Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis

Andrés Felipe Guzmán Agudelo; Wander Y. Pérez-Sena; Nasreddine Kebir; Tapio Salmi; Luis Alberto Ríos; Sébastien Leveneur

doi:10.1016/j.ces.2020.115954

Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis

Andrés Felipe Guzmán Agudelo, Wander Y. Pérez-Sena, Nasreddine Kebir, Tapio Salmi, Luis Alberto Ríos, Sébastien Leveneur

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

20 Citations (Scopus)

Abstract

Polyurethane polymer is more and more famous because of its versatile properties. The current production process requires the use of isocyanate, which is a hazardous chemical. An alternative eco-friendly route of production is the aminolysis reaction between a cyclic-carbonate, from carbonated vegetable oil, and a diamine. Nevertheless, the kinetics of this reaction system is slow, which might be due to steric hindrance. In order to predict and evaluate this steric hindrance, different amines were tested for the aminolysis of carbonated methyl oleate. Four amines were used: n-butylamine, methylbutylamine, ethylbutylamine and dibutylamine. Kinetic models for the aminolysis with each amine were developed. A relationship between structure and reactivity of each substituent was found through the concept of Linear Free Energy Relationships.

Original language	English
Article number	115954
Journal	Chemical Engineering Science
Volume	228
DOIs	https://doi.org/10.1016/j.ces.2020.115954
Publication status	Published - 2020
MoE publication type	A1 Journal article-refereed

Keywords

NIPU
Cyclic carbonate
Aminolysis
Vegetable oils
Kinetic modeling
Structure reactivity

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10.1016/j.ces.2020.115954

http://www.sciencedirect.com/science/article/pii/S0009250920304863

Cite this

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title = "Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis",

abstract = "Polyurethane polymer is more and more famous because of its versatile properties. The current production process requires the use of isocyanate, which is a hazardous chemical. An alternative eco-friendly route of production is the aminolysis reaction between a cyclic-carbonate, from carbonated vegetable oil, and a diamine. Nevertheless, the kinetics of this reaction system is slow, which might be due to steric hindrance. In order to predict and evaluate this steric hindrance, different amines were tested for the aminolysis of carbonated methyl oleate. Four amines were used: n-butylamine, methylbutylamine, ethylbutylamine and dibutylamine. Kinetic models for the aminolysis with each amine were developed. A relationship between structure and reactivity of each substituent was found through the concept of Linear Free Energy Relationships.",

keywords = "NIPU, Cyclic carbonate, Aminolysis, Vegetable oils, Kinetic modeling, Structure reactivity",

author = "Agudelo, {Andr{\'e}s Felipe Guzm{\'a}n} and P{\'e}rez-Sena, {Wander Y.} and Nasreddine Kebir and Tapio Salmi and R{\'i}os, {Luis Alberto} and S{\'e}bastien Leveneur",

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year = "2020",

doi = "10.1016/j.ces.2020.115954",

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journal = "Chemical Engineering Science",

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TY - JOUR

T1 - Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis

AU - Agudelo, Andrés Felipe Guzmán

AU - Pérez-Sena, Wander Y.

AU - Kebir, Nasreddine

AU - Salmi, Tapio

AU - Ríos, Luis Alberto

AU - Leveneur, Sébastien

N1 - Post-print, 24 mån embargo, CC-BY-NC-ND begärt fulltext [email protected] (ALG)

PY - 2020

Y1 - 2020

N2 - Polyurethane polymer is more and more famous because of its versatile properties. The current production process requires the use of isocyanate, which is a hazardous chemical. An alternative eco-friendly route of production is the aminolysis reaction between a cyclic-carbonate, from carbonated vegetable oil, and a diamine. Nevertheless, the kinetics of this reaction system is slow, which might be due to steric hindrance. In order to predict and evaluate this steric hindrance, different amines were tested for the aminolysis of carbonated methyl oleate. Four amines were used: n-butylamine, methylbutylamine, ethylbutylamine and dibutylamine. Kinetic models for the aminolysis with each amine were developed. A relationship between structure and reactivity of each substituent was found through the concept of Linear Free Energy Relationships.

AB - Polyurethane polymer is more and more famous because of its versatile properties. The current production process requires the use of isocyanate, which is a hazardous chemical. An alternative eco-friendly route of production is the aminolysis reaction between a cyclic-carbonate, from carbonated vegetable oil, and a diamine. Nevertheless, the kinetics of this reaction system is slow, which might be due to steric hindrance. In order to predict and evaluate this steric hindrance, different amines were tested for the aminolysis of carbonated methyl oleate. Four amines were used: n-butylamine, methylbutylamine, ethylbutylamine and dibutylamine. Kinetic models for the aminolysis with each amine were developed. A relationship between structure and reactivity of each substituent was found through the concept of Linear Free Energy Relationships.

KW - NIPU

KW - Cyclic carbonate

KW - Aminolysis

KW - Vegetable oils

KW - Kinetic modeling

KW - Structure reactivity

U2 - 10.1016/j.ces.2020.115954

DO - 10.1016/j.ces.2020.115954

M3 - Article

SN - 0009-2509

VL - 228

JO - Chemical Engineering Science

JF - Chemical Engineering Science

M1 - 115954

ER -

Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis

Abstract

Keywords

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