A study on the alkylation of m-cresol with 1-decene over mesoporous silica supported tungstophosphoric acid (HPW)
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A study on the alkylation of m-cresol with 1-decene over mesoporous silica supported tungstophosphoric acid (HPW) Rami Doukeh1 · Daniela Popovici1 · Ancuța Trifoi2 · Mihaela Bombos4 · Ionuț Banu3 Received: 25 August 2020 / Accepted: 18 October 2020 © Akadémiai Kiadó, Budapest, Hungary 2020
Abstract Linear alkylcresols were synthesized in high yield by the alkylation of m-cresols with 1-decene in the presence of 25%HPW/SBA-15 catalyst. The physicochemical properties of the catalyst were investigated by means of N 2 adsorption/desorption measurements (textural properties: surface area, pore volume and average pore diameter) and thermal desorption of diethyl-amine (acidity and the acid strength distribution). HPW-loaded acid as well as the SBA-15 support displayed a mesoporous structure. The effects of the reaction time and the catalyst amount on the reaction were studied. The main monitored parameters were the conversion of m-cresol, yield of decylcresol isomers (ortho- and para-) and yield of polyakylated cresol. The results indicates that 25%HPW/SBA-15 catalyst has high catalytic activity, with the m-cresol conversion of 93.8% , at 160 °C with a reaction time of 150 min and a catalyst loading of 0.5 wt% m-Cresol was alkylated preferably in the para-position, the yield of 4-(decan-2yl)-3-methylphenol, after 150 min reaction time was 54.5%. Keywords m-cresol · alkylation · catalyst · 4-(decan-2yl)-3-methylphenol
* Ionuț Banu [email protected] 1
Petroleum-Gas University of Ploiesti, 39 Bucuresti Blvd., 100680 Ploiesti, Romania
2
Research Institute for Auxiliary Organic Products, 8 Carpati Street, No. 8, Medias, Romania
3
University Politehnica, Department of Chemical and Biochemical Engineering, 1‑7 Polizu Str, 011061 Bucharest, Romania
4
National Institute for Research Development for Chemistry and Petrochemistry ICECHIM Bucuresti, 202 Splaiul Independentei, 060021 Bucharest, Romania
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Reaction Kinetics, Mechanisms and Catalysis
Introduction The alkylation of aromatic compounds with olefins, halides or alcohols is an important process used in industry. Among the alkylation reactions, alkylation of cresols is very important because alkylated cresols and their derivatives are the most effective antioxidants and multifunctional stabilizers in fuels, lubricating oils and wide variety of oxygen sensitive materials. Moreover, some of the derivatives of the alkyl cresols exhibit promising characteristics due to the strong herbicidal, bactericidal and insecticidal activities [1, 2]. The alkylation of phenolic compounds with the above mentioned compounds is traditionally catalysed by inorganic Brønsted and Lewis acids, such as H2SO4, HF, AlCl3 and BF3 [3–5]. The reaction of phenol with olefins (hexene-1, cyclohexene, (heptene-1, cycloheptene, octene-1) in the presence of 94% sulphuric acid as catalyst, was studied by Saha et al. over the temperature range of 50–140 °C, at different molar ratio of phenol to olefin and a reaction time of 2 h. Sulphuric acid catalysed reaction of phe
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