Hydrogen Halide Or Elemental Halogen Reactant Patents (Class 568/466)
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Patent number: 10683252Abstract: Fluoral is obtained by gas-phase fluorination of chloral in the presence of a catalyst and then reacted with trimethyl orthoformate, thereby readily forming 1,2,2,2-tetrafluoroethyl methyl ether as an intermediate for production of desflurane. 1,2,2,2-Tetrafluoroethyl difluoromethyl ether (desflurane) is produced with high yield from the thus-formed 1,2,2,2-tetrafluoroethyl methyl ether by chlorination and fluorination. This method enables efficient industrial-scale production of desflurane useful as an inhalation anesthetic.Type: GrantFiled: December 15, 2017Date of Patent: June 16, 2020Assignee: Central Glass Company, LimitedInventors: Kenji Hosoi, Mineo Watanabe, Hideaki Imura, Kensuke Hirotaki, Naoya Ueshima
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Patent number: 5872263Abstract: A process for separating a gaseous reaction mixture in the preparation of trioxane is described, in which a) the gaseous mixture leaving the reactor is scrubbed in countercurrent with an organic solvent whose boiling point is above 135.degree. C. in which the trioxane predominantly dissolves and which leaves the formaldehyde predominantly in the gas phase which is returned to the reactor, b) the trioxane together with residual formaldehyde is stripped from the solvent by distillation via a column, the overhead product being partially condensed in the temperature range from 62.degree. to 100.degree. C. c) some of the resulting condensate is applied to the column as reflux and some is taken off as product and d) the non-condensed portion is returned to the scrubbing step a).Type: GrantFiled: April 28, 1995Date of Patent: February 16, 1999Assignee: Hoechst AktiengesellschaftInventors: Michael Hoffmockel, Karl-Friedrich Muck, Gunter Sextro
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Patent number: 5471005Abstract: A procedure for forming methylmalonaldehyde from propionaldehyde, an alkyl formate and a sodium alkoxide, utilizing a crossed-Claisen condensation is disclosed. The procedure avoids the formation of aldol condensation products. Also disclosed are processes for preparing 3-alkoxy-2-methylpropenals such as 2-methyl-3-(2-methyl-2-propenoxy)propenal from methylmalonaldehyde. The latter products are useful in the synthesis of carotenoids.Type: GrantFiled: November 18, 1994Date of Patent: November 28, 1995Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 5430062Abstract: The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.Type: GrantFiled: June 23, 1993Date of Patent: July 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Mark S. Cushman, Ernest Hamel
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Patent number: 5414139Abstract: A process for manufacturing monochloroacetaldehyde trimer and chloral together by effectively utilizing a raw material acetaldehyde or para-aldehyde. The process comprises a step of chlorinating acetaldehyde or para-aldehyde to produce a chlorinated liquid of which the major component is monochloroacetaldehyde, a step comprising adding chloral to said chlorinated liquid and distilling the mixture to obtain a fraction of which the major components are monochloroacetaldehyde and chloral, a step of trimerizing monochloroacetaldehyde by reacting said fraction in the presence of a trimerization catalyst and separating the MCA trimer by filtration, and a step of chlorinating other fractions from said distillation step and the filtrate from said trimerization step to produce chloral. According to this process all raw material aldehydes and components derived from aldehydes which have not been consumed for the production of MCA trimer can be easily converted into chloral which is useful as an industrial chemical.Type: GrantFiled: March 15, 1994Date of Patent: May 9, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5008462Abstract: A method for preparing a monochloroacetaldehyde trimer in a high yield is here disclosed which comprises the steps of dissolving, in an organic solvent, a solution containing monochloroacetaldehyde as the main component, and then trimerizing monochloroacetaldehyde in the presence of sulfuric acid. The thus prepared monochloroacetaldehyde trimer can be heated at 120.degree. C. under atmospheric pressure to obtain pure monochloroacetaldehyde.Type: GrantFiled: November 8, 1989Date of Patent: April 16, 1991Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Makoto Ishizuka, Takashi Wakasugi
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Patent number: 4885400Abstract: In the production of 2-chloropropionaldehyde by the hydroformylation of vinyl chloride in the presence of a rhodium catalyst in combination with a base, the activity of the catalyst can be improved significantly by maintaining the concentration of produced 2-chloropropionaldehyde in the reaction solution at not higher than 10%.Further, it is possible to continue the reaction for a long period of time while maintaining the activity of the catalyst at a high level by carrying out the reaction in a water insoluble or hardly soluble solvent simultaneously with water extraction, separating the catalyst solution and the extraction water from each other, separating 2-chloropropionaldehyde from the extraction water by distillation or similar means so as to lower its concentration to a given level or below, and using the extraction water again after subjecting it to an anion exchange treatment.Type: GrantFiled: December 1, 1987Date of Patent: December 5, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hiroshi Ono, Takaharu Kasuga
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Patent number: 4825003Abstract: A process for the production of 2-chloropropionaldehyde from vinyl chloride, carbon monoxide and hydrogen which comprises using a rhodium compound and a trivalent organic phosphorus compound or the oxide of a trivalent organic phosphorus compound as a catalyst and carrying out the reaction under the co-existence of an acid the pka of which is in the range of 0.5-5, the oxide, hydroxide or a weak acid salt of an alkali metal or alkaline earth metal, or a buffer solution.Type: GrantFiled: September 11, 1987Date of Patent: April 25, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hiroshi Ono, Takaharu Kasuga, Shinji Kiyono, Yoshihiro Fujita
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Patent number: 4760195Abstract: A 5-bromo-1-pentanal compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 respectively represent, independently from each other, a member selected from the group consisting of a hydrogen atom and alkyl radicals having 1 to 7 carbon atoms, or an acetal derivative of said 5-bromo-1-pentanal compound, is produced by subjecting a starting compound selected from the group consisting of 4-pentenal compounds of the formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and acetal derivatives of the above-mentioned compounds, to a free radical addition reaction with hydrogen bromide in a liquid medium at a temperature of 10.degree. C. to 60.degree. C.; in the presence of a free radical initiator or by irradiating ultraviolet rays to the reaction mixture, and by collecting the resultant reaction product from the reaction mixture.Type: GrantFiled: July 28, 1987Date of Patent: July 26, 1988Assignee: Kawaken Fine Chemicals Co., Ltd.Inventors: Masaaki Kubo, Kazuhiro Okura
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4638091Abstract: A method for the preparation of a fluorinated amine of the formula: ##STR1## wherein X represents hydrogen or fluorine, R represents hydrogen, lower alkyl, difluoromethyl or trifluoromethyl and each of R.sup.1 and R.sup.2, independently, represents hydrogen or lower alkyl, which comprises reacting a carbonyl compound of the formula:XCF.sub.2 CORat an elevated temperature with a nitrogenous base of the formula: ##STR2## and hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: February 11, 1985Date of Patent: January 20, 1987Assignee: Imperial Chemical Industries PLCInventor: Roy D. Bowden
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Patent number: 4579976Abstract: There is disclosed a continuous catalytic process for the preparation of trifluoroacetaldehyde through fluorination in the gaseous phase of trichloroacetaldehyde in a single reaction zone at a temperature between 230.degree. C. and 260.degree. C., on a catalyst comprising a gamma alumina impregnated by Cr.sub.2 O.sub.3 in an amount of 1.5 to 4 atoms of chromium per liter of alumina and activated at a temperature between 300.degree. C. and 400.degree. C. by a mixture of hydrofluoric acid and 1,1,2-trichloro-1,2,2-trifluoro-ethane.Type: GrantFiled: December 7, 1984Date of Patent: April 1, 1986Assignee: AtochemInventors: Bernard Cheminal, Henri Mathais
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Patent number: 4571438Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: March 21, 1985Date of Patent: February 18, 1986Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Dennis S. Banasiak
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Patent number: 4486608Abstract: A process for making mono- and dichlorinated or brominated aldehydes from aldehydes having at least 3 carbon atoms and hydrogens alpha to the carbonyl group or primary alcohols having at least 3 carbon atoms and hydrogens in the 2-position by direct bromination or chlorination by carrying out the bromination or chlorination in an inert organic solvent with bromine or chlorine and containing a catalyst complex of HX and an N,N-dialkyl or cycloalkylformamide where X is a counterion.Type: GrantFiled: April 22, 1983Date of Patent: December 4, 1984Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, Richard G. Pews