Cyclohexylbenzene composition

Patent metadata

Field	Value
Publication number	US-10259759-B2
Application number	US-201415038983-A
Country	US
Kind code	B2
Filing date	Nov 14, 2014
Priority date	Dec 20, 2013
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

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 cyclohexylbenzene composition comprising cyclohexylbenzene at a concentration of C(CHB) wt % and methylcyclopentylbenzene at a concentration of C(MCPB) ppm, where the percentage and ppm are based on the total weight of the cyclohexylbenzene composition, C(CHB)≥95.00, and 0.001≤C(MCPB)≤5000, wherein the methylcyclopentylbenzene comprises (a) cis-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2cis) ppm and (b) trans-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2trans) ppm, and C(MCPB2trans)≤C(MCPB2cis); the composition obtained by the process comprising:
(I) providing a first mixture comprising cyclohexylbenzene and methylcyclopentylbenzene;
(II) removing at least a portion of the methylcyclopentylbenzene from the first mixture to obtain a second mixture comprising cyclohexylbenzene;
(III) oxidizing at least a portion of the cyclohexylbenzene in the second mixture in an oxidation reactor under oxidation conditions to obtain a cleavage feed comprising cyclohexylbenzene hydroperoxide and cyclohexylbenzene; and
(IV) reacting the cleavage feed in a cleavage reactor under cleavage reaction conditions to obtain a cleavage product mixture comprising cyclohexylbenzene, phenol and cyclohexanone.

2. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises (a) cis-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2cis) ppm and (b) trans-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2trans) ppm, and at least one of the following conditions (i), (ii), and (iii) is met:
(i) 0.001≤C(MCPB2cis)≤4500;
(ii) 0.001≤C(MCPB2trans)≤4500; and
(iii) 0.001≤C(MCPB2cis)+C(MCPB2trans)≤4500.

3. The cyclohexylbenzene composition of claim 1 , wherein 0.010≤C(MCPB)≤1000.

4. The cyclohexylbenzene composition of claim 1 , wherein 1.5≤C(MCPB2cis)/C(MCPB2trans)≤1000.

5. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises (a) cis-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2cis) ppm; (b) trans-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2trans) ppm; (c) cis-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3cis) ppm; and (d) trans-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3trans) ppm, and at least one of the following conditions (i), (ii), (iii), and (iv) is met:
(i) C(MCPB2cis)+C(MCPB2trans)>C(MCPB3cis)+C(MCPB3trans);
(ii) 1.5≤C(MCPB2trans)/(C(MCPB3cis)+C(MCPB3trans))≤1000;
(iii) 1.5≤C(MCPB2cis)/(C(MCPB3cis)+C(MCPB3trans))≤1000; and
(iv) 1.5≤(C(MCPB2cis)+C(MCPB2trans))/(C(MCPB3cis)+C(MCPB3trans))≤1000.

6. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises (a) cis-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2cis) ppm; (b) trans-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2trans) ppm; and (c) 1-methyl-1-phenylcyclopentane at a concentration of C(MCPB1) ppm; and at least one of the following conditions (i), (ii), (iii), and (iv) is met:
(i) C(MCPB2cis)+C(MCPB2trans)>C(MCPB1);
(ii) C(MCPB2trans)>C(MCPB1);
(iii) 1.5≤C(MCPB2trans)/C(MCPB1)≤1000; and
(iv) 1.5≤(C(MCPB2cis)+C(MCPB2trans))/(C(MCPB1)≤1000.

7. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises (a) cis-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2cis) ppm; (b) trans-1-methyl-2-phenylcyclopentane at a concentration of C(MCPB2trans) ppm; (c) 1-methyl-1-phenylcyclopentane at a concentration of C(MCPB1) ppm; (d) cis-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3cis) ppm; and (e) trans-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3trans) ppm, and at least one of the following conditions (i), (ii), and (iii) is met:
(i) C(MCPB2cis)+C(MCPB2trans)>C(MCPB1)+C(MCPB3cis)+C(MCPB3trans);
(ii) 1.5≤C(MCPB2trans)/(C(MCPB1)+C(MCPB3cis)+C(MCPB3trans))≤1000; and
(iii) 1.5≤(C(MCPB2cis)+C(MCPB2trans))/(C(MCPB1)+C(MCPB3cis)+C(MCPB3trans))≤1000.

8. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises cis-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3cis) ppm and trans-1-methyl-3-phenylcyclopentane at a concentration of C(MCPB3trans) ppm, and at least one of the following conditions (i), (ii), and (iii) is met:
(i) 0.001≤C(MCPB3cis)≤4500;
(ii) 0.001≤C(MCPB3trans)≤4500; and
(iii) 0.001≤C(MCPB3cis)+C(MCPB3trans)≤4500.

9. The cyclohexylbenzene composition of claim 1 , wherein the methylcyclopentylbenzene comprises 1-methyl-1-phenylcyclopentane at a concentration of C(MCPB1) ppm, and 0.001≤C(MCPB1)≤4500.

10. The cyclohexylbenzene composition of claim 1 , further comprising phenol at a concentration no greater than 50 ppm, expressed in terms of weight of phenol on the basis of the total weight of the cyclohexylbenzene composition.

11. The cyclohexylbenzene composition of claim 1 , further comprising cyclohexenylbenzene at a concentration no greater than 50 ppm, expressed in terms of weight of cyclohexenylbenzene on the basis of the total weight of the cyclohexylbenzene composition.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

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

Classifications

• C07C2529/74

  Noble metals · CPC title

• C07C13/28 Primary

  Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2529/76

  Iron group metals or copper · CPC title

• C07C7/04

  by distillation · CPC title