{"title":"The preparation of titanium adipate and optimization of its catalytic ester exchange reaction for the synthesis of diisooctyl adipate","authors":"Linlin Zhao, Guoliang Shen, Tiejun Xu, Ruiyang Wen and Sijin Jiang","doi":"10.1039/D4RA08443H","DOIUrl":null,"url":null,"abstract":"<p >Chelated titanium adipate with stable properties was prepared <em>via</em> an ester-exchange reaction using low-carbon alkyl titanate, and it was characterized and analyzed using infrared spectroscopy, thermogravimetry, and scanning electron microscopy. Diisooctyl adipate (DOA) was synthesized <em>via</em> an ester-exchange method using the synthesized novel titanium adipate as a catalyst and isooctanol and dimethyl adipate as raw materials, where dimethyl adipate is the methyl esterification product of the by-product (mixed dicarboxylic acid) in industrial adipic acid production. The process is easy to carry out, green and environmentally friendly, and the methanol by-product can be recycled and utilized. With the objective of optimizing the DOA ester exchange rate, the effects of three factors, namely, catalyst dosage, the molar ratio of isooctanol to dimethyl adipate and the reaction temperature at catalyst addition, on the optimization objective were systematically investigated <em>via</em> one-way and response surface tests. Analysis of variance (ANOVA) and parameter optimization were conducted using Design-Expert software to obtain the optimal parameter combinations and verify the accuracy of the experimental results. The results showed that the optimal reaction conditions were as follows: a catalyst dosage of 2.39%, an isooctanol to dimethyl adipate molar ratio of 2.55 : 1, and a reaction temperature of 117 °C at the time of catalyst addition; this resulted in a high ester exchange rate of 94.23%. Due to the high catalytic efficiency, environmental friendliness and energy saving, and recyclable catalyst, this study provides a feasible process for the effective synthesis of DOA using industrial by-products, which is of significance.</p>","PeriodicalId":102,"journal":{"name":"RSC Advances","volume":" 9","pages":" 6952-6961"},"PeriodicalIF":3.9000,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ra/d4ra08443h?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"RSC Advances","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/ra/d4ra08443h","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
使用低碳烷基钛酸酯通过酯交换反应制备了性能稳定的螯合己二酸钛,并使用红外光谱、热重仪和扫描电子显微镜对其进行了表征和分析。以合成的新型己二酸钛为催化剂,以异辛醇和己二酸二甲酯为原料,通过酯交换法合成了己二酸二异辛酯(DOA),其中己二酸二甲酯是工业己二酸生产中副产物(混合二羧酸)的甲酯化产物。该工艺操作简便,绿色环保,副产物甲醇可回收利用。以优化 DOA 酯交换率为目标,通过单因素试验和响应面试验,系统研究了催化剂用量、异辛醇与己二酸二甲酯的摩尔比以及催化剂加入时的反应温度这三个因素对优化目标的影响。利用 Design-Expert 软件进行了方差分析和参数优化,以获得最佳参数组合并验证实验结果的准确性。结果表明,最佳反应条件如下:催化剂用量为 2.39%,异辛醇与己二酸二甲酯摩尔比为 2.55 :1 ,添加催化剂时的反应温度为 117 °C;这使得酯交换率高达 94.23%。由于催化效率高、环保节能、催化剂可回收,该研究为利用工业副产物有效合成 DOA 提供了一种可行的工艺,具有重要意义。
The preparation of titanium adipate and optimization of its catalytic ester exchange reaction for the synthesis of diisooctyl adipate
Chelated titanium adipate with stable properties was prepared via an ester-exchange reaction using low-carbon alkyl titanate, and it was characterized and analyzed using infrared spectroscopy, thermogravimetry, and scanning electron microscopy. Diisooctyl adipate (DOA) was synthesized via an ester-exchange method using the synthesized novel titanium adipate as a catalyst and isooctanol and dimethyl adipate as raw materials, where dimethyl adipate is the methyl esterification product of the by-product (mixed dicarboxylic acid) in industrial adipic acid production. The process is easy to carry out, green and environmentally friendly, and the methanol by-product can be recycled and utilized. With the objective of optimizing the DOA ester exchange rate, the effects of three factors, namely, catalyst dosage, the molar ratio of isooctanol to dimethyl adipate and the reaction temperature at catalyst addition, on the optimization objective were systematically investigated via one-way and response surface tests. Analysis of variance (ANOVA) and parameter optimization were conducted using Design-Expert software to obtain the optimal parameter combinations and verify the accuracy of the experimental results. The results showed that the optimal reaction conditions were as follows: a catalyst dosage of 2.39%, an isooctanol to dimethyl adipate molar ratio of 2.55 : 1, and a reaction temperature of 117 °C at the time of catalyst addition; this resulted in a high ester exchange rate of 94.23%. Due to the high catalytic efficiency, environmental friendliness and energy saving, and recyclable catalyst, this study provides a feasible process for the effective synthesis of DOA using industrial by-products, which is of significance.
期刊介绍:
An international, peer-reviewed journal covering all of the chemical sciences, including multidisciplinary and emerging areas. RSC Advances is a gold open access journal allowing researchers free access to research articles, and offering an affordable open access publishing option for authors around the world.