DE1518917C - - Google Patents
Info
- Publication number
- DE1518917C DE1518917C DE1518917C DE 1518917 C DE1518917 C DE 1518917C DE 1518917 C DE1518917 C DE 1518917C
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- dimethyl
- alcl
- diisopropylbenzene
- catalyst
- 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 29
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 26
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 22
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 17
- 239000008096 xylene Substances 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- MBEBPYJMHLBHDJ-UHFFFAOYSA-N 1,4-dimethyl-2,5-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C)=C(C(C)C)C=C1C MBEBPYJMHLBHDJ-UHFFFAOYSA-N 0.000 claims description 9
- PUPZFBLFGPJICA-UHFFFAOYSA-N 1,5-dimethyl-2,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(C)C=C1C PUPZFBLFGPJICA-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229910015900 BF3 Inorganic materials 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- AADQFNAACHHRLT-UHFFFAOYSA-N 2,4-Dimethyl-1-(1-methylethyl)-benzene Chemical compound CC(C)C1=CC=C(C)C=C1C AADQFNAACHHRLT-UHFFFAOYSA-N 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- CLSBTDGUHSQYTO-UHFFFAOYSA-N 1,4-dimethyl-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC(C)=CC=C1C CLSBTDGUHSQYTO-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CRERPVSNPBKHJB-UHFFFAOYSA-N 1,2-dimethyl-3,4-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=C(C)C(C)=C1C(C)C CRERPVSNPBKHJB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- RMKJTYPFCFNTGQ-UHFFFAOYSA-N 1,3-dimethyl-5-propan-2-ylbenzene Chemical compound CC(C)C1=CC(C)=CC(C)=C1 RMKJTYPFCFNTGQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000006207 propylation Effects 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- GDEQPEBFOWYWSA-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-ylbenzene Chemical class CC(C)C1=CC=CC(C)=C1C GDEQPEBFOWYWSA-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- DWCUSFKFZPWXNF-UHFFFAOYSA-N prop-1-ene 1,4-xylene Chemical group C1(=CC=C(C=C1)C)C.C=CC DWCUSFKFZPWXNF-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE112007003012T5 (de) | Alkylierungsverfahren unter Verwendung eines mit Alkyhalogenid arbeitenden Ionenflüssigkeitskatalysators | |
| DE10008924A1 (de) | Verfahren zur Herstellung von Phenol | |
| DE2745589C3 (de) | Verfahren zur Herstellung von p-Alkylphenolen | |
| DE1518917C (enExample) | ||
| DE2445797B2 (de) | Verfahren zur kontinuierlichen Herstellung von Äthylbenzol durch Alkylieren von Benzol mit Äthylen | |
| DE4107242A1 (de) | Verfahren zur herstellung von 9,9-bis-(4-hydroxyphenyl-)fluoren | |
| DE1443421A1 (de) | Verfahren zur Herstellung alkylierter aromatischer Verbindungen | |
| DE1518917B1 (de) | Verfahren zur Herstellung von 1,3-Dimethyl-4,6-diisopropylbenzol und 1,4-Dimethyl-2,5-diisopropylbenzol | |
| DE2547839B2 (de) | Verfahren zur Alkylierung von C4 -C6 -Isoparaffinen mit C3 -Cj -Olefinen in Gegenwart von Säuren als Katalysator | |
| DE68905714T2 (de) | Verfahren zur chloroethylierung von aromatischen kohlenwasserstoffen. | |
| DE2242628A1 (de) | Verfahren zur herstellung von 5-isopropyl-3-methyl-phenol | |
| EP0736507B1 (de) | Verfahren zur Alkylierung und Transalkylierung von Aromaten | |
| EP0438641A2 (de) | Verfahren zur Herstellung von 2,6-Di-tert.butylphenol | |
| DE1668473B1 (de) | Verfahren zum Herstellen von Alkylarylverbindungen | |
| DE2448231C2 (de) | Verfahren zur Herstellung von Alkylnaphthalinen | |
| DE638756C (enExample) | ||
| AT227680B (de) | Verfahren zur Herstellung von Alkylphenolen | |
| DE1162823B (de) | Verfahren zur Herstellung von Alkylchloriden mit einem Molekulargewicht zwischen 300 und 500 | |
| EP0564979B1 (de) | Verfahren zur Herstellung von Dixylylpropan | |
| DE3028199C2 (de) | Verfahren zur Isomerisierung von 1-Methylnaphthalin | |
| DE1568682C (enExample) | ||
| DE2024604C (enExample) | ||
| DE1247286B (de) | Verfahren zur Alkylierung von Cumol bzw. Benzol mit Propen ueber Aluminiumchlorid | |
| DE1093340B (de) | Verfahren zur Herstellung alkylierter aromatischer Kohlenwasserstoffe | |
| DD269619A1 (de) | Verfahren zur herstellung von 5-alkyl- und 3,5-dialkylsalicylsaeuren und deren derivaten |