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 . This is a first action on the merits of the application. Claims 1-20 are pending.
Election/Restrictions
Applicant's election without traverse of invention I, claims 1-12 in the reply filed on February 02, 2026 is acknowledged. Claims 13-20 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
Claim Objections
Claims 1 and 5 are objected to because of the following informalities:
Claim 1 recites “condensing the light-ends stream to form one or more liquid phase compositions and 139” which appears to be a misspelling of “condensing the light-ends stream to form one or more liquid phase compositions
Claim 5 recites “The method of claim 4, wherein removing comprises:” in line 1. It is respectfully suggested to amend the limitation to “The method of claim 4, wherein the removing comprises:”.
Appropriate corrections are required.
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 1-12 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 regard(s) as the invention.
Claim 1 recites “a majority of the water and acetic acid” and “a majority of the carbon monoxide and carbon dioxide” in lines 7-8 and “a minor portion of the acetaldehyde, methyl iodide, water, and acetic acid” in line 8-9. These are considered indefinite for the following reason: The basis for determining “majority” or “minor” is unspecified and, as a result, those claims are unclear.
Claim 1 recites “condensing the light-ends stream to form one or more liquid phase compositions and a vapor phase composition,” in lines 5-6. This is considered indefinite for the following reason: The apparatus for conducting the condensing the light-ends stream is unspecified. For clarification purposes, it is respectfully suggested to amend the limitation to “condensing the light-ends stream in a flash vessel to form one or more liquid phase compositions and a vapor phase composition,” in view of the Specification (Fig. 1; paragraph [0024]) of the claimed invention.
Claim 1 recites “contacting a reactive feed stream” in line 15. This is considered indefinite for the following reason: The apparatus for conducting the contacting a reactive feed stream is unspecified. For clarification purposes, it is respectfully suggested to amend the limitation to “contacting a reactive feed stream in an acetaldehyde reactor” in view of the Specification (Fig. 1A; paragraph [0070]) of the claimed invention.
Claims 2-12 are also rejected under 35 U.S. §112 by virtue of its dependence on claim 1.
Claim 10 recites “the decanter” which lacks an antecedent basis.
Allowable Subject Matters and Allowed claims
Claims 1-12 in the instant application are allowed if previously presented objection to claims 1 and 5, and 35 U.S.C. 112(b) rejections to claims 1-12 are resolved.
The following is an examiner’s statement of reasons for allowance: A thorough search for pertinent prior art did not locate any prior art that discloses or suggests the invention recited in claims 1-12. The concept of a method for removing acetaldehyde from an acetic acid system, comprising:
providing from the acetic acid system a light-ends stream, comprising carbon monoxide, carbon dioxide, acetaldehyde, methyl iodide, methyl acetate, methanol, water, acetic acid, or mixtures thereof;
condensing the light-ends stream to form one or more liquid phase compositions and a vapor phase composition, wherein the one or more liquid phase compositions comprise a majority of the water and acetic acid, and the vapor phase composition comprises a majority of the carbon monoxide and carbon dioxide and a minor portion of the acetaldehyde, methyl iodide, water, and acetic acid;
contacting the vapor phase composition with a solvent in an absorber to produce an absorber overhead vapor stream and an absorber bottoms liquid stream, wherein the absorber overhead vapor stream comprises carbon monoxide, carbon dioxide, and a first portion of the solvent, and the absorber bottoms liquid stream comprises methyl iodide, acetaldehyde, and a second portion of the solvent; and
contacting a reactive feed stream, comprising the absorber bottoms liquid stream, and optionally a polyol compound, with an acid catalyst in to form a reacted stream comprising an aldehyde derivative, wherein the aldehyde derivative is formed by conversion of at least a portion of the acetaldehyde and has a higher boiling point than acetaldehyde (claim 1), is considered novel.
A closest prior art to Fisher et al. (US 5,783,731) discloses a process for the carbonylation of methanol to a product of acetic acid, said methanol is carbonylated in a reaction medium containing a Group VIII metal catalyst, an organic iodide, and iodide salt promoter; the products of said carbonylation separated into a volatile phase comprising product and a less volatile phase comprising Group VIII metal catalyst, acetic acid, iodide catalyst promoter, and organic iodide; said product phase distilled in a distillation tower to yield a purified product and an overhead organic iodide, methyl acetate, water, acetic acid, and unreacted methanol, and recycling said overhead to said carbonylation reactor, the improving consisting of: (a) directing at least a portion of the overhead to an overhead receiver which separates the overhead into a light phase, comprising acetic acid and water, and a heavy phase comprising methyl acetate and organic iodide; (b) venting a light gas stream from the overhead receiver of (a) to a chiller; (c) chilling the vented gas stream of (b) under suitable conditions to condense the chilled vented gas stream into a condensed phase and separate in an overhead receiver vessel said condensed phase from noncondensable light gases; (d) contacting the condensed phase of (c) with an aqueous amino compound which forms water soluble nitrogenous derivatives of carbonyls; (e) separating out resulting nitrogenous derivatives of carbonyls and returning a purified condensed phase of (c) to the carbonylation reactor.
Other pertinent prior art to Harris et al. (US 7,524,988 B2) discloses a method for reducing an aldehyde impurity from acetic acid stream, said method comprising: (a) reacting methanol and carbon monoxide in the presence of a carbonylation catalyst, a catalyst stabilizer, methyl iodide, water and methyl acetate to produce an acetic acid stream comprising the catalyst, the catalyst stabilizer, methyl iodide, methyl acetate, water, acetic acid, and an aldehyde impurity; (b) flashing at least a portion of the acetic acid stream to a vapor stream comprising acetic acid, water, methyl acetate, methyl iodide and the aldehyde impurity, and a liquid stream comprising the catalyst and the catalyst stabilizer; (c) recycling the liquid stream to the reaction of step (a); (d) separating the vapor stream by distillation into an acetic acid product stream comprising acetic acid and water, and an overhead stream comprising methyl iodide, water, methyl acetate, acetic acid, and the aldehyde impurity; (e) condensing the overhead stream to produce a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide and the aldehyde impurity; (f) reacting at least a portion of the heavy, organic phase with a hydroxyl compound selected from the group consisting of C4-10 alcohols, glycols, and glycerin to convert the aldehyde impurity to an acetal having a higher boiling point than acetic acid; (g) recycling the treated heavy phase of step (f) to the distillation of step (d), wherein the acetal goes with the acetic acid product stream as a heavy impurity; and (h) separating the acetal from the acetic acid product stream of step (g) by distillation.
Other pertinent prior art to Shimizu (US 2020/0079719 A1) discloses a method for producing acetic acid, the method comprising the steps of: (A) carbonylating methanol with carbon monoxide in a reactor in the presence of a catalytic system, acetic acid, methyl acetate, and water, to form acetic acid in a reaction mixture, the catalytic system including a metal catalyst and methyl iodide; (B) separating the reaction mixture, using at least one selected from evaporators and distillation columns, into: a stream including the metal catalyst; an acetic acid stream rich in acetic acid; and a stream richer in light ends than the acetic acid stream; (C) recycling by subjecting the light ends-rich stream to condensation and liquid-liquid separation to give an aqueous phase and an organic phase, and recycling at least a part of at least one of the aqueous phase and the organic phase to the reactor; (D) liquid-liquid separating a process stream including water, acetic acid, methyl iodide, and acetaldehyde into: an aqueous phase; and an organic phase; and (E) removing acetaldehyde derived from the process stream by a treatment of an object, the object being selected from at least a part of at least one of the aqueous phase and the organic phase based on a factor or factors selected from the group consisting of: a liquid temperature in the liquid-liquid separation in the liquid-liquid separation step (D); an acetaldehyde concentration in at least one of the aqueous phase and the organic phase; an acetaldehyde partition coefficient; a methyl acetate concentration in at least one of the aqueous phase and the organic phase; and a methyl acetate partition coefficient, wherein the separation step (B) comprises the substep of (B′) yielding, by separation using a first distillation column: a first acetic acid stream rich in acetic acid; and an overhead stream richer in light ends than the first acetic acid stream, wherein, in the substep (B′), a crotonaldehyde concentration in the first acetic acid stream is controlled to 2.2 ppm by mass or less, and a ratio (CCR/CECR) of the crotonaldehyde concentration CCR (ppm by mass) to an 2-ethylcrotonaldehyde concentration CECR (ppm by mass) in the first acetic acid stream is regulated.
Other pertinent prior art to Broussard et al. (US 2003/0199711 A1) discloses a process for the production of acetic acid by the catalytic carbonylation of methanol with carbon monoxide, in a system comprising a reaction section and a purification section, comprising the steps of: (a) producing a stream comprising acetic acid and acetaldehyde; (b) reducing the acetaldehyde content of at least a portion of the stream by treating at least a portion of the stream with an oxidizing agent; and (c) directing at least a portion of the treated stream to a portion of the system selected from the group consisting of the reaction section, the purification section, and both the reaction section and the purification section.
Other pertinent prior art to Sawyer et al. (US 2008/0051601 A1) discloses a method for producing acetic acid, said method comprising: (a) reacting methanol and carbon monoxide in the presence of a carbonylation catalyst, a catalyst stabilizer, methyl iodide, water and methyl acetate to produce an acetic acid stream comprising acetic acid, water, methyl acetate, methyl iodide, the catalyst, the catalyst stabilizer, and an aldehyde impurity; (b) flashing at least a portion of the acetic acid stream to produce a vapor stream comprising acetic acid, water, methyl acetate, methyl iodide and the aldehyde impurity, and a liquid stream comprising the catalyst and the catalyst stabilizer; (c) separating the vapor stream using a distillation column into an acetic acid product stream comprising acetic acid, the aldehyde impurity, and a minor amount of water, and an overhead stream comprising methyl iodide, water, acetic acid, and methyl acetate; (d) feeding the acetic acid product stream and a hydroxyl compound into a distillation column, wherein the aldehyde impurity reacts with the hydroxyl compound to form an acetal, and wherein the water is removed from a top portion of the distillation column and an essentially anhydrous acetic acid product stream comprising acetic acid and the acetal is taken from the distillation column; and (e) separating the acetal from acetic acid by distillation.
Other pertinent prior art to Fitzpatrick et al. (US 2011/0054213 A1) discloses a method for reducing aldehydes from an acetic acid production process by reacting methanol and carbon monoxide in the presence of a carbonylation catalyst to produce at least one aldehyde-containing stream, said method comprising reacting the aldehyde-containing stream with an alcohol to form an acetal-containing stream, separating an acetal-enriched stream from the acetal-containing stream, hydrolyzing the acetal-enriched stream to form a hydrolysis mixture comprising the alcohol and the aldehydes, isolating the alcohol from the hydrolysis mixture, and recycling the alcohol to the acetal-forming step.
Other pertinent prior art to Hallinan et al. (US 7,345,197 B1) discloses a method for removing an aldehyde from acetic acid, said method comprising: (a) reacting methanol and carbon monoxide in the presence of a carbonylation catalyst, a catalyst stabilizer, methyl iodide, water and methyl acetate to produce an acetic acid stream containing an aldehyde; (b) flashing at least a portion of the acetic acid stream into a vapor stream comprising acetic acid, water, methanol, methyl acetate, methyl iodide and the aldehyde, and a liquid stream comprising the catalyst and the catalyst stabilizer; (c) separating the vapor stream by distillation into a product stream comprising acetic acid and water, and an overhead stream comprising methyl iodide, water, methyl acetate, and the aldehyde; (d) condensing and separating the overhead stream in a decanter into a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide and the aldehyde; and (e) extracting the aldehyde from the heavy, organic phase with a polyol.
The cited prior arts, alone or in combination, do not teach or suggest a method for removing acetaldehyde from an acetic acid system, comprising the specific features of “contacting the vapor phase composition with a solvent in an absorber to produce an absorber overhead vapor stream and an absorber bottoms liquid stream, wherein the absorber overhead vapor stream comprises carbon monoxide, carbon dioxide, and a first portion of the solvent, and the absorber bottoms liquid stream comprises methyl iodide, acetaldehyde, and a second portion of the solvent; and contacting a reactive feed stream, comprising the absorber bottoms liquid stream, and optionally a polyol compound, with an acid catalyst in to form a reacted stream comprising an aldehyde derivative, wherein the aldehyde derivative is formed by conversion of at least a portion of the acetaldehyde and has a higher boiling point than acetaldehyde” as recited in claim 1 of claimed invention.
Conclusion
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/YOUNGSUL JEONG/Primary Examiner, Art Unit 1772