Catalyst Utilized Patents (Class 570/156)
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Patent number: 9193649Abstract: There is provided a method and an apparatus for efficiently obtaining 2,3,3,3-tetrafluoropropene with low contents of both organic impurities and water. The method for continuously purifying crude 2,3,3,3-tetrafluoropropene containing water and one or more organic impurities, the method including using an apparatus having a distillation column with X stages (3?X, the stage closest to a column top is the first stage) and a unit for cooling and condensing a distillate; supplying the crude 2,3,3,3-tetrafluoropropene to an m-th stage (n+1?m?X, 2?n?X?1) of the distillation column, recirculating at least part of the distillate cooled and condensed in the unit for cooling and condensing to an h-th stage (1?h?n?1) of the distillation column; and taking out a liquid phase part of an n-th stage of the distillation column to obtain a purified product of 2,3,3,3-tetrafluoropropene.Type: GrantFiled: June 16, 2014Date of Patent: November 24, 2015Assignee: ASAHI GLASS COMPANY, LIMITEDInventors: Satoshi Kawaguchi, Hirokazu Takagi, Masaaki Tsuzaki, Masato Fukushima, Hidekazu Okamoto
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Patent number: 9181151Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: GrantFiled: September 9, 2013Date of Patent: November 10, 2015Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
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Patent number: 9162946Abstract: The invention relates to a process for preparing a C3-6 (hydro)fluoroalkene comprising dehydrohalogenating a C3-6 hydro(halo)fluoroalkane in the presence of a zinc/chromia catalyst, wherein the C3-6 (hydro)fluoroalkene produced is isomerised in the presence of the zinc/chromia catalyst.Type: GrantFiled: October 1, 2013Date of Patent: October 20, 2015Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, Leslie Richard Seddon
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Patent number: 9115042Abstract: Provided are a fluorination catalyst for preparing 2,3,3,3-tetrafluoropropene and a method using the catalyst for preparing 2,3,3,3-tetrafluoropropene. The catalyst has the following structural formula: Crx(Y,Z)0.005-0.5O0.1-1.0F1.0-3.0, where Y is one or a combination of two or more among Al, Zn, and Mg, and where Z is a rare earth element having an oxygen-storing/releasing function. The catalyst has in preparing 2,3,3,3-tetrafluoropropene the advantages of increased raw material conversion rate, great product selectivity, and extended catalyst service life.Type: GrantFiled: September 11, 2012Date of Patent: August 25, 2015Assignees: SINOCHEM LANTIAN CO., LTD., SINOCHEM MODERN ENVIRONMENTAL PROTECTION CHEMICALS (XI'AN) CO., LTD.Inventors: Gang Yang, Lei Xu, Huie Yang, En Jiang, Jianping Fan, Xintang Zhao, Changhua Zeng, Wenqing Zhang, Yunlong Lei, Zhong Li, Shukang Chen
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Patent number: 9090529Abstract: The present invention has an object of providing a method for producing 1,2-dichloro-3,3,3-trifluoropropene by a vapor-phase reaction easily and in an industrial scale. A method for producing 1,2-dichloro-3,3,3-trifluoropropene of the present invention includes putting 1,2-dichloro-1-halogeno-3,3,3-trifluoropropane with an activated carbon catalyst in a vapor phase. According to the present invention, 1,2-dichloro-3,3,3-trifluoropropene is produced in an industrial scale at a high yield by use of 1,2-dichloro-1-halogeno-3,3,3-trifluoropropane, which is available at low cost, as a material.Type: GrantFiled: March 19, 2015Date of Patent: July 28, 2015Assignee: CENTRAL GLASS COMPANY, LIMITEDInventors: Yoshio Nishiguchi, Satoru Okamoto, Fuyuhiko Sakyu
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Patent number: 9079819Abstract: A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.Type: GrantFiled: April 2, 2013Date of Patent: July 14, 2015Assignee: Central Glass Company, LimitedInventors: Satoshi Yoshikawa, Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
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Patent number: 9040760Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.Type: GrantFiled: October 27, 2011Date of Patent: May 26, 2015Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Patent number: 9029617Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).Type: GrantFiled: July 14, 2014Date of Patent: May 12, 2015Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
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Patent number: 9018428Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.Type: GrantFiled: March 14, 2013Date of Patent: April 28, 2015Assignee: Honeywell International Inc.Inventor: Stephen A. Cottrell
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Patent number: 9012702Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.Type: GrantFiled: February 10, 2012Date of Patent: April 21, 2015Assignee: E. I. du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa
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Publication number: 20150105595Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: ApplicationFiled: December 15, 2014Publication date: April 16, 2015Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 9000241Abstract: The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.Type: GrantFiled: October 20, 2011Date of Patent: April 7, 2015Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
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Patent number: 9000239Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.Type: GrantFiled: March 14, 2013Date of Patent: April 7, 2015Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20150094432Abstract: The present invention relates to the preparation of trifluoroethylene (VF3 or TrFE) by hydrogenolysis of chlorotrifluoroethylene (CTFE) in the gaseous phase over a group VIII metal catalyst deposited on a support. This method can be used to obtain VF3 in an economical manner in conditions which minimize the risk of explosion of this molecule. Using a catalyst containing a group VIII metal and, more specifically, containing Pd deposited on a support and a specific series of steps of separation and purification makes it possible to obtain excellent CTFE conversion rates and high selectivity in VF3 at atmospheric pressure and at low temperatures.Type: ApplicationFiled: February 22, 2013Publication date: April 2, 2015Applicant: ARKEMA FRANCEInventors: Philippe Leduc, Thierry Lannuzel, Dominique Garrait, Serge Hub, Emmanuel Guiraud, Fabrice Domingues Dos Santos
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Patent number: 8987532Abstract: Disclosed is a process for producing 1,2-dichloro-3,3,3-trifluoropropene, which is characterized by that 1-halogeno-3,3,3-trifluoropropene represented by the general formula [1]: (In the formula, X represents a fluorine atom, chlorine atom or bromine atom.) is reacted with chlorine in a gas phase in the presence of a catalyst. It is possible by this process to produce 1,2-dichloro-3,3,3-trifluoropropene in an industrial scale with good yield by using 1-halogeno-3,3,3-trifluoropropene, which is available with a low price, as the raw material.Type: GrantFiled: April 1, 2014Date of Patent: March 24, 2015Assignee: Central Glass Company, LimitedInventors: Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
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Publication number: 20150080618Abstract: A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.Type: ApplicationFiled: April 2, 2013Publication date: March 19, 2015Inventors: Satoshi Yoshikawa, Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
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Publication number: 20150080617Abstract: Disclosed is a method for preparing a metal fluoride catalyst as a dehydrofluorination catalyst having high activity under a mild condition using a trifluoroacetic acid solution with no use of HF gas having fluidity and corrosive property. Disclosed also is a dehydrofluorination method for preparing HFO-1225ye from HFP-236ea by using the catalyst with high efficiency.Type: ApplicationFiled: September 3, 2014Publication date: March 19, 2015Applicant: Korea Institute of Science and TechnologyInventors: Hilman Hutama, Jeong-Myeong HA, Chang Soo KIM, Hong Gon KIM, Jae Wook CHOI, Dong Jin SUH, Hyun Joo LEE, Byoung Sung AHN
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Patent number: 8975454Abstract: The instant invention relates to a process and method for manufacturing 2,3,3,3-tetrafluoropropene by dehydrohalogenating a reactant stream of 2-chloro-1,1,1,2-tetrafluoropropane that is substantially free from impurities, particularly halogenated propanes, propenes, and propynes.Type: GrantFiled: October 25, 2011Date of Patent: March 10, 2015Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
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Patent number: 8969057Abstract: Methods or preparing para-xylene from biomass by carrying out a Diels-Alder cycloaddition at controlled temperatures and activity ratios. Methods of preparing bio-terephthalic acid and bio-poly(ethylene terephthalate (bio-PET) are also disclosed, as well as products formed from bio-PET.Type: GrantFiled: April 22, 2013Date of Patent: March 3, 2015Assignee: The Coca-Cola CompanyInventors: Indra Prakash, Venkata Sai Prakash Chaturvedula, Robert M. Kriegel, Xiaoyan Huang Huang
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Publication number: 20150057472Abstract: The invention relates to the use of a liquid-vapor separator such as a de-entrainer to remove an unvaporized portion of a feed, e.g. 1,1,2,3-tetrachloropropene (1230xa), to a catalytic vapor phase fluorination reaction where e.g. 2-chloro-3,3,3,-trifluoropropene (1233xf) is produced. The invention extends the life of the catalyst.Type: ApplicationFiled: April 18, 2014Publication date: February 26, 2015Applicant: Honeywell International Inc.Inventors: Selma Bektesevic, Haluk Kopkalli, Haiyou Wang
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Publication number: 20150045589Abstract: Provided is a palladium on carbon (Pd/C) catalyst obtained by using an ionic liquid, a method for preparing the same, and a method for hydrogenation of hydrofluorocarbon using the same. More particularly, palladium particles are supported on carbon particles by using an ionic liquid, and the resultant Pd/C catalyst is used for hydrogenation of hydrofluorocarbon. The catalyst includes palladium particles having a smaller particle size and a more uniform shape as compared to the existing Pd/C catalysts, and thus shows high catalytic activity.Type: ApplicationFiled: October 21, 2013Publication date: February 12, 2015Applicant: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGYInventors: Chang Soo KIM, Kyesang YOO, Byoung Sung AHN, Hyun Joo LEE, Jeong Myeong HA, Hong Gon KIM
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Publication number: 20150045590Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).Type: ApplicationFiled: July 14, 2014Publication date: February 12, 2015Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
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Patent number: 8952208Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: GrantFiled: June 28, 2010Date of Patent: February 10, 2015Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Daniel C. Merkel
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Patent number: 8940948Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.Type: GrantFiled: July 17, 2013Date of Patent: January 27, 2015Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20150017064Abstract: A trifluoroethylene composition which is safe to handle and which can be safely stored and transported at pressures of up to 5.00 MPa. The composition comprises trifluoroethylene and HCl in a molar ratio trifluoroethylene:HCl from 10:90 to 63:37. When the composition is a compressed gas it has a pressure of from 0.50 to 5.00 MPa.Type: ApplicationFiled: January 31, 2013Publication date: January 15, 2015Inventor: Emanuela Antenucci
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Publication number: 20150011806Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride, characterized in that the concentrations of respective catalytic components in the 1,1,1,3,3-pentachloropropane as the raw material is controlled to a predetermined level or less. By controlling the concentrations of the respective catalytic components in the 1,1,1,3,3-pentachloropropane to the predetermined level or less, it is possible to improve the problems of shortening of catalyst life, retardation of reaction and scaling or corrosion of equipment in the production of the 1-chloro-3,3,3-trifluoropropene. In addition, the 1,1,1,3,3-pentachloropropane can be obtained selectively with high yield by telomerization reaction of carbon tetrachloride and vinyl chloride. The present invention is thus useful as the method for industrially advantageous, high-yield production of the 1-chloro-3,3,3-trifluoropropene.Type: ApplicationFiled: November 22, 2012Publication date: January 8, 2015Applicant: Central Glass Company, LimitedInventors: Yasuo Hibino, Satoshi Yoshikawa, Fuyuhiko Sakyu
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Patent number: 8927791Abstract: The current invention relates to a process for making a tetrafluoropropene using a tetrafluorochloropropane and/or a pentafluoropropane as starting or intermediate reagents. More specifically, though not exclusively, the present invention relates to a novel method for preparing a tetrafluoropropene by dehydrohalogenating a starting or intermediate tetrafluorochloropropane and/or pentafluoropropane material in the presence of a caustic solution at a temperature range greater than 40° C. and less than or equal to 80° C.Type: GrantFiled: March 28, 2011Date of Patent: January 6, 2015Assignee: Honeywell International Inc.Inventors: Selma Bektesevic, Hsueh S. Tung, Haiyou Wang, Daniel C. Merkel, Robert C. Johnson
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Publication number: 20150005536Abstract: A method for forming 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising providing a dehydrochlorination starting material having relatively low concentrations of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), especially and preferable less than about 8.0% when the dehydrochlorination reaction utilizes no substantial amount of catalyst or catalyst comprising austenitic nickel-based materials.Type: ApplicationFiled: February 8, 2013Publication date: January 1, 2015Applicant: HONEYWELL INTERNATIONAL, INC.Inventors: Haiyou Wang, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu, Gustavo Cerri, Jeffrey Ball, Philip L. Da Prato, Xuehui Sun, Mario Joseph Nappa
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Patent number: 8921622Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.Type: GrantFiled: March 31, 2011Date of Patent: December 30, 2014Assignee: Solvay SAInventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
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Patent number: 8912368Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: GrantFiled: January 16, 2013Date of Patent: December 16, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 8912369Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.Type: GrantFiled: June 27, 2013Date of Patent: December 16, 2014Assignee: Central Glass Company, LimitedInventors: Hideaki Imura, Naoto Takada
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Publication number: 20140364658Abstract: The present invention relates to a method for preparing fluorinated olefin compounds, in particular (chloro)fluoropropenes and (chloro)fluorobutenes, and specifically, the fluorinated compound 2,3,3,3-tetrafluoro-1-propene, including at least one step of fluorination, in the gaseous phase, with HF and at least one compound selected from the halopropenes having formula the CX3CHClCH2X and the halopropenes having the formulas CX3CC1?CH2, CClX2CCl?CH2 and CX2?CClCH2X, where X is, independently, a fluorine or chlorine atom, in the presence of oxygen and a fluorination catalyst suspended in a fluidized-bed reactor.Type: ApplicationFiled: November 29, 2012Publication date: December 11, 2014Inventor: Jean-Luc Dubois
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Publication number: 20140350310Abstract: This disclosure relates to processes of making 1,3,3,3-tetrafluoropropene. The processes involve dehydrofluorinating 1,1,1,3,3-pentafluoropropane in vapor phase in the presence of a catalyst comprising a metal compound supported on alumina to produce a product mixture comprising 1,3,3,3-tetrafluoropropene, wherein said metal compound is selected from the group consisting of salts of sodium, potassium, zinc, magnesium, calcium, cobalt, copper, and chromium, and mixtures thereof.Type: ApplicationFiled: May 13, 2014Publication date: November 27, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: XUEHUI SUN, MARIO JOSEPH NAPPA
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Publication number: 20140343331Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, co-feed species HFC-245cb is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.Type: ApplicationFiled: March 13, 2014Publication date: November 20, 2014Applicant: HONEWELL INTERNATIONAL, INC.Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
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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: 8884083Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br.Type: GrantFiled: February 10, 2012Date of Patent: November 11, 2014Assignee: E. I. du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa
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Patent number: 8884082Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.Type: GrantFiled: February 16, 2012Date of Patent: November 11, 2014Assignee: E. I. du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa
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Patent number: 8877988Abstract: In accordance with the present invention, processes for producing bromofluoropropenes in commercial quantities by reacting 3,3,3-trifluoropropyne with hydrogen bromide at elevated temperatures are provided.Type: GrantFiled: December 6, 2013Date of Patent: November 4, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh
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Patent number: 8865952Abstract: The present invention provides a process for producing fluorine-containing alkene represented by Formula (2): Rf1C(Rf2)=CH2 wherein Rf1 and Rf2 are the same or different, and are F, H, F(CF2)n- wherein n is an integer of 1 to 5, or H(CF2)m- wherein m is an integer of 1 to 5, with the proviso that Rf1 and Rf2 are not simultaneously H, by heating fluorine-containing alkane represented by Formula (1): Rf1CF(Rf2))CH3 wherein Rf1 and Rf2 are as defined above, in a gas phase to perform a dehydrofluorination reaction, the dehydrofluorination reaction being carried out in the presence of 5 mol or more of anhydrous hydrogen fluoride per mol of the fluorine-containing alkane. The process of the present invention can significantly enhance the selectivity of fluorine-containing alkene without reducing conversion in the production of fluorine-containing alkene from fluorine-containing alkane, such as fluorine-containing propane.Type: GrantFiled: February 8, 2011Date of Patent: October 21, 2014Assignee: Daikin Industries, Ltd.Inventors: Yuzo Komatsu, Daisuke Karube
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Patent number: 8859829Abstract: The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).Type: GrantFiled: March 11, 2014Date of Patent: October 14, 2014Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
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Publication number: 20140303409Abstract: The present invention relates, in part, to the discovery that the presence of HF in a HCFC-244bb feedstream in a reaction for the preparation of HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing HF, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.Type: ApplicationFiled: September 29, 2012Publication date: October 9, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20140303411Abstract: A catalytic process for the synthesis of trifluoroethylene from chlorotrifluoroethylene which comprises contacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst consisting of palladium or platinum supported on extruded activated carbon.Type: ApplicationFiled: June 20, 2014Publication date: October 9, 2014Inventors: Stefano MILLEFANTI, Vito TORTELLI, Giuseppe MARCHIONNI
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Publication number: 20140296585Abstract: The present invention relates to a method for separating a composition containing 2,3,3,3-tetrafluoropropene and hydrofluoric acid, and for recovering the thus-separated 2,3,3,3-tetrafluoropropene and hydrofluoric acid. The invention also relates to a method for manufacturing and purifying 2,3,3,3-tetrafluoropropene using a hydrofluorination reaction of the saturated or unsaturated compound having three carbon atoms and including at least one chlorine atom in the presence of a fluorination catalyst.Type: ApplicationFiled: June 14, 2012Publication date: October 2, 2014Inventors: Dominique Deur-Bert, Bertrand Collier
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Patent number: 8846990Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.Type: GrantFiled: October 10, 2012Date of Patent: September 30, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20140275647Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.Type: ApplicationFiled: March 12, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL, INC.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
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Publication number: 20140275645Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.Type: ApplicationFiled: March 14, 2013Publication date: September 18, 2014Inventors: STEPHEN A. COTTRELL, JOHN J. SENETAR, HSUEH S. TUNG, DANIEL C. MERKEL, YUON CHIU, HALUK KOPKALLI
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Publication number: 20140275648Abstract: The invention relates to a process to produce 244bb from 1233xf in multiple reaction zones whereby the 1233xf starting material is at least 95% converted to 244bb and by-product such as 245cb forms in amounts less than about 2%.Type: ApplicationFiled: March 12, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL, INC.Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
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Publication number: 20140275646Abstract: The present process relates to a method for minimizing the formation of 1,1,1,2,2-pentafluoropropane in a liquid phase reaction of 2-chloro-3,3,3-trifluoropropene and HF in the presence of a hydrofluorination catalyst comprising: (a) reacting HF with sufficient amount of 2-chloro-3,3,3-trifluoropropene in the presence of a hydrofluorination catalyst under conditions effective to form 2-chloro-1,1,1,2-tetrafluoropropane, the hydrofluorination catalyst being present in sufficient amounts to catalyze said reaction and the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of greater than 80% and a 1,1,1,2,2-pentafluoropropane selectivity lower than 20%; and (b) maintaining the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of about 80% or more and a 1,1,1,2,2-pentafluoropropane selectivity of about 20% or less by adding said hydrofluorination catalyst to the reactor in small increments.Type: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou WANG, Daniel C. MERKEL, Hsueh Sung TUNG, Haluk KOPKALLI
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Patent number: 8835699Abstract: The invention relates to a process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2), performed using the steps of dehydrohalogenating 1,1,1,2,2-pentafluoropropane (CH3CF2CF3, HFC-245ca) 1,1,1,2-tetrafluoro-2-chloropropane, 1,1,1,2,3-pentafluoropropane (CH2FCHFCF3, HFC-245eb) and/or 1,1,1,2-tetrafluoro-3-chloropropane in the presence of a base, and converting a trifluorodichloropropane or a difluorotrichloropropane or a fluorotetrachloropropane to CH3CF2CF3, 1,1,1,2-tetrafluoro-2-chloropropane, CH2FCHFCF3, and/or 1,1,1,2-tetrafluoro-3-chloropropane.Type: GrantFiled: April 1, 2013Date of Patent: September 16, 2014Assignee: Mexichem Amanco Holding S.A. de C.VInventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles McCarthy
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Patent number: 8835698Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.Type: GrantFiled: May 7, 2013Date of Patent: September 16, 2014Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel