JPH021432A - ２，２‐ビス（４‐アミノフェニル）ヘキサフルオロプロパンの製造法 - Google Patents
２，２‐ビス（４‐アミノフェニル）ヘキサフルオロプロパンの製造法Info
- Publication number
- JPH021432A JPH021432A JP63141822A JP14182288A JPH021432A JP H021432 A JPH021432 A JP H021432A JP 63141822 A JP63141822 A JP 63141822A JP 14182288 A JP14182288 A JP 14182288A JP H021432 A JPH021432 A JP H021432A
- Authority
- JP
- Japan
- Prior art keywords
- solution
- bis
- hexafluoropropane
- aminophenyl
- carboxyphenyl
- 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.)
- Granted
Links
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims abstract description 29
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 20
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000001540 azides Chemical class 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000012948 isocyanate Substances 0.000 claims abstract description 8
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 8
- PHQYMDAUTAXXFZ-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C=C1 PHQYMDAUTAXXFZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 azide compound Chemical class 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- YMTNDQJOFCTPBI-UHFFFAOYSA-N 4-[2-(4-carbonochloridoylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoyl chloride Chemical compound C=1C=C(C(Cl)=O)C=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(Cl)=O)C=C1 YMTNDQJOFCTPBI-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004642 Polyimide Substances 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 3
- 229920001721 polyimide Polymers 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OWEIAGSMFHSSES-UHFFFAOYSA-N 1-[1,1,1,3,3,3-hexafluoro-2-(4-methylphenyl)propan-2-yl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C)C=C1 OWEIAGSMFHSSES-UHFFFAOYSA-N 0.000 description 1
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940090961 chromium dioxide Drugs 0.000 description 1
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 1
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 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
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
- C07C209/56—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from carboxylic acids involving a Hofmann, Curtius, Schmidt, or Lossen-type rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63141822A JPH021432A (ja) | 1988-06-10 | 1988-06-10 | ２，２‐ビス（４‐アミノフェニル）ヘキサフルオロプロパンの製造法 |
| US07/360,981 US4987259A (en) | 1988-06-10 | 1989-06-02 | Process of preparing 2,2-bis(4-aminophenyl)-hexafluoropropane |
| DE3918792A DE3918792A1 (de) | 1988-06-10 | 1989-06-08 | Verfahren zur herstellung von 2,2-bis-(4-aminophenyl)-hexafluorpropan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63141822A JPH021432A (ja) | 1988-06-10 | 1988-06-10 | ２，２‐ビス（４‐アミノフェニル）ヘキサフルオロプロパンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH021432A true JPH021432A (ja) | 1990-01-05 |
| JPH0517218B2 JPH0517218B2 (en, 2012) | 1993-03-08 |
Family
ID=15300933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63141822A Granted JPH021432A (ja) | 1988-06-10 | 1988-06-10 | ２，２‐ビス（４‐アミノフェニル）ヘキサフルオロプロパンの製造法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4987259A (en, 2012) |
| JP (1) | JPH021432A (en, 2012) |
| DE (1) | DE3918792A1 (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9554834B2 (en) | 2006-08-17 | 2017-01-31 | DePuy Synthes Products, Inc. | Push-off driver and method for inserting bone screws |
| US11814360B2 (en) | 2017-10-05 | 2023-11-14 | Novomer, Inc. | Isocyanates, derivatives, and processes for producing the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19517725A1 (de) * | 1995-05-15 | 1996-11-21 | Bayer Ag | Verfahren zur Herstellung von 2-Fluorcyclopropylamin-sulfonsäuresalzen und die chemische Verbindung 2-Fluorcyclopropylisocyanat |
| CN107955166B (zh) * | 2017-11-27 | 2020-05-19 | 中国科学院长春应用化学研究所 | 一种氰酸酯树脂及其制备方法、复合材料 |
| CN112624930A (zh) * | 2020-12-21 | 2021-04-09 | 上海如鲲新材料有限公司 | 一种2,2-双（4-氨基苯基）六氟丙烷的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3310573A (en) * | 1963-06-17 | 1967-03-21 | Du Pont | Diaryl fluoro compounds |
| US4370501A (en) * | 1981-10-05 | 1983-01-25 | Hughes Aircraft Company | Synthesis of bis(aminophenyl) compounds |
-
1988
- 1988-06-10 JP JP63141822A patent/JPH021432A/ja active Granted
-
1989
- 1989-06-02 US US07/360,981 patent/US4987259A/en not_active Expired - Lifetime
- 1989-06-08 DE DE3918792A patent/DE3918792A1/de active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9554834B2 (en) | 2006-08-17 | 2017-01-31 | DePuy Synthes Products, Inc. | Push-off driver and method for inserting bone screws |
| US11814360B2 (en) | 2017-10-05 | 2023-11-14 | Novomer, Inc. | Isocyanates, derivatives, and processes for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3918792A1 (de) | 1989-12-14 |
| DE3918792C2 (en, 2012) | 1991-05-23 |
| US4987259A (en) | 1991-01-22 |
| JPH0517218B2 (en, 2012) | 1993-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |