Abstract: The invention relates to a process for the preparation of known .beta.-halogeno-tert.-alkyl isocyanates of the formula ##STR1## in which X represents chlorine,Y represents hydrogen or chlorine,R.sub.1 represents in each case straight-chain or branched alkyl or halogenoalkyl andR.sub.2 represents in each case straight-chain or branched alkyl, halogenoalkyl or optionally halogen- and/or trifluoromethyl-substituted phenyl,where tert.-alkyl isocyanates of the formula (II) ##STR2## in which R.sub.1 and R.sub.2 have the meaning given above,are converted to the corresponding tert.-alkylcarbamoyl chlorides by means of hydrogen chloride gas, these are reacted with elemental chlorine under irradiation or in the presence of catalysts, and finally the .beta.-halogeno-tert.-alkyl isocyanates are liberated by dehydrohalogenation at elevated temperature.
Abstract: A 3,4,3',4'-substituted biphenyl compound represented by the general formula (II): ##STR1## wherein, one of R.sup.1 and R.sup.2 is a -CH.sub.3 group and the one other is a --COOR.sup.5 group, --COOH group, or --COCl group, and one of R.sup.3 and R.sup.4 is a -CH.sub.3 group and the other one is a --COOR.sup.5 group, --COOH group, or --COCl group, is produced by the steps of oxidatively coupling an o-toluic acid alkyl ester in the presence of a catalyst containing a mixture of palladium salts with 1,10-phenanthroline or .alpha.,.alpha.'-bipyridine, a chelating product of a palladium salt with 1,10-phenanthroline, or a chelating products of a palladium salt with .alpha.,.alpha.
Abstract: The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by esterification with the hydroxy group of optically active mandelic acid methyl ester, crystallization of the diastereomeric esters and subsequent hydrolysis of the diastereomeric esters.
Abstract: In one embodiment this invention provides smoking compositions which contain a novel oxalate ester flavorantrelease additive.Under cigarette smoking conditions, a combustible filler additive such as methyl 4-oxo-.beta.-ionyl oxalate pyrolyzes and releases megastigma-5,7,9-trien-4-one as a natural flavorant component of the cigarette smoke.
Type:
Grant
Filed:
September 10, 1992
Date of Patent:
August 31, 1993
Assignees:
Philip Morris Incorporated, Philip Morris Products Inc.
Abstract: Novel aryl aliphatic acids or derivatives thereof of the general formulaR--(C.sub.x --C.sub.y)--(C.sub.m H.sub.2m)--G--C(R.sup.1).sub.2 --Ar--(C.sub.n H.sub.2n)--COOR.sup.2are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.
Type:
Grant
Filed:
June 8, 1992
Date of Patent:
August 24, 1993
Assignees:
Board of Governors of Wayne State University, Vanderbilt University
Inventors:
Carl R. Johnson, Gilles Gorins, Kenneth V. Honn, Lawrence J. Marnett
Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.
Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.
Type:
Grant
Filed:
January 24, 1992
Date of Patent:
August 10, 1993
Assignee:
Ethyl Corporation
Inventors:
Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.
Type:
Grant
Filed:
January 24, 1992
Date of Patent:
August 10, 1993
Assignee:
Ethyl Corporation
Inventors:
Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.
Type:
Grant
Filed:
January 24, 1992
Date of Patent:
August 10, 1993
Assignee:
Ethyl Corporation
Inventors:
Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.
Abstract: Novel N-(mercaptoalkyl)amides of the formula ##STR1## wherein R.sub.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sub.2 is (COR.sub.3)-aryl, heteroaryl, substituted (COR.sub.3)-aryl or substituted heteroaryl, wherein the substituents are 1-3 substituents selected from the group consisting of carboxy, alkoxycarbonyl, lower alkyl, hydroxy, halo, lower alkoxy, cyclolower alkyl, cyano, trifluoromethyl, phenyl, phenoxy and phenylthio;R.sub.3 is --OR.sub.4 or --NR.sub.4 R.sub.5 ;R.sub.4 and R.sub.5 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring;Q is hydrogen or R.sub.6 CO--;R.sub.
Abstract: A process comprising preparing an aromatic carboxylic ester and an alkyl iodide by carboxylating an aromatic iodide in the presence of an alkylating agent and a catalytic amount of a transition metal under aromatic carboxylic ester and alkyl iodide forming conditions of temperature, pressure and ultrasound.
Abstract: Disclosed herein is a free-flowing solid of 4,4'-diisocyanato dicyclohexylmethane consisting essentially of at least 90 percent of the trans,trans isomer.
Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
Type:
Grant
Filed:
June 4, 1992
Date of Patent:
July 27, 1993
Assignee:
Allergan, Inc.
Inventors:
Roshantha A. S. Chandraratna, Robert J. Weinkam
Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.
Type:
Grant
Filed:
January 24, 1992
Date of Patent:
June 22, 1993
Assignee:
Ethyl Corporation
Inventors:
Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.
Type:
Grant
Filed:
January 24, 1992
Date of Patent:
June 15, 1993
Assignee:
Ethyl Corporation
Inventors:
Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
Abstract: A process for preparing nitrogen-containing compounds which comprises contacting a carboxylated N-monosubstituted nitrogen-containing compound or a carboxylated N,N-disubstituted nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the nitrogen-containing compound.
Type:
Grant
Filed:
September 20, 1990
Date of Patent:
June 15, 1993
Assignee:
Union Carbide Chemicals & Plastics Technology Corporation
Abstract: A malonic monoester is prepared in a good yield by a single step reaction by reacting malonic acid with an alcohol in the presence of a base and an activator of malonic acid selected from the group consisting of an acyl halide or halocarbonate and an acid anhydride or dicarbonate.
Type:
Grant
Filed:
August 30, 1991
Date of Patent:
May 25, 1993
Assignee:
Kanegafuchi Chemical Industries Co., Ltd.
Abstract: There is provided a method of manufacture of dialkyl monohalomaleate and dialkyl monohalofumarate and mixtures thereof via a dehydrohalogenation of the appropriate dialkyl dihalosuccinate precursor in the presence of an aqueous base and a phase transfer catalyst.
Abstract: Diacetoxyatene compounds are obtained by reacting a perborate such as sodium perborate monohydrate or tetrahydrate and acetic acid with an iodoarene compound under mild conditions, such as 40 to 50.degree. C. The iodoarene can be further substituted by a wide range of substituents, such as halo, nitro, alkyl, alkoxy or carbosylic acid, in any position around the nucleus, except that electron withdrawing substituents occupy meta positions only. The invention process thus enables a wide range of substituted diacetoxyarene compounds to be produced using widely available and easily handled materials under mild operating conditions.