DE60011118T2 - Verfahren zur herstellung von halogenierten kohlenwasserstoffen - Google Patents
Verfahren zur herstellung von halogenierten kohlenwasserstoffen Download PDFInfo
- Publication number
- DE60011118T2 DE60011118T2 DE60011118T DE60011118T DE60011118T2 DE 60011118 T2 DE60011118 T2 DE 60011118T2 DE 60011118 T DE60011118 T DE 60011118T DE 60011118 T DE60011118 T DE 60011118T DE 60011118 T2 DE60011118 T2 DE 60011118T2
- Authority
- DE
- Germany
- Prior art keywords
- olefin
- catalyst
- process according
- reaction
- halogenated
- Prior art date
- 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 - Lifetime
Links
- 150000008282 halocarbons Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001336 alkenes Chemical class 0.000 claims abstract description 35
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012429 reaction media Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 41
- 239000003426 co-catalyst Substances 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 10
- FFBFEBDZFWMXBE-UHFFFAOYSA-N 1,1,1,3,3-pentachlorobutane Chemical compound CC(Cl)(Cl)CC(Cl)(Cl)Cl FFBFEBDZFWMXBE-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000001880 copper compounds Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- GMWOFVVPEWUYMH-UHFFFAOYSA-N 1,1,1,3,3-pentachloro-2-methylpropane Chemical compound ClC(Cl)C(C)C(Cl)(Cl)Cl GMWOFVVPEWUYMH-UHFFFAOYSA-N 0.000 claims description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 claims description 2
- PANVCEBTPSTUEL-UHFFFAOYSA-N 1,1,2,3,3-pentachloropropane Chemical compound ClC(Cl)C(Cl)C(Cl)Cl PANVCEBTPSTUEL-UHFFFAOYSA-N 0.000 claims description 2
- NGAUWAOLBDDRKB-UHFFFAOYSA-N 1,1,3,3-tetrachlorobutane Chemical compound CC(Cl)(Cl)CC(Cl)Cl NGAUWAOLBDDRKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 30
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical class CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 2
- OWXJKYNZGFSVRC-UHFFFAOYSA-N 1-chloroprop-1-ene Chemical class CC=CCl OWXJKYNZGFSVRC-UHFFFAOYSA-N 0.000 description 2
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- -1 copper (II) halides Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- PPDZLUVUQQGIOJ-UHFFFAOYSA-N 1-dihexylphosphorylhexane Chemical compound CCCCCCP(=O)(CCCCCC)CCCCCC PPDZLUVUQQGIOJ-UHFFFAOYSA-N 0.000 description 1
- XHRRUIJGMKIISX-UHFFFAOYSA-N 1-dihexylphosphoryloctane Chemical compound CCCCCCCCP(=O)(CCCCCC)CCCCCC XHRRUIJGMKIISX-UHFFFAOYSA-N 0.000 description 1
- JRBAVVHMQRKGLN-UHFFFAOYSA-N 16,16-dimethylheptadecan-1-amine Chemical compound CC(C)(C)CCCCCCCCCCCCCCCN JRBAVVHMQRKGLN-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003481 tantalum Chemical class 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99203270 | 1999-10-06 | ||
| EP99203270 | 1999-10-06 | ||
| PCT/EP2000/009490 WO2001025176A1 (fr) | 1999-10-06 | 2000-09-26 | Procede de preparation d'hydrocarbures halogenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60011118D1 DE60011118D1 (de) | 2004-07-01 |
| DE60011118T2 true DE60011118T2 (de) | 2005-07-07 |
Family
ID=8240721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60011118T Expired - Lifetime DE60011118T2 (de) | 1999-10-06 | 2000-09-26 | Verfahren zur herstellung von halogenierten kohlenwasserstoffen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6369285B1 (OSRAM) |
| EP (1) | EP1222154B1 (OSRAM) |
| JP (1) | JP2004500339A (OSRAM) |
| AT (1) | ATE267790T1 (OSRAM) |
| AU (1) | AU7784500A (OSRAM) |
| DE (1) | DE60011118T2 (OSRAM) |
| ES (1) | ES2220547T3 (OSRAM) |
| WO (1) | WO2001025176A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500995B1 (en) * | 2001-06-14 | 2002-12-31 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3,-pentachloropropane |
| EP1447133B1 (en) * | 2001-10-24 | 2012-04-04 | Daikin Industries, Ltd. | Method for the recovery of catalysts in a process for the production of perfluoroalkyl iodide telomers |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| US9738577B2 (en) * | 2006-10-11 | 2017-08-22 | Honeywell International Inc. | Process for the manufacture of 1,1,1,3,3-pentachloropropane |
| CN100406417C (zh) * | 2006-11-17 | 2008-07-30 | 浙江蓝天环保高科技股份有限公司 | 以2-氯丙烯和四氯化碳为原料在调聚催化剂下制备1,1,1,3,3-五氯丁烷的方法 |
| GB0806389D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0806419D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE622938A (OSRAM) * | 1961-09-28 | |||
| US3454657A (en) * | 1967-08-24 | 1969-07-08 | Dow Chemical Co | Catalytic synthesis of organic halogen compounds |
| FR2120337A5 (OSRAM) * | 1970-12-30 | 1972-08-18 | Rhone Progil | |
| DE3460965D1 (en) * | 1983-07-06 | 1986-11-20 | Monsanto Co | Process for producing monoadducts of olefins and telogens reactive therewith |
| ES2104521T3 (es) | 1994-07-11 | 1999-05-01 | Allied Signal Inc | Proceso para la fabricacion de 1,1,1,3,3-pentafluoropropano. |
| AU6685796A (en) * | 1995-08-01 | 1997-02-26 | E.I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons |
| US5902914A (en) * | 1995-08-14 | 1999-05-11 | Alliedsignal Inc. | Process for the preparation of halogenated alkanes |
| FR2744442B1 (fr) * | 1996-02-01 | 1998-02-27 | Atochem Elf Sa | Preparation du 1,1,1,3,3-pentachlorobutane et du 1,1,1,3,3,-pentafluorobutane |
| CA2277169C (en) | 1997-01-16 | 2007-10-02 | E.I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons |
| BR9808730B1 (pt) * | 1997-05-05 | 2009-01-13 | processo de preparação de 1,1,1,3,3-pentaclorobutano. | |
| ES2218829T3 (es) * | 1997-05-05 | 2004-11-16 | Solvay (Societe Anonyme) | Procedimiento de preparacion de hidrocarburos halogenados. |
-
2000
- 2000-09-26 WO PCT/EP2000/009490 patent/WO2001025176A1/fr not_active Ceased
- 2000-09-26 DE DE60011118T patent/DE60011118T2/de not_active Expired - Lifetime
- 2000-09-26 AU AU77845/00A patent/AU7784500A/en not_active Abandoned
- 2000-09-26 ES ES00967818T patent/ES2220547T3/es not_active Expired - Lifetime
- 2000-09-26 AT AT00967818T patent/ATE267790T1/de not_active IP Right Cessation
- 2000-09-26 EP EP00967818A patent/EP1222154B1/fr not_active Expired - Lifetime
- 2000-09-26 JP JP2001528127A patent/JP2004500339A/ja active Pending
- 2000-09-29 US US09/677,127 patent/US6369285B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004500339A (ja) | 2004-01-08 |
| DE60011118D1 (de) | 2004-07-01 |
| ATE267790T1 (de) | 2004-06-15 |
| EP1222154B1 (fr) | 2004-05-26 |
| ES2220547T3 (es) | 2004-12-16 |
| EP1222154A1 (fr) | 2002-07-17 |
| AU7784500A (en) | 2001-05-10 |
| WO2001025176A1 (fr) | 2001-04-12 |
| US6369285B1 (en) | 2002-04-09 |
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