# US 11,028,039 B2 · Method for preparing a β-hydroxycarboxylic acid ester

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- Number: US 11,028,039 B2
- Document ID: US11028039B2
- Status: Granted
- Kind: B2
- Application number: 16/734,824
- Filed: 2020-01-06
- Published: 2020-10-01
- Granted: 2021-06-08
- Earliest claimed: 2019-03-26
- Assignees: Shenyang Gold Jyouki Technology Co., Ltd
- Applicants: Shenyang Gold Jyouki Technology Co., Ltd
- Inventors: Kai Yu; Wei Xu
- Web page: https://patentgrep.com/patent/US11028039B2

## CPC

- C07C 67/37: by reaction of ethers with carbon monoxide
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A method of preparing β-hydroxycarboxylic acid ester comprises mixing an alkylene oxide, a monohydric alcohol and a composite catalyst, and performing a carbonylation esterification reaction in a carbon monoxide atmosphere to obtain the β-hydroxycarboxylic acid ester. The composite catalyst comprises a main catalyst, a cocatalyst and a reducing agent. the main catalyst is at least one of a cobalt salt, cobalt oxide and cobalt hydroxide. The cocatalyst is a nitrogen-containing heterocyclic compound. The reducing agent is a base metal. The method is an atomic reaction type process, does not produce three wastes, and has high conversion rate. It is a green environmental protection process. The composite catalyst used does not contain Co2(CO)8. The raw materials and catalyst used are all cheap and easily available. The composite catalyst can be used repeatedly at a lower cost, and is suitable for industrial applications.

## Claims

### Claim 1

A method for preparing a β-hydroxycarboxylic acid ester, comprising the steps of:
mixing an alkylene oxide, a monohydric alcohol, and a composite catalyst, and
performing a carbonylation esterification reaction in a carbon monoxide atmosphere to obtain the β-hydroxycarboxylic acid ester;
wherein the composite catalyst comprises a main catalyst, a cocatalyst, and a reducing agent;
the main catalyst comprises at least one of a cobalt salt and a cobalt hydroxide;
the cocatalyst is a nitrogen-containing heterocyclic compound; and
the reducing agent is a base metal wherein the cobalt salt is selected from the group consisting of cobalt fluoride, cobalt chloride, cobalt bromide, cobalt iodide, cobalt acetate, cobalt carbonate, cobalt nitrate, cobalt sulfate, and combinations thereof;
wherein the nitrogen-containing heterocyclic compound is selected from the group consisting of a pyrazole compound, an imidazole compound, a pyridine compound, and a quinolone compound;
and wherein the base metal is selected from the group consisting of iron, zinc, manganese, nickel copper, and aluminum.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the ratio of the molar amounts of the main catalyst, the cocatalyst, and the reducing agent is 1:(2 to 6):(2 to 10).

### Claim 3 (depends on 1)

The method according to claim 1, wherein the amount of the main catalyst is from 0.5 to 5 mol % based on the alkylene oxide.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the pyrazole compound is selected from the group consisting of pyrazole, 1-methylpyrazole, and 2-methylpyrazole; and the imidazole compound comprises at least one of imidazole, 1-methyl imidazole, 4-phenylimidazole, and 1-acetylimidazole; the pyridine compound comprises at least one of pyridine, 3-hydroxypyridine, 2-hydroxypyridine, 2-aminopyridine, 4-aminopyridine, 4-N,N-dimethyl Pyridine, 2,2-bipyridine, and 4,4-bipyridine; the quinoline compound comprises at least one of quinoline, isoquinoline, and 8-hydroxyquinoline.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the ratio of the alkylene oxide to the monohydric alcohol is 1 mmol:1 to 5 mL.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the carbonylation esterification reaction is carried out at a pressure of 3 to 10 MPa, a temperature of 40 to 120° C., and a time of 10 to 30 hours.