Production of 2-chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine

DONG Qingqing; YU Wanjin; HU Meng; LIN Shengda; LIU Wucan; ZHANG Jianjun; CHENG Dangguo; CHEN Fengqiu

doi:10.11949/j.issn.0438-1157.20151013

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Production of 2-chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine

更新时间：2025-12-10

- Production of 2-chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine
- CIESC Journal Issue 12, Pages: 4843-4849(2015)
- 作者机构：
  
  1. 浙江大学化学工程与生物工程学院,浙江,杭州,310027
  2. 浙江省化工研究院, 国家ODS替代品工程技术研究中心, 浙江省化工新材料重点实验室,浙江,杭州,310023
- 作者简介：
- 基金信息：
- DOI：10.11949/j.issn.0438-1157.20151013
  CLC： TQ032.4}
- Online First：05 December 2015，
  
  Published：05 December 2015
- 稿件说明：
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DONG Qingqing, YU Wanjin, HU Meng, et al. Production of 2-chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine[J]. CIESC Journal, 2015, (12): 4843-4849.
DOI：

DONG Qingqing, YU Wanjin, HU Meng, et al. Production of 2-chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine[J]. CIESC Journal, 2015, (12): 4843-4849. DOI： 10.11949/j.issn.0438-1157.20151013.

摘要

研究了以3-甲基吡啶、氟化氢和氯气为原料在流化床反应器中一步法气相氯氟化反应制备2-氯-5-三氟甲基吡啶和3-三氟甲基吡啶的工艺

并对催化剂进行了筛选和考评

发现CrO-Al、CrCl-Al的活性较佳。以CrO-Al为催化剂

空速为288 h-1

温度为300℃时

2-氯-5-三氟甲基吡啶和3-三氟甲基吡啶的总收率最高

为66.6%

且失活催化剂在350℃

氮气和空气的体积比为1:1的混合气体下再生后

其催化活性基本可以恢复

2-氯-5-三氟甲基吡啶和3-三氟甲基吡啶的总收率均保持在66%左右。根据实验结果提出了反应机理和结焦机理。对催化剂进行了BET、TG和NH3-TPD表征

发现催化剂失活的主要原因是积炭覆盖了催化剂表面以及孔道

使催化剂强酸中心大量减少所致。

Abstract

2-Chloro-5-trifluoromethylpyridine and 3-trifluoromethylpyridine are produced by β-picoline reacting with chlorine and hydrogen fluoride in a fluidized-bed reactor. The total yield of 2-chloro-5- trifluoromethylpyridine and 3-trifluoromethylpyridine reaches 66.6% over the CrO-Al catalyst at a space velocity of 288 h-1 and temperature of 300℃. The reactivity of the deactivated catalysts is recovered after regeneration at 350℃ with mixed gas of nitrogen and air at volume ratio of 1:1. The total yield is around 66% with regenerated catalysts under the condition of 288 h-1 and 300℃. According to the reaction result

the mechanism of one-step chlorofluorination reaction is proposed

dehydrochlorination-condensation of intermediate products accounted for coking. The results of BET

TG and NH3-TPD characterizations indicate that the deactivation of the catalysts is caused by the carbonaceous by-products which cover the surface and pores of the catalyst.

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