DE2206365B2 - Verfahren zur Herstellung von N,Ndisubstituierten Carbaminsäurechloriden - Google Patents
Verfahren zur Herstellung von N,Ndisubstituierten CarbaminsäurechloridenInfo
- Publication number
- DE2206365B2 DE2206365B2 DE2206365A DE2206365A DE2206365B2 DE 2206365 B2 DE2206365 B2 DE 2206365B2 DE 2206365 A DE2206365 A DE 2206365A DE 2206365 A DE2206365 A DE 2206365A DE 2206365 B2 DE2206365 B2 DE 2206365B2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- carbamic acid
- phosgene
- reaction
- acid chloride
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 16
- -1 N, N-disubstituted carbamic acid chlorides Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RSAFAYLZKCYUQW-UHFFFAOYSA-N n,n-di(propan-2-yl)carbamoyl chloride Chemical compound CC(C)N(C(C)C)C(Cl)=O RSAFAYLZKCYUQW-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YMYSHUIWNUSQJA-UHFFFAOYSA-N carbamoyl chloride;pyrrolidine Chemical compound NC(Cl)=O.C1CCNC1 YMYSHUIWNUSQJA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- PNLJKMRPJPRAST-UHFFFAOYSA-N n-morpholin-4-ylcarbamoyl chloride Chemical compound ClC(=O)NN1CCOCC1 PNLJKMRPJPRAST-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- PAUXUUSDLAGVRJ-UHFFFAOYSA-N carbamoyl chloride;morpholine Chemical compound NC(Cl)=O.C1COCCN1 PAUXUUSDLAGVRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QTPUQXFLUMJEDT-UHFFFAOYSA-N n-pyrrolidin-1-ylcarbamoyl chloride Chemical compound ClC(=O)NN1CCCC1 QTPUQXFLUMJEDT-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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 |
|---|---|---|---|
| CH224671A CH547779A (de) | 1971-02-16 | 1971-02-16 | N,n-disubstituierte carbaminsaeurehalogenide. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2206365A1 DE2206365A1 (de) | 1972-08-31 |
| DE2206365B2 true DE2206365B2 (de) | 1980-07-31 |
Family
ID=4229271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206365A Ceased DE2206365B2 (de) | 1971-02-16 | 1972-02-10 | Verfahren zur Herstellung von N,Ndisubstituierten Carbaminsäurechloriden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3870707A (enExample) |
| BE (1) | BE779368A (enExample) |
| CH (1) | CH547779A (enExample) |
| DE (1) | DE2206365B2 (enExample) |
| ES (1) | ES399787A1 (enExample) |
| FR (1) | FR2125883A5 (enExample) |
| GB (1) | GB1363569A (enExample) |
| NL (1) | NL7201971A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601542A1 (de) * | 1976-01-16 | 1977-07-21 | Basf Ag | Verfahren zur herstellung von n-vinyl-n-alkyl-carbamidsaeurechloriden |
| DE3513599C1 (de) * | 1985-04-16 | 1986-06-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Carbamidsaeurechloriden sekundaerer Amine |
| FR2677017B1 (fr) * | 1991-05-27 | 1993-08-13 | Poudres & Explosifs Ste Nale | Procede de preparation de chlorures de carbamoyle aliphatiques ou araliphatiques n,n-disubstitues. |
| DE19951902A1 (de) * | 1999-10-28 | 2002-10-24 | Tesa Ag | Verfahren zur kontinuierlichen Herstellung von selbstklebenden Artikeln durch Beschichtung von zulaufenden bahnförmigen Materialien mit zweikomponentigen Polyurethanen |
| CN102321049A (zh) * | 2011-07-13 | 2012-01-18 | 浙江大学 | N-叔丁氧基羰基吡咯烷的制备方法 |
| CN104341374A (zh) * | 2014-11-11 | 2015-02-11 | 联化科技（德州）有限公司 | 一种吗啉碳酰氯类化合物的制备方法 |
| CN109369461A (zh) * | 2018-12-12 | 2019-02-22 | 湖南海利常德农药化工有限公司 | 一种二甲氨基甲酰氯的制备方法 |
| CN112479932A (zh) * | 2020-12-11 | 2021-03-12 | 安徽广信农化股份有限公司 | 一种二甲氨基甲酰氯的制备工艺 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3320308A (en) * | 1965-09-08 | 1967-05-16 | Progil | Preparation of alkyl and dialkyl carbamyl halides |
-
1971
- 1971-02-16 CH CH224671A patent/CH547779A/xx not_active IP Right Cessation
-
1972
- 1972-02-09 FR FR7204345A patent/FR2125883A5/fr not_active Expired
- 1972-02-10 DE DE2206365A patent/DE2206365B2/de not_active Ceased
- 1972-02-14 US US226320A patent/US3870707A/en not_active Expired - Lifetime
- 1972-02-15 NL NL7201971A patent/NL7201971A/xx unknown
- 1972-02-15 ES ES399787A patent/ES399787A1/es not_active Expired
- 1972-02-15 BE BE779368A patent/BE779368A/xx unknown
- 1972-02-15 GB GB693972A patent/GB1363569A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7201971A (enExample) | 1972-08-18 |
| CH547779A (de) | 1974-04-11 |
| ES399787A1 (es) | 1974-12-01 |
| US3870707A (en) | 1975-03-11 |
| BE779368A (fr) | 1972-08-16 |
| DE2206365A1 (de) | 1972-08-31 |
| GB1363569A (en) | 1974-08-14 |
| FR2125883A5 (enExample) | 1972-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8235 | Patent refused |