Halogen Containing Patents (Class 568/681)
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Patent number: 8865947Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).Type: GrantFiled: December 6, 2012Date of Patent: October 21, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, Sheng Peng
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Patent number: 8283500Abstract: An azeotrope comprising desflurane (CF3CFHOCF2H) and hydrogen fluoride (HF). The azeotrope can be prepared by fractionally distilling a crude mixture of desflurane and HF. Purer desflurane can be readily and easily separated from the azeotrope. It is emphasized that this abstract is provided to comply with the rules requiring an abstract which will allow a searcher or other reader quickly to ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the appended issued claims.Type: GrantFiled: February 9, 2006Date of Patent: October 9, 2012Assignee: Halocarbon Products CorporationInventors: Paul Mazzell, Barry Jones, Neville Pavri, Joel Swinson
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Publication number: 20120238782Abstract: A method for producing allyl chloride is provided which includes: a chlorination step of reacting propylene with chlorine to obtain a reaction product containing allyl chloride, unreacted propylene and by-product hydrogen chloride; a separation step of cooling the reaction product to separate the reaction product into the allyl chloride and a mixed gas containing the unreacted propylene and the by-product hydrogen chloride; a collection step of separating the mixed gas into the unreacted propylene and the by-product hydrogen chloride to collect the unreacted propylene; and an oxidation step of oxidizing the separated by-product hydrogen chloride to obtain chlorine. At least part of the chlorine used in the chlorination step is the chlorine obtained in the oxidation step. A method for producing dichlorohydrin using the chlorine obtained in the oxidation step is also provided.Type: ApplicationFiled: October 20, 2010Publication date: September 20, 2012Inventors: Masahiro Kinoshita, Norihito Omoto
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Patent number: 8263811Abstract: Process for preparing one or more iodinated organic substances having a molecular mass of less than 2000 (substances (S)) using (A) at least one free-radical-generating substance chosen from peroxides, diazo compounds, dialkyldiphenylalkanes, substances derived from tetraphenylethane, boranes and iniferter substances comprising at least one thiuram disulphide group, (B) an ethylenically unsaturated substance capable of adding a free radical to its ethylenic double bond, (C) molecular iodine, which comprises the steps according to which at least a fraction of (A), at least a fraction of (B) and at least a fraction of (C) are introduced into a reactor, and then the contents of the reactor are caused to react, while introducing therein the possible remainder of (A), the possible remainder of (B) and the possible remainder of (C), until a moment is reached when the content of the reactor is a mixture comprising one or more substances (S).Type: GrantFiled: May 6, 2010Date of Patent: September 11, 2012Assignee: Solvay (Société Anonyme)Inventors: Patrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski
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Publication number: 20120004470Abstract: The present invention relates to a process for producing an ether compound in a simplified, efficient manner, including the step of reacting a hydroxyl group-containing compound with an epoxy compound in the presence of an oxide of a metal of Group 4 of the Periodic Table on which a sulfate ion is supported, wherein a sum of a diffraction intensity of a (111) crystal lattice plane and a diffraction intensity of a (?111) crystal lattice place of the metal oxide is 2000 cps or larger as measured by subjecting the metal oxide to powder X-ray diffraction analysis.Type: ApplicationFiled: February 18, 2010Publication date: January 5, 2012Applicant: KAO CorporationInventors: Tomotaka Matsumoto, Takafumi Nishi, Mitsuru Uno
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Patent number: 8039678Abstract: The present invention refers to a process for the preparation of chloromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether (sevochlorane), which consists of reacting hexafluoroisopropanol with: a formaldehyde equivalent selected between paraformaldehyde or 1,3,5-trioxane, a chlorinating agent selected from the group consisting of oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, sulfuryl chloride and thionyl chloride, and a strong acid selected from the group consisting of concentrated or fuming sulfuric acid. Said process provides sevochlorane in high purity and yield, which can be converted to sevoflurane by known means.Type: GrantFiled: September 29, 2006Date of Patent: October 18, 2011Assignee: Cristalia Produtos Quimicos Farmaceuticos Ltda.Inventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
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Patent number: 7988877Abstract: A method of making a fluorinated ether includes combining, in a polar aprotic solvent: a fluorinated alcohol represented by the formula X—Rf1CH2OH, and a fluorinated sulfonate ester represented by the formula Rf2CH2OS(?O)2Rf3, and base; and obtaining a fluorinated ether represented by the formula Y—Rf1CH2OCH2Rf2—Y. Rf1 is selected from perfluorinated C1-C10 alkylene groups having from 1 to 10 carbon atoms and partially fluorinated C1-C10 alkylene groups, and derivatives thereof having catenated heteroatom(s). X represents H, F, or an HOCH2— group. Rf2 is selected from perfluorinated C1-C10 alkyl groups and partially fluorinated C1-C10 alkyl groups, and derivatives thereof having catenated heteroatom(s). Rf3 is a C1-C4 alkyl group. Y represents H, F, or an Rf2CH2OCH2— group. A variant method, useful for preparing symmetric fluorinated ethers, is also disclosed. The present disclosure also provides fluorinated ethers preparable according to the methods.Type: GrantFiled: November 3, 2008Date of Patent: August 2, 2011Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
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Publication number: 20110082312Abstract: The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.Type: ApplicationFiled: May 4, 2009Publication date: April 7, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT DESCHRANKTER HAFTUNGInventors: Nikolai (Mykola) Ignatyev, Wolfgang Hierse, Martin Seidel, Andreas Bathe, Jens Schroeter, Karsten Koppe, Thorsten Meier, Peter Barthen, Walter Frank
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Patent number: 7544844Abstract: There is provided a process for producing 3,3,3-trifluoropropionaldehyde, including the step of hydrolyzing a benzyl vinyl ether of the formula [1] in the presence of a catalyst selected from the group consisting of Arrhenius acids and Lewis acids, [Chem. 17] where R represents phenyl or phenyl having a substituent R1 selected from the group consisting of alkyl groups, alkoxy groups, halogen atoms, nitro groups and amino groups.Type: GrantFiled: September 12, 2006Date of Patent: June 9, 2009Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
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Patent number: 7230147Abstract: The invention concerns a method for functionalizing a double bond and, more particularly, a double bond bearing a metalloid atom. Said functionalization is produced by the action of perhalogenated sulphonyl chloride on the carbon bearing sulphur in the presence of a free radical initiator, preferably by homolytic cleavage. The invention is useful in organic synthesis.Type: GrantFiled: June 11, 2004Date of Patent: June 12, 2007Assignee: Shasun Pharma Solutions LimitedInventor: Nicolas Roques
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Patent number: 7193119Abstract: To provide a process for producing a fluorinated alkyl ether, whereby a sufficient reaction rate can be attained even under mild reaction conditions, and a post-process such as distillation after the reaction can be efficiently carried out. A process for producing a fluorinated alkyl ether, which comprises introducing an aprotic polar solvent, a fluorinated ether, a catalyst, a fluorinated alkyl alcohol and a fluorinated olefin into a reactor, and then, reacting the fluorinated alkyl alcohol with the fluorinated olefin, characterized in that the ratio of the two components of the aprotic polar solvent and the fluorinated ether introduced into the reactor is the aprotic polar solvent/the fluorinated ether=5/95 to 80/20 by mass ratio.Type: GrantFiled: February 7, 2006Date of Patent: March 20, 2007Assignee: Asahi Glass Company, LimitedInventors: Masazumi Nagai, Hidekazu Okamoto, Kazuya Oharu
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Patent number: 7091374Abstract: Fluorinated compounds and emulsions including the compounds. The compositions are useful as oxygen carriers and surfactants. In one embodiment, the fluorinated compound is pH sensitive. In one embodiment, the fluorinated compound is a vitamin E derivative. In one embodiment, the fluorinated compound is a vitamin K derivative.Type: GrantFiled: April 23, 2004Date of Patent: August 15, 2006Assignee: Sonus Pharmaceuticals, Inc.Inventors: Yuehua Zhang, Manjari Lal, Andrew Leo, Nagesh Palepu
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Patent number: 6849194Abstract: Highly fluorinated, saturated, and unsaturated fluoroethers are efficient, economical, non-ozone-depleting fire extinguishing agents used alone or in blends with other fire extinguishing agents in total flooding and portable systems. Methods for producing ethers, halogenated ether intermediates, and fluoroethers are disclosed. Novel fluoroether compositions are disclosed. Fluoroether extinguishing mixtures, methods, and systems are disclosed.Type: GrantFiled: May 12, 2003Date of Patent: February 1, 2005Assignee: PCBU Services, Inc.Inventors: Mark Robin, Thomas F. Rowland, John Chien, Janet Boggs, Mitchel Cohn, Vicki Hedrick, Stephan Brandstadter
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Patent number: 6770776Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.Type: GrantFiled: September 25, 2001Date of Patent: August 3, 2004Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Publication number: 20030187291Abstract: Iodohydroxylated olefins can be prepared by treating an olefin with an aqueous solution of an iodine monohalide selected from iodine monochloride and iodine monobromide.Type: ApplicationFiled: January 31, 2003Publication date: October 2, 2003Inventors: Yongkui Sun, Thorsten Rosner
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Patent number: 6566559Abstract: Process for the production of unsaturated ethers, in particular isopropenyl methyl ether (IPM), by pyrolysis of a ketal-containing or acetal-containing mixture, in particular dimethoxypropane (DMP), in the liquid phase in the presence of an organic carboxylic acid, according to the following reaction scheme: wherein R1=H or alkyl with 1-8 C atoms; R2=H, CH3—, C2H5—, or Cl—; R3=alkyl with 1-8 C atoms; R4=H, CH3—, C2H5—, or C3H7—, and R1 and R4 may be joined to form a 5-, 6-, or 7-membered ring. DMP is produced by the process from acetone and methanol by reaction in an acidic heterogeneous ion exchanger, the product being isolated by extraction with aqueous alkaline solution. In particular the process involves combining the IPM reaction product with the DMP reaction product, which permits the execution of a stable recycling process in which the methanol-containing streams of the IPM and DMP stages can be simultaneously extracted.Type: GrantFiled: June 1, 2001Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Steffen Krill, Stephan Kretz, Volker Häfner, Georg Markowz
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Patent number: 6406680Abstract: This invention describes a new type of X-ray contrast agents. It has been found that iodinated alkenes containing one or several C═C double bonds substituted with electronic neutral substituents and iodine can be used as X-ray contrast agents. Also new iodoalkene compounds are described.Type: GrantFiled: September 6, 2000Date of Patent: June 18, 2002Assignee: Nycomed Imaging ASInventor: Hanno Priebe
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Publication number: 20010056213Abstract: A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF3)2CHOCH2Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF3)2CHOCH2F.Type: ApplicationFiled: June 21, 1999Publication date: December 27, 2001Inventor: ROSS C. TERRELL
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Patent number: 6316636Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.Type: GrantFiled: February 28, 1996Date of Patent: November 13, 2001Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Patent number: 6303831Abstract: A method for fluoromethylation of a halogenated alcohol. The method includes refluxing a halogenated alcohol with a dihalomethane under basic conditions in a first solvent to form a halomethyl ether and fluorinating the halomethyl ether in the presence of a fluorinating agent.Type: GrantFiled: June 1, 2000Date of Patent: October 16, 2001Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna
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Patent number: 6300532Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.Type: GrantFiled: December 15, 1998Date of Patent: October 9, 2001Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Timothy Rech Demmin
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Patent number: 6277867Abstract: The invention relates to compounds of general formula (I), their optically active isomers and salts wherein Ar=alycylic, aromatic or one or more heteroatom containing heterocyclic moiety, optionally substituted by one or more alkoxy-, methylenedioxy-, alkyl-, halogen-, haloalkyl-,or nitro- group and/or condensed with a benzene ring. Ar—(CR1R2)m—(YR3R4)n—X—(CR5R6)o—(CR7R8)p—C≡C—E (I) The compounds of general formula (I) according to the invention can be applied as active ingredients of pesticides, preferably arthropodicide compositions, and as synergists of other arthropodicideactive ingredients.Type: GrantFiled: August 31, 1998Date of Patent: August 21, 2001Assignee: Chinoin Gyogyszer es VegyeszetiInventors: Geza Arvai, Ildiko Bakonyvari, Bela Bertok, Laszlo Csiz, Iren Czudor, Zsuzsa R. Kuruczne, Laszlo Pap, Istvan Szekely
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Patent number: 6271422Abstract: A method for fluoromethylation of an alcohol via halogenative decarboxylation. The method includes the step of reacting an alcohol of the formula R1C(CX3)2OH with an alpha-haloester of the formula X2CH2CO2R2 to form an alpha-alkoxy ester, wherein R1 is selected from the group consisting of hydrogen and alkyl groups, wherein R2 is selected from the group consisting of hydrogen and alkyl groups, wherein X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine, and wherein X2 is selected from the group consisting of bromine and chlorine. The resulting alpha-alkoxy ester is saponified to form an alpha-alkoxy acid which is heated at reflux with lead tetraacetate and a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is converted to a fluoride compound of the formula R1C(CX3)2OCH2F with a fluorinating agent.Type: GrantFiled: June 1, 2000Date of Patent: August 7, 2001Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
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Patent number: 6100434Abstract: A method for synthesizing fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether. The method includes the step of combining in the presence of aluminum trichloride a quantity of hexafluoroisopropanol and a quantity of either 1,3,5-trioxane or paraformaldehyde to produce sevochlorane. The resulting sevochlorane is then combined with an alkali metal fluoride to produce fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether.Type: GrantFiled: March 26, 1999Date of Patent: August 8, 2000Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
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Patent number: 6046368Abstract: Briefly, in one aspect, this invention provides a catalytic method of preparation of primary and secondary hydrofluoroethers, the process comprising reacting a fluorinated precursor material and an alkylating agent in the presence of a Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts.Type: GrantFiled: March 17, 1998Date of Patent: April 4, 2000Assignee: 3M Innovative Properties CompanyInventors: William M. Lamanna, Richard M. Flynn, Daniel R. Vitcak, Zai-Ming Qiu
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Patent number: 5965779Abstract: The present invention provides processes for preparing 2,2,3,3,4-pentafluorooxetane and/or 2,2,3,3,4,4-hexafluorooxetane which comprises reacting 2,2,3,3-tetrafluorooxetane with fluorine gas, the process inhibiting decomposition of the oxetane ring during the reaction and producing a reduced amount of by-products.Type: GrantFiled: February 20, 1998Date of Patent: October 12, 1999Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Otsuka, Hirokazu Aoyama
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Patent number: 5910617Abstract: The process according to the invention consists in preparing chlorides of aliphatic or cycloaliphatic hydrocarbons by reacting the corresponding mono- or polyalcohol with phosgene or thionyl chloride in the presence of at least one catalyst chosen from hexasubstituted guanidinium halides and their hydrohalides, optionally grafted via one of their radicals to a silica-based support.The chlorides are quickly obtained with good yields and contain few by-products such as carbonates or chloroformates.Type: GrantFiled: June 18, 1998Date of Patent: June 8, 1999Assignee: Societe Nationale Des Poudres Et ExploisfsInventors: Loic Lecomte, Serge Metge, Denis Souyri
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Patent number: 5859052Abstract: Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitrites thereof.These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which x is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.Type: GrantFiled: March 27, 1998Date of Patent: January 12, 1999Assignee: G. D. Searle & Co.Inventors: Sean T. Nugent, Richard A. Mueller
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Patent number: 5750797Abstract: Briefly, in one aspect, this invention provides an improved alkylation process for the preparation of primary and secondary hydrofluoroether compounds, said process comprising:(1) combining in a polar, aprotic solvent:a) a fluorinated carbonyl-containing compound;b) an anhydrous source of fluoride ion;c) a tertiary or aromatic amine; andd) optionally, an effective amount of a phase transfer catalyst;(2) contacting the resulting mixture with an alkylating agent; and(3) recovering hydrofluoroether from the resulting product mixture.Type: GrantFiled: April 15, 1996Date of Patent: May 12, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Daniel R. Vitcak, Richard M. Flynn
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Patent number: 5637775Abstract: The invention relates to a process for the preparation of compounds of formula I ##STR1## wherein R is mono- or disubstituted lower alkyl, the substituents being selected from halogen and lower alkoxy, with the proviso that said substituents are not present at the carbon atom of the lower alkyl radical R linking the group R to the remainder of the molecule of formula I;R.sub.1 is hydrogen, lower alkyl, phenyl or phenyl-lower alkyl; andX is chloro or bromo;which comprises reacting an acetal of formula II, ##STR2## wherein R and R.sub.1 are as defined above,with at least one compound of formula R.sub.2 --X, wherein R.sub.2 is hydrogen or X--SO, in which last mentioned case the reaction mixture must contain a catalytically effective amount of N,N-di-lower alkyl-lower alkanoylamide(s) and wherein X is as defined with respect to the compounds of formula I. The compounds of formula I are useful intermediates, suitably for the synthesis of pharmaceutical or fungicidal compounds.Type: GrantFiled: April 26, 1995Date of Patent: June 10, 1997Assignee: Saurefabrik SchweizerhallInventors: Pasquale Gallegra, Gerhard Degischer
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Patent number: 5637780Abstract: This invention relates to methods for preparing alkylating agents and use of the agents prepared. In particular, this invention relates to preparation methods for hydroxy halide and organooxy halide alkylating agents and their use for alkylating cyclic urea compounds.Type: GrantFiled: June 30, 1994Date of Patent: June 10, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Prabhakar K. Jadhav, George C. Emmett, Michael E. Pierce
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Patent number: 5600022Abstract: In a reaction for introducing chloromethyl groups into an aromatic crosslinked copolymer by reacting chloromethyl methyl ether to the aromatic crosslinked copolymer in the presence of a chloromethylation reaction catalyst, a method for recovering chloromethyl methyl ether from the reaction mixture, which comprises the following steps 1) a step of adding to the reaction mixture an aqueous acid solution which is capable of dissolving the chloromethylation reaction catalyst without decomposing chloromethyl methyl ether, and an extraction solvent which is inert to and miscible with chloromethyl methyl ether and which is capable of swelling the chloromethylated aromatic crosslinked copolymer, 2) a step of contacting hydrogen chloride gas to the reaction mixture and the extract solution from the step 1 to convert decomposition products of chloromethyl methyl ether, to chloromethyl methyl ether, 3) a step of separating the resulting mixture from the step 2 into an extraction solvent layer containing chloromethyl metType: GrantFiled: December 27, 1994Date of Patent: February 4, 1997Assignee: Mitsubishi Chemical CorporationInventors: Kiyoto Ando, Akihiko Tsukada, Hiroshi Arataki, Youichi Tamura
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Patent number: 5576465Abstract: A process for preparing unsaturated ethers of the formula (1) ##STR1## from acetals or ketal of the formula (2) ##STR2## is improved by heating the acetals or ketals at from 100.degree. to 250.degree. C. in a high-boiling, branched carboxylic acid and obtaining the unsaturated ether as a distillate. The process, which is insensitive to contaminants, gives the unsaturated ether in high yields.Type: GrantFiled: June 2, 1995Date of Patent: November 19, 1996Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 5491145Abstract: Novel compound of the general formula: ##STR1## wherein R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, provided that either R.sup.2 or R.sup.3 is a hydrogen atom, the other being an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C=C-- group, form a 5- to 7-membered ring; X stands for an oxygen atom or S(O).sub.p (p stands for an integer from 0 to 2; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for a hydrogen atom, an optionally substituted lower lakyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.Type: GrantFiled: November 21, 1994Date of Patent: February 13, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
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Patent number: 5482650Abstract: Fluorine-containing liquid crystal compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portions being connected by a central core. The compounds have smectic or latent smectic mesophases.Type: GrantFiled: November 14, 1994Date of Patent: January 9, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5446211Abstract: The synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein (x+y) is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether in the presence of a solvent to form a chlorinated reaction product of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z wherein z is 1, 2 or 3. The process may also be carried out in the presence of oxygen in order to inhibit the formation of CF.sub.2 HOCCl.sub.3. The resulting compound(s) is then fluorinated with HF before or after separation, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.Type: GrantFiled: April 1, 1994Date of Patent: August 29, 1995Assignee: Hampshire Chemical Corp.Inventors: Gerald J. O'Neill, Robert J. Bulka
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Patent number: 5401886Abstract: Disclosed herein is a partially fluorinated polymer containing cyclic units. The polymer is particularly useful in for coatings and encapsulants. Also disclosed herein is the novel monomer from which the polymer is made, and a novel intermediate for that monomer.Type: GrantFiled: May 19, 1994Date of Patent: March 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 5260492Abstract: Disclosed herein are novel monomers of the formula CF.sub.2 .dbd.CF(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2, wherein n is 1, 2 or 3, and novel intermediates of the formula CF.sub.2 ClCFCl(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2 wherein n is 1, 2 or 3. Also disclosed is a fluoropolymer containing cyclic units when the monomer wherein n is 1 is free radically polymerized. The polymer is particularly useful in for coatings and encapsulants.Type: GrantFiled: December 21, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Bruce E. Smart, Zhen-Yu Yang
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Patent number: 5196611Abstract: The preparation of an alkyl, alkenyl, or alkynyl chloride by the reaction of a corresponding alcohol with phosgene or thionyl chloride in the presence of a phosphine oxide acting as catalyst, wherein the catalyst used is an aliphatic, cycloaliphatic, or cyclic/aliphatic phosphine oxide.Type: GrantFiled: May 6, 1992Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Irene Troetsch-Schaller, Thomas Wettling, Thomas-Michael Kahl, Leopold Hupfer, Wolfgang Franzischka, Hermann Koehler
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Patent number: 5196600Abstract: A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein the total x+y is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z, wherein z is 1, 2 or 3, which compound is then fluorinated with HF and/or an antimony salt and with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.Type: GrantFiled: March 25, 1992Date of Patent: March 23, 1993Assignee: W. R. Grace & Co.-Conn.Inventor: Gerald J. O'Neill
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Patent number: 5189227Abstract: 1,2,4-Trihalobutyl ethers of the formula ##STR1## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, which are useful as intermediates for the preparation of cyclopropanecarbaldehydes.Type: GrantFiled: August 30, 1990Date of Patent: February 23, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 5030785Abstract: Aromatic hydrocarbons are alkylated with relatively long chain alkylating agents, e.g., C.sub.6 + olefins, in the presence of, as catalyst, certain Lewis acid-promoted zeolites to provide long chain aromatic products which are useful, inter alia, as lubricating oil stocks.Type: GrantFiled: January 25, 1990Date of Patent: July 9, 1991Assignee: Mobil Oil Corp.Inventors: Albin Huss, Jr., Quang N. Le, Samuel A. Tabak, Stephen S. Wong
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Patent number: 4968836Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: January 30, 1990Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 4845268Abstract: A halogen-containing polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.2 --(CHClCF.sub.2 CF.sub.2 O).sub.b --(CCl.sub.2 CF.sub.2 CF.sub.2 O).sub.c --(CHFCF.sub.2 CF.sub.2 O).sub.d --(CFClCF.sub.2 CF.sub.2 O).sub.e --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.f --(I)wherein a, b, c, d, e and f are each an integer not less than 0 and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200and1.ltoreq.a+c+d+f,which may be prepared by ring-opening polymerizing 2,2,3,3-tetrafluorooxetane in the presence of an polymerization initiator to give a polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.a -- (II)wherein a is the same as defined above, and optionally fluorinating and/or chlorinating the polyether (II).Type: GrantFiled: December 9, 1986Date of Patent: July 4, 1989Assignee: Daikin Industries, Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
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Patent number: 4798906Abstract: Alkyl-, aryl- or alkylaryl-alkoxy halides are prepared by reacting the corresponding alcohol, phenol or alkyl phenol with ethylene oxide and/or propylene oxide in the presence of an amine catalyst to form an alkoxy alcohol, and directly reacting the latter with a halogenating agent in the continuing presence of the amine catalyst.Neutralization of the product and/or catalyst removal from the first stage is no longer necessary and reaction rates and yields are increased in the second stage.Type: GrantFiled: July 29, 1987Date of Patent: January 17, 1989Assignee: The British Petroleum Company p.l.c.Inventors: Philip K. G. Hodgson, Nevin J. Stewart
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Patent number: 4724092Abstract: A fluorine-containing grease composition comprising a halogen-containing polyether of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.a --(CHClCF.sub.2 CF.sub.2 O).sub.b --(CCl.sub.2 CF.sub.2 CF.sub.2 O).sub.c --(CHFCF.sub.2 CF.sub.2 O).sub.d --(CFClCF.sub.2 CF.sub.2 O).sub.e --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.f --(I)wherein a, b, c, d, e and f are each an integer not less than 0 and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200and,1.ltoreq.a+c+d+fand 0.5 to 60% by weight of a fluororesin base on the weight of the whole composition, which has good chemical and heat resistance and is used in a high temperature environment.Type: GrantFiled: November 7, 1985Date of Patent: February 9, 1988Assignee: Daikin Industries Ltd.Inventors: Shoshin Fukui, Shuhei Shimasaki, Takashi Tohzuka
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Patent number: 4714785Abstract: Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of a carbon catalyst for a time sufficient to convert the haloformate to the corresponding halide.Type: GrantFiled: September 15, 1986Date of Patent: December 22, 1987Assignee: PPG Industries, Inc.Inventor: James A. Manner
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Patent number: 4629814Abstract: This process relates to the preparation of unsubstituted or substituted bis-bromoalkyl ethers by reacting unsubstituted or substituted 1,3-dioxolane or unsubstituted or substituted 1,3-dioxane with thionyl bromide. The bis-bromoalkyl ethers made by this process can be used in preparing biologically active compounds.Type: GrantFiled: August 27, 1985Date of Patent: December 16, 1986Assignee: Rohm and Haas CompanyInventor: Michael P. James
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Patent number: 4622431Abstract: Organic chloroformate compounds are decomposed to their corresponding chlorides by heating the chloroformate, e.g., between 100.degree. and 175.degree. C., in the presence of a catalytic amount of solid poly(vinylpyridine), e.g., poly(4-vinylpyridine), for a time sufficient to convert the chloroformate to the corresponding chloride.Type: GrantFiled: April 4, 1985Date of Patent: November 11, 1986Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, Henry C. Stevens
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Patent number: 4605784Abstract: Disclosed is a process for the preparation of ether-containing chlorides by reacting an ether-alcohol, ether-glycol or ether-polyglycol with a chlorinating agent such as thionyl chloride in the presence of a catalytic amount of a quaternary ammonium salt, the reaction being conducted at a temperature of about 25.degree. C. to about 90.degree. C.Type: GrantFiled: July 18, 1985Date of Patent: August 12, 1986Assignee: Eastman Kodak CompanyInventors: Robert J. I. Eubanks, James G. Pacifici