Utilizing Unsaturated Compound Patents (Class 570/172)
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Patent number: 11491244Abstract: The present application is in the field of imaging reagents. In particular, the present application relates to labelled fluorocarbon imaging reagents, the preparation of the reagents, and their uses for imaging such as PET scanning.Type: GrantFiled: June 4, 2018Date of Patent: November 8, 2022Assignees: Sunnybrook Research Institute, McMaster UniversityInventors: John Valliant, Naomi Matsuura
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Patent number: 11332424Abstract: A process is provided comprising contacting and reacting the compound CF3CF2CHXCl, wherein X is H or Cl, or the compound CF3CF?CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF3CF?CH2 and CF3CH?CHF.Type: GrantFiled: September 18, 2020Date of Patent: May 17, 2022Assignee: THE CHEMOURS COMPANY FC, LLCInventor: Xuehui Sun
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Patent number: 10676414Abstract: A process for the manufacture of haloalkanes, or more particularly to a process for the manufacture of 1,1,1,3,3-pentachloropropane (HCC-240fa) and/or 1,1,1,3-tetrachloropropane (HCC-250fb). The process includes (a) mixing a catalyst, co-catalyst and a haloalkane starting material under conditions suitable to produce a homogeneous mixture; (b) reacting the homogeneous mixture with a haloalkene and/or alkene starting material under conditions suitable to produce a haloalkane product stream; and (c) recovering a haloalkane product from said product stream.Type: GrantFiled: August 21, 2017Date of Patent: June 9, 2020Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Ian Shankland
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Patent number: 9212110Abstract: The present invention provides a novel method for producing a mixture of fluoroalkyl iodides with high production efficiency, the method enabling the production of a desired fluoroalkyl iodide with high selectivity.Type: GrantFiled: March 12, 2013Date of Patent: December 15, 2015Assignee: DAIKIN INDUSTRIES, LTD.Inventor: Takeomi Hirasaka
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Patent number: 8957264Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.Type: GrantFiled: December 11, 2013Date of Patent: February 17, 2015Assignee: Asahi Glass Company, LimitedInventors: Shoji Furuta, Yusuke Sugahara, Keiko Nakase, Keisuke Mori
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Patent number: 8889924Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.Type: GrantFiled: February 4, 2013Date of Patent: November 18, 2014Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Andrew Joseph Poss, David Nalewajek
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Patent number: 8884084Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. Azeotropes of CClF2CH2CF3 with HF and azeotropes of CF3CH2CHF2 with HF are also disclosed; as are process for producing such azeotropes.Type: GrantFiled: April 1, 2011Date of Patent: November 11, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur N. Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 8791310Abstract: To provide a process for producing a fluoroalkyl iodide, whereby the selectivity for a fluoroalkyl iodide having a desired degree of polymerization is high and the productivity is high. A process for producing a fluoroalkyl iodide (2) represented by RfCF2CF2I (wherein Rf is a fluoroalkyl group having at most 4 carbon atoms), which comprises reacting a fluoroalkyl iodide (1) represented by RfI with tetrafluoroethylene in the presence of a radical initiator, wherein a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to the fluoroalkyl iodide (1), is followed by repeating (n?1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to a reaction mixture (1) formed in the first reaction step.Type: GrantFiled: December 4, 2012Date of Patent: July 29, 2014Assignee: Asahi Glass Company, LimitedInventors: Tetsuo Otsuka, Shoji Furuta
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Patent number: 8729321Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state is under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.Type: GrantFiled: April 19, 2006Date of Patent: May 20, 2014Assignee: Asahi Glass Company, LimitedInventors: Shoji Furuta, Yu{grave over (s)}uke Sugahara, Keiko Nakase, Keisuke Mori
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Publication number: 20140058141Abstract: A process is disclosed for producing addition compound CF3CCl2CH2CClXR, wherein X=H, F, Cl or Br, and R=H or a perhalogenated alkyl group, provided that X and R are not both H. The process involves a liquid phase reaction of 1,1,1-trichlorotrifluoroethane with CH2?CXR in the presence of an addition catalyst.Type: ApplicationFiled: November 7, 2011Publication date: February 27, 2014Inventors: Mario Joseph Nappa, Ekaterinan N. Swearingen, Sergei Rafailovich Sterlin
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Patent number: 8604257Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkane with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkane with hydrogen to produce a fluorine-containing olefin. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkanes comprising copper metal deposited on a support, and comprising palladium deposited on calcium fluoride, poisoned with lead and reducing the in the presence or absence of a dehydrochlorination catalyst under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336).Type: GrantFiled: May 19, 2011Date of Patent: December 10, 2013Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh, David Nalewajek, Haridasan K. Nair
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Patent number: 8530709Abstract: The present invention provides a method for the preparation of suitable chlorofluorocarbon and hydrochlorofluorocarbon materials or chlorofluorocarbon and hydrochlorofluorocarbon alkene and alkyne intermediates which serve as useful feedstock for fluorination and reduction to cis-1,1,1,4,4,4-hexafluoro-2-butene. Also presented is a continuous process for the production of cis-1,1,1,4,4,4-hexafluoro-2-butene from the alkene and alkyne intermediates.Type: GrantFiled: May 19, 2011Date of Patent: September 10, 2013Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, David Nalewajek, Michael Van Der Puy, Haridasan K. Nair
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Patent number: 8524104Abstract: Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where Rf is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.Type: GrantFiled: August 27, 2009Date of Patent: September 3, 2013Assignee: Ansul, IncorporatedInventor: Jeffrey D. Michael
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Publication number: 20130131403Abstract: Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa?m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a?m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).Type: ApplicationFiled: January 22, 2013Publication date: May 23, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: Honeywell International Inc.
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Patent number: 8314273Abstract: A process for making HFC-236cb is disclosed. The process comprises reacting TFE with HFC-32 in the presence of at least one co-product and a suitable catalyst to produce a product mixture comprising HFC-236cb, wherein the total amount of the at least one co-product is at least 10 ppmv based on the total amount of the tetrafluoroethylene, the difluoromethane and the at least one co-product.Type: GrantFiled: September 4, 2007Date of Patent: November 20, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Barry Asher Mahler, Xuehui Sun, Velliyur Nott Mallikarjuna Rao
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Patent number: 8258353Abstract: The present invention provides one-step processes for the production of chlorinated and/or fluorinated propenes. The processes provide good product yield with low, e.g., less than about 20%, or even less than 10%, concentrations of residues/by-products. Advantageously, the processes may be conducted at low temperatures relative to conventional processes, so that energy savings are provided, and/or at higher pressures so that high throughputs may also be realized. The use of catalysts may provide enhancements to conversion rates and selectivity over those seen in conventional processes, as may adjustments to the molar ratio of the reactants.Type: GrantFiled: April 20, 2010Date of Patent: September 4, 2012Assignee: Dow Global Technologies, LLCInventors: William J. Kruper, Jr., Max M. Tirtowidjojo, Kurt F. Hirsekorn, Debashis Chakraborty, Juergen Eiffler
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Patent number: 8247625Abstract: A process is disclosed for making RR1R2CCR1R2F wherein R is selected from the group consisting of CH3, CH2F, C2H4F, and F(CF2)nCH2CH2 where n is an integer from 1 to 10, each R1 is independently selected from the group consisting of H, Cl, F and CF3, and each R2 is independently selected from the group consisting of H, F and CF3. The process involves reacting RF with R1R2C?CR1R2 in the presence of SbF5 to produce a product mixture comprising RR1R2CCR1R2F, wherein the reaction temperature is from about ?60° C. to about ?10° C., provided that total number of carbon atoms in R1R2C?CR1R2 is 5 or less.Type: GrantFiled: July 3, 2007Date of Patent: August 21, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Xuehui Sun, Viacheslav A. Petrov, Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Ekaterina N. Swearingen
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Patent number: 8232434Abstract: A novel process for producing a fluoroalkyl iodide telomer is provided, which is able to obtain a fluoroalkyl iodide telomer having a desired chain length, efficiently. A fluoroalkyl iodide represented by the general formula RfI (wherein Rf is a C1-10 fluoroalkyl group) and tetrafluoroethylene are used as a telogen and a taxogen, respectively. These compounds are supplied to a distillation apparatus. In a reaction zone located in an intermediate part of the distillation apparatus, the compounds are subjected to a telomerization reaction in the presence of a metal catalyst with heating to generate a fluoroalkyl iodide telomer represented by the general formula Rf(CF2CF2)nI (wherein Rf is the same as defined above and n is an integer of 1-4). Thereafter, a fraction comprising the fluoroalkyl iodide telomer is separated by distillation.Type: GrantFiled: March 30, 2009Date of Patent: July 31, 2012Assignee: Daikin Industries, Ltd.Inventors: Takeomi Hirasaka, Yoshinori Tanaka
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Patent number: 8088959Abstract: A process is disclosed for the conversion of fluorocarbons into fluorinated unsaturated compounds useful as monomers or other chemical precursors, such as C2H2F2. The process comprises reacting a hydrocarbon feed (20) arid a fluorocarbon feed (10) in a high temperature reactor (26), at sufficiently high temperature and sufficiently short resident time to form product mixture (28) having the fluorinated unsaturated compound as the major reaction product, and cooling (18) to a temperature sufficiently low to inhibit polymerisation of the unsaturated compound. The reaction product may then be processed by removal of higher molecular weight compounds (35) and acids (32) and optionally separated (44) into product components.Type: GrantFiled: March 22, 2011Date of Patent: January 3, 2012Assignee: Pacifitech Pty LimitedInventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
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Patent number: 8071826Abstract: A process for the preparation of 2,3,3,3-tetrafluoropropene (HFO-1234yf). HFO-1234yf is a refrigerant with low global warming potential. A process comprises a) reacting chlorotrifluoroethylene with a methyl halide to form an intermediate product stream; and b) reacting the intermediate product stream with hydrogen fluoride to thereby produce a result comprising 2,3,3,3-tetrafluoropropene.Type: GrantFiled: February 24, 2009Date of Patent: December 6, 2011Assignee: Honeywell International Inc.Inventor: Michael Van Der Puy
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Patent number: 7951983Abstract: A process for the insertion of a fluorinated olefin into a fluorinated iodide in the presence of a nickel catalyst at a temperature of a maximum of 150° C. with an initial rate of 0.04 mole/hour without loss of selectivity is disclosed.Type: GrantFiled: November 4, 2009Date of Patent: May 31, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Sheng Peng, Kenneth Gene Moloy
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Patent number: 7928272Abstract: A process is disclosed for the conversion of fluorocarbons into fluorinated unsaturated compounds useful as monomers or other chemical precursors, such as C2H2F2. The process comprises reacting a hydrocarbon feed (20) and a fluorocarbon feed (10) in a high temperature reactor (26), at sufficiently high temperature and sufficiently short resident time to form a reaction product mixture (28) having the fluorinated unsaturated compound as the major reaction product, and cooling (18) to a temperature sufficiently low to inhibit polymerization of the unsaturated compound. The reaction product may then be processed by removal of higher molecular weight compounds (35) and acids (32) and optionally separated (44) into product components.Type: GrantFiled: September 14, 2009Date of Patent: April 19, 2011Assignee: Pacifitech Pty LimitedInventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
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Patent number: 7888538Abstract: A process for the insertion of a partially fluorinated olefin into a fluorinated iodide in the presence of a nickel catalyst at a temperature of a maximum of 150° C. with an initial rate of 0.01 mole/hour without loss of selectivity is disclosed, as well as use of the process for insertion of a perfluorinated olefin with an initial rate of 0.04 mole/hour.Type: GrantFiled: November 4, 2009Date of Patent: February 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Sheng Peng, Kenneth Gene Moloy
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Publication number: 20100305371Abstract: A process for making HFC-236cb is disclosed. The process comprises reacting TFE with HFC-32 in the presence of at least one co-product and a suitable catalyst to produce a product mixture comprising HFC-236cb, wherein the total amount of the at least one co-product is at least 10 ppmv based on the total amount of the tetrafluoroethylene, the difluoromethane and the at least one co-product.Type: ApplicationFiled: September 4, 2007Publication date: December 2, 2010Applicant: E.I.DU PONT NEMOURS AND COMPANYInventors: Barry Asher Mahler, Xuehui Sun, Velliyur Nott Mallikarjuna Rao
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Publication number: 20100197981Abstract: A process is disclosed for making CH2ClCF2CClF2. The process involves reacting CH2ClF with CClF?CF2 in an addition reaction zone in the presence of an aluminum halide composition having a bulk formula of AlClxBryF3-x-y wherein the average value of x is 0 to 3, the average value of y is 0 to 3?x, provided that the average values of x and y are not both 0. Also disclosed is a process for making CH2FCF2CF3 that involves reacting the CH2ClCF2CClF2 with HF in a fluorination reaction zone in the presence of a fluorination catalyst. Also disclosed is a process for making CHF?CFCF3 that involves dehydrofluorinating the CH2FCF2CF3.Type: ApplicationFiled: September 5, 2007Publication date: August 5, 2010Inventor: Allen Capron Sievert
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Publication number: 20100076231Abstract: A process is disclosed for making CH2?CFCF3. The process involves contacting CH2ClCF2CF3 with H2 in a reaction zone in the presence of a catalyst including a catalytically effective amount of palladium supported on a support selected from chromium oxide, fluorinated chromium oxide, chromium fluoride, aluminum oxide, aluminum fluoride and/or fluorinated alumina, to produce CH2?CFCF3. The mole ratio of H2 to the CH2ClCF2CF3 fed to the reaction zone is between about 1:1 and about 4:1.Type: ApplicationFiled: October 31, 2007Publication date: March 25, 2010Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Publication number: 20090299108Abstract: A process is disclosed for making RR1R2CCR1R2F wherein R is selected from the group consisting of CH3, CH2F, C2H4F, and F(CF2)nCH2CH2 where n is an integer from 1 to 10, each R1 is independently selected from the group consisting of H, Cl, F and CF3, and each R2 is independently selected from the group consisting of H, F and CF3. The process involves reacting RF with R1R2C?CR1R2 in the presence of SbF5 to produce a product mixture comprising RR1R2CCR1R2F, wherein the reaction temperature is from about ?60° C. to about ?10° C., provided that total number of carbon atoms in R1R2C?CR1R2 is 5 or less.Type: ApplicationFiled: July 3, 2007Publication date: December 3, 2009Applicant: E.I. DU PONT ED NEMOURS AND COMPANYInventors: Xuehui Sun, Viacheslav A. Petrov, Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Ekaterina N. Swearingen
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Patent number: 7601878Abstract: A solid catalyst used in, for example, production of a perfluoroalkyl iodide telomer is effectively and continuously recovered and the recovered catalyst is continuously recycled to the reactor for reuse. A slurry containing a reaction product and the catalyst is drawn from the reaction system, and the catalyst in the drawn slurry is classified by means of a hydrocyclone, whereby a high-concentration slurry whose catalyst concentration is higher than that of the drawn slurry and a low-concentration slurry whose catalyst concentration is lower than that of the drawn slurry are obtained, and the high-concentration slurry is recycled to the reaction system.Type: GrantFiled: March 16, 2007Date of Patent: October 13, 2009Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Hirata, Kouzou Noda, Jun Miki
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Patent number: 7557254Abstract: A method for preparing fluorinated organic compounds wherein at least one fluorinated olefin is reacted with methyl fluoride in the gas-phase and in the presence of a Lewis Acid catalyst to form at least one product having at least 3 carbon atoms.Type: GrantFiled: June 6, 2008Date of Patent: July 7, 2009Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung, Haridasan Nair, Jingji Ma
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Patent number: 7504358Abstract: A crystalline alpha-chromium oxide where from about 0.05 atom % to about 2 atom % of the chromium atoms in the alpha-chromium oxide lattice are substituted by nickel atoms, and optionally, additional chromium atoms in the alpha-chromium oxide lattice are substituted by trivalent cobalt atoms (provided that the total amount of the nickel atoms and the trivalent cobalt atoms in the alpha-chromium oxide lattice is no more than 6 atom %) is disclosed. Also disclosed is a chromium-containing catalyst composition comprising as a chromium-containing component the crystalline substituted alpha-chromium oxide; and a method for preparing a composition comprising the crystalline substituted alpha-chromium oxide.Type: GrantFiled: August 21, 2003Date of Patent: March 17, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen C. Sievert, Shekhar Subramoney, Munirpallam Appadorai Subramanian
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Patent number: 7396965Abstract: A method for preparing fluorinated organic compounds wherein at least one fluorinated olefin is reacted with methyl fluoride in the gas-phase and in the presence of a Lewis Acid catalyst to form at least one product having at least 3 carbon atoms.Type: GrantFiled: May 12, 2005Date of Patent: July 8, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, HsuehSung Tung, Haridasan Nair, Jingji Ma
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Patent number: 7371904Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene which comprises, in one embodiment, reacting a compound of CF3X1 with a compound of CX2H?CHX3, wherein X1, X2, and X3 are each independently selected from the group consisting of fluorine, chlorine, bromine and iodine, to produce a reaction product comprising a compound of CF3CH?CHX3, wherein X3 is as described above; and when X3 is not fluorine, fluorinating the compound to produce 1,3,3,3-tetrafluoropropene. The process in another embodiment comprises preparing tetrafluoropropene comprising thermally cracking one or more compounds capable of producing a reaction mixture which preferably comprises diflurocarbene radicals and vinylidene fluoride, and converting said reaction mixture into—tetrafluoropropene (1,3,3,3-tetrafluoropropene).Type: GrantFiled: April 29, 2005Date of Patent: May 13, 2008Assignee: Honeywell International Inc.Inventors: Jing Ji Ma, Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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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: 7214815Abstract: The present invention provides a metallic copper catalyst for use in an ethylene addition reaction to polyfluoroalkyl iodides, a process for efficiently producing a polyfluoroalkylethyl iodide using such a metal copper catalyst in an ethylene addition reaction to a polyfluoroalkyl iodide, and a process for efficiently producing a polyfluoroalkylethyl iodide from a polyfluoroalkyl iodide using the same metallic copper catalyst in a telomerization reaction and a subsequent ethylene addition reaction.Type: GrantFiled: June 17, 2003Date of Patent: May 8, 2007Assignee: Daikin Industries, Ltd.Inventors: Yoshirou Funakoshi, Jun Miki
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Patent number: 7109386Abstract: Process for the preparation of a halogenated olefin by reaction of an alkyne and/or of an allene compound with a hydrogen halide in a liquid medium comprising at least one hydrohalogenation catalyst comprising at least one palladium compound.Type: GrantFiled: March 20, 2002Date of Patent: September 19, 2006Assignee: Solvay (Societe Anonyme)Inventor: Véronique Mathieu
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Patent number: 7102041Abstract: A process for preparing a haloalkane comprising: (a) contacting a haloalkane starting material with an alkene in the presence of an effective amount of a catalyst complex under conditions effective to facilitate an addition reaction and to form a product stream comprising a haloalkane product from the addition reaction, wherein the catalyst complex has a boiling point higher than that of the haloalkane product; and (b) recovering the haloalkane product from the product stream.Type: GrantFiled: December 8, 2004Date of Patent: September 5, 2006Assignee: Honeywell International Inc.Inventor: Hsueh Sung Tung
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Patent number: 7094934Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.Type: GrantFiled: January 31, 2001Date of Patent: August 22, 2006Assignee: Daikin Industries, Ltd.Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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Patent number: 7094936Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.Type: GrantFiled: October 16, 2003Date of Patent: August 22, 2006Assignee: Great Lakes Chemical CorporationInventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
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Patent number: 7074434Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: October 29, 2002Date of Patent: July 11, 2006Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Vincent Wilmet
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Patent number: 7053253Abstract: Perfluoro-4-methyl-2-pentene containing the undesirable perfluoro-2-methyl-2-pentene may be purified by contacting the mixture with at least a stoichiometric equivalent of an aqueous inorganic base (relative to the perfluoro-2-methyl-2-pentene), in the presence of a polar solvent.Type: GrantFiled: May 2, 2005Date of Patent: May 30, 2006Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu
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Patent number: 7038095Abstract: A mixture of fluoroalkyl iodide telomers represented by the formula: Rf(CF2CF2)nI wherein Rf represents a fluoroalkyl group whose number of carbon atoms is in the range of 1 to 10, with the polymerization degree n equal to or more than k that is an integer of 3 or more, is obtained by reacting a fluoroalkyl iodide with tetrafluoroethylene in a first reactor followed by fractionating a first reaction mixture which contains fluoroalkyl iodide telomers of low polymerization degree, as well as by reacting the telomer with n of (k?1) separated from the first reaction mixture with tetrafluoroethylene in the second reactor.Type: GrantFiled: February 5, 2002Date of Patent: May 2, 2006Assignee: Daikin Industries, Ltd.Inventors: Yukio Homoto, Kunitada Tanaka
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Patent number: 6958422Abstract: The present invention relates to the pyrolysis of hydrochlorofluorocarbons to form fluoromonomers such as tetrafluoroethylene, the pyrolysis being carried out in a reaction zone lined with nickel and mechanically supported by a jacket of other corrosion resistant metal, the nickel lining providing an improved yield of valuable reaction products.Type: GrantFiled: December 17, 2003Date of Patent: October 25, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
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Patent number: 6924403Abstract: The present invention relates to the process of pyrolyzing tetrafluoroethylene to hexafluoropropylene by carrying out the pyrolysis in a tubular reactor that is lined with either nickel or nickel alloy which contains no greater than 8 wt % chromium.Type: GrantFiled: May 7, 2003Date of Patent: August 2, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: John James Barnes, Kenneth Paul Kelch, Thomas D. Sandbrook, David John Van Bramer
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Patent number: 6919490Abstract: The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160° C. under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.Type: GrantFiled: April 17, 2002Date of Patent: July 19, 2005Assignee: Daikin Industries, Ltd.Inventors: Yoshio Funakoshi, Jun Miki
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Patent number: 6858763Abstract: The present invention relates to a process for preparing an elastomeric ethylene-hexafluoropropylene copolymer with excellent vulcanization properties, which comprises emulsion polymerizing ethylene, hexafluoropropylene and when in demand, a monomer copolymerizable therewith in a aqueous medium at a low temperature of ?20° C. to 40° C. using a radical polymerization initiator.Type: GrantFiled: September 19, 2001Date of Patent: February 22, 2005Assignee: Daikin Industries, Ltd.Inventors: Mitsuo Tsukamoto, Masao Otsuka, Mitsuhiro Otani, Tatsuya Morikawa, Hideya Saito
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Publication number: 20040249225Abstract: A solid catalyst used in, for example, production of a perfluoroalkyl iodide telomer is effectively and continuously recovered and the recovered catalyst is continuously recycled to the reactor for reuse. A slurry containing a reaction product and the catalyst is drawn from the reaction system, and the catalyst in the drawn slurry is classified by means of a hydrocyclone, whereby a high-concentration slurry whose catalyst concentration is higher than that of the drawn slurry and a low-concentration slurry whose catalyst concentration is lower than that of the drawn slurry are obtained, and the high-concentration slurry is recycled to the reaction system.Type: ApplicationFiled: April 22, 2004Publication date: December 9, 2004Inventors: Tatsuya Hirata, Kouzou Noda, Jun Miki
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Publication number: 20040116753Abstract: The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160° C. under a pressure of 0.1 to 5 MPa (gauge pressure).Type: ApplicationFiled: October 9, 2003Publication date: June 17, 2004Inventors: Yoshio Funakoshi, Jun Miki
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Publication number: 20040102665Abstract: The present invention involves a process for the manufacture of &agr;, &ohgr;-diiodoperfluoroalkanes of the formula I—(CF2CF2)n—I, wherein n is an integer between 2 and 6. The latter compounds are produced at relatively high conversions and under relatively mild reaction temperatures and pressures, compared to prior art processes, by the elimination of the gaseous byproduct perfluorocyclobutane throughout the process.Type: ApplicationFiled: November 21, 2002Publication date: May 27, 2004Inventors: Hasan Dindi, John Joseph Hagedorn, Ming-Hong Hung
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Patent number: 6730817Abstract: 1,1,1,3,3-Pentafluoropropane is produced by reaction between 1,1,1,3,3-pentachloropropane and hydrogen fluoride in the presence of a hydrofluorination catalyst. The 1,1,1,3,3-pentachloropropane may advantageously be obtained by reaction between vinyl chloride and tetrachloromethane in the presence of a telomerization catalyst and of a nitrile.Type: GrantFiled: June 8, 1998Date of Patent: May 4, 2004Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens, Jean-Paul Schoebrechts
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Patent number: 6720466Abstract: A process for economically producing 1,1,1,3,3-pentachloropropane under conditions which preserve the activity of the catalyst. In a preferred embodiment, a two-stage distillation process is employed. In the two-stage process, the size of the equipment, temperature and vacuum are varied.Type: GrantFiled: April 17, 2002Date of Patent: April 13, 2004Assignee: Vulcan Chemicals Division of Vulcan Materials CompanyInventors: Richard L. Wilson, John L. Dawkins, Rodney L. Klausmeyer, James J. Weller