CN1166479A - 1-氯-3，3，3-三氟丙烯合成方法及其氟化成1，1，1，3，3-五氟丙烷的方法 - Google Patents

1-氯-3，3，3-三氟丙烯合成方法及其氟化成1，1，1，3，3-五氟丙烷的方法 Download PDF

Info

Publication number: CN1166479A
Authority: CN; China
Prior art keywords: carried out; reaction; fluorination; process according; catalyst
Prior art date: 1996-05-13
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.): Pending

Application number

CN 97111593

Other languages

English (en)

Chinese (zh)

Inventor

A·兰兹

L·文德林格

B·勒基米

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.)

Arkema France SA

Original Assignee

Elf Atochem SA

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.)

1996-05-13

Filing date

1997-05-13

Publication date

1997-12-03

1997-05-13 Application filed by Elf Atochem SA filed Critical Elf Atochem SA

1997-12-03 Publication of CN1166479A publication Critical patent/CN1166479A/zh

Status Pending legal-status Critical Current

Links

238000003682 fluorination reaction Methods 0.000 title claims abstract description 47
MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 title claims abstract description 39
LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 title claims abstract description 9
230000015572 biosynthetic process Effects 0.000 title description 4
238000003786 synthesis reaction Methods 0.000 title description 3
238000006243 chemical reaction Methods 0.000 claims abstract description 34
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 27
239000007791 liquid phase Substances 0.000 claims abstract description 18
239000012071 phase Substances 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims description 52
239000003054 catalyst Substances 0.000 claims description 50
230000008569 process Effects 0.000 claims description 46
239000000460 chlorine Substances 0.000 claims description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
229910000423 chromium oxide Inorganic materials 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 9
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 claims description 2
229910044991 metal oxide Inorganic materials 0.000 claims description 2
150000004706 metal oxides Chemical group 0.000 claims description 2
ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 claims 2
CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims 1
PLTIOZOVDUUXDQ-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CC(Cl)Cl PLTIOZOVDUUXDQ-UHFFFAOYSA-N 0.000 claims 1
229910001510 metal chloride Inorganic materials 0.000 claims 1
229910001512 metal fluoride Inorganic materials 0.000 claims 1
QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000006227 byproduct Substances 0.000 description 9
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
238000012360 testing method Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
229910052787 antimony Inorganic materials 0.000 description 4
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052804 chromium Inorganic materials 0.000 description 4
239000011651 chromium Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000011148 porous material Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
RGWOFTGZWJGPHG-NKWVEPMBSA-N (2r)-3-hydroxy-2-[(1r)-2-oxo-1-(6-oxo-3h-purin-9-yl)ethoxy]propanal Chemical compound N1C=NC(=O)C2=C1N([C@@H](C=O)O[C@H](CO)C=O)C=N2 RGWOFTGZWJGPHG-NKWVEPMBSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
229940001007 aluminium phosphate Drugs 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000009172 bursting Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000003380 propellant Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
238000003980 solgel method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 description 1
QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
SFCFZNZZFJRHSD-UHFFFAOYSA-N 1,2,2-trichloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(Cl)(Cl)C(F)(F)Cl SFCFZNZZFJRHSD-UHFFFAOYSA-N 0.000 description 1
OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical class CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
DBUQEYQQFXCLAW-UHFFFAOYSA-N [Sb].ClF Chemical compound [Sb].ClF DBUQEYQQFXCLAW-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 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
239000011324 bead Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000012084 conversion product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
125000005675 difluoroethenyl group Chemical group [H]C(*)=C(F)F 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000013529 heat transfer fluid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910001055 inconels 600 Inorganic materials 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
239000010955 niobium Substances 0.000 description 1
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical class [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
- 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms

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)

CN 97111593 1996-05-13 1997-05-13 1-氯-3，3，3-三氟丙烯合成方法及其氟化成1，1，1，3，3-五氟丙烷的方法 Pending CN1166479A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9605908A FR2748473B1 (fr)	1996-05-13	1996-05-13	Synthese du 1-chloro-3,3,3 trifluoropropene et sa fluoration en 1,1,1,3,3 pentafluoropropane
FR9605908		1996-05-13

Publications (1)

Publication Number	Publication Date
CN1166479A true CN1166479A (zh)	1997-12-03

Family

ID=9492063

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN 97111593 Pending CN1166479A (zh)	1996-05-13	1997-05-13	1-氯-3，3，3-三氟丙烯合成方法及其氟化成1，1，1，3，3-五氟丙烷的方法

Country Status (7)

Country	Link
JP (1)	JPH1087523A (de)
CN (1)	CN1166479A (de)
CA (1)	CA2203433A1 (de)
DE (1)	DE19716337A1 (de)
ES (1)	ES2128256B1 (de)
FR (1)	FR2748473B1 (de)
GB (1)	GB2313118A (de)

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CN102933532A (zh) *	2010-03-10	2013-02-13	霍尼韦尔国际公司	气相生产1-氯-3，3，3-三氟丙烯的催化剂寿命改进
CN101395109B (zh) *	2006-01-03	2013-09-18	霍尼韦尔国际公司	制备氟化有机化合物的方法
CN104058928A (zh) *	2014-06-19	2014-09-24	巨化集团技术中心	一种含溴氟代烷烃合成中提高装置生产能力的方法
CN101550062B (zh) *	2008-04-04	2015-09-02	霍尼韦尔国际公司	2,3,3,3-四氟丙烯(HFO-1234yf)的制备工艺
CN105367377A (zh) *	2010-10-22	2016-03-02	阿克马法国公司	通过五氯丙烷的气相氟化制造2-氯-3,3,3-三氟丙烯的方法
CN106085362A (zh) *	2002-10-25	2016-11-09	霍尼韦尔国际公司	含有氟取代烯烃的组合物
CN107011862A (zh) *	2005-06-24	2017-08-04	霍尼韦尔国际公司	含有经氟取代的烯烃的组合物
CN113549426A (zh) *	2005-03-04	2021-10-26	科慕埃弗西有限公司	包含氟代烯烃的组合物
CN115850020A (zh) *	2022-11-16	2023-03-28	江西中欣埃克盛新材料有限公司	连续联产制备HFO1234ze、HCFO1233zd（E、Z）的方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5710352A (en) *	1996-09-19	1998-01-20	Alliedsignal Inc.	Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene
US5777184A (en) *	1997-06-25	1998-07-07	Alliedsignal Inc.	Preparation of fluoroalkyl compounds and their derivatives
BE1011765A3 (fr)	1998-02-26	2000-01-11	Solvay	Procede d'hydrofluoration d'hydrocarbures.
JP3154702B2 (ja)	1998-02-26	2001-04-09	セントラル硝子株式会社	１，１，１，３，３−ペンタフルオロプロパンの製造方法
EP0939071B1 (de) *	1998-02-26	2003-07-30	Central Glass Company, Limited	Verfahren zur Herstellung von fluorierten Propanen
CN1178883C (zh)	1998-06-02	2004-12-08	纳幕尔杜邦公司	六氟丙烯和任选地其他含氟卤代碳氢化合物的制备方法
DE69930512T2 (de)	1998-06-02	2006-10-05	E.I. Dupont De Nemours And Co., Wilmington	Verfahren zur herstellung von hexafluorpropen aus cc1f2cc1fcf3 und azeotrope von cc1f2cc1fcf3 mit hf
DE69937499T2 (de)	1998-11-13	2008-08-21	Daikin Industries, Ltd.	Azeotropes gemisch aus 1,1,1,3,3-pentafluorpropan und 1,1,1-trifluoro-3-chlor-2-propen, eine methode zur trennung und reinigung derselben und ein verfahren zur herstellung von1,1,1,3,3-pentafluorpropan und 1,1,1-trifluor-3-chlor-2-propen
CN1258505C (zh) *	1999-07-21	2006-06-07	碳卤化合物产品公司	脂肪族碳氟化合物的生产
ES2198385T3 (es) *	2000-05-08	2004-02-01	Atofina Chemicals, Inc.	Preparacion de 245fa.
US6844475B1 (en) *	2003-08-08	2005-01-18	Honeywell International Business Machines	Low temperature production of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd)
US9499729B2 (en) *	2006-06-26	2016-11-22	Honeywell International Inc.	Compositions and methods containing fluorine substituted olefins
EP1968922B1 (de)	2006-01-03	2015-04-22	Honeywell International Inc.	Verfahren zur herstellung fluorinierter organischer verbindungen
PL3135720T3 (pl) *	2007-03-29	2020-11-16	Arkema, Inc.	Kompozycja środka porotwórczego z wodorochlorofluoroolefinową
US20110041529A1 (en) *	2008-05-12	2011-02-24	Arkema Inc.	Compositions of hydrochlorofluoroolefins
US9340758B2 (en)	2008-05-12	2016-05-17	Arkema Inc.	Compositions of hydrochlorofluoroolefins
US8426656B2 (en) *	2010-04-05	2013-04-23	Honeywell International Inc.	Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene
CN101913983B (zh) *	2010-09-07	2013-04-17	西安近代化学研究所	1，1，1，3，3-五氟丙烷的制备方法
US8648221B2 (en)	2011-01-19	2014-02-11	Honeywell International Inc.	Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane
US8436217B2 (en)	2011-04-25	2013-05-07	Honeywell International Inc.	Integrated process to co-produce 1,1,1,3,3-pentafluoropropane, trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene
US9000240B2 (en) *	2011-05-19	2015-04-07	Honeywell International Inc.	Integrated process for the production of 1-chloro-3,3,3-trifluoropropene
US8664456B2 (en)	2012-03-28	2014-03-04	Honeywell International Inc.	Integrated process for the co-production of trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane
EP3170803B1 (de)	2014-07-15	2020-11-11	Central Glass Company, Limited	Verfahren zur herstellung von trans-1-chlor-3,3,3-trifluropropan
FR3027304B1 (fr)	2014-10-16	2018-02-23	Arkema France	Compositions a base de 1,1,1,3,3-pentachloropropane
US20160332935A1 (en) *	2015-05-12	2016-11-17	Honeywell International Inc.	Integrated Process for Making HCFO-1233zd and HFC-245fa
CN108026490B (zh) *	2015-09-04	2020-11-03	Ａｇｃ株式会社	溶剂组合物、清洗方法和涂膜的形成方法
JP6826280B2 (ja)	2016-01-15	2021-02-03	セントラル硝子株式会社	トランス−１−クロロ−３，３，３−トリフルオロプロペンの製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1252182B (de) *	1962-01-13	1967-10-19
JP3369604B2 (ja) *	1992-09-04	2003-01-20	ダイキン工業株式会社	１，１，１，２，３，３−ヘキサフルオロプロパンの製造方法及びテトラフルオロクロロプロペンの製造方法
ATE175180T1 (de) *	1994-07-11	1999-01-15	Allied Signal Inc	Verfahren zur herstellung von 1,1,1,3,3- pentafluorpropan
US5414165A (en) *	1994-07-29	1995-05-09	E. I. Du Pont De Nemours And Company	Process for the manufacture of 1,1,1,3,3,3,-hexafluoropropane
FR2724928B1 (fr) *	1994-09-26	1996-10-31	Atochem Elf Sa	Synthese de 1,1,1,3,3-pentafluoropropane
US5616819A (en) *	1995-08-28	1997-04-01	Laroche Industries Inc.	Process for preparing fluorinated aliphatic compounds
FR2740132B1 (fr) *	1995-10-23	1997-12-19	Solvay	Procede pour la preparation de 1,1,1,3,3-pentafluoropropane

1996
- 1996-05-13 FR FR9605908A patent/FR2748473B1/fr not_active Expired - Fee Related
1997
- 1997-04-20 DE DE1997116337 patent/DE19716337A1/de not_active Withdrawn
- 1997-04-22 CA CA 2203433 patent/CA2203433A1/fr not_active Abandoned
- 1997-04-28 ES ES9700910A patent/ES2128256B1/es not_active Expired - Lifetime
- 1997-05-06 GB GB9709202A patent/GB2313118A/en not_active Withdrawn
- 1997-05-13 CN CN 97111593 patent/CN1166479A/zh active Pending
- 1997-05-13 JP JP12245397A patent/JPH1087523A/ja active Pending

Cited By (16)

* Cited by examiner, † Cited by third party
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Also Published As

Publication number	Publication date
GB2313118A (en)	1997-11-19
ES2128256A1 (es)	1999-05-01
FR2748473B1 (fr)	1998-07-24
ES2128256B1 (es)	2000-01-16
CA2203433A1 (fr)	1997-11-13
JPH1087523A (ja)	1998-04-07
DE19716337A1 (de)	1997-11-20
GB9709202D0 (en)	1997-06-25
FR2748473A1 (fr)	1997-11-14

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2001-08-22	C01	Deemed withdrawal of patent application (patent law 1993)
2001-08-22	WD01	Invention patent application deemed withdrawn after publication