Recovery process for functionalized compound reaction product

Patent metadata

Field	Value
Publication number	US-10654790-B2
Application number	US-201515506611-A
Country	US
Kind code	B2
Filing date	Aug 26, 2015
Priority date	Aug 26, 2014
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

Provided is a process for recovery of a functionalized compound reaction product comprising contacting (i) an oxidizing electrophile comprising a main group element, and (ii) a compound comprising at least one C—H bond, in an acidic medium to form a reaction milieu comprising a functionalized compound reaction product, contacting the reaction milieu with a water-immiscible organic solvent, separating the water-immiscible organic solvent from the reaction milieu, wherein the functionalized compound reaction product is dissolved in the water-immiscible organic solvent, and separating the functionalized compound reaction product and the water-immiscible organic solvent. The water-immiscible extraction solvent can be the same compound as the compound comprising as least one C—H bond, for example, propane or n-butane.

First claim

The invention claimed is:

1. A process for recovery of a functionalized compound reaction product that is soluble in a water-immiscible organic solvent comprising
contacting (i) an oxidizing electrophile comprising a main group element selected from the group consisting of thallium, lead, bismuth, antimony, selenium, arsenic, tellurium, and a mixture thereof, and (ii) a compound comprising at least one C—H bond that is an alkane, a heteroalkane, or an arene, in an aqueous acidic medium to form a reaction milieu comprising a reaction product that is an alkane oxygenate, heteroalkane oxygenate, or arene oxygenate, respectively, wherein at least one C—H bond of the starting alkane, heteroalkane, or arene compound comprising at least one C—H bond is replaced with an oxygenate group, and wherein the reaction product is soluble in a water-immiscible organic solvent,
contacting the reaction milieu with a water-immiscible organic solvent that is a hydrocarbon solvent in which the reaction product is soluble,
separating the water-immiscible organic solvent from the reaction milieu, wherein the reaction product is dissolved in the water-immiscible organic solvent, and
separating the reaction product and the water-immiscible organic solvent.

2. The process of claim 1 , wherein the compound comprising at least one C—H bond is an alkane.

3. The process of claim 2 , wherein the alkane is selected from the group consisting of methane, ethane, propane, butane, and a mixture thereof.

4. The process of claim 1 , wherein the compound comprising at least one C—H bond is a heteroalkane that is an alcohol.

5. The process of claim 1 , wherein the compound comprising at least one C—H bond is an arene that is an aryl ring system or a heteroaryl ring system.

6. The process of claim 1 , wherein the aqueous acidic medium comprises an aqueous carboxylic acid.

7. The process of claim 1 , wherein the reaction product is an ester or a diester.

8. The process of claim 7 , wherein the compound comprising at least one C—H bond is propane and the reaction product is 1,2-propanediol diacetate.

9. The process of claim 1 , wherein the hydrocarbon solvent is a straight chain, branched chain, or cyclic hydrocarbon, or a mixture thereof.

10. The process of claim 9 , wherein the hydrocarbon solvent is a straight chain hydrocarbon comprising 2 to about 20 carbon atoms.

11. The process of claim 10 , wherein the straight chain hydrocarbon is propane, n-butane, or n-pentane.

12. The process of claim 9 , wherein the hydrocarbon solvent is a branched chain hydrocarbon comprising 4 to about 20 carbon atoms.

13. The process of claim 12 , wherein the branched chain hydrocarbon is isobutane, isopentane, or tert-pentane.

14. The process of claim 1 , wherein the water-immiscible organic solvent used for separating the reaction product is the same as the compound comprising as least one C—H bond.

15. The process of claim 14 , wherein the compound comprising at least one C—H bond and the water-immiscible organic solvent are both propane or n-butane.

16. The process of claim 1 , wherein the reaction product and the water-immiscible organic solvent are separated by distillation.

17. The process of claim 1 , wherein the reaction product has a higher boiling point than the aqueous acidic medium.

18. The process of claim 1 , wherein (i) contacting the oxidizing electrophile comprising a main group element and the compound comprising at least one C—H bond in the aqueous acidic medium, (ii) contacting the reaction milieu with the water-immiscible organic solvent, and (iii) separating the water-immiscible organic solvent from the reaction milieu are all carried out as a continuous process.

19. The process of claim 1 , wherein the oxidizing electrophile comprises a main group element selected from the group consisting of lead, bismuth, antimony, selenium, arsenic, tellurium, and a mixture thereof.

Assignees

• Scripps Research Inst

Inventors

• Kouba Jay
• Pietsch Stephen

Classifications

• C07C37/60

  by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen · CPC title

• C07C67/035 Primary

  by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons · CPC title

• C07C69/16

  of dihydroxylic compounds · CPC title

• C07C67/58

  by liquid-liquid treatment · CPC title

• C07C37/58

  by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen · CPC title