From Alkenyl Halides Patents (Class 560/237)
  • Patent number: 8044228
    Abstract: This invention relates to liquid crystal compositions, and polymer networks and articles comprising the compositions. The compositions comprise at least one compound of the group of compounds represented by the structures of each of the following Formulas (IV), (V) and (VI), as defined herein. A process for making the composition is also provided.
    Type: Grant
    Filed: June 8, 2009
    Date of Patent: October 25, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Marc B. Goldfinger
  • Patent number: 7473797
    Abstract: A copper(I) bi-dentate ligand complex-catalyzed procedure for synthesis of 1,3-enynes. The methods and/or systems of this invention afford a variety of enynes, tolerate a variety of sensitive functional groups, and can be employed without resort to expensive palladium reagents.
    Type: Grant
    Filed: April 27, 2005
    Date of Patent: January 6, 2009
    Assignee: University of Massachusetts
    Inventors: Dhandapani Venkataraman, Craig G. Bates, Pranorm Saejueng
  • Patent number: 6034268
    Abstract: Compounds of the formula ##STR1## in which one of the radicals R.sup.1 and R.sup.2 is methyl and the other is vinyl and one of the radicals R.sup.3 and R.sup.4 is methyl and the other is ##STR2## in which R.sup.5 is hydrogen, alkyl or alkenyl, in particular C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl, are particularly suitable as fragrances and flavors.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: March 7, 2000
    Assignee: Haarmann & Reimer GmbH
    Inventors: Horst Surburg, Horst Sommer, Stefan Lambrecht, Peter Worner, Matthias Guntert, Gunter Kindel, Volkmar Koppe
  • Patent number: 6018075
    Abstract: A process for the manufacture of a .gamma.-acetoxy-tiglic aldehyde by reacting a .gamma.-bromotiglic aldehyde or a .gamma.-chlorotiglic aldehyde with sodium acetate or potassium acetate in an organic solvent in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: January 25, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
  • Patent number: 5175346
    Abstract: Optionally halogenated tertiary allyl esters are prepared by reaction of an alkali metal salt of a carboxylic acid with an optionally halogenated primary and/or tertiary allyl halide or mixture thereof in the presence of as catalyst a cuprous salt together with a quaternary ammonium salt or a phosphonium salt.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: December 29, 1992
    Assignee: Rhone-Poulenc Sante
    Inventor: Michel Mulhauser
  • Patent number: 4933488
    Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen; and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: June 12, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4924026
    Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen, and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: May 8, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4891436
    Abstract: A process for the manufacture of bis-methylene spiro-orthocarbonate (BMSOC) wherein methyallyl chloride is subjected to the action of chlorine gas to form a mixture of 1,1-dichloromethyl ethylene and other chlorinated hydrocarbons which need not be and are not separated. The mixture is merely treated wich an alkali metal acetate such as sodium acetate to yield an easily separable second mixture by fractional distillation. The desired 1,1-diacetoxymethyl ethylene is thus recovered in high yield. It is then converted by transesterification in over 90% yield to the bismethylene spiroorthocarbonate (BMSOC). BMSOC is useful as a component for coatings composites, adhesive formulations and the like, which have the unique ability to (a) cure by free radical initiation and (b) expand during cure. BMSOC may be used as a component for dental composites, i.e. filling materials, because it reduces the possibility of leakage at the margin, i.e. at the composite-enamel interface and as a component in bone cements.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: January 2, 1990
    Assignee: Epolin, Inc.
    Inventors: Murray S. Cohen, Morris Dunkel
  • Patent number: 4791222
    Abstract: Described is a novel process for preparing dihydromyrcenol defined according to the structure: ##STR1## or the acetate thereof comprising the steps of: (i) hydrogenating .alpha.-pinene to form .alpha.-pinane;(ii) pyrolizing the resulting .alpha.-pinane to form a mixture of hydrocarbons including dihydromyrcene (or, in the alternative, forming substantially the same mixture of hydrocarbons by other well known means);(iii) reacting the resulting pinane pyrolyzate or like mixture with hydrogen chloride gas in the presence of an acid catalyst, e.g., Lewis acid or protonic acid, to form a mixture of tertiary chlorides; then(iv) reacting the mixture of tertiary chlorides with water or acetic acid int he presence of a hydroxylation catalyst defined according to the formula:M.sub.P X.sub.Qwherein M represents an element selected from the group consisting of Zn, Ca, Mg, Mn and Co; wherein X represents O or an anion, e.g.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: December 13, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Stephen R. Wilson, Leonard Steinbach, Thomas O'Rourke
  • Patent number: 4665221
    Abstract: An improved process for the preparation of primary terpenoid alcohols, e.g. 6,7-dihydrogeraniol and phytol, and of their esters with formic acid. The terpenoid formates are obtained very advantageously by reacting the corresponding tert.-vinylcarbinols with more than 2 moles, per mole of vinylcarbinol, of aqueous formic acid of more than 70 percent strength by weight, or with anhydrous formic acid, at from 5.degree. to 100.degree. C. The primary terpenoid alcohols themselves are obtained from their formates by trans-esterification with a low-boiling alcohol in the presence of a catalytic amount of a strong base. The products are valuable compounds. For example, 6,7-dihydrogeraniol is used as a scent and phytol is used as a perfume fixative and as a starting material for the synthesis of naturally occurring materials.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: May 12, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Thoemel, Werner Hoffmann
  • Patent number: 4391984
    Abstract: The invention provides a novel method for the synthetic preparation of an .omega.-haloalkyne compound of the general formula R--C.tbd.C--CH.sub.2).sub.n X, in which X is a halogen atom, R is a monovalent hydrocarbon group and n is 4, 5 or 6, by the coupling reaction of a Grignard reagent RMgX' and an .omega.-halo-1-bromoalkyne compound of the formula X--CH.sub.2).sub.n C.tbd.C-Br. The .omega.-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R--CH.dbd.CH--CH.sub.2).sub.n OCOCH.sub.3 by first acetylating and then partially hydrogenating in the presence of a Lindlar catalyst. In particular, 7, 11-hexadecadienyl acetate, which is a sexual pheromone compound of a noxious insect, is obtained in the same route of synthesis starting with the Grignard reagent of a 1-halo-3-octene and 1, 8-dibromo-1-octyne.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: July 5, 1983
    Assignee: Schin-Etsu Chemical Co., Ltd.
    Inventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4267360
    Abstract: Derivatives of hexafluoropropene dimer expressed by the following general formula ##STR1## in which R.sub.f represents (CF.sub.3).sub.2 C.dbd.C(CF.sub.2 CF.sub.3) or (CF.sub.3).sub.2 CH--CF(CF.sub.2 CF.sub.3) and R represents a hydrocarbon residue of a carboxylic acid having one free site capable of reacting with the dimer. A process for preparing the derivatives is also disclosed in which the dimer is contacted with the carboxylic acid in an inert solvent in the presence of a catalyst. Metal, amine or ammonium salts of the acid may be also used for the reaction, in which case the reaction is feasible in the absence of a catalyst.
    Type: Grant
    Filed: October 15, 1979
    Date of Patent: May 12, 1981
    Assignee: Central Glass Company, Limited
    Inventors: Masahiro Ozawa, Tadaaki Komatsu, Kimiaki Matsuoka
  • Patent number: 4164616
    Abstract: Halogen, e.g., bromine, and a conjugated diene, e.g., butadiene, are reacted in vapor phase, the reacted mass condensed and contacted with alkali metal acetate dissolved or dispersed in an acid, e.g., potassium acetate in glacial acetic acid, thus causing a reaction of formed dibromobutene-2 with the acetate to form diacetoxy-2-butene. The latter is hydrogenated to the corresponding diacetoxylated alkane. The diacetoxy alkane is hydrolyzed to the dihydroxy alkane, e.g., 1,4-butanediol. Alternately, the diacetoxy alkene can be hydrolyzed and the hydrogenation then conducted.
    Type: Grant
    Filed: January 17, 1978
    Date of Patent: August 14, 1979
    Assignee: Phillips Petroleum Company
    Inventor: William V. Childs
  • Patent number: 4069385
    Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.
    Type: Grant
    Filed: June 3, 1976
    Date of Patent: January 17, 1978
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Araki, Tsuneyuki Nagase
  • Patent number: 4048220
    Abstract: A process for the synthesis of 1,4-haloallylic esters from conjugated dienes which comprises preparing a reaction mixture of the conjugated diene, a halogenating agent, and a carboxylic acid and then adding to said reaction mixture a catalytic amount of a strong acid having a high dissociation constant. The invention is particularly described with reference to the synthesis of isoprene-1,4-chloroacetate(1-chloro-4-acetoxy-2-methyl-2-butene) from isoprene wherein a reaction mixture is prepared of isoprene with t-butyl hypochlorite in excess glacial acetic acid, to which is added H.sub.2 SO.sub.4 followed by stirring at 50.degree. C.
    Type: Grant
    Filed: May 30, 1975
    Date of Patent: September 13, 1977
    Assignee: SCM Corporation
    Inventor: Carlos G. Cardenas