CA1321797C - Procede pour la preparation de telomeres derives du chlorotrifluoroethylene et du 1,1dibromo-1-chlorotrifluoroethane - Google Patents

Procede pour la preparation de telomeres derives du chlorotrifluoroethylene et du 1,1dibromo-1-chlorotrifluoroethane

Info

Publication number: CA1321797C
Authority: CA; Canada
Prior art keywords: telomers; reaction; psi; conducted; chlorotrifluoroethylene
Prior art date: 1987-11-05
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 - Fee Related

Application number

CA000567738A

Other languages

English (en)

Inventor

David Y. Tang

Bobby F. Dannels

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

Occidental Chemical 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.)

1987-11-05

Filing date

1988-05-26

Publication date

1993-08-31

1988-05-26 Application filed by Occidental Chemical Corp filed Critical Occidental Chemical Corp

1993-08-31 Application granted granted Critical

1993-08-31 Publication of CA1321797C publication Critical patent/CA1321797C/fr

2010-08-31 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 title claims abstract description 36
238000004519 manufacturing process Methods 0.000 title claims description 6
WGIRTDAEWOUFQR-UHFFFAOYSA-N 1,1-dibromo-1-chloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Br)Br WGIRTDAEWOUFQR-UHFFFAOYSA-N 0.000 title abstract 2
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 18
239000003054 catalyst Substances 0.000 claims abstract description 17
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims abstract description 14
239000003638 chemical reducing agent Substances 0.000 claims abstract description 14
229910015400 FeC13 Inorganic materials 0.000 claims abstract description 13
150000002736 metal compounds Chemical class 0.000 claims abstract description 13
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims abstract description 10
229910052759 nickel Inorganic materials 0.000 claims abstract description 10
244000028419 Styrax benzoin Species 0.000 claims abstract description 7
235000000126 Styrax benzoin Nutrition 0.000 claims abstract description 7
235000008411 Sumatra benzointree Nutrition 0.000 claims abstract description 7
229960002130 benzoin Drugs 0.000 claims abstract description 7
235000019382 gum benzoic Nutrition 0.000 claims abstract description 7
229910021576 Iron(III) bromide Inorganic materials 0.000 claims abstract description 6
229910010066 TiC14 Inorganic materials 0.000 claims abstract description 6
229910052742 iron Inorganic materials 0.000 claims abstract description 6
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims abstract description 6
229910021590 Copper(II) bromide Inorganic materials 0.000 claims abstract description 5
229910052802 copper Inorganic materials 0.000 claims abstract description 5
229910052719 titanium Inorganic materials 0.000 claims abstract description 5
229910052720 vanadium Inorganic materials 0.000 claims abstract description 5
229910021589 Copper(I) bromide Inorganic materials 0.000 claims abstract description 4
229910021575 Iron(II) bromide Inorganic materials 0.000 claims abstract description 4
229910000359 iron(II) sulfate Inorganic materials 0.000 claims abstract description 4
GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims abstract description 4
-1 CuC12 Inorganic materials 0.000 claims abstract description 3
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 23
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
238000009826 distribution Methods 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 5
239000010936 titanium Substances 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
239000012530 fluid Substances 0.000 abstract description 5
229910021591 Copper(I) chloride Inorganic materials 0.000 abstract description 3
JQGGAELIYHNDQS-UHFFFAOYSA-N Nic 12 Natural products CC(C=CC(=O)C)c1ccc2C3C4OC4C5(O)CC=CC(=O)C5(C)C3CCc2c1 JQGGAELIYHNDQS-UHFFFAOYSA-N 0.000 abstract description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 abstract description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 2
229910000360 iron(III) sulfate Inorganic materials 0.000 abstract description 2
239000000047 product Substances 0.000 description 21
239000000460 chlorine Substances 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
229940124024 weight reducing agent Drugs 0.000 description 10
150000001875 compounds Chemical class 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Chemical group 0.000 description 6
239000000203 mixture Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000011010 flushing procedure Methods 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000003797 telogen phase Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
125000001246 bromo group Chemical class Br* 0.000 description 3
235000017168 chlorine Nutrition 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229940060038 chlorine Drugs 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
230000002730 additional effect Effects 0.000 description 2
239000013627 low molecular weight specie Substances 0.000 description 2
229910001507 metal halide Inorganic materials 0.000 description 2
150000005309 metal halides Chemical class 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
241000894007 species Species 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
CALRXIQBQWFLRG-UHFFFAOYSA-N 1,1,1-tribromo-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Br)(Br)Br CALRXIQBQWFLRG-UHFFFAOYSA-N 0.000 description 1
PFSLUJSDDNGKIZ-UHFFFAOYSA-N 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane Chemical compound FC(F)(Br)C(F)(Cl)C(F)(Cl)C(F)(F)Br PFSLUJSDDNGKIZ-UHFFFAOYSA-N 0.000 description 1
RKKGNUHLABLELO-UHFFFAOYSA-N 1,6-dibromo-2,3,5-trichloro-1,1,2,3,4,4,5,6,6-nonafluorohexane Chemical compound FC(F)(Br)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(Cl)C(F)(F)Br RKKGNUHLABLELO-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910017358 Fe2(SO4) Inorganic materials 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
238000005253 cladding Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000004519 grease Substances 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons

Landscapes

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

CA000567738A 1987-11-05 1988-05-26 Procede pour la preparation de telomeres derives du chlorotrifluoroethylene et du 1,1dibromo-1-chlorotrifluoroethane Expired - Fee Related CA1321797C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11699087A	1987-11-05	1987-11-05
US116,990		1987-11-05

Publications (1)

Publication Number	Publication Date
CA1321797C true CA1321797C (fr)	1993-08-31

Family

ID=22370438

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000567738A Expired - Fee Related CA1321797C (fr)	1987-11-05	1988-05-26	Procede pour la preparation de telomeres derives du chlorotrifluoroethylene et du 1,1dibromo-1-chlorotrifluoroethane

Country Status (5)

Country	Link
JP (1)	JPH01135733A (fr)
CA (1)	CA1321797C (fr)
DE (1)	DE3820934A1 (fr)
FR (1)	FR2622883A1 (fr)
GB (1)	GB2211838B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2630367A (en)	2023-05-25	2024-11-27	Tailfin Ltd	External pocket for luggage pack

1988
- 1988-05-25 GB GB8812352A patent/GB2211838B/en not_active Expired - Fee Related
- 1988-05-26 CA CA000567738A patent/CA1321797C/fr not_active Expired - Fee Related
- 1988-06-13 JP JP63145548A patent/JPH01135733A/ja active Pending
- 1988-06-21 DE DE19883820934 patent/DE3820934A1/de not_active Withdrawn
- 1988-06-27 FR FR8808610A patent/FR2622883A1/fr active Pending

Also Published As

Publication number	Publication date
GB2211838B (en)	1991-08-21
GB2211838A (en)	1989-07-12
GB8812352D0 (en)	1988-06-29
FR2622883A1 (fr)	1989-05-12
DE3820934A1 (de)	1989-05-18
JPH01135733A (ja)	1989-05-29

Legal Events

Date	Code	Title	Description
1997-09-02	MKLA	Lapsed

Publication	Publication Date	Title
US2668182A (en)	1954-02-02	Polyunsaturated fluoroolefins
DE68916974T2 (de)	1994-12-22	Aluminiumfluorid katalysator und seine verwendung in einem chlorofluorierungsverfahren zur herstellung von 1,1-dichlor-1,2,2,2-tetrafluorethan.
DE69202207T2 (de)	1995-11-30	Verfahren zur Herstellung von 1-Chlor-1,1,3,3,3-Pentafluorpropan und von 1,1,1,3,3,3-Hexafluorpropan.
JPS6029364B2 (ja)	1985-07-10	アルキルベンゼンの直接塩素化法
US2770659A (en)	1956-11-13	Telomerization with sulfuryl halide and product thereof
CA1321797C (fr)	1993-08-31	Procede pour la preparation de telomeres derives du chlorotrifluoroethylene et du 1,1dibromo-1-chlorotrifluoroethane
US4691065A (en)	1987-09-01	Chlorotrifluoroethylene telomerization process
US6002055A (en)	1999-12-14	Process for making dihalodifluoromethanes and their homologues
US4577044A (en)	1986-03-18	Preparation of chlorotrifluoroethylene telomers with fluoroxytrifluoromethane
US2975220A (en)	1961-03-14	Fluorinated organic compounds
US5484932A (en)	1996-01-16	Halogenation processes in advantageous solvents, and novel bistrifluoromethyl-polyfluoroalkoxybenzenes
EP0093580B1 (fr)	1986-12-10	Procédé pour la télomérisation de chlorotrifluoro-éthène
US5347059A (en)	1994-09-13	Process for preparing 1,1-dichloro-1,3,3,3-tetra-fluoropropane
US4808760A (en)	1989-02-28	Telomers prepared from chlorotrifluoroethylene and 1,2-dibromo-2-chlorotrifluoroethane
DE60007111T2 (de)	2004-10-28	Herstellung von ausgewählten fluorolefinen
US4947006A (en)	1990-08-07	Process for preparing fluorinated conjugated olefinic products and new products thus obtained
US4731170A (en)	1988-03-15	Process for preparing alpha, omega-haloperfluoroalkanes
JP2506999B2 (ja)	1996-06-12	クロロトリフルオロエチレン及びトリフルオロトリクロロエタンからテロマ―を調製する方法
US4533762A (en)	1985-08-06	Preparation of chlorotrifluoroethylene telomers with bisfluoroxydifluoromethane
US2552607A (en)	1951-05-15	Halogenated aromatic hydrocarbons and process for making same
US2886607A (en)	1959-05-12	Fluorination of telomers
CA1242460A (fr)	1988-09-27	Couplage de chloroperfluoroalcanes
US4760208A (en)	1988-07-26	Process for coupling telomers of chlorotrifluoroethylene
Boutevin et al.	1986	Synthesis of block cotelomers involving a perfluorinated chain and a hydrophilic chain. Part I. Use of fluorinated telogens with trichloromethyl end groups
US4873382A (en)	1989-10-10	Purification of telomers prepared from chlorotrifluoroethylene and trichlorotrifluoroethane