# US 4,393,223 A · Process for the production of macrocyclic esters and lactones utilizing mixed metal catalysts

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,393,223 A
- Document ID: US4393223A
- Status: Granted
- Kind: A
- Application number: 06/285,727
- Filed: 1981-07-22
- Granted: 1983-07-12
- Earliest claimed: 1979-09-10
- Assignees: Emery Industries, Inc.
- Inventors: Eugene G. Harris
- Web page: https://patentgrep.com/patent/US4393223A

## CPC

- C07D 323/00: Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C11B 9/0084: {the hetero rings containing more than six atoms}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)

## Abstract

Mixed metal compounds comprised of aluminum alkoxides or aluminum carboxylates with an alkali metal or magnesium alkoxide or carboxylate are useful catalysts for the thermal depolymerization of polyesters to produce macrocyclic compounds. High yields and enhanced rates of reaction are possible utilizing these mixed metal catalysts in known depolymerization procedures.

## Claims

### Claim 1

A process for the production of macrocyclic compounds having 8 to 20 carbon atoms in the ring and selected from the group consisting of ##STR8## where R' is a bivalent aliphatic hydrocarbon radical having 1 to 16 carbon atoms, R" is a saturated bivalent aliphatic hydrocarbon radical having from 2 to 12 carbon atoms, R"' is a bivalent aliphatic hydrocarbon radical having 6 to 18 carbon atoms and x is an integer from 1 to 4 by thermal depolymerization of the corresponding linear polyester which comprises heating the polyester at a temperature from 200.degree. C. to 400.degree. C. and pressure less than 50 mm Hg. in the presence of 0.01% to 20% by weight, based on the polyester, of a mixed metal catalyst comprising:
(a) an aluminum alkoxide or aluminum carboxylate corresponding to the formula ##STR9## where m is an integer from 1 to 22, R.sub.1 is hydrogen, an alkoxy or polyalkoxy radical having from 1 to 16 carbon atoms and R.sub.2 is an alkyl group having from 2 to 22 carbon atoms, phenyl or substituted phenyl having 7 to 20 carbon atoms; and
(b) from 0.05 to 8 moles, per mole of (a), of an alkali metal or magnesium alkoxide or carboxylate corresponding to the formula ##STR10## wherein R.sub.1, R.sub.2 and m are the same as defined above, M is lithium, sodium, potassium or magnesium and y is 1 when M is lithium, sodium or potassium, and 2 when M is magnesium.

### Claim 2 (depends on 1)

The process of claim 1 wherein m is an integer from 2 to 12, R.sub.1 is hydrogen, methoxy, ethoxy, di- tri- or tetra-ethoxy, R.sub.2 is a C.sub.8-18 alkyl, phenyl or substituted phenyl wherein the substituent is an alkyl, alkoxy or polyalkoxy group, M is lithium, sodium or potassium and Y is 1.

### Claim 3 (depends on 2)

The process of claim 2 wherein R' is a saturated bivalent aliphatic hydrocarbon radical having 6 to 12 carbon atoms, R" has 2 to 6 carbon atoms, R"' is a saturated bivalent aliphatic hydrocarbon radical having 10 to 14 carbon atoms and x is 1 or 2.

### Claim 4 (depends on 1, 2)

The process of claims 1, 2 3 wherein the mixed metal catalyst is present in an amount from 0.1 to 10 weight percent, based on the weight of the polyester.

### Claim 5 (depends on 4)

The process of claim 4 wherein the depolymerization is carried out at a temperature in the range 250.degree. C. to 360.degree. C. and pressure of 10 mm Hg. to 0.01 mm Hg.

### Claim 6 (depends on 5)

The process of claim 5 wherein the depolymerization is conducted as a continuous or semi-continuous operation.

### Claim 7 (depends on 3)

The process of claim 3 wherein the macrocyclic compound is ethylene brassylate.

### Claim 8 (depends on 3)

The process of claim 3 wherein the macrocyclic compound is pentadecanolide.