DE1132117B - Verfahren zur Herstellung von Urethanen - Google Patents
Verfahren zur Herstellung von UrethanenInfo
- Publication number
- DE1132117B DE1132117B DEF27209A DEF0027209A DE1132117B DE 1132117 B DE1132117 B DE 1132117B DE F27209 A DEF27209 A DE F27209A DE F0027209 A DEF0027209 A DE F0027209A DE 1132117 B DE1132117 B DE 1132117B
- Authority
- DE
- Germany
- Prior art keywords
- acetone
- reaction
- found
- calculated
- phenol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000003673 urethanes Chemical class 0.000 title claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- -1 cycloaliphatic Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- WIIVKNLYINAMDA-UHFFFAOYSA-N 2,4,6-tris(diethylaminomethyl)phenol Chemical compound CCN(CC)CC1=CC(CN(CC)CC)=C(O)C(CN(CC)CC)=C1 WIIVKNLYINAMDA-UHFFFAOYSA-N 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- QAPHUXJGSNSWPK-UHFFFAOYSA-N 2,5-bis[(dimethylamino)methyl]benzene-1,4-diol Chemical compound CN(C)CC1=CC(O)=C(CN(C)C)C=C1O QAPHUXJGSNSWPK-UHFFFAOYSA-N 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- CIPOCPJRYUFXLL-UHFFFAOYSA-N 2,3,4-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C(CN(C)C)=C1CN(C)C CIPOCPJRYUFXLL-UHFFFAOYSA-N 0.000 description 1
- MHXBUQBHTYREBE-UHFFFAOYSA-N 2,4-dichloro-6-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(Cl)=CC(Cl)=C1O MHXBUQBHTYREBE-UHFFFAOYSA-N 0.000 description 1
- RQZGJWFANCGCHS-UHFFFAOYSA-N 2,6-bis[(dimethylamino)methyl]-4-methylphenol Chemical compound CN(C)CC1=CC(C)=CC(CN(C)C)=C1O RQZGJWFANCGCHS-UHFFFAOYSA-N 0.000 description 1
- FMFVDXUOAOXWDF-UHFFFAOYSA-N 2-(dimethylamino)-3,5-dimethylphenol Chemical compound CN(C)C1=C(C)C=C(C)C=C1O FMFVDXUOAOXWDF-UHFFFAOYSA-N 0.000 description 1
- HYVZRUQCAHFECM-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-methylphenol Chemical compound CN(C)CC1=CC(C)=CC=C1O HYVZRUQCAHFECM-UHFFFAOYSA-N 0.000 description 1
- WPEGHIRPYPPYDO-UHFFFAOYSA-N 4-chloro-2-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(Cl)=CC=C1O WPEGHIRPYPPYDO-UHFFFAOYSA-N 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 241001300479 Macroptilium Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WSKXXIMERYQVGJ-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1 WSKXXIMERYQVGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
- C07D215/34—Carbamates
-
- 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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE585318D BE585318A (en, 2012) | 1958-12-06 | ||
| US3125598D US3125598A (en) | 1958-12-06 | Dialkylaminoaryl arylcarbamates | |
| NL246083D NL246083A (en, 2012) | 1958-12-06 | ||
| DEF27209A DE1132117B (de) | 1958-12-06 | 1958-12-06 | Verfahren zur Herstellung von Urethanen |
| GB41374/59A GB906183A (en) | 1958-12-06 | 1959-12-04 | New esters of n-substituted carbamic acids |
| FR812226A FR1250683A (fr) | 1958-12-06 | 1959-12-05 | Fabrication de produits de condensation de composés aromatiques et d'isocyanates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27209A DE1132117B (de) | 1958-12-06 | 1958-12-06 | Verfahren zur Herstellung von Urethanen |
| DEF29887A DE1135888B (de) | 1959-11-20 | 1959-11-20 | Verfahren zur Herstellung von Urethanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1132117B true DE1132117B (de) | 1962-06-28 |
Family
ID=25974194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF27209A Pending DE1132117B (de) | 1958-12-06 | 1958-12-06 | Verfahren zur Herstellung von Urethanen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3125598A (en, 2012) |
| BE (1) | BE585318A (en, 2012) |
| DE (1) | DE1132117B (en, 2012) |
| GB (1) | GB906183A (en, 2012) |
| NL (1) | NL246083A (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3318889A (en) * | 1963-10-14 | 1967-05-09 | S B Penick & Company | 2-benzimidazole carbamates |
| US3382270A (en) * | 1963-11-20 | 1968-05-07 | Dow Chemical Co | Oligomers of alkyl aziridinyl carboxylates |
| NL6408165A (en, 2012) * | 1964-07-17 | 1966-01-18 | ||
| US3450818A (en) * | 1965-04-22 | 1969-06-17 | Murphy Chem Co Ltd The | Simultaneously effective antifungal and insecticidal or acaricidal pesticides |
| CH486841A (de) * | 1965-05-17 | 1970-03-15 | Ciba Geigy | Schädlingsbekämpfungsmittel bzw. ein vor dem Befall durch Schädlinge geschütztes nichttextiles Erzeugnis |
| US3857693A (en) * | 1965-10-14 | 1974-12-31 | Fmc Corp | Anilide carbamates as herbicides |
| US4124545A (en) * | 1973-05-22 | 1978-11-07 | Bayer Aktiengesellschaft | Carbamic acid esters as catalysts for trimerization of isocyanates |
| WO2008059953A1 (fr) * | 2006-11-17 | 2008-05-22 | Asahi Kasei Chemicals Corporation | Procédé de production d'isocyanate |
| RU2419603C2 (ru) * | 2006-11-17 | 2011-05-27 | Асахи Касеи Кемикалз Корпорейшн | Способ получения изоцианатов |
| TW200844080A (en) * | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
| US8895774B2 (en) * | 2008-05-15 | 2014-11-25 | Asahi Kasei Chemicals Corporation | Process for producing isocyanates using diaryl carbonate |
| US9233918B2 (en) * | 2008-05-15 | 2016-01-12 | Asahi Kasei Chemicals Corporation | Isocyanate production process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362508A (en) * | 1940-12-06 | 1944-11-14 | Merck & Co Inc | Therapeutic substances |
| US2843519A (en) * | 1952-11-18 | 1958-07-15 | Howard M Fitch | Pesticidal compositions comprising dimethyl carbamates of dimethyl amino and hetero-substituted methyl phenols and method of using same |
| AT185371B (de) * | 1953-06-23 | 1956-04-25 | Chemie Linz Ag | Verfahren zur Herstellung von neuen Polymethylen- bzw. Phenylen-bis-carbaminsäureestern |
-
0
- BE BE585318D patent/BE585318A/xx unknown
- NL NL246083D patent/NL246083A/xx unknown
- US US3125598D patent/US3125598A/en not_active Expired - Lifetime
-
1958
- 1958-12-06 DE DEF27209A patent/DE1132117B/de active Pending
-
1959
- 1959-12-04 GB GB41374/59A patent/GB906183A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE585318A (en, 2012) | |
| GB906183A (en) | 1962-09-19 |
| NL246083A (en, 2012) | |
| US3125598A (en) | 1964-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1132117B (de) | Verfahren zur Herstellung von Urethanen | |
| DE3123018A1 (de) | Substituierte cyclohexan-1,3-dion-derivate, verfahren zu deren herstellung und herbicide mittel | |
| EP0153561A1 (de) | Neue Diisocyanate und ihre Verwendung zur Herstellung von Polyurethankunststoffen | |
| EP0013414A2 (de) | Harnstoffderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide | |
| EP0028829A1 (de) | Harnstoffe mit cyclischen Substituenten, ihre Herstellung und Verwendung als Herbizide | |
| DE2157708C3 (de) | 2',6'-Dichlorbenzaldehyd-1alkyl-3-sulfonylsemicarbazone und Verfahren zu ihrer Herstellung | |
| DE1174757B (de) | Verfahren zur Herstellung von chlorierten Carbamidbenzaldoximen | |
| DE2706700A1 (de) | Verfahren zur herstellung von pyridazin-3-on-verbindungen, neue pyridazin-3-one und deren verwendung | |
| DE1254617B (de) | Verfahren zur Herstellung von N-Methyl-O-phenylcarbaminsaeureestern | |
| EP0023976B1 (de) | N-Aryl-N'-acryloyl-ureide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Mikrobizide | |
| DE1142599B (de) | Verfahren zur Herstellung von Carbaminsaeureestern | |
| DE1027930B (de) | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses | |
| DE1300113B (de) | Dithiophosphorsaeureester und Verfahren zu ihrer Herstellung | |
| DE2041996A1 (de) | Substituierte Uracile | |
| DE1248635B (de) | Verfahren zur Herstellung eines Alkenylmercaptophenyl - N - methyl-carbaminsäureesters | |
| DE69600662T2 (de) | Alkinylphenylaminosulfonylharnstoffe als Herbizide | |
| DE1941999C3 (de) | Substituierte S-haltige Alkanal- und Alkanonoximcarbamate, deren Herstellung und Verwendung | |
| DE968273C (de) | Verfahren zur Herstellung von trisubstituierten Harnstoffen | |
| AT356085B (de) | Verfahren zur herstellung von neuen anthranil- saeureestern | |
| DE1192202B (de) | Verfahren zur Herstellung von (Thiono) Phosphor-(on, in)-saeureestern | |
| DE2436712C3 (de) | Oxim-carbamat-thiophosphorsäure-und -dithiophosphorsäure-O.O.S-triester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| AT230896B (de) | Verfahren zur Herstellung von neuen Carbaminsäureestern | |
| AT231469B (de) | Verfahren zur Herstellung neuer Organophosphorverbindungen | |
| DE2901334A1 (de) | Neue harnstoffderivate | |
| DE19545757A1 (de) | 4,4'-(Phenylendiisopropyl)-bis(2,6-dialkylphenylisocyanate) |