Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
  • Patent number: 4668816
    Abstract: High yields of aromatic, aromatic acetic and olefinic acids, esters, amides and the like are derived from a process wherein a halo-hydrocarbon is carbonylated in the presence of a palladium catalyst, a hindered amine base and phosphine in excess. The hindered amine base can comprise C.sub.3 -C.sub.10 branched alkyls, cyclic compounds, or mixtures of the above. The preferred amine is N,N-diisopropylethyl amine. The preferred catalyst is PdCl.sub.2 (PPH.sub.3).sub.2 with the excess phosphine generally supplied by a compound of the formula PR.sup.1 R.sup.2 R.sup.3 where R.sup.1, R.sup.2 and R.sup.3 are preferably phenyl.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: May 26, 1987
    Assignee: Stauffer Chemical Company
    Inventor: Ronald A. Epstein
  • Patent number: 4668702
    Abstract: Pesticidal compounds have the formula: ##STR1## wherein D represents hydrogen or a cyano groupX represents chlorine or bromineA represents an alkyl groupn is 0 or an integer of 1-4 andRCOO is the residue of an acid RCOOH whose .alpha.-cyano-3-phenoxybenzyl ester has pesticidal properties. They are prepared by esterification methods.
    Type: Grant
    Filed: January 30, 1986
    Date of Patent: May 26, 1987
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Richard L. Elliott
  • Patent number: 4668701
    Abstract: A compound of formula I: ##STR1## in which formula: D represents hydrogen or a cyano group;X represents halogen;A represents an alkyl group (typically a C.sub.1 -C.sub.6 alkyl group);n is 0 to 4;RCOO. represents a residue of an acid RCO.sub.2 H, which acid, or an ester-forming derivative of which acid, on reaction with .alpha.-cyano-3-phenoxybenzyl alcohol or an ester-forming derivative thereof, gives rise to an .alpha.-cyano-3-phenoxybenzyl ester having pesticidal properties.
    Type: Grant
    Filed: January 30, 1986
    Date of Patent: May 26, 1987
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Richard L. Elliott
  • Patent number: 4667056
    Abstract: A process for preparing hydratropic acids and the esters thereof, of formula Ar--CH(CH.sub.3)--COOR where R=H or lower alkyl and Ar=phenyl possibly substituted. This process consists in reacting on the propiophenones of formula ArCOCH.sub.2 CH.sub.3, a chlorinating or brominating agent, an alcohol R'OH where R'=lower alkyl, an orthoester R.sub.1 --C(OR').sub.3 wherein R.sub.1 =H or lower alkyl, and metal zinc; then possibly hydrolyzing the esters obtained.With this process can be prepared hydratropic acids known for their anti-inflammatory activity.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: May 19, 1987
    Assignee: Delalande S.A.
    Inventor: Guy P. Adrian
  • Patent number: 4664851
    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, 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 transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: May 12, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4665213
    Abstract: Carboxylic acid esters are produced by reacting an olefinic hydrocarbon with an ester of formic acid in the presence of both carbon monoxide and oxygen at a temperature of up to 200.degree. and a pressure of up to 300 bar in the presence of water, typically in an amount of from 0.01 to 5% w/w, a source of protons, which is preferably a mineral acid or a tectometallosilicate in the hydrogen form, and as catalyst (a) a source of palladium, and (b) a source of copper.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: May 12, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4661619
    Abstract: Carboxylic acids and/or esters thereof are produced by reacting either a benzylic or an aromatic mercaptan with carbon monoxide and either water or an aqueous alcohol at elevated temperature, suitably in the range from 100.degree. to 300.degree. C., in the presence as catalyst of a cobalt carbonyl, the product using water as the reactant being a carboxylic acid and using aqueous alcohol as the reactant a carboxylic acid ester, mixtures of acids and esters being formed using aqueous alcohols having high water concentrations.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: April 28, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, Sang C. Shim, David J. H. Smith
  • Patent number: 4656214
    Abstract: Novel compounds are provided which have been found to be particularly useful as stain resistant plasticizers. These plasticizers impart improved low temperature flexibility to the plasticized compositions. In addition, the novel plasticizers of this invention have been found to provide plastisols and organosols of low viscosity, which is a very advantageous property for plastisols and organosols intended for use in the manufacture of vinyl sheet floorings since it enables a reduction in the amount of volatile solvent normally employed.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: April 7, 1987
    Assignee: Exxon Research & Engineering Co.
    Inventor: Edward J. Wickson
  • Patent number: 4649213
    Abstract: Compounds having anti-inflammatory and analgesic activity of the formula ##STR1## are produced from compounds having the formula ##STR2## by rearrangement in the presence of a base or an amide and (1) X S O X.sup.1 or X S O.sub.2 X.sup.1 where X and X.sup.1 are halogen or trifluoromethyl or (2) sulfur dioxide and halogen.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: March 10, 1987
    Assignee: Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shun-ichi Ikeda, Kenji Nakao, Kentaro Tamaki
  • Patent number: 4647691
    Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4642370
    Abstract: Carboxylic acid esters are produced by reacting (i) carbon monoxide, (ii) a compound of the formula M(OR).sub.x wherein M is either boron, silicon, aluminum, titanium or zirconium, x is the valency of M and R is a hydrocarbyl group and (iii) a hydrocarbyl halide, wherein the halide moiety is bromide, chloride or iodide, in the presence of a catalyst comprising one or more of the metals rhodium, iridium and cobalt in either elemental or compound form. When M is boron, silicon or aluminum and the halide moiety is chloride, there is preferably added a source of iodide.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: February 10, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith, James B. Woell
  • Patent number: 4642382
    Abstract: The title compounds correspond to the formula ##STR1## and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.
    Type: Grant
    Filed: July 18, 1985
    Date of Patent: February 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor, Paul Odorisio
  • Patent number: 4640706
    Abstract: Novel cyclohexenonecarboxylic acid derivatives exhibit herbicidal and plant growth regulating activity.The cyclohexenonecarboxylic derivatives are of the formula I ##STR1## wherein A is an aliphatic or aromatic alcohol, or is an amino group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano, or is a heterocyclic amino group which is unsubstituted or substituted,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,B is an aliphatic or aromatic radical or is an aliphatic or aromatic carbonyl or sulfonyl group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano.The compounds are suitable for selectively controlling grasses in crops of useful plants.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: February 3, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • 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: 4628113
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising cobalt in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: December 9, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4627933
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4626276
    Abstract: Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cycloh exane-1,3-diones and derivatives thereof. The compounds can be prepared via oxidation of the corresponding 5-(substitutedthioalkyl) precursors. The compounds are especially useful as selective herbicides active against grassy weeds.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: December 2, 1986
    Assignee: Chevron Research Company
    Inventor: Tatao Luo
  • Patent number: 4625049
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising nickel in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: November 25, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4623736
    Abstract: In preparing arylalkanoic acids, e.g. ibuprofen or naproxen, via the conversion of the selected .alpha.-haloketal derivative of a 1-haloethyl aryl ketone to the haloalkyl ester of the arylalkanoic acid using a zinc salt catalyst the improvement comprising reacting a ring-substituted 6-membered ring ketal of the selected 1-haloethyl C.sub.6 -C.sub.12 -aryl ketone with a soluble zinc carboxylate salt to form the corresponding 3-haloalkyl arylalkanoic acid ester. The ester is converted to the alkali metal salt of the acid with base in an aqueous/water insoluble organic liquid mixture and the crude salt is converted to the corresponding acid in an aqueous/water insoluble solvent mixture for the acid, the organic solution of the acid is washed with a pH 7.0 to 8.
    Type: Grant
    Filed: July 9, 1982
    Date of Patent: November 18, 1986
    Assignee: The Upjohn Company
    Inventors: Jerry A. Walker, Sanjay I. Amin
  • Patent number: 4622163
    Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein. The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: November 11, 1986
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4618697
    Abstract: This invention relates to a process for preparing an alpha-arylalkanoic acid or salt thereof which comprises the rearrangement of an alpha-halo-alkylarylketal in neutral or slightly alkaline conditions, in the presence of a dipolar aprotic diluent and of a protic substance having a high dielectric constant, and the subsequent hydrolysis of the thus obtained ester.
    Type: Grant
    Filed: February 3, 1984
    Date of Patent: October 21, 1986
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4618705
    Abstract: Carboxylic acid anhydrides are reacted with hydrogen to produce alkylidene diesters with high yield and with ratios of alkylidene diesters and co-product carboxylic acid near the theoretical by carrying out the reaction in the presence of a cobalt carbonyl.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: October 21, 1986
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4614816
    Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.
    Type: Grant
    Filed: October 13, 1983
    Date of Patent: September 30, 1986
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, Peter S. Williams
  • Patent number: 4611010
    Abstract: Halovinylbenzyl esters of the formula I ##STR1## where R.sup.1 is ##STR2## R.sup.2 is H, CN, lower alkyl, lower alkenyl, lower alkynyl, lower haloalkyl or lower haloalkenyl, R.sup.3 is H, halogen or lower alkyl, R.sup.4 is H, lower alkyl, lower alkoxy or lower alkoxymethyl, R.sup.5 is lower alkyl, lower hal lk(en)yl or lower haloalkynyl, R.sup.6 and R.sup.7 are each lower alkyl or halogen, A is halogen, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, CN or NO.sub.2, m is 0 to 4, n is 1 to 3, B is lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl, and X is H, halogen, lower haloalkyl, lower thioalkyl, lower alkoxy or lower alkyl, and halogen can be fluorine, chlorine or bromine and, in the case of R.sup.2, may furthermore be iodine, a process for their manufacture, and their use as pesticides.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: September 9, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd-Ulrich Schwarz, Hans Theobald, Heinrich Adolphi
  • Patent number: 4609673
    Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: September 2, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4602092
    Abstract: A method is provided for preparing phosphinic acid prodrug intermediates which are useful in preparing phosphinic acid angiotensin-converting enzyme inhibitors which method includes the step of coupling a phosphonous acid or its ester of the structure ##STR1## wherein R is H or lower alkyl and R.sup.1 is lower alkyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl, with an alkylating agent of the structure ##STR2## wherein Hal is Cl, Br or I, n is 0 or 1, R.sup.2 is H or lower alkyl, and Z is H, lower alkyl, --CO.sub.2 R.sup.3 (wherein R.sup.3 is H or lower alkyl), ##STR3## (wherein R.sup.4 is H, lower alkyl, aryl or arylalkyl), --CN, or ##STR4## (wherein R.sup.5 and R.sup.6 may be the same or different and are selected from the group consisting of H, lower alkyl, aryl, aryl-lower alkyl, cycloalkyl or cycloalkylalkyl and at least one of R.sup.5 and R.sup.6 is other than H, or R.sup.5 and R.sup.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: July 22, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: John K. Thottathil, Jerome L. Moniot
  • Patent number: 4602105
    Abstract: A process for the preparation of alpha-haloalkylesters, wherein an acylhalide having the general formula ##STR1## in which R.sup.1 represents a substituted or unsubstituted hydrocarbyl group and Hal represents chlorine or bromine is contacted with hydrogen at elevated temperature and pressure in the presence of a catalytic system comprising at least one Group VIII element.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4592858
    Abstract: A liquid crystal compound of the formula: ##STR1## wherein R.sup.1 is an alkyl group, X is chloro or bromo, and R.sup.2 is a branched-alkyl group; and the carbon atom marked with an * is an asymmetric carbon atom.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: June 3, 1986
    Assignee: Ajinomoto Company, Inc.
    Inventors: Ryoichi Higuchi, Masao Honma, Takao Sakurai, Naoko Mikami
  • Patent number: 4593115
    Abstract: An 1-Iodoalkyl acylate, which is useful as the raw material for esterification of cephalosporins, penicillins, etc. is prepared in a high degree of purity and in high yield by (1) allowing a carboxylic acid iodide to react with an aldehyde, or (2) allowing a carboxylic acid chloride to react with a salt of hydriodic acid and then allowing the resulting product to react with an aldehyde, or (3) by simultaneously allowing a carboxylic acid chloride, a salt of hydriodic acid and an aldehyde to react with one another.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: June 3, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Masayoshi Yamaoka
  • Patent number: 4592870
    Abstract: This invention produces methyl esters and ethylene glycol esters by reacting carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and an acyl compound. Methyl ester and ethylene glycol ester are the predominant products. These esters are used as precursors in the formation of ethylene glycol, vinyl acylates such as vinyl acetate, ethylene oxide, ethylene carbonate and methanol.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: June 3, 1986
    Assignee: Union Carbide Corporation
    Inventor: Bernard D. Dombek
  • Patent number: 4589992
    Abstract: Salts having the formula:Y--NH.sub.3.sup.+.RCO.sub.2.sup.- Iin which Y is a group of formula R.sup.1 XCH.sub.2 CH(OH)CH.sub.2 --, R and R.sup.1 are the same or different and each is a straight- or branched chain alkyl group having from 1 to 18 carbon atoms, a straight- or branched chain alkenyl group having from 2 to 18 atoms, a cycloalkyl group having from 4 to 12 ring atoms, an aryl group having 6-10 ring atoms, or an aralkyl group having from 7 to 10 carbon atoms; and X is O, CO.sub.2, NR.sup.2 or S and R.sup.2 is hydrogen, a straight- or branched chain alkyl group having from 1 to 18 carbon atoms or an alkenyl group having from 2 to 18 C atoms.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: May 20, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Emyr Phillips, David Wilson
  • Patent number: 4575561
    Abstract: Aryl-substituted acetic acid esters are directly prepared by carbonylation of benzyl halides under one atmosphere of carbon monoxide at ambient temperature in alcohol solvent using as catalyst dicobalt octacarbonyl and a base-alumina as co-reactant.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: March 11, 1986
    Assignee: Texaco Inc.
    Inventor: Robert A. Sawicki
  • Patent number: 4570006
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsine, anti-plasmin, anti-kallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
  • Patent number: 4567293
    Abstract: A novel compound of 2-[para-(2-substituted or unsubstituted-3,3,3-trifluoropropyl)phenyl]propionic acid or a salt thereof which has a specific pharmacological activity and a pharmaceutical composition comprising the novel compound as an active ingredient are disclosed.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: January 28, 1986
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Takashi Yamauchi, Akira Iizuka
  • Patent number: 4564698
    Abstract: The present invention relates to new tricyclic compounds of the formula: ##STR1## having valuable CNS and cardiovascular properties.
    Type: Grant
    Filed: January 24, 1983
    Date of Patent: January 14, 1986
    Assignee: Akzo N.V.
    Inventors: Johannes H. Wieringa, Frans A. van der Vlugt
  • Patent number: 4558153
    Abstract: Carboxylic acids having two or more carbon atoms than formic acid, or esters of such carboxylic acids are prepared by reacting either formic acid or an ester of formic acid with an olefin at elevated temperature in the presence of a Group VIB metal catalyst. The Group VIB metal which is chromium, molybdenum or tungsten is suitably added as a carbonyl or carbonyl halide. In addition to the catalyst a halide promoter and a phosphorus containing copromoter may optionally be added. The process can be used, for example to prepare propionic acid or a propionic acid ester from ethylene and either formic acid of an ester of formic acid.
    Type: Grant
    Filed: October 23, 1984
    Date of Patent: December 10, 1985
    Assignee: BP Chemicals Limited
    Inventor: John Cook
  • Patent number: 4546200
    Abstract: 2,2-Dinitrobutane-1,4-diol and 4-monoesters thereof.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: October 8, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, Horst G. Adolph
  • Patent number: 4546198
    Abstract: Stereoisomerically-enriched esters are prepared by treating a non-symmetrical ketene with a racemic or chiral tertiary-base-substituted alkylcarbinol. Optional hydrolysis of the esters gives the corresponding optically-active carboxylic acids corresponding to the non-symmetrical ketene.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: October 8, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4544766
    Abstract: This invention relates to a process for preparing an aryl acetic acid derivative represented by the formulaAr--CH.sub.2 COY).sub.ncomprising hydrolyzing in an alkaline substance a dichloroethenyl compound represented by the formulaAr--CH.dbd.CCl.sub.2).sub.n.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: October 1, 1985
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventor: Tatsuya Shono
  • Patent number: 4544767
    Abstract: Hydrogenation of an acyloxyolefin is effected in the presence of at least one of an alkali and an alkaline earth metal salt of a carboxylic acid. In one embodiment, 1,4-diacetoxy-2-butene is converted to 1,4-diacetoxybutane employing potassium acetate.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: October 1, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Kiplin D. Cowan
  • Patent number: 4541944
    Abstract: Hydrogen peroxide and persalt washing or disinfecting compositions perform comparatively ineffectively at ambient to low operating temperatures. More effective washing/disinfection processes are obtained by employing according to the instant invention there with a peroxyacid generator selected from compounds having the general formula (I): ##STR1## in which R.sub.1 and R.sub.2 and R.sub.3 often are hydrogen, R.sub.6 is often hydrogen or methyl and R.sub.4 and R.sub.5 are often methyl or phenyl. R.sub.3 or R.sub.5 can each also represent a difunctional group terminating at its other end in a second gem-diester group or in an enol ester group. Especially preferred peroxyacid generators include 1,1,5-triacetoxypent-4-ene, 1,1,5,5-tetraacetoxy pentane, the corresponding butene and butane compounds, ethylidene benzoate acetate and bis(ethylidene acetate) adipate.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: September 17, 1985
    Assignee: Interox Chemicals Limited
    Inventor: William R. Sanderson
  • Patent number: 4542220
    Abstract: The invention relates to a process for the preparation of derivatives of dichloroacetic acid esters, by reaction of a glyoxylic acid ester having the general formula R.sub.1 --CO--COOR.sub.2, wherein R.sub.1 represents an optionally substituted aryl or heteroaryl group and R.sub.2 an alkyl, cycloalkyl or aryl group, with phosphoruspentachloride in the presence of a dispersant suitable for distributing the phosphoruspentachloride.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: September 17, 1985
    Assignee: Stamicarbon B.V., Licensing Subsidiary of DSM
    Inventors: Antonius Corvers, Joannes M. C. A. Mulders
  • Patent number: 4542237
    Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer
  • Patent number: 4540810
    Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: September 10, 1985
    Assignee: Texaco Development Corporation
    Inventor: John F. Knifton
  • Patent number: 4539420
    Abstract: A manufacturing method is described for the preparation of optically active 1-aromatic-group-substituted-1-alkanones characterized in that an optically active alkane acid halide is allowed to react with an aromatic compound in the presence of a Lewis acid. The optically active 1-aromatic-group-substituted-1-alkanones are useful intermediates in the preparation of optically active alpha-arylalkanoic acids, which are useful as pharmaceutical, e.g. anti-inflammatory, analgesic and anti-pyretic, agents and as insecticidal agents.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: September 3, 1985
    Assignee: Syntex Pharmaceuticals International Limited
    Inventors: Gen-Ichi Tsuchihashi, Shuichi Mitamura, Koji Kitajima
  • Patent number: 4539421
    Abstract: The title compounds correspond to the formula ##STR1## and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: September 3, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor, Paul Odorisio
  • Patent number: 4537713
    Abstract: The invention concerns a process for the reduction of groups containing unsaturated C,C--, C,N--,N,N--,N,O-- bonds, especially of NO.sub.2 --,NO--,NOH--,NR--,CN--,N.sub.3 --,N.sub.2 -groups or C.dbd.C or C-halogen- or acyl groups with hydrogen on MPc or with a suitable reduction agent on [MPc].sup..crclbar., whereby a platinum metal-phthalocyanine is used as the catalyst. It is possible that by the reversible change (control) of the oxidation phase z of the platinum metal from z.gtoreq.2 to z.ltoreq.1 using the same MPc complex, basically different reductions can be selectively catalysed.Thus the invention concerns a process for selective reduction using platinum metal-phthalocyanine catalysts with reaction specificity in three different reaction patterns.The inventive process is suitable, especially for the synthesis of .alpha.-phenylalkylamines, benzylalkylamines, N-alkyl-amino carboxylic acids, .alpha.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: August 27, 1985
    Inventor: Heiner Eckert