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Vapor Phase Reaction of Benzene with γ-Butyrolactone for the Synthesis of α-Tetralone under Solid Acid Catalysis

Author: WangCunJin
Tutor: MaoJianXin
School: Zhejiang University
Course: Chemistry
Keywords: F-C reaction Microporous molecular sieves γ-butyrolactone α - tetralone Gas-solid reactions Fixed - bed reactor
CLC: TQ244.2
Type: Master's thesis
Year: 2010
Downloads: 76
Quote: 2
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Abstract


α-tetralone is an important synthetic intermediate, can be used antidepressant Sertraline contraceptives norethylnodrel - mestranol sheet, insecticides, carbaryl, plastic softeners such synthesis. The existing literature, tetrahydronaphthalene air oxidation method, as well as benzene and γ-butyrolactone under the catalysis of the AlCl 3 can generate α-tetralone, but the air oxidation of tetrahydronaphthalene low conversion rate the AlCl 3 catalyst corrosion equipment exists, the problem of environmental pollution and difficult to reuse, need further green the course of the reaction. In recent years, molecular sieve has received more attention in the acid-catalyzed reaction of FC. Molecular sieve is a solid acid, acidic, the rules of the channel as well as the large specific surface area, is widely used in the synthetic field of petrochemicals, fine chemicals. Modification and molecular sieve properties needed to change the amount of acid and pore structure. Zeolite has a higher thermal stability, and regenerated by a high temperature to burn off coke and lower industrial costs. This paper studies the reaction of benzene with γ-butyrolactone in a fixed bed reactor, made more systematic characterization of the physical and chemical properties of the catalyst, and the discussion under the conditions of acid-catalyzed reaction rule possible microscopic reaction mechanism . The main research content and results are as follows: 1. Impregnation of ZnCl 2 load γ-Al 2 O 3 and activated carbon surface, will heteropoly the acid H 3 of the PW 12 O 40 load to the 7-Al 2 O 3 of the surface, in the gas-solid phase reaction activity of the catalyst was evaluated in a fixed bed reactor, and the results show that: ① The 33.3% ZnCl 2 / γ-Al 2 O 3 and 33.3% of ZnCl 2 / C gas-solid phase benzene and γ-butyrolactone with high catalytic activity, but 33.3% H < sub> 3 PW 12 O 40 / γ-Al 2 O 3 can not catalyze the reaction . ② 33.3% ZnCl 2 / Al 2 O 3 the results of the reaction at different temperatures, at 300-360 ° C the range of The conversion rate and the temperature of the γ-butyrolactone was a negative relationship. low, the selectivity and yield of the α-tetralone product, in addition to propylbenzene, 2 - butenoic acid and α-tetralone there are still more than 30% of the product, the reaction mechanism is very complicated. Acidic zeolite benzene and γ-butyrolactone in the gas-solid phase reaction having apparent catalytic and catalytic results of the various molecular sieve there is a larger difference, but the major product was propylbenzene (including cumene and n-propylbenzene) , 2 - butenoic acid, and α-tetralone ketone. HZSM5 Zeolite generate tetrahydronaphthalene ketone has a high selectivity and stability, there is provided a new method on a synthetic α-tetrahydronaphthalene ketone. Explored in detail the impact of the reaction conditions on the conversion rate, yield or selectivity, and proposed possible reaction mechanism; addition, HZSM5 (Si / Al = 50) hydrothermal treatment, heat treatment, phosphate modified and rare earth modified also carried out a more detailed study. The main results: ① HZSM5 Zeolite catalytic gas-solid phase benzene and γ-butyrolactone reaction to alumina ratio Si / Al = 50 results of the reaction, HZSM5 (Si / Al = 50) appeared during the reaction inactivation phenomenon, high temperature pass into the air or O 2 to burn off coke the catalyst may be regenerated by having good repeatability. ② phosphoric acid modified, water, heat treatment, heat treatment, and REE modified method can improve the catalytic activity of the molecular sieve, while the product selectivity is not greatly affected. With water and heat treatment and heat treatment modified to obtain a high activity and stability. ③ benzene and γ-butyrolactone and the gas-solid phase reaction to the possible reaction mechanism: gamma-butyrolactone first ring-opening reaction with benzene 4-phenyl-butyric acid, 4 - phenyl-butyric acid intramolecular acylation generated by the reaction, ring closure of the α-tetralone. Benzene and γ-butyrolactone gas-solid reactions may ER mechanism. Generated during the reaction of propylene and 2 - butenoic acid may be polymerized, is the main reason for the zeolite deactivation. . Were used the NH 3 -TPD, BET, XRD and O 2 -TG ??acidic molecular sieves and modified zeolite were characterized, the results show that: (1) different silicon Al ratio HZSM5 molecular sieves, silica-alumina than smaller the greater the amount of acid. ② REE modified, high temperature calcination, hydrothermal treatment, and a phosphoric acid modified method can reduce the number of HZSM5 Zeolite the total amount of acid and strong acid and weak acid sites, but does not affect the surface of the phase structure of HZSM5 Zeolite ③ HZSM5 (Si / Al = 50) before and after the reaction and after the regeneration, the surface of the phase structure is not changed, indicating that the zeolite deactivation mainly product coke or coke.

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aromatic compounds > Aromatic aldehydes,aromatic ketones and their derivatives,quinones and their derivatives > Aromatic ketones and their derivatives
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