1H NMR-based analytical method: A valid and rapid tool for the epoxidation processes

Tommaso Cogliano; Rosa Turco; Vincenzo Russo; Martino Di Serio; Riccardo Tesser

doi:10.1016/j.indcrop.2022.115258

¹H NMR-based analytical method: A valid and rapid tool for the epoxidation processes

Tommaso Cogliano, Rosa Turco^*, Vincenzo Russo, Martino Di Serio, Riccardo Tesser^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

Abstract

The present work aims to propose a ¹H NMR-based method for a rapid determination of conversion, yield, and selectivity in the epoxidation of organic substrates. Several experiments were carried out on different substrates and analyzed with both the proposed ¹H NMR method and the volumetric traditional ones for a useful comparison. The results obtained with the traditional methods were deeply studied to find a mathematical correlation between the absolute analytical error and the double bond or oxirane ring concentration. The same was done for the conversion and yield derived from the analytical determinations. Finally, the results obtained with the proposed ¹H NMR-based method on the epoxidation of methyl-oleate, as a model molecule, were compared with the results obtained by the traditional methods. A good agreement was obtained between the two classes of methods validating the proposed ¹H NMR method.

Original language	English
Article number	115258
Journal	Industrial Crops and Products
Volume	186
DOIs	https://doi.org/10.1016/j.indcrop.2022.115258
Publication status	Published - 15 Oct 2022
MoE publication type	A1 Journal article-refereed

Keywords

Epoxidation process
Epoxidized oils
Epoxy content
Iodine value
Quantitative H NMR-based analytical method
Wijs method

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10.1016/j.indcrop.2022.115258

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title = "1H NMR-based analytical method: A valid and rapid tool for the epoxidation processes",

abstract = "The present work aims to propose a 1H NMR-based method for a rapid determination of conversion, yield, and selectivity in the epoxidation of organic substrates. Several experiments were carried out on different substrates and analyzed with both the proposed 1H NMR method and the volumetric traditional ones for a useful comparison. The results obtained with the traditional methods were deeply studied to find a mathematical correlation between the absolute analytical error and the double bond or oxirane ring concentration. The same was done for the conversion and yield derived from the analytical determinations. Finally, the results obtained with the proposed 1H NMR-based method on the epoxidation of methyl-oleate, as a model molecule, were compared with the results obtained by the traditional methods. A good agreement was obtained between the two classes of methods validating the proposed 1H NMR method.",

keywords = "Epoxidation process, Epoxidized oils, Epoxy content, Iodine value, Quantitative H NMR-based analytical method, Wijs method",

author = "Tommaso Cogliano and Rosa Turco and Vincenzo Russo and {Di Serio}, Martino and Riccardo Tesser",

note = "Funding Information: The authors acknowledge the grant PRIN: Progetti di Ricerca di Interesse Nazionale – Bando 2017 – prot. number: 2017KBTK93 “CARDoon valorisation by InteGrAted biorefiNery ( CARDIGAN )” of Italian Ministero dell'Istruzione dell'Universit{\`a} e della Ricerca for the financial support. The authors are grateful to Solvay Italy for providing hydrogen peroxide. Publisher Copyright: {\textcopyright} 2022 Elsevier B.V.",

year = "2022",

month = oct,

day = "15",

doi = "10.1016/j.indcrop.2022.115258",

language = "English",

volume = "186",

journal = "Industrial Crops and Products",

issn = "0926-6690",

publisher = "Elsevier",

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T1 - 1H NMR-based analytical method

T2 - A valid and rapid tool for the epoxidation processes

AU - Cogliano, Tommaso

AU - Turco, Rosa

AU - Russo, Vincenzo

AU - Di Serio, Martino

AU - Tesser, Riccardo

N1 - Funding Information: The authors acknowledge the grant PRIN: Progetti di Ricerca di Interesse Nazionale – Bando 2017 – prot. number: 2017KBTK93 “CARDoon valorisation by InteGrAted biorefiNery ( CARDIGAN )” of Italian Ministero dell'Istruzione dell'Università e della Ricerca for the financial support. The authors are grateful to Solvay Italy for providing hydrogen peroxide. Publisher Copyright: © 2022 Elsevier B.V.

PY - 2022/10/15

Y1 - 2022/10/15

N2 - The present work aims to propose a 1H NMR-based method for a rapid determination of conversion, yield, and selectivity in the epoxidation of organic substrates. Several experiments were carried out on different substrates and analyzed with both the proposed 1H NMR method and the volumetric traditional ones for a useful comparison. The results obtained with the traditional methods were deeply studied to find a mathematical correlation between the absolute analytical error and the double bond or oxirane ring concentration. The same was done for the conversion and yield derived from the analytical determinations. Finally, the results obtained with the proposed 1H NMR-based method on the epoxidation of methyl-oleate, as a model molecule, were compared with the results obtained by the traditional methods. A good agreement was obtained between the two classes of methods validating the proposed 1H NMR method.

AB - The present work aims to propose a 1H NMR-based method for a rapid determination of conversion, yield, and selectivity in the epoxidation of organic substrates. Several experiments were carried out on different substrates and analyzed with both the proposed 1H NMR method and the volumetric traditional ones for a useful comparison. The results obtained with the traditional methods were deeply studied to find a mathematical correlation between the absolute analytical error and the double bond or oxirane ring concentration. The same was done for the conversion and yield derived from the analytical determinations. Finally, the results obtained with the proposed 1H NMR-based method on the epoxidation of methyl-oleate, as a model molecule, were compared with the results obtained by the traditional methods. A good agreement was obtained between the two classes of methods validating the proposed 1H NMR method.

KW - Epoxidation process

KW - Epoxidized oils

KW - Epoxy content

KW - Iodine value

KW - Quantitative H NMR-based analytical method

KW - Wijs method

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DO - 10.1016/j.indcrop.2022.115258

M3 - Article

AN - SCOPUS:85133332651

SN - 0926-6690

VL - 186

JO - Industrial Crops and Products

JF - Industrial Crops and Products

M1 - 115258

ER -

¹H NMR-based analytical method: A valid and rapid tool for the epoxidation processes

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Keywords

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