JPH0475222B2 - - Google Patents
Info
- Publication number
- JPH0475222B2 JPH0475222B2 JP11889684A JP11889684A JPH0475222B2 JP H0475222 B2 JPH0475222 B2 JP H0475222B2 JP 11889684 A JP11889684 A JP 11889684A JP 11889684 A JP11889684 A JP 11889684A JP H0475222 B2 JPH0475222 B2 JP H0475222B2
- Authority
- JP
- Japan
- Prior art keywords
- aminocumyl
- bis
- group
- benzene
- reaction
- 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
- GMXDGTTWWKYVPR-UHFFFAOYSA-N 4-[2-[2-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC=C(C(C)(C)C=2C=CC(N)=CC=2)C=1C(C)(C)C1=CC=C(N)C=C1 GMXDGTTWWKYVPR-UHFFFAOYSA-N 0.000 claims description 11
- 150000001448 anilines Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 description 10
- -1 o-aminocumyl-p-aminocumylbenzenes Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- HESXPOICBNWMPI-UHFFFAOYSA-N 4-[2-[4-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(N)=CC=2)C=CC=1C(C)(C)C1=CC=C(N)C=C1 HESXPOICBNWMPI-UHFFFAOYSA-N 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004445 quantitative analysis Methods 0.000 description 4
- CUZMSUQFXDTNQE-UHFFFAOYSA-N 2-[2-[3-[2-(2-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC=C(N)C=1C(C)(C)C(C=1)=CC=CC=1C(C)(C)C1=CC=CC=C1N CUZMSUQFXDTNQE-UHFFFAOYSA-N 0.000 description 3
- KWOIWTRRPFHBSI-UHFFFAOYSA-N 4-[2-[3-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC(C(C)(C)C=2C=CC(N)=CC=2)=CC=1C(C)(C)C1=CC=C(N)C=C1 KWOIWTRRPFHBSI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MNLFTVQGBPIASX-UHFFFAOYSA-N NC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)N Chemical class NC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)N MNLFTVQGBPIASX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 1
- RUQRVBCRURWOHS-UHFFFAOYSA-N 2,4-dimethyl-3-phenylpentane-2,4-diol Chemical compound CC(C)(O)C(C(C)(C)O)C1=CC=CC=C1 RUQRVBCRURWOHS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- UKXWHVXNLXNBMV-UHFFFAOYSA-N 2-[2-(1-amino-2-phenylpropan-2-yl)phenyl]-2-phenylpropan-1-amine Chemical class NCC(C)(C1=CC=CC=C1)C1=C(C=CC=C1)C(CN)(C)C1=CC=CC=C1 UKXWHVXNLXNBMV-UHFFFAOYSA-N 0.000 description 1
- KSMBFKMHJGVFQO-UHFFFAOYSA-N 2-[2-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1C(C)(C)O KSMBFKMHJGVFQO-UHFFFAOYSA-N 0.000 description 1
- SDKYDUUJVBRYEK-UHFFFAOYSA-N 2-[2-[3-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound NC1=C(C(C)(C)C2=CC(=CC=C2)C(C)(C)C2=CC=C(C=C2)N)C=CC=C1 SDKYDUUJVBRYEK-UHFFFAOYSA-N 0.000 description 1
- UGPWRRVOLLMHSC-UHFFFAOYSA-N 2-[3-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C(C)(C)O)=C1 UGPWRRVOLLMHSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 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
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000011964 heteropoly acid Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11889684A JPS6144A (ja) | 1984-06-08 | 1984-06-08 | ビス（ｐ−アミノクミル）ベンゼン類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11889684A JPS6144A (ja) | 1984-06-08 | 1984-06-08 | ビス（ｐ−アミノクミル）ベンゼン類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6144A JPS6144A (ja) | 1986-01-06 |
| JPH0475222B2 true JPH0475222B2 (enrdf_load_stackoverflow) | 1992-11-30 |
Family
ID=14747839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11889684A Granted JPS6144A (ja) | 1984-06-08 | 1984-06-08 | ビス（ｐ−アミノクミル）ベンゼン類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6144A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973754A (en) * | 1989-05-15 | 1990-11-27 | Shell Oil Company | Preparation of bis(p-aminocumyl)benzenes |
| WO1993012933A1 (en) * | 1991-12-27 | 1993-07-08 | Sumitomo Chemical Company, Limited | Polyamino-oligomer and polymaleimide compound |
| KR102761584B1 (ko) * | 2018-09-12 | 2025-02-03 | 니폰 가야꾸 가부시끼가이샤 | 말레이미드 수지, 경화성 수지 조성물 및 그 경화물 |
| KR102727867B1 (ko) * | 2020-03-11 | 2024-11-07 | 닛뽄 가야쿠 가부시키가이샤 | 말레이미드 수지 및 그의 제조 방법, 말레이미드 용액, 그리고, 경화성 수지 조성물 및 그의 경화물 |
| CN113480439A (zh) * | 2021-07-21 | 2021-10-08 | 江西同宇新材料有限公司 | 一种含异丙叉烷烃结构的氨基酚的制备方法 |
-
1984
- 1984-06-08 JP JP11889684A patent/JPS6144A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6144A (ja) | 1986-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |