Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base
Muconic acid, a crucial precursor in synthesizing materials like PET bottles and nylon, is pivotal for the anticipated growth in the textiles and plastics industries. This study presents a novel chemical synthesis route for <i>cis</i>,<i>cis</i>-muconic acid (ccMA) using cate...
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| Format: | Article |
| Language: | English |
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/1/201 |
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| author | Kohtaro Katayama Hiroki Hotta Yoshio Tsujino |
| author_facet | Kohtaro Katayama Hiroki Hotta Yoshio Tsujino |
| author_sort | Kohtaro Katayama |
| collection | DOAJ |
| description | Muconic acid, a crucial precursor in synthesizing materials like PET bottles and nylon, is pivotal for the anticipated growth in the textiles and plastics industries. This study presents a novel chemical synthesis route for <i>cis</i>,<i>cis</i>-muconic acid (ccMA) using catechol. Biochemical methods face scale-up challenges due to microorganism sensitivity and complex extraction processes, while chemical methods involve environmentally harmful substances and have low yields. Our research introduces a method that enhances ccMA yield to 56% by employing ozonation in the presence of an alkali, significantly simplifying the synthesis process. This one-step synthesis reduces reagent use and labor, aligns with green chemistry principles, and avoids using toxic chemicals. The methodology, involving the low-temperature ozonation of catechol with base addition, reduces ccMA degradation and improves yield, as confirmed by an HPLC analysis and replicated experiments. This promising approach could lead to sustainable industrial synthesis of muconic acid derivatives. Further investigations will focus on refining this method for larger-scale applications and testing its economic viability, aiming to optimize conditions for maximum efficiency and yield. |
| format | Article |
| id | doaj-art-a669a4ac0dc941339a0072ac621bf3b7 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-a669a4ac0dc941339a0072ac621bf3b72025-01-10T13:19:12ZengMDPI AGMolecules1420-30492025-01-0130120110.3390/molecules30010201Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a BaseKohtaro Katayama0Hiroki Hotta1Yoshio Tsujino2Graduate School of Maritime Sciences, Kobe University, 5-1-1 Fukae-minami, Kobe 658-0022, Hyogo, JapanGraduate School of Maritime Sciences, Kobe University, 5-1-1 Fukae-minami, Kobe 658-0022, Hyogo, JapanGraduate School of Science, Technology and Innovation, Kobe University, 1-1, Rokkodai, Kobe 657-0013, Hyogo, JapanMuconic acid, a crucial precursor in synthesizing materials like PET bottles and nylon, is pivotal for the anticipated growth in the textiles and plastics industries. This study presents a novel chemical synthesis route for <i>cis</i>,<i>cis</i>-muconic acid (ccMA) using catechol. Biochemical methods face scale-up challenges due to microorganism sensitivity and complex extraction processes, while chemical methods involve environmentally harmful substances and have low yields. Our research introduces a method that enhances ccMA yield to 56% by employing ozonation in the presence of an alkali, significantly simplifying the synthesis process. This one-step synthesis reduces reagent use and labor, aligns with green chemistry principles, and avoids using toxic chemicals. The methodology, involving the low-temperature ozonation of catechol with base addition, reduces ccMA degradation and improves yield, as confirmed by an HPLC analysis and replicated experiments. This promising approach could lead to sustainable industrial synthesis of muconic acid derivatives. Further investigations will focus on refining this method for larger-scale applications and testing its economic viability, aiming to optimize conditions for maximum efficiency and yield.https://www.mdpi.com/1420-3049/30/1/201<i>cis</i>,<i>cis</i>-muconic acidozonolysisgreen chemistrycatecholsynthesis efficiency |
| spellingShingle | Kohtaro Katayama Hiroki Hotta Yoshio Tsujino Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base Molecules <i>cis</i>,<i>cis</i>-muconic acid ozonolysis green chemistry catechol synthesis efficiency |
| title | Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base |
| title_full | Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base |
| title_fullStr | Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base |
| title_full_unstemmed | Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base |
| title_short | Efficient Synthesis of <i>cis</i>,<i>cis</i>-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base |
| title_sort | efficient synthesis of i cis i i cis i muconic acid by catechol oxidation of ozone in the presence of a base |
| topic | <i>cis</i>,<i>cis</i>-muconic acid ozonolysis green chemistry catechol synthesis efficiency |
| url | https://www.mdpi.com/1420-3049/30/1/201 |
| work_keys_str_mv | AT kohtarokatayama efficientsynthesisoficisiicisimuconicacidbycatecholoxidationofozoneinthepresenceofabase AT hirokihotta efficientsynthesisoficisiicisimuconicacidbycatecholoxidationofozoneinthepresenceofabase AT yoshiotsujino efficientsynthesisoficisiicisimuconicacidbycatecholoxidationofozoneinthepresenceofabase |