Process for producing cyclohexylbenzene

Patent metadata

Field	Value
Publication number	US-9458067-B2
Application number	US-201314373690-A
Country	US
Kind code	B2
Filing date	Jan 28, 2013
Priority date	Feb 8, 2012
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

In a process for producing cyclohexylbenzene, hydrogen and benzene are introduced to a first hydroalkylation reaction zone which contains a hydroalkylation catalyst and which is operated under at least partly liquid phase conditions sufficient to effect hydroalkylation of benzene to produce a mixed liquid/vapor phase effluent comprising cyclohexylbenzene and unreacted benzene, wherein at least a portion of the unreacted benzene is in the vapor phase. At least a portion of the effluent is cooled to condense a liquid phase stream containing at least some of the cyclohexylbenzene in the effluent portion and leave a residual stream containing at least some of the unreacted benzene and cyclohexylbenzene. At least a portion of the liquid stream is recycled to the first hydroalkylation reaction zone or to contact the mixed phase effluent exiting the first hydroalkylation reaction zone. Other methods of cooling the reaction effluent are disclosed.

First claim

The invention claimed is:

1. A process for producing cyclohexylbenzene comprising:
(a) introducing hydrogen and benzene to a first hydroalkylation reaction zone containing a hydroalkylation catalyst;
(b) operating said first hydroalkylation reaction zone under at least partly liquid phase conditions sufficient to effect hydroalkylation of at least a portion of the benzene in the presence of said hydroalkylation catalyst to produce a first mixture exiting the first reaction zone comprising a liquid phase and a vapor phase, wherein the first mixture comprises cyclohexylbenzene and unreacted benzene;
(c) separating the first mixture into a first liquid effluent comprising cyclohexylbenzene and a portion of the unreacted benzene and a first vapor effluent comprising at least a portion of the unreacted benzene;
(d) cooling at least a portion of the first vapor effluent to obtain a second liquid effluent containing at least a portion of the unreacted benzene; and
(e) recycling at least a portion of the second liquid phase stream to the first hydroalkylation reaction zone or to contact the first mixture or to mix with the first liquid effluent.

2. The process of claim 1 , wherein the benzene contained in the second liquid effluent is at least 1 wt % of the total weight of the first mixture.

3. The process of claim 1 , wherein the benzene contained in the first liquid effluent is at least 3 wt % of the total weight of the first mixture.

4. The process of claim 1 , wherein the benzene contained in the first liquid effluent is at least 10 wt % of the total weight of the first mixture.

5. The process of claim 1 , further comprising:
(f) introducing at least a portion of the first liquid effluent and additional hydrogen to a second hydroalkylation reaction zone containing a hydroalkylation catalyst and connected in series with the first hydroalkylation reaction zone; and
(g) operating said second hydroalkylation reaction zone under at least partly liquid phase conditions sufficient to effect hydroalkylation of at least a portion of the unreacted benzene in the first liquid effluent in the presence of said hydroalkylation catalyst to produce a third liquid effluent comprising cyclohexylbenzene.

6. The process of claim 1 , wherein the cooling (d) is effected by passing the portion of the first vapor effluent through a heat exchanger, and the heat exchanger supplies heat to one of (i) a reboiler for a benzene distillation column and (ii) a dehydrogenation feed to a dehydrogenation reactor for converting cyclohexane produced as a byproduct of the operating step (b) to benzene.

7. The process of claim 5 , wherein each of said operating steps (b) and (g) is conducted at a temperature of about 100° C. to about 250° C. and a pressure of about 100 kPa to about 7,000 kPa.

8. The process of claim 1 , wherein the hydroalkylation catalyst comprises at least one molecular sieve and at least one hydrogenation metal.

9. A process for producing cyclohexylbenzene comprising:
(a) introducing hydrogen and benzene to a first hydroalkylation reaction zone containing a hydroalkylation catalyst;
(b) operating said first hydroalkylation reaction zone under at least partly liquid phase conditions sufficient to effect hydroalkylation of benzene in the presence of said hydroalkylation catalyst to produce a mixed liquid/vapor phase first effluent comprising cyclohexylbenzene and unreacted hydrogen and benzene, wherein at least a portion of the unreacted benzene is in the vapor phase;
(c) removing said mixed phase first effluent from said first hydroalkylation reaction zone;
(d) cooling at least a portion of the mixed phase first effluent removed from said first hydroalkylation reaction zone by heat exchange so as to supply heat to one of (i) a reboiler for a benzene distillation column and (ii) a dehydrogenation feed to a dehydrogenation reactor for converting cyclohexane produced as a byproduct of the operating steps (b) and (f) to benzene;
(e) introducing at least a portion of the cooled mixed phase first effluent to a second hydroalkylation reaction zone containing a hydroalkylation catalyst and connected in series with the first hydroalkylation reaction zone; and
(f) operating said second hydroalkylation reaction zone under at least partly liquid phase conditions sufficient to effect hydroalkylation of unreacted benzene in mixed phase first effluent in the presence of said hydroalkylation catalyst to produce a second effluent comprising cyclohexylbenzene.

10. The process of claim 9 , wherein each of said operating steps (b) and (f) is conducted at a temperature of about 125° C. to about 250° C. and a pressure of about 100 kPa to about 7,000 kPa.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Becker Christopher L
• Nair Hari
• Lattner James R
• Kuechler Keith H

Classifications

• C07C2529/08

  of the faujasite type, e.g. type X or Y · CPC title

• C07C409/14

  the carbon atom belonging to a ring other than a six-membered aromatic ring · CPC title

• C07C45/53

  of hydroperoxides · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C5/367

  Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene · CPC title