a compound of formula V
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malonic acid,
wherein R¹ and R² are independently (C₁-C₈)alkyl;
f) heating the first acidified malonate composition to form an esterified malonate
composition comprising the dialkyl malonate ester;
g) separating a precipitate comprising M⁺ from the esterified malonate composition;
h) distilling the esterified malonate composition of step g) to isolate a distillate
comprising the dialkyl malonate ester, wherein the distillate comprises greater than or equal to 90 wt.% dialkyl malonate ester.
Regarding claims 54, 58, 63 and 64, Yingli teaches a method for preparing malonic acid and its corresponding alkyl esters through a multi-step workflow. This begins with neutralizing and cyanating chloroacetic acid using an alkaline agent, followed by hydrolysis to form an alkali metal malonate salt matrix, which is subsequently acidified and esterified.
Acidification and esterification phase: Yingli discloses adding an organic acid (specifically teaching hydrochloric acid or sulfuric acid) along with an organic alcohol (such as methanol or ethanol) directly into the malonate composition stream. This reaction is carried out under reflux conditions to solubilize the salts and complete the esterification process. See abstract; description pages 2-3.
Precipitate separation: Yingli teaches that when the inorganic acid reacts with the initial sodium or alkali metal malonate salts, an inorganic byproduct salt precipitate due to its poor solubility in the alcohol/ester medium. The reference teaches removing this salts byproduct through standard solid-liquid separation (filtration). See description pages 2-3, Example 1.
Purification: following filtration, Yingli teaches subjecting the remaining liquid inorganic phase to fractional distillation to drive off excess alcohol and isolate the targeted dialkyl malonate ester product. See description pages 2-3, Example 1.
The differences between claimed invention and prior art
While Yingli teaches the process sequence of steps (e through h), specific quantitative thresholds and exact transient chemical concentrations are not explicitly disclose. The specific differences are:
The 30 wt.% thresholds of formula 1 (step e): present claim 54 requires the starting malonate composition to comprise at least 30 wt.% based on malonic acid equivalents of a formula 1 (HO-CO-CH2-COOM+). Yingli teaches starting with an aqueous malonate salt matrix but does not explicitly quantify the specific concentration or weight percentage of the mono alkali salt (formula 1) at the exact baseline point of acidification.
The ≥90 wt.% distillate purity (step h): present claim 54 explicitly recites that the final isolated distillate comprises greater than or equal to 90 wt.% dialkyl malonate ester. While Yingli teaches standard purification by distillation to collect the final ester fraction, it does not state a numerical purity threshold of 90 wt.% or greater in its main embodiments.
It would have been obvious to a person of ordinary skill in the art, prior to the effective filing date of the claimed invention to optimize the concentration of the intermediate mono-salt to at least 30 wt.% and the purification variables to achieve greater than or equal to 90 wt.% distillate purity. These specific numerical thresholds represent routine optimization of process stream variables within the capability of an ordinary process chemist to maximize chemical yield, and their selection yields predictable results.
Regarding claims 55-57 and 60-63, Yingli explicitly discloses methyl and ethyl groups, rendering these narrow limitations obvious in view of broader disclosure. Description pages 2-3, Ex. 1.
Regarding claim 59, independent claim 59 is distinguished from Yingli by a required two-stage acidification process that generates and advances a specific first and second acidified malonate composition, rather than a single-stage bulk acidification. The examiner asserts that this, along with specific concentration and purity constraints, constitutes routine optimization of an esterification to improve yields based on established chemical principles.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAFAR F PARSA whose telephone number is (571)272-0643. The examiner can normally be reached M-F 10:00 AM-6:30PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett 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.
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/JAFAR F PARSA/Primary Examiner, Art Unit 1692
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