IE42100B1 - Process for the preparation of 2,2,2-trichloroethyl chloroformate - Google Patents
Process for the preparation of 2,2,2-trichloroethyl chloroformateInfo
- Publication number
- IE42100B1 IE42100B1 IE247775A IE247775A IE42100B1 IE 42100 B1 IE42100 B1 IE 42100B1 IE 247775 A IE247775 A IE 247775A IE 247775 A IE247775 A IE 247775A IE 42100 B1 IE42100 B1 IE 42100B1
- Authority
- IE
- Ireland
- Prior art keywords
- phosgene
- catalyst
- trichloroethyl chloroformate
- temperature
- reaction
- Prior art date
Links
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 28
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NIBKDWIGIKUFKL-UHFFFAOYSA-N 1,2,2-trichloroethanol Chemical compound OC(Cl)C(Cl)Cl NIBKDWIGIKUFKL-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 abstract description 11
- 238000004821 distillation Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-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
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PCOMINGFBSHUJD-UHFFFAOYSA-N 2-ethylpyridin-1-ium;chloride Chemical compound Cl.CCC1=CC=CC=N1 PCOMINGFBSHUJD-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- RLINOMBZHOPATD-UHFFFAOYSA-N 4-chloro-n,n-dimethylaniline;hydrochloride Chemical compound Cl.CN(C)C1=CC=C(Cl)C=C1 RLINOMBZHOPATD-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 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
- -1 aryl chloroformates Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 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
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011269 tar Substances 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 |
|---|---|
| IE42100L IE42100L (en) | 1976-06-30 |
| IE42100B1 true IE42100B1 (en) | 1980-06-04 |
Family
ID=9146799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE247775A IE42100B1 (en) | 1974-12-31 | 1975-11-14 | Process for the preparation of 2,2,2-trichloroethyl chloroformate |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE837238A (enrdf_load_stackoverflow) |
| DE (1) | DE2557162A1 (enrdf_load_stackoverflow) |
| DK (1) | DK593575A (enrdf_load_stackoverflow) |
| FR (1) | FR2296615A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1474867A (enrdf_load_stackoverflow) |
| IE (1) | IE42100B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1051487B (enrdf_load_stackoverflow) |
| LU (1) | LU74051A1 (enrdf_load_stackoverflow) |
| NL (1) | NL185777C (enrdf_load_stackoverflow) |
Families Citing this family (4)
| 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 |
| DE3560449D1 (en) * | 1984-03-29 | 1987-09-17 | Ciba Geigy Ag | Substituted 1-propanoles, process for their production, chloroformic-acid esters ad their use |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE118537C (enrdf_load_stackoverflow) * | ||||
| DE358125C (de) * | 1920-09-14 | 1922-09-04 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung eines Esters aus Trichloraethylalkohol |
| US3170946A (en) * | 1961-08-17 | 1965-02-23 | Union Carbide Corp | Preparation of arylchloroformates |
| US3642857A (en) * | 1968-12-12 | 1972-02-15 | Aldrich Chem Co Inc | 1 1 1-trichloro-2-propyl 2 2 2-trichloroethyl carbonate |
-
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 DE DE19752557162 patent/DE2557162A1/de active Granted
- 1975-12-18 LU LU74051A patent/LU74051A1/xx unknown
- 1975-12-30 DK DK593575A patent/DK593575A/da unknown
- 1975-12-31 BE BE163246A patent/BE837238A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2296615A1 (fr) | 1976-07-30 |
| DE2557162A1 (de) | 1976-07-08 |
| DK593575A (da) | 1976-07-01 |
| NL185777B (nl) | 1990-02-16 |
| GB1474867A (en) | 1977-05-25 |
| DE2557162C2 (enrdf_load_stackoverflow) | 1988-07-21 |
| LU74051A1 (enrdf_load_stackoverflow) | 1977-07-01 |
| FR2296615B1 (enrdf_load_stackoverflow) | 1977-07-08 |
| NL7513679A (nl) | 1976-07-02 |
| BE837238A (fr) | 1976-06-30 |
| IE42100L (en) | 1976-06-30 |
| NL185777C (nl) | 1990-07-16 |
| IT1051487B (it) | 1981-04-21 |
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