Biocatalytic Heterogeneous Processes of Low-Temperature Synthesis of Diol Monoesters Full article
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Kinetics and Catalysis
ISSN: 0023-1584 , E-ISSN: 1608-3210 |
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| Output data | Year: 2022, Volume: 63, Number: 2, Pages: 188-196 Pages count : 9 DOI: 10.1134/s0023158422020045 | ||||
| Tags | biocatalytic esterification; immobilization; recombinant lipase; synthesis of diol monoesters | ||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Ministry of Science and Higher Education of the Russian Federation | 0239-2021-0005 |
Abstract:
A study was made of the low-temperature synthesis of esters of heptanoic (enanthic, C7:0) acid and various diols using heterogeneous biocatalysts prepared by the adsorptive immobilization of the recombinant lipase rPichia/lip on macroporous carbon aerogel. The substrates were diols differing in length of the carbon skeleton (2 to 6 C atoms), position of the OH group, and isomerism of the carbon skeleton, namely, 1,2-ethanediol (ethylene glycol) and its oligomers (dimers and trimers), 1,2-propanediol (propylene glycol), 1,3‑propanediol, 1,4-butanediol, 1,6-hexanediol, and 2-ethyl-1,3-hexanediol. The esterification and synthesis of monoesters of heptanoic acid were carried out in batch reactors under very mild conditions (20 ± 2°C, 1 bar). The properties of the prepared biocatalysts, such as enzymatic activity, substrate specificity, and operational stability, were investigated depending on the structure of the diol molecule and the nature of the organic solvent (chloroform, hexane, acetone). It was found that C2–C4 short-chain diols irreversibly inhibited the immobilized lipase, and the biocatalyst was completely inactivated within 1–3 reaction cycles. The maximum activity (83 U/g) and the conversion of acid (94% in 24 h) were observed in the esterification of heptanoic acid with 1,6-hexanediol; under the studied conditions, the fraction of monoester was more than 99%. A correlation was found between the biocatalytic activity and the molecular length of symmetric diols: the esterification reaction rate increased with increasing distance between the terminal OH groups. Because chloroform inactivated the adsorbed rPichia/lip, the conditions for the reactivation of the biocatalysts were selected by replacing the reaction medium: the solvent by hexane and the diol by butanol.
Cite:
Kovalenko G.A.
, Perminova L.V.
, Shashkov M.V.
, Beklemishev A.B.
Biocatalytic Heterogeneous Processes of Low-Temperature Synthesis of Diol Monoesters
Kinetics and Catalysis. 2022. V.63. N2. P.188-196. DOI: 10.1134/s0023158422020045 WOS Scopus РИНЦ AN OpenAlex
Biocatalytic Heterogeneous Processes of Low-Temperature Synthesis of Diol Monoesters
Kinetics and Catalysis. 2022. V.63. N2. P.188-196. DOI: 10.1134/s0023158422020045 WOS Scopus РИНЦ AN OpenAlex
Original:
Коваленко Г.А.
, Перминова Л.В.
, Шашков М.В.
, Беклемишев А.Б.
Биокаталитические гетерогенные процессы низкотемпературного синтеза моноэфиров диолов
Кинетика и катализ. 2022. Т.63. №2. С.212-222. DOI: 10.31857/S0453881122020046 РИНЦ
Биокаталитические гетерогенные процессы низкотемпературного синтеза моноэфиров диолов
Кинетика и катализ. 2022. Т.63. №2. С.212-222. DOI: 10.31857/S0453881122020046 РИНЦ
Dates:
| Submitted: | Jul 2, 2021 |
| Accepted: | Aug 14, 2021 |
| Published print: | Apr 1, 2022 |
| Published online: | May 16, 2022 |
Identifiers:
| Web of science: | WOS:000796501300007 |
| Scopus: | 2-s2.0-85130303481 |
| Elibrary: | 48584616 |
| Chemical Abstracts: | 2022:1305759 |
| OpenAlex: | W4280609886 |