Hydrogen Halide Or Elemental Halogen Reactant Patents (Class 568/466)
  • Patent number: 10683252
    Abstract: 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: Grant
    Filed: December 15, 2017
    Date of Patent: June 16, 2020
    Assignee: Central Glass Company, Limited
    Inventors: Kenji Hosoi, Mineo Watanabe, Hideaki Imura, Kensuke Hirotaki, Naoya Ueshima
  • Patent number: 5872263
    Abstract: 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: Grant
    Filed: April 28, 1995
    Date of Patent: February 16, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Hoffmockel, Karl-Friedrich Muck, Gunter Sextro
  • Patent number: 5471005
    Abstract: 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: Grant
    Filed: November 18, 1994
    Date of Patent: November 28, 1995
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5430062
    Abstract: 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: Grant
    Filed: June 23, 1993
    Date of Patent: July 4, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Mark S. Cushman, Ernest Hamel
  • Patent number: 5414139
    Abstract: 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: Grant
    Filed: March 15, 1994
    Date of Patent: May 9, 1995
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
  • Patent number: 5008462
    Abstract: 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: Grant
    Filed: November 8, 1989
    Date of Patent: April 16, 1991
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Makoto Ishizuka, Takashi Wakasugi
  • Patent number: 4885400
    Abstract: 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: Grant
    Filed: December 1, 1987
    Date of Patent: December 5, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hiroshi Ono, Takaharu Kasuga
  • Patent number: 4825003
    Abstract: 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: Grant
    Filed: September 11, 1987
    Date of Patent: April 25, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hiroshi Ono, Takaharu Kasuga, Shinji Kiyono, Yoshihiro Fujita
  • Patent number: 4760195
    Abstract: 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: Grant
    Filed: July 28, 1987
    Date of Patent: July 26, 1988
    Assignee: Kawaken Fine Chemicals Co., Ltd.
    Inventors: Masaaki Kubo, Kazuhiro Okura
  • Patent number: 4705650
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4638091
    Abstract: 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: Grant
    Filed: February 11, 1985
    Date of Patent: January 20, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Roy D. Bowden
  • Patent number: 4579976
    Abstract: 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: Grant
    Filed: December 7, 1984
    Date of Patent: April 1, 1986
    Assignee: Atochem
    Inventors: Bernard Cheminal, Henri Mathais
  • Patent number: 4571438
    Abstract: 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: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4486608
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: December 4, 1984
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews