DE2215019A1 - Verfahren zur Herstellung von 1,1-Difluoräthan - Google Patents
Verfahren zur Herstellung von 1,1-DifluoräthanInfo
- Publication number
- DE2215019A1 DE2215019A1 DE19722215019 DE2215019A DE2215019A1 DE 2215019 A1 DE2215019 A1 DE 2215019A1 DE 19722215019 DE19722215019 DE 19722215019 DE 2215019 A DE2215019 A DE 2215019A DE 2215019 A1 DE2215019 A1 DE 2215019A1
- Authority
- DE
- Germany
- Prior art keywords
- vanadium
- vinyl chloride
- activated carbon
- difluoroethane
- hydrogen fluoride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000003681 vanadium Chemical class 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000003682 vanadium compounds Chemical class 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 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
- 239000004927 clay Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- YACLCMMBHTUQON-UHFFFAOYSA-N 1-chloro-1-fluoroethane Chemical compound CC(F)Cl YACLCMMBHTUQON-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 101100492752 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) apg-3 gene Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910021550 Vanadium Chloride Inorganic materials 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE102762 | 1971-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2215019A1 true DE2215019A1 (de) | 1972-11-02 |
Family
ID=3841510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722215019 Pending DE2215019A1 (de) | 1971-04-28 | 1972-03-28 | Verfahren zur Herstellung von 1,1-Difluoräthan |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3862995A (enExample) |
| BE (1) | BE766395A (enExample) |
| DE (1) | DE2215019A1 (enExample) |
| ES (1) | ES401416A1 (enExample) |
| FR (1) | FR2134381B1 (enExample) |
| GB (1) | GB1343001A (enExample) |
| IT (1) | IT954827B (enExample) |
| NL (1) | NL7204766A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600536A1 (fr) * | 1992-12-02 | 1994-06-08 | SOLVAY (Société Anonyme) | Procédé de purification de 1,1-difluoroéthane |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258225A (en) * | 1977-08-15 | 1981-03-24 | E. I. Du Pont De Nemours And Company | TaF5 and NbF5 as fluorination catalysts |
| US4147733A (en) * | 1978-05-22 | 1979-04-03 | The Dow Chemical Company | Fluorination of chlorinated hydrocarbons |
| USD294267S (en) | 1985-04-19 | 1988-02-16 | International Tool And Supply Company, Inc. | Trash compactor |
| US4818513A (en) * | 1987-12-21 | 1989-04-04 | Ppg Industries, Inc. | Separation of hydrogen fluoride from 1,1-difluoroethene |
| US4827055A (en) * | 1988-03-07 | 1989-05-02 | Pennwalt Corporation | Process for preparing vinylidene fluoride by the direct fluorination of vinylidene chloride |
| US4937398A (en) * | 1988-12-27 | 1990-06-26 | Allied-Signal Inc. | Process for the preparation of fluorinated alkanes from alkenes |
| ES2132065T3 (es) * | 1989-11-06 | 1999-08-16 | Rhodia Chimie Sa | Procedimiento de preparacion de derivados aromaticos fluorados y catalizadores a base de acido de lewis. |
| US4988434A (en) * | 1989-12-13 | 1991-01-29 | Exxon Research And Engineering Company | Removal of metallic contaminants from a hydrocarbonaceous liquid |
| GB9105166D0 (en) * | 1991-03-12 | 1991-04-24 | Ici Plc | Chemical process |
| GB9105167D0 (en) * | 1991-03-12 | 1991-04-24 | Ici Plc | Chemical process |
| FR2713634B1 (fr) * | 1993-12-09 | 1996-01-19 | Atochem Elf Sa | Fluoration catalytique d'hydrocarbures halogènes en phase gazeuse. |
| US5789633A (en) * | 1995-06-06 | 1998-08-04 | E. I. Du Pont De Nemours And Company | Azeotropic or azeotrope-like compositions of hydrofluoric acid with dihaloethanes |
| US5714650A (en) * | 1995-06-07 | 1998-02-03 | E. I. Du Pont De Nemours And Company | Continuous manufacture of 1,1-difluoroethane |
| US5672788A (en) * | 1995-06-07 | 1997-09-30 | E. I. Du Pont De Nemours And Company | Two-step process for manufacturing 1,1-difluoroethane |
| US5763708A (en) * | 1995-09-20 | 1998-06-09 | Allied Signal Inc. | Process for the production of difluoromethane |
| US5866729A (en) * | 1997-01-02 | 1999-02-02 | E. I. Du Pont De Nemours And Company | Manufacture of 1, 1-difluoroethane |
| US5777185A (en) * | 1997-09-09 | 1998-07-07 | Laroche Industries Inc. | Production of organic fluorine compounds |
| FR2771737B1 (fr) | 1997-12-01 | 2000-02-04 | Solvay | Procedes de production et d'epuration de 1,1-difluoroethane et produit ainsi obtenu |
| KR100383216B1 (ko) * | 2000-12-08 | 2003-05-12 | 한국과학기술연구원 | 1,1-디플루오로에탄 제조용 촉매 및 1,1-디플루오로에탄제조방법 |
| US7696392B2 (en) * | 2003-11-10 | 2010-04-13 | Showa Denko K.K. | Purification method of 1,1-difluoroethane |
| US7112708B2 (en) * | 2004-04-01 | 2006-09-26 | Honeywell International Inc. | Method of making difluoromethane, 1,1,1-trifluoroethane and 1,1-difluoroethane |
| GB202100874D0 (en) * | 2021-01-22 | 2021-03-10 | Mexichem Fluor Sa De Cv | Process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1996115A (en) * | 1931-05-29 | 1935-04-02 | Du Pont | Alkyl halide synthesis |
| US2005707A (en) * | 1932-08-31 | 1935-06-18 | Kinetic Chemicals Inc | Production of organic fluorine compounds |
| GB823519A (en) * | 1957-09-25 | 1959-11-11 | Dow Corning | A process for the preparation of fluorinated olefins |
-
1971
- 1971-04-28 BE BE766395A patent/BE766395A/xx unknown
-
1972
- 1972-03-28 DE DE19722215019 patent/DE2215019A1/de active Pending
- 1972-03-30 IT IT22640/72A patent/IT954827B/it active
- 1972-04-03 ES ES401416A patent/ES401416A1/es not_active Expired
- 1972-04-10 NL NL7204766A patent/NL7204766A/xx not_active Application Discontinuation
- 1972-04-10 GB GB1646572A patent/GB1343001A/en not_active Expired
- 1972-04-12 FR FR7213081A patent/FR2134381B1/fr not_active Expired
- 1972-04-18 US US245191A patent/US3862995A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600536A1 (fr) * | 1992-12-02 | 1994-06-08 | SOLVAY (Société Anonyme) | Procédé de purification de 1,1-difluoroéthane |
| BE1006432A3 (fr) * | 1992-12-02 | 1994-08-23 | Solvay | Procede de purification de 1,1-difluoroethane. |
| US5396001A (en) * | 1992-12-02 | 1995-03-07 | Solvay (Societe Anonyme) | Process for the purification of 1,1-difluoroethane |
Also Published As
| Publication number | Publication date |
|---|---|
| BE766395A (fr) | 1971-10-28 |
| GB1343001A (en) | 1974-01-10 |
| FR2134381A1 (enExample) | 1972-12-08 |
| IT954827B (it) | 1973-09-15 |
| ES401416A1 (es) | 1975-02-16 |
| US3862995A (en) | 1975-01-28 |
| NL7204766A (enExample) | 1972-10-31 |
| FR2134381B1 (enExample) | 1976-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |