Purification Or Recovery Patents (Class 560/248)
  • Patent number: 4843170
    Abstract: 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: Grant
    Filed: February 15, 1983
    Date of Patent: June 27, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
  • Patent number: 4841081
    Abstract: 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: Grant
    Filed: October 14, 1986
    Date of Patent: June 20, 1989
    Assignee: Osaka Soda Co., Ltd.
    Inventors: Fumio Toda, Koichi Tanaka, Tetsuya Nakata
  • Patent number: 4826576
    Abstract: 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: Grant
    Filed: June 2, 1986
    Date of Patent: May 2, 1989
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4818347
    Abstract: 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: Grant
    Filed: December 10, 1987
    Date of Patent: April 4, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Roscher, Karl H. Schmidt, Hansjorg Hey, Horst Langner, Erwin Andereya
  • Patent number: 4724049
    Abstract: 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: Grant
    Filed: June 26, 1986
    Date of Patent: February 9, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4718988
    Abstract: 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: Grant
    Filed: March 27, 1986
    Date of Patent: January 12, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4698137
    Abstract: 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: Grant
    Filed: March 5, 1986
    Date of Patent: October 6, 1987
    Inventor: Lloyd Berg
  • Patent number: 4695350
    Abstract: 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: Grant
    Filed: January 27, 1986
    Date of Patent: September 22, 1987
    Inventor: Lloyd Berg
  • Patent number: 4693789
    Abstract: 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: Grant
    Filed: March 5, 1986
    Date of Patent: September 15, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4690734
    Abstract: 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: Grant
    Filed: November 25, 1985
    Date of Patent: September 1, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4683341
    Abstract: The optical resolution of an enantiomer mixture of oxycyclopentenone or a derivative thereof is conducted with a polysaccharide derivative.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: July 28, 1987
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kunio Ishii, Tohru Shibata
  • Patent number: 4676874
    Abstract: 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: Grant
    Filed: November 7, 1985
    Date of Patent: June 30, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4670106
    Abstract: 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: Grant
    Filed: December 2, 1985
    Date of Patent: June 2, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4668820
    Abstract: 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: Grant
    Filed: April 10, 1985
    Date of Patent: May 26, 1987
    Assignee: Kuraray Co., Ltd.
    Inventors: Koichi Ibata, Tetsuo Takigawa, Masafumi Okada, Masao Mizuno, Takashi Nishida
  • Patent number: 4666560
    Abstract: 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: Grant
    Filed: October 11, 1985
    Date of Patent: May 19, 1987
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4665221
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: May 12, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Thoemel, Werner Hoffmann
  • Patent number: 4664753
    Abstract: 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: Grant
    Filed: August 6, 1984
    Date of Patent: May 12, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
  • Patent number: 4642167
    Abstract: 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: Grant
    Filed: March 7, 1985
    Date of Patent: February 10, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4597834
    Abstract: 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: Grant
    Filed: February 17, 1984
    Date of Patent: July 1, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4592805
    Abstract: 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: Grant
    Filed: December 14, 1984
    Date of Patent: June 3, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4569726
    Abstract: 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: Grant
    Filed: July 19, 1984
    Date of Patent: February 11, 1986
    Inventors: Lloyd Berg, Pisant Ratanapupech
  • Patent number: 4544453
    Abstract: 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: Grant
    Filed: May 31, 1984
    Date of Patent: October 1, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Vijai P. Gupta
  • Patent number: 4543164
    Abstract: 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: Grant
    Filed: April 14, 1983
    Date of Patent: September 24, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4525245
    Abstract: 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: Grant
    Filed: May 7, 1984
    Date of Patent: June 25, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4522760
    Abstract: 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: Grant
    Filed: July 23, 1982
    Date of Patent: June 11, 1985
    Assignee: Rhone-Poulenc Chimie de Base
    Inventor: Jean Jenck
  • Patent number: 4521595
    Abstract: 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: Grant
    Filed: July 16, 1982
    Date of Patent: June 4, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Stuhler, Engelbert Krempl
  • Patent number: 4517377
    Abstract: 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: Grant
    Filed: June 18, 1982
    Date of Patent: May 14, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Takanari Nawata, Yasuhiko Kijima, Akira Ito, Takayuki Watanabe
  • Patent number: 4507176
    Abstract: 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: Grant
    Filed: May 7, 1984
    Date of Patent: March 26, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4487959
    Abstract: 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: Grant
    Filed: April 12, 1983
    Date of Patent: December 11, 1984
    Assignee: Ecolochem, Inc.
    Inventor: Richard C. Dickerson
  • Patent number: 4481146
    Abstract: 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: Grant
    Filed: September 29, 1981
    Date of Patent: November 6, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst I. Leupold, Hans-Joachim Schmidt, Knut Popp
  • Patent number: 4480124
    Abstract: 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: Grant
    Filed: March 11, 1982
    Date of Patent: October 30, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4473444
    Abstract: 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: Grant
    Filed: May 10, 1982
    Date of Patent: September 25, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventors: Julian Feldman, John M. Hoyt
  • Patent number: 4450294
    Abstract: 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: Grant
    Filed: November 1, 1982
    Date of Patent: May 22, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventor: Julian Feldman
  • Patent number: 4447643
    Abstract: 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: Grant
    Filed: August 11, 1982
    Date of Patent: May 8, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventor: Julian Feldman
  • Patent number: 4442303
    Abstract: 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: Grant
    Filed: December 9, 1980
    Date of Patent: April 10, 1984
    Assignee: El Paso Products Company
    Inventor: Samuel S. Mims
  • Patent number: 4433175
    Abstract: 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: Grant
    Filed: November 24, 1982
    Date of Patent: February 21, 1984
    Assignee: Chemische Werke Huels, A.G.
    Inventor: Manfred Kaufhold
  • Patent number: 4433165
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventor: Thomas C. Singleton
  • Patent number: 4433166
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventors: Thomas C. Singleton, Frank E. Paulik
  • Patent number: 4431838
    Abstract: 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: Grant
    Filed: February 8, 1982
    Date of Patent: February 14, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventors: Julian Feldman, John M. Hoyt
  • Patent number: 4413140
    Abstract: 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: Grant
    Filed: April 26, 1977
    Date of Patent: November 1, 1983
    Assignee: Phillips Petroleum Company
    Inventor: George B. Fozzard
  • Patent number: 4381407
    Abstract: 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: Grant
    Filed: January 26, 1981
    Date of Patent: April 26, 1983
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Norbert Bremus, Gerhard Dieckelmann, Lutz Jeromin, Wolfgang Rupilius, Hartwig Schutt
  • Patent number: 4379940
    Abstract: 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: Grant
    Filed: October 27, 1980
    Date of Patent: April 12, 1983
    Assignee: Ecolochem, Inc.
    Inventor: Richard C. Dickerson
  • Patent number: 4379028
    Abstract: 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: Grant
    Filed: March 30, 1982
    Date of Patent: April 5, 1983
    Inventors: Lloyd Berg, Pisant Ratanapupech
  • Patent number: 4370491
    Abstract: 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: Grant
    Filed: May 14, 1981
    Date of Patent: January 25, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Rudolf Irnich, Eberhard Schaefer
  • Patent number: 4364869
    Abstract: 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: Grant
    Filed: July 29, 1981
    Date of Patent: December 21, 1982
    Assignee: Chemische Werke Huls A.G.
    Inventors: Wolfgang H. E. Muller, Peter Hofmann
  • Patent number: 4350572
    Abstract: 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: Grant
    Filed: November 6, 1980
    Date of Patent: September 21, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Volker Taglieber, Franz-Josef Weis, Heinz-Walter Schneider
  • Patent number: 4334061
    Abstract: 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: Grant
    Filed: October 29, 1979
    Date of Patent: June 8, 1982
    Assignee: Ethyl Corporation
    Inventor: Joseph A. Bossier, III
  • Patent number: 4319039
    Abstract: 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: Grant
    Filed: August 11, 1980
    Date of Patent: March 9, 1982
    Assignee: Merck & Co., Inc.
    Inventor: George Albers-Schonberg
  • Patent number: 4314947
    Abstract: 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: Grant
    Filed: December 21, 1978
    Date of Patent: February 9, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Hohenschutz, Josef Gnad, Guenter Dinkhauser, Eberhard Schaefer
  • Patent number: RE31010
    Abstract: 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: Grant
    Filed: June 11, 1981
    Date of Patent: August 10, 1982
    Assignee: Chem Systems Inc.
    Inventor: Abraham P. Gelbein