DE1251334B - - Google Patents
Info
- Publication number
- DE1251334B DE1251334B DENDAT1251334D DE1251334DA DE1251334B DE 1251334 B DE1251334 B DE 1251334B DE NDAT1251334 D DENDAT1251334 D DE NDAT1251334D DE 1251334D A DE1251334D A DE 1251334DA DE 1251334 B DE1251334 B DE 1251334B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyphenyl
- general formula
- aniline
- reaction
- hours
- 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
- -1 (hydroxyphenyl) - (aminophenyl) alkanes Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- JFQDFSBPECPOTA-UHFFFAOYSA-N 4-[2-(4-amino-3-chlorophenyl)propan-2-yl]phenol Chemical compound C=1C=C(N)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C=C1 JFQDFSBPECPOTA-UHFFFAOYSA-N 0.000 description 1
- FXINQDMORBLWNE-UHFFFAOYSA-N 4-[2-(4-amino-3-methylphenyl)propan-2-yl]phenol Chemical compound C1=C(N)C(C)=CC(C(C)(C)C=2C=CC(O)=CC=2)=C1 FXINQDMORBLWNE-UHFFFAOYSA-N 0.000 description 1
- NFGPNZVXBBBZNF-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(N)C=C1 NFGPNZVXBBBZNF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- QVLMUEOXQBUPAH-UHFFFAOYSA-N stilben-4-ol Chemical compound C1=CC(O)=CC=C1C=CC1=CC=CC=C1 QVLMUEOXQBUPAH-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER0040130 | 1965-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1251334B true DE1251334B (enrdf_load_stackoverflow) | 1967-10-05 |
Family
ID=7405978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1251334D Pending DE1251334B (enrdf_load_stackoverflow) | 1965-03-16 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1251334B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374272A (en) * | 1978-11-08 | 1983-02-15 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 2-(4'-hydroxyaryl)-2-(4'-aminoaryl)-propanes |
| US4400521A (en) * | 1980-10-29 | 1983-08-23 | Mitsui Toatsu Chemicals, Incorporated | N-Substituted phenyl maleimides |
-
0
- DE DENDAT1251334D patent/DE1251334B/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374272A (en) * | 1978-11-08 | 1983-02-15 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 2-(4'-hydroxyaryl)-2-(4'-aminoaryl)-propanes |
| US4400521A (en) * | 1980-10-29 | 1983-08-23 | Mitsui Toatsu Chemicals, Incorporated | N-Substituted phenyl maleimides |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2855764C2 (enrdf_load_stackoverflow) | ||
| DE1251334B (enrdf_load_stackoverflow) | ||
| DE1266309B (de) | Verfahren zur Herstellung von Bromderivaten von Bis-(hydroxyphenyl)-dialkylmethanen | |
| DE2007535A1 (de) | Verfahren zur Herstellung von Triarylphosphinen | |
| DE2856384C3 (de) | Quartäre Ammoniumgruppen enthaltende Acrylyl- bzw. Methacrylylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE2503699A1 (de) | Verfahren zur herstellung von 1,2- benzisothiazolen | |
| EP0173202B1 (de) | Verfahren zur Herstellung von Chlor-o-nitroanilinen | |
| DE3210419A1 (de) | Verfahren zur herstellung von derivaten der vinylphosphon- oder vinylpyrophosphonsaeure | |
| DE932010C (de) | Verfahren zur Herstellung von N-Aryl-alkylendiaminen | |
| DE934890C (de) | Verfahren zur Herstellung von basischen Benzhydrylaethern | |
| DE3605197A1 (de) | Verfahren zur herstellung von 4-nitrodiphenylaminen | |
| CH660491A5 (de) | Verfahren zur herstellung von triarylmethanverbindungen. | |
| DE3504073C2 (enrdf_load_stackoverflow) | ||
| EP0003052B1 (de) | Verfahren zur Herstellung von 4-Methyl-5-chlormethylimidazol | |
| DE2521649C2 (de) | 3-Amino-4-carbalkoxybenzoesäure- 4'-phenoxyanilide, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE887198C (de) | Verfahren zur Herstellung von Naphthostyrilen | |
| DE2653601A1 (de) | Perfluoralkylgruppen enthaltende hydroxyketone | |
| DE19705466A1 (de) | Verfahren zur Herstellung von N-Alkylcarbazolen | |
| DE2509262C3 (de) | Verfahren zum Herstellen eines 5-Alkyliden-2-norbornens durch Isomerisieren eines 5-Alkenyl-2-norbornens | |
| DE2544504C2 (de) | Verfahren zur Herstellung von Diarylaminen | |
| DE1176666B (de) | Verfahren zur Herstellung von (4-Hydroxy-phenyl)-(4'-aminophenyl)-alkenen und deren Substitutionsprodukten | |
| EP0101996B1 (de) | Verfahren zur Herstellung von E-Isomeren von 1-Cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-on-Derivaten | |
| AT353791B (de) | Verfahren zur herstellung des maleinsaeuresalzes von 2-phenyl-6-(1-hydroxy -2-tert.-butylaminoaethyl)-4h-pyrido-(3,2-d)-1, 3-dioxin | |
| DE1178052B (de) | Verfahren zur Herstellung von heterocyclischen Verbindungne, die mindestens ein einem Ringstickstoffatom benachbartes Chloratom enthalten. | |
| AT268256B (de) | Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 2-Alkoxy-5-halogenbenzoesäureestern |