JPH09508138A - 1,1,1,3,3−ペンタフルオロプロパンの製造法 - Google Patents
1,1,1,3,3−ペンタフルオロプロパンの製造法Info
- Publication number
- JPH09508138A JPH09508138A JP8504369A JP50436996A JPH09508138A JP H09508138 A JPH09508138 A JP H09508138A JP 8504369 A JP8504369 A JP 8504369A JP 50436996 A JP50436996 A JP 50436996A JP H09508138 A JPH09508138 A JP H09508138A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chcl
- ccl
- pentavalent
- chf
- 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.)
- Granted
Links
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 31
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 19
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 17
- -1 pentavalent antimony halide Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052758 niobium Inorganic materials 0.000 claims description 7
- 239000010955 niobium Substances 0.000 claims description 7
- 229910052715 tantalum Inorganic materials 0.000 claims description 6
- 229910052785 arsenic Inorganic materials 0.000 claims description 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 5
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000004604 Blowing Agent Substances 0.000 abstract description 3
- 239000003380 propellant Substances 0.000 abstract description 3
- 239000011551 heat transfer agent Substances 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical compound [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910000792 Monel Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000005437 stratosphere Substances 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-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
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- 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
-
- 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
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)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.a)式: CFyCl3-yCH2CHFwCl2-w (式中、wは0又は1であり、そしてyは0〜3である。) で表される化合物をフッ化水素と、フッ素化触媒の存在下、式CF3CH2CF2 Hなる化合物を生成させるに十分な条件下で反応させる 工程を含んで成る、1,1,1,3,3−ペンタフルオロプロパンの製造法。 2.フッ素化触媒がハロゲン化五価アンチモン、ハロゲン化五価ニオブ、ハロ ゲン化五価ヒ素及びハロゲン化五価タンタル、混合ハロゲン化五価アンチモン、 混合ハロゲン化五価ニオブ、混合ハロゲン化五価ヒ素及び混合ハロゲン化五価タ ンタル並びにそれらの混合物から成る群より選ばれる、請求項1に記載の方法。 3.フッ素化触媒が式SbClnF5-n(但し、nは0〜5である)を有する、 請求項2に記載の方法。 4.式CFyCl3-yCH2CHFwCl2-wで表される化合物が、CCl3CH2 CHCl2、CF3CH2CHCl2、CFCl2CH2CHCl2、CF2ClCH2 CHCl2、CFCl2CH2CHClF、CF2ClCH2CHFCl及びCF3C H2CHFClから成る群より選ばれる、請求項2に記載の方法。 5.式CFyCl3-yCH2CHFwCl2-wで表される化合物がCCl3CH2C HCl2である、請求項2に記載の方法。 6.反応が約50〜約175℃の温度で行われる、請求項1に記載の方法。 7.使用されるHFの量が、式CFyCl3-yCH2CHFwCl2-wで表される 化合物に対するHFの化学量論量の約1〜約15倍である、請求項1に記載の方 法。 8.フッ素化触媒が、存在する式CFyCl3-yCH2CHFwCl2-wで表され る化合物の量に対して約5〜約50重量%の量で存在する、請求項7に記載の方 法。 9.次の: a)CCl4と塩化ビニルとを、式CCl3CH2CHCl2なる化合物を生成さ せるに十分な条件下で反応させ;そして b)式CCl3CH2CHCl2なる化合物とフッ化水素とを、フッ素化触媒の 存在下で反応させて式CF3CH2CF2Hで表される化合物を生成させる 工程を含んで成る、1,1,1,3,3−ペンタフルオロプロパンの製造法。 10.CCl3CH2CHCl2を工程bに先立って回収する、請求項9に記載 の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27355394A | 1994-07-11 | 1994-07-11 | |
US273,553 | 1994-07-11 | ||
US08/273,553 | 1994-07-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH09508138A true JPH09508138A (ja) | 1997-08-19 |
JP2818035B2 JP2818035B2 (ja) | 1998-10-30 |
Family
ID=23044411
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8504369A Expired - Lifetime JP2818035B2 (ja) | 1994-07-11 | 1995-07-05 | 1,1,1,3,3−ペンタフルオロプロパンの製造法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5574192A (ja) |
EP (1) | EP0770048B1 (ja) |
JP (1) | JP2818035B2 (ja) |
KR (1) | KR100240375B1 (ja) |
CN (1) | CN1063736C (ja) |
AT (1) | ATE175180T1 (ja) |
AU (1) | AU688925B2 (ja) |
BR (1) | BR9508233A (ja) |
CZ (1) | CZ7197A3 (ja) |
DE (2) | DE770048T1 (ja) |
DK (1) | DK0770048T3 (ja) |
ES (1) | ES2104521T3 (ja) |
GR (2) | GR970300031T1 (ja) |
HU (1) | HUT75954A (ja) |
WO (1) | WO1996001797A1 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000017136A1 (fr) * | 1998-09-22 | 2000-03-30 | Daikin Industries, Ltd. | Production de 1,1,1,3,3-pentafluoro-propane et/ou de 1-chloro-3,3,3-trifluoropropene |
JP2002504528A (ja) * | 1998-02-26 | 2002-02-12 | ソルヴェイ | クロロ炭化水素のフッ化水素化方法 |
JP2004500339A (ja) | 1999-10-06 | 2004-01-08 | ソルヴェイ | ハロゲン化炭化水素の製造方法 |
JP2007535570A (ja) * | 2004-04-29 | 2007-12-06 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3,3,3−テトラフルオロプロペンの合成方法 |
JP2009084290A (ja) * | 1995-10-23 | 2009-04-23 | Solvay (Sa) | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
JP2018515522A (ja) * | 2015-05-12 | 2018-06-14 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | HCFO−1233zd及びHFC−245faを製造するための統合方法 |
JP2021073172A (ja) * | 2013-03-13 | 2021-05-13 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 1,3,3−トリクロロ−1,1−ジフルオロプロパンおよびフッ化水素の共沸組成物 |
Families Citing this family (96)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3407379B2 (ja) * | 1993-06-10 | 2003-05-19 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
EP0729932A1 (en) * | 1995-03-03 | 1996-09-04 | Central Glass Company, Limited | Method of producing halopropane |
US6755942B1 (en) * | 1995-08-01 | 2004-06-29 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with HF |
AU6643696A (en) | 1995-08-01 | 1997-02-26 | E.I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with hf |
JP3414562B2 (ja) * | 1995-10-13 | 2003-06-09 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
US6235951B1 (en) | 1996-01-17 | 2001-05-22 | Central Glass Company, Limited | Method for producing 1,1,1,3,3-pentafluoropropane |
JP2933014B2 (ja) * | 1996-01-23 | 1999-08-09 | ダイキン工業株式会社 | ペンタフルオロプロパンとフッ化水素の共沸混合物およびペンタフルオロプロパンの分離精製方法 |
US6316681B1 (en) | 1996-03-05 | 2001-11-13 | Central Glass Company, Limited | Method for producing 1,1,1,3,3-pentafluoropropane |
FR2748473B1 (fr) * | 1996-05-13 | 1998-07-24 | Atochem Elf Sa | Synthese du 1-chloro-3,3,3 trifluoropropene et sa fluoration en 1,1,1,3,3 pentafluoropropane |
US5817893A (en) * | 1996-06-18 | 1998-10-06 | E. I. Du Pont De Nemours And Company | Processes for the manufacture and purification of 1,1,2,2,3,3,4,4-octafluorobutane and by-products |
US6111150A (en) * | 1996-06-20 | 2000-08-29 | Central Glass Company, Limited | Method for producing 1,1,1,3,3,-pentafluoropropane |
US5763706A (en) * | 1996-07-03 | 1998-06-09 | Alliedsignal Inc. | Process for the manufacture of 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3,3-hexafluoropropane |
US6001796A (en) * | 1996-07-03 | 1999-12-14 | Alliedsignal Inc. | Azeotrope-like compositions of 1,1,1,3,3-pentafluoropropane and hydrogen fluoride |
US6040487A (en) * | 1996-07-31 | 2000-03-21 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons |
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 |
US6023004A (en) * | 1996-11-12 | 2000-02-08 | Alliedsignal, Inc. | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon |
EP0864554B1 (en) * | 1997-03-11 | 2002-09-18 | Central Glass Company, Limited | Method for purifying crude 1,1,1,3,3-pentafluoropropane |
BE1011319A3 (fr) | 1997-05-05 | 1999-07-06 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
CZ297256B6 (cs) | 1997-05-05 | 2006-10-11 | Solvay (Societe Anonyme) | Zpusob výroby 1,1,1,3,3-pentachlorbutanu |
US5777184A (en) * | 1997-06-25 | 1998-07-07 | Alliedsignal Inc. | Preparation of fluoroalkyl compounds and their derivatives |
US5969198A (en) * | 1997-06-27 | 1999-10-19 | Alliedsignal Inc. | Process for the preparation of 1,1,1,3,3-pentafluoropropane |
AU733972B2 (en) * | 1997-07-25 | 2001-05-31 | Honeywell International, Inc. | Cleaning vapor compression systems |
ES2189240T3 (es) | 1997-08-08 | 2003-07-01 | Solvay | Procedimiento de preparacion de hidrocarburos halogenados. |
FR2768717B1 (fr) * | 1997-09-24 | 1999-11-12 | Solvay | Procede de separation de fluorure d'hydrogene de ses melanges avec un hydrofluoroalcane contenant de 3 a 6 atomes de carbone |
US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
US6120697A (en) | 1997-12-31 | 2000-09-19 | Alliedsignal Inc | Method of etching using hydrofluorocarbon compounds |
US6635185B2 (en) | 1997-12-31 | 2003-10-21 | Alliedsignal Inc. | Method of etching and cleaning using fluorinated carbonyl compounds |
US6100229A (en) * | 1998-01-12 | 2000-08-08 | Alliedsignal Inc. | Compositions of 1,1,1,3,3,-pentafluoropropane and chlorinated ethylenes |
AU2686399A (en) * | 1998-02-19 | 1999-09-06 | Allied-Signal Inc. | Sterilizing compositions of pentafluoropropane and ethylene oxide |
US6187976B1 (en) | 1998-04-09 | 2001-02-13 | Alliedsignal Inc. | Process for the preparation of fluorine containing hydrohalocarbons |
US6153802A (en) * | 1998-05-08 | 2000-11-28 | Alliedsignal Inc. | Liquid-fluorination system and method |
US6235265B1 (en) | 1998-10-28 | 2001-05-22 | Alliedsignal Inc. | Evaporative coolant for topical anesthesia comprising hydrofluorocarbons and/or hydrochlorofluorocarbons |
BE1012268A3 (fr) | 1998-11-05 | 2000-08-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
JP4389389B2 (ja) | 1998-11-13 | 2009-12-24 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンおよび1,1,1−トリフルオロ−3−クロロ−2−プロペンから成る共沸組成物およびそれを用いる分離精製方法、ならびに1,1,1,3,3−ペンタフルオロプロパンおよび1,1,1−トリフルオロ−3−クロロ−2−プロペンの製造方法 |
US6086788A (en) | 1999-03-15 | 2000-07-11 | Alliedsignal Inc. | Hydrofluorocarbon blown foam and method for preparation thereof |
US6846963B2 (en) | 1999-11-15 | 2005-01-25 | Daikin Industries, Ltd. | Process for producing 1,1,1,3,3-pentafluoropropane |
US6521802B1 (en) | 1999-11-29 | 2003-02-18 | Daikin Industries, Ltd. | Process for preparing fluorine-containing halogenated hydrocarbon compound |
DE60140425D1 (de) * | 2000-02-02 | 2009-12-24 | Daikin Ind Ltd | Produktionsverfahren von fluorkohlenwasserstoffen |
US6313359B1 (en) | 2000-07-17 | 2001-11-06 | Honeywell International Inc. | Method of making hydrofluorocarbons |
US6475971B2 (en) | 2001-01-24 | 2002-11-05 | Honeywell International Inc. | Azeotrope-like composition of 1,2-dichloro-3,3,3-trifluoropropene and hydrogen fluoride composition |
US6500795B2 (en) * | 2001-01-24 | 2002-12-31 | Honeywell International Inc. | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
US6534467B2 (en) | 2001-01-24 | 2003-03-18 | Honeywell International Inc. | Azeotrope-like composition of 1,2,2-trichloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
US6451867B1 (en) * | 2001-03-21 | 2002-09-17 | Honeywell International Inc. | Mixtures containing 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3-pentafluorobutane |
US6524496B2 (en) | 2001-03-21 | 2003-02-25 | Honeywell International Inc. | Azeotrope-like composition of 1,1,1,3,3-pentafluoropropane and 1-chloro-1,1,3,3,3-pentafluoropropane |
US20050096246A1 (en) * | 2003-11-04 | 2005-05-05 | Johnson Robert C. | Solvent compositions containing chlorofluoroolefins |
CN101462924A (zh) * | 2001-06-01 | 2009-06-24 | 霍尼韦尔国际公司 | 1,1,1,3,3-五氟丁烷与氟化氢的共沸混合物的应用 |
US6500995B1 (en) | 2001-06-14 | 2002-12-31 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3,-pentachloropropane |
US20090253820A1 (en) * | 2006-03-21 | 2009-10-08 | Honeywell International Inc. | Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming |
US20040089839A1 (en) | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
US7230146B2 (en) | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
US8033120B2 (en) * | 2002-10-25 | 2011-10-11 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
US9796848B2 (en) * | 2002-10-25 | 2017-10-24 | Honeywell International Inc. | Foaming agents and compositions containing fluorine substituted olefins and methods of foaming |
US7279451B2 (en) | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
US7102040B2 (en) * | 2003-04-04 | 2006-09-05 | Honeywell International Inc. | Fluoropolymer lined metallic vessel design |
US6759381B1 (en) | 2003-05-06 | 2004-07-06 | Honeywell International Inc. | Azeotrope-like compositions of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene |
US7214839B2 (en) * | 2003-05-23 | 2007-05-08 | Honeywell International Inc. | Method of making hydrofluorocarbons |
US7880040B2 (en) | 2004-04-29 | 2011-02-01 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US9255046B2 (en) | 2003-07-25 | 2016-02-09 | Honeywell International Inc. | Manufacturing process for HFO-1234ze |
US6844475B1 (en) | 2003-08-08 | 2005-01-18 | Honeywell International Business Machines | Low temperature production of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) |
US7655610B2 (en) * | 2004-04-29 | 2010-02-02 | Honeywell International Inc. | Blowing agent compositions comprising fluorinated olefins and carbon dioxide |
US9308199B2 (en) | 2004-04-29 | 2016-04-12 | Honeywell International Inc. | Medicament formulations |
US9499729B2 (en) | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
WO2005108334A1 (en) | 2004-04-29 | 2005-11-17 | Honeywell International, Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene |
US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
US8383867B2 (en) | 2004-04-29 | 2013-02-26 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US9024092B2 (en) | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US7951982B2 (en) | 2004-04-29 | 2011-05-31 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US9102579B2 (en) | 2004-04-29 | 2015-08-11 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US7659434B2 (en) | 2004-04-29 | 2010-02-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
US7026521B1 (en) * | 2005-03-28 | 2006-04-11 | Honeywell International Inc. | Methane and methyl chloride as selective reducing agent in the transformation of hydrochlorofluorocarbons or chlorofluorocarbons to hydrofluorocarbons |
US8574451B2 (en) * | 2005-06-24 | 2013-11-05 | Honeywell International Inc. | Trans-chloro-3,3,3-trifluoropropene for use in chiller applications |
US8420706B2 (en) * | 2005-06-24 | 2013-04-16 | Honeywell International Inc. | Foaming agents, foamable compositions, foams and articles containing halogen substituted olefins, and methods of making same |
CN1911512B (zh) * | 2005-07-07 | 2011-12-07 | 独立行政法人产业技术综合研究所 | 氟化催化剂及其制备方法、以及使用了该催化剂的氟化合物的制备方法 |
US20070118003A1 (en) * | 2005-11-21 | 2007-05-24 | Honeywell International Inc. | Method for preparing 1,1,1,3,3-pentafluoropropane |
US9000061B2 (en) | 2006-03-21 | 2015-04-07 | Honeywell International Inc. | Foams and articles made from foams containing 1-chloro-3,3,3-trifluoropropene (HFCO-1233zd) |
EP2059729A2 (en) * | 2006-06-28 | 2009-05-20 | Honeywell International Inc. | Thermal insulation foam |
WO2009079062A2 (en) * | 2007-09-27 | 2009-06-25 | Honeywell International Inc. | Field installation of a vehicle protection system |
US20100016457A1 (en) * | 2008-07-16 | 2010-01-21 | Bowman James M | Hfo-1234ze mixed isomers with hfc-245fa as a blowing agent, aerosol, and solvent |
US8217208B2 (en) | 2008-12-12 | 2012-07-10 | Honeywell International, Inc. | Isomerization of 1-chloro-3,3,3-trifluoropropene |
CN101560138B (zh) * | 2009-05-21 | 2010-11-03 | 常熟三爱富氟化工有限责任公司 | 五氟丙烷的制备方法 |
CN107022343A (zh) | 2009-09-09 | 2017-08-08 | 霍尼韦尔国际公司 | 单氯三氟丙烯化合物和使用其的组合物和方法 |
US9334207B2 (en) | 2010-09-03 | 2016-05-10 | Honeywell International Inc. | Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane |
CN102211974B (zh) * | 2011-04-08 | 2013-06-05 | 北京宇极科技发展有限公司 | 一种1,3,3,3-四氟丙烯的制备方法 |
ES2625204T3 (es) | 2012-01-25 | 2017-07-18 | Daikin Industries, Ltd. | Procedimiento para producir una olefina que contiene flúor |
US8889924B2 (en) * | 2012-02-14 | 2014-11-18 | Honeywell International Inc. | Process for the production of 1,3,3,3-tetrafluoropropene |
US8519200B1 (en) * | 2012-02-23 | 2013-08-27 | Honeywell International Inc. | Azeotropic compositions of 1,1,3,3-tetrachloro-1-fluoropropane and hydrogen fluoride |
US9938212B2 (en) | 2012-03-28 | 2018-04-10 | Honeywell International Inc. | Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane |
US9162947B2 (en) | 2013-03-15 | 2015-10-20 | Honeywell International Inc. | High temperature isomerization of (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene |
CN103626625B (zh) * | 2013-08-29 | 2015-09-23 | 巨化集团技术中心 | 一种1,1,1,3,3-五氟丙烷的制备方法 |
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 |
CN112739672A (zh) | 2018-08-24 | 2021-04-30 | 霍尼韦尔国际公司 | 用于产生三氟碘甲烷的方法 |
US10954177B2 (en) | 2018-08-24 | 2021-03-23 | Honeywell International Inc. | Processes for producing trifluoroiodomethane and trifluoroacetyl iodide |
US11554956B2 (en) | 2019-04-16 | 2023-01-17 | Honeywell International Inc. | Integrated process and catalysts for manufacturing hydrogen iodide from hydrogen and iodine |
US11274069B2 (en) | 2020-08-13 | 2022-03-15 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Mono-substituted cyclopentadienes and metal cyclopentadienyl complexes and synthesis methods thereof |
US20230234901A1 (en) * | 2022-01-26 | 2023-07-27 | Honeywell International Inc. | Preparation of an improved composition from 1-chloro-3,3,3-trifluoropropene (hfo-1233zd) high boiling residue by-product |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA684687A (en) * | 1964-04-21 | B. Smith Lee | Manufacture of halopropane | |
US2560838A (en) * | 1947-01-24 | 1951-07-17 | Arnold Robert Charles | Preparation of fluorine compounds |
US2942036A (en) * | 1957-12-13 | 1960-06-21 | Allied Chem | Manufacture of halopropane |
GB920855A (en) * | 1960-05-08 | 1963-03-13 | Aharon Katchalsky | A process for the preparation of telomers or adducts |
BE622939A (ja) * | 1961-09-28 | |||
US4078007A (en) * | 1975-10-03 | 1978-03-07 | Halocarbon Products Corporation | Fluorine substitution in 1,1,1-trihalomethanes |
US4967024A (en) * | 1988-06-23 | 1990-10-30 | E. I. Du Pont De Nemours And Company | Catalyzed hydrofluorination process |
WO1990008754A2 (en) * | 1989-02-02 | 1990-08-09 | Asahi Glass Company Ltd. | Process for producing a 2,2-difluoropropane |
US5202509A (en) * | 1989-09-01 | 1993-04-13 | Societe Atochem | Catalysts for liquid phase fluorination |
BE1005096A3 (fr) * | 1991-07-10 | 1993-04-20 | Solvay | Procede pour la preparation de 1-chloro-1,1,3,3,3-pentafluoropropane et de 1,1,1,3,3,3-hexafluoropropane. |
US5395997A (en) * | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
-
1995
- 1995-07-05 DE DE0770048T patent/DE770048T1/de active Pending
- 1995-07-05 ES ES95924777T patent/ES2104521T3/es not_active Expired - Lifetime
- 1995-07-05 DE DE69507034T patent/DE69507034C5/de not_active Expired - Lifetime
- 1995-07-05 KR KR1019970700157A patent/KR100240375B1/ko not_active IP Right Cessation
- 1995-07-05 BR BR9508233A patent/BR9508233A/pt not_active Application Discontinuation
- 1995-07-05 DK DK95924777T patent/DK0770048T3/da active
- 1995-07-05 JP JP8504369A patent/JP2818035B2/ja not_active Expired - Lifetime
- 1995-07-05 HU HU9700083A patent/HUT75954A/hu unknown
- 1995-07-05 AT AT95924777T patent/ATE175180T1/de active
- 1995-07-05 EP EP95924777A patent/EP0770048B1/en not_active Expired - Lifetime
- 1995-07-05 CZ CZ9771A patent/CZ7197A3/cs unknown
- 1995-07-05 WO PCT/US1995/008404 patent/WO1996001797A1/en not_active Application Discontinuation
- 1995-07-05 CN CN95194097A patent/CN1063736C/zh not_active Expired - Lifetime
- 1995-07-05 AU AU29160/95A patent/AU688925B2/en not_active Expired
- 1995-08-25 US US08/519,857 patent/US5574192A/en not_active Expired - Lifetime
-
1997
- 1997-09-30 GR GR970300031T patent/GR970300031T1/el unknown
-
1999
- 1999-03-26 GR GR990400899T patent/GR3029809T3/el unknown
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009084290A (ja) * | 1995-10-23 | 2009-04-23 | Solvay (Sa) | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
JP2002504528A (ja) * | 1998-02-26 | 2002-02-12 | ソルヴェイ | クロロ炭化水素のフッ化水素化方法 |
WO2000017136A1 (fr) * | 1998-09-22 | 2000-03-30 | Daikin Industries, Ltd. | Production de 1,1,1,3,3-pentafluoro-propane et/ou de 1-chloro-3,3,3-trifluoropropene |
JP2004500339A (ja) | 1999-10-06 | 2004-01-08 | ソルヴェイ | ハロゲン化炭化水素の製造方法 |
JP2007535570A (ja) * | 2004-04-29 | 2007-12-06 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3,3,3−テトラフルオロプロペンの合成方法 |
JP2011236228A (ja) * | 2004-04-29 | 2011-11-24 | Honeywell Internatl Inc | 1,3,3,3−テトラフルオロプロペンの合成方法 |
JP2021073172A (ja) * | 2013-03-13 | 2021-05-13 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 1,3,3−トリクロロ−1,1−ジフルオロプロパンおよびフッ化水素の共沸組成物 |
JP2018515522A (ja) * | 2015-05-12 | 2018-06-14 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | HCFO−1233zd及びHFC−245faを製造するための統合方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100240375B1 (ko) | 2000-01-15 |
DE69507034D1 (de) | 1999-02-11 |
CZ7197A3 (cs) | 1998-02-18 |
EP0770048B1 (en) | 1998-12-30 |
DE69507034T2 (de) | 1999-07-01 |
AU2916095A (en) | 1996-02-09 |
ES2104521T3 (es) | 1999-05-01 |
US5574192A (en) | 1996-11-12 |
WO1996001797A1 (en) | 1996-01-25 |
KR970704649A (ko) | 1997-09-06 |
ATE175180T1 (de) | 1999-01-15 |
DE770048T1 (de) | 1998-01-02 |
HUT75954A (en) | 1997-05-28 |
CN1063736C (zh) | 2001-03-28 |
GR970300031T1 (en) | 1997-09-30 |
AU688925B2 (en) | 1998-03-19 |
DE69507034C5 (de) | 2009-04-30 |
ES2104521T1 (es) | 1997-10-16 |
DK0770048T3 (da) | 1999-08-30 |
BR9508233A (pt) | 1998-05-19 |
CN1152904A (zh) | 1997-06-25 |
GR3029809T3 (en) | 1999-06-30 |
EP0770048A1 (en) | 1997-05-02 |
JP2818035B2 (ja) | 1998-10-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2818035B2 (ja) | 1,1,1,3,3−ペンタフルオロプロパンの製造法 | |
US6187976B1 (en) | Process for the preparation of fluorine containing hydrohalocarbons | |
EP0759895B1 (en) | Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin | |
JP3389251B2 (ja) | ハイドロクロロカーボン及びハイドロクロロフルオロカーボンの液相接触フッ素化 | |
EP0931043B1 (en) | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene | |
KR101282754B1 (ko) | 1,1,1-트리플루오로-2,3-디클로로프로판 제조방법 | |
EP0717728B1 (en) | Process for the preparation of 1,1,1,3,3-pentafluoropropane | |
US7880040B2 (en) | Method for producing fluorinated organic compounds | |
WO1995004021A1 (en) | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms | |
US5254771A (en) | Process for the preparation of 1,1,1-trifluoro-2-2-dichloroethane under elevated pressure | |
US8053613B2 (en) | Processes for producing 1,2,3,3,3-pentafluoropropene and precursors thereof | |
JP2846713B2 (ja) | 高められた圧力の下に1,1,1‐トリフルオロ‐2,2‐ジクロロエタンを製造する方法 | |
EP0958266B1 (en) | Process for the manufacture of halocarbons | |
CA2192843C (en) | Process for the manufacture of 1,1,1,3,3-pentafluoropropane | |
WO1998040335A1 (fr) | Procede pour produire du 1,1,1,3,3-pentafluoropropane | |
MXPA96006750A (en) | Process for the manufacture of 1,1,1,3,3-pentafluoroprop |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S202 | Request for registration of non-exclusive licence |
Free format text: JAPANESE INTERMEDIATE CODE: R315201 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20070821 Year of fee payment: 9 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080821 Year of fee payment: 10 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080821 Year of fee payment: 10 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090821 Year of fee payment: 11 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090821 Year of fee payment: 11 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100821 Year of fee payment: 12 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110821 Year of fee payment: 13 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110821 Year of fee payment: 13 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120821 Year of fee payment: 14 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120821 Year of fee payment: 14 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130821 Year of fee payment: 15 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |