Preparing From Alkenyl Halide Patents (Class 568/847)
  • Patent number: 8278361
    Abstract: Disclosed is a mixture of fluoroalkyl alcohols represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)cOH [Ia] and CF3(CF2)n-1(CF?CH)aCF2(CF2CF2)b(CH2CH2)cOH [Ib], wherein n is an integer of 1 to 5, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3. This fluoroalkyl alcohol mixture is produced by the reaction of a fluoroalkyl iodide represented by the general formula: CF3(CF2)n(CH2CF2)a(CF2CF2)b(CH2CH2)cI [II], with N-methylformamide, followed by hydrolysis in the presence of a basic compound.
    Type: Grant
    Filed: January 20, 2009
    Date of Patent: October 2, 2012
    Assignee: Unimatec Co., Ltd.
    Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato
  • Patent number: 6506947
    Abstract: The subject-matter of the invention is a fluorinated diol and its process of preparation. The fluorinated diol corresponds to the formula (I): CnF2n+1—A—CH2OCH2—C(CH2OH)2—R in which n has a value from 2 to 20 and A means —CH═CH— or —CH2CH2— and R is an alkyl group comprising 1 to 4 carbon atoms.
    Type: Grant
    Filed: December 20, 2001
    Date of Patent: January 14, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Marie-Jose Lina, Eric Lacroix, Sophie Vanpoulle, Gerard Orcel, Robert Overton
  • Patent number: 6043400
    Abstract: This invention is a process for preparing chlorohydrins by reacting a chlorinating species, such as hypochlorous acid, with at least one unsaturated organic compound, such as propylene or butylene, at a pH of greater than 6.0. The chlorinating species is formed in a first step by reacting a source of chlorine, such as Cl.sub.2 gas, with an aqueous pH adjusting source, such as aqueous NaOH.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: March 28, 2000
    Assignee: The Dow Chemical Company
    Inventor: Edward M. Jorge
  • Patent number: 5532389
    Abstract: A process of preparing alkylene oxides comprises steps of: (1) optionally forming a hypochlorite solution; (2) contacting chlorine with a solution of a hypochlorite below about 60.degree. C., and a pH of less than about 5.5, with sufficient micromixing to achieve a product hypochlorous acid in a yield of at least about 80 percent; (3) separating at least a portion the hypochlorous acid from an aqueous metal chloride solution wherein the solution is sprayed as droplets; (4) distilling the remaining liquid phase; (5) absorbing the hypochlorous acid and dichlorine monoxide in low-chlorides water to produce a low-chlorides aqueous hypochlorous acid solution; (6) contacting the low-chlorides aqueous hypochlorous acid solution with an olefin in a continuous process to form a olefin chlorohydrin; (7) optionally contacting the olefin chlorohydrin with a base to form a alkylene oxide and a salt solution; and (8) optionally separating the alkylene oxide from the salt solution.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: David L. Trent, George J. Quarderer, Kim G. Bargeron, Douglas C. Greminger, David J. Koranek, Erik J. Stewart, Curtis N. Swisher, Cheryl A. Tirtowidjojo, Danil Tirtowidjojo
  • Patent number: 5523425
    Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: June 4, 1996
    Assignee: The Dow Chemical Company
    Inventors: Gunther A. Pech, Werner J. Witzl
  • Patent number: 5516929
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: May 14, 1996
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
  • Patent number: 5486627
    Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: January 23, 1996
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
  • Patent number: 5344945
    Abstract: Process for the production of epichlorohydrin in which the chloroaliphatic impurities formed at the hypochlorination of allyl chloride to dichloropropanols are removed from the crude aqueous solution of dichloropropanols before dehydrochlorination, by extraction with a recycled organic solvent which is rich in 1,2,3-trichloropropane.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: September 6, 1994
    Assignee: Solvay (Societe Anonyme)
    Inventor: Frans Grunchard
  • Patent number: 5292972
    Abstract: The invention relates to a process for the production of dichlorohydrin which comprises reacting allylchloride, water and chlorine in a reaction zone to form an aqueous solution comprising dichlorohydrin and chlorinated organic byproducts, and contacting the aqueous solution with 1,2,3-trichloropropane to obtain an aqueous layer comprising the dichlorohydrin and an organic layer comprising the trichloropropane and chlorinated organic byproducts, separating both layers and recovering the dichlorohydrin.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: March 8, 1994
    Assignee: Shell Oil Company
    Inventors: Christopher S. John, Wilfridus P. M. Maas
  • Patent number: 5227543
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Wihelm K. Amberg
  • Patent number: 5126494
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallo-chloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: June 30, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
  • Patent number: 4900849
    Abstract: A process for the continuous production of di- and/or epichlorohydrin is disclosed wherein impurities, e.g., chloroaliphatic alkanes and chloroaliphatic ethers are removed by energy efficient solvent extraction and are obtained in relatively concentrated form for further processing or disposal.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: February 13, 1990
    Assignee: Shell Oil Company
    Inventor: David I. Saletan
  • Patent number: 4704463
    Abstract: A process for the production of epichlorohydrin is disclosed which comprises reacting allyl chloride, chlorine and water to form an intermediate, then rapid conversion and separation of epichlorohydrin product; the epichlorohydrin-depleted reaction mixture is cooled and subjected to electrodialysis then reverse osmosis to concentrate and remove deleterious by-products, and at least a substantial portion of the resultant permeate is recycled to the reaction zone, thereby enabling reduced operating costs and/or improved yield.
    Type: Grant
    Filed: May 27, 1986
    Date of Patent: November 3, 1987
    Assignee: Shell Oil Company
    Inventor: George C. Blytas
  • Patent number: 4696726
    Abstract: A continuous process for the production of dichlorohydrin by the reaction of allyl chloride, water and chlorine having substantially lower energy requirements than conventional processes, wherein the reaction mixture is subjected to reverse osmosis to concentrate the dichlorohydrin and to provide a permeate stream substantially free of dichlorohydrin, which permeate stream is recycled to the reaction.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: September 29, 1987
    Assignee: Shell Oil Company
    Inventors: George C. Blytas, F. Norman Grimsby, John F. Scamehorn
  • Patent number: 4665240
    Abstract: A continuous process for the production of dichlorohydrin by the reaction of chlorine, water and allyl chloride, having reduced water consumption wherein the dichlorohydrin formed is extracted into an inert organic solvent and the remaining aqueous reaction product is subjected to reverse osmosis, and at least a portion of the resulting permeate is recycled to the reaction.
    Type: Grant
    Filed: May 27, 1986
    Date of Patent: May 12, 1987
    Assignee: Shell Oil Company
    Inventors: George C. Blytas, Stephen A. Shain
  • Patent number: 4562299
    Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: December 31, 1985
    Assignee: Montedison S.p.A.
    Inventors: Carlo Venturello, Mario Gambaro
  • Patent number: 4533772
    Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4533773
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.
    Type: Grant
    Filed: March 22, 1984
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4496779
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as 1,4-diazabicyclo [2.2.2.] octane is disclosed.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4496778
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as pyridine is disclosed.
    Type: Grant
    Filed: October 3, 1983
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4486613
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an oxidant selected from organic hydroperoxides, H.sub.2 O.sub.2, and oxygen and a catalyst composition comprising at least one osmium carbonyl catalyst, such as Os.sub.3 (CO).sub.12, and optionally at least one cocatalyst such as NaI, is disclosed.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 4, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4482763
    Abstract: A process for hydroxylating olefins with an organic hydroperoxide and water in the presence of an osmium containing catalyst (e.g. OsO.sub.4) and an organic halogenated hydrocarbon co-catalyst (e.g., n-butyl iodide) is disclosed.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: November 13, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson
  • Patent number: 4413151
    Abstract: A process for hydroxylating olefins using a supported osmium catalyst such as Os.sub.3 (CO).sub.12 adsorbed on a support, such as MgO, and optionally in conjunction with a co-catalyst such as NaI, is disclosed.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: November 1, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4390739
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins with an oxygen containing gas and water in the presence of a catalyst composition comprising (i) a catalytically active metal oxide such as OsO.sub.4, (ii) as a co-catalyst I a transition metal salt such as CuBr.sub.2, and (iii) optionally a co-catalyst II salt such as tetra ethyl ammonium bromide is disclosed.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: June 28, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4278517
    Abstract: A process for producing glycols by the catalytic oxidation of olefinic compounds which comprises contacting an olefinic compound with an organic selenoxide in an aqueous alkaline medium in the presence of a catalytic amount of octavalent osmium to form the corresponding glycol.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: July 14, 1981
    Assignee: Union Carbide Corporation
    Inventor: Anthony G. Abatjoglou
  • Patent number: 4115458
    Abstract: 2-Chloro-2,3,3-tribromo-1,4-butanediol and processes for producing same by reacting dibromobutenediol in a liquid medium with bromine and chlorine.
    Type: Grant
    Filed: July 29, 1977
    Date of Patent: September 19, 1978
    Assignee: GAF Corporation
    Inventor: Eugene V. Hort