WO2010095764A1 - Procede de preparation de compose alcyne contenant du fluor - Google Patents

Procede de preparation de compose alcyne contenant du fluor Download PDF

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Publication number
WO2010095764A1
WO2010095764A1 PCT/JP2010/053023 JP2010053023W WO2010095764A1 WO 2010095764 A1 WO2010095764 A1 WO 2010095764A1 JP 2010053023 W JP2010053023 W JP 2010053023W WO 2010095764 A1 WO2010095764 A1 WO 2010095764A1
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Prior art keywords
alkaline earth
fluorine
alkali metal
earth metal
group
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PCT/JP2010/053023
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English (en)
Inventor
Tsuneo Yamashita
Masatoshi Nose
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Daikin Industries, Ltd.
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Priority to JP2011535813A priority Critical patent/JP2012518599A/ja
Publication of WO2010095764A1 publication Critical patent/WO2010095764A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B01J23/04—Alkali metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/12—Fluorides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/618—Surface area more than 1000 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon

Definitions

  • the present invention relates to a process for preparing a fluorine -containing alkyne compound.
  • Muorine-containing alkyne compounds such as 3,3,3-trifluoropropyne are highly useful because the compounds are useful as materials or raw materials for refrigerants, etching agents, and aerosols, and can also be used as intermediates of various materials and monomer components of polymer compounds.
  • one known method for producing 3,3,3-trifruoropropyne uses 2,3-dibiOmo-l,l,l-trifluoropropene as a starting material and comprises performing the following production steps (see Non-Patent Literatures (NPLs) 1 to 3 listed below).
  • Another known method for producing 3,3,3-trifluoropropyne comprises preparing 3,3,3-trifruoropropyne from l,l,2-trichloro-3,3,3-trifluoropropene (see Non-Patent Literature 4).
  • this method entails a zinc waste disposal problem, because the method uses a zinc compound as a starting material.
  • Non-Patent Literature 5 a method comprising reacting l-iodo-3,3,3-trifluoropropene with potassium fluoride (KF) is also known (see Non-Patent Literature 5).
  • KF potassium fluoride
  • Non-Patent Literature (NPL) 6 listed below a method comprising reacting acetylenecarboxy ⁇ c acid (HC ⁇ CCOOH) with sulfur tetrafluoride (SF 4 ) is also reported (see Non-Patent Literature (NPL) 6 listed below).
  • NPL Non-Patent Literature 6 listed below.
  • this method is not industrially advantageous because acetylenecarboxylic acid used as a starting material is expensive and sulfur tetrafluoride is difficult to handle.
  • Patent Literature (PTL) l a method comprising reacting ( ⁇ )-l-halogeno-3,3,3-trifluoropiOpene as a starting material with a base in a liquid phase is also reported (see Patent Literature (PTL) l).
  • PTL Patent Literature
  • this method can be performed only when a ⁇ isomer is used as the starting material.
  • a large amount of alkaline waste is generated because a base is used for the reaction.
  • NPL l Journal of the American Chemical Society, 1951, 73, 1042-3.
  • NPL 2- Journal of the Chemical Society, 1951, 2495-504.
  • NPL 3 Journal of the Chemical Society, 1952, 3483-90.
  • NPL 4 Journal of Organic Chemistry, 1963, 28, 1139-40.
  • NPL 5 Journal of Fluorine Chemistry, 1978, 12(4), 321-4.
  • NPL 6 Journal of the American Chemical Society, 1959, 81,
  • a primary object of the invention is to provide a novel process for producing a fluorine-containing alkyne compound, such as
  • the present inventors conducted extensive research to achieve the above object, and found the following.
  • a specific fluorine-containing alkene compound is used as a starting material, and subjecting the starting material to a dehydrohalogenation reaction in a gas phase in the presence of at least one compound selected from the group consisting of alkali metal- or alkaline earth metal-containing halides; alkali metal- or alkaline earth metal-containing oxides; and alkali metal- or alkaline earth metal-containing hydroxides
  • the target fluorine -containing alkyne compound can be obtained with a high selectivity.
  • the compound can be produced with high efficiency, because this reaction can be conducted as a continuous reaction.
  • the present invention has been accomplished on the basis of this finding.
  • the present invention provides the following processes for producing a fluorine-containing alkyne compound.
  • Item 2 The process according to Item 1, wherein the catalyst is a fluoride of an alkali metal or an alkaline earth metal.
  • Item 3 The process according to Item 1 or 2, wherein the catalyst comprises a carrier and a catalyst component supported on the carrier, the catalyst component being at least one compound selected from the group consisting of alkali metal- or alkaline earth metal-containing halidesj alkali metal- or alkaline earth metal-containing oxides! and alkali metal- or alkaline earth metal-containing hydroxides.
  • Item 4 The process according to any one of Items 1 to 3, wherein Rf is a trifluoromethyl group.
  • Rf represents a fluorine-containing alkyl group, such as a perfluoroalkyl group having about 1 to about 10 carbon atoms, or a fluorinated alkyl group having about 1 to about 10 carbon atoms.
  • fluorine-containing alkyl group include trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoro-t-butyl group, and like groups.
  • One of X and Y is a halogen atom, and the other is a hydrogen atom.
  • the halogen atom include chlorine, fluorine, bromine, and iodine.
  • the fluorine-containing alkene compound can exist as Z(cis) or Ei ⁇ rans) isomers. Both the Z- and j ⁇ '-isomers can be used as the starting material in the present invention. This is an important distinction between the present invention and the method disclosed in the above Patent literature 1. According to the method of Patent literature 1, the reaction does not proceed when the j ⁇ '-isomer is used. Reaction process
  • This process can produce a fluorine-containing alkyne compound represented by formula"-
  • Rf is a fluorine-containing alkyl group, with a high selectivity.
  • alkali metal- or alkaline earth metal-containing halides examples include Na, K, Ii, Rb, and CsJ examples of alkaline earth metals include Ca, Mg, Sr, and BaJ and examples of halides include fluoride, chloride, iodide, and bromide.
  • halides of alkali metals or alkaline earth metals include fluorides such as NaF, KF, IiF, RbF, CsF, CaF 2 , MgF 2 , BaF 2 , and SrF 2 ; chlorides such as NaCl, KCl, IiCl, RbCl, CsCl, CaCl 2 , MgCl 2 , BaCl 2 , and SrCl 2 ; iodides such as NaI, KI, IiI, RbI, CsI, CaI 2 , MgI 2 , BaI 2 , and SrI 2 ; bromides such as NaBr, KBr, LiBr, RbBr, CsBr, CaBr 2 , MgBr 2 , BaBr 2 , and SrBr 2 .
  • fluorides such as NaF, KF, IiF, RbF, CsF, CaF 2 , MgF 2
  • Examples of oxides of alkali metals or alkaline earth metals include Na 2 O, K 2 O, Ii 2 O, Rb 2 O, Cs 2 O, CaO, MgO, BaO, and SrO.
  • Examples of hydroxides of alkali metals or alkaline earth metals include NaOH, KOH, IiOH, RbOH, CsOH, Ca(OH) 2 , Mg(OH) 2 , Ba(OH) 2 , and Sr(OH) 2 .
  • Such alkali metal- or alkaline earth metal-containing halides; alkali metal- or alkaline earth metal-containing oxides; and alkali metal- or alkaline earth metal-containing hydroxides can be used singly, or in a combination of two or more. Fluorides of alkali metals or alkaline earth metals are particularly preferable in the present invention.
  • the catalyst component that is at least one compound selected from the group consisting of alkali metal- or alkaline earth metal-containing halides; alkali metal- or alkaline earth metal-containing oxides; and alkali metal- or alkaline earth metal-containing hydroxides may be supported on a carrier.
  • Any carrier that is stable in the dehydrohalogenation reaction can be used.
  • the carrier can be appropriately selected from known carriers. For example, activated carbon, metallic aluminum, silica, alumina, zirconia, magnesia, titania, celite, zeolite, silicon carbide, diatomaceous earth, or the like can be preferably used as the carrier. Activated carbon is particularly preferable.
  • the carrier used to support the catalyst preferably has a large specific surface area of about 50 to about 1,500 m 2 /g, and more preferably about 300 to about 1,500 m 2 /g.
  • the amount of catalyst component supported on the carrier is about 1 to about 60 wt.%, when the total weight of the catalyst component and the carrier is defined as 100 wt.%.
  • the efficiency of contact between the starting material and the catalyst component can be enhanced, so that the target fluorine-containing alkyne compound can be obtained with a high selectivity.
  • the dehydrohalogenation reaction can be performed by bringing a fluorine-containing alkene compound as the starting material in a gas phase into contact with the catalyst.
  • the dehydrohalogenation reaction can be performed by supplying a fluorine-containing alkene compound as a starting material in a gas phase to a reactor containing the catalyst.
  • the fluorine-containing alkene compound may be supplied to the reactor as is, or after dilution with an inert gas, such as nitrogen, helium, or argon.
  • the type of reactor is not particularly limited.
  • adiabatic reactors containing a catalyst multitubular reactors cooled using a heat-transmitting maximin, etc. can be used. It is preferable to use a reactor made of a material that is resistant to the corrosive action of hydrogen fluoride, such as Hastelloy, Inconel, Monel, or like reactors.
  • the dehydrohalogenation reaction temperature in the reactor is preferably about 200°C to about 650°C, and more preferably about 300°C to about 550°C. If the temperature is higher than this range, the selectivity will be low, whereas if the temperature is lower, the conversion of the starting material will be low, neither of which is desirable.
  • the pressure during the reaction is not particularly limited, and the reaction can be carried out under normal pressure or increased pressure. More specifically, the dehydrohalogenation reaction of the present invention can be carried out under atmospheric pressure (0.1 MPa), or under an increased pressure of up to about 1.0 MPa.
  • the reaction time is not particularly limited.
  • the contact time which is determined by WfFo, may typically be adjusted to a range of about 0.1 to 300 g-sec/cc, and preferably about 10 to about 180 g-sec/cc.
  • W/Fo is the ratio of a catalyst weight W (g) to a total flow rate Fo (flow rate at O 0 C and 0.1 MPa ⁇ cc/sec) of the starting material gas that is introduced to a reaction system.
  • the catalyst weight is defined as the total weight of the catalyst component and the carrier.
  • RfC ⁇ CH wherein Rf is a fluorine-containing alkyl group can be obtained.
  • the target fluorine-containing alkyne compound can be obtained with a high selectivity. Further, because it is a gas phase reaction, the reaction can be easily performed as a continuous reaction, and the target fluorine-containing alkyne compound can be efficiently produced. Furthermore, because both the Z- and ⁇ -isomers can be used as the starting material, the starting material can be selected from a wide range. Accordiiigly, the process of the present invention is highly useful as an industrial-scale production method for a fluorine-containing alkyne compound.
  • CsF cesium fluoride
  • purity: 99% cesium fluoride
  • 30.0 g of activated carbon (Calgon, BPL4xlO, specific surface area: 1,150 m 2 /g) that had been dried at 250 0 C for 4 hours under a stream of nitrogen and then cooled to room temperature was added to this solution. The mixture was gently stirred until no more air bubbles were generated under reduced pressure. After aging at room temperature for 5 hours, the mixture was dried in a nitrogen stream at 15O 0 C for 12 hours.
  • a tubular Hastelloy reactor having an inner diameter of 15 mm and a length of 1 m was charged with 30 g of Catalyst A.
  • the reactor was maintained at atmospheric pressure (0.1 MPa) at 300 0 C, and nitrogen (N2) was supplied to the reactor at a rate of 100 cc/r ⁇ in (flow rate at 0 0 C and 0.1 MPa) for 2 hours.
  • N2 nitrogen
  • 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf, purity: 99.9 0 /0) was then supplied at a rate of 20 ce/min (flow rate at 0°C and 0.1 MPa), and the supply of nitrogen (N 2 ) was immediately stopped.
  • the reaction temperature was then adjusted to 350°C.
  • the contact time (WZF 0 ) was 90.0 g'sec/cc.
  • Example 3 The experiment was conducted under the same conditions as in Example 1, except that the reaction temperature was adjusted to 400°C.
  • the contact time (W/Fo) was 90.0 g-sec/cc.
  • Example 3 The experiment was conducted under the same conditions as in
  • Example 1 except that the reaction temperature was adjusted to 500°C.
  • the contact time (W/Fo) was 90.0 gsedce.
  • a tubular Hastelloy reactor having an inner diameter of 20 mm and a length of 1 m was charged with 30 g of Catalyst B.
  • the reactor was maintained at atmospheric pressure (0.1 MPa) at 300°C, and nitrogen (Ns) was supplied to the reactor at a rate of 100 cc/miii (flow rate at 0°C and 0.1 MPa) for 2 hours.
  • Ns nitrogen
  • the reaction temperature was then adjusted to 400°C.
  • the contact time (W/Fo) was 60.0 g-sec/cc.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé permettant de produire un composé alcyne contenant du fluor représenté par la formule, dans laquelle Rf représente un groupe alkyle contenant du fluor, le procédé consistant notamment à soumettre un composé alcène contenant du fluor représenté par la formule, RfCX=CHY, dans laquelle Rf représente un groupe alkyle contenant du fluor, et X et Y représentent l'un ou l'autre un atome d'halogène, l'autre représentant un atome d'hydrogène, à une réaction de déshydrohalogénation en phase gazeuse en présence d'au moins un composé choisi dans le groupe composé de halogénures contenant du métal alcalin ou du métal alcalino-terreux; des oxydes contenant du métal alcalin ou du métal alcalino-terreux; et des hydroxydes contenant du métal alcalin ou du métal alcalino-terreux. Ce procédé permet de produire d'une manière relativement simple un composé alcyne contenant du fluor, tel que 3,3,3-trifluoropropyne, à sélectivité élevée.
PCT/JP2010/053023 2009-02-23 2010-02-19 Procede de preparation de compose alcyne contenant du fluor WO2010095764A1 (fr)

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JP2011535813A JP2012518599A (ja) 2009-02-23 2010-02-19 含フッ素アルキン化合物の製造方法

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US15452509P 2009-02-23 2009-02-23
US61/154,525 2009-02-23

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130310614A1 (en) * 2012-05-15 2013-11-21 Honeywell International Inc. Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene
US8791309B2 (en) 2012-12-21 2014-07-29 Honeywell International Inc. Synthesis of 3,3,3-trifluoropropyne
US20140343330A1 (en) * 2013-05-20 2014-11-20 Honeywell International, Inc. Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene
EP2585423B1 (fr) 2010-06-28 2015-09-30 Honeywell International Inc. Procédé destiné à prolonger la durée de vie d'un catalyseur durant l'hydrofluoration
US9353030B2 (en) * 2014-07-25 2016-05-31 Honeywell International Inc. One-step process for hexafluoro-2-butene
GB2535512A (en) * 2015-02-19 2016-08-24 Mexichem Fluor Sa De Cv Process
EP3260439A1 (fr) * 2011-02-21 2017-12-27 The Chemours Company FC, LLC Un catalyseur supporté sur du carbone comprenant un sel de métal alcalin de formule my
WO2019030527A1 (fr) * 2017-08-09 2019-02-14 Mexichem Fluor S.A. De C.V. Compositions comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (hcfo-1233xf) et leurs utilisations
CN110845296A (zh) * 2019-12-12 2020-02-28 岳阳市宇恒化工有限公司 一种制备炔基化合物的方法
CN112194556A (zh) * 2019-07-08 2021-01-08 大金工业株式会社 氟化乙烯基化合物的制造方法
CN112794787A (zh) * 2021-04-08 2021-05-14 北京宇极科技发展有限公司 气相连续制备3,3,3-三氟-2-(三氟甲基)-1-丙烯的方法
CN113004117A (zh) * 2021-04-22 2021-06-22 泉州宇极新材料科技有限公司 气相脱卤化氢制备3,3,3-三氟丙炔的方法
CN114797957A (zh) * 2022-05-12 2022-07-29 辽宁浚成科技有限公司 一种碳酸亚乙烯酯液相合成的固体催化剂及制备方法和应用
CN116120149A (zh) * 2023-04-04 2023-05-16 北京宇极科技发展有限公司 饱和卤代烃脱卤化氢制备含氟炔的方法

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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2585423B1 (fr) 2010-06-28 2015-09-30 Honeywell International Inc. Procédé destiné à prolonger la durée de vie d'un catalyseur durant l'hydrofluoration
EP3260439A1 (fr) * 2011-02-21 2017-12-27 The Chemours Company FC, LLC Un catalyseur supporté sur du carbone comprenant un sel de métal alcalin de formule my
US9000239B2 (en) * 2012-05-15 2015-04-07 Honeywell International Inc. Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene
US20130310614A1 (en) * 2012-05-15 2013-11-21 Honeywell International Inc. Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene
US8791309B2 (en) 2012-12-21 2014-07-29 Honeywell International Inc. Synthesis of 3,3,3-trifluoropropyne
CN104936935A (zh) * 2012-12-21 2015-09-23 霍尼韦尔国际公司 3,3,3-三氟丙炔的合成
CN104936935B (zh) * 2012-12-21 2018-07-03 霍尼韦尔国际公司 3，3，3-三氟丙炔的合成
US20140343330A1 (en) * 2013-05-20 2014-11-20 Honeywell International, Inc. Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene
US9216932B2 (en) * 2013-05-20 2015-12-22 Honeywell International Inc. Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene
EP3172182A4 (fr) * 2014-07-25 2018-01-24 Honeywell International Inc. Procédé en une étape pour la production d'hexafluoro-2-butène
US9353030B2 (en) * 2014-07-25 2016-05-31 Honeywell International Inc. One-step process for hexafluoro-2-butene
GB2535512A (en) * 2015-02-19 2016-08-24 Mexichem Fluor Sa De Cv Process
WO2019030527A1 (fr) * 2017-08-09 2019-02-14 Mexichem Fluor S.A. De C.V. Compositions comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (hcfo-1233xf) et leurs utilisations
GB2567919A (en) * 2017-08-09 2019-05-01 Mexichem Fluor Sa De Cv Compositions and uses thereof
CN112194556A (zh) * 2019-07-08 2021-01-08 大金工业株式会社 氟化乙烯基化合物的制造方法
CN110845296A (zh) * 2019-12-12 2020-02-28 岳阳市宇恒化工有限公司 一种制备炔基化合物的方法
CN112794787A (zh) * 2021-04-08 2021-05-14 北京宇极科技发展有限公司 气相连续制备3,3,3-三氟-2-(三氟甲基)-1-丙烯的方法
CN112794787B (zh) * 2021-04-08 2021-07-09 泉州宇极新材料科技有限公司 气相连续制备3,3,3-三氟-2-(三氟甲基)-1-丙烯的方法
CN113004117A (zh) * 2021-04-22 2021-06-22 泉州宇极新材料科技有限公司 气相脱卤化氢制备3,3,3-三氟丙炔的方法
CN113004117B (zh) * 2021-04-22 2021-08-13 泉州宇极新材料科技有限公司 气相脱卤化氢制备3,3,3-三氟丙炔的方法
CN114797957A (zh) * 2022-05-12 2022-07-29 辽宁浚成科技有限公司 一种碳酸亚乙烯酯液相合成的固体催化剂及制备方法和应用
CN116120149A (zh) * 2023-04-04 2023-05-16 北京宇极科技发展有限公司 饱和卤代烃脱卤化氢制备含氟炔的方法

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