By Dehydrohalogenation Of A Halohydrin Or By Reacting A Hypohalite Or Hypohalous Acid With An Ethylenically Unsaturated Compound At The Site Of Unsaturation Patents (Class 549/520)
  • Patent number: 5055601
    Abstract: A process for epoxidation of a fluoro-olefin is disclosed. The process comprises epoxidizing a fluoro-olefin represented by the general formula (I): ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 each represents a substituent selected from (a)--F, (b) a perfluoroalkyl group having 2 to 20 carbon atoms and (c) --CF.sub.2 Y.sup.1, Y.sup.1 may be the same or different and represents a substituent selected from (d) a halogen atom selected from F, Cl, Br and I, (e) --OZ.sup.1 and (f) --Z.sup.1, wherein Z.sup.1 may be the same or different and represents a substituted or unsubstituted hydrocarbon group having not more than 20 carbon atoms, and X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 may be combined with one another to form a cyclic compound, provided that all of X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 do not represent --F; using a hypochlorite dissolved or suspended in an aqueous phase as an oxidizing agent in the presence or absence of an inorganic base.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: October 8, 1991
    Assignee: Asahi Kasei Kogyo K.K.
    Inventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
  • Patent number: 4965379
    Abstract: A process for epoxidation of a fluoro-olefin is disclosed. The process comprises epoxidizing a fluoro-olefin represented by the general formula (I): ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 each represents a substituent selected from (a) --F, (b) a perfluoroalkyl group having 2 to 20 carbon atoms and (c) --CF.sub.2 Y.sup.1, Y.sup.1 may be the same or different and represents a substituent selected from (d) a halogen atom selected from F, Cl, Br and I, (e) --OZ.sup.1 and (f) --Z.sup.1, wherein Z.sup.1 may be the same or different and represents a substituted or unsubstituted hydrocarbon group having not more than 20 carbon atoms, and X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 may be combined with one another to form a cyclic compound, provided that all of X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 do not represent --F; using a hypochlorite dissolved or suspended in an aqueous phase as an oxidizing agent in the presence or absence of an inorganic base.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: October 23, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
  • Patent number: 4933477
    Abstract: Phenyl-substituted epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl, alkenyl, phenyl, halogen, nitro, alkoxy, haloalkyl, phenoxy or phenylsulfonyl, are prepared by reducing a haloacetophenone to a halohydrin and reacting the halohydrin with an alkali metal hydroxide by a process in which the reduction with the alkali metal borohydride and the reaction are carried out in aqueous organic solution, or the cyclization of a halohydrin with an alkali metal hydroxide is carried out in an organic liquid.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: June 12, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Hans-Gert Recker, Hubert Smuda
  • Patent number: 4925961
    Abstract: A process for producing hexafluoropropylene oxide from hexafluoropropylene is described. The process comprises epoxidizing hexafluoropropylene in a two-phase system of an aqueous phase and an organic phase by the use of a hypochlorite as an oxidizing agent, the hypochlorite being dissolved or dispersed in the aqueous phase, in the presence of at least one catalyst selected from the group consisting of (a) quaternary ammonium salts, (b) quaternary phosphonium salts, (c) quaternary arsonium salts, and (d) lipophilic complexing agents for cations contained in the hypochlorite, and also, in the presence or absence of an inorganic base.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: May 15, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
  • Patent number: 4902810
    Abstract: A process for producing hexafluoropropylene oxide from hexafluoropropylene is described. The process comprises epoxidizing hexafluoropropylene in a two-phase system of an aqueous phase and an organic phase by the use of a hypochlorite as an oxidizing agent, the hypochlorite being dissolved or dispersed in the aqueous phase, in the presence of at least one catalyst selected from the group consisting of (a) quaternary ammonium salts, (b) quaternary phosphonium salts, (c) quaternary arsonium salts, and (d) lipophilic complexing agents for cations contained in the hypochlorite, and also, in the presence or absence of an inorganic base.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: February 20, 1990
    Assignee: Asahi Kogaku Kogyo Kabushiki Kaisha
    Inventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
  • Patent number: 4849531
    Abstract: A process for the preparation of a 2,3-epoxyamide of the formula ##STR1## in which R.sup.1 represents hydrogen or straight-chain or branched C.sub.1 -C.sub.8 -alkyl, which may be substituted by phenyl or halogen, or represents C.sub.3 -C.sub.7 -cycloalkyl, phenyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, or a group of the formula ##STR2## in which R.sup.4 and R.sup.5 are identical or different and denote hydrogen, phenyl, benzyl, acetyl or C.sub.1 -C.sub.8 -alkyl which is optionally substituted by phenyl or halogen,R.sup.2 represents hydrogen or an amino protecting group andR.sup.3 represents a radical which activates the methylene group,comprising reacting a 2-halogeno-3-hydroxyamide of the formula ##STR3## in which X represents fluorine, chlorine, bromine or iodine,with an alkali metal hydroxide in an inert solvent.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: July 18, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Wolfgang Hartwig
  • Patent number: 4496752
    Abstract: Chlorine and tertiary alkanol dissolved in an inert organic solvent are reacted with aqueous alkali to produce tertiary alkyl hypochlorite which is recovered in the organic solvent and reacted with water and olefinically unsaturated compound to produce chlorohydrin and tertiary alkanol. Chlorohydrin and tertiary alkanol recovered in the organic solvent are contacted with aqueous alkali to produce the epoxy compound, and tertiary alkanol recovered in the organic solvent is recycled to hypochlorite production. The process may be integrated with the electrolytic production of chlorine, with an appropriate treatment of the recycle aqueous stream when required.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: January 29, 1985
    Assignee: The Lummus Company
    Inventors: Abraham P. Gelbein, Joon T. Kwon
  • Patent number: 4496753
    Abstract: A chlorohydrin, such as glycerol dichlorohydrin is saponified in two stages, with the first stage being carried out in a high back-mix saponification reactor, and the second stage being carried out in a plug-flow saponification reactor. The use of two different stages improves both selectivity and yield.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: January 29, 1985
    Assignee: Lummus Crest, Inc.
    Inventors: Joon T. Kwon, George D. Suciu
  • Patent number: 4443620
    Abstract: Chlorine and tertiary alkanol dissolved in an inert organic solvent are reacted with calcium oxide in aqueous calcium chloride to produce tertiary alkyl hypochlorite which is recovered in the organic solvent and reacted with water and olefinically unsaturated compound to produce chlorohydrin and tertiary alkanol. Chlorohydrin and tertiary alkanol recovered in the organic solvent are contacted with calcium oxide in aqueous calcium chloride to produce the epoxy compound, and tertiary alkanol recovered in the organic solvent is recycled to hypochlorite production. Calcium chloride produced as by-product in the hypochlorite production and saponification is recovered as an aqueous solution having a calcium chloride concentration of at least 25 wt. % to provide calcium chloride in a usable form.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: April 17, 1984
    Assignee: The Lummus Company
    Inventors: Abraham P. Gelbein, Arthur S. Nislick
  • Patent number: 4410714
    Abstract: A process for producing an epoxy compound by chlorinating a tertiary alkanol to the corresponding hypochlorite, followed by reaction of the hypochlorite with water and an olefinically unsaturated compound to produce the corresponding chlorohydrin and saponification of the chlorohydrin to the corresponding epoxy compound. The hypochlorite production and the saponification are effected with calcium oxide in an aqueous solution of calcium chloride, with calcium chloride being produced as by-product in an aqueous solution having a calcium chloride concentration of at least 25 wt. %. In this manner, calcium chloride by-product is recovered in a more usable form thereby eliminating the problems associated with recovery of calcium chloride by-product.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: October 18, 1983
    Assignee: The Lummus Company
    Inventor: George J. Apanel
  • Patent number: 4376865
    Abstract: Olefin is reacted with alkyl hypochlorite and water to produce an effluent containing the chlorohydrin and alkanol. An organic solvent is employed to extract the alkanol and chlorohydrin from the aqueous effluent, followed by saponification with base to produce olefin oxide. Olefin oxide is separated from the saponification effluent, followed by separation of an organic phase of the organic solvent, and an aqueous phase, which contains the alkanol. The aqueous phase containing alkanol, is chlorinated to produce the alkyl hypochlorite, with the organic phase being recycled to the extraction. The process is preferably integrated with the electrolytic production of chlorine.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: March 15, 1983
    Assignee: The Lummus Company
    Inventor: George J. Apanel
  • Patent number: 4348535
    Abstract: There are disclosed substituted lactones of the formula ##STR1## wherein A stands for --CH--CH.sub.2 X (X being Cl, Br or OH), --CHY--CHY-- (Y being Cl or Br), or ##STR2## and R.sup.1, R.sup.2 and R.sup.3 are the same or different radicals from the group of hydrogen and C.sub.1 to C.sub.10 alkyls, at least one of the radicals R.sup.1, R.sup.2 and R.sup.3 being such an alkyl radical, and process for making the same.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: September 7, 1982
    Assignee: Dynamit Nobel AG
    Inventor: Hans-Georg Schmidt