DE2557162A1 - Verfahren zur herstellung von trichloraethylchloroformiat - Google Patents
Verfahren zur herstellung von trichloraethylchloroformiatInfo
- Publication number
- DE2557162A1 DE2557162A1 DE19752557162 DE2557162A DE2557162A1 DE 2557162 A1 DE2557162 A1 DE 2557162A1 DE 19752557162 DE19752557162 DE 19752557162 DE 2557162 A DE2557162 A DE 2557162A DE 2557162 A1 DE2557162 A1 DE 2557162A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- temperature
- phosgene
- reaction
- trichloroethanol
- 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
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 13
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- -1 for example Chemical compound 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7443379A FR2296615A1 (fr) | 1974-12-31 | 1974-12-31 | Procede perfectionne de fabrication du chloroformiate de trichloroethyle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2557162A1 true DE2557162A1 (de) | 1976-07-08 |
| DE2557162C2 DE2557162C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-21 |
Family
ID=9146799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752557162 Granted DE2557162A1 (de) | 1974-12-31 | 1975-12-18 | Verfahren zur herstellung von trichloraethylchloroformiat |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0157739A1 (de) * | 1984-03-29 | 1985-10-09 | Ciba-Geigy Ag | Substituierte 1-Propanole, Verfahren zu deren Herstellung, Chlorameisensäureester und deren Verwendung |
| US4734516A (en) * | 1985-03-28 | 1988-03-29 | Ciba-Geigy Corporation | Process for the preparation of partially halogenated 1-propanols |
| US4759881A (en) * | 1985-03-11 | 1988-07-26 | Ciba-Geigy Corporation | Process for the preparation of trifluorodichloroethyl-substituted acids and zinc compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL67077A (en) * | 1981-11-10 | 1986-04-29 | Poudres & Explosifs Ste Nale | Preparation of alpha-chloromethyl chloroformate |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE118537C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE358125C (de) * | 1920-09-14 | 1922-09-04 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung eines Esters aus Trichloraethylalkohol |
| FR1338931A (fr) * | 1961-08-17 | 1963-10-04 | Union Carbide Corp | Procédé de fabrication de chloroformiates d'aryle |
| GB1288627A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-12-12 | 1972-09-13 |
-
1974
- 1974-12-31 FR FR7443379A patent/FR2296615A1/fr active Granted
-
1975
- 1975-11-14 IE IE247775A patent/IE42100B1/en unknown
- 1975-11-24 NL NL7513679A patent/NL185777C/xx not_active IP Right Cessation
- 1975-12-02 GB GB4946075A patent/GB1474867A/en not_active Expired
- 1975-12-11 IT IT7005775A patent/IT1051487B/it active
- 1975-12-18 LU LU74051A patent/LU74051A1/xx unknown
- 1975-12-18 DE DE19752557162 patent/DE2557162A1/de active Granted
- 1975-12-30 DK DK593575A patent/DK593575A/da unknown
- 1975-12-31 BE BE163246A patent/BE837238A/xx not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE118537C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE358125C (de) * | 1920-09-14 | 1922-09-04 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung eines Esters aus Trichloraethylalkohol |
| FR1338931A (fr) * | 1961-08-17 | 1963-10-04 | Union Carbide Corp | Procédé de fabrication de chloroformiates d'aryle |
| GB1288627A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-12-12 | 1972-09-13 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0157739A1 (de) * | 1984-03-29 | 1985-10-09 | Ciba-Geigy Ag | Substituierte 1-Propanole, Verfahren zu deren Herstellung, Chlorameisensäureester und deren Verwendung |
| US4759881A (en) * | 1985-03-11 | 1988-07-26 | Ciba-Geigy Corporation | Process for the preparation of trifluorodichloroethyl-substituted acids and zinc compounds |
| US4734516A (en) * | 1985-03-28 | 1988-03-29 | Ciba-Geigy Corporation | Process for the preparation of partially halogenated 1-propanols |
Also Published As
| Publication number | Publication date |
|---|---|
| IE42100L (en) | 1976-06-30 |
| NL7513679A (nl) | 1976-07-02 |
| LU74051A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-01 |
| BE837238A (fr) | 1976-06-30 |
| NL185777C (nl) | 1990-07-16 |
| FR2296615B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-08 |
| GB1474867A (en) | 1977-05-25 |
| NL185777B (nl) | 1990-02-16 |
| DK593575A (da) | 1976-07-01 |
| IT1051487B (it) | 1981-04-21 |
| DE2557162C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-21 |
| FR2296615A1 (fr) | 1976-07-30 |
| IE42100B1 (en) | 1980-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |