Safe and on-demand protocol for the continuous generation of SO2 and Cl2 for subsequent utilization in organic synthesis

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Flow Chemistry Pub Date : 2023-07-24 DOI:10.1007/s41981-023-00280-2
Gulice Yiu Chung Leung, Shannon Thoi Rui Ying, Edwin Chia, Anqi Chen, Gabriel Loh, Balamurugan Ramalingam
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Abstract

Hazardous reagents such as sulfur dioxide (SO2) and chlorine (Cl2) are powerful and atom-efficient reagents for respectively introducing the ‘SO2’ moiety and ‘Cl’ atom into organic molecules. However, their use is limited due to a lack of protocols and methods to access them in laboratories readily. This article describes the development of a prototype, method, and process for accessing hazardous gaseous reagents safely on demand continuously for further utilization in organic synthesis. The prototype was validated by producing SO2 from readily accessible laboratory reagents sodium sulfite (Na2SO3) and sulfuric acid (H2SO4). The generated SO2 was successfully utilized for the synthesis of aryl sulfinate salts, which were subsequently converted to sulfonamides and sulfone-containing bicalutamide drugs. The broader applicability of the reactor prototype has also been demonstrated in the generation of chlorine gas from bleach (NaOCl) and hydrochloric acid (HCl), followed by the separation of chlorine gas from an acidic aqueous reaction mixture. The utilization of the separated chlorine gas was demonstrated in the synthesis of silyl chlorides in both batch and continuous manners. The present reactor prototype not only enables safe and convenient access to highly hazardous gaseous reagents for facile organic synthesis in laboratories, but also eliminates the risks in handling, storage, and transportation of hazardous gaseous reagents in cylinders.

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安全的和按需的方案连续生成SO2和Cl2用于随后的有机合成利用
二氧化硫(SO2)和氯气(Cl2)等危险试剂是分别将 "SO2 "分子和 "Cl "原子引入有机分子的强效原子高效试剂。然而,由于缺乏在实验室中随时使用它们的规程和方法,它们的使用受到了限制。本文介绍了一种原型、方法和流程的开发,该原型、方法和流程可按需安全地持续获取危险气态试剂,以便在有机合成中进一步利用。该原型通过利用实验室现成试剂亚硫酸钠 (Na2SO3) 和硫酸 (H2SO4) 生产二氧化硫进行了验证。生成的二氧化硫被成功用于合成芳基硫酸酯盐,随后转化为磺胺类药物和含砜的比卡鲁胺药物。该反应器原型的广泛适用性还体现在从漂白剂(NaOCl)和盐酸(HCl)中生成氯气,然后从酸性水反应混合物中分离出氯气。分离出的氯气在间歇式和连续式合成硅基氯化物的过程中都得到了验证。本反应器原型不仅可以安全方便地获取高危气态试剂,在实验室中进行简单的有机合成,而且消除了处理、储存和运输装在气瓶中的危险气态试剂的风险。
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来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
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