DE2450285A1 - Verfahren zur herstellung von isopropenyl-isocyanat - Google Patents
Verfahren zur herstellung von isopropenyl-isocyanatInfo
- Publication number
- DE2450285A1 DE2450285A1 DE19742450285 DE2450285A DE2450285A1 DE 2450285 A1 DE2450285 A1 DE 2450285A1 DE 19742450285 DE19742450285 DE 19742450285 DE 2450285 A DE2450285 A DE 2450285A DE 2450285 A1 DE2450285 A1 DE 2450285A1
- Authority
- DE
- Germany
- Prior art keywords
- isopropenyl
- pyrolysis
- production
- isocyanate
- isopropenyl isocyanate
- 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
- UKQJZQQPMIFNHE-UHFFFAOYSA-N 2-isocyanatoprop-1-ene Chemical compound CC(=C)N=C=O UKQJZQQPMIFNHE-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000197 pyrolysis Methods 0.000 claims description 15
- FGQZKCDITLFTPQ-UHFFFAOYSA-N 3-prop-1-en-2-yl-1,4,2-dioxazol-5-one Chemical compound CC(=C)C1=NOC(=O)O1 FGQZKCDITLFTPQ-UHFFFAOYSA-N 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/08—Preparation of derivatives of isocyanic acid from or via heterocyclic compounds, e.g. pyrolysis of furoxans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742450285 DE2450285A1 (de) | 1974-10-23 | 1974-10-23 | Verfahren zur herstellung von isopropenyl-isocyanat |
| US05/621,175 US3960915A (en) | 1974-10-23 | 1975-10-09 | Process for the preparation of isopropenyl isocyanate |
| CH1351675A CH594610A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-23 | 1975-10-17 | |
| IL48323A IL48323A (en) | 1974-10-23 | 1975-10-20 | Preparation of isopropenyl isocyanate |
| NL7512299A NL7512299A (nl) | 1974-10-23 | 1975-10-20 | Werkwijze voor de bereiding van isopropenyl- -isocyanaat. |
| LU73618A LU73618A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-23 | 1975-10-21 | |
| GB4312375A GB1462588A (en) | 1974-10-23 | 1975-10-21 | Process for the preparation of isopropenyl isocyanate |
| BE161138A BE834742A (fr) | 1974-10-23 | 1975-10-22 | Procede de preparation de l'isocyanate d'isopropenyle |
| BR7506919*A BR7506919A (pt) | 1974-10-23 | 1975-10-22 | Processo para a preparacao de isophopenil-isocianato |
| DK476175A DK476175A (da) | 1974-10-23 | 1975-10-22 | Fremgangsmade til fremstilling af isopropenyl-isocyanat |
| IE2299/75A IE41919B1 (en) | 1974-10-23 | 1975-10-22 | Process for the preparation of isopropenyl isocyanate |
| FR7532531A FR2289492A1 (fr) | 1974-10-23 | 1975-10-23 | Procede de preparation d'isocyanate d'isopropenyle |
| JP50126965A JPS5165717A (en) | 1974-10-23 | 1975-10-23 | Isopuropeniruisoshianeeto no seiho |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742450285 DE2450285A1 (de) | 1974-10-23 | 1974-10-23 | Verfahren zur herstellung von isopropenyl-isocyanat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2450285A1 true DE2450285A1 (de) | 1976-04-29 |
Family
ID=5928925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742450285 Pending DE2450285A1 (de) | 1974-10-23 | 1974-10-23 | Verfahren zur herstellung von isopropenyl-isocyanat |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572804A (en) * | 1984-12-17 | 1986-02-25 | The Dow Chemical Company | Preparation of unsaturated isocyanates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6615003A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-10-22 | 1967-04-24 | ||
| US3480595A (en) * | 1966-11-07 | 1969-11-25 | Sinclair Research Inc | Addition polymers of ethylenically-unsaturated cyclic nitrile sulfites,carbonates and oxalates |
| FR2050902A5 (en) * | 1969-06-27 | 1971-04-02 | Dow Chemical Co | Organic isocyanate prodn by pyrolysis of - isocyanurates |
| DE2247724A1 (de) * | 1972-09-27 | 1974-04-04 | Basf Ag | Verfahren zur herstellung von lalkenylisocyanaten |
-
1974
- 1974-10-23 DE DE19742450285 patent/DE2450285A1/de active Pending
-
1975
- 1975-10-09 US US05/621,175 patent/US3960915A/en not_active Expired - Lifetime
- 1975-10-17 CH CH1351675A patent/CH594610A5/xx not_active IP Right Cessation
- 1975-10-20 NL NL7512299A patent/NL7512299A/xx not_active Application Discontinuation
- 1975-10-20 IL IL48323A patent/IL48323A/en unknown
- 1975-10-21 GB GB4312375A patent/GB1462588A/en not_active Expired
- 1975-10-21 LU LU73618A patent/LU73618A1/xx unknown
- 1975-10-22 IE IE2299/75A patent/IE41919B1/en unknown
- 1975-10-22 DK DK476175A patent/DK476175A/da unknown
- 1975-10-22 BR BR7506919*A patent/BR7506919A/pt unknown
- 1975-10-22 BE BE161138A patent/BE834742A/xx unknown
- 1975-10-23 JP JP50126965A patent/JPS5165717A/ja active Pending
- 1975-10-23 FR FR7532531A patent/FR2289492A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE834742A (fr) | 1976-04-22 |
| FR2289492A1 (fr) | 1976-05-28 |
| IL48323A (en) | 1977-12-30 |
| BR7506919A (pt) | 1976-08-17 |
| DK476175A (da) | 1976-04-24 |
| JPS5165717A (en) | 1976-06-07 |
| LU73618A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-19 |
| IL48323A0 (en) | 1975-12-31 |
| FR2289492B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-07-06 |
| NL7512299A (nl) | 1976-04-27 |
| US3960915A (en) | 1976-06-01 |
| CH594610A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-13 |
| IE41919B1 (en) | 1980-04-23 |
| GB1462588A (en) | 1977-01-26 |
| IE41919L (en) | 1976-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |