DE1543335C - - Google Patents
Info
- Publication number
- DE1543335C DE1543335C DE1543335C DE 1543335 C DE1543335 C DE 1543335C DE 1543335 C DE1543335 C DE 1543335C
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- phenyl
- catalyst
- oxide
- mixture
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 8
- 125000005266 diarylamine group Chemical group 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 16
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- 235000005074 zinc chloride Nutrition 0.000 description 8
- 239000011592 zinc chloride Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- -1 ethylphenyl Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CMQZETQFZHIYJG-UHFFFAOYSA-N 2-(n-phenylanilino)ethanol Chemical compound C=1C=CC=CC=1N(CCO)C1=CC=CC=C1 CMQZETQFZHIYJG-UHFFFAOYSA-N 0.000 description 1
- AMYFDYWNSRVOOV-UHFFFAOYSA-N 2-(n-phenylanilino)propan-1-ol Chemical compound C=1C=CC=CC=1N(C(CO)C)C1=CC=CC=C1 AMYFDYWNSRVOOV-UHFFFAOYSA-N 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- IOXYAALIVGXTGR-UHFFFAOYSA-N 2-amino-3-naphthalen-1-ylpropan-1-ol Chemical compound C1=CC=C2C(CC(CO)N)=CC=CC2=C1 IOXYAALIVGXTGR-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69008606T2 (de) | Verfahren zur Herstellung von Carbamaten. | |
| DE1051271B (de) | Verfahren zur Herstellung von kernalkylierten aromatischen Aminen | |
| EP0257443A1 (de) | Verfahren zur Herstellung von Trialkylaminen | |
| DE1543335C (enrdf_load_stackoverflow) | ||
| DE2945614C2 (enrdf_load_stackoverflow) | ||
| DE1543335B1 (de) | Verfahren zur Herstellung von N,N-Diarylaminoalkanolen | |
| DE2605212B2 (de) | Verfahren zur Herstellung von Polypropylenpolyaminen | |
| EP0292674B1 (de) | Verfahren zur Herstellung von Propinol | |
| DE2329923C3 (de) | Verfahren zur Herstellung von 5-Oxohexannitri! | |
| EP0901456B1 (de) | Verfahren zur herstellung von 2-fluor-1-cyclopropancarbonsäurederivaten durch reduktive enthalogenierung | |
| EP0042568B1 (de) | Verfahren zur Herstellung von 2,6-Xylidin | |
| DE2648644A1 (de) | Verfahren zur herstellung von 4-phenoxy-phenolen | |
| DE2732227A1 (de) | Verfahren zur herstellung aromatischer aldehyde | |
| EP0422534B1 (de) | Verfahren zur Herstellung von N-Alkyl-und N,N-Dialkyl-diaminoethanen | |
| DE2732409A1 (de) | Verfahren zur herstellung von diaminoalkoxybenzolen | |
| DE1768321C3 (enrdf_load_stackoverflow) | ||
| DE2544504C2 (de) | Verfahren zur Herstellung von Diarylaminen | |
| DE1468923C (de) | ,at 07.07.65 ot 06.02.69 bt 02.04.70 | |
| DE2358355C3 (de) | Verfahren zur Herstellung von 1,3-Dlamino-2,2-dimethylpropan | |
| AT232984B (de) | Verfahren zur katalytischen Di- bzw. Trimerisation von 1, 3-Diolefinen | |
| DE1168413B (de) | Verfahren zur Herstellung von Monomethylestermonoamiden carbocyclischer, aromatischer Dicarbonsaeuren | |
| DE1443666C3 (de) | Verfahren zur Herstellung von Alkoholen | |
| EP0492473A1 (de) | Verfahren zur Herstellung von 4-substituierten 2,6-Dialkylanilinen | |
| DE2006958A1 (en) | Simultaneous isopropanol and methyl ethylketone prepn | |
| DE1277235B (de) | Verfahren zur Herstellung von 3-Ketobutanol-(1) |