MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis

Andry Tahina Rabeharitsara; Henri Rakotondrina; Nambinina Richard Randriana; Soloniaina Rakotoarijaona; Hanitraniaina Marie Ratsimba; Rakotomamonjy Pierre

doi:doi:10.11648/j.ajaic.20230702.11

MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis

Andry Tahina Rabeharitsara, Henri Rakotondrina, Nambinina Richard Randriana, Soloniaina Rakotoarijaona, Hanitraniaina Marie Ratsimba, Rakotomamonjy Pierre

Published in American Journal of Applied and Industrial Chemistry (Volume 7, Issue 2)

Received: 4 August 2023 Accepted: 23 August 2023 Published: 13 September 2023

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Abstract

The 3-methyl-3-sulfanylbutan-1-ol (MSB) is a thiol molecule which could be used as food additive flavor agent and encountered in the white wine, in the coffee perfume, in the passion fruit and in the cat urine where it’s the responsible of its strong odor characteristics. Thus, this manuscript treated first the valorization of the cat-litters by extracting their MSB molecules using the ethanol-90° solvent. The number of the extraction per sample, its duration and the rinse cycle number are three factors influencing the extraction efficiency. In any case, the ethanol-90° extraction of the MSB molecule is interesting and allow to recover an MSB solution which concentration was deduced by the sulfur titration according to a BaCl₂ precipitation procedure. Then, the second part of this manuscript treated the study of the esterification-addition reaction between the citric acid molecules and the MSB molecules. A titration procedure was established allowing to follow the sulfur concentration during this esterification-addition reaction. The results of these experimentations permitted not only to establish a kinetic study of this reaction but also to purpose some reactional mechanism where it was discovered that the sulfur atom of the MSB molecule play a fundamental role during this citric acid esterification reaction. Additionally, the kinetic parameters indicated that the protonic acid H⁺ concentration, the citric acid concentration and the MSB molecule concentration influenced the speed of this esterification reaction between the citric acid molecules and the MSB molecules. Finally, using the results and experimental conditions of the esterification reaction, the third part of this manuscript was dedicated to the synthesis of a material based on black citric acid polymers (pn), pozzolana and citric acid named PPCA (pn-pozzolana-citric-acid) which could play the role of a cat-litter.

Published in	American Journal of Applied and Industrial Chemistry (Volume 7, Issue 2)
DOI	10.11648/j.ajaic.20230702.11
Page(s)	25-37
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

PPCA, 3-Methyl-3-Sulfanylbutan-1-ol (MSB), Citric Acid, Esterification, Acid Sites, Basic Sites

References

[1]	ANDRIAMANANTSOA Havosoa – «Valorisation Des Pneus Usages Non Réutilisables Par L’intermédiaire De L’acide Citrique Et De L’éthanolate De Fer II» - Mémoire de fin d’étude en vue de l’obtention du diplôme de Licence en Génie des Procédés Chimiques et Industriels. Ecole Supérieure Polytechnique d’Antananarivo E. S. P. A – Université d’Antananarivo. Promotion 2022.
[2]	Rabeharitsara Andry Tahina, Raharilaza Paulin Merix, Randriana Richard Nambinina – Chemical Process Engineering Department (E. S. P. A), Antananarivo University – Madagascar – “Esterification Between Citric Acid and Pumpkin Pips’ Organic Molecules – Esters Hydrolysis and Esters Used as Hydrocarbons Additives” - American Journal of Applied Chemistry in Vol. 6, Issue Number 3, June 2018. doi: 10.11648/j.ajac.20180603.12.
[3]	Raharilaza Paulin Merix - "Estérification entre les molécules d’acide citrique et les molécules organiques des graines de courges - hydrolyse et valorisations des esters comme additifs des hydrocarbures" – [Esterification between citric acid molecules and organic molecules of pumpkin seeds - hydrolysis and valuation of esters as hydrocarbon additives] - Mémoire de fin d’étude en vue de l’obtention du diplôme de Licence en Génie Chimique. E. S. P. A. Université d’Antananarivo. Promotion 2017.
[4]	Rabeharitsara Andry Tahina, Raherimandimby Jaochim, Randriana Nambinina Richard– Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar -“Trans-Esterification Between Citric Acid and Peanut Oil at Low pH and Ambient Temperature Catalyzed by Citric Acid and Sulfuric Acid Protonic Acid-H+” - American Journal of Applied Chemistry Volume 8, Issue 4, August 2020, Pages: 100-116 Received: Jul. 12, 2020; Accepted: Jul. 25, 2020; Published: Aug. 13, 2020.
[5]	Raherimandimby Jaochim - "Synthese De Biodiesel Par Transesterification De L’huile D’arachide Avec La Fonction Alcool De L’acide Citrique, Catalysée Par Ses Sites Acides Protoniques H+ Et Ceux Des H+/H2SO4 Eventuellement Supportés Sur Du Bois De Pin Seché BSH+" – [Synthesis of Biodiesel by Transesterification of Peanut Oil with the Alcohol Function of Citric Acid, Catalyzed by Its H+ Proton Acid Sites and Those of H+/H2SO4 Possibly Supported on BSH+ Seasoned Pinewood] - Mémoire de fin d’étude en vue de l’obtention du diplôme de Licence en Génie Chimique. E. S. P. A. Université d’Antananarivo. Promotion 2020.
[6]	Rabeharitsara Andry Tahina, Ravomialisoa Ernestine, Randriana Nambinina Richard – “Synthesis of Capsicum chinense citric acid esters-Its methanol trans-esterification investigations with hplc analysis and Its valorization as gels-crystals Ca-salts” – American Journal of applied chemistry – volume 9, issue 6, December 2021, pages: 221-237 Received: Nov. 28, 2021; accepted: Dec. 16, 2021; published: Dec. 31, 2021.
[7]	Rabeharitsara Andry Tahina – “Trans-Esterification With Methanol Of Capsicum Chinense’s Citric Acid Ester Solution Its Calcium Gel And Crystal Salts Synthesis” 11th Edition Of International Conference On Catalysis, Chemical Engineering And Technology” Online conference held on may 16-17, 2022 – Magnus group conferences and organizing committee.
[8]	Rabeharitsara Andry Tahina, Rakotonanahary Lovasoa Carolia Sabrinah, Ratsimba Marie Hanaitriniaina, Randriana Nambinina Richard, Robijaona Baholy, Rakotomamonjy Pierre – “Determining Of The Constituent Molecules Of The Strychnos Spinosa Pips By Extraction With Citric Acid Esterification Procedure” – American Journal of Applied Chemistry – Pages 21-32, Feb. 24, 2023 doi: 10.11648/j.ajac.20231101.13.
[9]	Rabeharitsara Andry Tahina, Randriamalala Ando Princia, Randriana Nambinina Richard, Robijaona Baholy, Ratsimba Marie Hanitriniaina – Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar - “Valorization of the pn-pozzolana to the synthesis of Fe-pn-pozzolana study – Application to the synthesis of the Fe-pn-SiO2“ – American Journal of Polymer Science and Technology – Volume 8; Issue N°2 – June 2022.
[10]	Rabeharitsara Andry Tahina, Rovatahianjanahary Behevitra, Randriana Nambinina Richard – Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar - «Pine Wood Powder Treatment To BXH+ Homogeneous Catalyst (H+/H2SO4) Supported On Its Aromatics And PNA – Application In Black Citric Acid Polymer Synthesis» - American Journal of Polymer Science and Technology. Vol. 4, No. 1, 2018, pp. 1-27. doi: 10.11648/j.ajpst.20180401.11.
[11]	Andriambola Sammy Eric – «Valorisation de l’acide citrique en polymères et en sels de mono- di- et tri-ammonium». Mémoire de fin d’étude en vue de l’obtention du diplôme d’Ingénieur en Génie Chimique. E. S. P. A. Université d’Antananarivo. Promotion 2013.
[12]	Rabeharitsara, Andry Tahina, Rabemananjara Nicole, Randriana Nambinina Richard - Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar - «Black Citric Acid Polymer (PN) Pozzolana Activated- Na-PN-Pozzolana-CE Material Synthesis Tested As Cationic Exchanger» - American Journal of Applied Chemistry; Volume7, issue 6, December 2019, Pages: 145-160.
[13]	Rabeharitsara Andry Tahina, Andriamitantsoa Havosoa, Randriana Nambinina Richard, Robijaona Baholy, Ratsimba Marie Hanitriniaina – Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar – “Study of Esterification Between the Used Tire and Citric Acid Molecules” - American Journal of Applied Chemistry, Vol. 10, Issue Number 5, October 2022.
[14]	Rabeharitsara Andry Tahina, Rabearimihaja Phandry Nomena Ndjiva – Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar – “Betacarotenes Dosage by Hydrofluoric Acid Solution and Validation of This New Process by SPC”. American Journal of Applied Chemistry. Vol. 4, No. 3, 2016, pp. 91-96. doi: 10.11648/j.ajac.20160403.14.
[15]	Rabearimihaja Phandry Taryh Nomena Ndjiva - «Valorisation Du Betacarotene Extrait De L’huile De Palme Brute Par De L’acide Acetique Pour La Determination Des Teneurs En Eau De Produits Petroliers (Gazole /Fuel-Oil) Et Dosage Des Teneurs En Betacarotene Par De L’acide Fluorhydrique» - [Valorization of Betacarotene Extracted from Crude Palm Oil by Acetic Acid for the Determination of Water Content of Petroleum Products (Diesel/Fuel Oil) and Determination of Betacarotene Content by Hydrofluoric Acid].- Mémoire de fin d’Etudes en vue de l’obtention du Diplôme de Master Titre Ingénieur en Génie des Procédés chimiques et Industriels - Ecole Supérieure Polytechnique Antananarivo. Université d’Antananarivo – Promotion 2015.

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Andry Tahina Rabeharitsara, Henri Rakotondrina, Nambinina Richard Randriana, Soloniaina Rakotoarijaona, Hanitraniaina Marie Ratsimba, et al. (2023). MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. American Journal of Applied and Industrial Chemistry, 7(2), 25-37. https://doi.org/10.11648/j.ajaic.20230702.11

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ACS Style

Andry Tahina Rabeharitsara; Henri Rakotondrina; Nambinina Richard Randriana; Soloniaina Rakotoarijaona; Hanitraniaina Marie Ratsimba, et al. MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. Am. J. Appl. Ind. Chem. 2023, 7(2), 25-37. doi: 10.11648/j.ajaic.20230702.11

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AMA Style

Andry Tahina Rabeharitsara, Henri Rakotondrina, Nambinina Richard Randriana, Soloniaina Rakotoarijaona, Hanitraniaina Marie Ratsimba, et al. MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. Am J Appl Ind Chem. 2023;7(2):25-37. doi: 10.11648/j.ajaic.20230702.11

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@article{10.11648/j.ajaic.20230702.11,
  author = {Andry Tahina Rabeharitsara and Henri Rakotondrina and Nambinina Richard Randriana and Soloniaina Rakotoarijaona and Hanitraniaina Marie Ratsimba and Rakotomamonjy Pierre},
  title = {MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {7},
  number = {2},
  pages = {25-37},
  doi = {10.11648/j.ajaic.20230702.11},
  url = {https://doi.org/10.11648/j.ajaic.20230702.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20230702.11},
  abstract = {The 3-methyl-3-sulfanylbutan-1-ol (MSB) is a thiol molecule which could be used as food additive flavor agent and encountered in the white wine, in the coffee perfume, in the passion fruit and in the cat urine where it’s the responsible of its strong odor characteristics. Thus, this manuscript treated first the valorization of the cat-litters by extracting their MSB molecules using the ethanol-90° solvent. The number of the extraction per sample, its duration and the rinse cycle number are three factors influencing the extraction efficiency. In any case, the ethanol-90° extraction of the MSB molecule is interesting and allow to recover an MSB solution which concentration was deduced by the sulfur titration according to a BaCl2 precipitation procedure. Then, the second part of this manuscript treated the study of the esterification-addition reaction between the citric acid molecules and the MSB molecules. A titration procedure was established allowing to follow the sulfur concentration during this esterification-addition reaction. The results of these experimentations permitted not only to establish a kinetic study of this reaction but also to purpose some reactional mechanism where it was discovered that the sulfur atom of the MSB molecule play a fundamental role during this citric acid esterification reaction. Additionally, the kinetic parameters indicated that the protonic acid H+ concentration, the citric acid concentration and the MSB molecule concentration influenced the speed of this esterification reaction between the citric acid molecules and the MSB molecules. Finally, using the results and experimental conditions of the esterification reaction, the third part of this manuscript was dedicated to the synthesis of a material based on black citric acid polymers (pn), pozzolana and citric acid named PPCA (pn-pozzolana-citric-acid) which could play the role of a cat-litter.},
 year = {2023}
}

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TY  - JOUR
T1  - MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis
AU  - Andry Tahina Rabeharitsara
AU  - Henri Rakotondrina
AU  - Nambinina Richard Randriana
AU  - Soloniaina Rakotoarijaona
AU  - Hanitraniaina Marie Ratsimba
AU  - Rakotomamonjy Pierre
Y1  - 2023/09/13
PY  - 2023
N1  - https://doi.org/10.11648/j.ajaic.20230702.11
DO  - 10.11648/j.ajaic.20230702.11
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 25
EP  - 37
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20230702.11
AB  - The 3-methyl-3-sulfanylbutan-1-ol (MSB) is a thiol molecule which could be used as food additive flavor agent and encountered in the white wine, in the coffee perfume, in the passion fruit and in the cat urine where it’s the responsible of its strong odor characteristics. Thus, this manuscript treated first the valorization of the cat-litters by extracting their MSB molecules using the ethanol-90° solvent. The number of the extraction per sample, its duration and the rinse cycle number are three factors influencing the extraction efficiency. In any case, the ethanol-90° extraction of the MSB molecule is interesting and allow to recover an MSB solution which concentration was deduced by the sulfur titration according to a BaCl2 precipitation procedure. Then, the second part of this manuscript treated the study of the esterification-addition reaction between the citric acid molecules and the MSB molecules. A titration procedure was established allowing to follow the sulfur concentration during this esterification-addition reaction. The results of these experimentations permitted not only to establish a kinetic study of this reaction but also to purpose some reactional mechanism where it was discovered that the sulfur atom of the MSB molecule play a fundamental role during this citric acid esterification reaction. Additionally, the kinetic parameters indicated that the protonic acid H+ concentration, the citric acid concentration and the MSB molecule concentration influenced the speed of this esterification reaction between the citric acid molecules and the MSB molecules. Finally, using the results and experimental conditions of the esterification reaction, the third part of this manuscript was dedicated to the synthesis of a material based on black citric acid polymers (pn), pozzolana and citric acid named PPCA (pn-pozzolana-citric-acid) which could play the role of a cat-litter.
VL  - 7
IS  - 2
ER  -

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Author Information

Andry Tahina Rabeharitsara

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar
Henri Rakotondrina

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar
Nambinina Richard Randriana

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar
Soloniaina Rakotoarijaona

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar
Hanitraniaina Marie Ratsimba

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar
Rakotomamonjy Pierre

Chemical Process Engineering Department (E. S. P. A), Antananarivo University, Antananarivo, Madagascar

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APA Style

Andry Tahina Rabeharitsara, Henri Rakotondrina, Nambinina Richard Randriana, Soloniaina Rakotoarijaona, Hanitraniaina Marie Ratsimba, et al. (2023). MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. American Journal of Applied and Industrial Chemistry, 7(2), 25-37. https://doi.org/10.11648/j.ajaic.20230702.11

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ACS Style

Andry Tahina Rabeharitsara; Henri Rakotondrina; Nambinina Richard Randriana; Soloniaina Rakotoarijaona; Hanitraniaina Marie Ratsimba, et al. MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. Am. J. Appl. Ind. Chem. 2023, 7(2), 25-37. doi: 10.11648/j.ajaic.20230702.11

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AMA Style

Andry Tahina Rabeharitsara, Henri Rakotondrina, Nambinina Richard Randriana, Soloniaina Rakotoarijaona, Hanitraniaina Marie Ratsimba, et al. MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis. Am J Appl Ind Chem. 2023;7(2):25-37. doi: 10.11648/j.ajaic.20230702.11

Copy | Download

@article{10.11648/j.ajaic.20230702.11,
  author = {Andry Tahina Rabeharitsara and Henri Rakotondrina and Nambinina Richard Randriana and Soloniaina Rakotoarijaona and Hanitraniaina Marie Ratsimba and Rakotomamonjy Pierre},
  title = {MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {7},
  number = {2},
  pages = {25-37},
  doi = {10.11648/j.ajaic.20230702.11},
  url = {https://doi.org/10.11648/j.ajaic.20230702.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20230702.11},
  abstract = {The 3-methyl-3-sulfanylbutan-1-ol (MSB) is a thiol molecule which could be used as food additive flavor agent and encountered in the white wine, in the coffee perfume, in the passion fruit and in the cat urine where it’s the responsible of its strong odor characteristics. Thus, this manuscript treated first the valorization of the cat-litters by extracting their MSB molecules using the ethanol-90° solvent. The number of the extraction per sample, its duration and the rinse cycle number are three factors influencing the extraction efficiency. In any case, the ethanol-90° extraction of the MSB molecule is interesting and allow to recover an MSB solution which concentration was deduced by the sulfur titration according to a BaCl2 precipitation procedure. Then, the second part of this manuscript treated the study of the esterification-addition reaction between the citric acid molecules and the MSB molecules. A titration procedure was established allowing to follow the sulfur concentration during this esterification-addition reaction. The results of these experimentations permitted not only to establish a kinetic study of this reaction but also to purpose some reactional mechanism where it was discovered that the sulfur atom of the MSB molecule play a fundamental role during this citric acid esterification reaction. Additionally, the kinetic parameters indicated that the protonic acid H+ concentration, the citric acid concentration and the MSB molecule concentration influenced the speed of this esterification reaction between the citric acid molecules and the MSB molecules. Finally, using the results and experimental conditions of the esterification reaction, the third part of this manuscript was dedicated to the synthesis of a material based on black citric acid polymers (pn), pozzolana and citric acid named PPCA (pn-pozzolana-citric-acid) which could play the role of a cat-litter.},
 year = {2023}
}

Copy | Download

TY  - JOUR
T1  - MSB - 3-Methyl-3-Sulfanylbutan-1-Ol Extraction Its Esterification with Citric Acid and PPCA Materials Synthesis
AU  - Andry Tahina Rabeharitsara
AU  - Henri Rakotondrina
AU  - Nambinina Richard Randriana
AU  - Soloniaina Rakotoarijaona
AU  - Hanitraniaina Marie Ratsimba
AU  - Rakotomamonjy Pierre
Y1  - 2023/09/13
PY  - 2023
N1  - https://doi.org/10.11648/j.ajaic.20230702.11
DO  - 10.11648/j.ajaic.20230702.11
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 25
EP  - 37
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20230702.11
AB  - The 3-methyl-3-sulfanylbutan-1-ol (MSB) is a thiol molecule which could be used as food additive flavor agent and encountered in the white wine, in the coffee perfume, in the passion fruit and in the cat urine where it’s the responsible of its strong odor characteristics. Thus, this manuscript treated first the valorization of the cat-litters by extracting their MSB molecules using the ethanol-90° solvent. The number of the extraction per sample, its duration and the rinse cycle number are three factors influencing the extraction efficiency. In any case, the ethanol-90° extraction of the MSB molecule is interesting and allow to recover an MSB solution which concentration was deduced by the sulfur titration according to a BaCl2 precipitation procedure. Then, the second part of this manuscript treated the study of the esterification-addition reaction between the citric acid molecules and the MSB molecules. A titration procedure was established allowing to follow the sulfur concentration during this esterification-addition reaction. The results of these experimentations permitted not only to establish a kinetic study of this reaction but also to purpose some reactional mechanism where it was discovered that the sulfur atom of the MSB molecule play a fundamental role during this citric acid esterification reaction. Additionally, the kinetic parameters indicated that the protonic acid H+ concentration, the citric acid concentration and the MSB molecule concentration influenced the speed of this esterification reaction between the citric acid molecules and the MSB molecules. Finally, using the results and experimental conditions of the esterification reaction, the third part of this manuscript was dedicated to the synthesis of a material based on black citric acid polymers (pn), pozzolana and citric acid named PPCA (pn-pozzolana-citric-acid) which could play the role of a cat-litter.
VL  - 7
IS  - 2
ER  -

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