Ethylenically Unsaturated Patents (Class 568/857)
-
Patent number: 4390738Abstract: Olefine oxides or derivatives thereof such as glycols are produced by reacting an olefinic compound e.g. ethylene, propylene or butadiene with oxygen in the presence of a catalyst containing copper bonded to a peroxo group.Type: GrantFiled: June 18, 1981Date of Patent: June 28, 1983Assignee: Imperial Chemical Industries PLCInventors: Dhafir Y. Waddan, Derek Williams
-
Patent number: 4388479Abstract: The process for producing C.sub.4 -C.sub.10 ethylene alcohols of the formula: ##STR1## wherein (a) R.sub.1 is --CH.sub.2 OH, R.sub.2 =R.sub.3 =--H;(b) R.sub.1 is --H, R.sub.2 =--CH.sub.3, R.sub.3 =--CH.sub.3 or --C.sub.6 H.sub.11comprises hydrogenation of acetylene alcohols of the formula: ##STR2## wherein (a) R.sub.1 is CH.sub.2 OH, R.sub.2 =R.sub.3 =--H;(b) R.sub.1 is --H, R.sub.2 is --CH.sub.3, R.sub.3 is --CH.sub.3 or --C.sub.6 H.sub.11,in the form of technical products in the liquid phase on a membrane catalyst made of an alloy consisting of palladium and ruthenium at a mass ratio therebetween of 90-94:10-6 respectively. Hydrogenation of said alcohols is effected by means of hydrogen diffusing through a membrane catalyst at a temperature of from 60.degree. to 180.degree. C. under atmospheric pressure of hydrogen. The process is simple in its scheme and the equipment employed. It avoids losses of noble metals of the catalyst and makes it possible to obtain the desired products in a yield of up to 99.Type: GrantFiled: April 9, 1981Date of Patent: June 14, 1983Inventors: Vladimir M. Gryaznov, Andrei N. Karavanov, Tamara M. Belosljudova, Anatoly V. Ermolaev, Anatoly P. Maganjuk, Irina K. Sarycheva
-
Patent number: 4386227Abstract: A process for the preparation of a two-functional-group-containing terpen having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl, or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.Type: GrantFiled: March 22, 1982Date of Patent: May 31, 1983Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
-
Patent number: 4382151Abstract: 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraene-2-ols of the general formula: ##STR1##Type: GrantFiled: August 27, 1981Date of Patent: May 3, 1983Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Takeshi Suzuki, Toshiharu Ohgoh, Manabu Murakami, Kiyoshi Oketani, Hideaki Fujisaki
-
Patent number: 4338251Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.Type: GrantFiled: December 29, 1980Date of Patent: July 6, 1982Assignees: Eisai Co., Ltd., Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
-
Patent number: 4328378Abstract: A method for producing optically active or racemic 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane characterized by reducing optically active or racemic 2-hydroxy-2,6-dimethyl-6-heptenal and oxidizing the resuling optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol, and optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol.Type: GrantFiled: February 9, 1981Date of Patent: May 4, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito
-
Patent number: 4317905Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.Type: GrantFiled: May 21, 1979Date of Patent: March 2, 1982Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
-
Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
-
Patent number: 4306100Abstract: Alkenediols are produced by hydrolysis of a dibromoalkenes in the presence of alkali metal formate. In a preferred embodiment, alkenediols, and particularly 2-butene-1,4-diol, are produced in a series of steps comprising bromination of conjugated diene with cupric bromide, hydrolysis of the resulting dibromobutenes to alkenediols in the presence of alkali metal formate, and regeneration of cupric bromide and alkali metal formate such that only conjugated diene, oxygen and water are consumed.Type: GrantFiled: June 16, 1980Date of Patent: December 15, 1981Assignee: Standard Oil Company (Indiana)Inventor: George R. Wood
-
Patent number: 4283579Abstract: A process for producing a diol by reacting an acetic ester of butanediol or butenediol with methanol, which comprises (a) continuously feeding to a first reaction-distilling column from its upper part a liquid acetic ester of butanediol or butenediol, while continuously feeding methanol to said column from its lower part, to bring both feeds into counter current gas-liquid contact in the presence of an acidic or a basic catalyst, to allow both feeds to react, and withdrawing from the bottom a bottom stream comprising a diol as major constituent, (b) continuously feeding to a hydrolyzer the distillate obtained from said first reaction-distilling column containing methyl acetate as major constituent, thus bringing said distillate into contact with water or steam in the presence of an acidic catalyst to hydrolyze the methyl acetate, (c) then continuously feeding the hydrolysis product thus obtained from the hydrolyzer to a second distilling column, withdrawing a methyl acetate-containing methanol stream from theType: GrantFiled: September 6, 1979Date of Patent: August 11, 1981Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Hiroshi Oka
-
Patent number: 4283580Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene carbonate to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.Type: GrantFiled: September 19, 1979Date of Patent: August 11, 1981Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Hiroshi Odanaka, Minoru Saotome, Toshihiko Kumazawa
-
Patent number: 4277632Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene oxide to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.Type: GrantFiled: September 19, 1979Date of Patent: July 7, 1981Assignee: Nippon Shokubai Kaguku Kogyo Co., Ltd.Inventors: Toshihiko Kumazawa, Takeshi Yamamoto, Hiroshi Odanaka
-
Patent number: 4276217Abstract: A method for producing optically active or racemic 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane characterized by reducing optically active or racemic 2-hydroxy-2,6-dimethyl-6-heptenal and oxidizing the resulting optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol, and optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol.Type: GrantFiled: July 21, 1980Date of Patent: June 30, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito
-
Patent number: 4273944Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.Type: GrantFiled: October 30, 1979Date of Patent: June 16, 1981Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
-
Patent number: 4255338Abstract: A process for the hydrogenation of butadienepolyperoxide in a suitable solvent, e.g., tetrahydrofuran, at temperatures of 75.degree.-110.degree. C. and pressure above 2000 psia by contacting the butadienepolyperoxide and hydrogen in the presence of metallic silver. The process produces 1-butene-3,4-diol and 2-butene-1,4-diol.Type: GrantFiled: October 12, 1979Date of Patent: March 10, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: William W. Prichard
-
Patent number: 4254289Abstract: In the reaction of 3-methyl-3-buten-1-ol with aqueous formaldehyde forming isomeric alkene-1,5-diols, particularly 3-methylene-1,5-pentanediol and 3-methyl-2-pentene-1,5-diol, it has been found that yields of the diols surprisingly are substantially increased if the reaction is effected in the presence of added isobutene and the mol ratio of 3-methyl-3-buten-1-ol to formaldehyde is at least 1:1.Type: GrantFiled: January 12, 1977Date of Patent: March 3, 1981Assignee: Chevron Research CompanyInventors: Robert G. Wall, Shigeto Suzuki, John B. Wilkes
-
Patent number: 4251673Abstract: An organic ester e.g. 1,4-diacetoxybutane is hydrolyzed with an alkali metal or an alkaline earth metal hydroxide to a corresponding alcohol, the reaction being rapidly effected by having present a hydroxyl-containing compound. In a preferred embodiment, the hydroxyl-containing compound to be present is the very compound to be produced e.g. 1,4-butanediol is to be produced from 1,4-diacetoxybutane and there is present during the reaction of hydrolysis an earlier produced 1,4-butanediol.Type: GrantFiled: July 3, 1979Date of Patent: February 17, 1981Assignee: Phillips Petroleum CompanyInventors: Harold W. Mark, William V. Childs
-
Patent number: 4234747Abstract: Butenediol is obtained by reacting butadiene with water and oxygen in the presence of an iron catalyst and preferably in the presence of carbon dioxide or sulphur dioxide.Type: GrantFiled: July 20, 1979Date of Patent: November 18, 1980Assignee: Imperial Chemical Industries LimitedInventor: Christopher J. McIndoe
-
Patent number: 4233230Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.Type: GrantFiled: May 4, 1978Date of Patent: November 11, 1980Assignee: Rhone-Poulenc IndustriesInventor: Jean Otton
-
Patent number: 4209651Abstract: A process for the hydrogenation of butadienepolyperoxide in a suitable solvent, e.g., tetrahydrofuran, at temperatures of 75.degree.-110.degree. C. and pressure above 2000 psia by contacting the butadienepolyperoxide and hydrogen in the presence of metallic silver. The process produces 1-butene-3,4-diol and 2-butene-1,4-diol.Type: GrantFiled: February 21, 1979Date of Patent: June 24, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: William W. Prichard
-
Patent number: 4179579Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.Type: GrantFiled: July 25, 1977Date of Patent: December 18, 1979Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
-
Patent number: 4169961Abstract: An alkenediol is produced from an alkenol by contacting the alkenol with formaldehyde at a pH maintained between about 4 and 7. Preferably this pH range is maintained by adding a buffering agent composed of a weak acid and the salt of a weak acid. Particularly advantageous buffering agents are the lower organic polycarboxylic acids with disodium or dipotassium hydrogen phosphate and sodium or potassium dihydrogen phosphate with disodium or dipotassium hydrogen phosphate.Type: GrantFiled: July 11, 1977Date of Patent: October 2, 1979Assignee: Chevron Research CompanyInventors: Robert G. Wall, John B. Wilkes, Shigeto Suzuki
-
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
-
Patent number: 4160115Abstract: Butenediol is obtained by reacting butadiene with water and oxygen in the presence of a copper, nickel, cobalt, chromium, manganese or molybdenum catalyst and preferably in the presence of carbon dioxide.Type: GrantFiled: September 5, 1978Date of Patent: July 3, 1979Assignee: Imperial Chemical Industries LimitedInventors: Charles H. Vasey, Dhafir Y. Waddan
-
Patent number: 4158096Abstract: Synthesis and intermediates for making insect pheromone useful in the control of red scale, Aonidiella aurantii.Type: GrantFiled: March 13, 1978Date of Patent: June 12, 1979Assignee: Zoecon CorporationInventor: Richard J. Anderson
-
Patent number: 4122291Abstract: Production of an alken-2-ol-1, or of an alken-2-ol-1 and an alkanol-1 from the corresponding alken-3-ol-1 is described. The above compound or compounds can be produced with good selectivity by converting an alken-3-ol-1 to the boric acid ester, and, then, contacting the ester with a palladium catalyst in the presence of hydrogen or, alternatively, by carrying out the latter-mentioned step under conditions favorable to the formation of said boric acid ester and, thereafter, subjecting the reaction product to solvolysis.Type: GrantFiled: June 6, 1977Date of Patent: October 24, 1978Assignee: Kuraray Co., Ltd.Inventors: Sunao Kyo, Tsumoru Renge, Hidetsugu Tanaka
-
Patent number: 4118406Abstract: A process for preparing cis-olefins of the formula ##STR1## where R ia alkyl or alkenyl and R.sup.1 is alkyl and alkenyl, both optionally substituted by hydroxy, carbalkoxy or acyloxy, which comprises an ylide solution of the compound R--CH.sub.2 --P.sup..sym. (C.sub.6 H.sub.5).sub.3 Br.sup..crclbar. in hexaalkyl phosphoric acid traimide and adding an aldehyde of the formula R.sup.1 --CHO.Type: GrantFiled: August 8, 1977Date of Patent: October 3, 1978Assignee: Hoechst AktiengesellschaftInventors: Hans Jurgen Bestmann, Werner Theo Stransky, Otto Vostrowsky
-
Patent number: 4117249Abstract: The invention relates to acetylenic glycols having the formula : ##STR1## wherein R is hydrogen or an alkenyl group, and to their derivatives obtained through hydrogenation or ethoxylation reactions, these compounds showing outstanding surface active properties. The invention relates also to the process for the preparation of the subject compounds starting from 6-methyl-5-hepten-2-one.Type: GrantFiled: June 23, 1976Date of Patent: September 26, 1978Assignee: Anic, S.p.A.Inventors: Renato De Simone, Edoardo Platone, Morello Morelli
-
Patent number: 4100208Abstract: Process for production of ethylenic compounds by hydrogenating the corresponding alkynol with isopropyl alcohol in the presence of a metal complex such as IrH.sub.3 CO(P.phi..sub.3).sub.2 and IrH.sub.3 (P.phi..sub.3).sub.2.Type: GrantFiled: April 11, 1974Date of Patent: July 11, 1978Assignee: Snam Progetti S.p.A.Inventors: Federico Maspero, Emilio Perrotti