DE2133467A1 - Seitenkettenfluorierte aromatische isocyanate - Google Patents
Seitenkettenfluorierte aromatische isocyanateInfo
- Publication number
- DE2133467A1 DE2133467A1 DE19712133467 DE2133467A DE2133467A1 DE 2133467 A1 DE2133467 A1 DE 2133467A1 DE 19712133467 DE19712133467 DE 19712133467 DE 2133467 A DE2133467 A DE 2133467A DE 2133467 A1 DE2133467 A1 DE 2133467A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- trifluoromethyl
- isocyanate
- trichloromethyl
- phenyl
- 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
- 239000012948 isocyanate Substances 0.000 title claims description 12
- 150000002513 isocyanates Chemical class 0.000 title claims description 4
- -1 fluorinated aromatic isocyanates Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 claims description 12
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 12
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 6
- OVTVKBUIKVWCBR-UHFFFAOYSA-N 1-isocyanato-2,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C(C(F)(F)F)=C1 OVTVKBUIKVWCBR-UHFFFAOYSA-N 0.000 claims description 3
- VAKRHEJOLWOBBZ-UHFFFAOYSA-N 1-isocyanato-2-(trichloromethyl)benzene Chemical class ClC(Cl)(Cl)C1=CC=CC=C1N=C=O VAKRHEJOLWOBBZ-UHFFFAOYSA-N 0.000 claims description 3
- OBLGYXZSVKQXKH-UHFFFAOYSA-N 2-isocyanato-1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(N=C=O)=C1 OBLGYXZSVKQXKH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- AZQHXOGNBRYMQJ-UHFFFAOYSA-N 4-chloro-1-isocyanato-2-(trichloromethyl)benzene Chemical compound ClC1=CC=C(N=C=O)C(C(Cl)(Cl)Cl)=C1 AZQHXOGNBRYMQJ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- LXDSQYVHAOIPCB-UHFFFAOYSA-N 1-isocyanato-2,4-bis(trichloromethyl)benzene Chemical compound ClC(C1=C(C=CC(=C1)C(Cl)(Cl)Cl)N=C=O)(Cl)Cl LXDSQYVHAOIPCB-UHFFFAOYSA-N 0.000 description 1
- GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
- OETSPPVLTPINEC-UHFFFAOYSA-N 1-isocyanato-4-(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(N=C=O)C=C1 OETSPPVLTPINEC-UHFFFAOYSA-N 0.000 description 1
- QFLNTNZHBHFKBJ-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trichloromethyl)benzene Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CC=C1N=C=O QFLNTNZHBHFKBJ-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- SBDPJLJFODHSFF-UHFFFAOYSA-N 4-chloro-1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1N=C=O SBDPJLJFODHSFF-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IGHVFPJIXMSFPR-UHFFFAOYSA-N ClC(Cl)(Cl)C1=C(C(=CC=C1)Cl)N=C=O Chemical compound ClC(Cl)(Cl)C1=C(C(=CC=C1)Cl)N=C=O IGHVFPJIXMSFPR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE785867D BE785867A (fr) | 1971-07-06 | Isocyanates aromatiques fluores en chaine laterale et leur procede de preparation | |
| DE19712133467 DE2133467A1 (de) | 1971-07-06 | 1971-07-06 | Seitenkettenfluorierte aromatische isocyanate |
| US00265021A US3829460A (en) | 1971-07-06 | 1972-06-21 | Preparation of trifluoromethyl aromatic isocyanates |
| NL7209321A NL7209321A (enExample) | 1971-07-06 | 1972-07-03 | |
| CH1001572A CH585700A5 (enExample) | 1971-07-06 | 1972-07-04 | |
| FR7224533A FR2145306A5 (enExample) | 1971-07-06 | 1972-07-06 | |
| GB3167972A GB1350353A (en) | 1971-07-06 | 1972-07-06 | Side-chain-fluorinated aromatic isocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712133467 DE2133467A1 (de) | 1971-07-06 | 1971-07-06 | Seitenkettenfluorierte aromatische isocyanate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2133467A1 true DE2133467A1 (de) | 1973-08-09 |
Family
ID=5812770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712133467 Pending DE2133467A1 (de) | 1971-07-06 | 1971-07-06 | Seitenkettenfluorierte aromatische isocyanate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3829460A (enExample) |
| BE (1) | BE785867A (enExample) |
| CH (1) | CH585700A5 (enExample) |
| DE (1) | DE2133467A1 (enExample) |
| FR (1) | FR2145306A5 (enExample) |
| GB (1) | GB1350353A (enExample) |
| NL (1) | NL7209321A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1232286A (en) * | 1983-06-15 | 1988-02-02 | Henry C. Lin | Method for the preparation of benzenamines |
| US4745215A (en) * | 1987-04-03 | 1988-05-17 | International Business Machines Corporation | Fluorine containing dicyanate resins |
| CN112480364A (zh) * | 2017-04-10 | 2021-03-12 | 三井化学株式会社 | 苯二甲撑二异氰酸酯组合物、苯二甲撑二异氰酸酯改性物组合物、二液型树脂原料及树脂 |
-
0
- BE BE785867D patent/BE785867A/xx unknown
-
1971
- 1971-07-06 DE DE19712133467 patent/DE2133467A1/de active Pending
-
1972
- 1972-06-21 US US00265021A patent/US3829460A/en not_active Expired - Lifetime
- 1972-07-03 NL NL7209321A patent/NL7209321A/xx unknown
- 1972-07-04 CH CH1001572A patent/CH585700A5/xx not_active IP Right Cessation
- 1972-07-06 FR FR7224533A patent/FR2145306A5/fr not_active Expired
- 1972-07-06 GB GB3167972A patent/GB1350353A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7209321A (enExample) | 1973-01-09 |
| BE785867A (fr) | 1973-01-05 |
| FR2145306A5 (enExample) | 1973-02-16 |
| GB1350353A (en) | 1974-04-18 |
| US3829460A (en) | 1974-08-13 |
| CH585700A5 (enExample) | 1977-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |