DE2411674C2 - Verfahren zur Herstellung von Carbonyldiisocyanat - Google Patents
Verfahren zur Herstellung von CarbonyldiisocyanatInfo
- Publication number
- DE2411674C2 DE2411674C2 DE2411674A DE2411674A DE2411674C2 DE 2411674 C2 DE2411674 C2 DE 2411674C2 DE 2411674 A DE2411674 A DE 2411674A DE 2411674 A DE2411674 A DE 2411674A DE 2411674 C2 DE2411674 C2 DE 2411674C2
- Authority
- DE
- Germany
- Prior art keywords
- nco
- chlorine
- acid
- salt
- preparation
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- YNKDRTCJDFVUTJ-UHFFFAOYSA-N carbonyl diisocyanate Chemical compound O=C=NC(=O)N=C=O YNKDRTCJDFVUTJ-UHFFFAOYSA-N 0.000 title description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims description 8
- 229950009390 symclosene Drugs 0.000 claims description 6
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002274 desiccant Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2411674A DE2411674C2 (de) | 1974-03-12 | 1974-03-12 | Verfahren zur Herstellung von Carbonyldiisocyanat |
| US05/548,954 US3941873A (en) | 1974-03-12 | 1975-02-11 | Process for the preparation of carbonyl diisocyanate |
| CH301575A CH593241A5 (enExample) | 1974-03-12 | 1975-03-10 | |
| LU72007A LU72007A1 (enExample) | 1974-03-12 | 1975-03-10 | |
| BE154160A BE826469A (fr) | 1974-03-12 | 1975-03-10 | Procede de preparation du diisocyanate de carbonyle |
| IT48522/75A IT1029997B (it) | 1974-03-12 | 1975-03-10 | Procedimento per produrre carbonil diisocianato |
| GB981175A GB1453585A (en) | 1974-03-12 | 1975-03-10 | Process for the preparation of carbonyl diisocyanate |
| IE530/75A IE40772B1 (en) | 1974-03-12 | 1975-03-11 | Process for the preparation of carbonyl diisocyanate |
| DK98875*#A DK98875A (enExample) | 1974-03-12 | 1975-03-11 | |
| ES435506A ES435506A1 (es) | 1974-03-12 | 1975-03-11 | Procedimiento para la obtencion de diisocianatos de carboni-lo. |
| NL7502947A NL7502947A (nl) | 1974-03-12 | 1975-03-12 | Werkwijze voor de bereiding van carbonyldiiso- cyanaat. |
| FR7507743A FR2272980B1 (enExample) | 1974-03-12 | 1975-03-12 | |
| JP50029158A JPS5826336B2 (ja) | 1974-03-12 | 1975-03-12 | カルボニルジイソシアネ−トノ セイゾウホウホウ |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2411674A DE2411674C2 (de) | 1974-03-12 | 1974-03-12 | Verfahren zur Herstellung von Carbonyldiisocyanat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2411674A1 DE2411674A1 (de) | 1975-10-02 |
| DE2411674C2 true DE2411674C2 (de) | 1982-07-01 |
Family
ID=5909769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2411674A Expired DE2411674C2 (de) | 1974-03-12 | 1974-03-12 | Verfahren zur Herstellung von Carbonyldiisocyanat |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3941873A (enExample) |
| JP (1) | JPS5826336B2 (enExample) |
| BE (1) | BE826469A (enExample) |
| CH (1) | CH593241A5 (enExample) |
| DE (1) | DE2411674C2 (enExample) |
| DK (1) | DK98875A (enExample) |
| ES (1) | ES435506A1 (enExample) |
| FR (1) | FR2272980B1 (enExample) |
| GB (1) | GB1453585A (enExample) |
| IE (1) | IE40772B1 (enExample) |
| IT (1) | IT1029997B (enExample) |
| LU (1) | LU72007A1 (enExample) |
| NL (1) | NL7502947A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1266288B (de) * | 1965-07-27 | 1968-04-18 | Dr Edgar Nachbaur | Carbonyldiisocyanat und Verfahren zu dessen Herstellung |
-
1974
- 1974-03-12 DE DE2411674A patent/DE2411674C2/de not_active Expired
-
1975
- 1975-02-11 US US05/548,954 patent/US3941873A/en not_active Expired - Lifetime
- 1975-03-10 CH CH301575A patent/CH593241A5/xx not_active IP Right Cessation
- 1975-03-10 IT IT48522/75A patent/IT1029997B/it active
- 1975-03-10 GB GB981175A patent/GB1453585A/en not_active Expired
- 1975-03-10 LU LU72007A patent/LU72007A1/xx unknown
- 1975-03-10 BE BE154160A patent/BE826469A/xx not_active IP Right Cessation
- 1975-03-11 IE IE530/75A patent/IE40772B1/xx unknown
- 1975-03-11 ES ES435506A patent/ES435506A1/es not_active Expired
- 1975-03-11 DK DK98875*#A patent/DK98875A/da not_active Application Discontinuation
- 1975-03-12 JP JP50029158A patent/JPS5826336B2/ja not_active Expired
- 1975-03-12 FR FR7507743A patent/FR2272980B1/fr not_active Expired
- 1975-03-12 NL NL7502947A patent/NL7502947A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| DK98875A (enExample) | 1975-09-13 |
| IE40772L (en) | 1975-09-12 |
| CH593241A5 (enExample) | 1977-11-30 |
| ES435506A1 (es) | 1977-06-16 |
| DE2411674A1 (de) | 1975-10-02 |
| IT1029997B (it) | 1979-03-20 |
| JPS5182226A (en) | 1976-07-19 |
| NL7502947A (nl) | 1975-09-16 |
| FR2272980B1 (enExample) | 1978-06-30 |
| FR2272980A1 (enExample) | 1975-12-26 |
| BE826469A (fr) | 1975-09-10 |
| GB1453585A (en) | 1976-10-27 |
| IE40772B1 (en) | 1979-08-15 |
| US3941873A (en) | 1976-03-02 |
| JPS5826336B2 (ja) | 1983-06-02 |
| LU72007A1 (enExample) | 1976-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |