DE2258454C2 - Verfahren zur Herstellung von N-monosubstituierten Carbamaten - Google Patents
Verfahren zur Herstellung von N-monosubstituierten CarbamatenInfo
- Publication number
- DE2258454C2 DE2258454C2 DE2258454A DE2258454A DE2258454C2 DE 2258454 C2 DE2258454 C2 DE 2258454C2 DE 2258454 A DE2258454 A DE 2258454A DE 2258454 A DE2258454 A DE 2258454A DE 2258454 C2 DE2258454 C2 DE 2258454C2
- Authority
- DE
- Germany
- Prior art keywords
- carbamate
- optionally substituted
- general formula
- reaction
- urea
- 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 18
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 hydroxyl compound Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 150000003672 ureas Chemical class 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 235000013877 carbamide Nutrition 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- ZTIMKJROOYMUMU-UHFFFAOYSA-N butyl n-phenylcarbamate Chemical compound CCCCOC(=O)NC1=CC=CC=C1 ZTIMKJROOYMUMU-UHFFFAOYSA-N 0.000 description 2
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 1
- ZFJBSYYIOPSWAE-UHFFFAOYSA-N 1,1-diethyl-3-phenylurea Chemical compound CCN(CC)C(=O)NC1=CC=CC=C1 ZFJBSYYIOPSWAE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DHBPHQBXINVWDZ-UHFFFAOYSA-N C=1C=CC=CC=1N(C(=O)O)CCCCN(C(O)=O)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1N(C(=O)O)CCCCN(C(O)=O)C1=CC=CC=C1 DHBPHQBXINVWDZ-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JEAXEFPTKIJYRO-UHFFFAOYSA-N cyclohexyl n-cyclohexylcarbamate Chemical compound C1CCCCC1OC(=O)NC1CCCCC1 JEAXEFPTKIJYRO-UHFFFAOYSA-N 0.000 description 1
- CEUNIYVZFAQQSI-UHFFFAOYSA-N cyclohexyl n-phenylcarbamate Chemical compound C1CCCCC1OC(=O)NC1=CC=CC=C1 CEUNIYVZFAQQSI-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- OVPLZYJGTGDFNB-UHFFFAOYSA-N propan-2-yl carbamate Chemical compound CC(C)OC(N)=O OVPLZYJGTGDFNB-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5658171A GB1410590A (en) | 1971-12-06 | 1971-12-06 | Process for the preparation of carbamates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2258454A1 DE2258454A1 (de) | 1973-06-14 |
| DE2258454C2 true DE2258454C2 (de) | 1983-03-03 |
Family
ID=10476997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2258454A Expired DE2258454C2 (de) | 1971-12-06 | 1972-11-29 | Verfahren zur Herstellung von N-monosubstituierten Carbamaten |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3873553A (OSRAM) |
| JP (1) | JPS5811858B2 (OSRAM) |
| BE (1) | BE792313A (OSRAM) |
| BR (1) | BR7208556D0 (OSRAM) |
| CH (1) | CH574400A5 (OSRAM) |
| DD (1) | DD100938A5 (OSRAM) |
| DE (1) | DE2258454C2 (OSRAM) |
| FR (1) | FR2164293A5 (OSRAM) |
| GB (1) | GB1410590A (OSRAM) |
| IL (1) | IL40997A0 (OSRAM) |
| IT (1) | IT1027509B (OSRAM) |
| ZA (1) | ZA728664B (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156784A (en) * | 1974-12-18 | 1979-05-29 | Basf Aktiengesellschaft | Manufacture of carbamates |
| FR2375272A1 (fr) * | 1976-12-23 | 1978-07-21 | Poudres & Explosifs Ste Nale | Nouveaux poly(carbonates-urethannes)triols et leurs applications |
| US4172948A (en) * | 1979-01-24 | 1979-10-30 | Atlantic Richfield Company | Preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates |
| DE2908252A1 (de) * | 1979-03-02 | 1980-09-11 | Bayer Ag | Verfahren zur herstellung von urethanen |
| US4214073A (en) * | 1979-05-29 | 1980-07-22 | Societe Nationale Des Poudres Et Explosifs | Poly-(carbonate-urethane)-triols and preparation thereof |
| DE3070380D1 (en) * | 1979-09-21 | 1985-05-02 | Basf Wyandotte Corp | Rigid, non-cellular urethane polymer composition modified with reaction product of an isocyanate and an alcohol and a process for producing it |
| DE2943550A1 (de) * | 1979-10-27 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von urethanen und ihre verwendung als ausgangsmaterial zur herstellung von isocyanaten |
| HU184063B (en) * | 1979-11-08 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing carbamoic-acid-phenyl-ester derivatives |
| DE3035393A1 (de) * | 1980-09-19 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung vonn-substituierten imidodicarbonsaeurediarylestern |
| US4925971A (en) * | 1987-12-08 | 1990-05-15 | Asahi Kasei Kogyo Kabushiki Kaisha | Method for producing aliphatic o-arylurethanes |
| CN103588680B (zh) * | 2009-08-21 | 2016-08-10 | 旭化成株式会社 | N-取代氨基甲酸酯的输送用和储藏用组合物及制造异氰酸酯的方法 |
| US8957241B2 (en) | 2011-02-21 | 2015-02-17 | Asahi Kasei Chemicals Corporation | Method for producing carbonyl compound |
| RU2637317C1 (ru) * | 2016-11-25 | 2017-12-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" | Способ получения n-алкил-о-арилкарбаматов |
| MX2021015391A (es) | 2019-07-03 | 2022-01-24 | Procter & Gamble | Estructuras fibrosas que contienen surfactantes cationicos y acidos solubles. |
-
0
- BE BE792313D patent/BE792313A/xx unknown
-
1971
- 1971-12-06 GB GB5658171A patent/GB1410590A/en not_active Expired
-
1972
- 1972-11-29 IT IT32241/72A patent/IT1027509B/it active
- 1972-11-29 DE DE2258454A patent/DE2258454C2/de not_active Expired
- 1972-12-05 BR BR8556/72A patent/BR7208556D0/pt unknown
- 1972-12-05 IL IL40997A patent/IL40997A0/xx unknown
- 1972-12-05 FR FR7243134A patent/FR2164293A5/fr not_active Expired
- 1972-12-06 DD DD167323A patent/DD100938A5/xx unknown
- 1972-12-06 US US312752A patent/US3873553A/en not_active Expired - Lifetime
- 1972-12-06 JP JP47122373A patent/JPS5811858B2/ja not_active Expired
- 1972-12-06 ZA ZA728664A patent/ZA728664B/xx unknown
- 1972-12-06 CH CH1772772A patent/CH574400A5/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA728664B (en) | 1973-08-29 |
| JPS5811858B2 (ja) | 1983-03-04 |
| IL40997A0 (en) | 1973-02-28 |
| GB1410590A (en) | 1975-10-22 |
| CH574400A5 (OSRAM) | 1976-04-15 |
| US3873553A (en) | 1975-03-25 |
| DE2258454A1 (de) | 1973-06-14 |
| JPS4864025A (OSRAM) | 1973-09-05 |
| BR7208556D0 (pt) | 1973-09-25 |
| FR2164293A5 (OSRAM) | 1973-07-27 |
| IT1027509B (it) | 1978-12-20 |
| DD100938A5 (OSRAM) | 1973-10-12 |
| BE792313A (fr) | 1973-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |