DE2139993C3 - Verfahren zur Herstellung von 1,1-Dlfluoräthan - Google Patents
Verfahren zur Herstellung von 1,1-DlfluoräthanInfo
- Publication number
- DE2139993C3 DE2139993C3 DE2139993A DE2139993A DE2139993C3 DE 2139993 C3 DE2139993 C3 DE 2139993C3 DE 2139993 A DE2139993 A DE 2139993A DE 2139993 A DE2139993 A DE 2139993A DE 2139993 C3 DE2139993 C3 DE 2139993C3
- Authority
- DE
- Germany
- Prior art keywords
- acetylene
- hydrogen fluoride
- acid
- reaction
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 17
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 17
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 13
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 11
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 9
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 3
- 230000002028 premature Effects 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 18
- -1 ammonium radical Chemical class 0.000 description 12
- 239000007789 gas Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- REOXYQKMUAXKKS-UHFFFAOYSA-N OS(=O)(=O)C(F)=C(F)C(F)(F)C(F)(F)F Chemical compound OS(=O)(=O)C(F)=C(F)C(F)(F)C(F)(F)F REOXYQKMUAXKKS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- QNDPUZFBWUBSNH-UHFFFAOYSA-I magic acid Chemical compound OS(F)(=O)=O.F[Sb](F)(F)(F)F QNDPUZFBWUBSNH-UHFFFAOYSA-I 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787410D BE787410A (fr) | 1971-08-10 | Procede de preparation du 1,1-difluorethane | |
| DE2139993A DE2139993C3 (de) | 1971-08-10 | 1971-08-10 | Verfahren zur Herstellung von 1,1-Dlfluoräthan |
| US00273654A US3810948A (en) | 1971-08-10 | 1972-07-20 | Catalytic production of 1,1-difluoroethane |
| IT52048/72A IT961909B (it) | 1971-08-10 | 1972-08-08 | Procedimento per produrre i i difluoroetano |
| CA148,872A CA989873A (en) | 1971-08-10 | 1972-08-08 | Catalytic production of 1,1-difluoroethane |
| NL7210849A NL7210849A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-10 | 1972-08-08 | |
| JP47079205A JPS4826709A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-10 | 1972-08-09 | |
| FR7228938A FR2148604B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-10 | 1972-08-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2139993A DE2139993C3 (de) | 1971-08-10 | 1971-08-10 | Verfahren zur Herstellung von 1,1-Dlfluoräthan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2139993A1 DE2139993A1 (de) | 1973-02-22 |
| DE2139993B2 DE2139993B2 (de) | 1974-06-06 |
| DE2139993C3 true DE2139993C3 (de) | 1975-01-30 |
Family
ID=5816330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2139993A Expired DE2139993C3 (de) | 1971-08-10 | 1971-08-10 | Verfahren zur Herstellung von 1,1-Dlfluoräthan |
Country Status (8)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547182A1 (de) * | 1975-10-22 | 1977-05-05 | Dynamit Nobel Ag | Verfahren zur herstellung von 1,1-difluoraethan |
| DE4105832A1 (de) * | 1990-04-12 | 1991-10-17 | Kali Chemie Ag | Verfahren zur herstellung von fluor enthaltenden ethanderivaten |
| US5214223A (en) * | 1990-04-12 | 1993-05-25 | Kali-Chemie Ag | Method of preparing fluorine-containing ethane derivatives |
| DE4130696A1 (de) * | 1991-09-14 | 1993-03-18 | Solvay Fluor & Derivate | Verfahren zur herstellung von fluor enthaltenden ethanderivaten |
| DE4133247A1 (de) * | 1991-10-08 | 1993-04-29 | Solvay Fluor & Derivate | Verfahren zur herstellung von 1.1.1.2-tetrafluorethan |
| CN101412654B (zh) * | 2008-07-21 | 2011-12-28 | 浙江衢化氟化学有限公司 | 一种1,1-二氟乙烷的制备方法及氟化催化剂 |
-
0
- BE BE787410D patent/BE787410A/xx unknown
-
1971
- 1971-08-10 DE DE2139993A patent/DE2139993C3/de not_active Expired
-
1972
- 1972-07-20 US US00273654A patent/US3810948A/en not_active Expired - Lifetime
- 1972-08-08 IT IT52048/72A patent/IT961909B/it active
- 1972-08-08 CA CA148,872A patent/CA989873A/en not_active Expired
- 1972-08-08 NL NL7210849A patent/NL7210849A/xx not_active Application Discontinuation
- 1972-08-09 JP JP47079205A patent/JPS4826709A/ja active Pending
- 1972-08-10 FR FR7228938A patent/FR2148604B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT961909B (it) | 1973-12-10 |
| FR2148604A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-03-23 |
| JPS4826709A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-04-09 |
| NL7210849A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-13 |
| DE2139993B2 (de) | 1974-06-06 |
| BE787410A (fr) | 1973-02-12 |
| CA989873A (en) | 1976-05-25 |
| FR2148604B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-26 |
| DE2139993A1 (de) | 1973-02-22 |
| US3810948A (en) | 1974-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |