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·1500· 精细化工 FINE CHEMICALS 第 36 卷

1, 3, 4-thiadiazole and 1, 3, 4-oxadiazole moiety[J]. Bioorganic and [17] Sekhon B S. Chiral pesticides[J]. Journal of Pesticide Science, 2009,
Medicinal Chemistry, 2008, 16(7): 3632-3640. 34(1): 1-12.
[11] Chen C J, Song B A, Yang S, et al. Synthesis and antifungal activities [18] Yang M C, Peng C, Huang H, et al. Organocatalytic asymmetric
of 5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-thiadiazole and synthesis of spiro-oxindole piperidine derivatives that reduce cancer
5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-oxadiazole derivatives[J]. cell proliferation by inhibiting MDM2-p53 interaction[J]. Organic
Bioorganic and Medicinal Chemistry, 2007, 15(12): 3981-3989. Letters, 2017, 19 (24): 6752-6755.
[12] Gan X H, Hu D Y, Chen Z, et al. Synthesis and antiviral evaluation [19] Han X, Zhou H B, Dong C. Applications of chiral squaramides: from
of novel 1, 3, 4-oxadiazole/thiadiazole-chalcone conjugates[J]. asymmetric organocatalysis to biologically active compounds[J]. The
Bioorganic and Medicinal Chemistry Letters, 2017, 27: 4298-4301. Chemical Record, 2016, 16(2): 897-906.
[13] Wu W N, Tai A Q, Chen Q, et al. Synthesis and antiviral bioactivity [20] Liu B Y, Zhao D S, Xu D Q, et al. Amide ionic liquids(AILs)/
of novel 2-substituted methlthio-5-(4-amino-2-methylpyrimidin-5-yl)-1, L-proline synergistic catalyzed asymmetric Mannich reactions[J].
3, 4-thiadiazole derivatives[J]. Journal of Heterocyclic Chemistry, Chemical Research in Chinese Universities, 2007, 23(2): 163-168.
2015, 53: 2243-2246. [21] Bai S, Liu S, Zhu Y Y, et al. Asymmetric synthesis and antiviral
[14] Zhang K K, Liang X P, He M, et al. One-pot synthesis of novel chiral activity of novel chiral amino-pyrimidine derivatives[J]. Tetrahedron
β-amino acid derivatives by enantioselective Mannich reactions Letters, 2018, 59: 3179-3183.
catalyzed by squaramide cinchona alkaloids[J]. Molecules, 2013, [22] Bai S, Liu S, Zhu Y Y, et al. Antiviral bioactivity of chiral β-amino
18(6): 6142-6152. acid ester derivatives synthesized through a one-pot, solvent-free
[15] Williams A. Opportunities for chiral agrochemicals[J]. Pest Science, asymmetric mannich reaction[J]. Synlett, 2018, 29(22): 1921-1925.
1996, 46(1): 3-9. [23] Bai S, Liu S, Zhu Y Y, et al. Cinchona alkaloid thiourea-catalyzed
[16] Massey M P R, Tandy M J. Challenges and frustrations in the one-pot synthesis and bioselective activities of β-amino acid ester
separation and analysis of chiral agrochemicals[J]. Chirality, 1994, derivatives containing a pyrimidine moiety[J]. Heterocycles, 2018,
6(2): 63-71. 96(8): 1383-1397.

（上接第 1493 页） phenylene-terephthalamide) and improving performance for its
fiber[D]. Shanghai: Donghua University (东华大学), 2015.
（2）小试结果说明，负载型镍催化剂单批次损
[6] Lv Yongmei (吕咏梅). Production status and market analysis of
耗量只有 0.2%，而雷尼镍催化剂单批次损耗量达到 phenylamine in China [J]. Fine Chemical Industrial Raw Materials &
了 0.5%；水代替醇类作溶剂可进一步降低生产成 Intermediates (精细化工原料及中间体), 2009, (4): 31-34.
本。催化剂套用后期，使用负载型催化剂合成的对 [7] Chu Zheng (储政). Green process for synthesis of p-phenylenediamine
by catalytic hydrogenation of p-nitroaniline[J]. Petrochemical
苯二胺质量分数更高。 Technology (石油化工), 2012, 41(6): 637-640.
（3）中试实验结果说明，小试得到的实验条件 [8] Chang Qing (常青). Preparation method of o-phenylenediamine by
可行。根据小试和中试结果表明，采用负载型镍催 hydrogenation of o-nitroaniline using supported nickel catalyst:
CN106892827A [P]. 2017-06-17.
化剂，较理想的工业化工艺条件为：温度 110 ℃，
[9] Tang Qin (唐琴), Xu Lin (徐林), Ding Kehong (丁克鸿), et al. Study
停留时间 1 h，压力 2.0 MPa，搅拌转速 800 r/min， on p-phenylenediamine preparation by catalytic hydrogenation[J].
起始催化剂用量 10%，催化剂损耗 0.2%。 Chlor-Alkali Industry (氯碱工业), 2010, 46(9): 23-25.
（4）水作溶剂并套用后废水排放量很少，VOC [10] Zhang Yue (张钺), Zhang Qianhua (张谦华), Chen Gensheng (陈根
生), et al. Study on the preparation of p-phenylenediamine by liquid
处理量大大减少，降低了环保成本，从源头上杜绝
catalytic hydrogenation [J]. Henan Chemical Industry (河南化工),
了环保问题的产生。 2011, 28(5): 33-35.
[11] Yang Wei (杨薇), Wu Limei (武丽梅), Guo Zhifeng (郭志锋), et al.
参考文献： Kinetics of catalytic hydrogenation of p-phenylenediamine in liquid
[1] Yang Hongde (杨洪德), Yuan Yingchao (元英超). The synthesis of phase on raney Ni catalyst[J]. Industrial Catalysis (工业催化), 2011,
2, 5-diaminobenzenesulfonic acid and its application in dyestuffs[J]. 19(10): 61-65.
Dyestuffs and Coloration (染料与染色), 2011, 48(2): 41-44. [12] Li Kuanyi (李宽义). Production methods of p-phenylenediamine by
[2] Shen Changzhou (沈长洲), Han Lihua (韩利华), Zhang Xiuling (张 Pa-C catalytic hydrogenation under low pressure: CN1475475 [P].
秀玲). Improved of process dye of paraphenyldiamine[J]. Heibei 2004-02-18.
Chemical Engineering and Industry (河北化工), 2001, (3): 26-27. [13] Liu Chunyang (刘春洋). Synthesis of Ru-silica aerogel and its
[3] Li Zheng ( 李政 ). The synthesis and properties of new performance on hydrogenation of p-phenylenediamine[D]. Shanghai:
disazocondenation pigments[D]. Tianjin: Tianjin University (天津大 East China University of Science and Technology (华东理工大学),
学), 2016. 2018.
[4] Li Jun (李君), Jiang Yi (蒋毅), Cheng Jiyuan (程及源). Synthesis of [14] Standardization Administration of the People's Republic of China (中
p-phenylenediamine derivatives as antiaging agents[J]. Chinese 国国家标准 化管理委员 会 ). GB/T 25789—2010:
Journal of Synthetic Chemistry (合成化学), 2000, 8(1): 34-38. p-Phenylenediamine [S]. Beijing: Standards Press of China (中国标
[5] Kong Haijuan (孔海娟). Study on the polymerization of poly-(p- 准出版社), 2010: 1-5.