DE2758171C2 - Verfahren zur Herstellung von Isopropyl-, tert.-Butyl- oder Cyclohexylisocyanat - Google Patents
Verfahren zur Herstellung von Isopropyl-, tert.-Butyl- oder CyclohexylisocyanatInfo
- Publication number
- DE2758171C2 DE2758171C2 DE2758171A DE2758171A DE2758171C2 DE 2758171 C2 DE2758171 C2 DE 2758171C2 DE 2758171 A DE2758171 A DE 2758171A DE 2758171 A DE2758171 A DE 2758171A DE 2758171 C2 DE2758171 C2 DE 2758171C2
- Authority
- DE
- Germany
- Prior art keywords
- phosgene
- urea
- isocyanate
- hours
- isopropyl
- 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 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 title claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 title description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000003672 ureas Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 description 26
- 239000012948 isocyanate Substances 0.000 description 22
- 239000004202 carbamide Substances 0.000 description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
- 150000002513 isocyanates Chemical class 0.000 description 18
- -1 aromatic isocyanates Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 239000005662 Paraffin oil Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical group C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- PAPHVZDIBBAOTF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2,5-dioxo-n-propan-2-ylimidazolidine-1-carboxamide Chemical compound O=C1N(C(=O)NC(C)C)C(=O)CN1C1=CC(Cl)=CC(Cl)=C1 PAPHVZDIBBAOTF-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FUQFHOLPJJETAP-UHFFFAOYSA-N carbamimidoyl chloride;hydron;chloride Chemical compound Cl.NC(Cl)=N FUQFHOLPJJETAP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/06—Preparation of derivatives of isocyanic acid from or via ureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7639801A FR2375197A1 (fr) | 1976-12-27 | 1976-12-27 | Procede de fabrication d'isocyanates aliphatiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2758171A1 DE2758171A1 (de) | 1978-07-06 |
| DE2758171C2 true DE2758171C2 (de) | 1985-08-08 |
Family
ID=9181844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2758171A Expired DE2758171C2 (de) | 1976-12-27 | 1977-12-27 | Verfahren zur Herstellung von Isopropyl-, tert.-Butyl- oder Cyclohexylisocyanat |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4384999A (en) * | 1980-10-09 | 1983-05-24 | Spaziante Placido M | Preparation of alkyl isocyanates |
| JPS61149559U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1985-03-07 | 1986-09-16 | ||
| JP6501043B1 (ja) | 2017-06-30 | 2019-04-17 | Ｊｆｅスチール株式会社 | 構造用鋼材および構造物 |
| CN110168123B (zh) | 2017-12-14 | 2020-08-25 | 新日铁住金株式会社 | 钢材 |
| CN113831263A (zh) * | 2021-10-18 | 2021-12-24 | 宁夏瑞泰科技股份有限公司 | 一种采用微通道反应器合成异氰酸正丁酯的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1081451B (de) * | 1958-12-19 | 1960-05-12 | Bayer Ag | Verfahren zur Herstellung von Di- und Polyisocyanaten |
| US3275669A (en) * | 1962-09-10 | 1966-09-27 | Upjohn Co | Preparation of organic isocyanates from n, n'-disubstituted allophanyl chlorides |
| US3936484A (en) * | 1974-09-25 | 1976-02-03 | Atlantic Richfield Company | Production of isocyanates from substituted ureas |
-
1976
- 1976-12-27 FR FR7639801A patent/FR2375197A1/fr active Granted
-
1977
- 1977-12-12 US US05/859,930 patent/US4151193A/en not_active Expired - Lifetime
- 1977-12-20 IL IL53662A patent/IL53662A/xx unknown
- 1977-12-21 GB GB53227/77A patent/GB1552740A/en not_active Expired
- 1977-12-21 CH CH1581677A patent/CH627154A5/fr not_active IP Right Cessation
- 1977-12-22 NL NL7714279A patent/NL7714279A/xx not_active Application Discontinuation
- 1977-12-23 BE BE183834A patent/BE862306A/xx not_active IP Right Cessation
- 1977-12-26 JP JP52157167A patent/JPS5839151B2/ja not_active Expired
- 1977-12-27 DE DE2758171A patent/DE2758171C2/de not_active Expired
- 1977-12-27 AT AT932277A patent/AT355004B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL53662A (en) | 1981-09-13 |
| FR2375197A1 (fr) | 1978-07-21 |
| ATA932277A (de) | 1979-07-15 |
| US4151193A (en) | 1979-04-24 |
| DE2758171A1 (de) | 1978-07-06 |
| JPS5839151B2 (ja) | 1983-08-27 |
| IL53662A0 (en) | 1978-03-10 |
| JPS5382723A (en) | 1978-07-21 |
| NL7714279A (nl) | 1978-06-29 |
| FR2375197B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-04-13 |
| AT355004B (de) | 1980-02-11 |
| CH627154A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-12-31 |
| BE862306A (fr) | 1978-06-23 |
| GB1552740A (en) | 1979-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0623587A1 (de) | Verfahren zur Herstellung von amphoteren Tensiden | |
| DE2038320C3 (de) | Nichtwäßrige Wasserstoffperpxid-Lösungen | |
| EP0157088B1 (de) | Verfahren zur Herstellung von Polyisocyanaten mit Biuretstruktur | |
| DE2758171C2 (de) | Verfahren zur Herstellung von Isopropyl-, tert.-Butyl- oder Cyclohexylisocyanat | |
| DE2512514A1 (de) | Verfahren zur herstellung von aliphatischen isocyanaten | |
| DE2826452A1 (de) | Verfahren zur herstellung von substituierten guanidinen | |
| DE3850230T2 (de) | Verfahren zur Herstellung von Alkylthioethylaminsalzen. | |
| EP1149070B1 (de) | Verfahren zur herstellung von methylcarbazat | |
| EP0253214A1 (de) | Verfahren zur Herstellung von Chlorcarbonsäurechloriden | |
| EP0757983B1 (de) | Verfahren zur Herstellung von tertiären Aminoxiden | |
| DE69604513T2 (de) | Verfahren zur Herstellung substituierter Carbodiimide | |
| DE2305517C3 (de) | 2-Imino-13-dithiacyclobutane, Verfahren zu ihrer Herstellung und sie enthaltende Warmblüterschutzmittel gegen Schildzecken | |
| DE19731782A1 (de) | Verfahren zur Herstellung von Pyridylmethylisocyanaten | |
| DE2804082A1 (de) | Verfahren zur herstellung von organischen isocyanaten | |
| DE2645692C2 (de) | Thiazolidin-4-carbonitrile | |
| DE2603508C2 (de) | Verfahren zur Herstellung von " Isothiocyanaten | |
| DE2519315C2 (de) | Verfahren zur Herstellung von 3-Trichlormethyl-5-chlor-1,2,4-thiadiazol | |
| DE1251304B (de) | Verfahren zur Herstellung von a [0 0 Dialkyl-mono- bzw -ditniophosphoryl] - carbonsäureamiden | |
| DE2336403A1 (de) | Verfahren zur herstellung von isocyanaten | |
| DE946710C (de) | Verfahren zur Herstellung von N-disubstituierten Sulfamidsaeurechloriden | |
| DE2349313A1 (de) | Verfahren zur herstellung von tetraalkylthiuramidsulfiden | |
| DE3111518A1 (de) | Salze von carbamoylsulfonsaeurederivaten und verfahren zu ihrer herstellung | |
| DE1140583B (de) | Verfahren zur Herstellung von o-[Bis-(2-chloraethyl)-amino]-phenyl-alanin | |
| WO1991013867A1 (de) | N-acyl-aminoalkyl-2-hydroxyethylsulfide und ein verfahren zu ihrer herstellung | |
| DE2606855C2 (de) | Verfahren zur Herstellung von Propionsäure-3,4-dichloranilid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. KLINGSEISEN, F., DIPL.-ING. ZUMSTEIN JUN., F., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8366 | Restricted maintained after opposition proceedings | ||
| 8305 | Restricted maintenance of patent after opposition | ||
| D4 | Patent maintained restricted | ||
| 8339 | Ceased/non-payment of the annual fee |