Page 205 - 《精细化工》2020年第5期
P. 205

第 5 期                       石至平,等:  微溶性二氯联苯二胺的连续重氮化工艺                                   ·1055·


            不需要过量的酸抑制副反应。连续化工艺可以在更                                 platforms: Requirements, characteristics and applications[J]. Chemical
            少的盐酸用量下达到较高的收率。为了减少三废,                                 Society Reviews, 2010, 39(3): 1153-1182.
                                                               [7]   JÄHNISCH K, HESSEL V, LÖWE H, et al. Chemistry in microstructured
            降低成本,又能达到较高的重氮化收率,选择                                   reactors[J]. Angewandte Chemie, 2004, 43(4): 406-446.
            n(HCl)∶n(DCB) = 4∶1 制备重氮盐。                         [8]   CHEN Guangwen (陈光文), YUAN Quan (袁权). Micro-chemical
                                                                   technology[J]. Chemical Industry and Engineering Society of China
            2.5   连续化工艺长期运转的可行性
                                                                   Journal (化工学报), 2003, 54(4): 427-439.
                 在优化的合成条件下,即 DCB 质量浓度为                         [9]   DELVILLE  M  M  E,  NIEUWLAND  P  J,  JANSSEN  P,  et al.
            70 g/L、n(DCB)∶n(亚硝酸钠) = 1.0∶2.2、n(HCl)∶                Continuous flow azide formation: Osptimization and scale-up[J]. Chemical
                                                                   Engineering Journal, 2011, 167(2/3): 556-559.
            n(DCB) = 4∶1、进料温度为 20  ℃、流速为 1.1 m/s               [10]  HUANG Jinpei, SANG Funing, LUO Guangsheng, et al. Continuous
            的条件下,探讨连续化工艺长期运转的可行性。连                                 synthesis  of  Gabapentin  with  a  microreaction  system[J].  Chemical
            续化反应过程长期运行 12  h,未出现任何局部沉积                             Engineering Science, 2017, 173: 507-513.
                                                               [11]  WANG  Xincheng  (王新诚),  YUAN  Qiangyun  (袁抢云),  YUAN
            等现象,流速流量一直平稳,连续运行 12 h 时重氮                             Shaolan  (袁少岚),  et al.  Synthesis  of  iodo-substituted  aromatic
            化收率为 98.1%,与运行初期收率基本一致。这些                              compounds  in  a  micro-channel  reactor[J].Fine  Chemicals  (精细化
                                                                   工), 2014, 31(3): 398-400.
            结果表明,本文的工艺方案可以长期平稳运行,适
                                                               [12]  WOOTTON R C R, FORTT R, DE MELLO A J. On-chip generation
            合于工业化生产应用。                                             and  reaction  of  unstable  intermediates-monolithic  nanoreactors  for
                                                                   diazonium chemistry: Azo dyes[J]. Lab on A Chip, 2002, 2(1): 5-6.
            3   结论                                             [13]  ZHANG Shufen (张淑芬), LIANG Dong (梁栋), LV Rongwen (吕荣
                                                                   文),  et al.  A  continuous  preparation  method  for  chaotic  mixing  of
                                                                   spiral tube of water-soluble azo dye: 102618063A[P]. 2012-08-01.
                 基于连续化反应系统,实现了微溶性芳胺的重                          [14]  LIANG  Dong,  ZHANG  Shufen.  Numerical  and  experimental
            氮化,在 DCB 质量浓度为 70 g/L、n(DCB)∶n(亚硝                      investigation of the effect of geometrical parameters on the performance
            酸钠) = 1.0∶2.2、n(HCl)∶n(DCB) = 4∶1、进料温                  of  a  contraction-expansion  helical  mixer[J].  International  Journal  of
                                                                   Chemical Reactor Engineering, 2014, 12(1): 465-475.
            度为 20  ℃、流速为 1.1 m/s 的条件下,合成了 DCB                  [15]  WANG Fajun, HUANG Jinpei, XU Jianhong. Continuous-flow synthesis
            重氮盐,收率达到 98.3%。在本文实验条件下,连                              of azo dyes  in a microreactor  system[J].  Chemical Engineering  &
                                                                   Processing: Process Intensification, 2018, 127: 43-49.
            续化反应过程长期运行 12  h 未发生任何沉积等现
                                                               [16]  YU  Zhiqun,  YE  Xin,  XU  Qilin,  et al.  A  Fully  Continuous-flow
            象,收率平稳。对比间歇工艺,反应温度提高了近                                 process for the synthesis of p-cresol: Impurity analysis and process
            10  ℃,连续化工艺可以在室温下进行,降低了能耗;                             optimization[J].  Organic  Process  Research  &  Development,  2017,
                                                                   21: 1644-1650.
            而且酸的用量降低。相比于间隙过程,连续重氮化
                                                               [17]  AKWI F M, PAUL W. The in situ generation and reactive quench of
            过程不仅提高了反应效率,而且提高了反应收率,                                 diazonium  compounds  in  the  synthesis  of  azo  compounds  in
            降低了能耗,符合行业发展趋势,具有巨大的工业                                 microreactors[J]. Beilstein Journal of Organic Chemistry, 2016, 12:
                                                                   1987-2004.
            应用前景。                                              [18]  KOCKMANN  N,  KASTNER  J,  WOIAS  P.  Reactive  particle
                                                                   precipitation  in  liquid  microchannel  flow[J].Chemical  Engineering
            参考文献:                                                  Journal, 2008, 135: 110-116.
            [1]   MO Fanyang, DONG Guangbin, ZHANG Yan, et al. Recent applications   [19]  PENNEMANN H, FORSTER S, KINKEL J, et al. Improvement of
                 of arene diazonium salts in organic synthesis[J]. Organic & Biomolecular   dye  properties  of  the  azo  pigment  yellow  12  using  a  micromixer-
                 Chemistry, 2013, 11(10): 1582-1583.               based process[J]. Organic Process Research & Development, 2005,
            [2]   GAO Yunpeng (郜云鹏),WANG Jianbo (王剑波). Continuous flow   9(2): 188-192.
                 reaction of diazo compounds[J]. Chinese Journal of Organic Chemistry   [20]  LIU Dongzhi (刘东志), ZHANG Tianyong (张天永), WANG Shirong
                 (有机化学), 2018, 38(6): 1275-1291.                   (王世荣).  Pigment[M].  Beijing:Chemical  Industry  Press  (化学工业
            [3]   ATTOMA J, CAMARA T, BRUN P L, et al. Efficient transposition   出版社), 2002: 122-126.
                 of  the  Sandmeyer  reaction  from  batch  to  continuous  process[J].   [21]  ZHOU Xueqin (周雪琴), LIU Dongzhi (刘东志), LI Wei (李巍), et
                 Organic Process Research & Development, 2017, 21: 44-51.   al.  Tubular  mixer  and  continuous  preparation  method  for  azo
            [4]   ZHOU Chunlong (周春隆), MU Zhenyi (穆振义). Organic pigment   pigments: CN109845400[P]. 2019-10-16.
                 chemistry  and  technology[M].  Beijing:China  Petro-Chemical  Press   [22]  DU Yun (杜允), LIU Dongzhi (刘东志), SHI Zhiping (石至平), et al.
                 (中国石化出版社),2014: 23-26.                            Quantitative detection method for dichlorobenzidine diazonium salt
            [5]   YU  Zhiqun,  DONG  Hei,  XIE  Xiaoxuan,  et al.  Continuous-flow   concentration[J]. Modern Chemical Industry (现代化工), 2019, 39(4):
                 diazotization  for  efficient  synthesis  of  methyl  -2-(Chlorosulfonyl)   231-233.
                 benzoate: an example of inhibiting parallel side-reactions[J]. Organic   [23]  DU Yun (杜允).Study on the control mechanism of continuous
                 Process Research & Development, 2016, 20: 2116-2123.   synthesis  of  pigment  yellow  14[D].Tianjin:Tianjin  University
            [6]   MARK D, HAEBERLE S, ROTH G, et al. Microfluidic lab-on-a-chip     (天津大学), 2019.
   200   201   202   203   204   205   206   207   208   209   210