Synthesis of N,N'-Di-sec-Butyl p-Phenylene Diamine Catalyzed by Cu-Cr-La/γ-Al2O3

化学工业与工程

Chemcial Industry and Engineering

2016, Vol. 33

Issue (2) :45-51 DOI: 10.13353/j.issn.1004.9533.20141008

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Synthesis of N,N'-Di-sec-Butyl p-Phenylene Diamine Catalyzed by Cu-Cr-La/γ-Al₂O₃

Duan Yifan^1,2, Chen Ligong^1,2, Yan Xilong^1,2

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2. Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072, China

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Abstract

N,N'-Di-sec-butyl p-phenylene diamine (DBPD) was prepared from p-nitroaniline and butanone catalyzed by Cu-Cr-La/γ-Al₂O₃ in autoclave. The effects of the selection of catalyst, reaction temperature, reaction time, reaction pressure and the ratio of the reactants on the reaction were investigated. The optimum reaction condition for synthesis of DBPD was as follows: reaction temperature was 180 ℃, reaction time was 10 h, reaction pressure was 3.5 MPa, the mass ratio of p-nitroaniline and butanone was 1:4. The best reaction condition resulted in the target product with 97.0% purity and the conversion of p-nitroaniline was 100%. The catalysts could be reused three times without any significant loss in activity. On the basis of experiment in the laboratory, pilot experiment was carried out successfully.

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	Duan Yifan
	Chen Ligong
	Yan Xilong

Keywords： DBPD； Cu-Cr-La/γ-Al₂O₃； synthesis； catalyze

Received 2014-04-20;

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Duan Yifan, Chen Ligong, Yan Xilong.Synthesis of N,N'-Di-sec-Butyl p-Phenylene Diamine Catalyzed by Cu-Cr-La/γ-Al₂O₃[J] Chemcial Industry and Engineering, 2016,V33(2): 45-51

[1] Lehtonen J, Salmi T, Vuori A, et al. On the principles of modelling of homogeneous-heterogeneous reactions in the production of fine chemicals. A case study: Reductive alkylation of aromatic amines[J]. Org Process Res Dev, 1988, 2(2): 78-95
[2] Pan Z, Ding Y, Jiang D, et al. Study on Ni-Re-K/Al₂O₃ catalysts for synthesis of N,N'-di-sec-butyl p-phenylene diamine from p-nitroaniline and 2-butanone[J]. Appl Catal A-Gen, 2007, 330(10): 43-48
[3] 张晓云,刘亚丽,夏道宏. 汽油用液体抗氧剂[J]. 石油炼制与化工,2004, 35(5): 32-34 Zhang Xiaoyun, Liu Yali, Xia Daohong. Preparation of liquid antioxidant for gasoline[J]. Petroleum Processing and Petrochemicals, 2004, 35(5): 32-34 (in Chinese)
[4] 付春. N,N'-二仲丁基对苯二胺[J]. 精细与专用化学品, 2004, 12(1): 10-12 Fu Chun. N,N'-Di-sec-butyl-p-phenylenediamine[J]. Fine and Specialty Chemicals, 2004, 12(1): 10-12 (in Chinese)
[5] 刘公召,王晓青,杨娇. 乙醇溶剂法合成N,N'-二仲丁基对苯二胺的研究[J]. 化学世界, 2009, (8): 488-490 Liu Gongzhao, Wang Xiaoqing, Yang Jiao. Synthesis of N,N'-Di-sec-butyl-p-phenylenediamine in ethanol solvent[J]. Chemistry World, 2009, (8): 488-490 (in Chinese)
[6] 张苗苗, 王延臻, 刘艳平, 等. N,N'-二仲丁基对苯二胺抗氧剂的合成[J]. 青岛科技大学学报, 2005, 26(6): 484-489 Zhang Miaomiao, Wang Yanzhen, Liu Yanping, et al. Synthesis of N,N'-di-sec-butyl-p-phenylenediamine[J]. Journal of Qingdao University of Science and Technology, 2005, 26(6): 484-489(in Chinese)
[7] 王箴. 化工辞典[M]. 第2版. 北京:化学工业出版社, 1979
[8] Bramer H V, Davy L G, Clemens M L, et al. Process for preparing phenylene-diamine derivatives: US, 2323948[P]. 1943-07-13
[9] Schwettmann F N, Falls W. Alkylation method for producing phenylenediamines: US, 3384664[P]. 1968-02-21
[10] Patil N G, Roy D, Chaudhari A S, et al. Kinetics of reductive alkylation of p-phenylenediamine with methyl ethyl ketone using 3% Pt/Al₂O₃ catalyst in a slurry reactor[J]. Ind Eng Chem Res, 2007, 46(10): 3 243-3 254
[11] Dovell F S, Greenfield H. Base-Metal sulfides as reductive alkylation catalyst[J]. J Org Chem, 1964, 29(5): 1 265-1 267
[12] 张跃臻,魏奇. N,N'-二仲烷基对苯二胺的合成方法: CN, 1370768A[P]. 2002-09-25
[13] Prasad R, Singh P. Applications and preparation methods of copper chromite catalyst: A review[J]. Bulletin of Chemical Reaction Engineering & Catlalysis, 2011, 6(2): 63-113