From Alkenyl Halides Patents (Class 560/237)
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Patent number: 8044228Abstract: 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: GrantFiled: June 8, 2009Date of Patent: October 25, 2011Assignee: E.I. du Pont de Nemours and CompanyInventor: Marc B. Goldfinger
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Patent number: 7473797Abstract: 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: GrantFiled: April 27, 2005Date of Patent: January 6, 2009Assignee: University of MassachusettsInventors: Dhandapani Venkataraman, Craig G. Bates, Pranorm Saejueng
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Patent number: 6034268Abstract: 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: GrantFiled: November 4, 1998Date of Patent: March 7, 2000Assignee: Haarmann & Reimer GmbHInventors: Horst Surburg, Horst Sommer, Stefan Lambrecht, Peter Worner, Matthias Guntert, Gunter Kindel, Volkmar Koppe
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Patent number: 6018075Abstract: 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: GrantFiled: May 12, 1999Date of Patent: January 25, 2000Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
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Patent number: 5175346Abstract: 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: GrantFiled: April 26, 1991Date of Patent: December 29, 1992Assignee: Rhone-Poulenc SanteInventor: Michel Mulhauser
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Patent number: 4933488Abstract: 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: GrantFiled: December 26, 1989Date of Patent: June 12, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
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Patent number: 4924026Abstract: 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: GrantFiled: August 11, 1989Date of Patent: May 8, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
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Patent number: 4891436Abstract: 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: GrantFiled: November 21, 1988Date of Patent: January 2, 1990Assignee: Epolin, Inc.Inventors: Murray S. Cohen, Morris Dunkel
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Patent number: 4791222Abstract: 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: GrantFiled: July 31, 1984Date of Patent: December 13, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Stephen R. Wilson, Leonard Steinbach, Thomas O'Rourke
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Patent number: 4665221Abstract: 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: GrantFiled: July 25, 1983Date of Patent: May 12, 1987Assignee: BASF AktiengesellschaftInventors: Frank Thoemel, Werner Hoffmann
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Patent number: 4391984Abstract: 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: GrantFiled: May 22, 1981Date of Patent: July 5, 1983Assignee: Schin-Etsu Chemical Co., Ltd.Inventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
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Patent number: 4331814Abstract: 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: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4267360Abstract: 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: GrantFiled: October 15, 1979Date of Patent: May 12, 1981Assignee: Central Glass Company, LimitedInventors: Masahiro Ozawa, Tadaaki Komatsu, Kimiaki Matsuoka
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Patent number: 4164616Abstract: 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: GrantFiled: January 17, 1978Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: William V. Childs
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Patent number: 4069385Abstract: 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: GrantFiled: June 3, 1976Date of Patent: January 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Araki, Tsuneyuki Nagase
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Patent number: 4048220Abstract: 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: GrantFiled: May 30, 1975Date of Patent: September 13, 1977Assignee: SCM CorporationInventor: Carlos G. Cardenas