Synthesis of α,β‐ and β‐Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives

Santhanaraj Daniel; Ruiz Maria P.; Komarneni Mallik R.; Pham Tu; Li Gengnan; Resasco Daniel E.; Faria Jimmy

摘要

Abstract > We report a reaction platform for the synthesis of three different high‐value specialty chemical building blocks starting from bio‐ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde‐containing stream active for the production of C <sub>4</sub> aldehydes via base‐catalyzed aldol‐condensation. Then, the resulting C <sub>4</sub> adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (62?% yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 29?% yield of β‐hydroxy acid (3‐hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading to 21?% yield of α,β‐dihydroxy acid (2,3‐dihydroxybutanoic acid). Crotonic acid, 3‐hydroxybutanoic acid, and 2,3‐dihydroxybutanoic acid are archetypal specialty chemicals used in the synthesis of polyvinyl‐co‐unsaturated acids resins, pharmaceutics, and bio‐degradable/ ‐compatible polymers, respectively. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 我们报告了一种从生物乙醇开始合成三种不同的高价特种化学积木的反应平台，这可能对生物寄生虫的实施产生了重要影响。首先，乙醇对乙醛的氧化脱氢产生含醛的物流，用于生产C. <sub> 4 </ sub> 通过碱催化的醛醇缩合醛。然后，得到的c <sub> 4 </ sub> 通过催化有氧氧化（62μm产率）选择性地将加合物选择性地转化为Croton酸。使用螯合酸的序贯环氧化和氢化导致β-羟基酸（3-羟基丁酸）的29倍。通过控制反应介质的pH，可以水解导致α，β-二羟基酸（2,3-二羟基癸酸）的21μm屈服的氧氢部分。 Croton酸，3-羟基丁酸和2,3-二羟基丁酸是用于合成聚乙烯 - 共同不饱和酸树脂，药物和生物可降解/ - 兼容聚合物的镜片特种化学品。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第19期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Santhanaraj Daniel&option=202" target="_blank" rel="nofollow">Santhanaraj Daniel;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ruiz Maria P.&option=202" target="_blank" rel="nofollow">Ruiz Maria P.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Komarneni Mallik R.&option=202" target="_blank" rel="nofollow">Komarneni Mallik R.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pham Tu&option=202" target="_blank" rel="nofollow">Pham Tu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Gengnan&option=202" target="_blank" rel="nofollow">Li Gengnan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Resasco Daniel E.&option=202" target="_blank" rel="nofollow">Resasco Daniel E.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Faria Jimmy&option=202" target="_blank" rel="nofollow">Faria Jimmy;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>School of Chemical Biological and Materials EngineeringUniversity of OklahomaNorman OK 73019 USA;</p> <p>Faculty of Science and TechnologyUniversity of TwenteEnschede 7522 NB The Netherlands;</p> <p>School of Chemical Biological and Materials EngineeringUniversity of OklahomaNorman OK 73019 USA;</p> <p>School of Chemical Biological and Materials EngineeringUniversity of OklahomaNorman OK 73019 USA;</p> <p>School of Chemical Biological and Materials EngineeringUniversity of OklahomaNorman OK 73019 USA;</p> <p>School of Chemical Biological and Materials EngineeringUniversity of OklahomaNorman OK 73019 USA;</p> <p>Faculty of Science and TechnologyUniversity of TwenteEnschede 7522 NB The Netherlands;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=bioethanol&option=203" rel="nofollow">bioethanol;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chemical building blocks&option=203" rel="nofollow">chemical building blocks;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polyhydroxyalkanoates&option=203" rel="nofollow">polyhydroxyalkanoates;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=tandem chemistry&option=203" rel="nofollow">tandem chemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=unsaturated acids&option=203" rel="nofollow">unsaturated acids;</a> </p> <div class="translation"> 机译：生物乙醇;化学积木;聚羟基烷醇;串联化学;不饱和酸; 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href="/academic-conference-cn_meeting-59370_thesis/020222593801.html">羟基肉桂酸衍生物快速修复色氨酸氧化性损伤</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=苗金玲&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 苗金玲</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=聂永&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,聂永</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=孙国新&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,孙国新</a> <span> <a href="/conference-cn-59370/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化学会第七届全国无机化学学术会议 </a> <span> <span> . 2007</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020313241519.html">5.7-二羟基黄烷酮B环不同位羟基取代衍生物的合成及其抗氧化活性研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=胡基志&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 胡基志</a> <span> . 2018</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120107294052.html">在氧化裂解不饱和脂肪酸和衍生物之后ω-官能化酸的选择性提取</a> <b>[P]</b> . <span> 中国专利： CN104797552A </span> <span> . 2015-07-22</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120111407305.html">一种通过胺催化空气氧化绿色合成5-羟基-5-烃基二取代巴比妥酸衍生物的方法</a> <b>[P]</b> . <span> 中国专利： CN108912057A </span> <span> . 2018-11-30</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130486671418.html">Alkylphthalic acids by epoxidation of alkyltetrahydroanthraquinones - and hydrolysis and oxidation of epoxides</a> <b>[P]</b> . <span> 外国专利：  DE2123349A1 </span> <span> . 1971-11-25</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：烷基四氢蒽醌的环氧化作用以及对环氧化物的水解和氧化作用的烷基邻苯二甲酸 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130486805140.html">Alkylphthalic acids by epoxidation of alkyltetrahydroanthraquinones - and hydrolysis and oxidation of epoxides</a> <b>[P]</b> . <span> 外国专利：  DE000002123349A </span> <span> . 1971-11-25</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：烷基四氢蒽醌的环氧化作用以及对环氧化物的水解和氧化作用的烷基邻苯二甲酸 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130474994330.html">PREPARATION OF CARBAMYL DERIVATIVES OF ALPHA-HYDROXY ACIDS AND THEIR HYDROLYSIS TO THE HYDROXY ACIDS</a> <b>[P]</b> . <span> 外国专利：  GB2061269B </span> <span> . 1983-09-28</span> </div> <p class="zwjiyix translation" 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