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Preparation of Mono- and Diisocyanates in Flow from Renewable Carboxylic Acids
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-05-29 , DOI: 10.1021/acs.oprd.0c00167
Thien An Phung Hai 1 , Laurent J. S. De Backer 2 , Nicholas D. P. Cosford 2 , Michael D. Burkart 1, 3
Affiliation  

Diisocyanates used in polyurethanes are commonly prepared by phosgenation of petroleum-sourced diamines. This involves highly toxic phosgene and produces corrosive HCl, limiting synthetic applications. In our search for a renewable source for diisocyanates, we have developed a practical methodology for the production of isocyanates from algae-biomass-derived fatty acids or other renewable sources. This technique utilizes flow chemistry to prepare and convert high-energy intermediates, thus mitigating safety concerns. By the use of continuous flow, acyl azides are prepared from hydrazides and subsequently heated to undergo Curtius rearrangement, affording isocyanates in one scalable process. The method is efficient, safe, and sustainable, offers an opportunity to prepare isocyanates and diisocyanates from renewable feedstocks, and is amenable to distributed manufacturing processes.

中文翻译:

由可再生羧酸制备流动性的单异氰酸酯和二异氰酸酯

聚氨酯中使用的二异氰酸酯通常是通过石油来源的二胺的光气化制备的。这涉及剧毒的光气并产生腐蚀性的HCl,限制了合成应用。在寻找二异氰酸酯的可再生资源时,我们已经开发了一种实用的方法,用于从藻类生物质衍生的脂肪酸或其他可再生资源生产异氰酸酯。该技术利用流动化学来制备和转化高能中间体,从而减轻了安全隐患。通过使用连续流动,由酰肼制备酰基叠氮化物,然后将其加热以进行库尔休斯重排,以一种可扩展的方法提供异氰酸酯。该方法高效,安全且可持续,为从可再生原料制备异氰酸酯和二异氰酸酯提供了机会,
更新日期:2020-05-29
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