- Preparation method of hexafluorobutadiene
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The invention relates to a preparation method of hexafluorobutadiene, and belongs to the technical field of fluorine-containing gas preparation. The preparation method comprises the following steps: preparing a polar base solution, activated zinc and 1,2-dichloro2iodo-1,1,2-trifluoroethane, further preparing 1,2,3,4-tetrachlorohexafluorobutane, and finally preparing hexafluorobutadiene. Accordingto the method, activated zinc is used in the preparation process and is matched with a polar base solution serving as a solvent, so that the reaction rate is increased, the yield and selectivity of 1,2,3,4-tetrachlorohexafluorobutane are guaranteed; therefore, the problem that the reaction rate is influenced by using zinc particles which are not activated and have larger particles and adopting a solvent with poorer polarity in the prior art is solved; in addition, a non-polar solvent and activated zinc are added in the preparation of hexafluorobutadiene, so that byproducts generated in the preparation process of hexafluorobutadiene are easier to separate while the yield and selectivity of hexafluorobutadiene are ensured.
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Paragraph 0039; 0048; 0049; 0052; 0060; 0061; 0064; 0072
(2021/01/29)
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- Synthesis method of halogenated butene
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The invention discloses a synthesis method of halogenated butene. The method comprises: (1) carrying out a fluorination reaction on hexachlorobutadiene and a fluorination reagent, and purifying the obtained reaction product to obtain fluorochlorobutane; and (2) carrying out a dehalogenation reaction on the fluorochlorobutane and a dehalogenation reagent in a first solvent, and purifying the obtained reaction product to obtain the halogenated butene. The method has the advantages of simple process, less three wastes, high yield, low cost and the like.
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Paragraph 0095-0098
(2020/05/30)
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- METHOD AND APPARATUS FOR PRODUCING FLUORINE-CONTAINING ORGANIC COMPOUND
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Provided is a method for producing a fluorine-containing organic compound. The method can immediately detect the occurrence of a side reaction in direct fluorination reaction using fluorine gas and can give a highly pure fluorine-containing organic compound at a high yield. A raw material liquid (1) containing a raw material organic compound having a hydrogen atom and two or more carbon atoms is reacted with fluorine gas in a reaction container (11) to replace the hydrogen atom of the raw material organic compound with a fluorine atom to give a fluorine-containing organic compound. In the reaction, tetrafluoromethane contained in a gas phase (2) in the reaction container (11) is continuously measured, and the amount of the fluorine gas supplied to the reaction container (11) is controlled depending on the measured value of the tetrafluoromethane.
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Paragraph 0057-0067
(2020/12/01)
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- Method for preparing 1,2,3,4-tetrachlorohexafluorobutane
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The invention discloses a method for preparing 1,2,3,4-tetrachlorohexafluorobutane. 1,2-dichloro-2-iodo-1,1,2-trifluoroethane and metallic zinc which are used as raw materials undergo a ball milling process under the catalysis of ethyl acetate to obtain the 1,2,3,4-tetrachlorohexafluorobutane. The preparation method provided by the invention has the advantages of greenness, high efficiency and fewthree wastes, and is mainly used for preparing the 1,2,3,4-tetrachlorohexafluorobutane.
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Paragraph 0020-0029
(2019/05/02)
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- Method for preparing hexafluorobutadiene from iodine and chlorine
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The invention relates to a method for preparing hexafluorobutadiene from iodine and chlorine. The method comprises the following steps: preparing a metal coordinated ionic liquid solvent, and reacting iodine with chlorine to prepare iodine monochloride; reacting iodine monochloride with chlorotrifluoroethylene in the presence of the metal coordinated ionic liquid solvent to prepare 1,2-dichloro-2-iodo-1,1,2-trifluoroethane; carrying out a reaction on the 1,2-dichloro-2-iodo-1,1,2-trifluoroethane in the presence of the metal coordinated ionic liquid solvent under the catalysis of zinc powder to obtain 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane; and reacting the 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane with zinc powder in the presence of the metal coordinated ionic liquid solvent to generate hexafluorobutadiene.
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Paragraph 0038-0039; 0049-0050; 0060-0061; 0074
(2017/08/27)
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- PROCESSES FOR THE SYNTHESIS OF 1,2,3,4-TETRACHLORO-HEXAFLUORO-BUTANE
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The present invention relates to processes for the manufacture of 1,2,3,4-tetrachloro-hexafluoro-butane in a nnicroreactor.
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Paragraph 0069-0073
(2016/12/22)
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- PRODUCTION PROCESS AND PURIFICATION PROCESS FOR 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE
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It is an object of the present invention to provide a process for producing 1,2,3,4-tetrachlorohexafluorobutane industrially inexpensively and efficiently by utilizing expensive fluorine gas efficiently and to provide a process which is capable of stably producing 1,2,3,4-tetrachlorohexafluorobutane and in which, by carrying out fluorination reaction at a low temperature, side reactions such as formation of a low-boiling substance due to cleavage of C—C bonds and formation of an excess fluoride are difficult to occur. The process for producing 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that it includes feeding fluorine gas to 1,2,3,4-tetrachlorobutane using plural reactors in the presence of a solvent and in the absence of a catalyst to allow the 1,2,3,4-tetrachlorobutane and the fluorine gas to react with each other, wherein a part or all of unreacted fluorine gas discharged from one reactor is introduced into a reactor different from said one reactor.
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Page/Page column 6-7
(2011/04/18)
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- PROCESS FOR PRODUCING 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE
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The present invention provides a process for producing 1,2,3,4-tetrachlorohexafluorobutane having a high purity at a low cost industrially and efficiently. The process for producing 1,2,3,4-tetrachlorohexafluorobutane according to the present invention comprises a step of allowing 1,2,3,4-tetrachlorobutane to react with a fluorine gas to prepare a reaction product containing 1,2,3,4-tetrachlorohexafluorobutane and hydrogen-containing compounds as an impurity, and a step of introducing the reaction product into single or plural distillation columns and distilling to separate the hydrogen-containing compounds from the reaction product and thereby preparing purified 1,2,3,4-tetrachlorohexafluorobutane wherein the at least one of distillation columns has a theoretical plate number of 15 or more.
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Page/Page column 3-4
(2011/05/16)
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- PROCESS FOR PRODUCING FLUORINE-CONTAINING COMPOUND
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The process for producing a fluorine-containing compound such as 1,2,3,4-tetrachclorohexafluorobutane of the present invention is characterized in that a halogenated hydrocarbon compound such as 1,2,3,4-tetrachlorobutane is brought into contact with fluorine gas in a liquid phase or in a solid-liquid coexistence state in the absence of a solvent and a catalyst. According to the present invention, a fluorine-containing compound is readily produced from a halogenated hydrocarbon compound using neither a reaction solvent nor a reaction catalyst.
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Page/Page column 5
(2010/06/11)
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- PRODUCTION PROCESS FOR CHLORINE-CONTAINING FLUORINE-CONTAINING COMPOUND
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The production process of the present invention for a chlorine-containing fluorine-containing compound is characterized in that a reaction of adding chlorine atoms to a carbon-carbon unsaturated bond of a hydrogen-containing compound having a carbon-carbon unsaturated bond is carried out under the presence of a fluorine gas. The hydrogen-containing compound having a carbon-carbon unsaturated bond may be 3,4-dichlorobutene-1. Further, the present invention provides a process for producing efficiently and economically 1,2,3,4-tetrachlorohexafluorobutane from 3,4-dichlorobutene-1 described above. According to the present invention, chlorination and fluorination of the hydrogen-containing compound having a carbon-carbon unsaturated bond are carried out in a single step, and therefore a chlorine-containing fluorine-containing compound can be more economically produced at a higher yield than in a conventional process in which two reactions are individually carried out.
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Page/Page column 5
(2010/05/13)
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- PRODUCTION PROCESS FOR 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE AND REFINING PROCESS
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The production process for 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that 1,2,3,4-tetrachlorobutane is reacted with fluorine in the presence of a solvent containing hydrogen fluoride. The 1,2,3,4-tetrachlorobutane may be obtained by chlorination of 3,4-dichlorobutene-1. Further, the present invention provides as well a process of refining 1,2,3,4-tetrachlorohexafluorobutane obtained in the manner described above. According to the present invention, 1,2,3,4-tetrachlorohexafluorobutane which is useful, for example, as a synthetic raw material for hexafluoro-1,3-butadiene used as an etching gas for semiconductors can industrially efficiently be produced by using 1,2,3,4-tetrachlorobutane which is a by-product of chloroprene and which has so far been disposed.
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Page/Page column 5
(2010/06/14)
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- PROCESS FOR THE SYNTHESIS OF PERFLUOROBUTADIENE
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Process for preparing perfluoro-1,3-butadiene, comprising the following steps : A) preparation of fluoro-halo-butanes of formula : CF2 YI-CFYIICFYIICF2 YI (V) in which YI and YII which may be identical or different, may be H, C1 or Br, with the condition that YI and YII are not simultaneously hydrogen; starting with a chloroolefin having the formula : CY'Y = CY'C1 (II) in which Y, Y', Y', which may be identical or different, are H, C1 or Br, with the condition that Y, Y', Y' are not simultaneously hydrogen; and performing the following steps : - a fluorodimerization, and - a fluorination with elemental fluorine, the order of the two steps also possibly being inverted, - a dehalogenation or dehydrohalogenation step being performed between the two steps, B) dehalogenation or dehydrohalogenation of the fluoro-halo compounds of formula (V) to give the compound perfluoro-1,3-butadiene.
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Page/Page column 12-13
(2009/09/04)
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- PROCESS FOR PRODUCING HEXAFLUORO-1,3-BUTADIENE
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Disclosed is a process for producing hexafluoro-1,3-butadiene, which is used for an etching gas capable of being used in fine processing for semiconductors, safely in industrialization and at low cost economically. Specifically disclosed is a process for producing hexafluoro-1,3-butadiene comprises (1) a step comprising allowing a compound having four carbon atoms each which bonds to an atom selected from the group consisting of a bromine atom, an iodine atom and a chlorine atom, to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing a product (A), and (2) a step comprising eliminating halogens excluding a fluorine atom with a metal from the product (A) prepared in the step (1) in the presence of a solvent, thereby preparing a mixture containing hexafluoro-1,3-butadiene.
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Page/Page column 5-6
(2009/09/07)
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- PROCESS FOR PRODUCING 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE
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Disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane safely in a high yield in the industrial viewpoint and at low cost in the economical viewpoint. Specifically disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane which process comprises: (1) a step of chlorinating 1,3-butadiene, thereby preparing a mixture containing 1,2,3,4-tetrachlorobutane, and (2) a step of allowing the 1,2,3,4-tetrachlorobutane prepared in the step (1) to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing 1,2,3,4-tetrachlorohexafluorobutane.
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Page/Page column 4
(2009/09/07)
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- Coupling reactions of chlorofluoro and perfluoroalkyl iodides
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Coupling reactions of chlorofluoro- and perfluoroalkyl iodides R f-I with Rf = ClCF2CFCl-(CF2) 3CF2-, ClCF2CFClO(CF2) 3CF2-, ClCF2CFCl-, (CF3) 2CF- , (CF3)2CFCF2CF2- in the presence of a zinc/solvent system give dimers in good yields. Both homodimerizations (one iodide) and heterodimerizations (two different iodides) have been studied. The effect of temperature and solvent is shown. The zinc mediated dechlorination of vicinal chlorine atoms in the dimers afforded terminal alkenes and dienes.
- Wlassics, Ivan,Tortelli, Vito
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scheme or table
p. 1719 - 1728
(2009/06/05)
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- Process for preparing fluorohalogenethers
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A process for preparing (per)fluorohalogenethers having general formula (I): (R)nC(F)mOCAF—CA′F2??(I) wherein: A and A′, equal to or different the one from the other, are Cl or Br or one is selected from A and A′ and hydrogen and the other is halogen selected from Cl, Br; R═F, or a fluorinated, preferably perfluorinated, substituent, selected from the following groups: linear or branched C1-C20 alkyl more preferably C1-C10; C3-C7 cycloalkyl; aromatic, C6-C10 arylalkyl, alkylaryl; C5-C10 heterocyclic or alkylheterocyclic; when R is fluorinated or perfluorinated alkyl, cycloalkyl, arylalkyl, alkylaryl, it can optionally contain in the chain one or more oxygen atoms; when R is fluorinated it can optionally contain one or more H atoms and/or one or more halogen atoms different from F: n is an integer and is 1 or 2; m=3-n; by reaction of carbonyl compounds having formula (II): (R)pC(F)q(O)??(II) wherein: p is an integer and is 1 or 2; q is an integer and is zero or 1, R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF═CA′F??(III) wherein A and A′ are as above, at temperatures in the range from ?120° C. to ?20° C.
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- Process for preparing (per) fluorohalogenethers
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A process for preparing (per)fluorohalogenethers containing the —SO2F group, having general formula (I): FSO2—R—CF2OCAF—CA′F2??(I) wherein: A and A′, equal to or different from each other, are Cl or Br; R has the following meanings: a (per)fluorinated, preferably perfluorinated, substituent, optionally containing one or more oxygen atoms; by reaction of carbonyl compounds having formula (II): FSO2—R—COF??(II) wherein R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF═CA′F??(III) wherein A and A′ are as above, operating at temperatures from ?120° C. to ?20° C., optionally in the presence of a solvent inert under the reaction conditions.
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- Process for preparing (per)fluorohalogenethers
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A process for preparing (per)fluorohalogenethers containing the -SO2F group, having general formula (I):FSO2-R-CF2OCAF-CA' F2 wherein:A and A', equal to or different from each other, are Cl or Br;R has the following meanings: a (per)fluorinated, preferably perfluorinated, substituent, optionally containing one or more oxygen atoms; by reaction of carbonyl compounds having formula (II):FSO2-R-COF wherein R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III):CAF=CA'F wherein A and A'are as above, operating at temperatures from -120°C to -20°C, optionally in the presence of a solvent inert under the reaction conditions.
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Page column 6-7
(2008/06/13)
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- Reductive dehalogenation of polyhalofluorocarbons with tributyltin hydride
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The reduction of polyhalofluorocarbons, including ClCF2CFClCF2Cl, (ClCF2CFCl)2, ICH2(CF2)3CH2I and vicinal dichloroperfluorocycloalkanes, with tributyltin hydride gave the corresponding hydrofluorocarbons in good to excellent yield.The results are compared with similar reductions with other reducing agents, and to tin hydride reductions of non-fluorinated analogs. - Keywords: Reductive dehalogenation; Polyfluorocarbons; Tributyltin hydride; NMR spectroscopy; Hydrofluorocarbons
- Puy, Michael Van Der,Belter, Randolph K.,Borowski, Ralph J.,Ellis, Lois A. S.,Persichini, Phillip J.,et al.
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- Chlorotrifluoroethylene-derived fluids. I. Model compound synthesis
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A series of chlorofluoroalkanes having chlorines on adjacent carbon atoms has been prepared, i.e. n-C5F11CFClCCl3, n-C6F13CFClCCl3, n-C5F11CFClCFCl2, n-C6F13CFClCFCl2, n-C5F11CFClCF2Cl, n-C2F5CFClCFClC3F7 and n-CF3CFClCFClC4F9, by a combination of halogen exchange, dehalogenation and chlorine addition reactions.An attempt to synthesize n-C6F13CFClCF2CFCl2 by the coupling of n-C6F13CFClI with an excess of ICF2CFCl2 under UV radiation in the presence of Hg gave only n-C6F13CFClCFClC6F13 together with CFCl2CF2CF2CFCl2.Under parallel conditions from n-C6F13CFClI and CF2ClCFClI, n-C6F13CFClCFClCF2Cl was obtained in 48percent yield.
- Paciorek, K. J. L.,Kratzer, R. H.,Nakahara, J. H.,Lin, W.-H.
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p. 271 - 282
(2007/10/02)
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- SOLVENT EFFECTS IN BETWEEN PERFLUOROALKYLIODIDES AND CADMIUM
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The interaction between perfluoroorgano iodides (RfI where Rf = F(CF3)2C(CF2CF2)3, n-C6F13, n-C8F17, F(CF3)2COCF2CF2, F(CF3)2CO(CF2CF2)4 and C2H5OC(O)(CF2CF2)2OCF2CF2) with cadmium in an acetonitrile solvent media produces primarily the coupled products (RfRf, 72-90percent yield) in addition to minor quantities of the reduction products (RfH).On the other hand ICF2CF2I and ClCF2CFClI, by a 1,2-dehalogenation reaction, from the olefins CF2=CF2 and CF2=CFCl, respectively, as the principal products.The interaction of RfI compounds with cadmium in other solvent media, e.g. diethyl ether, tetrahydrofuran (YHF)), N,N-dimethylformamide (DMF), and bis(2-methoxyethyl)ether(diglyme) were examined and found to produce a different ratio of RfRf and RfH products.
- Chen, Grace J.,Tamborski, Christ
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p. 123 - 140
(2007/10/02)
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- Reaction of 1,2-Dichloroiodotrifluoroethane With Zinc
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The zinc coupling reaction of 1,2-dichloroiodotrifluoroethane (I) in acetic anhydride-methylene chloride has been reinvestigated in more detail than its original disclosure.The expected coupling product C4F6Cl4 was shown to be an isomeric mixture of three components, CF2ClCFClCFClCF2Cl (II, 80percent), CFCl2CF2CF2CFCl2 (IIa, 15percent) and CF2ClCFClCF2CFCl2 (IIb, 5percent).In addition, other products e.g.CF2-CFCl, C6F9Cl5 and C8F12Cl6 were formed in minor quantities.A probable mode of formation of various byproducts via initial formation of CF2-CFCl and subsequent telomerization is presented.
- Eapen, K. C.,Tamborski, C.
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p. 421 - 424
(2007/10/02)
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