DE1917630C3 - Verfahren zur Herstellung von fluorhaltigen Perhalogencarbonsäurefluoriden oder -Chloriden - Google Patents
Verfahren zur Herstellung von fluorhaltigen Perhalogencarbonsäurefluoriden oder -ChloridenInfo
- Publication number
- DE1917630C3 DE1917630C3 DE1917630A DE1917630A DE1917630C3 DE 1917630 C3 DE1917630 C3 DE 1917630C3 DE 1917630 A DE1917630 A DE 1917630A DE 1917630 A DE1917630 A DE 1917630A DE 1917630 C3 DE1917630 C3 DE 1917630C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- perhalocarboxylic
- mol
- fluorine
- acid
- 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
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 16
- 229910052731 fluorine Inorganic materials 0.000 title claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 8
- 239000011737 fluorine Substances 0.000 title claims description 8
- 150000002222 fluorine compounds Chemical class 0.000 title claims description 5
- 150000001805 chlorine compounds Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical class [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003797 solvolysis reaction Methods 0.000 description 5
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 5
- 125000006414 CCl Chemical group ClC* 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- -1 Hg 2 SO 4 Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- NNTJKSMVNWGFTB-UHFFFAOYSA-N disulfuryl chloride Chemical compound ClS(=O)(=O)OS(Cl)(=O)=O NNTJKSMVNWGFTB-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical compound FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1917630A DE1917630C3 (de) | 1969-04-05 | 1969-04-05 | Verfahren zur Herstellung von fluorhaltigen Perhalogencarbonsäurefluoriden oder -Chloriden |
| GB02881/70A GB1248175A (en) | 1969-04-05 | 1970-03-17 | Process for the production of perhalocarboxylic acid fluorides or chlorides containing fluorine |
| NL7003847A NL7003847A (enExample) | 1969-04-05 | 1970-03-18 | |
| FR7010216A FR2038257B1 (enExample) | 1969-04-05 | 1970-03-20 | |
| US00031048A US3725475A (en) | 1969-04-05 | 1970-04-06 | Process of preparing fluorine containing perhalogencarboxylic acid fluorides or chlorides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1917630A DE1917630C3 (de) | 1969-04-05 | 1969-04-05 | Verfahren zur Herstellung von fluorhaltigen Perhalogencarbonsäurefluoriden oder -Chloriden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1917630A1 DE1917630A1 (de) | 1970-10-15 |
| DE1917630C3 true DE1917630C3 (de) | 1979-04-12 |
Family
ID=5730468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1917630A Expired DE1917630C3 (de) | 1969-04-05 | 1969-04-05 | Verfahren zur Herstellung von fluorhaltigen Perhalogencarbonsäurefluoriden oder -Chloriden |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3725475A (enExample) |
| DE (1) | DE1917630C3 (enExample) |
| FR (1) | FR2038257B1 (enExample) |
| GB (1) | GB1248175A (enExample) |
| NL (1) | NL7003847A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2261108C3 (de) * | 1972-12-14 | 1975-12-04 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung fluorhaltiger Carbonyldihalogenide |
| JPS55164644A (en) * | 1979-06-12 | 1980-12-22 | Asahi Glass Co Ltd | Preparation of difluoroiodoacetylfluoride |
| JPS6056126B2 (ja) * | 1980-08-26 | 1985-12-09 | 旭硝子株式会社 | ジフルオロハロアセチルフルオリドの製造方法 |
| US4411843A (en) * | 1980-12-15 | 1983-10-25 | Allied Corporation | Conversion of 1,1,1-trichloroperhaloalkanes into perhaloalkanoyl chlorides |
| US4374782A (en) * | 1981-06-18 | 1983-02-22 | Allied Corporation | Synthesis of trifluoroacetyl fluoride |
| US4382897A (en) * | 1981-07-23 | 1983-05-10 | Kali Chemie Ag | Process for the preparation of trifluoracetic acid derivatives |
| DE3129273A1 (de) * | 1981-07-24 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von aldehyden |
| DE3326875A1 (de) * | 1983-07-26 | 1985-02-14 | Bayer Ag, 5090 Leverkusen | Neue fluorpivalsaeurefluoride und verfahren zu ihrer herstellung |
| IT1230097B (it) * | 1989-04-27 | 1991-10-05 | Ausimont Srl | Procedimento per preparare perfluorosuccinilfluoruro. |
| US5557010A (en) * | 1992-06-25 | 1996-09-17 | The Dow Chemical Company | Preparation of a 2,3-dihaloperfluorocarbonyl halide |
| DE4342601A1 (de) * | 1993-08-13 | 1995-02-16 | Solvay Fluor & Derivate | Verfahren zur Herstellung von Poly- und Perfluorcarbonsäurechloriden |
| EP0659729B1 (de) * | 1993-12-23 | 1998-06-24 | Solvay Fluor und Derivate GmbH | Verfahren zur Herstellung von Polyfluorchlor- und Perfluorcarbonsäurechloriden unter Chlorzusatz |
| CN102351681B (zh) * | 2011-08-16 | 2013-12-25 | 浙江大学 | 一种连续合成三氟乙酰氯和硫酰氟的方法 |
| CN104671219A (zh) * | 2013-12-02 | 2015-06-03 | 浙江化工院科技有限公司 | 一种硫酰氯分离提纯工艺 |
| KR20220131263A (ko) * | 2020-01-22 | 2022-09-27 | 칸토 덴카 코교 가부시키가이샤 | 카르복실산 플루오라이드의 정제 방법 |
| US11987553B2 (en) * | 2020-09-11 | 2024-05-21 | Honeywell International Inc. | Methods for removal of sulfur dioxide (SO2) from trifluoroacetyl chloride (TFAC) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160659A (en) * | 1960-05-20 | 1964-12-08 | Halocarbon Prod Corp | Preparation of perfluoro-and perchlorofluoro-acetyl chloride |
-
1969
- 1969-04-05 DE DE1917630A patent/DE1917630C3/de not_active Expired
-
1970
- 1970-03-17 GB GB02881/70A patent/GB1248175A/en not_active Expired
- 1970-03-18 NL NL7003847A patent/NL7003847A/xx unknown
- 1970-03-20 FR FR7010216A patent/FR2038257B1/fr not_active Expired
- 1970-04-06 US US00031048A patent/US3725475A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1248175A (en) | 1971-09-29 |
| FR2038257B1 (enExample) | 1976-02-06 |
| US3725475A (en) | 1973-04-03 |
| NL7003847A (enExample) | 1970-10-07 |
| FR2038257A1 (enExample) | 1971-01-08 |
| DE1917630A1 (de) | 1970-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |