Preparing Esters From Ethers Patents (Class 560/240)
  • Patent number: 4691048
    Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: September 1, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
  • Patent number: 4677181
    Abstract: The present invention is directed to polyhydroxyl compounds containing both ether and ester groups, having an average hydroxyl functionality of 2 to 6 and an average hydroxyl number of about 100 to 600, based on the esterification product of (i) polyether polyols having an average hydroxyl functionality of 3 to 8 and an average hydroxyl number of about 200 to 1000 with (ii) about 5 to 70 equivalent %, based on the hydroxyl group of component (i) and the carboxyl group of component (ii), of organic monocarboxylic acids. The present invention is also directed to the use of the polyhydroxyl compounds as synthesis components in the production of polyurethane plastics materials by the isocyanate-polyaddition process, particularly their use as the polyol component in two-component polyurethane coating agents and/or polyurethane casting systems which are solvent-free or have a low solvent content.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: June 30, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Hohlein, Alois Fehlbier, Hermann Gruber
  • Patent number: 4665236
    Abstract: Alkylene oxide adducts of organic compounds having an active hydrogen are prepared by a process in which an active hydrogen reactant and an alkylene oxide reactant are reacted in the presence of a catalytically effective amount of one or more bimetallic oxo compounds of the formula (RO).sub.n M--O--M'--O--M(OR).sub.n, wherein each R is (independently) an optionally-substituted organic moiety, M' is a divalent metal selected from the elements of Groups VIII, Ib, IIb, IIIb, and IVb of the Periodic Table, each M is (independently) a trivalent or tetravalent metal, and each n is 2 if the adjacent M is trivalent of 3 if the adjacent M is tetravalent. The products are useful, for instance, as nonionic surfactants in detergent formulations. In certain preferred embodiments, the process yields a product having a very desirable distribution of alkylene oxide adducts.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: May 12, 1987
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 4665094
    Abstract: Hydroxyalkyl-phenoxy-propan-2-olamines and novel esters thereof are oculoselective .beta.-blockers useful in the treatment of elevated intraocular pressure with little or no effect on the pulmonary or cardiovascular system.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: May 12, 1987
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • Patent number: 4659865
    Abstract: A process for producing ethylidenediacetate which comprises reacting methyl acetate or dimethyl ether, carbon monoxide and hydrogen in the presence of catalyst comprising as a secondary-component at least one material selected from the group consisting of, iodides and bromides and as a main component combination of (1) at least one material selected from the group consisting of nickel and nickel compounds, at least one material selected from the group consisting of cobalt and cobalt compounds under substantially anhydrous conditions is disclosed. According to the present invention synthesis of ethylidenediacetate is achieved by using a cheaper catalyst than the prior catalyst.
    Type: Grant
    Filed: July 30, 1984
    Date of Patent: April 21, 1987
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi, Takayuki Yasunaga
  • Patent number: 4654174
    Abstract: The invention disclosed herein is a process for preparing aliphatic anhydrides comprising contacting a divinyl ether with carboxylic acid in the presence of a catalytic amount of a strong acid. The invention is further a process for preparing alkylidene dicarboxylates, which are intermediates in the above preparation of aliphatic anhydride.
    Type: Grant
    Filed: May 28, 1982
    Date of Patent: March 31, 1987
    Assignee: The Dow Chemical Company
    Inventors: James A. Kaufman, Suzanne V. McKinley
  • Patent number: 4640802
    Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.
    Type: Grant
    Filed: July 7, 1982
    Date of Patent: February 3, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4603219
    Abstract: The compounds 9-(1,3-dihydroxy-2-propoxymethyl)guanine and the pharmaceutically acceptable salts thereof are useful as antiviral agents. The compound 1,3-dibenzyloxy-2-acetyloxy-methoxypropane is useful as an intermediate for the preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine.
    Type: Grant
    Filed: October 29, 1984
    Date of Patent: July 29, 1986
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Julien P. H. Verheyden, John C. Martin
  • Patent number: 4590294
    Abstract: The invention relates to the use of hydrogen ion-exchanged layered clays in organic reactions which are catalyzed by protons. Such organic reactions include the production of ethers by the reaction of an alcohol with an olefin or an olefin oxide, the production of an ether by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of an alkyl aromatic compound by the reaction of an aromatic hydrocarbon with an olefin or a C.sub.2 or higher alcohol and the production of an alcohol by the hydration of an olefin.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 20, 1986
    Assignee: The British Petroleum Company Limited
    Inventors: James A. Ballantine, Reginald Gregory, John H. Purnell, John M. Thomas, David J. Westlake
  • Patent number: 4585592
    Abstract: In polyoxybutylene polyoxyalkylene glycols obtained by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen and under the catalytic action of a bleaching earth, the content of oligomeric cyclic ethers is reduced by distillation under reduced pressure at above 200.degree. C. after first treating the copolymer with oxygen or an oxygen-containing gas (air) at a temperature of from 20.degree. to 110.degree. C.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: April 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4568774
    Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: February 4, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4564671
    Abstract: Polyoxybutylene polyoxyalkylene glycols are prepared by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen, by a continuous process in which the polymerization is carried out in a reactor over a fixed-bed clay catalyst and with recycling of the reaction mixture, and less than 30% by weight, based on the reaction mixture to be recycled, of a mixture of tetrahydrofuran, 1,2-alkylene oxide and a compound containing reactive hydrogen is added to the reaction mixture, which is recycled to the reactor after flowing through the latter.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: January 14, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4559177
    Abstract: A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: December 17, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tetsuya Okutani, Giichi Goto
  • 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: 4518797
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4499298
    Abstract: A process is described for the preparation of aryl esters such as benzyl acetate by reacting an aryl alkyl compound such as toluene with a carboxylic acid such as acetic acid and oxygen in the presence of a catalytically effective amount of a catalyst comprising palladium metal, gold metal and a metal of Group VA of the Periodic Table of the Elements such as bismuth.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: February 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: John A. Scheben, James A. Hinnenkamp
  • 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: 4472294
    Abstract: A fluorine-containing compound of the formula: ##STR1## wherein Rf is a C.sub.3 -C.sub.21 fluorine-containing group; R is a hydrogen atom or a C.sub.1 -C.sub.4 acyl group; Q is an aliphatic or aromatic hydrocarbon group having not more than twenty-one carbon atoms; and n is an integer of 1 to 10 lowers the surface tensions of water and/or organic liquids and the interfacial tensions between them.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: September 18, 1984
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Iwao Hisamoto, Chiaki Maeda, Mitsuhiro Nishiwaki
  • Patent number: 4466922
    Abstract: 3-Alkyl-3-acyloxy-4-hydroxybut-1-enes are prepared by a process in which a 3-alkyl-3,4-epoxybut-1-ene is treated with a carboxylic acid and a copper salt of a carboxylic acid.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: August 21, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Rolf Fischer
  • Patent number: 4310465
    Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: January 12, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Gary L. Olson, Gabriel Saucy
  • 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: 4298758
    Abstract: Propylene glycol and dipropylene glycol diesters are prepared by reacting dichloropropyl ethers with a carboxylic acid salt, e.g., sodium acetate, and the corresponding carboxlyic acid, e.g., acetic acid. The by-product sodium chloride is insoluble in the acetic acid and easily separated from the reaction mixture. The diesters can be hydrolyzed to their respective glycols.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: November 3, 1981
    Assignee: The Dow Chemical Company
    Inventors: Frank T. Cook, Donald G. Prier
  • Patent number: 4296042
    Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.
    Type: Grant
    Filed: June 18, 1980
    Date of Patent: October 20, 1981
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Michael C. Venuti
  • Patent number: 4288614
    Abstract: A novel process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol which employs as starting materials 2-substituted-3-methyl-6-alkoxy-3,6-dihydro-2H-pyrans. Novel intermediates are also disclosed.
    Type: Grant
    Filed: February 6, 1980
    Date of Patent: September 8, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Gary L. Olson
  • Patent number: 4273934
    Abstract: 3-Hydroxy-2,2,4-trimethylpentyl isobutyrate is prepared by reaction of isobutyraldehyde in the presence of an alkaline earth metal hydroxide and of carboxylic acids or the corresponding salts, under specific conditions in respect of reaction time and proportion and concentration of the hydroxide suspension. The product is a starting material for the preparation of dyes, pesticides, adhesives and surface coatings.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Hans-Juergen Foerster
  • Patent number: 4267363
    Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: May 12, 1981
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4263443
    Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.
    Type: Grant
    Filed: November 22, 1978
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: John F. White
  • Patent number: 4259531
    Abstract: Polytetramethylene ether glycols with molecular weights of from 300 to 4500 are produced by polymerizing tetrahydrofuran with an adduct of antimony pentachloride with carboxylic acids or carboxylic acid esters as the catalyst in the presence of a carboxylic acid anhydride, e.g., acetic anhydride, as the promoter. Esterified, e.g., acetylated, polytetramethylene ether glycols produced are subsequently converted to polytetramethylene ether glycols by saponification or transesterification. The process causes substantially less environmental pollution than do prior art methods, yet it is both economical and flexible.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: March 31, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Otto H. Huchler, Walter Mesch, Siegfried Winderl, Herbert Mueller, Herwig Hoffmann
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4258205
    Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4252738
    Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.
    Type: Grant
    Filed: March 17, 1978
    Date of Patent: February 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Willy Hartmann, Hans-Georg Heine
  • Patent number: 4252935
    Abstract: Esters of glycidyl polyethers of saturated phenols are especially useful in coating compositions having a low organic solvent content. The esters are the reaction products of from about 0.5 to about 1.5 equivalents of a saturated monocarboxylic acid with each epoxy group in a diglycidyl polyether of phenols where the aromatic rings of the phenols are saturated.
    Type: Grant
    Filed: July 31, 1979
    Date of Patent: February 24, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Carl C. Anderson, William J. Birkmeyer, Roger M. Christenson, Rostyslaw Dowbenko, Ronald J. Lewarchik
  • Patent number: 4243799
    Abstract: A process for the preparation of polybutylene glycol carboxylic acid diesters of the formulaR--CO--O--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --O).sub.n CO--R.sup.1by polymerizing pretreated tetrahydrofuran in the presence of one or more carboxylic acids and/or carboxylic acid anhydrides and of a polymerization catalyst, especially antimony pentachloride or a bleaching earth containing less than 3% by weight of water, wherein the tetrahydrofuran is treated with a strong mineral acid, an organic sulfonic acid, silica gel and/or a bleaching earth prior to the polymerization.
    Type: Grant
    Filed: May 18, 1979
    Date of Patent: January 6, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Mueller, Otto H. Huchler, Herwig Hoffmann
  • Patent number: 4229592
    Abstract: The compound of the formula ##STR1## has been found to be an important and practical intermediate with the proper stereo-isomerism for the preparation of numerous prostaglandin derivatives. It can easily be converted to 4.alpha.-acetoxy-2-cyclopentenone by a variety of processes.
    Type: Grant
    Filed: February 6, 1978
    Date of Patent: October 21, 1980
    Assignee: Kansas University Endowment Association
    Inventors: Lester A. Mitscher, George W. Clark, III, Paul B. Hudson
  • Patent number: 4223160
    Abstract: Niobium and ruthenium salts are employed as catalyst in the reaction of oxirane compounds with carboxylic acids. The acrylate esters produced can be used in photocurable compositions.
    Type: Grant
    Filed: March 26, 1979
    Date of Patent: September 16, 1980
    Assignee: Union Carbide Corporation
    Inventor: Lawrence G. Hess
  • Patent number: 4214099
    Abstract: A new synthesis of key prostaglandin precursors and intermediates employed in their preparation. The novel synthetic sequence of this invention is shorter and more efficient than those previously employed to prepare to key intermediate.
    Type: Grant
    Filed: June 22, 1978
    Date of Patent: July 22, 1980
    Assignee: Pfizer Inc.
    Inventors: Elias J. Corey, Jasjit S. Bindra, Thomas K. Schaaf
  • Patent number: 4175204
    Abstract: E-4-acetoxy-2-methyl-2-butenal is prepared by: (1) preparation of an intermediate allylic halide from isoprene; and (2) reaction of the allylic halide with dimethyl sulfoxide in the presence of a non-nucleophilic base to form the desired product.
    Type: Grant
    Filed: January 8, 1979
    Date of Patent: November 20, 1979
    Inventor: James H. Babler
  • Patent number: 4171375
    Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, R.sup.2 represents hydrogen or alkyl of 1 through 12 carbon atoms, and n represents an integer from 4 through 8, are new compounds possessing pharmacological properties, more particularly the production of hypertension and inhibition of gastric acid secretion. They are also useful in the preparation of 10-hydroxyprostaglandins.
    Type: Grant
    Filed: January 12, 1977
    Date of Patent: October 16, 1979
    Assignee: May & Baker Limited
    Inventors: Michael P. L. Caton, Trevor Parker, Gordon L. Watkins
  • Patent number: 4163115
    Abstract: Esters of poly(tetramethylene ether) glycol are prepared by polymerizing tetrahydrofuran in a reaction mixture which contains, in addition to the tetrahydrofuran, and acylium ion precursor such as acetic anhydride, a polymeric catalyst which contains sulfonic acid groups and, optionally, a carboxylic acid such as acetic acid.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: July 31, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: George E. Heinsohn, Ivan M. Robinson, Gerfried Pruckmayr, Walter W. Gilbert
  • Patent number: 4153805
    Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.
    Type: Grant
    Filed: September 29, 1977
    Date of Patent: May 8, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4131739
    Abstract: Cyclic acetals are rearranged to form isomeric carboxylic acid esters according to the following formula: ##STR1## wherein R is an alkyl, alkenyl, or aromatic moiety containing 1 to 12 carbon atoms;AndR' is an alkyl or alkenyl moiety containing 1 to 12 carbon atoms;In the presence of a catalyst consisting of a metal selected from the group Ru, Rh, Pd, Os, Ir or Pt supported on carbon.
    Type: Grant
    Filed: July 11, 1977
    Date of Patent: December 26, 1978
    Assignee: Eastman Kodak Company
    Inventor: Don L. Morris
  • Patent number: 4110539
    Abstract: This invention describes a process for the synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate by the acid catalyzed cleavage and esterification of 2,4-diisopropyl-5,5-dimethylmetadioxane.
    Type: Grant
    Filed: July 13, 1977
    Date of Patent: August 29, 1978
    Assignee: Eastman Kodak Company
    Inventors: Kenneth H. Albers, Howard N. Wright, Jr.
  • Patent number: 4092339
    Abstract: Homopolymers and copolymers of glycidyl esters are made by reacting the acids to be esterified with the corresponding polymer of tert.-alkyl glycidyl ether under substantially anhydrous conditions and in the presence of a strong acid catalyst, preferably a sulfonic acid. The reaction proceeds satisfactorily at about 100.degree.14 150.degree. C with displacement of the tert.-alkyl group by the acyl group of the acid and evolution of tert.-olefin. By use of the appropriate proportion of reactant acid and/or appropriate reaction time, any desired proportion of the glycidyl groups can be esterified.
    Type: Grant
    Filed: November 19, 1975
    Date of Patent: May 30, 1978
    Assignee: The Dow Chemical Company
    Inventors: Violete L. Stevens, Arthur R. Sexton, Frederick P. Corson
  • Patent number: 4087453
    Abstract: A process for recovering monomeric glycols and glycerine from polyoxyalkylene glycols and polyglycerines which comprises heating the polymeric compounds together with a lower saturated mono-carboxylic acid, containing from 2 to 4 carbon atoms such as acetic acid, in the presence of a strong acid, e.g. sulfuric acid, or a strong acid cation exchange resin. The product, which is the diester of the monomeric glycol or the triester of glycerine, is recovered and subsequently hydrolyzed to obtain the desired monoglycol or glycerine product. If it is desired to obtain the ester itself, the latter step of hydrolyzing can be omitted.
    Type: Grant
    Filed: June 18, 1976
    Date of Patent: May 2, 1978
    Assignee: The Dow Chemical Company
    Inventors: Fred A. Sherrod, William L. Howard, Joanne D. Burger
  • Patent number: 4069242
    Abstract: A synergistic catalytic effect is realized in the esterification reaction between an organic carboxylic acid and a vicinal epoxide by using a catalyst system comprising: (a) a compound containing an amino and/or ammonium nitrogen atom, in combination with (b) a soluble compound containing an ionizable atom of iron or chromium.
    Type: Grant
    Filed: September 9, 1971
    Date of Patent: January 17, 1978
    Assignee: The Dow Chemical Company
    Inventor: Arthur E. Gurgiolo
  • Patent number: 4069385
    Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.
    Type: Grant
    Filed: June 3, 1976
    Date of Patent: January 17, 1978
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Araki, Tsuneyuki Nagase
  • Patent number: 4068082
    Abstract: Esters are prepared by reaction of acyl halides and alcohols or hydroxyalkyl esters and acid halides in the presence of a tertiary amine and polar aprotonic solvents. Bis(2-methacrylatoethyl) phthalate is prepared by the reaction of phthaloyl chloride with 2-hydroxyethyl methacrylate in pyridine and acetone. Bis-phenol-A-bis(2-methacrylatoethyl)ether is prepared from 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane and methacryl chloride in acetone.
    Type: Grant
    Filed: September 19, 1973
    Date of Patent: January 10, 1978
    Assignee: Lee Pharmaceuticals
    Inventors: Donald G. Stoffey, Jan Alexander Orlowski
  • Patent number: 4052424
    Abstract: This invention provides a process for producing carboxylic esters in high yield by contacting alkanol in vapor phase with a novel silver-cadmium alloy catalyst.
    Type: Grant
    Filed: September 1, 1976
    Date of Patent: October 4, 1977
    Assignee: Celanese Corporation
    Inventor: Thomas H. Vanderspurt