DE1768005C - Process for the production of ethylbenzene by thermal cleavage of dibenzyl - Google Patents
Process for the production of ethylbenzene by thermal cleavage of dibenzylInfo
- Publication number
- DE1768005C DE1768005C DE19681768005 DE1768005A DE1768005C DE 1768005 C DE1768005 C DE 1768005C DE 19681768005 DE19681768005 DE 19681768005 DE 1768005 A DE1768005 A DE 1768005A DE 1768005 C DE1768005 C DE 1768005C
- Authority
- DE
- Germany
- Prior art keywords
- dibenzyi
- ethylbenzene
- cleavage
- zone
- hydrocarbon
- 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
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims description 15
- QWUWMCYKGHVNAV-UHFFFAOYSA-N Bibenzyl Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 title claims description 9
- 238000003776 cleavage reaction Methods 0.000 title claims 14
- 238000004519 manufacturing process Methods 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 9
- 239000004215 Carbon black (E152) Substances 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 8
- 150000002430 hydrocarbons Chemical class 0.000 claims 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003849 aromatic solvent Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 230000003197 catalytic Effects 0.000 claims 2
- 238000010494 dissociation reaction Methods 0.000 claims 2
- 230000005593 dissociations Effects 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 230000002152 alkylating Effects 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 238000005336 cracking Methods 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 230000004992 fission Effects 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Description
Das nachfolgende Beispiel dient der Erläuterung des Verfahrens gemäß der Erfindung.The following example serves to explain the method according to the invention.
Es wurden mehrere Versuche zur thermischen Spaltung von Dibenzyl in Gegenwart von Wasserstoff durchgeführt. Bei jedem Versuch wurde eine Lösung, weiche aus Dibenzyl und Toluol im Verhältnis von 2 Mol Toluol je Mol Dibenzyl bestand, in einen beheizten Reaktor zusammen mit 21 Mol Wasserstoff je MoI Dibenzyl gepumpt. Der beheizte Reaktor wurde bei jedem Versuch auf einen Druck von etwa 49,2 kg/ cm2 gehalten. Der Zustrom zum Reaktor wurde so einrefeuliert, daß eine effektive Verweilzeit der Reaktanten im Reaktor von etwa 12 Sekunden erreicht wurde. Aus der folgenden Tabelle sind die bei jedem Versuch angewendete Temperatur und die dabei erzielten Umsetzungen und Ausbeuten ersichtlich. Die Umsetzung ist dabei als der Prozentsatz des dem Reaktor zugeführten und in irgendein anderes Produkt umgesetztes Dibenzyl definiert. Die Ausbeute ist in Prozent des theoretischen Wertes ausgedrückt, welcher ein MoI Äthylbenzol je Mol umgesetztes Dibenzyl ist.Several attempts have been made to thermally cleave dibenzyl in the presence of hydrogen. In each experiment, a solution consisting of dibenzyl and toluene in a ratio of 2 moles of toluene per mole of dibenzyl was pumped into a heated reactor together with 21 moles of hydrogen per mole of dibenzyl. The heated reactor was maintained at a pressure of about 49.2 kg / cm 2 for each experiment. The flow to the reactor was adjusted so that an effective residence time of the reactants in the reactor of about 12 seconds was achieved. The following table shows the temperature used in each experiment and the conversions and yields achieved. The conversion is defined as the percentage of the dibenzyl fed to the reactor and converted into some other product. The yield is expressed as a percentage of the theoretical value, which is one mole of ethylbenzene per mole of dibenzyl converted.
Claims (3)
neuen Herstellungsverfahren für Äthylbenzol gesucht. Die zur Durchführung des Verfahrens gemäß derThe demand for styrene is constantly growing. 35 Dibenzyi fed to the cleavage zone at least partially The entire amount of the styrene currently produced is dissolved in a hydrocarbon solvent. practically comes from the dehydrogenation of Ethyoi- The hydrocarbon solvent can be benzene. A large part of the ethylbenzene used in styrene production can be either aromatic or non-aromatic, whereby the ethylbenzene used is obtained by alkylating, however, the aromatic solvents, preferably benzene, with ethylene. Turned 40 in the last few years. Particularly preferred are the mononuclear ones, ethylbenzene is increasingly also obtained in the case of aromatic solvents such as benzene, toluene or fractionation of petroleum. Furthermore, xylene. It is understandable that the hydrocarbon has recently been using dibenzyi as a starting material for the solvent from mixtures of various modifications of alkylbenzenes. This is how connections can exist. The amount of solvent used for the catalytic cleavage of Dibenzyi only needs to be so large that toluene has become known. In the USA patent the dibenzyi is partially solved. However, a catalytic method is also preferred so that the dibenzyi is completely dissolved. If the cleavage of Dibenzyi to toluene and ethylbenzene is used as a solvent, then it is written, but with considerably more Toluc! is obtained as an amount depending on the type of solvent in the general ethylbenzene. However, since the demand 5 ° mean between 0.5 to 5.0 moles per mole of Dibenzyi. for styrene and thus in turn the demand for preferred is the use of about 1 to 3 moles of ethylbenzene increases from year to year, according to hydrocarbon solvent per mole of dibenzene.
wanted new manufacturing process for ethylbenzene. To carry out the procedure according to
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62498867 | 1967-03-22 | ||
US624988A US3373217A (en) | 1967-03-22 | 1967-03-22 | Hydrogenolysis of sym-diphenylethane to ethylbenzene |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1768005A1 DE1768005A1 (en) | 1972-01-13 |
DE1768005C true DE1768005C (en) | 1973-05-24 |
Family
ID=
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