Production of salts of 4-hydroxybutyrate using biobased raw materials

Patent metadata

Field	Value
Publication number	US-11111202-B2
Application number	US-201916241217-A
Country	US
Kind code	B2
Filing date	Jan 7, 2019
Priority date	Nov 14, 2012
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

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.

First claim

We 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 D 2 O 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 D 2 O above the natural abundance in water, and
wherein the deuterated P4HB produced by fermenting is 27% to 80% deuterated.

2. 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.

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

4. 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.

5. 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.

6. The method of claim 1 , wherein the growth medium comprises D 2 O without deuterated glucose and wherein the D 2 O is the only deuterium source above natural abundance in the growth medium.

Assignees

• Cj Cheiljedang Corp

Inventors

• Peoples Oliver P
• Samuelson Derek
• Senechal Max
• Park Sung Min
• Gredder Joseph
• Mirley Christopher

Classifications

• C07D307/06 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C07C59/01 Primary

  Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups · CPC title

• A61L17/105

  Polyesters not covered by A61L17/12 · CPC title

• C07D307/33

  in position 2, the oxygen atom being in its keto or unsubstituted enol form · CPC title

• A61K9/28

  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)} · CPC title