Unsubstituted Acids Of The Acetic Series Patents (Class 560/231)
  • Patent number: 4722939
    Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.
    Type: Grant
    Filed: December 4, 1984
    Date of Patent: February 2, 1988
    Assignee: USV Pharmaceutical Corporation
    Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
  • Patent number: 4714777
    Abstract: The subject invention relates to novel cyclopropanone hydrate derivatives of the structural formula ##STR1## whereinR.sub.1 and R.sub.2 are selected from the group consisting of --H, --(CH.sub.2).sub.n -- where n is an integer between 1 and 20, preferably 2 and 10, --COCH.sub.2 NH.sub.2, and ##STR2## and R.sub.3 and R.sub.4 selected from the group consisting of --H, --OH, 13 NH.sub.2, --CN, --COOR.sub.5, --COOH, --SH, --(CH.sub.2).sub.n OH, --(CH.sub.2).sub.n NH.sub.2, --(CH.sub.2).sub.n COOH, --(CH.sub.2).sub.n COOR.sub.5, --CCH.sub.3 OH (CH.sub.2).sub.n COOH, halogen and C.sub.7 -C.sub.10 arakyls, where n is an integer between 1 and 20, preferably 1 and 10, and R.sub.5 is an alkyl radical having between 1 and 20, preferably 1 and 10, carbon atoms;and to a process for the synthesis thereof.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: December 22, 1987
    Assignee: University of Pittsburgh
    Inventors: Paul Dowd, Christopher Kaufman, Robert H. Abeles
  • Patent number: 4711895
    Abstract: A 4-hydroxy-2-cyclopentenone represented by the following formula (I) ##STR1## wherein X represents a hydrogen or halogen atom, A represents a hydrogen atom and B represents a hydroxyl group, or A and B are bonded to each other to represent a bond, R.sup.1 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a protective group for a hydroxyl group, provided that R.sup.2 is not a 2-octenyl, 8-acetoxy-2-octenyl or 2,5-octadienyl group. The compounds of formula (I) in which A is hydrogen and B is hydroxyl group are prepared by subjecting a 5-unsubstituted cyclopentenone and an aldehyde to aldol condensation reaction. The compounds of formula (I) in which A and B form a bond is prepared by subjecting the compounds of the formula (I) in which A is hydrogen and B is hydroxyl group to dehydration.
    Type: Grant
    Filed: October 22, 1985
    Date of Patent: December 8, 1987
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori
  • Patent number: 4699989
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 13, 1987
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4689426
    Abstract: Novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenone and process for production thereof. The novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenones are represented by the following formula (I): ##STR1## wherein R.sub.a represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a substituted or unsubstituted phenyl group, R.sub.b represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms, and X represents a halogen atom. The novel cyclopentenones possess excellent pharmaceutical activities including anti-tumor activity, antiviral activity and antimicrobial activity.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: August 25, 1987
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Toshio Tanaka, Seizi Kurozumi
  • Patent number: 4668432
    Abstract: Described are alkyl-substituted-oxo-spirodecenene derivatives defined according to the structure: ##STR1## wherein X represents carbinol, carbinol C.sub.1 -C.sub.3 alkanoate or ketone; one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represents methyl and the other of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represents hydrogen; and R.sub.3 is n-butyl or isopropyl and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alkyl-substituted-oxo-spirodecenene derivatives.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: May 26, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Marie R. Hanna
  • Patent number: 4663073
    Abstract: Liquid-crystalline tercyclohexyls of the formula ##STR1## in which R is an alkyl group with 1-12 C atoms, in which one or two non-adjacent CH.sub.2 groups can be replaced by 0,X is --CN, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1 or R.sup.1, andR.sup.1 is an alkyl group having 1-12 C atoms, with the proviso that in the case where X=R.sup.1 at least one CH.sub.2 group in the alkyl group R is replaced by 0, and useful in liquid-crystalline dielectrics.
    Type: Grant
    Filed: July 12, 1985
    Date of Patent: May 5, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4658044
    Abstract: Compounds of formula (C) ##STR1## where either R.sup.D represents a hydroxymethyl group and R.sup.E represents a hydroxyl group or R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.E represents a hydroxyl group and R.sup.D represents an ethenyl group and R.sup.F represents a hydroxyl or protected hydroxyl group or a leaving group with the proviso that either R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.F represents a protected hydroxyl group, which compounds are of use as intermediates in the preparation of compounds having antiviral activity.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 14, 1987
    Assignee: Glaxo Group Limited
    Inventor: Paul Ravenscroft
  • Patent number: 4658055
    Abstract: A method for the manufacture of a heptanoic acid derivative represented by the formula ##STR1## wherein R.sup.3 stands for an acyloxy group, a halogen atom, or a hydrogen atom, which comprises reacting a cyclooctene derivative represented by the formula ##STR2## wherein Y stands for --R.sup.1, --COR.sup.1 or --SiR.sup.2.sub.3, wherein R.sup.1 is an alkyl group, an aryl group, or an aralkyl group and R.sup.2 is an alkyl group of 1 to 5 carbon atoms, with a compound represented by the formula ##STR3## wherein R.sup.3 has the same meaning as indicated above and X.sup.1 and X.sup.2 each is a halogen atom, is described along with uses for such compounds.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: April 14, 1987
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takashi Onuki, Hirokazu Naora, Asao Nakamura
  • Patent number: 4654167
    Abstract: p-Alkoxycyclohexylalkanols and their esters of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.7 -alkyl, in particular tert.-butyl, or is cyclohexyl, R.sup.2 is C.sub.1 -C.sub.3 -alkyl, in particular methyl or ethyl, and R.sup.3 is hydrogen, acetyl, propionyl or butyryl, and scent compositions containing these compounds I and processes for their preparation. The novel compounds have fine woody or sandalwood notes and can be used as scents and as components of scent compositions.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: March 31, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Degner, Walter Gramlich, Werner Hoffmann, Ludwig Schuster
  • Patent number: 4650896
    Abstract: 2-Alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process in which a 2-alkyl-1,4-diacyloxy-1,3-butadiene of the formula ##STR2## is reacted with oxygen or an oxygen donor in the presence of an acidic ion exchanger.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: March 17, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Joachim Paust
  • Patent number: 4617145
    Abstract: Described are the 1-methyl-2(2-methylbutyl) cyclohexanol derivatives defined according to the generic structure: ##STR1## wherein R represents hydrogen, MgCl, MgBr, lithium or acetyl; and uses of such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives where R is hydrogen or acetyl for their organoleptic properties in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles. Also described is the process for preparing such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives including the reactions: ##STR2## wherein the latter reaction takes place using a methane sulfonic acid catalyst.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: October 14, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, Anubhav P. S. Narula, Marie R. Hanna
  • Patent number: 4617281
    Abstract: A catalyst suitable for use in reactions catalyzed by strong base is provided. The catalyst comprises an organic compound containing a Group VA element for example an amine or phosphine supported on a solid which is insoluble in the reaction mixture. The catalyst may be activated by treatment with an epoxide. Catalysts in which the amine is an amidine or a guanidine are particularly effective.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: October 14, 1986
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4615836
    Abstract: A process for preparing an alkylmercapto ester by reacting an alkyl mercaptoalkanol with an organic carboxylic acid or an organic anhydride in the presence of a titanium-containing catalyst.
    Type: Grant
    Filed: May 18, 1984
    Date of Patent: October 7, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Rex L. Bobsein
  • Patent number: 4613457
    Abstract: Methyl pentanoic acid esters corresponding to the formula ##STR1## wherein R is an olefinically unsaturated, straight-chain or branched-chain or carbocyclic hydrocarbon group, a phenyl or alkyl substituted phenyl group, a phenyl substituted alkyl group, or a phenyl substituted alkenyl group, wherein R contains from 3 to 9 carbon atoms, are valuable perfumes having strong, generally vegetably odor notes and outstanding persistence. They are produced by esterifying 2-methyl pentanoic acid with an unsaturated or carbocyclic alcohol or phenol containing radicals R corresponding to the general formula.The compounds can be effectively combined with other perfumes and standard perfume ingredients to form new compositions. The methyl pentanoic acid ester content thereof generally amounts to between about 1 and about 50% by weight.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: September 23, 1986
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Siegfried Blosl, Klaus Bruns, Ulf-Armin Schaper
  • Patent number: 4578496
    Abstract: Polymeric complex compounds of molybdenum, tungsten, manganese, rhenium and of the metals of the sub-groups VIII and I of the Periodic Table of Elements, which complex compounds have a silica-type structure are disclosed. At least one amine ##STR1## is bonded coordinately to the central metal atom. The atomic ratio of metal to nitrogen is from 1:1 to 1:10.sup.6. The required charge compensation is effected by means of an anion. In (1), R.sup.1 and R.sup.2 represent a group ##STR2## and R.sup.4 is an alkylene grouping. The oxygen atoms are saturated by silicon atoms of further groups (2), if appropriate with incorporation of crosslinking agents. R.sup.3 may have the meaning of R.sup.1 and R.sup.2, or represents hydrogen, an alkyl group, a cycloalkyl group or the benzyl group. The polymers can contain several metals. The invention also relates to processes for their preparation, and uses in catalysis.
    Type: Grant
    Filed: October 20, 1983
    Date of Patent: March 25, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Panster, Peter Kleinschmit
  • Patent number: 4571436
    Abstract: Optically active cyclopentenolones, which are useful as an intermediate of pyrethroid insecticides, are produced from racemic cyclopentenolones according to the following procedures; (1) asymmetric hydrolysis of racemic carboxylate esters of the cyclopentenolones, (2) nitrate- or sulfonate-esterification of the asymmetrical hydrolysis products, and (3) hydrolysis of the esterification products.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: February 18, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takeaki Umemura, Ayumu Inoue, Satoshi Mitsuda
  • Patent number: 4568694
    Abstract: Cystamine derivatives of the formula: ##STR1## [wherein n represents 2 or 3, R.sup.1 and R.sup.2 each represents a hydrogen atom, or an alkyl group optionally substituted by a hydroxy, amino, alkylamino or dialkylamino group, or represents a cycloalkyl or aryl group, and X.sup.1 represents a group selected from the formulae .dbd.N--CN, .dbd.N--NO.sub.2, .dbd.N--COR.sup.3, .dbd.N--COOR.sup.3, .dbd.N--NH--CONH.sub.2, .dbd.N--SO.sub.2 R.sup.3, .dbd.CH--NO.sub.2, .dbd.CH--SO.sub.2 R.sup.3, .dbd.C(CN).sub.2, .dbd.C(CN)COOR.sup.3 and .dbd.C(CN)CONH.sub.2 (wherein R.sup.3 represents an alkyl or aryl group), or R.sup.1 represents a hydrogen atom, R.sup.2 represents an alkyl group optionally substituted by a hydroxy, amino, alkylamino or dialkylamino group, or represents a cycloalkyl or aryl group and X.sup.1 represents an oxygen or sulphur atom] have been found to be useful in the promotion of the growth of non-human animals including birds.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: February 4, 1986
    Assignee: May & Baker Limited
    Inventors: Richard M. Griffin, Malcolm N. Palfreyman
  • Patent number: 4565859
    Abstract: A polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## wherein R.sub.1 represents a residue of an organic compound having l active hydrogen atoms, n.sub.1 through n.sub.l each represents 0 or an integer of from 1 to 100, the sum of the integers represented by n.sub.1 through n.sub.l is from 1 to 100, andl represents an integer of from 1 to 100, and A represents ##STR2## and a process for production thereof; an epoxy resin represented by formula (II) ##STR3## wherein R.sub.1 and n.sub.1 through n.sub.l are defined above, and B is an oxycyclohexane unit having a substituent and is represented by formula (III) ##STR4## wherein X represents a ##STR5## --CH.dbd.CH.sub.2, or ##STR6## groups, wherein R.sub.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: January 21, 1986
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Shoji Watanabe, Kimio Inoue, Toyokazu Yagii
  • Patent number: 4560811
    Abstract: Novel methods for making chlorohydrins are provided using a Lewis acid catalyst with an olefin and peroxy compound or where an enantiomer is desired, a Lewis acid catalyst in combination with a chiral alcohol, particularly glycol, and a combination of a peroxy compound and alkenol. In certain situations, an epoxide may be employed.
    Type: Grant
    Filed: January 18, 1984
    Date of Patent: December 24, 1985
    Assignee: Massachusetts Institute of Technology
    Inventors: Karl B. Sharpless, Roy A. Johnson
  • Patent number: 4554095
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives defined according to the structure: ##STR1## wherein Z represents hydrogen, acyl having the structure: ##STR2## and substituted oxyacyl having the structure: ##STR3## and cyclic condensation products thereof having the structure: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 represent C.sub.1 -C.sub.10 alkyl; wherein R.sub.1 ' represents C.sub.1 -C.sub.10 alkylidene and wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or C.sub.1 -C.sub.3 lower alkyl; processes for preparing same by means of a reaction of a halomethyloxirane or substituted halomethyloxirane with a substituted 1,3-propanedione derivative; and organoleptic uses of such 1-hydroxymethyl-2-acyl cyclopropane derivatives in augmenting or enhancing the aroma or taste of perfume compositions, perfumed articles (e.g.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: November 19, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • 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: 4543421
    Abstract: An improved method for the preparation of prostaglandin analogs which comprises preparation of two equivalents of an alkyl or alkenyl lithium reagent in an aprotic solvent mixture such as pentane or hexane and tetrahydrofuran, conversion of said reagent by addition of 1 equivalent of copper (I) cyanide to a copper reagent, conversion of said copper reagent to the blocked prostaglandin analog by the addition of a 2-alkylcyclopent-2-en-1-one reagent and quenching of the resultant reaction mixture with aprotic media or an active acylating agent and finally optionally deblocking the resultant product is disclosed. This method is an improvement over previous methods in that more modest temperatures and less hazardous and/or less complex reagents are used and in that for some analogs the method is shorter than previous methods.
    Type: Grant
    Filed: May 11, 1983
    Date of Patent: September 24, 1985
    Assignee: Miles Laboratories, Inc.
    Inventors: Paul F. Corey, Harold C. Kluender
  • Patent number: 4535182
    Abstract: 2-Cyclopentenone esters of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is lower alkyl, lower alkenyl, lower alkynyl, or cycloalkyl, cycloalkenyl or substituted or unsubstituted aryl and R.sup.3 is hydrogen or lower alkyl are prepared in high yields by reacting the corresponding racemic or optically active 4-cyclopentenone of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and R.sup.3 is hydrogen or acyl with at least one lower aliphatic carboxylic acid and/or metal or amine salts thereof.
    Type: Grant
    Filed: August 16, 1983
    Date of Patent: August 13, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4529813
    Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: July 16, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • Patent number: 4529810
    Abstract: Optically-active alpha-substituted carboxylic esters are prepared by treating a non-symmetrical ketene with an alcohol in the presence of an optically-active amine catalyst. Hydrolysis of the resulting esters, yields the optically-active acid corresponding to the non-symmetrical ketene.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: July 16, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4528142
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives having one of the structures: ##STR1## and utilities thereof for their organoleptic properties.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: July 9, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4528396
    Abstract: Novel cyclic di- and tetraester compounds made from the reaction of various unsaturated cyclic compounds with carboxylic acid anhydrides in the presence of oxygen are described. The process to make these novel ester compounds is preferably conducted at a temperature in the range from about 50.degree. to 150.degree. C. and in the presence of a catalyst. A transition metal borate catalyst is preferred. Such ester compounds are potentially useful plasticizers, lubricants, solvents and fuel additives.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: July 9, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr.
  • Patent number: 4521342
    Abstract: 2-alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 and R.sup.3 are each hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process wherein a 2-alkyl-2,4-diacyloxybut-3-enal of the formula ##STR2## is treated with an aliphatic carboxylic acid.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: June 4, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Hans-Martin Weitz, Joachim Paust
  • Patent number: 4518790
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16- substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion, and particularly, alkyl esters, such as the methyl ester, of such acids.
    Type: Grant
    Filed: July 18, 1980
    Date of Patent: May 21, 1985
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • 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: 4513146
    Abstract: Ester is produced by reacting highly hindered carboxylic acid or salt thereof represented by the formula ##STR1## wherein a. R.sub.3, R.sub.4, and R.sub.5 are each independently a monovalent organo group, andb. M is hydrogen, monovalent metal, or the monovalent fractional part of a polyvalent metal,with organic carbonate represented by the formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently monovalent organic groups which may be the same or different, and wherein the alpha carbon of at least one of R.sub.1 and R.sub.2 is substantially sterically unhindered.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: April 23, 1985
    Assignee: PPG Industries, Inc.
    Inventor: Ralph B. Thompson
  • Patent number: 4510319
    Abstract: The invention relates to a process for preparing compounds having the general structure: ##STR1## wherein R is hydrogen or an acyclic or alicyclic fragment containing between one and about ten carbon atoms, and R.sub.1 is hydrogen or an alkyl containing between one and about four carbon atoms or an aryl group.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: April 9, 1985
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman, Philip A. Christenson, John M. Yurecko, Jr.
  • Patent number: 4506105
    Abstract: A process for preparing cyclooctene-4-ol-1 with a content in excess of 70% by reacting cyclooctadiene-1,5 with formic acid and then saponifying or transesterifying the cyclooctenyl formate with an alcohol of low boiling point.In the absence of a catalyst, formic acid is reacted with cyclooctadiene-1,5 at 50.degree. to 200.degree. C., preferably 95.degree. to 105.degree. C. The reaction product without further processing is directly distilled, and the formic acid ester so obtained is transesterified with an alcohol of low boiling point into the formate of that alcohol and into cyclooctene-4-ol-1.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: March 19, 1985
    Assignee: Chemische Werke Huls AG
    Inventor: Manfred Kaufhold
  • Patent number: 4504412
    Abstract: Fragrance compounds having the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl and R.sup.2 is hydrogen or lower alkyl.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: March 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventor: Eugene G. Harris
  • Patent number: 4504672
    Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.
    Type: Grant
    Filed: November 5, 1980
    Date of Patent: March 12, 1985
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4499297
    Abstract: Cyclopentenones of formula ##STR1## wherein each of symbols R.sup.1 and R.sup.2, when taken separately, represents an alkyl radical of C.sub.1 to C.sub.6, or a hydrogen atom, or, when taken together, they represent a polymethylene, or one of them designates a hydrogen atom and the other an alkyl radical of C.sub.1 to C.sub.6, are prepared starting from compounds having formula ##STR2## wherein R stands for a C.sub.1 to C.sub.6 alkyl radical or a phenyl group, via a catalytic reaction promoted by a metallo-organic compound of formulaMeX.sub.2 (R.sup.3 CN).sub.2 (III)wherein Me represents palladium or platinum, R.sup.3 represents a C.sub.1 to C.sub.3 alkyl radical or a phenyl group and X defines a halogen atom.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: February 12, 1985
    Assignee: Firmenich, SA
    Inventor: Valentin Rautenstrauch
  • Patent number: 4496767
    Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.
    Type: Grant
    Filed: October 18, 1983
    Date of Patent: January 29, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4489092
    Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C-- or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CH or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
    Type: Grant
    Filed: September 1, 1982
    Date of Patent: December 18, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4481148
    Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: November 6, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4451403
    Abstract: Described is the genus of compounds defined according to the structure: ##STR1## wherein at least one of the lines:[++++]represents a carbon-carbon single bond and the other of the lines:[++++]represents a carbon-carbon double bond or a carbon-carbon single bond; wherein the moiety X represents one of the moieties: ##STR2## wherein when the moiety X has the structure: ##STR3## then one of the lines:[++++]is a carbon-carbon double bond and the other of the lines:[++++]is a carbon-carbon single bond and when the moiety X has the structure: ##STR4## then both of the lines:[++++]represent carbon-carbon single bonds; wherein, one of R.sub.1, R.sub.2 and R.sub.3 represent 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:(i) when the line:[++++]at the 3-4 position is a double bond, then R.sub.3 is hydrogen or 2-methyl-1-propenyl; and(ii) when the line:[++++]at the 2-3 position is a double bond, then R.sub.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: May 29, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Philip T. Klemarczyk
  • Patent number: 4413118
    Abstract: Organic sulfur compounds containing a carbon-sulfur double bond are used to remove homogeneous catalyst group VIII metals from chemical process streams.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: November 1, 1983
    Assignee: Merck & Co., Inc.
    Inventors: F. Edward Roberts, Victor J. Grenda
  • Patent number: 4410461
    Abstract: A catalytic homogeneous liquid phase process for effecting the acyloxylation of toluene to produce the corresponding benzylic ester. The catalyst system comprises Pd(II) and Pb(II) values wherein the palladous element component is associated with a catalytic amount of a tertiary phosphine as a complexed ligand. The indicated catalyst system uniquely facilitates the advantageous use of normally immiscible carboxylic acid reactants for carrying out the underlying benzylic oxidation reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: October 18, 1983
    Assignee: Ashland Oil, Inc.
    Inventor: Peter E. Throckmorton
  • Patent number: 4410720
    Abstract: 11-Unsubstituted 16-fluoro-prostaglandin E.sub.2 useful as blood pressure lowering agents.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: October 18, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4410719
    Abstract: 2-Alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 and R.sup.3 are each hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process in which a 2-alkyl-1,4-diacyloxybuta-1,3-diene of the formula ##STR2## is reacted with oxygen or an oxygen donor, in the presence of a carboxylic acid of the formulaR.sup.3 -COOH III.
    Type: Grant
    Filed: June 29, 1982
    Date of Patent: October 18, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Hans-Martin Weitz, Joachim Paust
  • Patent number: 4403100
    Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: September 6, 1983
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4397789
    Abstract: Described are the 4-cyclooctenyl lower alkyl carbonates reaction products including a major proportion of said 4-cyclooctenyl alkyl carbonates and a minor proportion of bicyclooctanyl carbonates having the structure: ##STR1## wherein R.sub.5 is methyl or ethyl, said mixture being produced by: first reacting 1,5-cyclooctadiene with formic acid to form a mixture of 4-cyclooctenyl formate in a major proportion and bicyclooctanyl formate in a minor proportion and then reacting the resulting mixture with an alkyl carbonate in the presence of an alkali metal alkoxide to form a mixture of compounds defined above and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, hair sprays, shampoos, bath oils and perfumed polymers.
    Type: Grant
    Filed: August 19, 1982
    Date of Patent: August 9, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Michael Licciardello
  • Patent number: 4393245
    Abstract: New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: July 12, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hoffman, Karl von Fraunberg, Manfred Baumann
  • Patent number: T103403
    Abstract: This disclosure describes esters having prostaglandin-like activity of 15-deoxy-16-hydroxy-16-substituted-prostanoic acids formed by replacing the hydroxy group of the C.sub.1 -carboxylic acid substituent with para-acetamidophenoxy, methylsulfonylamido, para-acetylphenoxy, para-phenylphenoxy, C.sub.3 -C.sub.10 cycloalkoxy, arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms, phenoxy or phenoxy substituted with 1-3 chlorine atoms or C.sub.1 -C.sub.3 alkyl, phenacyloxy or phenacyloxy ring-substituted with from 1-3 bromine atoms, a nitro moiety, C.sub.1-C.sub.8 arylalkyl, or arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms; substituted arylamino (C.sub.1 -C.sub.12), substituted-naphthoxy, fluorenoxy, carboxyalkoxy (C.sub.5 -C.sub.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: September 6, 1983
    Inventors: Martin J. Weiss, Charles V. Grudzinskas, Middleton B. Floyd, Jr., Sow-Mei L. Chen