- METHOD FOR PRODUCING AN ALKYL 3-HYDROXYBUTYRATE
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A method for making an alkyl 3-hydroxybutyrate is provided. The method can include reacting an alkyl alcohol with diketene to form an alkyl acetoacetate and then hydrogenating the alkyl acetoacetate to form the alkyl 3-hydroxybutyrate. The method of the present invention may also include separating one or more impurities an alkyl acetoacetate stream and subjecting the purified acetoacetate mixture to hydrogenation to form the alkyl 3-hydroxybutyrate. Methods of the present invention can be carried out on a lab, pilot, or commercial scale.
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Paragraph 0060
(2015/02/19)
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- Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone
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Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.
- Kakasi-Zsurka, Sandor,Todea, Anamaria,But, Andrada,Paul, Cristina,Boeriu, Carmen G.,Davidescu, Corneliu,Nagy, Lajos,Kuki, Akos,Keki, Sandor,Peter, Francisc
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experimental part
p. 22 - 28
(2012/02/03)
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- Sodium borohydride reduction and selective transesterification of β-keto esters in a one-pot reaction under mild conditions
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An efficient and simple one-pot method of preparing β-hydroxy esters by sodium borohydride reduction cum selective transesterification of β-keto esters under mild conditions is described.
- Padhi, Santosh Kumar,Chadha, Anju
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p. 639 - 642
(2007/10/03)
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- Hydroxyester disaccharides from fruits of cape gooseberry (Physalis peruviana)
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The 3-O-β-D-glucopyranosyl-(1→6)-β-D -glucopyranoside of ethyl 3-hydroxyoctanoate and the diastereomeric 3-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosides of (3R) and (3S)-butyl 3-hydroxybutanoate, respectively, were isolated by chromatographic methods
- Mayorga, Humberto,Duque, Carmenza,Knapp, Holger,Winterhalter, Peter
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p. 439 - 445
(2007/10/03)
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- Aliphatic β-D-glucosides from fruits of Carica pubescens
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Ethyl 3-O-β-D-glucopyranosylbutanoate, butyl 3-O-β-D- glucopyranosylbutanoate and 3-oxo-octyl 1-O-β-D-glucopyranoside were isolated from Carica pubescens fruit pulp by liquid chromatography on XAD. Identifications were performed after peracetylation by comparison of HRGC and HRGC-mass spectral data with those of synthesized reference compounds. Chiral evaluation of glycosidically-bound 3-hydroxybutanoates and octane-1,3-diol was achieved by multidimensional gas chromatography, combining a polar achiral column (DB-Wax) with a chiral main column (heptakis-2,6-di-O-methyl- 3-O-pentyl-β-cyclodextrin/OV 1701 and 2.3-di-O-acetyl-6-O-tert-butyl- dimethylsilyl-β-cyclodextrin/OV 1701, respectively). Comparison of retention times of synthesized, optically-enriched reference compounds with enzymically-released aglycones revealed enantiomeric excesses of the (S)-3- hydroxybutanoates, i.e. 96% and 24%, for the ethyl and the butyl ester, respectively. Octane-1,3-diol exhibited an enantiomeric excess of (R)-90%.
- Krajewski, Doris,Duque, Carmenza,Schreier, Peter
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p. 1627 - 1631
(2007/10/03)
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- ENHANCED OPTICAL PURITY OF 3-HYDROXYESTERS OBTAINED BY BAKER'S YEAST REDUCTION OF 3-KETOESTERS
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Fermenting Baker's yeast, enclosed in a dialysis tube, reduces efficiently 3-ketoesters added to the surrounding subtonic solution, to the corresponding 3-hydroxyesters in good yield (45-55percent) and enhanced optical purity (ee 96-97percent)
- Spiliotis, Vassilis,Papahatjis, Demetris,Ragoussis, Nikitas
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p. 1615 - 1616
(2007/10/02)
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