Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4946845Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.Type: GrantFiled: November 25, 1988Date of Patent: August 7, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: D. V. Krishna Murthy, Michael C. Venuti, John M. Young
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Patent number: 4945179Abstract: Process for the preparation of esters of carboxylic acids by contacting an olefinically unsaturated compound with CO and an alcohol, in the presence of (a) a ruthenium compound and (b) an iodide salt, LiBr and/or an onium bromide, with a molar ratio of CO to olefinically unsaturated compound.ltoreq.2.0 being applied when "b" is an iodide salt.Type: GrantFiled: August 15, 1988Date of Patent: July 31, 1990Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4940813Abstract: A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.Type: GrantFiled: March 31, 1989Date of Patent: July 10, 1990Assignee: Merck & Co., Inc.Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
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Patent number: 4911732Abstract: Improved light fastness of dyeings on textile polyester material with disperse dyes is obtainable by dyeing in the presence of certain benzophenone ether esters, some of which are novel.Type: GrantFiled: September 28, 1988Date of Patent: March 27, 1990Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Dieter Wegerle, Reinhold Krallmann
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Patent number: 4902814Abstract: A compound of formula: ##STR1## wherein R is selected from hydrogen, cyano, methyl, and ethynyl, and X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol. The compounds are useful as insecticides and acaricides.Type: GrantFiled: July 2, 1987Date of Patent: February 20, 1990Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4886619Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.Type: GrantFiled: May 29, 1987Date of Patent: December 12, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Eugene P. Janulis
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Patent number: 4885383Abstract: A process for the preparation of methyl carboxylates by the reaction of mono or dicarboxylic acids having more than 5 carbon atoms and methanol in the presence of acidic catalysts at temperatures from 100.degree. to 150.degree. C. and below the boiling point of the carboxylates being produced.Type: GrantFiled: September 23, 1988Date of Patent: December 5, 1989Assignee: Hoeschst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer, Peter Lappe
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Patent number: 4883613Abstract: The compounds 9-phenyl-3,7-dimethyl-2,4,6,8 nonatetraenoic acids wherein the phenyl group is substituted with an alkyl, aminoalkyl, hydroxyalkyl, alkoxy, hydroxyalkylamino, and a hydroxy alkoxy group, and derivatives thereof which are used as disease modifying anti-rheumatic agents and as immunosuppressants.Type: GrantFiled: July 31, 1987Date of Patent: November 28, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Edward R. Aig, John W. Coffey, Allen J. Lovey, Michael Rosenberger
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Patent number: 4877898Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.Type: GrantFiled: June 12, 1986Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
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Patent number: 4874781Abstract: A compound of formula II: ArCHR.sub.1 CO.sub.2 CHDR.sub.2in which formula:Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 represents the group --CH(CF.sub.3)CH.sub.3 or --C(CF.sub.3).dbd.CH.sub.2R.sub.2 represents the residue of an alcohol R.sub.2 CHDOH in which D is hydrogen or cyano and of which the [1R, cis]2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropane carboxylic ester is significantly insecticidal.Type: GrantFiled: January 11, 1988Date of Patent: October 17, 1989Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
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Patent number: 4874887Abstract: The present invention relates to a novel process for the preparation of insecticidally active esters of the general formula (I) ##STR1## wherein R.sub.1 and R.sub.2 are the same or diferent from each other and represent a hydrogen or a halogen atom; R.sub.3 represents ##STR2## (wherein R.sub.4 and R.sub.5 represent a chlorine or bromine atom or a methyl group when R.sub.4 is identical to R.sub.5, but R.sub.4 represents a chlorine or bromine atom or a methyl group and R.sub.5 represents a trifluoromethyl group when R.sub.4 is different from R.sub.5, and R.sub.6 represents a halogen atom or a difluoromethoxy group); and R.sub.8 represents a hydrogen or a cyano group.The characteristic of the present invention is a one-step procedure comprising directly condensing an organic acid, an aldehyde (and a water-soluble cyanide) in the presence of a phase transfer catalyst and a water-soluble inorganic base by the use of a sulphonyl compound as a condensing reagent.Type: GrantFiled: October 7, 1988Date of Patent: October 17, 1989Assignee: Lucky, Ltd.Inventors: Sang H. Jung, Seung K. Kim
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 4873018Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.Type: GrantFiled: October 27, 1987Date of Patent: October 10, 1989Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri -
Patent number: 4853151Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.Type: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
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Patent number: 4843169Abstract: Alpha-arylalkanoic esters are prepared by reacting a trivalent iodine compound of the formula ##STR1## wherein Ar is an aromatic hydrogen and X and Y each represent a group which can be removed as an anion, with a carbonyl compound of the formula ##STR2## where Ar.sup.1 is an aromatic hydrocarbon, R is a hydrogen atom or an alkyl group, and R.sup.1 is a hydrogen atom or an alkyl group, in the presence of an orthocarboxylic ester having the general formula ZC(OR.sup.2).sub.3, wherein R.sup.2 is an alkyl group and Z is a hydrogen atom or an alkyl group; the reaction being carried out in the presence of sulfuric acid in an amount from about 0.2 to about 0.8 mole per mole of the carbonyl compound.Type: GrantFiled: July 21, 1986Date of Patent: June 27, 1989Assignee: Mallinckrodt, Inc.Inventor: Robert C. Chapman
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Patent number: 4837357Abstract: 2,2-Disubstituted 3-chloropropionic esters I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl, aryl or C.sub.7 -C.sub.12 -aralkyl or R.sup.1 -C-R.sup.2 is 5-, 6- or 7-membered ring, R.sup.3 is C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl or C.sub.7 -C.sub.12 -aralkyl, are prepared by converting 2,2-disubstituted 3-hydroxypropanals II ##STR2## into the esterdiol III ##STR3## reacting this esterdiol III in the presence of a transesterification catalyst with an alcohol R.sup.3 OH to give the 3-hydroxyester IV ##STR4## reacting the hydroxyester IV with a stoichiometric or greater than stoichiometric amount of the thionyl chloride and thermally decomposing the product to give the chloropropionic ester I.Type: GrantFiled: October 21, 1987Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger
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Patent number: 4834905Abstract: 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 to 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: GrantFiled: October 3, 1986Date of Patent: May 30, 1989Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4826873Abstract: Compounds of the general formula ##STR1## wherein R.sub.1 represents hydrogen, an acyl group having 1 to 18 carbon atoms or both R.sub.1 together the group ##STR2## R.sub.2 represents hydrogen or a methyl group, have been isolated in small amounts from the leaves of Clausena lansium. The new compounds are to be used for the production of compositions for the use of the treatment of acute and chronical viral hepatitis, liver intoxication, hypoxia or amnesia.Type: GrantFiled: January 15, 1987Date of Patent: May 2, 1989Assignees: Chinese Academy of Medical Sciences, Bayer AktiengesellschaftInventors: Ming-he Yang, Yan-rong Chen, Geng-tao Liu, Liang Huang
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Patent number: 4826876Abstract: This invention relates to chemical compounds which have selective thyromimetic activity. A compound of this invention is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinyl-methyl]-thyronine.Type: GrantFiled: December 21, 1987Date of Patent: May 2, 1989Assignee: Smith Kline & French Laboratories LimitedInventors: David Ellis, John C. Emmett, Anthony H. Underwood, Paul D. Leeson
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Patent number: 4792556Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.Type: GrantFiled: April 28, 1986Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: D. V. K. Murthy, Michael C. Venuti, John M. Young
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Patent number: 4790963Abstract: A process for producing an ester is disclosed comprising contacting a gaseous reactant containing at least one organic hydroxy compound and a mixture of carbon monoxide and hydrogen with an ester synthesis catalyst of the formulaM.sub.a A.sub.b RuCu.sub.c N.sub.z O.sub.xwhereinM is selected from the group consisting of Ce, Cr, Fe, Mn and mixtures thereof,A is an alkali metal, alkaline earth metal or mixture thereof,a is from 0 to about 1,b is from 0.002 to about 10,c is from 0.2 to about 20,z is from 0 to about 196 by weight,x is the number of oxygens needed to fulfill the valence requirements of the other elements.The organic hydroxy compound can be provided separately or formed by contacting a mixture of carbon monoxide and hydrogen with an alcohol synthesis catalyst at an elevated temperature and pressure. The alcohol synthesis catalyst and ester synthesis catalyst can be in tandem or mixed.Type: GrantFiled: August 20, 1984Date of Patent: December 13, 1988Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
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Patent number: 4789382Abstract: Textile polyester material is dyed with disperse dyes in the presence of specific benzophenone derivatives, some of which are novel, to improve the light fastness.Type: GrantFiled: July 10, 1987Date of Patent: December 6, 1988Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Dieter Wegerle, Reinhold Krallmann
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Patent number: 4788218Abstract: Novel compounds having the general formula: ##STR1## wherein: R.sup.1 is hydrogen or an acyl substituent of the formula:--(C.dbd.O)--R.sup.2wherein:R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkylene, haloalkyl, aryl, haloaryl or arylalkylene are described. These compounds have both gonadotropic and antigonadotropic properties depending upon the dosage level, and are therefore useful in therapy in the control of male fertility in mammals, particularly in human beings. These compounds combine gonadotropic, antigonadotropic and androgenic properties in the same compound. Their use with LHRH antagonists on male fertility control is also disclosed.Type: GrantFiled: April 28, 1986Date of Patent: November 29, 1988Assignee: SRI InternationalInventors: Masato Tanabe, David F. Crowe, George Detre, Peters, Richard H., Mitchell A.g34 Avery
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Patent number: 4786744Abstract: The invention relates to a method for opening the ring of gem dicyanepoxides comprising reacting a gem dicyanepoxide with a mononucleophilic compound in the presence of a hydrohalic acid or a weakly nucleophilic acid.Type: GrantFiled: June 17, 1985Date of Patent: November 22, 1988Assignee: Centre National de la Recherche ScientifiqueInventors: Albert L. F. Robert, Jean-Luc Guinamant, Sylvie C. A. Jaguelin
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Patent number: 4786731Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.Type: GrantFiled: August 5, 1987Date of Patent: November 22, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell
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Patent number: 4780550Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R hu d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: September 17, 1987Date of Patent: October 25, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4776875Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.Type: GrantFiled: March 26, 1986Date of Patent: October 11, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
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Patent number: 4769176Abstract: Biphenyl esters of formula (I), wherein formula (II) represents formula (III) or formula (IV), R.sub.1 represents C.sub.3 -C.sub.12 alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkoxycarbonyloxy, j is 0 or 1, R.sub.2 represents C.sub.3 -C.sub.12 alkyl or alkoxy, one of Q.sub.1 or Q.sub.2 is fluorine and the other is hydrogen, provided that when j is 0 and formula (II) is formula (III) and both R.sub.1 and R.sub.2 are n-alkyl, then the total number of carbon atoms in R.sub.1 and R.sub.2 is more than 12. These compounds may be used as constituents of liquid crystal mixtures which show a room temperature ferroelectric smectic phase, and a number of such mixtures are described.Type: GrantFiled: October 30, 1986Date of Patent: September 6, 1988Assignee: The Secretary of State for Defence In Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Madeline J. Bradshaw, Edward P. Raynes, David I. Bishop, Ian C. Sage, John A. Jenner
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Patent number: 4752417Abstract: Alpha-isopropyl-p-chlorophenylacetic acid, which is an acid moiety of the pyrethroidal ester pesticides is subjected to optical resolution using optically active alpha-phenyl-beta-p-tolylethylamine or optically active alpha-phenylethylamine, as the optical resolution agent. The reaction of the acid with the amine is carried out in a hydrophobic organic solvent, such as aliphatic and aromatic hydrocarbons, in the presence of water, until the desired salt of the acid with the amine is separated therein through selective crystallization.Type: GrantFiled: June 19, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Ayumu Inoue, Takeaki Umemura
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Patent number: 4745209Abstract: Alpha-arylalkanoic esters are prepared by reacting a trivalent iodine compound represented by the general formula:Ar--I.dbd.Owherein Ar is an aromatic hydrocarbon, group, with a carbonyl compound represented by the general formula ##STR1## wherein Ar.sup.1 is an aromatic hydrocarbon, R is a hydrogen atom or an alkyl group and R.sup.1 is a hydrogen atom or an alkyl group, in the presence of an orthocarboxylic ester.Type: GrantFiled: March 13, 1986Date of Patent: May 17, 1988Assignee: Yasumitsu TamuraInventors: Yasumitsu Tamura, Junichi Haruta
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Patent number: 4744918Abstract: Liquid crystal phases containing at least one optically active compound of the formula IR.sup.1 --X.sup.1 --CHR.sup.o (CH.sub.2).sub.p X.sup.2 --R.sup.2 Iwherein X.sup.1 and X.sup.2 independently of one another are each --CO--O-- or --O--CO--, one of X.sup.1 and X.sup.2 may also be --O--, R.sup.1 and R.sup.2 independently of one another are each a group --(A.sup.1 --Z).sub.m --(A.sup.2).sub.n -Y, whereinA.sup.1 and A.sup.2 in each case independently of one another are a 1,4-phenylene, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene group, it also being possible for this to be monosubstituted or polysubstituted by F, Cl, Br, CN and/or alkyl groups with up to 12 C atoms, and it being possible for 1 or 2 non-adjacent CH.sub.2 groups in the alkyl groups to be replaced by O atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --N(O).Type: GrantFiled: July 11, 1985Date of Patent: May 17, 1988Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Gerd Heppke, Feodor Oestreicher
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Patent number: 4740331Abstract: Salts having the formula:Y--NH.sub.3.sup..sym..RCO.sub.2.sup..crclbar. 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. These salts are useful as corrosion inhibitors.Type: GrantFiled: February 7, 1986Date of Patent: April 26, 1988Assignee: Ciba-Geigy CorporationInventors: Emyr Phillips, David Wilson
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Patent number: 4733006Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) and iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the carbon monoxide deficient zones of the system of a catalyst stabilizer which is a germanium (IV) compound, an alkali metal compound, and mixtures thereof.Type: GrantFiled: August 18, 1983Date of Patent: March 22, 1988Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
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Patent number: 4729847Abstract: A novel, superior, optically active liquid crystal compound exhibiting a smectic C* phase, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein X represents --CH.sub.2 O-- or --OCH.sub.2 --; Y represents --COO-- or --OCO--; and either one of R.sup.1 or R.sup.2 represents an optically active alkyl group, alkoxy group or alkoxycarbonyl group and the other represents a non-optically-active alkyl group or alkoxy group each of 4 to 18 carbon atoms.Type: GrantFiled: July 10, 1986Date of Patent: March 8, 1988Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiromichi Inoue, Takashi Inukai, Kanetsugu Terashima
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Patent number: 4730077Abstract: Alpha-arylalkanoic esters are prepared by reacting a trivalent iodine compound of the formula ##STR1## wherein Ar is an aromatic hydrocarbon and X and Y each represents a group which can be removed as an anion, with a carbonyl compound of the formula ##STR2## where Ar.sup.1 is an aromatic hydrocarbon, R is a hydrogen atom or an alkyl group, and R.sup.1 is a hydrogen atom or an alkyl group, in the presence of an orthocarboxylic ester having the general formula ZC(OR.sup.2).sub.3, wherein R.sup.2 is an alkyl group and Z is a hydrogen atom or an alkyl group; the reaction being carried out in a substantially anhydrous reaction mixture.Type: GrantFiled: July 12, 1986Date of Patent: March 8, 1988Assignee: Mallinckrodt, Inc.Inventor: Robert C. Chapman
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4722811Abstract: An improved process for preparing glycol monoesters is provided which comprises reacting an alkylene oxide with a substantially hindered carboxylic acid in the presence of a hydroxy alkyl amine catalyst.Type: GrantFiled: July 21, 1986Date of Patent: February 2, 1988Assignee: Exxon Research & Engineering Co.Inventor: Allen D. Godwin
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Patent number: 4713484Abstract: A process for preparing carboxylic acid salts by the reaction of carbon monoxide with substituted or unsubstituted aromatic halides or an aliphatic organic halide. The process comprises the catalytic single phase carbonylation of the halide utilizing in addition to carbon monoxide, a palladium catalyst, an excess of tertiary phosphine, optionally an amine compound, with an alkali metal or alkaline earth metal base added during the reaction to form the salt.Type: GrantFiled: December 22, 1986Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Ronald A. Epstein
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Patent number: 4709082Abstract: 2-Phenylpropoionic acid ester of Formula (I): ##STR1## wherein R represents p-nitrophenyl group, .beta.-naphthyl group or 2-(.beta.-naphthyl)ethyl group.Optical resolution of the above is carried out by preferential crystallization by seeding either one of the optical isomers into a super-saturated solution of a racemic modification thereof or a mixture of the optical isomers thereof. The efficiency of the optical resolution can be increased by optional addition of a recemizing agent comprising a strongly basic amine or an alcholate.Type: GrantFiled: October 21, 1985Date of Patent: November 24, 1987Assignee: Nissan Chemical Industries, Ltd.Inventors: Yasuhiro Takahashi, Kazutaka Arai, Yoshio Ohara, Hiroo Matsumoto, Syuuzi Tsuchiya
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Patent number: 4709083Abstract: A method of synthesizing boron analogues of choline and choline related mrials is disclosed. The method comprises reacting N,N dimethylethanolamine with hydrogen chloride or an acid chloride to form an ester hydrochloride. The resulting aminoalcohol hydrochloride or ester hydrochloride is further reacted with tetraethyl NBH.sub.4.Also disclosed are pharamaceutically interesting compounds of acetylcholine.Type: GrantFiled: May 19, 1986Date of Patent: November 24, 1987Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Bernard F. Spielvogel
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Patent number: 4709081Abstract: The invention relates to a process for the preparation of compounds of formula (I) ##STR1## wherein R.sup.1 stands for hydrogen or the group COR.sup.2, whereinR.sup.2 stands for a straight or branched chained alkyl having 1 to 8 carbon atoms optionally substituted with phenyl, naphthyl, tetrahydronaphthyl or m-phenoxy-benzyl, cycloalkyl having 3 to 6 carbon atoms optionally substituted with one or more straight or branched chained alkyl or alkenyl having 1 to 6 carbon atoms, phenyl or naphthyl.The compounds of formula (I) are prepared according to the invention by(a) reacting esters of formula (II) ##STR2## wherein X stands for chlorine or bromine andR.sup.2 has the same meanings as defined above with a phenol alkali metal salt and(b) if desired converting the diphenyl ethers so obtained to a specific compound of formula (I), m-phenoxybenzyl alcohol by the hydrolysis of the ester group.Type: GrantFiled: September 26, 1985Date of Patent: November 24, 1987Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Gergely Heja, Dezso Korbonits, Endre Palosi, Pal Kiss, Csaba Gonczi, Ida Szvoboda nee Kanzel, Ede Marvanyos, Judit Kun, Maria Szomor nee Wundele, Gabor Szabo, Tamas Kallay, Laszlo Ledniczky
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Patent number: 4694100Abstract: A method for producing .alpha.-(p-isobutylphenyl)propionic acid or its alkyl esters which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the steps of (I): catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce isobutylbenzene and p-isobutylstyrene; and (II): reacting said p-isobutylstyrene with carbon monoxide and water or alcohol at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.-(p-isobutylphenyl)propionic acid or its alkyl ester; or (III): reacting said p-isobutylstyrene with carbon monoxide and hydrogen at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.Type: GrantFiled: July 10, 1985Date of Patent: September 15, 1987Assignee: Nippon Petrochemicals Company, Ltd.Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
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Patent number: 4686289Abstract: 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: GrantFiled: February 25, 1986Date of Patent: August 11, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4683078Abstract: A novel liquid crystal compound suitable to use as a component of liquid crystal dielectrics and a liquid crystal composition containing the same are provided, which compound is a dihalogeno-aromatic compound expressed by the formula ##STR1## wherein R represents an alkyl group or an alkoxy group, each of 1 to 12 carbon atoms, or an alkoxymethyl group of 2 to 12 carbon atoms.Type: GrantFiled: March 4, 1986Date of Patent: July 28, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto, Tetsuya Ogawa
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Patent number: 4683341Abstract: The optical resolution of an enantiomer mixture of oxycyclopentenone or a derivative thereof is conducted with a polysaccharide derivative.Type: GrantFiled: December 12, 1985Date of Patent: July 28, 1987Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Ishii, Tohru Shibata
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Patent number: 4681707Abstract: Carboxylic acid esters are produced by reacting an unsaturated hydrocarbon, for example an olefin or an alkyne, with carbon monoxide and an alcohol in the presence of a protonic acid and as catalyst (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) copper. In a modification of the invention carboxylic acids are produced by omitting the alcohol reactant and replacing it with water in an amount up to 8 mole equivalents based on the unsaturated hydrocarbon and a solvent other than an alochol, for example tetrahydrofuran.Type: GrantFiled: April 23, 1984Date of Patent: July 21, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, Bertrand Despeyroux, David J. H. Smith, James B. Woell
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Patent number: 4670582Abstract: Process for the preparation of carboxylate esters of alpha-ethylenically unsaturated alcohols by reacting an ethylenically unsaturated compound with carbon monoxide and an enolizable ketone in the presence of a catalytic system formed by combining a palladium catalyst, a triarylphosphine and a protonic acid having a pK.sub.a below 1.5, except hydrohalogenic acids and carboxylic acids.Type: GrantFiled: August 15, 1986Date of Patent: June 2, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4670586Abstract: A method for the production of an .alpha.-aryl-alkanoic acid represented by the general formula II: ##STR1## wherein R.sup.3 stands for a hydrogen atom or an alkyl group and Ar for an aromatic residue, characterized by subjecting an .alpha.-haloalkyl-aryl ketal represented by the general formula I: ##STR2## wherein Ar has the same meaning as defined above, R.sup.1 and R.sup.2 independently stand for an alkyl group and embrace the case wherein they jointly form a cyclic acetal, R.sup.3 has the same meaning as defined above, and X stands for a halogen atom to a rearrangement reaction in the presence of at least one zinc compound selected from the group consisting of oxide, hydroxide, sulfide, carbonate, and basic carbonate of zinc and subsequently hydrolyzing the product of said rearrangement reaction.Type: GrantFiled: September 10, 1985Date of Patent: June 2, 1987Assignee: Nippon Chemicals Co., Ltd.Inventors: Yuta Yabe, Takamichi Watanabe, Hisayuki Suzuki
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Patent number: 4670579Abstract: An olefin, especially an activated olefin, is telomerized by reaction with an arylamine, such as an aniline, in the presence of an alkyl nitrite, a copper catalyst, and a catalytic amount of water and/or acid and in the absence of more than about 0.5 volume part of inert solvent per volume part of olefin.Type: GrantFiled: June 30, 1986Date of Patent: June 2, 1987Assignee: Ethyl CorporationInventor: Robert I. Davidson