Process for making phenol and/or cyclohexanone

Patent metadata

Field	Value
Publication number	US-9908829-B2
Application number	US-201415038975-A
Country	US
Kind code	B2
Filing date	Nov 14, 2014
Priority date	Dec 20, 2013
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

Disclosed is (i) a process of making phenol and/or cyclohexanone from cyclohexylbenzene including a step of removing methylcyclopentylbenzene from (a) the cyclohexylbenzene feed supplied to the oxidation step and/or (b) the crude phenol product (ii) a phenol composition and (iii) a cyclohexylbenzene composition that can be made using the process.

First claim

The invention claimed is:

1. A process for making phenol and/or cyclohexanone, the process comprising:
(I) providing a first mixture comprising cyclohexylbenzene and methylcyclopentylbenzene, wherein the first mixture comprises methylcyclopentylbenzene at a concentration in a range from 100 ppm to 5.0 wt %, based on the total weight of the first mixture, and wherein the first mixture comprises trans-1-methyl-2-phenylcyclopentane at a concentration in a range from 100 ppm to 4.5 wt %, based on the total weight of the first mixture;
(II) removing at least a portion of the methylcyclopentylbenzene from the first mixture to obtain a second mixture comprising cyclohexylbenzene, wherein the second mixture comprises methylcyclopentylbenzene at a concentration in a range from 0 ppm to 2000 ppm, based on the total weight of the second mixture;
(III) oxidizing at least a portion of the cyclohexylbenzene in the second mixture in an oxidation reactor under oxidation conditions to obtain a third mixture comprising cyclohexylbenzene hydroperoxide and cyclohexylbenzene; and
(IV) reacting at least a portion of the third mixture in a cleavage reactor under cleavage reaction conditions to obtain a cleavage product mixture comprising cyclohexylbenzene, phenol and cyclohexanone.

2. The process of claim 1 , wherein the cleavage product mixture comprises trans-1-methyl-2-phenylcyclopentane at a concentration in a range from 100 ppb to 2000 ppm, based on the total weight of the cleavage product mixture.

3. The process of claim 1 , wherein step (I) comprises:
(Ia) contacting benzene with hydrogen in the presence of a hydroalkylation catalyst under hydroalkylation conditions to obtain a hydroalkylation product mixture; and
(Ib) separating the hydroalkylation product mixture to obtain a fraction comprising cyclohexylbenzene and methylcyclopentylbenzene as the first mixture.

4. The process of claim 1 , further comprising the following steps:
(IIIa) obtaining a fourth mixture comprising at least 80 wt % of cyclohexylbenzene and a fifth mixture comprising cyclohexylbenzene hydroperoxide at a concentration higher than the third mixture; and
(IIIb) feeding the fifth mixture to the cleavage reactor as a portion of the third mixture.

5. The process of claim 4 , wherein at least a portion of the fourth mixture is recycled to step (I) as at least a portion of the first mixture.

6. The process of claim 1 , further comprising:
(V) separating the cleavage product mixture to obtain a cyclohexylbenzene fraction, a phenol fraction and a cyclohexanone fraction.

7. The process of claim 6 , wherein the phenol fraction comprises methylcyclopentylbenzene at a concentration in a range from 50 ppb to 1000 ppm, based on the total weight of the phenol fraction, and the process further comprises:
(VI) removing at least a portion of the methylcyclopentylbenzene from the phenol fraction.

8. The process of claim 7 , wherein the phenol fraction comprises trans-1-methyl-2-phenylcyclopentane at a concentration in a range from 50 ppb to 750 ppm, based on the total weight of the phenol fraction.

9. The process of claim 7 , wherein in step (VI), a purified phenol product comprising methylcyclopentylbenzene at a concentration below 1 ppm, based on the total weight of the purified phenol product, is obtained, further wherein the purified phenol product comprises trans-1-methyl-2-phenylcyclopentane at a concentration lower than 950 ppb, based on the total weight of the purified phenol product.

10. The process of claim 7 , wherein step (VI) comprises:
(VIa) distilling the phenol fraction in the presence of an extractive solvent to obtain a fraction comprising phenol and essentially free of the extractive solvent, and a fraction comprising a mixture of methylcyclopentylbenzene and the extractive solvent.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Davis Jason D
• Poucher Ashley J
• Weber Joerg F W
• Watts Jonathan J
• Becker Christopher L

Classifications

• C07C37/08 Primary

  by decomposition of hydroperoxides, e.g. cumene hydroperoxide · CPC title

• C07C2/74

  by addition with simultaneous hydrogenation · CPC title

• C07C37/80

  by extractive distillation · CPC title

• C07C45/53

  of hydroperoxides · CPC title

• C07C2601/14

  The ring being saturated · CPC title