Purification Or Recovery Patents (Class 560/248)
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Patent number: 4843170Abstract: A process is disclosed for producing vinyl acetate from methanol, carbon monoxide and hydrogen which comprises the following five steps:(a) methanol is hydrocarbonylated in a hydrocarbonylation zone to produce ethanol, acetaldehyde, methyl acetate and dimethylacetal, and the products are separated in a separation zone;(b) methyl acetate is carbonylated in a carbonylation zone to produce acetic anhydride;(c) the acetaldehyde and dimethylacetal produced in the step (a) and the acetic anhydride produced in the step (b) are converted to ethylidene diacetate and methyl acetate; (d) the ethylidene diacetate produced in the step (c) is thermally decomposed to vinyl acetate and acetic acid, and the products are separated in a separation zone; and(e) the methyl acetate produced and separated in the step (a), (c) or (d) is supplied to the carbonylation step (b).Type: GrantFiled: February 15, 1983Date of Patent: June 27, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
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Patent number: 4841081Abstract: A method of optically resolving a racemate, or a diastereomeric mixture, of a substituted or unsubstituted glycidyl ester or ether compound having at least one glycidylic structure represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent H or CH.sub.3, and 1 to 3 asymmetric carbon atoms in the molecule, or a racemate of a beta-dihalohydrin ester compound, which comprises contacting said racemate or diastereomeric mixture with an optically active form of a compound having the following formula (I) ##STR2## wherein X represents a halogen atom, to form an inclusion complex compound having the optically active compound of formula (I) as a host, and separating the resulting complex compound.Type: GrantFiled: October 14, 1986Date of Patent: June 20, 1989Assignee: Osaka Soda Co., Ltd.Inventors: Fumio Toda, Koichi Tanaka, Tetsuya Nakata
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Patent number: 4826576Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate--isopropanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is a mixture of a polyol and one or higher boiling oxygenated, nitrogenous and/or sulfur containing organic compounds. Typical examples of effective agents are 1,3-butanediol and dimethylsulfoxide; 1,2,6-hexanetriol, dimethylsulfoxide and dimethylformamide.Type: GrantFiled: June 2, 1986Date of Patent: May 2, 1989Assignee: Lloyd BergInventors: Lloyd Berg, An-I Yeh
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Patent number: 4818347Abstract: The invention relates to a process for the isolation of vinyl acetate from a gas mixture containing vinyl acetate, ethyl acetate, water and carbon dioxide formed in the reaction of ethylene with acetic acid and oxygen in the gas phase over catalysts containing palladium or palladium compounds. The gas mixture leaving the reaction zone is passed into a distillation column and the gas mixture leaving the top thereof is cooled. The gas which is not condensed during the cooling is washed with acetic acid in a washing column, an acetic acid solution containing vinyl acetate being obtained. The bottom product from the distillation column is passed to a second distillation column and a side stream containing ethyl acetate is removed from an enrichment zone above the bottom thereof, all or some of the bottom product from the second distillation column, which product chiefly consists of acetic acid, being used for the wash in the washing column. The top vapor of the second distillation column is cooled.Type: GrantFiled: December 10, 1987Date of Patent: April 4, 1989Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Karl H. Schmidt, Hansjorg Hey, Horst Langner, Erwin Andereya
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Patent number: 4724049Abstract: Isobutyl acetate cannot be completely removed from isobutyl acetate - isobutanol - water mixtures by distillation because of the presence of the minimum ternary axeotrope. Isobutyl acetate can be readily removed from mixtures containing it, isobutanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; dimethylsulfoxide and dimethylformamide; dimethylsulfoxide, dimethylformamide and N,N-dimethylacetamide.Type: GrantFiled: June 26, 1986Date of Patent: February 9, 1988Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4718988Abstract: 2-Butyl acetate cannot be completely removed from 2-butyl acetate-2-butanol-water mixtures by distillation because of the presence of the minimum ternary azeotrope. 2-butyl acetate can be readily removed from mixtures containing it, 2-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide; dimethylformamide and ethylene glycol; acetamide, dimethylsulfoxide and ethylene glycol.Type: GrantFiled: March 27, 1986Date of Patent: January 12, 1988Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4698137Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate - isopropanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed for mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are dimethylformamide; dimethylformamide and triethanolamine; N,N-dimethylacetamide and N-methyl pyrrolidone.Type: GrantFiled: March 5, 1986Date of Patent: October 6, 1987Inventor: Lloyd Berg
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Patent number: 4695350Abstract: n-Hexyl acetate cannot be completely removed from n-hexyl acetate- n-hexyl alcohol- water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Hexyl acetate can be readily removed from mixtures containing it, n-hexyl alcohol and water by using extractive distillation in which the extractive distillation agent is dimethylsulfoxide or a mixture of DMSO with a higher boiling organic compound. Typical examples of effective agents are DMSO; DMSO and tetraethylene glycol; DMSO, dimethylformamide and hexylene glycol.Type: GrantFiled: January 27, 1986Date of Patent: September 22, 1987Inventor: Lloyd Berg
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Patent number: 4693789Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate - isopropanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is a higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are diethanolamine; ethanolamine and N-methyl pyrrolidone; triethanolamine and N-methyl pyrrolidone.Type: GrantFiled: March 5, 1986Date of Patent: September 15, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4690734Abstract: n-Amyl acetate cannot be completely removed from n-amyl acetate - n-amyl alcohol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Amyl acetate can be readily removed from mixtures containing it, n-amyl alcohol and water by using extractive distillation in which the extractive distillation agent is a higher boiling organic compound or a mixture of these. Typical examples of effective agents are ethylene glycol; propylene glycol and dimethylsulfoxide; 1,3-butanediol, dimethylformamide and acetamide.Type: GrantFiled: November 25, 1985Date of Patent: September 1, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4683341Abstract: The optical resolution of an enantiomer mixture of oxycyclopentenone or a derivative thereof is conducted with a polysaccharide derivative.Type: GrantFiled: December 12, 1985Date of Patent: July 28, 1987Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Ishii, Tohru Shibata
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Patent number: 4676874Abstract: n-Propyl acetate cannot be completely removed from n-propyl acetate - n-propanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Propyl acetate can be readily removed from mixtures containing it, n-propanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are N-methylpyrrolidone; triethanolamine; N-methylpyrrolidone and ethylene glycol.Type: GrantFiled: November 7, 1985Date of Patent: June 30, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4670106Abstract: n-Amyl acetate cannot be completely removed from n-amyl acetate - n-amyl alcohol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Amyl acetate can be readily removed from mixtures containing it, n-amyl alcohol and water by using extractive distillation in which the extractive distillation agent is a higher boiling organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; N,N-dimethylacetamide and dimethylsulfoxide; dimethylformamide, N,N-dimethylacetamide and acetamide.Type: GrantFiled: December 2, 1985Date of Patent: June 2, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4668820Abstract: Polyprenols or esters thereof, which are similar in the trans and cis configurations to dolichol, or mixtures thereof are obtained from the leaves of plants belonging to the genus Pinus L. of the family Pinaceae by extraction, if necessary followed by hydrolysis, esterification or transesterification or a combination thereof. These polyprenyl compounds and mixtures thereof are useful as favorable starting materials for the synthesis of dolichol.Type: GrantFiled: April 10, 1985Date of Patent: May 26, 1987Assignee: Kuraray Co., Ltd.Inventors: Koichi Ibata, Tetsuo Takigawa, Masafumi Okada, Masao Mizuno, Takashi Nishida
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Patent number: 4666560Abstract: Isopropanol cannot be completely removed from isopropanol - isopropyl acetate - water mixtures by distillation because of the presence of the minimum ternary azeoptrope. Isopropanol can be readily removed from mixtures containing it, isopropyl acetate and water by using extractive distillation in which the extractive agent is a higher boiling benzoate or nitro paraffin. Typical examples are methyl benzoate; methyl benzoate and nitromethane; butyl benzoate, nitromethane and nitroethane.Type: GrantFiled: October 11, 1985Date of Patent: May 19, 1987Inventors: Lloyd Berg, Mark G. Vosburgh
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Patent number: 4665221Abstract: An improved process for the preparation of primary terpenoid alcohols, e.g. 6,7-dihydrogeraniol and phytol, and of their esters with formic acid. The terpenoid formates are obtained very advantageously by reacting the corresponding tert.-vinylcarbinols with more than 2 moles, per mole of vinylcarbinol, of aqueous formic acid of more than 70 percent strength by weight, or with anhydrous formic acid, at from 5.degree. to 100.degree. C. The primary terpenoid alcohols themselves are obtained from their formates by trans-esterification with a low-boiling alcohol in the presence of a catalytic amount of a strong base. The products are valuable compounds. For example, 6,7-dihydrogeraniol is used as a scent and phytol is used as a perfume fixative and as a starting material for the synthesis of naturally occurring materials.Type: GrantFiled: July 25, 1983Date of Patent: May 12, 1987Assignee: BASF AktiengesellschaftInventors: Frank Thoemel, Werner Hoffmann
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Patent number: 4664753Abstract: The disclosure relates to a process for separating iodine and its compounds from the carbonlyation products acetic acid, acetic anhydride or ethylidene diacetate obtained by subjecting dimethylether, methyl acetate or methanol to a carbonylation reaction. For reducing the quantity of total iodine contaminating the carbonlyation products to less than 20 ppb iodine, the disclosure provides for the carbonylation products to be treated at temperatures of 20.degree. to 250.degree. C. with an alkyl or aryl phosphine or a heterocyclic aromatic nitrogen compound and at least one of the metals copper, silver, zinc or cadmium or their compounds and to be distillatively separated from the iodine thereby fixed in non-volatile form.Type: GrantFiled: August 6, 1984Date of Patent: May 12, 1987Assignee: Hoechst AktiengesellschaftInventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
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Patent number: 4642167Abstract: Isobutyl acetate cannot be completely removed from isobutyl acetate--isobutanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isobutyl acetate can be readily removed from mixtures containing it, isobutanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide; dimethylformamide and dimethylsulfoxide; acetamide, dimethylformamide and dipropylene glycol.Type: GrantFiled: March 7, 1985Date of Patent: February 10, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4597834Abstract: Methyl acetate cannot be completely removed from methyl acetate - methanol mixtures by distillation because of the presence of the minimum binary azeotrope. Methyl acetate can be readily removed from mixtures containing it and methanol by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylformamide; dimethylsulfoxide plus tetraethylene glycol, dimethylsulfoxide plus 1,5-pentanediol plus 1,6-hexanediol.Type: GrantFiled: February 17, 1984Date of Patent: July 1, 1986Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4592805Abstract: n-Propyl acetate cannot be completely removed from n-propyl acetate - n-propanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Propyl acetate can be readily removed from mixtures containing it, n-propanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Examples of effective agents are N,N-dimethylacetamide; acetamide and triethylene glycol; acetamide and N,N-dimethylacetamide and triethanolamine.Type: GrantFiled: December 14, 1984Date of Patent: June 3, 1986Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4569726Abstract: Ethyl acetate cannot be completely removed from ethanol and water mixtures by distillation because of the presence of the minimum ternary azeotrope. Ethyl acetate can be readily removed from mixtures containing it, ethanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, sulfur containing or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: 1,4-butanediol; ethylene glycol-1,5-pentanediol; propylene glycol-tetraethylene glycol-polyethylene glycol; glycerine-propylene glycol-tetraethylene glycol-1,4-butanediol.Type: GrantFiled: July 19, 1984Date of Patent: February 11, 1986Inventors: Lloyd Berg, Pisant Ratanapupech
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Patent number: 4544453Abstract: An improved method of stripping unreacted alkylene glycol monoalkyl ethers and unreacted monocarboxylic or halogenated monocarboxylic acids from a mixture containing the monocarboxylic acid ester prepared therefrom by acid catalyzed esterification without any significant loss of the product ester. The method involves the injection of water into the distillate during the stripping and is particularly suitable for the recovery of propylene glycol monomethyl ether and acetic acid from esterification reaction mixtures containing a predominate amount of product propylene glycol monomethyl ether acetate. The process allows for removal and recovery or recycle of the ether and acid and the preparation of a higher purity product ester.Type: GrantFiled: May 31, 1984Date of Patent: October 1, 1985Assignee: Atlantic Richfield CompanyInventor: Vijai P. Gupta
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Patent number: 4543164Abstract: Methyl acetate cannot be completely removed from methyl acetate-methanol mixtures by distillation because of the presence of the minimum binary azeotrope. Methyl acetate can be readily removed from mixtures containing it and methanol by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; glycerine plus propylene glycol; ethylene glycol plus DMSO plus 1,5-pentanediol. Methanol can be removed as the overhead product from methyl acetate when the extractive distillation agent is nitrobenzene, propylene carbonate or ethylene glycol phenyl ether.Type: GrantFiled: April 14, 1983Date of Patent: September 24, 1985Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4525245Abstract: n-Butyl acetate cannot be completely removed from n-butyl acetate - n-butanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Butyl acetate can be readily removed from mixtures containing it, n-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; dimethylsulfoxide and 1,4-butanediol; dimethylsulfoxide, dimethylformamide and 1,6-hexanediol.Type: GrantFiled: May 7, 1984Date of Patent: June 25, 1985Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4522760Abstract: Palladium values are separated from the products of reaction resulting from the carbonylation of a conjugated diene with carbon monoxide in the presence of an alcohol, a halogenated hydracid and a palladium catalyst, by (i) contacting the carbonylation reaction medium with a nitrogen, phosphorus or arsenic quaternary onium salt, a polar alcohol and an apolar, aliphatic or cycloaliphatic hydrocarbon solvent, and permitting the resulting admixture to phase separate into an alcohol phase and an organic phase; (ii) decanting/separating said alcohol phase from said organic phase; (iii) recovering the palladium values and the quaternary onium salt from said alcohol phase; and (iv) recovering the products of carbonylation from said organic phase.Type: GrantFiled: July 23, 1982Date of Patent: June 11, 1985Assignee: Rhone-Poulenc Chimie de BaseInventor: Jean Jenck
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Patent number: 4521595Abstract: A process for the purification of esters, which contain residues of dissolved and/or undissolved alcohols, is described. The purification of the esters containing alcohols is achieved by treating the esters, in the liquid state, with an effective amount of water-soluble polysaccharide derivatives in the solid state.Type: GrantFiled: July 16, 1982Date of Patent: June 4, 1985Assignee: Hoechst AktiengesellschaftInventors: Herbert Stuhler, Engelbert Krempl
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Patent number: 4517377Abstract: A process for producing vinyl acetate which comprises decomposing ethylidene diacetate in the presence of at least one compound selected from fluorides, bromides, chlorides, iodides, halogens and mixtures thereof is disclosed. According to this invention decomposition rate of ethylidene diacetate is high and selectivity to vinyl acetate is also high.Type: GrantFiled: June 18, 1982Date of Patent: May 14, 1985Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Takanari Nawata, Yasuhiko Kijima, Akira Ito, Takayuki Watanabe
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Patent number: 4507176Abstract: n-Butyl acetate cannot be completely removed from n-butyl acetate-n-butanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Butyl acetate can be readily removed from mixtures containing it, n-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide, dimethylsulfoxide and acetamide, ethylene glycol propylene glycol, dimethylsulfoxide and acetamide.Type: GrantFiled: May 7, 1984Date of Patent: March 26, 1985Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4487959Abstract: A process for purifying vinyl acetate contaminated with acetic acid, coloration agents, water, and/or cations and anions. A first stage consists of removing acetic acid from a vinyl acetate feed by dehydrating a commercially-available anion exchange resin by means of azeotropic distillation and passing the feed through a bed of the dehydrated resin. A second stage can consist of removing coloration agents by passing the vinyl acetate feed through a bed of activated carbon. A third stage can consist of removing water by passing the vinyl acetate feed through a bed of desiccant. A fourth stage can consist of removing cations and anions by passing the vinyl acetate feed through separate cation exchange resin and anion exchange resin beds or through a mixed resin bed.Type: GrantFiled: April 12, 1983Date of Patent: December 11, 1984Assignee: Ecolochem, Inc.Inventor: Richard C. Dickerson
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Patent number: 4481146Abstract: The invention relates to a process for the preparation of an ethyl ester from ethanol-containing mixtures of aliphatic alcohols, which comprises esterifying the alcohols with a carboxylic acid in the presence of an acid catalyst in a distilling column and separating in the same column the ethyl ester continuously from the ester mixture obtained. To this purpose, the alcohol mixture is introduced into the sump and the carboxylic acid is introduced into the column at a point located in the central part and the ethyl ester as well as the water formed during esterification are withdrawn continuously at the top of the column and the higher esters are withdrawn continuously at the sump.Type: GrantFiled: September 29, 1981Date of Patent: November 6, 1984Assignee: Hoechst AktiengesellschaftInventors: Ernst I. Leupold, Hans-Joachim Schmidt, Knut Popp
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Patent number: 4480124Abstract: The subject invention relates to a process for purifying polytetramethylene ether glycol or the corresponding diester prepared by cationic polymerization of tetrahydrofuran comprising treating said glycol or diester with hydrogen in the presence of a hydrogen catalyst. The resulting products have a low color number.Type: GrantFiled: March 11, 1982Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4473444Abstract: A C.sub.1 -C.sub.4 alkanol and its corresponding acetate or a C.sub.1 -C.sub.2 alkanol and its corresponding propionate are separated by extractive distillation utilizing an aromatic hydrocarbon as the extractive solvent. Transesterification of lower alkanols and lower alkyl acetates or propionates is effected by means of extractive distillation and the preparation of an intermediate ester of a higher boiling alcohol.Type: GrantFiled: May 10, 1982Date of Patent: September 25, 1984Assignee: National Distillers and Chemical CorporationInventors: Julian Feldman, John M. Hoyt
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Patent number: 4450294Abstract: An oxygenated organic compound, such as ethanol, is recovered from a dilute aqueous stream thereof by contacting said stream with crosslinked polyvinylpyridine resin or nuclear substituted derivative thereof to effect selective sorption of the compound by said resin. The sorbed compound is thereafter removed from the resin by stripping with an inert gas such as carbon dioxide.Type: GrantFiled: November 1, 1982Date of Patent: May 22, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4447643Abstract: A thermally efficient process for recovering an oxygenated organic material, such as ethanol, present in dilute aqueous solution is disclosed which comprises contacting said dilute aqueous solution with at least one inert extractant which is liquid at ambient temperature and pressure, said extractant being selected from the group consisting of unsubstituted and substituted cyclic secondary amines and unsubstituted and substituted aromatic cyclic amines having a distribution coefficient of at least about 0.70 or a separation factor of at least about 1.0.Type: GrantFiled: August 11, 1982Date of Patent: May 8, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4442303Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.Type: GrantFiled: December 9, 1980Date of Patent: April 10, 1984Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4433175Abstract: For the production of neohexanol with a purity above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, 3,3-dimethylbutyric acid with a chlorine content below 650 ppm, preferably below 100 ppm, is first esterified, optionally after distillatory separation into a portion richer in chlorine with a chlorine content above 650 ppm, preferably above 100 ppm, and into a portion low in chlorine with a chlorine content below 650 ppm, preferably below 100, with an alcohol boiling above 117.degree. C., preferably an octyl alcohol. The resultant ester is separated by distillation into fractions richer in chlorine with chlorine contents above 10 ppm and into fractions low in chlorine with chlorine contents below 10 ppm. The ester of low chlorine contents below 10 ppm is hydrogenated to neohexanol over a barium-activated copper chromite catalyst under a pressure of 200-300 bar, at 120.degree.-22.degree. C., and with catalyst loads of 0.05-1.Type: GrantFiled: November 24, 1982Date of Patent: February 21, 1984Assignee: Chemische Werke Huels, A.G.Inventor: Manfred Kaufhold
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Patent number: 4433165Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer component selected from N,N,N',N'-tetramethyl-o-phenylenediamine and 2,3'-dipyridyl.Type: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventor: Thomas C. Singleton
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Patent number: 4433166Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.Type: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
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Patent number: 4431838Abstract: A C.sub.1 -C.sub.4 alkanol and its corresponding acetate or a C.sub.1 -C.sub.2 alkanol and its corresponding propionate are separated by extractive distillation utilizing an aromatic hydrocarbon as the extractive solvent. Transesterification of lower alkanols and lower alkyl acetates or propionates is effected by means of extractive distillation and the preparation of an intermediate ester of a higher boiling alcohol.Type: GrantFiled: February 8, 1982Date of Patent: February 14, 1984Assignee: National Distillers and Chemical CorporationInventors: Julian Feldman, John M. Hoyt
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Patent number: 4413140Abstract: A solvent comprising at least one aromatic hydrocarbon and/or halogenated paraffin is used in a liquid extraction process for extracting diesters from mixtures comprising diesters, the corresponding monoesters and acids, diols and water.Type: GrantFiled: April 26, 1977Date of Patent: November 1, 1983Assignee: Phillips Petroleum CompanyInventor: George B. Fozzard
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Patent number: 4381407Abstract: A process for the continuous production of triacetin consisting essentially of continuously charging liquid glycerol into a first liquid reaction area through which acetic acid vapors and water vapors flow, said liquid reaction area being divided into a number of separate individual areas through which liquid glycerol and liquid acetin reaction products flow in one direction and gaseous acetic acid and water flow in a countercurrent direction, continuously charging acetic acid vapor to a separate individual area where said liquid mixture has an OH number of less than 600, continuously separating a liquid mixture of acetins and water having an OH number of less than 600, continuously passing said liquid mixture into a second liquid reaction area, continuously adding thereto liquid acetic acid anhydride in an amount sufficient to react with water dissolved in said liquid mixture to form acetic acid and to react with monoacetin and diacetin present to form triacetin and continuously recovering triacetin.Type: GrantFiled: January 26, 1981Date of Patent: April 26, 1983Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Norbert Bremus, Gerhard Dieckelmann, Lutz Jeromin, Wolfgang Rupilius, Hartwig Schutt
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Patent number: 4379940Abstract: A process for purifying vinyl acetate contaminated with acetic acid, coloration agents, water, and/or sodium chloride. The first stage consists of removing acetic acid by passing the vinyl acetate feed through a dehydrated anion exchange resin bed. The second stage consists of removing coloration agents by passing the vinyl acetate feed through a bed of activated carbon. The third stage consists of removing water by passing the vinyl acetate feed through a bed of desiccant. The fourth stage consists of removing sodium chloride by passing the vinyl acetate feed through separate cation exchange resin and anion exchange resin beds or through a mixed resin bed.Type: GrantFiled: October 27, 1980Date of Patent: April 12, 1983Assignee: Ecolochem, Inc.Inventor: Richard C. Dickerson
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Patent number: 4379028Abstract: Ethyl acetate cannot be completely removed from ethanol and water mixtures by distillation because of the presence of the minimum ternary azeotrope. Ethyl acetate can be readily removed from mixtures containing it, ethanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated of nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: dimethylsulfoxide, glycerine and diethylene glycol, 1-naphthol, hydroquinone and N,N-dimethylformamide.Type: GrantFiled: March 30, 1982Date of Patent: April 5, 1983Inventors: Lloyd Berg, Pisant Ratanapupech
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Patent number: 4370491Abstract: A process for the preparation of acetic acid esters CH.sub.3 --CO--O--R.sup.1 (I, R.sup.1 =an organic radical other than methyl and ethyl) by alkali-catalyzed trans-esterification of an acetic acid ester CH.sub.3 --CO--O--R.sup.2 (II, R.sup.2 =methyl or ethyl) with an alcohol R.sup.1 --OH (III), accompanied by elimination of the alcohol R.sup.2 --OH (IV), wherein(a) the trans-esterification reaction is carried out in the middle section K.sub.M of a distillation column K, the alcohol III being fed as liquid into the upper zone and the ester II into the lower zone of K.sub.M,(b) the alkaline catalyst is introduced into the upper part K.sub.U of K,(c) the alcohol IV, or a mixture of IV and the ester II, is taken off the top of the column,(d) the mixture obtained from (c) (unless the alcohol IV alone is obtained) is separated in the column section K.sub.U or in a stripper column K.sub.S into IV and the azeotrope of II and IV, and the latter is recycled to the lower zone of K.sub.Type: GrantFiled: May 14, 1981Date of Patent: January 25, 1983Assignee: BASF AktiengesellschaftInventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Rudolf Irnich, Eberhard Schaefer
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Patent number: 4364869Abstract: A process for the production of alkyl esters of saturated aliphatic carboxylic acids by reacting in an alkoxycarbonylation stage olefins with carbon monoxide and alkanol in the presence of a catalyst consisting of a cobalt compound and a promoter from the group of pyridine, non-ortho-substituted alkylpyridine or mixtures thereof at elevated pressure and elevated temperature. The reaction mixture produced is reprocessed and the pyridine, non-ortho-substituted alkylpyridine, or mixture used as the promoter is rectified prior to its feedback into the alkoxycarbonylation stage in the presence of a given carboxylic acid which is thermally stable under the conditions of reprocessing and which forms a maximum azeotrope with the promoter under the conditions of rectification.Type: GrantFiled: July 29, 1981Date of Patent: December 21, 1982Assignee: Chemische Werke Huls A.G.Inventors: Wolfgang H. E. Muller, Peter Hofmann
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Patent number: 4350572Abstract: A process for purifying carboxylic acid esters which have been obtained by reacting olefinically unsaturated compounds with carbon monoxide and alkanols and which contain aldehydes or acetals, wherein the said esters are treated with a strongly acidic agent, with or without addition of water.Type: GrantFiled: November 6, 1980Date of Patent: September 21, 1982Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Volker Taglieber, Franz-Josef Weis, Heinz-Walter Schneider
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Patent number: 4334061Abstract: A process for recovering polyol fatty acid polyesters from the crude reaction product in which it is produced by contacting with an aqueous washing medium in the presence of an emulsion decreasing organic solvent so that the alkali metal fatty acid soaps and the color-forming bodies are taken into the aqueous phase, and upon settling the phases are separated from each other.Type: GrantFiled: October 29, 1979Date of Patent: June 8, 1982Assignee: Ethyl CorporationInventor: Joseph A. Bossier, III
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Patent number: 4319039Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise compounds which have structures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.Type: GrantFiled: August 11, 1980Date of Patent: March 9, 1982Assignee: Merck & Co., Inc.Inventor: George Albers-Schonberg
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Patent number: 4314947Abstract: A process for completing the esterification of aliphatic carboxylic acids of 1 to 8 carbon atoms with aliphatic or cycloaliphatic alcohols of 3 to 10 carbon atoms at the boiling point of the alcohol in a column operated with bottom heating, the lower space of the column being free from fitments, the middle space being provided with a packing and the upper space being provided with a packing or other fitments, in which process the water of esterification is driven off at the top of the column by azeotropic distillation, the starting mixture is fed into the side of the column from 5 to 10 m above the liquid level, the ester formed is taken off as liquid from the column bottom, and the column is operated with flooding such that the liquid level is from 6 to 10 m, with the liquid mixture filling the lower column space, which is free from fitments, and the lower part of the packed layer above the said space.Type: GrantFiled: December 21, 1978Date of Patent: February 9, 1982Assignee: BASF AktiengesellschaftInventors: Heinz Hohenschutz, Josef Gnad, Guenter Dinkhauser, Eberhard Schaefer
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Patent number: RE31010Abstract: In a process wherein ethylene or propylene is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, the invention concerns a technique wherein the catalyst is recovered from the reaction product and recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed, to form a reaction mass containing the BF.sub.3, the alcohol, and the carboxylic acid ester in a 2:1:1 molar ratio. In the first step, the one mole of the free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the three aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. A carboxylic acid ester/alcohol azeotrope and residual alcohol are removed by the distillation, to leave a residue containing a 1:2 BF.sub.3 /alcohol complex. This complex is combined with an additional mole of BF.sub.Type: GrantFiled: June 11, 1981Date of Patent: August 10, 1982Assignee: Chem Systems Inc.Inventor: Abraham P. Gelbein