DE3319451A1 - Verfahren zur herstellung von 0-methyl-n-vinylurethan - Google Patents
Verfahren zur herstellung von 0-methyl-n-vinylurethanInfo
- Publication number
- DE3319451A1 DE3319451A1 DE19833319451 DE3319451A DE3319451A1 DE 3319451 A1 DE3319451 A1 DE 3319451A1 DE 19833319451 DE19833319451 DE 19833319451 DE 3319451 A DE3319451 A DE 3319451A DE 3319451 A1 DE3319451 A1 DE 3319451A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- urethane
- methanol
- pyrolysis
- mother liquor
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 126
- 239000012452 mother liquor Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 238000000197 pyrolysis Methods 0.000 claims description 27
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 7
- 238000005119 centrifugation Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VJXNRWJRKPCHBX-UHFFFAOYSA-N ethyl n-ethoxy-n-methylcarbamate Chemical compound CCON(C)C(=O)OCC VJXNRWJRKPCHBX-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 alkyl vinyl ethers Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- WLMSZVULHUTVRG-UHFFFAOYSA-N prop-2-enoyl azide Chemical compound C=CC(=O)N=[N+]=[N-] WLMSZVULHUTVRG-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833319451 DE3319451A1 (de) | 1983-05-28 | 1983-05-28 | Verfahren zur herstellung von 0-methyl-n-vinylurethan |
US06/614,571 US4574159A (en) | 1983-05-28 | 1984-05-25 | Process for the preparation of O-methyl-N-vinylurethane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833319451 DE3319451A1 (de) | 1983-05-28 | 1983-05-28 | Verfahren zur herstellung von 0-methyl-n-vinylurethan |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3319451A1 true DE3319451A1 (de) | 1984-11-29 |
DE3319451C2 DE3319451C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-01-14 |
Family
ID=6200152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19833319451 Granted DE3319451A1 (de) | 1983-05-28 | 1983-05-28 | Verfahren zur herstellung von 0-methyl-n-vinylurethan |
Country Status (2)
Country | Link |
---|---|
US (1) | US4574159A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
DE (1) | DE3319451A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5233077A (en) * | 1992-04-01 | 1993-08-03 | Air Products And Chemicals, Inc. | Preparation of N-vinyl-O-alkyl carbamate |
JP3571795B2 (ja) * | 1995-04-18 | 2004-09-29 | 株式会社日本触媒 | N−(1−アルキルオキシアルキル)カルバメート類の気相分子内脱アルコール反応用触媒およびn−ビニルカルバメート類の製造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019231A (en) * | 1959-05-11 | 1962-01-30 | Jefferson Chem Co Inc | Method of transvinylating |
US3715385A (en) * | 1970-08-17 | 1973-02-06 | Atlantic Richfield Co | Process for the preparation of n-vinyl carbamic acid esters |
EP0009697A2 (de) * | 1978-09-30 | 1980-04-16 | Bayer Ag | Verfahren zur Herstellung von N-(Alpha-Methoxy-alkyl)-urethanen und neue N-(Alpha-methoxy-alkyl)-urethane |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2592254A (en) * | 1948-01-29 | 1952-04-08 | Eastman Kodak Co | Monomers and polymers of vinyl carbamic acid derivatives and their preparation |
DE1242590B (de) * | 1964-02-14 | 1967-06-22 | Hoechst Ag | Verfahren zur Herstellung von N-Vinyl-carbaminsaeureestern |
DE1173454B (de) * | 1963-05-11 | 1964-07-09 | Hoechst Ag | Verfahren zur Herstellung von N-Vinyl-carbaminsaeureestern |
DE2336977A1 (de) * | 1973-07-20 | 1975-02-13 | Hoechst Ag | Verfahren zur herstellung von sekundaeren n-vinylcarbonsaeureamiden |
-
1983
- 1983-05-28 DE DE19833319451 patent/DE3319451A1/de active Granted
-
1984
- 1984-05-25 US US06/614,571 patent/US4574159A/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019231A (en) * | 1959-05-11 | 1962-01-30 | Jefferson Chem Co Inc | Method of transvinylating |
US3715385A (en) * | 1970-08-17 | 1973-02-06 | Atlantic Richfield Co | Process for the preparation of n-vinyl carbamic acid esters |
EP0009697A2 (de) * | 1978-09-30 | 1980-04-16 | Bayer Ag | Verfahren zur Herstellung von N-(Alpha-Methoxy-alkyl)-urethanen und neue N-(Alpha-methoxy-alkyl)-urethane |
Non-Patent Citations (1)
Title |
---|
Soc. Chem. Belg. Bd. 66, 1957, S. 229-243 * |
Also Published As
Publication number | Publication date |
---|---|
US4574159A (en) | 1986-03-04 |
DE3319451C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-01-14 |
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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 |