CZ291762B6 - Způsob výroby 1,1,1,3,3-pentafluorpropanu - Google Patents
Způsob výroby 1,1,1,3,3-pentafluorpropanu Download PDFInfo
- Publication number
- CZ291762B6 CZ291762B6 CZ19981254A CZ125498A CZ291762B6 CZ 291762 B6 CZ291762 B6 CZ 291762B6 CZ 19981254 A CZ19981254 A CZ 19981254A CZ 125498 A CZ125498 A CZ 125498A CZ 291762 B6 CZ291762 B6 CZ 291762B6
- Authority
- CZ
- Czechia
- Prior art keywords
- pentachloropropane
- catalyst
- process according
- pentafluoropropane
- carried out
- Prior art date
Links
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 claims abstract description 41
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 24
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 23
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 35
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical class Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical class ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002222 fluorine compounds Chemical class 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 abstract description 12
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 150000002739 metals Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- 238000003682 fluorination reaction Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical class CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 description 2
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 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
- XAHBEACGJQDUPF-UHFFFAOYSA-N 1,2-dichloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(Cl)C(F)(F)Cl XAHBEACGJQDUPF-UHFFFAOYSA-N 0.000 description 1
- UHMWWIKRVZTBBR-UHFFFAOYSA-N 1-chloro-1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)(F)Cl UHMWWIKRVZTBBR-UHFFFAOYSA-N 0.000 description 1
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 description 1
- YGFIGGVCQHKDOL-UHFFFAOYSA-N 2,3-dichloro-1,1,1,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(Cl)C(F)(F)F YGFIGGVCQHKDOL-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- C07C17/26—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9512558A FR2740132B1 (fr) | 1995-10-23 | 1995-10-23 | Procede pour la preparation de 1,1,1,3,3-pentafluoropropane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ125498A3 CZ125498A3 (cs) | 1998-07-15 |
| CZ291762B6 true CZ291762B6 (cs) | 2003-05-14 |
Family
ID=9483881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19981254A CZ291762B6 (cs) | 1995-10-23 | 1996-10-04 | Způsob výroby 1,1,1,3,3-pentafluorpropanu |
Country Status (28)
| Country | Link |
|---|---|
| US (3) | US6730817B1 (https=) |
| EP (1) | EP0858440B1 (https=) |
| JP (3) | JP2000513705A (https=) |
| KR (1) | KR19990066942A (https=) |
| CN (1) | CN1079787C (https=) |
| AR (1) | AR004079A1 (https=) |
| AT (1) | ATE211723T1 (https=) |
| AU (1) | AU722645B2 (https=) |
| BR (1) | BR9611223A (https=) |
| CA (1) | CA2232421C (https=) |
| CZ (1) | CZ291762B6 (https=) |
| DE (1) | DE69618476T2 (https=) |
| DK (1) | DK0858440T3 (https=) |
| EA (1) | EA001416B1 (https=) |
| ES (1) | ES2171228T3 (https=) |
| FR (1) | FR2740132B1 (https=) |
| HU (1) | HU222560B1 (https=) |
| IL (1) | IL124086A (https=) |
| MX (1) | MX9803175A (https=) |
| NO (1) | NO309716B1 (https=) |
| NZ (1) | NZ320161A (https=) |
| PL (1) | PL186534B1 (https=) |
| PT (1) | PT858440E (https=) |
| RO (1) | RO120193B1 (https=) |
| SK (1) | SK282636B6 (https=) |
| UA (1) | UA61895C2 (https=) |
| WO (1) | WO1997015540A1 (https=) |
| ZA (1) | ZA968481B (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2740132B1 (fr) * | 1995-10-23 | 1997-12-19 | Solvay | Procede pour la preparation de 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 |
| US6023004A (en) * | 1996-11-12 | 2000-02-08 | Alliedsignal, Inc. | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon |
| US6399839B1 (en) | 1997-05-05 | 2002-06-04 | Solvay (Societe Anonyme) | Method for preparing halogenated hydrocarbons |
| WO1999007659A1 (fr) | 1997-08-08 | 1999-02-18 | Solvay (Societe Anonyme) | Procede de preparation d'hydrocarbures halogenes |
| BE1011319A3 (fr) | 1997-05-05 | 1999-07-06 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| ES2218829T3 (es) * | 1997-05-05 | 2004-11-16 | Solvay (Societe Anonyme) | Procedimiento de preparacion de hidrocarburos halogenados. |
| BE1011188A3 (fr) * | 1997-06-02 | 1999-06-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| BE1011249A3 (fr) * | 1997-07-03 | 1999-06-01 | Solvay | Pentachlorobutane, son procede de fabrication et son utilisation, procede de preparation du 1,1-difluoro-2-trifluoromethylpropane et utilisation de ce compose. |
| FR2768727A1 (fr) * | 1997-09-23 | 1999-03-26 | Atochem Elf Sa | Synthese du 1,1,1,3,3-pentafluoropropane |
| FR2768726A1 (fr) * | 1997-09-23 | 1999-03-26 | Atochem Elf Sa | Synthese du 1, 1, 1, 3, 3-pentafluoropropane |
| 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 |
| BE1012268A3 (fr) | 1998-11-05 | 2000-08-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| CA2355385C (fr) | 1998-12-18 | 2010-04-27 | Solvay (Societe Anonyme) | Procede de separation d'un melange comprenant au moins un hydrofluoroalcane et du fluorure d'hydrogene, procedes de preparation d'un hydrofluoroalcane et compositions azeotropiques |
| WO2001025175A1 (fr) | 1999-10-06 | 2001-04-12 | Solvay (Societe Anonyme) | Procede de preparation d'hydrocarbures halogenes en presence d'un cocatalyseur |
| WO2002098529A1 (en) | 2001-06-01 | 2002-12-12 | Honeywell International, Inc. | Azeotrope-like compositions of 1,1,1,3,3-pentafluorobutane and hydrogen fluoride |
| US6500995B1 (en) | 2001-06-14 | 2002-12-31 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3,-pentachloropropane |
| JP4165399B2 (ja) * | 2001-10-24 | 2008-10-15 | ダイキン工業株式会社 | 触媒回収方法および触媒回収システム、ならびにパーフルオロアルキルアイオダイドテロマーの製造方法および製造装置 |
| US7214839B2 (en) * | 2003-05-23 | 2007-05-08 | Honeywell International Inc. | Method of making hydrofluorocarbons |
| US7371363B2 (en) * | 2003-07-15 | 2008-05-13 | Honeywell International Inc. | Methods of purifying hydrogen fluoride |
| US8645709B2 (en) * | 2006-11-14 | 2014-02-04 | Cfph, Llc | Biometric access data encryption |
| CN102227395A (zh) * | 2008-11-13 | 2011-10-26 | 苏威氟有限公司 | 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法 |
| WO2010060868A1 (en) * | 2008-11-25 | 2010-06-03 | Solvay Fluor Gmbh | Process for the preparation of chlorofluoroalkenes |
| CN102491871B (zh) * | 2011-12-12 | 2013-12-18 | 南京信息工程大学 | 一种七氟丙烷的制备方法 |
| US9353029B2 (en) | 2013-03-14 | 2016-05-31 | Honeywell International, Inc. | Fluorination process and reactor |
| CN104230649A (zh) * | 2013-06-18 | 2014-12-24 | 林卫荃 | 五氯丙烷制备方法 |
| CA2940149C (en) * | 2014-02-19 | 2022-06-21 | Arkema Inc. | Process for the manufacture of hydrochlorofluoroolefins |
| US10337205B2 (en) | 2017-06-22 | 2019-07-02 | Erick Westfahl | Portable fence system |
| CN117886665B (zh) * | 2023-12-11 | 2025-06-10 | 江西中欣埃克盛新材料有限公司 | 合成1,1,1,3,3-五氟丙烷的全流程连续工艺 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862978A (en) * | 1967-08-24 | 1975-01-28 | Dow Chemical Co | Catalytic synthesis of organic halogen compounds from an ethylenically unsaturated compound and a halogenated organic compound |
| 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. |
| DE4305164A1 (de) | 1993-02-19 | 1994-08-25 | Bayer Ag | Verfahren zur Herstellung von 1,1,1,3,3-Pentafluorpropan |
| CN1128016A (zh) | 1993-07-29 | 1996-07-31 | 联合讯号公司 | 1，1，1，3，3-五氟丙烷的制备方法 |
| US5395997A (en) * | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
| CA2167698A1 (en) | 1993-08-16 | 1995-02-23 | Russell Ward Johnson | Process for combining chlorine-containing molecules to synthesize fluorine-containing products |
| KR100240375B1 (ko) * | 1994-07-11 | 2000-01-15 | 크리스 로저 에이치 | 1,1,1,3,3-펜타플루오로프로판의 제조방법 |
| FR2724928B1 (fr) * | 1994-09-26 | 1996-10-31 | Atochem Elf Sa | Synthese de 1,1,1,3,3-pentafluoropropane |
| JPH08239334A (ja) * | 1995-03-03 | 1996-09-17 | Central Glass Co Ltd | 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 |
| 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 |
| FR2740132B1 (fr) * | 1995-10-23 | 1997-12-19 | Solvay | Procede pour la preparation de 1,1,1,3,3-pentafluoropropane |
| JPH09268141A (ja) * | 1996-04-03 | 1997-10-14 | Central Glass Co Ltd | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| JP3831987B2 (ja) * | 1996-09-25 | 2006-10-11 | 旭硝子株式会社 | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| JPH10101594A (ja) * | 1996-09-25 | 1998-04-21 | Asahi Glass Co Ltd | １，１，１，３，３−ペンタフルオロプロパンの製造法 |
-
1995
- 1995-10-23 FR FR9512558A patent/FR2740132B1/fr not_active Expired - Lifetime
-
1996
- 1996-04-10 UA UA98042033A patent/UA61895C2/uk unknown
- 1996-10-04 CZ CZ19981254A patent/CZ291762B6/cs not_active IP Right Cessation
- 1996-10-04 NZ NZ320161A patent/NZ320161A/xx not_active IP Right Cessation
- 1996-10-04 ES ES96934532T patent/ES2171228T3/es not_active Expired - Lifetime
- 1996-10-04 IL IL12408696A patent/IL124086A/xx not_active IP Right Cessation
- 1996-10-04 JP JP09516231A patent/JP2000513705A/ja active Pending
- 1996-10-04 SK SK489-98A patent/SK282636B6/sk not_active IP Right Cessation
- 1996-10-04 PT PT96934532T patent/PT858440E/pt unknown
- 1996-10-04 DE DE69618476T patent/DE69618476T2/de not_active Expired - Lifetime
- 1996-10-04 DK DK96934532T patent/DK0858440T3/da active
- 1996-10-04 HU HU9802978A patent/HU222560B1/hu active IP Right Grant
- 1996-10-04 WO PCT/EP1996/004315 patent/WO1997015540A1/fr not_active Ceased
- 1996-10-04 CA CA002232421A patent/CA2232421C/fr not_active Expired - Lifetime
- 1996-10-04 BR BR9611223A patent/BR9611223A/pt not_active IP Right Cessation
- 1996-10-04 US US09/051,746 patent/US6730817B1/en not_active Expired - Fee Related
- 1996-10-04 CN CN96199236A patent/CN1079787C/zh not_active Expired - Lifetime
- 1996-10-04 EP EP96934532A patent/EP0858440B1/fr not_active Expired - Lifetime
- 1996-10-04 EA EA199800322A patent/EA001416B1/ru not_active IP Right Cessation
- 1996-10-04 AU AU72849/96A patent/AU722645B2/en not_active Expired
- 1996-10-04 PL PL96326367A patent/PL186534B1/pl unknown
- 1996-10-04 AT AT96934532T patent/ATE211723T1/de active
- 1996-10-04 KR KR1019980702865A patent/KR19990066942A/ko not_active Ceased
- 1996-10-04 RO RO98-00880A patent/RO120193B1/ro unknown
- 1996-10-08 ZA ZA968481A patent/ZA968481B/xx unknown
- 1996-10-23 AR ARP960104867A patent/AR004079A1/es active IP Right Grant
-
1998
- 1998-04-22 NO NO981800A patent/NO309716B1/no not_active IP Right Cessation
- 1998-04-23 MX MX9803175A patent/MX9803175A/es unknown
-
2003
- 2003-07-03 US US10/613,546 patent/US6930215B2/en not_active Expired - Fee Related
-
2005
- 2005-07-19 US US11/184,353 patent/US20050256348A1/en not_active Abandoned
-
2007
- 2007-06-12 JP JP2007154930A patent/JP2007262084A/ja active Pending
-
2008
- 2008-11-13 JP JP2008291297A patent/JP2009084290A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ291762B6 (cs) | Způsob výroby 1,1,1,3,3-pentafluorpropanu | |
| US9120716B2 (en) | Process for the preparation of 2,3,3,3 tetrafluoropropene | |
| KR101354492B1 (ko) | 플루오르화 유기 화합물 제조 방법 | |
| US6362383B1 (en) | Hydro-fluorination of chlorinated hydrocarbons | |
| US5969198A (en) | Process for the preparation of 1,1,1,3,3-pentafluoropropane | |
| EP0770048A1 (en) | Process for the manufacture of 1,1,1,3,3-pentafluoropropane | |
| JP2001503771A (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 | |
| KR100363940B1 (ko) | 클로로(플루오로)부탄의하이드로플루오르화방법 | |
| US7947856B2 (en) | Process for the preparation of halogenated hydrocarbons with at least 3 carbon atoms in the presence of iron and a phosphite | |
| JP2014503496A (ja) | ペンタクロロプロパンの液相フッ素化による２−クロロ−３，３，３−トリフルオロプロペン（ｈｃｆｏ１２３３ｘｆ）の製造方法 | |
| GB2329386A (en) | Synthesis of 1,1,1,3,3-Pentafluoropropane | |
| JP3130656B2 (ja) | １，１−ジクロロ−１，３，３，３− テトラフルオロプロパンの製造法 | |
| US7629496B2 (en) | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MC4A | Patent revocation (annulment) |
Effective date: 20061110 |