By Alcoholysis, Hydrolysis, Or Saponification Of An Ester Patents (Class 568/877)
  • Patent number: 5635542
    Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: June 3, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel
  • Patent number: 5550297
    Abstract: A process for catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al.sub.2 O.sub.3, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m.sup.2 /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r.sub.p .ltoreq.15 nm.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhardt Horn, Carl D. Frohning
  • Patent number: 5426250
    Abstract: 1,4-butanediol is prepared from allyl alcohol containing allyl acetate and water. The allyl alcohol is subjected to a hydroformylation reaction in the presence of an organic solvent, a rhodium complex, and a phosphorous compound under an atmosphere of carbon monoxide and hydrogen, to produce a hydroformylation product, which is extracted with an alkaline aqueous solution in the presence of carbon monoxide and/or hydrogen. After the extraction, an extracted raffinate solution containing the rhodium complex in the organic solvent is recycled through the same hydroformylation process, while the extracted aqueous solution containing the hydroformylation product is subjected to a hydrogenation reaction in the presence of hydrogen, with a hydrogenation catalyst added, to produce 1,4-butanediol.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: June 20, 1995
    Assignee: Darien Chemical Corporation
    Inventors: Shien C. Chen, Cheng C. Chu, Fu S. Lin, June Y. Chou
  • Patent number: 5294740
    Abstract: A process for preparing formic acid by thermal cleavage of quaternary ammonium formates of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are C.sub.1 - to C.sub.14 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, aryl or C.sub.7 - to C.sub.16 -aralkyl, or together are 1,4- or 1,5-alkylene which is unsubstituted or substituted one to four times by C.sub.1 -to C.sub.4 -alkyl, with the proviso that the sum of the carbon atoms of R.sup.1, R.sup.2 and R.sup.3 in the quaternary ammonium formates I is 7 to 40,comprises carrying out the cleavage in the presence of secondary formamides of the general formula II ##STR2## where R.sup.4 and R.sup.5 are C.sub.2 - to C.sub.10 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, aryl or C.sub.7 - to C.sub.16 -aralkyl, or together are 1,4- or 1,5-alkylene which is unsubstituted or substituted one to four times by C.sub.1 - to C.sub.4 -alkyl,which formamides boil 30.degree. to 150.degree. C. lower than the tertiary amine of the general formula III ##STR3## where R.sup.1, R.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Kiefer, Leopold Hupfer, Ferdinand Lippert
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5198592
    Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: March 30, 1993
    Assignee: Engelhard De Meern B.V.
    Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
  • Patent number: 5159124
    Abstract: An aqueous acid solution is mixed with an organic water-immiscible solvent which contains saponified and unsaponified compounds, which are obtained by saponifying a wax with an alkali in the solvent, to obtain an acidified mixture having a pH of from 2.5 to 4. The mixture is allowed to separate into an aqueous phase and an organic phase, and then the aqueous phase is separated from the organic phase. An alkaline earth metal hydroxide is mixed with the organic phase to form salts of fatty acids, and in cases when an insoluble material is formed from the organic phase, the insoluble material is separated from the organic phase. Unsaponified compounds are obtained from the organic phase by evaporating the organic phase. Salts of fatty acids may be removed from the compounds.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: October 27, 1992
    Assignee: Nestec S.A.
    Inventor: Raymond Bertholet
  • Patent number: 5157168
    Abstract: An improved process for the production of fatty alcohols is provided. The fatty alcohols are produced by hydrogenation of lower alkyl esters, especially methyl esters, of fatty acids derived from natural triglycerides, under conditions which minimize formation of by-product alkanes and ethers. The hydrogenation is followed by refining of any resulting ester-containing hydrogenation product to produce a substantially ester free fatty alcohol.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: October 20, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: Martyn Wilmott, George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5138106
    Abstract: An improved process for refining alcohols produced by hydrogenation of esters wherein the crude hydrogenation product still contains a minor amount of unconverted ester starting material. In one embodiment, the process includes a method for recovering fatty alcohol or alcohols from a fatty alcohol fraction containing a major molar amount of at least one fatty alcohol and a minor molar amount of at least one lower alkyl fatty acid ester. In another embodiment, there is provided a process for the production of fatty alcohols which comprises, in addition to other steps, hydrogenating a lower alkyl fatty acid ester to yield a mixture of a lower alkanol, a fatty alcohol fraction and a minor amount of unreacted lower alkyl fatty acid ester.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: August 11, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: Martyn Wilmott, George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5095155
    Abstract: Closely boiling diastereomeric isomer alcohols are separated by converting them to esters having disparate boiling points, separating the ester isomers by distillation and saponifying the separate ester isomers to obtain the individual alcohol isomers.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: March 10, 1992
    Assignee: Union Camp Corporation
    Inventor: Peter W. D. Mitchell
  • Patent number: 4924026
    Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen, and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: May 8, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4880937
    Abstract: An alcohol compound is produced by reducing a carboxylic acid or an ester thereof with an alcohol in the presence of a solid catalyst. The catalyst includes a hydrous metal oxide belonging to Group IV of the Periodic Table.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: November 14, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
  • Patent number: 4822913
    Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: April 18, 1989
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 4663477
    Abstract: A process is provided for the utilization of dialkyl carbonates formed as by-products in a continuous process for the synthesis of oxalic acid esters from nitrous acid esters and carbon monoxide and wherein the esters are subsequently used as intermediates in the production of commercially useful products, such as ethylene glycol. The process comprises contacting a mixture containing the by-product comprised of a dialkyl carbonate with an aqueous solution of a metal carbonate under hydrolyzing conditions whereby the dialkyl carbonate is converted to the corresponding alkanol and the metal carbonate is converted to metal bicarbonate. Upon distillation of the alkanol from the mixture the bicarbonate is converted back to the metal carbonate which can then be recycled from the bottoms to the hydrolyzing zone for use in further hydrolysis of by-product. The alkanol is recycled for use in the continuous process.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: May 5, 1987
    Assignee: Union Carbide Corporation
    Inventors: John W. Crandall, James E. Deitzler, Louis A. Kapicak, Fedor Poppelsdorf
  • Patent number: 4658053
    Abstract: A process for the production of an ester comprises reacting an olefin with carbon monoxide, hydrogen and another ester at elevated temperature and pressure in the presence of a catalyst comprising (1) a rhodium source, (2) a ruthenium source, and (3) cobalt or zinc iodide. The product ester comprises the acid group of the ester used as reactant esterified with a hydrocarbyl group derived from the olefin, hydrogen and carbon monoxide.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: April 14, 1987
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4647689
    Abstract: Alkyl trifluoroacetoacetates are prepared by acetylation of alkyl 3-alkoxy-3-hydroxy-4,4,4-trifluorobutanoates.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: March 3, 1987
    Assignee: Monsanto Company
    Inventor: Edward Micinski
  • Patent number: 4629809
    Abstract: A process for producing acetic acid is disclosed which comprises reacting methanol with carbon monoxide at an elevated temperature and pressure in the presence of an iodine-free catalyst system wherein the catalyst consists of ruthenium compound, quaternary phosphonium salt, cobalt-compound and inorganic acid or an organic acid, reacted in combination in a liquid form or a ruthenium on inert solid support catalyst with a sulfur-containing acid promoter.
    Type: Grant
    Filed: July 21, 1983
    Date of Patent: December 16, 1986
    Assignee: Texaco Inc.
    Inventors: Steven H. Vanderpool, Jiang-Jen Lin, Roger G. Duranleau
  • Patent number: 4560792
    Abstract: A process for producing functional monoolefins having specific types of cis to trans ratios involving disproportionating a functional monoolefin with a hydrocarbyl monoolefin consisting essentially of either (1) an internal olefin or (2) a terminal olefin. Also disclosed are functional olefin compositions useful in controlling insects.
    Type: Grant
    Filed: July 20, 1982
    Date of Patent: December 24, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Dennis S. Banasiak
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4524223
    Abstract: A general method of resolution of chiral alcohols is based on the relatively facile chromatographic resolution of their diastereomeric esters with optically active amino acids. The naturally occurring L-amino acids and D-(-)-phenylglycine are especially useful, and the method is applicable to a range of alcohols of diverse structure.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: June 18, 1985
    Assignee: UOP Inc.
    Inventor: David W. House
  • Patent number: 4461729
    Abstract: A method for preparation of secondary alcohol mixtures by selective reaction of an olefin or olefin mixture and a carboxylic acid compound in the presence of a particular type of shape selective zeolite catalyst. The reaction selectively produces .alpha.-methylalkyl carboxylate enriched ester product which, upon subsequent hydrolysis, yields the desired 2-alcohol enriched secondary alcohol product.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: July 24, 1984
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4461730
    Abstract: A method for the preparation of secondary alcohol mixtures by selective reaction of an olefin or olefin mixture and a carboxylic acid compound in the presence of zeolite mordenite. The reaction selectively produces .alpha.-methylalkyl carboxylate enriched ester product which, upon subsequent hydrolysis, yields the desired secondary alcohol product enriched in alcohols having hydroxy functionality at the 2-position.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: July 24, 1984
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4451678
    Abstract: A process for producing ethanol which comprises reacting methanol, carbon monoxide and hydrogen in the presence of (a) a catalyst comprising cobalt or a cobalt compound and an alkyl phosphine as an effective component and (b) a co-catalyst comprising hydrochloric acid and in the absence of an iodide is disclosed. According to the present invention, formation of by-products becomes less and selectivity to realizable ethanol becomes higher.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: May 29, 1984
    Assignee: Agency of Industrial Science and Technology
    Inventors: Nobuo Isogai, Motoyuki Hosokawa, Takashi Okawa, Natsuko Wakui, Toshiyasu Watanabe
  • 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: 4415747
    Abstract: This process is concerned with the reductive coupling of .alpha.-halo ethers and/or .alpha.-halo esters to make ethylene glycol derivatives by carrying out the reductive coupling process in the presence of an iron compound having iron in an oxidation state of zero.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: November 15, 1983
    Assignee: Union Carbide Corporation
    Inventor: Leonard Kaplan
  • Patent number: 4384148
    Abstract: Alcohols may be obtained by the indirect hydration of olefinic hydrocarbons in which the olefinic hydrocarbon is esterified by treatment with an organic acid such as acetic acid. The organic esters may then be hydrolyzed by treatment with water to form hydrolysis products comprising alcohols and ethers which may be separated from the reconstituted organic acid. The alcohol products are then separated from the ether product, the latter which may then be further treated by thermal cracking, decomposition, or hydrolysis to form an additional amount of the desired alcohol.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: May 17, 1983
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4374286
    Abstract: Alcohols may be obtained by an indirect hydration of olefinic hydrocarbons in which the olefinic hydrocarbon is first esterified by treatment with an inorganic acid to form dialkyl and alkyl hydrogen salts. These salts are then trans-esterified by treatment with an organic acid to form an organic ester. The reconstituted inorganic acid is separated from this mixture by stripping and recycled, while the organic esters are then treated with water in a hydrolysis step to reconstitute the organic acid and form the desired alcohol and ether. The alcohol product is separated from the ether which may then be further treated by thermal decomposition or hydrolysis to form an additional amount of the desired alcohol.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: February 15, 1983
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4352940
    Abstract: In the hydrolysis of methyl acetate to acetic acid, the improvement comprising a flasher or stripper to separate methyl acetate and water from the hydrolyzer product stream and the recycle of these directly to the hydrolyzer.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: October 5, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert L. Adelman, Roy Segars, Jr.
  • Patent number: 4301084
    Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Bernd Meissner
  • Patent number: 4299981
    Abstract: Formic acid is produced in a continuous process by hydrolyzing methyl formate with water at high temperature and pressure in the presence of a formic acid catalyst. Methanol is also formed. The reesterification of the reaction products to methyl formate (a reaction favored by high temperatures) is minimized by flashing the reaction product at relatively low pressure and temperature and thereafter distilling the residual liquid under vacuum. This procedure separates the methyl alcohol from the formic acid with a minimum contact time and at a low temperature which does not favor the reesterification reaction. The flashed vapor, primarily unreacted methyl formate, is recycled to the reaction zone. High purity formic acid, i.e., 85%, is obtained by subjecting the bottom from the vacuum distillation to a second distillation step. The distillate from the vacuum distillation is distilled to separate residual methyl formate for recycle from the co-product methyl alcohol.
    Type: Grant
    Filed: June 5, 1978
    Date of Patent: November 10, 1981
    Inventor: Jackson D. Leonard
  • Patent number: 4260813
    Abstract: Ethyl acetate and an excess of ethylene glycol monoethyl ether are subjected to ester-interchange reaction at a temperature not exceeding 100.degree. C. in the presence of a strongly acidic cation exchange resin as a catalyst. The resulting reaction mixture is distilled to recover the ethylene glycol monoethyl ether acetate formed. The unchanged reactants are recycled to the reaction zone for re-use, and the by-product ethanol is recovered in a highly pure form. This method can be continuously performed easily and effectively without the need to separate the catalyst or to employ complex distilling steps and without involving other difficulties.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: April 7, 1981
    Assignee: Showa Denko K.K.
    Inventors: Norio Kametaka, Kuniomi Marumo, Kiyonori Tokuda, Kazuo Sekiguchi
  • Patent number: 4251673
    Abstract: An organic ester e.g. 1,4-diacetoxybutane is hydrolyzed with an alkali metal or an alkaline earth metal hydroxide to a corresponding alcohol, the reaction being rapidly effected by having present a hydroxyl-containing compound. In a preferred embodiment, the hydroxyl-containing compound to be present is the very compound to be produced e.g. 1,4-butanediol is to be produced from 1,4-diacetoxybutane and there is present during the reaction of hydrolysis an earlier produced 1,4-butanediol.
    Type: Grant
    Filed: July 3, 1979
    Date of Patent: February 17, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Harold W. Mark, William V. Childs
  • Patent number: 4245122
    Abstract: A process is described for the preparation of allyl acetone (5-hexen-2-one) according to the reaction: ##STR1## wherein R is methyl or ethyl; X is chloro or bromo; M is sodium or potassium; and Q is sodium or potassium, the reaction being carried out (i) using a phase transfer agent and (ii) in a two phase system.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: January 13, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Denis E. Hruza, Sr., John B. Hall
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4218568
    Abstract: Formic acid is prepared by hydrolyzing methyl formate, the hydrolysis being carried out in the presence of from 0.5 to 3.0 moles, per mole of methyl formate, of a base which contains tertiary nitrogen atoms, boils at not less than 180.degree. C. under atmospheric pressure and has a pKa from 4 to 9, N-substituted imidazole derivatives being the preferred bases.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: August 19, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Hohenschutz, Johannes E. Schmidt, Hans Kiefer
  • Patent number: 4152530
    Abstract: A process for preparing allylic alcohols from allylic halides is provided by way of the intermediate formation of an ester in the presence of a water-insoluble ketone forming an azeotrope in water followed by saponification of the ester with alkali metal hydroxide, drying the alkali metal carboxylic acid salt formed during the saponification by azeotropic distillatiion with the ketone, thus obviating expensive separate recovery facilities and handling of the dried alkali metal carboxyolate salt. The overall process amounts to a hydrolysis of the allylic halide with aqueous alkali metal hydroxide and one reactor can serve for the whole process.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: May 1, 1979
    Assignee: Rhone-Poulenc Inc.
    Inventor: Peter S. Gradeff
  • Patent number: 4125735
    Abstract: A process for the synthesis of perfume products, Vitamin E and intermediates described herein involving a coupling reaction. For instance, a process for the synthesis of dehydrophytol and Vitamin E comprising forming a C.sub.15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C.sub.20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.
    Type: Grant
    Filed: October 16, 1975
    Date of Patent: November 14, 1978
    Assignee: SCM Corporation
    Inventors: Ralph E. Close, William Oroshnik
  • Patent number: 4117251
    Abstract: Straight-chain, primary alcohols are prepared by reacting straight-chain 1-bromoalkanes having 6 to 20 carbon atoms with alkali salts of monocarboxylic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of monocarboxylic acids or alcohols based upon the alkali salt of the carboxylic acid and at temperatures ranging from 150.degree. to 300.degree. C. The esters formed are saponified in alkaline medium to the straight-chain, primary alcohols and separated.
    Type: Grant
    Filed: March 17, 1977
    Date of Patent: September 26, 1978
    Assignee: Chemische Werke Huls AG
    Inventors: Manfred Kaufhold, Gottfried Bankwitz
  • Patent number: 4092368
    Abstract: A vapor phase process for preparing allylic alcohols which comprises reacting an allylic ester of a lower alkyl carboxylic acid with a lower alkanol in the presence of a zeolite transesterification catalyst.
    Type: Grant
    Filed: March 13, 1974
    Date of Patent: May 30, 1978
    Assignee: General Electric Company
    Inventor: William E. Smith