Preparing From Alkenyl Halide Patents (Class 568/847)
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Patent number: 8278361Abstract: 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: GrantFiled: January 20, 2009Date of Patent: October 2, 2012Assignee: Unimatec Co., Ltd.Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato
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Patent number: 6506947Abstract: 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: GrantFiled: December 20, 2001Date of Patent: January 14, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Marie-Jose Lina, Eric Lacroix, Sophie Vanpoulle, Gerard Orcel, Robert Overton
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Patent number: 6043400Abstract: 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: GrantFiled: December 30, 1996Date of Patent: March 28, 2000Assignee: The Dow Chemical CompanyInventor: Edward M. Jorge
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Patent number: 5532389Abstract: 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: GrantFiled: September 9, 1994Date of Patent: July 2, 1996Assignee: The Dow Chemical CompanyInventors: 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
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Patent number: 5523425Abstract: 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: GrantFiled: December 21, 1994Date of Patent: June 4, 1996Assignee: The Dow Chemical CompanyInventors: Gunther A. Pech, Werner J. Witzl
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Patent number: 5516929Abstract: 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: GrantFiled: February 12, 1993Date of Patent: May 14, 1996Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
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Patent number: 5486627Abstract: 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: GrantFiled: December 2, 1994Date of Patent: January 23, 1996Assignee: The Dow Chemical CompanyInventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
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Patent number: 5344945Abstract: 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: GrantFiled: March 12, 1993Date of Patent: September 6, 1994Assignee: Solvay (Societe Anonyme)Inventor: Frans Grunchard
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Patent number: 5292972Abstract: 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: GrantFiled: October 13, 1992Date of Patent: March 8, 1994Assignee: Shell Oil CompanyInventors: Christopher S. John, Wilfridus P. M. Maas
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Patent number: 5227543Abstract: 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: GrantFiled: October 10, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Wihelm K. Amberg
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Patent number: 5126494Abstract: 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: GrantFiled: April 23, 1990Date of Patent: June 30, 1992Assignee: Massachusetts Institute of TechnologyInventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
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Patent number: 4900849Abstract: 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: GrantFiled: September 9, 1988Date of Patent: February 13, 1990Assignee: Shell Oil CompanyInventor: David I. Saletan
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Patent number: 4704463Abstract: 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: GrantFiled: May 27, 1986Date of Patent: November 3, 1987Assignee: Shell Oil CompanyInventor: George C. Blytas
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Patent number: 4696726Abstract: 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: GrantFiled: July 14, 1986Date of Patent: September 29, 1987Assignee: Shell Oil CompanyInventors: George C. Blytas, F. Norman Grimsby, John F. Scamehorn
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Patent number: 4665240Abstract: 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: GrantFiled: May 27, 1986Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventors: George C. Blytas, Stephen A. Shain
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Patent number: 4562299Abstract: 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: GrantFiled: December 12, 1984Date of Patent: December 31, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Mario Gambaro
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Patent number: 4533772Abstract: 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: GrantFiled: August 29, 1983Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4533773Abstract: 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: GrantFiled: March 22, 1984Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4496778Abstract: 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: GrantFiled: October 3, 1983Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4496779Abstract: 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: GrantFiled: April 26, 1984Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4486613Abstract: 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: GrantFiled: September 20, 1982Date of Patent: December 4, 1984Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
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Patent number: 4482763Abstract: 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: GrantFiled: July 19, 1982Date of Patent: November 13, 1984Assignee: Exxon Research & Engineering Co.Inventors: Richard G. Austin, Robert C. Michaelson
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Patent number: 4413151Abstract: 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: GrantFiled: July 14, 1982Date of Patent: November 1, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
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Patent number: 4390739Abstract: 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: GrantFiled: October 9, 1981Date of Patent: June 28, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4278517Abstract: 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: GrantFiled: June 26, 1980Date of Patent: July 14, 1981Assignee: Union Carbide CorporationInventor: Anthony G. Abatjoglou
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Patent number: 4115458Abstract: 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: GrantFiled: July 29, 1977Date of Patent: September 19, 1978Assignee: GAF CorporationInventor: Eugene V. Hort