Abstract: A process for the preparation of a selectively fluorinated organic compound, which process includes reaction of a precursor of said organic compound, the precursor containing at least one Group VI element selected from sulfur, selenium and tellurium, with a fluorinating agent and another halogenating agent and characterized in that the fluorinating agent is elemental fluorine.
Type:
Grant
Filed:
April 25, 1996
Date of Patent:
August 4, 1998
Assignee:
British Nuclear Fuels plc
Inventors:
Richard Dickinson Chambers, Graham Sandford
Abstract: The invention provides a process for production of 1,1,1,2,3,3,3-heptafluoropropane, HFC-227ea. In particular, the invention provides an inexpensive process for producing HFC-227ea in good yield by reacting 1,1,1,3,3,3-hexafluoropropane, HFC-236fa, with elemental fluorine in an inert gas.
Abstract: A process is disclosed for hydrofluorinating an olefinic hydrocarbon of the formulaX --CX'.dbd.CX'--R'where X, X' and X" are the same or different and are hydrogen or halo and R' is hydrogen or C.sub.1 -C.sub.6 alkyl, with hydrogen fluoride. The process is carried out by admixing the olefinic hydrocarbon with hydrogen fluoride in an imidofluoride hydrogen fluoride solvent having the formulaR--(CF.dbd.NH.sub.2).sup.+ F.sup.- .multidot..eta.HFwhere R is C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted with halo or C.sub.6 to C.sub.10 aryl either unsubstituted or substituted with alkyl and .eta. is 0 or an integer that is at least 1.
Abstract: The invention relates to a process for the work-up of a liquid complex hydrofluoride of a tertiary amine of the formula (I) ?R.sup.1 R.sup.2 R.sup.3 N.multidot.n HF!, where the radicals R.sup.1, R.sup.2 and R.sup.3 are C.sub.1 -C.sub.8 -alkyl groups which together have at least 7 carbon atoms and n is an integer or fractional number where 1.5<n<3, which, for the purpose of molecular addition of HF to a halogenated alkene, is reacted with the latter. In the reaction of the halogenated alkene with the complex amine hydrofluoride of the formula (I), the molar ratio HF:R.sup.1 R.sup.2 R.sup.3 N is allowed to fall until amine separates out as a further liquid phase, and the amine is separated off.
Abstract: The invention relates to a process for the preparation of 1,1-difluoroethane by reaction of vinyl chloride with hydrogen fluoride, in the presence of perchloroethylene or 1,1,1,3,3-pentafluorobutane.
Type:
Grant
Filed:
April 11, 1996
Date of Patent:
February 3, 1998
Assignee:
Solvay (Societe Anonyme)
Inventors:
Frans Grunchard, Francine Janssens, Vincent Wilmet
Abstract: A process is disclosed for producing 1,1-difluoroethane (HFC-152a) in a liquid phase by contacting chloroethene and hydrogen fluoride in the presence of a tin tetrahalide catalyst. The ability to reduce tar formation and increase volumetric productivity is also disclosed.
Abstract: Fluorination processes using hydrogen fluoride-containing fluorinating agents that are safely and easily handled, transported, and stored and that also exhibit good reactivity are provided. More particularly, the invention provides processes for producing fluorinated products using fluorinating agents comprising hydrogen fluoride and a carrier that may be an acid salt or a water-soluble polymer.
Type:
Grant
Filed:
March 7, 1996
Date of Patent:
January 6, 1998
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, Jeffrey Warren Mckown, Hang Thanh Pham, Andrew Joseph Poss, Rajiv Ratna Singh
Abstract: A continuous non-catalytic process for the manufacture of 1,1-dichloro-1-fluoroethane/1-chloro-1,1-difluoroethane mixtures from 1,1-dichloro-1-fluoroethane is provided. Hydrogen fluoride and 1,1,1-trichloroethane are continuously feed a molar ratio of from about 3.0 to about 5.2 to form a liquid phase hydrofluorination reaction mixture. Vapor phase reaction product is continuously withdrawn from the reaction zone, and hydrogen fluoride is continuously selectively refluxed back to the reaction mixture. 1,1,1-Trichloroethane utilization approaches 100% , with selectivity for 1,1-dichloro-1-fluoroethane between 15% and 85%, based upon the amount of 1,1-dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane contained in the gaseous reaction product.
Abstract: 1,1,1-Trifluoroethane (HFC-143a) is produced in the liquid phase by reaction between vinylidene fluoride and hydrogen fluoride, in the absence of catalyst.
Abstract: A process for preparation of a gem-difluoroalkane is provided which comprises(A) a step to add a fluorinated alkane having a boiling point of -30.degree. to 30.degree. to a crude alkyne having 3 or 4 carbon atoms containing a polymerizable olefin as an impurity, and distill the mixture to remove the polymerizable olefin,(B) a step to react hydrogen fluoride with the fluorinated alkane and the alkyne having 3 or 4 carbon atoms obtained in the above step to synthesize the gem-difluoroalkane, and(C) a step to distill the reaction solution of the above (B) to obtain the gem-difluoroalkane.According to this process, gem-difluoroalkanes can be prepared more economically compared with usual processes.
Abstract: A process is disclosed for purifying a hexafluoroethane product containing CClF.sub.3 and/or CHF.sub.3 impurities which comprises the step of contacting the product with a sorbent for said impurities selected from activated carbons and inorganic (i.e. zeolite) molecular sieves. Also disclosed is an improvement to a process for producing CF.sub.3 CF.sub.3 wherein CClF.sub.3 and/or CHF.sub.3 impurities are removed from the product utilizing said sorbents.
Type:
Grant
Filed:
December 28, 1994
Date of Patent:
June 4, 1996
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
David R. Corbin, Richard E. Fernandez, Barry A. Mahler
Abstract: A process is disclosed for the preparation of pentafluoroethane from chlorotetrafluoroethane (the yield of pentafluoroethane is at least 50 mole percent based upon the amount of chlorofluoroethane reacted with HF) with particularly low levels of chlorofluoroethanes. The process involves providing sufficient pretreatment (where necessary) of a Cr.sub.2 O.sub.3 catalyst with at least one agent selected from the group consisting of CO, H.sub.2, H.sub.2 O and mixtures thereof in the gaseous state such that the total chlorofluoroethane content of said product stream is less than 1 mole percent. Certain high surface area catalysts may be used without such pretreatment.
Type:
Grant
Filed:
February 17, 1995
Date of Patent:
December 12, 1995
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
Mario J. Nappa, V. N. Mallikarjuna Rao, William R. Williams
Abstract: This specification discloses a process for preparing 1,1-dichlorofluoroethane (HCFC-141b) and 1-chloro-1,1-difluoroethane (HCFC-142b) from 1,1,1-trichloroethane and hydrogen fluoride which is capable of increasing reaction conversion and selectivity of the reaction products, HCFC-141b and HCFC-142b. According to the process of the invention, HCFC-142b, one of the reaction products, which has high solubility in both hydrogen fluoride and 1,1,1-trichloroethane, in the liquid phase reaction system is maintained at above 20 mole % relative to 1,1,1-trichloroethane. Therefore, the solubility of HF in the organic phase is remarkably enhanced, and the reaction of HF with 1,1,1-trichloroethane or vinylidene chloride is well promoted. Furthermore, the resident time of the reactant in the reaction vessel is shortened and thus the formation of tars is considerably prevented.
Type:
Grant
Filed:
January 6, 1994
Date of Patent:
July 18, 1995
Assignee:
Korea Institute of Science and Technology
Inventors:
Hong G. Kim, Hoon S. Kim, Young S. Kwon, Kun Y. Park
Abstract: Hydrogen fluoride and 1,1,1-trifluoro-2-chloroethane forms an azeotropic mixture of which molar ratio of HF/1,1,1-trifluoro-2-chloroethane varies, for example, from about 60/40 at a pressure of 1.5 Kg/cm.sup.2 G and a temperature of 20.degree. C. to about 45/55 at a pressure of 15 Kg/cm.sup.2 G and a temperature of 87.degree.C.
Abstract: In a process for preparing 1,1,1-trifluorochloroethane by reacting, in a gas phase, trichloroethylene and hydrogen fluoride, when the reactant gases are diluted with a gas which is inactive to the reaction, it is very easy to control a reaction temperature, and when a generated gas from the reaction of 1,1,1-trifluorochloroethane and hydrogen fluoride is used as a diluent gas, generation of 1,1-difluoroethylene is suppressed to a very low level while not influencing the reaction between trichloroethylene and hydrogen fluoride.
Abstract: The invention relates to a thermal process the production of 1,1-dichloro-1-fluoroethane by hydrofluorination of vinylidene chloride carried out in the absence of any catalyst.
Abstract: A process for producing 1,1,1,2-tetrafluoroethane from trichloroethylene and HF, which comprises introducing products of a reaction of trichloroethylene with HF, and products of a reaction of 1,1,1-trifluoro-2-chloroethane with HF into a first distillation column either separately or as a mixture thereof, recovering HCl as a distillate from the top of the first distillation column, and introducing the remainder into a second distillation column.
Abstract: A process for production of 1,1,1-trifluoro-2,2-dichloroethane comprising chlorination of 1,1,1-trifluoro-2-chloroethane with chlorine gas in the presence or absence of a metal salt as a catalyst.
Abstract: Halogenated aromatics are prepared by heating halogenoformic acid esters to 80.degree. to 280.degree. C. in the presence of hydrogen fluoride or a catalytic amount of one or more Lewis acids from the group comprising aluminium halides, iron halides and antimony halides, and in the liquid phase.
Type:
Grant
Filed:
July 28, 1993
Date of Patent:
April 26, 1994
Assignee:
Bayer Aktiengesellschaft
Inventors:
Norbert Lui, Dietmar Bielefeldt, Albrecht Marhold
Abstract: A process for working up the hydrogen fluoride phase of reaction mixtures from fluorination reactions comprising contacting the hydrogen fluoride phase with oleum in order to obtain dried hydrogen fluoride, which can be recycled to the fluorination reaction.
Type:
Grant
Filed:
January 11, 1993
Date of Patent:
April 5, 1994
Assignee:
Solvay Fluor and Derivate GmbH
Inventors:
Johannes Eicher, Werner Rudolph, Bernhard Schulte
Abstract: A process for producing 1,1,1,2-tetrafluoroethane through a reaction of trichloroethylene with HF, which comprises the steps of:(a) allowing trichloroethylene to react with HF in a first reactor to form 1,1,1-trifluoro-2-chloroethane,(b) allowing 1,1,1-trifluoro-2-chloroethane to react with HF in a second reactor to form 1,1,1,2-tetrafluoroethane,(c) introducing the products of the above steps (a) and (b) into a first distillation column where the products are separated into a distillate containing 1,1,1,2-tetrafluoroethane and HCl as main components, a side-cut fraction containing 1,1,1-trifluoro-2-chloroethane and HF as main components and a bottom liquid containing HF as a main component and a small amount of trichloroethylene, and(d) introducing the distillate of the above step (c) into a second distillation column where HCl is recovered as a distillate and a 1,1,1,2-tetrafluoroethane fraction containing small amounts of 1,1,1-trifluoro-2-chloroethane and HF is discharged from the bottom of the second dis
Abstract: To replace the cleaning compositions based on 1,1,2-trichloro-1,2,2-trifluoroethane (F113), the invention proposes a composition comprising, on a weight basis, 60 to 90% of 1,1-dichloro-1-fluoroethane (F141b), 9 to 33% of 1,1,1,3,3-pentafluorobutane (F365 mfc) and 1 to 7% of methanol. These three compounds form a positive azeotrope (b.p.=29.1.degree. C. at normal pressure).The composition, optionally stabilized, can be employed for the cleaning and/or drying of solid surfaces, in particular for the defluxing of printed circuits and for the degreasing of mechanical components.
Abstract: A process for production of 1,1,1-trifluoro-2,2-dichloroethane comprising chlorinationo f 1,1,1-trifluoro-2-chloroethane with chlorine gas in the presence or absence of a metal salt as a catalyst.
Abstract: Novel partially fluorinated alkenes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkenyl or fluoroalkenyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.
Type:
Grant
Filed:
December 4, 1990
Date of Patent:
February 11, 1992
Assignee:
Allied-Signal Inc.
Inventors:
Chien C. Li, Kane D. Cook, Rajat S. Basu
Abstract: Novel partially fluorinated alkanes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.2 -, CH.sub.3 CF.sub.2 -, or CF.sub.3 have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.
Abstract: 1,1-Dichloro-1-fluoroethane and/or 1-chloro-1,1-difluoroethane are selectively produced by fluorination of 1,1,1-trichloroethane. Conditions in a first reaction zone selected to preferentially form 1,1-dichloro-1-fluoroethane. The reaction effluent is split between a 1,1-dichloro-1-fluoroethane recovery system, and a second reaction zone. The effluent from the latter is routed to 1-chloro-1,1,-difluoroethane recovery system. The second reaction zone conditions are selected for form 1-chloro-1,1-difluoroethane. The ratio of product formed by the overall process may be varied from up to 98% 1,1-dichloro-1-fluoroethane to greater than 98% 1-chloro-1,1-difluoroethane.
Abstract: 1,1-Dichloro-1-fluoroethane, 1-chloro-1,1-difluoroethane and hydrogen fluoride are separated from their liquid mixtures, such as liquid mixtures resulting from the hydrofluorination, of 1,1,1-trichloroethane or vinylidene chloride. 1,1-Dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane are first separated by distillation into their respective mixtures with hydrogen fluoride, which are thereafter subjected to parallel phase separations resulting in two hydrogen fluoride-enriched liquid phases, a 1-chloro-1,1-difluoroethane-enriched liquid phase and a 1,1-dichloro-1-fluoroethane-enriched liquid phase. 1-Chloro-1,1-difluoroethane and 1,1-dichloro-1-fluoroethane are purified from the respective halohydrocarbon-enriched liquid phases by distillation. The hydrogen fluoride-enriched stream generated from the phase separation of the hydrogen fluoride/1,1-dichloro-1-fluoroethane mixture is recycled to the hydrofluorination reaction mixture.
Abstract: The present invention provides a process for the purification of 1,1-dichloro-1-fluoroethane comprising the steps of: (a) reacting anhydrous hydrogen fluoride with 1,1,1-trichloroethane or vinylidene chloride containing dichloroacetylene to form 1,1-dichloro-1-fluoroethane; and (b) passing the 1,1-dichloro-1-fluoroethane through activated carbon to substantially remove unsaturated impurities. In particular, the present process reduces the amounts of dichloroacetylene and vinylidene chloride in the 1,1-dichloro-1-fluoroethane product so as to meet the current specifications set forth by the Panel for Advancement of Fluorocarbon Test.The purified 1,1-dichloro-1-fluoroethane product is useful as a blowing agent and a solvent.
Abstract: 1,1-Dichloro-1-fluroethane and 1,1,1,3,3-pentafluorobutane are separated from their liquid mixtures, such as liquid mixtures resulting from the hydrofluorination of 1,1,1-trichloroethane or vinylidene chloride. 1,1-Dichloro-1-fluoroethane and 1,1,1,3,3-pentafluorobutane are completely separated by distillation, by adding to the mixture thereof a liquid containing at least about 3 moles of hydrogen fluoride per mole of 1,1-dichloro-1-fluoroethane in the mixture subject to separation.
Abstract: This invention relates to a continuous gaseous-phase process for the preparation of trichlorotrifluoroethane, dichlorotetrafluoroethane and monochloropentafluoroethane, in predetermined proportions, from tetrachloroethylene, chlorine and hydrofluoric acid in the presence of a catalyst. The process is characterized by the combination of two chlorination-fluorination reactors in sequence, a parallel fluorination-dismutation reactor, and a separation unit for extracting the desired products and recycling recovered hydrofluoric acid and non-fluorinated or insufficiently fluorinated products. The process advantageously yields dichlorotetrafluoroethane containing less than 7% asymmetric isomer, and trichlorotrifluoroethane containing less than 2% asymmetric isomer.
Type:
Grant
Filed:
November 25, 1981
Date of Patent:
August 12, 1986
Assignee:
PCUK Products Chimiques Ugine Kuhlmann
Inventors:
Michel Abel, Francois Fine, Louis Foulletier, Yvan Verot
Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
Abstract: A process for the preparation of an optionally substituted trifluoromethyl-naphthalene which comprises contacting a compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, alkyl, aralkyl, aryl, aryloxy, arylthio, polyhalogenoalkoxy, polyhalogenoalkylthio, halogen, nitro, halogenocarbonyl, halogenosulphonyl, alkylsulphonyl or arylsulphonyl, it being possible for the aromatic nuclei contained in the substituents R.sup.1 to be in turn substituted by halogen, alkyl, polyhalogenoalkoxy or polyhalogenoalkylthio,R.sup.2 represents hydrogen, halogen or alkyl andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 denote hydrogen, orR.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 in each case together denote a fused-on aromatic ring, and wherein, in the case where R.sup.3 and R.sup.4 together form a fused-on aromatic ring,R.sup.5 and R.sup.6 independently of one another can also denote, in addition to hydrogen, halogen, nitro, halogenocarbonyl or halogenosulphonyl, and wherein, in the case where R.sup.4 and R.sup.
Abstract: Novel compounds of general formula (I) ##STR1## wherein X represents a F, Cl, Br, I or CN are of interest as heat stable ligands for catalytic systems. They can be prepared in good yields from 1,5-dimethyl-1,5-cyclooctadiene as well as from the corresponding bicyclic alcohol wherein X is OH.
Type:
Grant
Filed:
December 21, 1979
Date of Patent:
December 16, 1980
Assignee:
Shell Oil Company
Inventors:
Albertus J. Mulder, Pieter A. Verbrugge