Using n-toluenesulfuric acid salts as esterification catalysts
DOI:
https://doi.org/10.15587/1729-4061.2013.16690Keywords:
esterification, catalyst (catalyst agent), n-toluenesulfonic acid salts, adipinic acid, acetic acid, 1-butanol, 3-methylbutan-1-olAbstract
The influence of n-toluenesulfonic acid salts on technological parameters of the process of acetic and adipinic acids esterification by 1-butanol and 3-methylbutan-1-ol has been analyzed in non-stationary conditions. It has been determined, that using these kinds of catalysts, as compared to n-toluenesulfonic acid, provides reducing the dibutyl adipate and alkylacytates synthesis duration, lower acid number of reaction products and higher acid conversion with the concentration rate, proportional to the p-TSA. Although there is no need for the high catalyst concentration for achieving the effect, still it allows faster esterification process. The research has shown that low content of water, added to reagents in amount of 3-4 mass %, can reduce the dibutyl adipate and alkylacytates production duration almost by half without worsening its technological parameters. The effect of water influence lies in improvement of salt-catalyst solubility in reaction mixture at the initial reaction phase, that probably cuts the induction period of forming the catalyst–substrate complex. Further increasing of water content in the output reaction mixture causes low values of acid conversion. A series of cationic activities of n-toluene sulfonic acid salt metals in reaction of acetic acid esterification by 3-methylbutan-1-ol has been singled out. It has been found out that using aluminum and stannum n-toluene sulfates provides better technological parameters, than when using n-toluene sulfonic acid. The research results prove the effectiveness of using n-toluenesulfonic acid salts as esterification catalystsReferences
- Otera, J. Esterification [Текст] / J.Otera. – Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 2003. – 303 c.
- Барштейн, В.С. Пластификаторы для полимеров [Текст] / В.С. Барштейн, В.И. Кирилович, Ю.Е. Носовский – М.: Химия, 1982. – 200 с.
- Силинг, М.И. Соединения титана как катализаторы этерификации и переэтерификации [Текст] / М.И. Силинг, Т.И. Ларина / Успехи химии. – 1996. – T.65(3). – C. 296-304.
- Пат. 049556 WO, МПК7 C07 C303/32, C07 C67/03, C07 C67/08, C07 C309/01. Process for the production of metal salts of trifluoromethane sulphonic acid and their use as esterification catalysts [Текст] / Finmans P., Hoell D., Vossler H.-J., Rozek M., Green M. (США); заявник і патентовласник SASOL Germany GMBH – №PCT/EP2004/013107; заявл. 18.11.04; опубл. 02.06.05.
- Yan-mei, S. Esterification and selective esterification in the presence of TiCl4 [Текст] / Shang Yan-mei, Li Jing, Zhang Ping, Song Zhi-guang, Li Ye-zhi, Huang Hua-min [Текст] // Chem. Res. Chin. Univ. – 2007. – №6. – C. 669-673.
- Li-Fang, Z. Preparation of new organotin compounds and their application to esterification reaction [Текст] / Zhao Li-Fang, Wang Hong-She, Miao Jian-Ying // Chin. J. Appl. Chem. – 2006. – № 11. – C. 1273-1277.
- Gang, L. Esterifications of carboxylic acid and alcohols catalyzed by Al2(SO4)318H2O under solvent-free condition [Текст] / Li Gang, Pang Wenhui // Кинетика и катализ. – 2010. – Т.51(4). – С. 583-589.
- Sun, H.-B. ZrOCl2•8H2O: An efficient, cheap and reusable catalyst for the esterification of acrylic acid and other carboxylic acids with equimolar amounts of alcohols [Текст] / Hong-Bin Sun, Ruimao Hua, Yingwu Yin // Мolecules. – 2006. – №11. – С. 263-271.
- Cardoso, A.L. Esterification of oleic acid for biodiesel production catalyzed by SnCl2: a kinetic investigation [Текст] / Abiney L. Cardoso, Soraia Cristina Gonzaga Neves, Marcio J. da Silva // Energies. – 2008. – №1. – Р. 79-92.
- Дзіняк, М.Б. Одержання бутил- і амілацетатів у присутності солей перфтор(4-метил-3,6-діоксаоктан)сульфонатної кислоти [Текст] /М.Б. Дзіняк, С.Р. Мельник, В.Л.Старчевський // Вісник Національного університету «Львівська політехніка». Хімія, технологія речовин та їх застосування. – 2011– №700. – С. 173-175.
- Jie, M. Esterification of chloroacetic acid and alcohols catalyzed by cupric p-toluenesulfonate [Текст] / Ma Jie, Jiang Heng, Gong Hong, Wang Rui // Bulletin of science and technology. – 2005. – V.21(2). – C. 123-128.
- Otera, J. (2003). Esterification. Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 303.
- Barshtein V.S., Kirilovich V.I, Nosovsky J.E. (1982) Plasticizers for polymers. Moscow, USSR: Chemie, 200.
- Siling М.I., Larina T.I. (1996). Titanium compounds as catalysts for esterification and transesterification / Uspekhi Khimii, 65(3), 296–304.
- Pat. 049556 WO, Int. Cl C07 C303/32, C07 C67/03, C07 C67/08, C07 C309/01. Process for the production of metal salts of trifluoromethane sulphonic acid and their use as esterification catalysts. Finmans P., Hoell D., Vossler H.-J., Rozek M., Green M. (USA); SASOL Germany GMBH – International Application №PCT/EP2004/013107; filing date 18.11.04; publication date 02.06.05.
- Shang Yan-mei, Li Jing, Zhang Ping, Song Zhi-guang, Li Ye-zhi, Huang Hua-min. (2007). Esterification and selective esterification in the presence of TiCl4. Chem. Res. Chin. Univ., 6, 669-673.
- Zhao Li-Fang, Wang Hong-She, Miao Jian-Ying. (2006). Preparation of new organotin compounds and their application to esterification reaction. Chin. J. Appl. Chem., 11, 1273-1277.
- Li Gang, Pang Wenhui. (2010). Esterifications of carboxylic acid and alcohols catalyzed by Al2(SO4)318H2O under solvent-free condition. Kinetics and Catalysis, 51(4), 583-589.
- Hong-Bin Sun, Ruimao Hua, Yingwu Yin. (2006). ZrOCl2•8H2O: An efficient, cheap and reusable catalyst for the esterification of acrylic acid and other carboxylic acids with equimolar amounts of alcohols. Мolecules, 11, 263-271.
- Abiney L. Cardoso, Soraia Cristina Gonzaga Neves, Marcio J. da Silva. (2008). Esterification of oleic acid for biodiesel production catalyzed by SnCl2: a kinetic investigation. Energies, 1, 79-92.
- M.B. Dzinyak, S.R. Melnyk, V.L. Starchevsky. (2011). Obtaining of butyl and amilacetate in the presence of salts of perfluoro(4-methyl-3,6-dioxaoctane)sulfonic acid // Visnyk of the National University "Lviv Polytechnic". Chemistry, technology materials and their applications, 700, 173-175.
- Ma Jie, Jiang Heng, Gong Hong, Wang Rui. (2005). Esterification of chloroacetic acid and alcohols catalyzed by cupric p-toluenesulfonate. Bulletin of science and technology, 21(2), 123-128.
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