Production of cyclic imides suitable for oxidation catalysis

Patent metadata

Field	Value
Publication number	US-11014883-B2
Application number	US-201716096161-A
Country	US
Kind code	B2
Filing date	Apr 18, 2017
Priority date	May 26, 2016
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

Disclosed are novel processes for the production of cyclic imide compounds such as N-hydroxyphthalimide (NHPI). The processes may be particularly well-suited for commercial-scale production of cyclic imides such as NHPI. Such cyclic imide compounds are suitable for use as oxidation catalysts, and specifically may be used to oxidize cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide. Such an oxidation may be particularly useful in a process for the production of phenol and/or cyclohexanone from benzene via a process comprising hydroalkylation of benzene to cyclohexylbenzene, oxidation of the cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide, and cleavage of the cyclohexyl-1-phenyl-1-hydroperoxide to phenol and cyclohexanone. The cyclic imide production process may advantageously include water washing and reactant recovery steps to maximize purity and yield.

First claim

The invention claimed is:

1. A process comprising:
(a) continuously feeding hydroxylamine solution and a cyclic carboxylic acid anhydride to a continuous flow reactor via one or more feed inlets, so as to establish a reaction medium flowing continuously in a downstream direction within the reactor;
(b) at a second location along the reactor that is downstream of the one or more feed inlets, feeding steam or water into the reaction medium;
(c) at a third location along the reactor that is downstream of the second location, feeding additional steam or additional water into the reaction medium;
(d) agitating the reaction medium within the reactor between the second and third locations; and
(e) recovering a reaction product comprising solid cyclic imide from the reaction medium;

wherein the cyclic carboxylic acid anhydride has the general formula (II)

and further wherein the cyclic imide has the general formula (I)

where 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 .

2. The process of claim 1 , wherein the reaction medium comprises liquid solution within the reactor upstream of the second location; the reaction medium comprises a first slurry comprising intermediate hydroxamic acid within the reactor downstream of the second location and upstream of the third location; and further wherein the reaction medium comprises a second slurry comprising solid cyclic imide within the reactor downstream of the third location.

3. The process of claim 1 , wherein the reaction medium has: (i) initial temperature T i less than 65° C. at a location within the reactor upstream of the second location; (ii) transition temperature T t within the range from 65° C. to less than 75° C. at a location within the reactor downstream of the second location and upstream of the third location; and (iii) final temperature T f within the range from 75° C. to 200° C. at a location within the reactor downstream of the third location.

4. The process of claim 1 , wherein the continuous flow reactor is a down-flow reactor, such that the downstream direction is downward.

5. The process of claim 1 , wherein the reaction product comprising solid cyclic imide is withdrawn from a reactor outlet disposed on the reactor at a location downstream from the third location.

6. The process of claim 5 , wherein the reaction product comprises solid cyclic imide in mother liquor.

7. The process of claim 6 , further comprising:
(f) collecting the solid cyclic imide of the reaction product on a filtration belt that is operated so as to convey the solid cyclic imide over one or more vacuum devices; and
(g) collecting at least a portion of the mother liquor of the reaction product in a vacuum conduit via one or more of the vacuum devices in fluid communication with the vacuum conduit.

8. The process of claim 7 , further comprising:
(h) contacting the solid cyclic imide disposed on the filtration belt with wash water having temperature within the range from 0° C. to 30° C.; and
(i) after the contacting in (h), collecting the wash water in the vacuum conduit via one or more of the vacuum devices in fluid communication with the vacuum conduit.

9. The process of claim 8 , further comprising:
(j) drying the solid cyclic imide disposed on the filtration belt after the contacting in (h), and
(k) collecting dried solid cyclic imide in a solid conveyor.

10. The process of claim 9 , wherein the drying (j) comprises:
(j-1) contacting the solid cyclic imide with drying steam and inert gas, such that at least a portion of the drying steam condenses on the solid cyclic imide; and
(j-2) after the contacting in (j-1), collecting at least a portion of the condensed drying steam and inert gas in the vacuum conduit via one or more of the vacuum devices in fluid communication with the vacuum conduit.

11. The process of claim 1 , wherein the hydroxylamine solution comprises 30-70 wt % hydroxylamine, water, and less than 1 wt % of compounds other than hydroxylamine or water.

12. The process of claim 1 , further comprising:
(a-1) contacting a hydroxylammonium salt with an aqueous base to form at least a portion of said hydroxylamine solution.

13. The process of claim 12 , wherein the hydroxylammonium salt is hydroxylammonium sulfate.

14. The process of claim 12 , wherein the aqueous base is selected from the group consisting of sodium hydroxide and ammonia.

15. The process of claim 1 , further comprising providing at least a portion of the solid cyclic imide to an oxidation reaction.

16. The process of claim 1 , further comprising contacting at least a portion of the solid cyclic imide with cyclohexylbenzene and an oxygen-containing gas so as to obtain cyclohexyl-1-phenyl-1-hydroperoxide.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Weber Jörg F W
• Jaensch Helge
• Witt Andrew R
• Becker Christopher L
• Nadler Kirk C
• Galvan Kendele S
• Batton Amy B

Classifications

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title

• C07D209/48 Primary

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• B01J37/04

  Mixing {(B01J37/0009, B01J37/0018 take precedence)} · CPC title