Polyhydroxyalkanoate derivatives, preparation and uses thereof
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-067/31
C07C-001/24
C07C-051/16
C07C-067/03
C07C-029/09
C07C-029/149
출원번호
US-0404384
(2013-05-31)
등록번호
US-9359283
(2016-06-07)
국제출원번호
PCT/US2013/043716
(2013-05-31)
국제공개번호
WO2013/181604
(2013-12-05)
발명자
/ 주소
Smith, Ryan L.
Bissell, John
Masuno, Makoto N.
Cannon, Douglas
Wood, Alex B.
출원인 / 주소
Micromidas, Inc.
대리인 / 주소
Morrison & Foerster LLP
인용정보
피인용 횟수 :
1인용 특허 :
13
초록▼
Provided herein are methods that utilize polyhydroxyalkanoates (PHAs) as a substrate for further conversion to C4 and C5 compounds. Polyhydroxyalkanoates can undergo esterification to yield alkyl hydroxyalkanoates and alkyl alkenoates, which may serve as useful precursors in the production of alkadi
Provided herein are methods that utilize polyhydroxyalkanoates (PHAs) as a substrate for further conversion to C4 and C5 compounds. Polyhydroxyalkanoates can undergo esterification to yield alkyl hydroxyalkanoates and alkyl alkenoates, which may serve as useful precursors in the production of alkadienes and alkenedioic acids, including for example butadiene and butenedioic acid.
대표청구항▼
1. A method, comprising contacting a polyhydroxyalkanoate with an alcohol to convert at least a portion of the polyhydroxyalkanoate to an alkyl hydroxyalkanoate, wherein: (i) the alcohol is a critical alcohol, a supercritical alcohol or a near-critical alcohol; or(ii) the method further comprises he
1. A method, comprising contacting a polyhydroxyalkanoate with an alcohol to convert at least a portion of the polyhydroxyalkanoate to an alkyl hydroxyalkanoate, wherein: (i) the alcohol is a critical alcohol, a supercritical alcohol or a near-critical alcohol; or(ii) the method further comprises heating the polyhydroxyalkanoate and the alcohol to critical, supercritical or near-critical conditions to produce the alkyl hydroxyalkanoate; orboth (i) and (ii). 2. The method of claim 1, wherein the polyhydroxyalkanoate is contacted with the alcohol at a temperature between 150° C. and 350° C.; and at a pressure between 500 psi and 3000 psi. 3. The method of claim 1, wherein the polyhydroxyalkanoate and the alcohol are further contacted with a solvent, a base, or both a solvent and a base, to convert at least a portion of the polyhydroxyalkanoate to the alkyl hydroxyalkanoate. 4. The method of claim 3, wherein the solvent comprises an organic solvent. 5. The method of claim 3, wherein the solvent comprises chloroform, dichloromethane, dichloroethane, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, acetonitrile, acetone, acetic acid, dioxane, diglyme, dioxin, tetrahydrofuran, pentane, hexane, heptane, benzene, toluene, xylene, trimethylbenzene, ethylbenzene, methylethylbenzene, or hexofluoroisopropanol, or a mixture thereof. 6. The method of claim 3, wherein the base is selected from the group consisting of an organic base, a carbonate salt, an oxide salt, a hydroxide salt, and a buffer, or a combination thereof. 7. The method of claim 1, wherein the alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, pentanol and hexanol. 8. The method of claim 1, wherein the alkyl hydroxyalkanoate is alkyl 3-hydroxyalkanoate. 9. The method of claim 8, wherein the alkyl 3-hydroxyalkanoate is methyl 3-hydroxybutanoate. 10. The method of claim 1, wherein the polyhydroxyalkanoate is selected from the group consisting of polyhydroxybutyrate (PHB),polyhydroxyvalerate (PHV), polyhydroxybutyratevalerate (PHBV), andpolyhydroxyhexanoate (PHH), or a combination thereof. 11. The method of claim 1, further comprising converting at least a portion of the alkyl hydroxyalkanoate produced to an alkanediol. 12. The method of claim 11, further comprising converting at least a portion of the alkanediol to an alkadiene. 13. The method of claim 1, wherein at least a portion of the polyhydroxyalkanoate is converted to an alkyl hydroxyalkanoate, andthe method further comprises converting at least a portion of the alkyl hydroxyalkanoate to an alkadiene. 14. The method of claim 1, wherein the alcohol is methanol, and wherein at least a portion of the polyhydroxyalkanoate is converted to methyl 3-hydroxybutanoate, and the method further comprises: converting at least a portion of the methyl 3-hydroxybutanoate to butanediol; andconverting at least a portion of the butanediol to butadiene. 15. The method of claim 1, wherein the alcohol is methanol.
Zhong, Luhua; Muller, Edward M.; Barber, James J.; Pugach, Joseph; Whitehouse, Robert S.; Daughtry, Sean K., Methods of making intermediates from polyhydroxyalkanoates.
Zhong,Luhua; Muller,Edward M.; Barber,James J.; Pugach,Joseph; Whitehouse,Robert S.; Daughtry,Sean K., Methods of making intermediates from polyhydroxyalkanoates.
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