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Self-optimization of continuous flow electrochemical synthesis using Fourier transform infrared spectroscopy and gas chromatography

Self-optimization of continuous flow electrochemical synthesis using Fourier transform infrared spectroscopy and gas chromatography
Self-optimization of continuous flow electrochemical synthesis using Fourier transform infrared spectroscopy and gas chromatography

A continuous-flow electrochemical synthesis platform has been developed to enable self-optimization of reaction conditions of organic electrochemical reactions using attenuated total reflection Fourier transform infrared spectroscopy (ATR FT-IR) and gas chromatography (GC) as online real-time monitoring techniques. We have overcome the challenges in using ATR FT-IR as the downstream analytical methods imposed when a large amount of hydrogen gas is produced from the counter electrode by designing two types of gas-liquid separators (GLS) for analysis of the product mixture flowing from the electrochemical reactor. In particular, we report an integrated GLS with an ATR FT-IR probe at the reactor outlet to give a facile and low-cost solution to determining the concentrations of products in gas-liquid two-phase flow. This approach provides a reliable method for quantifying low-volatile analytes, which can be problematic to be monitored by GC. Two electrochemical reactions the methoxylation of 1-formylpyrrolidine and the oxidation of 3-bromobenzyl alcohol were investigated to demonstrate that the optimal conditions can be located within the pre-defined multi-dimensional reaction parameter spaces without intervention of the operator by using the stable noisy optimization by branch and FIT (SNOBFIT) algorithm.

electrosynthesis, Flow chemistry, Fourier transform infrared Spectroscopy, FT-IR, gas separation, self-optimization
0003-7028
38-50
Ke, Jie
e4b531d4-7642-4367-9a4e-d06f126c2599
Gao, Chuang
55768345-865e-4471-b24e-971ee60b001c
Folgueiras-Amador, Ana A.
080c345d-0a05-406a-bf7c-1939ca9c0aaa
Jolley, Katherine E.
c2bbafc9-c814-4183-b56f-6235474ae1d9
de Frutos, Oscar
4f5d355a-0871-4f19-bf0a-cf7e36d82a29
Mateos, Carlos
92ec7161-7e84-4eee-82c7-9d14ea77d39f
Rincón, Juan A.
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Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Poliakoff, Martyn
32e8faf7-3736-4052-8b7e-cf381dc76210
George, Michael W.
152757cb-31f4-4fba-82ac-b0d3c9926a36
Ke, Jie
e4b531d4-7642-4367-9a4e-d06f126c2599
Gao, Chuang
55768345-865e-4471-b24e-971ee60b001c
Folgueiras-Amador, Ana A.
080c345d-0a05-406a-bf7c-1939ca9c0aaa
Jolley, Katherine E.
c2bbafc9-c814-4183-b56f-6235474ae1d9
de Frutos, Oscar
4f5d355a-0871-4f19-bf0a-cf7e36d82a29
Mateos, Carlos
92ec7161-7e84-4eee-82c7-9d14ea77d39f
Rincón, Juan A.
5c4dac4c-9791-44d8-9ca5-b37da7add758
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Poliakoff, Martyn
32e8faf7-3736-4052-8b7e-cf381dc76210
George, Michael W.
152757cb-31f4-4fba-82ac-b0d3c9926a36

Ke, Jie, Gao, Chuang, Folgueiras-Amador, Ana A., Jolley, Katherine E., de Frutos, Oscar, Mateos, Carlos, Rincón, Juan A., Brown, Richard C.D., Poliakoff, Martyn and George, Michael W. (2022) Self-optimization of continuous flow electrochemical synthesis using Fourier transform infrared spectroscopy and gas chromatography. Applied Spectroscopy, 76 (1), 38-50. (doi:10.1177/00037028211059848).

Record type: Article

Abstract

A continuous-flow electrochemical synthesis platform has been developed to enable self-optimization of reaction conditions of organic electrochemical reactions using attenuated total reflection Fourier transform infrared spectroscopy (ATR FT-IR) and gas chromatography (GC) as online real-time monitoring techniques. We have overcome the challenges in using ATR FT-IR as the downstream analytical methods imposed when a large amount of hydrogen gas is produced from the counter electrode by designing two types of gas-liquid separators (GLS) for analysis of the product mixture flowing from the electrochemical reactor. In particular, we report an integrated GLS with an ATR FT-IR probe at the reactor outlet to give a facile and low-cost solution to determining the concentrations of products in gas-liquid two-phase flow. This approach provides a reliable method for quantifying low-volatile analytes, which can be problematic to be monitored by GC. Two electrochemical reactions the methoxylation of 1-formylpyrrolidine and the oxidation of 3-bromobenzyl alcohol were investigated to demonstrate that the optimal conditions can be located within the pre-defined multi-dimensional reaction parameter spaces without intervention of the operator by using the stable noisy optimization by branch and FIT (SNOBFIT) algorithm.

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Accepted/In Press date: 23 August 2021
Published date: 1 January 2022
Additional Information: Funding Information: The author(s) disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: We are grateful financial support from the EPSRC Programme Grant (EP/P013341/1) and from Hermes Fellowships Call 17 (JK) at the University of Nottingham and Eli Lilly and Company through the Lilly Research Awards Program (KEJ). Publisher Copyright: © The Author(s) 2021. Copyright: Copyright 2022 Elsevier B.V., All rights reserved.
Keywords: electrosynthesis, Flow chemistry, Fourier transform infrared Spectroscopy, FT-IR, gas separation, self-optimization

Identifiers

Local EPrints ID: 455764
URI: http://eprints.soton.ac.uk/id/eprint/455764
ISSN: 0003-7028
PURE UUID: 7cf9b998-4805-45c9-a6f7-385e1736e861
ORCID for Katherine E. Jolley: ORCID iD orcid.org/0000-0001-6223-9808
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 01 Apr 2022 22:30
Last modified: 18 Mar 2024 02:43

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Contributors

Author: Jie Ke
Author: Chuang Gao
Author: Ana A. Folgueiras-Amador
Author: Katherine E. Jolley ORCID iD
Author: Oscar de Frutos
Author: Carlos Mateos
Author: Juan A. Rincón
Author: Martyn Poliakoff
Author: Michael W. George

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