Synthesis of Highly Pure L-3-Hydroxy-Gamma-Butyrolactone from L-Malic Acid and L-Alaninol from L-Alanine by Selective Hydrogenation over Pt-ReOx/C Catalyst Full article
| Journal |
Catalysis in Green Chemistry and Engineering
ISSN: 2572-9896 , E-ISSN: 2572-990X |
||||
|---|---|---|---|---|---|
| Output data | Year: 2018, Volume: 1, Number: 1, Pages: 27-42 Pages count : 16 DOI: 10.1615/.2017021077 | ||||
| Tags | L-malic acid, alanine, L-3-hydroxy-gamma-butyrolactone, L-alaninol, hydrogenation, chirality, racemization, Pt-ReOx catalyst | ||||
| Authors |
|
||||
| Affiliations |
|
Funding (1)
| 1 | Federal Agency for Scientific Organizations | 0303-2016-0006 (V.44.1.6) |
Abstract:
Selective hydrogenation of L-malic acid and L-alanine aqueous solutions, respectively, to L-3-hydroxy-γ-butyrolactone and L-alaninol on a highly dispersed Pt-ReOx/С catalyst was studied under mild conditions (T=75-110 C). In the low-temperature region, where racemization proceeds by 2-3 orders of magnitude slower than hydrogenation, not only chemically (the lactone yield above 98%) but also optically pure cyclic ester with the enantiomeric excess above 99% can be obtained. In an acid medium (pH < 3.5) L-alanine is in the active state, where carboxyl group is non-dissociated and amine group is protonated. In the region of 3.5 < pH < 7, the structure of amino acid corresponds to Zwitter ion, which is characterized by the presence of inactive carboxylate anions. As in the case of malic acid, the appropriate temperature, pH, catalyst loading and concentration of the acid were found to produce L-alaninol with the yield of 99% and enantiomeric excess above 99%.
Cite:
Balzhinimaev B.
, Suknev A.
, Paukshtis E.
, Batueva I.
Synthesis of Highly Pure L-3-Hydroxy-Gamma-Butyrolactone from L-Malic Acid and L-Alaninol from L-Alanine by Selective Hydrogenation over Pt-ReOx/C Catalyst
Catalysis in Green Chemistry and Engineering. 2018. V.1. N1. P.27-42. DOI: 10.1615/.2017021077 РИНЦ AN OpenAlex
Synthesis of Highly Pure L-3-Hydroxy-Gamma-Butyrolactone from L-Malic Acid and L-Alaninol from L-Alanine by Selective Hydrogenation over Pt-ReOx/C Catalyst
Catalysis in Green Chemistry and Engineering. 2018. V.1. N1. P.27-42. DOI: 10.1615/.2017021077 РИНЦ AN OpenAlex
Dates:
| Submitted: | Jun 27, 2017 |
| Accepted: | Jan 14, 2018 |
Identifiers:
| Elibrary: | 36788505 |
| Chemical Abstracts: | 2020:2039987 |
| OpenAlex: | W2804485459 |