Cyclic imide slurry compositions

Patent metadata

Field	Value
Publication number	US-10584096-B2
Application number	US-201716338827-A
Country	US
Kind code	B2
Filing date	Sep 18, 2017
Priority date	Oct 18, 2016
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

Provided herein is a cyclic imide slurry composition and processes for forming and/or using such a composition. The slurry composition comprises solid cyclic imide and organic liquid, such as liquid alkylbenzene, liquid cyclohexane, and/or liquid organic alcohol (such as cyclohexanol). The slurry composition may find particular use in processes in which the cyclic imide serves as an oxidation catalyst (e.g., as a radical initiator). For instance, the slurry composition may be useful in the oxidation of a liquid alkylbenzene such as cyclohexylbenzene to corresponding 1-cyclohexyl-1-phenyl hydroperoxide. Such an oxidation reaction may further be part of an integrated process for the production of phenol and/or cyclohexanone from benzene via hydroalkylation to form cyclohexylbenzene.

First claim

The invention claimed is:

1. A process comprising:
(a) feeding a solid cyclic imide and a liquid alkylbenzene to a mixing device;
(b) within the mixing device, forming a slurry comprising 3 wt % to 45 wt % of the solid cyclic imide in the liquid alkylbenzene;
(c) providing the slurry and an oxygen-containing gas to a mixed gas/liquid oxidation reaction zone; and
(d) oxidizing at least a portion of the alkylbenzene in the mixed gas/liquid oxidation reaction zone in the presence of the cyclic imide, thereby forming a corresponding alkylbenzene-hydroperoxide; and
further comprising measuring the temperature of the slurry and one or both of density and viscosity of the slurry, and controlling the feed of solid cyclic imide and/or liquid alkylbenzene into the mixing device based at least in part upon the measured temperature and measured density and/or viscosity, so as to form the slurry comprising 3 wt % to 45 wt % of the solid cyclic imide.

2. The process of claim 1 , wherein the cyclic imide has the general formula (I):

where, in formula (I), X is an oxygen atom or a hydroxyl group, and further wherein each of R 7 , R 8 , R 9 , and R 10 is independently selected from: (1) H; (2) C 1 to C 20 linear, cyclic, or aromatic hydrocarbon groups; (3) SO 3 H; (4) NH 2 ; (5) OH; (6) a halogen; and (7) NO 2 .

3. The process of claim 2 , wherein the cyclic imide is N-hydroxyphthalimide (NHPI).

4. The process of claim 1 , wherein the alkylbenzene has the general formula (II), and the alkylbenzene-hydroperoxide has the general formula (III):

where, in each general formula (II) and (III), R 4 and R 5 are each independently selected from hydrogen or an alkyl group having from 1 to 4 carbon atoms, provided that R 4 and R 5 may also be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R 6 is selected from the group consisting of hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms, and a cyclohexyl group.

5. The process of claim 4 , wherein the alkylbenzene is cyclohexylbenzene, and the alkylbenzene-hydroperoxide is cyclohexyl-1-phenyl-1-hydroperoxide.

6. The process of claim 5 , further comprising:
(a-1) contacting benzene with hydrogen under hydroalkylation conditions in the presence of a hydroalkylation catalyst to produce cyclohexylbenzene;
(a-2) feeding a first portion of the cyclohexylbenzene to the mixing device; and
(a-3) feeding a second portion of the cyclohexylbenzene to the oxidation reaction zone.

7. The process of claim 1 , further comprising measuring mass flow rate of the solid cyclic imide fed into the mixing device, and controlling the feed of solid cyclic imide into the mixing device based at least in part upon the measured mass flow rate, so as to form the slurry comprising 3 wt % to 45 wt % of the solid cyclic imide.

8. The process of claim 1 , wherein the slurry comprises 10 wt % to 30 wt % solid cyclic imide in liquid alkylbenzene.

9. The process of claim 1 , wherein the slurry comprises at most 0.1 wt % of impurities.

10. The process of claim 1 , further comprising recirculating at least a portion of the slurry out of and back into the mixing device.

11. The process of claim 1 , further comprising feeding an inert gas to the mixing device so as to maintain an inert overhead environment in the mixing device.

12. The process of claim 1 , wherein providing the slurry to the mixed gas/liquid oxidation reaction zone comprises mixing the slurry with a combined liquid feed stream comprising liquid alkylbenzene having general formula (II) and corresponding hydroperoxide having general formula (III) so as to form a mixed feed stream, and providing the mixed feed stream to an oxidation reactor.

13. The process of claim 12 , wherein the combined liquid feed stream is formed by recycling a portion of a liquid oxidation effluent stream to be combined with a liquid alkylbenzene feed stream.

14. The process of claim 1 , wherein providing the slurry to the mixed gas/liquid oxidation reaction zone comprises mixing the slurry with a liquid stream by way of a mixing tee, a nozzle, a spray nozzle, or a quill with orifices.

15. A process comprising:
(a) feeding a solid cyclic imide and liquid cyclohexane to a mixing device;
(b) within the mixing device, forming a slurry comprising 3 wt % to 45 wt % of the solid cyclic imide in the liquid cyclohexane;
(c) providing the slurry and an oxygen-containing gas to a mixed gas/liquid oxidation reaction zone; and
(d) oxidizing at least a portion of the cyclohexane in the mixed gas/liquid oxidation reaction zone in the presence of the cyclic imide, thereby forming cyclohexanol and/or cyclohexanone; and
further comprising measuring temperature of the slurry and one or both of density and viscosity of the slurry, and controlling the feed of solid cyclic imide and/or liquid cyclohexane into the mixing device based at least in part upon the measured temperature and measured density and/or viscosity, so as to form the slurry comprising 3 wt % to 45 wt % of the solid cyclic imide.

16. A process comprising:
(a) feeding a solid cyclic imide and liquid organic alcohol to a mixing device;
(b) within the mixing device, forming a slurry comprising 3 wt % to 45 wt % of the solid cyclic imide in the liquid organic alcohol;
(c) providing the slurry and an oxygen-containing gas to a mixed gas/liquid oxidation reaction zone; and
(d) oxidizing at least a portion of the alcohol in the mixed gas/liquid oxidation reaction zone in the presence of the cyclic imide; and
further comprising measuring the temperature of the slurry and one or both of density and viscosity of the slurry, and controlling the feed of solid cyclic imide and/or liquid liquid organic alcohol into the mixing device based at least in part upon the measured temperature and measured density and/or viscosity, so as to form the slurry comprising 3 wt % to 45 wt % of the solid cyclic imide.

17. The process of claim 16 , wherein the organic alcohol is cyclohexanol.

18. The process of claim 15 , wherein the cyclic imide has the general formula (I):

where, in formula (I), X is an oxygen atom or a hydroxyl group, and further wherein each of R 7 , R 8 , R 9 , and R 10 is independently selected from: (1) H; (2) C 1 to C 20 linear, cyclic, or aromatic hydrocarbon groups; (3) SO 3 H; (4) NH 2 ; (5) OH; (6) a halogen; and (7) NO 2 .

19. The process of claim 15 , wherein the cyclic imide is N-hydroxyphthalimide (NHPI).

Assignees

• Exxonmobile Chemical Patents Inc
• Exxonmobil Chemical Patents Inc

Inventors

• Witt Andrew R
• Becker Christopher L
• Patel Bryan A

Classifications

• C07C29/50

  with molecular oxygen only · CPC title

• B01J31/0247

  Imides, amides or imidates (R-C=NR(OR)) · CPC title

• C07C39/04

  Phenol · CPC title

• C07C409/14

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

• C07C2601/14

  The ring being saturated · CPC title