Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis
As a result of strict regulations of phthalate plasticizers, alternative non-phthalate forms are desired and increasingly used. This work presents a synthetic method for alternative plasticizers (dialkyl succinates and adipates) via esterification of succinic and adipic acid with alcohols: butan-1-o...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-10-01
|
| Series: | Materials |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1996-1944/14/20/6219 |
| _version_ | 1797513995322654720 |
|---|---|
| author | Natalia Barteczko Justyna Więcławik Anna Tracz Ewa Pankalla Karol Erfurt Piotr Latos Sławomir Boncel Karolina Matuszek Anna Chrobok |
| author_facet | Natalia Barteczko Justyna Więcławik Anna Tracz Ewa Pankalla Karol Erfurt Piotr Latos Sławomir Boncel Karolina Matuszek Anna Chrobok |
| author_sort | Natalia Barteczko |
| collection | DOAJ |
| description | As a result of strict regulations of phthalate plasticizers, alternative non-phthalate forms are desired and increasingly used. This work presents a synthetic method for alternative plasticizers (dialkyl succinates and adipates) via esterification of succinic and adipic acid with alcohols: butan-1-ol and 2-ethylhexan-1-ol. Ionic liquids were synthesized by the reaction of triethylamine with over-equimolar (1:2.7) amounts of sulfuric(VI) acid, which were used as an acidic catalyst and solvent. The two-phase liquid–liquid system was formed during the reaction due to immiscibility of the esters with the ionic liquid. This phenomenon is a driving force of this process, shifting the equilibrium toward the product formation. As a result, dialkyl succinates and adipates were obtained in high yields (99%) and selectivities (>99%), under mild reaction conditions at 70–80 °C and using a 4:1 molar ratio of alcohol to acid and 15 mol% of catalyst. The catalyst was recycled 10 times without any loss of activity. This alternative method is highly competitive: it involves a simple procedure for product isolation as well as a high yield and purity of the resulting esters. These advantages make this method sustainable and promising for industrial applications. |
| first_indexed | 2024-03-10T06:25:19Z |
| format | Article |
| id | doaj.art-cf339d868c3e4a228dd07cd3d2800d7d |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T06:25:19Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-cf339d868c3e4a228dd07cd3d2800d7d2023-11-22T19:01:06ZengMDPI AGMaterials1996-19442021-10-011420621910.3390/ma14206219Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient SynthesisNatalia Barteczko0Justyna Więcławik1Anna Tracz2Ewa Pankalla3Karol Erfurt4Piotr Latos5Sławomir Boncel6Karolina Matuszek7Anna Chrobok8Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandGrupa Azoty Zakłady Azotowe Kędzierzyn, S.A., Mostowa 30A, 47-220 Kędzierzyn-Koźle, PolandGrupa Azoty Zakłady Azotowe Kędzierzyn, S.A., Mostowa 30A, 47-220 Kędzierzyn-Koźle, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandSchool of Chemistry, Monash University, Clayton, VIC 3800, AustraliaDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandAs a result of strict regulations of phthalate plasticizers, alternative non-phthalate forms are desired and increasingly used. This work presents a synthetic method for alternative plasticizers (dialkyl succinates and adipates) via esterification of succinic and adipic acid with alcohols: butan-1-ol and 2-ethylhexan-1-ol. Ionic liquids were synthesized by the reaction of triethylamine with over-equimolar (1:2.7) amounts of sulfuric(VI) acid, which were used as an acidic catalyst and solvent. The two-phase liquid–liquid system was formed during the reaction due to immiscibility of the esters with the ionic liquid. This phenomenon is a driving force of this process, shifting the equilibrium toward the product formation. As a result, dialkyl succinates and adipates were obtained in high yields (99%) and selectivities (>99%), under mild reaction conditions at 70–80 °C and using a 4:1 molar ratio of alcohol to acid and 15 mol% of catalyst. The catalyst was recycled 10 times without any loss of activity. This alternative method is highly competitive: it involves a simple procedure for product isolation as well as a high yield and purity of the resulting esters. These advantages make this method sustainable and promising for industrial applications.https://www.mdpi.com/1996-1944/14/20/6219plasticizerssuccinate estersadipates estersionic liquidsacidic catalysisesterification |
| spellingShingle | Natalia Barteczko Justyna Więcławik Anna Tracz Ewa Pankalla Karol Erfurt Piotr Latos Sławomir Boncel Karolina Matuszek Anna Chrobok Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis Materials plasticizers succinate esters adipates esters ionic liquids acidic catalysis esterification |
| title | Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis |
| title_full | Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis |
| title_fullStr | Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis |
| title_full_unstemmed | Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis |
| title_short | Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis |
| title_sort | dialkyl succinates and adipates as alternative plasticizers even more efficient synthesis |
| topic | plasticizers succinate esters adipates esters ionic liquids acidic catalysis esterification |
| url | https://www.mdpi.com/1996-1944/14/20/6219 |
| work_keys_str_mv | AT nataliabarteczko dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT justynawiecławik dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT annatracz dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT ewapankalla dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT karolerfurt dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT piotrlatos dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT sławomirboncel dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT karolinamatuszek dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis AT annachrobok dialkylsuccinatesandadipatesasalternativeplasticizersevenmoreefficientsynthesis |