WO2014052695A1 - Déshydrochloration de réactifs chlorés pour produire le 1,1,1,4,4,4-hexafluoro-2-butyne - Google Patents

Déshydrochloration de réactifs chlorés pour produire le 1,1,1,4,4,4-hexafluoro-2-butyne Download PDF

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Publication number
WO2014052695A1
WO2014052695A1 PCT/US2013/062080 US2013062080W WO2014052695A1 WO 2014052695 A1 WO2014052695 A1 WO 2014052695A1 US 2013062080 W US2013062080 W US 2013062080W WO 2014052695 A1 WO2014052695 A1 WO 2014052695A1
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WO
WIPO (PCT)
Prior art keywords
hexafluoro
salt
butyne
mol
aqueous solution
Prior art date
Application number
PCT/US2013/062080
Other languages
English (en)
Inventor
Sheng Peng
Mario Joseph Nappa
Original Assignee
E. I. Du Pont De Nemours And Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E. I. Du Pont De Nemours And Company filed Critical E. I. Du Pont De Nemours And Company
Priority to US14/416,313 priority Critical patent/US9440896B2/en
Priority to KR1020157007748A priority patent/KR102147909B1/ko
Priority to JP2015534687A priority patent/JP6272877B2/ja
Priority to MX2015003797A priority patent/MX371333B/es
Priority to EP13776644.0A priority patent/EP2922809A1/fr
Priority to CN201380050238.9A priority patent/CN104684877A/zh
Publication of WO2014052695A1 publication Critical patent/WO2014052695A1/fr
Priority to IN1199DEN2015 priority patent/IN2015DN01199A/en

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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de production d'hexafluoro-2-butyne comprenant, la réaction de HCFC-336 avec une solution aqueuse d'un hydroxyde de métal alcalin en présence d'un sel d'alkylammonium quaternaire qui comprend au moins un groupe alkyle d'au moins 8 carbones, et la récupération de l'hexafluoro-2-butyne, la conversion en dichloro-1,1,1,4,4,4-hexafluorobutane étant au moins de 50 % par heure. L'invention concerne également un procédé de production d'hexafluoro-2-butyne comprenant, la réaction de HCFC-336 avec une solution aqueuse d'un hydroxyde de métal alcalin en présence d'un sel d'alkylammonium quaternaire ayant des groupes alkyle de quatre à dix atomes de carbone, et des mélanges de ceux-ci, et d'un tensio-actif non ionique, et la récupération de l'hexafluoro-2-butyne, et la conversion de dichloro-1,1,1,4,4,4-hexafluorobutane en hexafluoro-2-butyne étant au moins de 20 % par heure.
PCT/US2013/062080 2012-09-28 2013-09-27 Déshydrochloration de réactifs chlorés pour produire le 1,1,1,4,4,4-hexafluoro-2-butyne WO2014052695A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US14/416,313 US9440896B2 (en) 2012-09-28 2013-09-27 Dehydrochlorination of HCFC-336 isomers to 1,1,1,4,4,4-hexafluoro-2-butyne
KR1020157007748A KR102147909B1 (ko) 2012-09-28 2013-09-27 1,1,1,4,4,4-헥사플루오로-2-부틴을 제조하기 위한 염소화된 반응물의 탈염화수소화
JP2015534687A JP6272877B2 (ja) 2012-09-28 2013-09-27 １，１，１，４，４，４−ヘキサフルオロ−２−ブチンを製造するための塩素化反応物の脱塩酸
MX2015003797A MX371333B (es) 2012-09-28 2013-09-27 Deshidrocloracion de reactantes clorados para producir 1,1,1,4,4,4-hexafluoro-2-butino.
EP13776644.0A EP2922809A1 (fr) 2012-09-28 2013-09-27 Déshydrochloration de réactifs chlorés pour produire le 1,1,1,4,4,4-hexafluoro-2-butyne
CN201380050238.9A CN104684877A (zh) 2012-09-28 2013-09-27 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔
IN1199DEN2015 IN2015DN01199A (fr) 2012-09-28 2015-02-13

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261707220P 2012-09-28 2012-09-28
US201261707231P 2012-09-28 2012-09-28
US61/707,231 2012-09-28
US61/707,220 2012-09-28

Publications (1)

Publication Number Publication Date
WO2014052695A1 true WO2014052695A1 (fr) 2014-04-03

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2013/062080 WO2014052695A1 (fr) 2012-09-28 2013-09-27 Déshydrochloration de réactifs chlorés pour produire le 1,1,1,4,4,4-hexafluoro-2-butyne

Country Status (7)

Country Link
EP (1) EP2922809A1 (fr)
JP (1) JP6272877B2 (fr)
KR (1) KR102147909B1 (fr)
CN (2) CN108530261A (fr)
IN (1) IN2015DN01199A (fr)
MX (1) MX371333B (fr)
WO (1) WO2014052695A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9328042B2 (en) 2014-08-11 2016-05-03 The Chemours Company Fc, Llc Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene
US9440896B2 (en) 2012-09-28 2016-09-13 The Chemours Company Fc, Llc Dehydrochlorination of HCFC-336 isomers to 1,1,1,4,4,4-hexafluoro-2-butyne
WO2019023572A1 (fr) 2017-07-27 2019-01-31 The Chemours Company Fc, Llc Procédé de préparation de (z)-1,1,1,4,4,4-hexafluoro-2-butène
CN114409514A (zh) * 2021-12-21 2022-04-29 西安近代化学研究所 一种1,1,1,4,4,4-六氟-2-丁酮的合成方法
US20220194879A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US20220194882A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US20220194881A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US11655199B2 (en) 2019-02-21 2023-05-23 Daikin Industries, Ltd. Methods for producing halogenated alkene compound and fluorinated alkyne compound

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106536462B (zh) * 2014-02-07 2019-10-18 科慕埃弗西有限公司 用于制备z-1，1，1，4，4，4-六氟-2-丁烯的一体化方法
CN106349007B (zh) * 2016-08-22 2019-06-11 巨化集团技术中心 一种z-hfo-1336的制备方法
WO2020171011A1 (fr) * 2019-02-21 2020-08-27 ダイキン工業株式会社 Composé alcène halogéné et procédé de fabrication d'un composé alcyne fluoré
CN110950735B (zh) * 2019-10-22 2022-08-30 浙江巨化技术中心有限公司 一种气相法制备1,1,1,4,4,4-六氟-2-丁炔的方法
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
JP2023516058A (ja) * 2020-03-04 2023-04-17 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー （ｚ）－１，１，１，４，４，４－ヘキサフルオロ－２－ブテン及び中間体を生成するためのプロセス

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US20110288346A1 (en) * 2010-05-21 2011-11-24 Honeywell International Inc. Process for cis 1,1,1,4,4,4-hexafluoro-2-butene

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US6548719B1 (en) * 2001-09-25 2003-04-15 Honeywell International Process for producing fluoroolefins
JP5380882B2 (ja) * 2007-04-17 2014-01-08 セントラル硝子株式会社 ３，３，３−トリフルオロプロピンの製造方法
JP5056946B2 (ja) * 2007-09-11 2012-10-24 ダイキン工業株式会社 ２，３，３，３−テトラフルオロプロペンの製造方法
JP2010037205A (ja) * 2008-07-31 2010-02-18 Nippon Zeon Co Ltd フッ素アルカン化合物、その製造方法及びパーフルオロアルキン化合物の製造方法
US8667404B2 (en) * 2008-08-06 2014-03-04 Autodesk, Inc. Predictive material editor

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US20110288346A1 (en) * 2010-05-21 2011-11-24 Honeywell International Inc. Process for cis 1,1,1,4,4,4-hexafluoro-2-butene

Non-Patent Citations (2)

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A. KOLOMEITSEV, ET AL.: "Advances in trifluoromethylating phosphorus compounds", PHOSPHORUS, SULFUR, AND SILICON, vol. 109, no. 1-4, 1996, Taylor & Francis, Abingdon, GB, pages 597 - 600, XP008166507, ISSN: 1042-6507, DOI: 10.1080/10426509608545224 *
R.N. HASZELDINE: "The addition of free radicals to unsaturated systems. Part I. The direction of radical addition to 3 : 3 : 3-trifluoropropene", JOURNAL OF THE CHEMICAL SOCIETY, 1952, Royal Society of Chemistry, Cambridge, GB, pages 2504 - 2513, XP008084552, ISSN: 0368-1769, DOI: 10.1039/jr9520002504 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9440896B2 (en) 2012-09-28 2016-09-13 The Chemours Company Fc, Llc Dehydrochlorination of HCFC-336 isomers to 1,1,1,4,4,4-hexafluoro-2-butyne
US9328042B2 (en) 2014-08-11 2016-05-03 The Chemours Company Fc, Llc Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene
WO2019023572A1 (fr) 2017-07-27 2019-01-31 The Chemours Company Fc, Llc Procédé de préparation de (z)-1,1,1,4,4,4-hexafluoro-2-butène
CN111201211A (zh) * 2017-07-27 2020-05-26 科慕埃弗西有限公司 制备(z)-1，1，1，4，4，4-六氟-2-丁烯的方法
CN111201211B (zh) * 2017-07-27 2023-12-05 科慕埃弗西有限公司 制备(z)-1，1，1，4，4，4-六氟-2-丁烯的方法
US11655199B2 (en) 2019-02-21 2023-05-23 Daikin Industries, Ltd. Methods for producing halogenated alkene compound and fluorinated alkyne compound
US20220194879A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US20220194882A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US20220194881A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
US11912639B2 (en) * 2019-04-05 2024-02-27 The Chemours Company Fc, Llc Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
CN114409514A (zh) * 2021-12-21 2022-04-29 西安近代化学研究所 一种1,1,1,4,4,4-六氟-2-丁酮的合成方法

Also Published As

Publication number Publication date
JP6272877B2 (ja) 2018-01-31
IN2015DN01199A (fr) 2015-06-26
JP2015530417A (ja) 2015-10-15
CN108530261A (zh) 2018-09-14
KR20150061638A (ko) 2015-06-04
EP2922809A1 (fr) 2015-09-30
MX2015003797A (es) 2015-07-14
CN104684877A (zh) 2015-06-03
KR102147909B1 (ko) 2020-08-25
MX371333B (es) 2020-01-27

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