通过顺序乙酰化和Mn/ br催化自氧化将聚苯乙烯转化为对苯二甲酸

IF 13.1 1区 化学 Q1 CHEMISTRY, PHYSICAL
Doohyun Baek, Dylan J. Walsh, James B. Gerken, Madelyn G. Frank, Ive Hermans and Shannon S. Stahl*, 
{"title":"通过顺序乙酰化和Mn/ br催化自氧化将聚苯乙烯转化为对苯二甲酸","authors":"Doohyun Baek,&nbsp;Dylan J. Walsh,&nbsp;James B. Gerken,&nbsp;Madelyn G. Frank,&nbsp;Ive Hermans and Shannon S. Stahl*,&nbsp;","doi":"10.1021/acscatal.5c04744","DOIUrl":null,"url":null,"abstract":"<p >Most methods for the oxidative deconstruction of polystyrene produce benzoic acid, which has a low market size relative to the production of waste polystyrene. The present study demonstrates a method for conversion of polystyrene into terephthalic acid, a high-volume chemical, by introducing a carbon-containing fragment into the <i>para</i> position of the phenyl groups in polystyrene, followed by Mn/Br-catalyzed autoxidation. Acetylated polystyrene is shown to be the most effective substrate for oxidation, affording an 81% yield of terephthalic acid. Mechanistic studies highlight the effectiveness of bromide as a cocatalyst and offer insight into the underlying reasons the acetyl group undergoes efficient oxidation.</p>","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"15 18","pages":"16421–16426"},"PeriodicalIF":13.1000,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Conversion of Polystyrene to Terephthalic Acid via Sequential Acetylation and Mn/Br-Catalyzed Autoxidation\",\"authors\":\"Doohyun Baek,&nbsp;Dylan J. Walsh,&nbsp;James B. Gerken,&nbsp;Madelyn G. Frank,&nbsp;Ive Hermans and Shannon S. Stahl*,&nbsp;\",\"doi\":\"10.1021/acscatal.5c04744\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Most methods for the oxidative deconstruction of polystyrene produce benzoic acid, which has a low market size relative to the production of waste polystyrene. The present study demonstrates a method for conversion of polystyrene into terephthalic acid, a high-volume chemical, by introducing a carbon-containing fragment into the <i>para</i> position of the phenyl groups in polystyrene, followed by Mn/Br-catalyzed autoxidation. Acetylated polystyrene is shown to be the most effective substrate for oxidation, affording an 81% yield of terephthalic acid. Mechanistic studies highlight the effectiveness of bromide as a cocatalyst and offer insight into the underlying reasons the acetyl group undergoes efficient oxidation.</p>\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":\"15 18\",\"pages\":\"16421–16426\"},\"PeriodicalIF\":13.1000,\"publicationDate\":\"2025-09-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acscatal.5c04744\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acscatal.5c04744","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

摘要

聚苯乙烯的氧化分解方法大多产生苯甲酸,相对于废聚苯乙烯的生产,苯甲酸的市场规模较小。本研究展示了一种将聚苯乙烯转化为对苯二甲酸的方法,该方法通过将含碳片段引入聚苯乙烯中苯基的对位,然后进行Mn/ br催化自氧化。乙酰化聚苯乙烯被证明是最有效的氧化底物,可提供81%的对苯二甲酸收率。机理研究强调了溴作为助催化剂的有效性,并提供了对乙酰基进行有效氧化的根本原因的见解。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Conversion of Polystyrene to Terephthalic Acid via Sequential Acetylation and Mn/Br-Catalyzed Autoxidation

Conversion of Polystyrene to Terephthalic Acid via Sequential Acetylation and Mn/Br-Catalyzed Autoxidation

Conversion of Polystyrene to Terephthalic Acid via Sequential Acetylation and Mn/Br-Catalyzed Autoxidation

Most methods for the oxidative deconstruction of polystyrene produce benzoic acid, which has a low market size relative to the production of waste polystyrene. The present study demonstrates a method for conversion of polystyrene into terephthalic acid, a high-volume chemical, by introducing a carbon-containing fragment into the para position of the phenyl groups in polystyrene, followed by Mn/Br-catalyzed autoxidation. Acetylated polystyrene is shown to be the most effective substrate for oxidation, affording an 81% yield of terephthalic acid. Mechanistic studies highlight the effectiveness of bromide as a cocatalyst and offer insight into the underlying reasons the acetyl group undergoes efficient oxidation.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
ACS Catalysis
ACS Catalysis CHEMISTRY, PHYSICAL-
CiteScore
20.80
自引率
6.20%
发文量
1253
审稿时长
1.5 months
期刊介绍: ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信