IP Library › Granted Patent US 10,570,079
Granted Patent B2
US 10,570,079 · App. 16/280,668 · Granted Feb 25, 2020

Cyclohexanone compositions and processes for making such compositions

Inventors: Ashley J. Malik (Houston, TX); Jörg F. W. Weber (Houston, TX); Medrado M. Leal (El Lago, TX)
Assignee: ExxonMobil Chemical Patents Inc.
C07C49/543C07C45/006C07C45/53C07C45/82C07C2601/14
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Quick Facts
Patent No.
US 10,570,079
App. No.
16/280,668
Granted
Feb 25, 2020
Kind
B2
Abstract

Disclosed are processes for making such cyclohexanone compositions from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene. Such cyclohexanone compositions comprise at least 99 wt % cyclohexanone, at most 0.15 wt % water, and at most 500 wppm combined of certain cyclohexanone impurities selected from the group consisting of: benzene, cyclohexene, pentanal, cyclopentanol, cyclohexanol, and phenol.

Claims (40)

1. A process of obtaining a cyclohexanone composition comprising:

first producing cyclohexylbenzene by contacting benzene with hydrogen in the presence of a bifunctional catalyst comprising a molecular sieve of the MCM-22 type and at least one hydrogenation metal selected from palladium, ruthenium, nickel, cobalt, and mixtures thereof, to produce a crude feed of phenol, cyclohexanone and cyclohexylbenzene;

isolating the cyclohexanone from the crude feed of phenol, cyclohexanone and cyclohexylbenzene by passing the crude feed through a first distillation column, a hydrogenation reactor, and a cyclohexanone purification column, wherein the crude feed passes through a sorbent bed before passing to the hydrogenation reactor, the sorbent bed configured to remove at least a portion of the sulfur-containing components and/or the light components from a crude feed;

wherein the composition comprises:

(a) at least 99 wt % cyclohexanone;

(b) 0.15 wt % or less water;

(c) 0 to 10 wppm benzene;

(d) 5 to 10 wppm cyclohexene;

(e) 0 to 10 wppm pentanal;

(f) 0 to 50 wppm cyclopentanol; and

(g) 10 wppm to 40 wppm cyclohexanol; and

wherein the wt % and wppm are each based upon total weight of the cyclohexanone composition.

2. The process of claim 1 , comprising at least 99.9 wt % cyclohexanone and at most 0.05 wt % water, based upon the total weight of the cyclohexanone composition.

3. The process of claim 1 , comprising 1 wppm to 10 wppm pentanal, based upon the total weight of the cyclohexanone composition.

4. The process of claim 3 , comprising 10 wppm to 50 wppm cyclopentanol, based upon the total weight of the cyclohexanone composition.

5. The process of claim 1 , comprising 10 wppm to 50 wppm cyclopentanol, based upon the total weight of the cyclohexanone composition.

6. The process of claim 1 , comprising 10 wppm to 20 wppm cyclohexanol.

7. The process of claim 1 , wherein the cyclohexanone composition consists of:

(a) at least 99 wt % cyclohexanone;

(b) 0.15 wt % or less water;

(c) 0 to 10 wppm benzene;

(d) 5 to 10 wppm cyclohexene;

(e) 0 to 10 wppm pentanal;

(f) 0 to 50 wppm cyclopentanol; and

(g) 10 wppm to 40 wppm cyclohexanol;

wherein the wt % and wppm are each based upon total weight of the cyclohexanone composition.

8. The process of claim 7 , wherein the cyclohexanone is present at 99.9 wt % or greater, and further wherein the water is present at 0.05 wt % or less, based upon the total weight of the cyclohexanone composition.

9. The process of claim 7 , wherein the pentanal is present within the range of 1 to 10 wppm, based upon the total weight of the cyclohexanone composition.

10. The process of claim 7 , wherein the cyclopentanol is present within the range of 10 to 50 wppm, based upon the total weight of the cyclohexanone composition.

11. The process of claim 7 , wherein the cyclohexanol is present within the range of 10 wppm to 20 wppm, based upon the total weight of the cyclohexanone composition.

12. The process of claim 1 , wherein the composition consists of:

(a) at least 99 wt % cyclohexanone;

(b) 0.15 wt % or less water; and

(c) 500 wppm or less combined of one or more cyclohexanone impurities;

wherein the cyclohexanone impurities comprise pentanal, cyclopentanol, or both; and further

wherein the wt % and wppm are each based upon total weight of the cyclohexanone composition.

13. The process of claim 12 , wherein the cyclohexanone impurities comprise pentanal and cyclopentanol.

14. The process of claim 12 , wherein the cyclohexanone impurities further comprise one or more of: benzene, cyclohexene, cyclohexanol, and phenol.

15. The process of claim 12 , wherein the cyclohexanone impurities consist of: cyclohexene, pentanal, cyclopentanol, and cyclohexanol.

16. The process of claim 12 , comprising at least 99.9 wt % cyclohexanone, at most 0.05 wt % water, and 200 wppm or less combined of the one or more cyclohexanone impurities.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2019
From: MALIK, ASHLEY J.; WEBER, JÖRG F. W.; LEAL, MEDRADO M.
To: EXXONMOBIL CHEMICAL PATENTS INC.
Reel/Frame 048393/0877 →
Continuity (3)
Continuation 15741030
Provisional Application 62198470 · Jul 29, 2015
Related Publication 20190185403A1 · Jun 20, 2019