# US 11,111,202 B2 · Production of salts of 4-hydroxybutyrate using biobased raw materials

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

- Number: US 11,111,202 B2
- Document ID: US11111202B2
- Status: Granted
- Kind: B2
- Application number: 16/241,217
- Filed: 2019-01-07
- Published: 2019-05-09
- Granted: 2021-09-07
- Earliest claimed: 2012-11-14
- Assignees: Cj Cheiljedang Corporation
- Applicants: CJ Cheiljedang Corporation
- Inventors: Oliver P. Peoples; Derek Samuelson; Max Senechal; Sung Min Park; Joseph Gredder; Christopher Mirley
- Web page: https://patentgrep.com/patent/US11111202B2

## CPC

- C07C 59/01: Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- A61K 9/28: Dragees; Coated pills or tablets {, e.g. with film or compression coating (A61K9/2072 takes precedence, e.g. partially coated tablets A61K9/2072, coated multilayer tablets A61K9/2086, tablets with drug-coated core A61K9/209)}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61L 17/105: {Polyesters not covered by A61L17/12}
- C07C 51/41: Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D)
- C07D 307/06: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D 307/33: in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C08G 63/06: derived from hydroxycarboxylic acids
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Gamma-butyrolactone (“GBL”) and Gamma-hydroxybutyrate (“GHB”) having a unique carbon footprint as defined by the percent modern carbon (pmc) are described herein. The percent modern carbon can be controlled by varying the amounts of biobased, renewable starting materials and petroleum-based starting materials to prepare GBL or GHB having a defined pmc or by preparing mixtures of GBL or GHB prepared from biobased renewable starting materials and GBL or GHB prepared from petroleum-based starting materials.

## Claims

### Claim 1

A method for producing a sample from an approved source, said method comprising:
fermenting engineered microbes which produce poly(4-hydroxybutyrate) (P4HB) polymer with a growth medium comprising D2O with deuterated glucose or without deuterated glucose to produce a deuterated P4HB;
reacting the deuterated P4HB for obtaining a deuterated gamma-butyrolactone, a deuterated 4-hydroxybutyrate, an oligomer of deuterated 4-hydroxybutyrate, or a combination thereof; and
mixing the reacted deuterated P4HB with a gamma-butyrolactone prepared from petroleum-based starting materials, a 4-hydroxybutyrate prepared from petroleum-based starting materials, an oligomer of 4-hydroxybutyrate prepared from petroleum-based starting materials, or a combination thereof to prepare a mixture of GBL, a mixture of GHB, a mixture of oligomers of 4-hydroxybutyrate, or a mixture comprising a combination thereof, wherein the mixture has a chosen percent modern carbon range,
wherein the growth medium comprises a selected mixture of a biobased material and a petroleum-based material to yield a desired percent modern carbon, wherein a percentage of the carbon in the deuterated P4HB is modern carbon and the remaining percentage of carbon is fossil-carbon, wherein the chosen percent modern carbon range is controlled to provide a unique carbon footprint, and wherein the chosen percent modern carbon range corresponds to a defined range of the approved source,
wherein the growth medium comprises a concentration of D2O above the natural abundance in water, and
wherein the deuterated P4HB produced by fermenting is 27% to 80% deuterated.

### Claim 2 (depends on 1)

The method of claim 1, wherein the percentage of the carbon in the deuterated P4HB that is modern carbon is at least 80% as measured by the ASTM D6866 protocol.

### Claim 3 (depends on 1)

The method of claim 1, wherein the reacting comprises pyrolysing the deuterated P4HB under the condition suitable for pyrolysis of the deuterated P4HB.

### Claim 4 (depends on 1)

The method of claim 1, wherein the reacting comprises reacting the deuterated P4HB with a base under the condition suitable for base-catalyzed hydrolysis of the deuterated P4HB.

### Claim 5 (depends on 1)

The method of claim 1, wherein the reacting comprises reacting the deuterated P4HB with a base in the presence of a catalyst under the condition suitable for a catalyzed depolymerization of the deuterated P4HB.

### Claim 6 (depends on 1)

The method of claim 1, wherein the growth medium comprises D2O without deuterated glucose and wherein the D2O is the only deuterium source above natural abundance in the growth medium.