CA1120501A - Procede d'obtention d'hexachlorocyclopentadiene - Google Patents

Procede d'obtention d'hexachlorocyclopentadiene

Info

Publication number: CA1120501A
Authority: CA; Canada
Prior art keywords: process according; polychlorinated; percent; chlorine; chloride
Prior art date: 1977-07-05
Legal status (The legal status 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 status listed.): Expired

Application number

CA000306248A

Other languages

English (en)

Inventor

Arun C. Bose

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Occidental Chemical Corp

Original Assignee

Hooker Chemicals and Plastics Corp

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.)

1977-07-05

Filing date

1978-06-27

Publication date

1982-03-23

1978-06-27 Application filed by Hooker Chemicals and Plastics Corp filed Critical Hooker Chemicals and Plastics Corp

1982-03-23 Application granted granted Critical

1982-03-23 Publication of CA1120501A publication Critical patent/CA1120501A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 42
VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title claims abstract description 12
239000000203 mixture Substances 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 40
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 37
239000000460 chlorine Substances 0.000 claims abstract description 37
229910052801 chlorine Inorganic materials 0.000 claims abstract description 37
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 25
125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 13
239000012808 vapor phase Substances 0.000 claims abstract description 5
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 19
239000000376 reactant Substances 0.000 claims description 17
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
229960003280 cupric chloride Drugs 0.000 claims description 9
229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
229910001514 alkali metal chloride Inorganic materials 0.000 claims description 8
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
-1 hydrocarbon ring compound Chemical class 0.000 claims description 8
235000011164 potassium chloride Nutrition 0.000 claims description 7
239000001103 potassium chloride Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229940045803 cuprous chloride Drugs 0.000 claims description 5
239000011261 inert gas Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 2
239000000575 pesticide Substances 0.000 abstract 1
238000005660 chlorination reaction Methods 0.000 description 28
239000000047 product Substances 0.000 description 20
150000001940 cyclopentanes Chemical class 0.000 description 18
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 8
XZBCEESOMMQJJD-UHFFFAOYSA-N 1,1-dichlorocyclopentane Chemical compound ClC1(Cl)CCCC1 XZBCEESOMMQJJD-UHFFFAOYSA-N 0.000 description 7
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RPUFWOAXMFQSDJ-UHFFFAOYSA-N 1,1,2,3,3,4-hexachlorocyclopentane Chemical compound ClC1CC(Cl)(Cl)C(Cl)C1(Cl)Cl RPUFWOAXMFQSDJ-UHFFFAOYSA-N 0.000 description 5
DMZRCHJVWAKCAX-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octachlorocyclopentene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C1(Cl)Cl DMZRCHJVWAKCAX-UHFFFAOYSA-N 0.000 description 5
ZFMWDTNZPKDVBU-UHFFFAOYSA-N 1,2,3,4-tetrachlorocyclopentane Chemical compound ClC1CC(Cl)C(Cl)C1Cl ZFMWDTNZPKDVBU-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
238000007033 dehydrochlorination reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
GCQVBCUTSZCQBZ-UHFFFAOYSA-N 2,2,3,3,4,4-hexachlorocyclopentan-1-one Chemical compound ClC1(Cl)CC(=O)C(Cl)(Cl)C1(Cl)Cl GCQVBCUTSZCQBZ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000000994 depressogenic effect Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000011833 salt mixture Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000005752 Copper oxychloride Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
WYDUSKDSKCASEF-UHFFFAOYSA-N procyclidine Chemical compound C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCC1 WYDUSKDSKCASEF-UHFFFAOYSA-N 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/02—Monocyclic halogenated hydrocarbons
- C07C23/08—Monocyclic halogenated hydrocarbons with a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000306248A 1977-07-05 1978-06-27 Procede d'obtention d'hexachlorocyclopentadiene Expired CA1120501A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81301377A	1977-07-05	1977-07-05
US813,013		1977-07-05

Publications (1)

Publication Number	Publication Date
CA1120501A true CA1120501A (fr)	1982-03-23

Family

ID=25211217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000306248A Expired CA1120501A (fr)	1977-07-05	1978-06-27	Procede d'obtention d'hexachlorocyclopentadiene

Country Status (8)

Country	Link
JP (1)	JPS5414940A (fr)
BE (1)	BE868778A (fr)
CA (1)	CA1120501A (fr)
DE (1)	DE2829473A1 (fr)
FR (1)	FR2396734A1 (fr)
IL (1)	IL55071A (fr)
IT (1)	IT1097481B (fr)
NL (1)	NL7807301A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105884569A (zh) *	2016-04-22	2016-08-24	北京宇极科技发展有限公司	制备1,2-二氯六氟环戊烯的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE542596A (fr) *
BE506748A (fr) *	1957-07-22
FR1347854A (fr) *	1962-11-21	1964-01-04	Velsicol Chemical Corp	Procédé de production d'hexachlorocyclopentadiène
DE2062773A1 (de) *	1970-12-19	1972-06-22	Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt	Verfahren zur Herstellung von Polychlorcyclopentan und Hexachlorcyclopentadien
US4036897A (en) *	1976-08-04	1977-07-19	The Lummus Company	Production of hexachlorocyclopentadiene

1978
- 1978-06-27 CA CA000306248A patent/CA1120501A/fr not_active Expired
- 1978-07-03 FR FR7819763A patent/FR2396734A1/fr not_active Withdrawn
- 1978-07-04 IL IL55071A patent/IL55071A/xx unknown
- 1978-07-04 JP JP8140278A patent/JPS5414940A/ja active Pending
- 1978-07-05 IT IT25355/78A patent/IT1097481B/it active
- 1978-07-05 NL NL7807301A patent/NL7807301A/xx not_active Application Discontinuation
- 1978-07-05 BE BE189105A patent/BE868778A/fr unknown
- 1978-07-05 DE DE19782829473 patent/DE2829473A1/de not_active Withdrawn

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105884569A (zh) *	2016-04-22	2016-08-24	北京宇极科技发展有限公司	制备1,2-二氯六氟环戊烯的方法

Also Published As

Publication number	Publication date
NL7807301A (nl)	1979-01-09
FR2396734A1 (fr)	1979-02-02
IL55071A0 (en)	1978-09-29
IT7825355A0 (it)	1978-07-05
IT1097481B (it)	1985-08-31
JPS5414940A (en)	1979-02-03
IL55071A (en)	1981-07-31
BE868778A (fr)	1979-01-05
DE2829473A1 (de)	1979-01-18

Legal Events

Date	Code	Title	Description
1999-03-23	MKEX	Expiry

Publication	Publication Date	Title
EP0850210B1 (fr)	2000-09-20	Procede de preparation d'alcanes halogenes
EP1686111B1 (fr)	2010-07-28	Procédé de préparation de 1,1,1,3,3-pentafluoropropane
EP0717728A1 (fr)	1996-06-26	Procede de preparation de pentafluoropropane-1,1,1,3,3
EP0584282B1 (fr)	1999-01-20	Procede d'elaboration du pentafluoroethane
US4754085A (en)	1988-06-28	Process for the preparation of hydrofluoroalkanes
US3591646A (en)	1971-07-06	Process for obtaining halogenated,fluorine containing organic compounds
US4766259A (en)	1988-08-23	Gas-phase fluorination process
US5399549A (en)	1995-03-21	Process for the manufacture of pentafluoroethane
US2446475A (en)	1948-08-03	Rearrangement process
EP0658530B1 (fr)	1998-10-28	Procedes de production du 1,1,1,2,3,3-hexafluoropropane et du tetrafluorochloropropene
US3149170A (en)	1964-09-15	Fluorination of hexachlorobutadiene
US5723684A (en)	1998-03-03	Compositions for bis-(fluoromethyl)ether
US4463200A (en)	1984-07-31	Process for the production of perchloroethylene by catalytic oxychlorination
CA1120501A (fr)	1982-03-23	Procede d'obtention d'hexachlorocyclopentadiene
EP0712826A1 (fr)	1996-05-22	Synthèse de 1,1,1-trifluoroéthane utilisant un acide de Lewis supporté
US3557229A (en)	1971-01-19	Oxychlorination of ethane to vinyl chloride
EP0426343B1 (fr)	1994-02-23	Procédé pour la préparation de 1,1-dichlorotetrafluoroéthane
US2946828A (en)	1960-07-26	Process for preparing aliphatic fluorine compounds
US3398203A (en)	1968-08-20	Process for the preparation of fluorinated hydrocarbons
CA1067518A (fr)	1979-12-04	Preparation de cetones aliphatiques chlorofluorees
US4849561A (en)	1989-07-18	Liquid phase process for dehydrochlorination of haloalkanes in the presence of an initiator based on an organic chlorinated product
US2675413A (en)	1954-04-13	Production of unsaturated halides by exchange of halogen atoms
EP0366404B1 (fr)	1993-01-20	Procédé de préparation de 1,1,1,2-tétrafluoroéthane
US2734090A (en)	1956-02-07	Preparation of vinylidene fluoride
KR790001615B1 (ko)	1979-11-23	메탄을 옥시염소화 시키는 방법

CA1120501A - Procede d'obtention d'hexachlorocyclopentadiene - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=25211217

Family Applications (1)

Country Status (8)

Cited By (1)

Family Cites Families (5)

Cited By (1)

Also Published As

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Legal Events