Novel strategies for terephthalic acid processing under soft conditions using ionic liquids
Terephthalic acid (H2TPA) solubility in several ionic liquids (ILs) at multiple concentrations is higher than for any other known solvents at lower temperatures and pressures which suggests low energy purification of H2TPA from its major impurity, 4-carboxybenzaldehyde (4-CBA) might be possible. To...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-06-01
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| Series: | Journal of Ionic Liquids |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772422024000028 |
| _version_ | 1797295720867299328 |
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| author | Geetha Bolla Amrita Nayak Gregory Chatel Varun Debbeti C. Corey Hines Steven P. Kelley Thomas P. Vaid Allan S. Myerson Robin D. Rogers |
| author_facet | Geetha Bolla Amrita Nayak Gregory Chatel Varun Debbeti C. Corey Hines Steven P. Kelley Thomas P. Vaid Allan S. Myerson Robin D. Rogers |
| author_sort | Geetha Bolla |
| collection | DOAJ |
| description | Terephthalic acid (H2TPA) solubility in several ionic liquids (ILs) at multiple concentrations is higher than for any other known solvents at lower temperatures and pressures which suggests low energy purification of H2TPA from its major impurity, 4-carboxybenzaldehyde (4-CBA) might be possible. To understand the mechanism several strategies were explored to purify H2TPA by taking advantage of this high solubilizing power of ILs for H2TPA in the crystallization of unique salts and cocrystals. Using either zwitterionic carboxylate IL-precursors or direct salt formation with carboxylate ILs or amines, a series of salts of mono, dibasic and two ionic cocrystals were obtained including monobasic, [C1C1im][HTPA], [N4441][HTPA], [C4C1im][HTPA]•0.5H2TPA (a cocrystal), and [C1Him][HTPA] ([C1C1im]+ = 1,3-dimethylimidazolium, [N4441]+ = tribuytlmethylammonium, [C1Him]+ = 1-methyl-3-H-imidazolium), dibasic [C1C1im]2[TPA], [C4C1im]2[TPA], [N4444]2[TPA], [C1Him]2[TPA], [H2N22]2[TPA], [H3N6]2[TPA], and [HN(CH2CH2OH)3]2[TPA] ([C4C1im]+ = 1-butyl-3-methylimidazolium, [N4444]+ = tetrabuylammonium, [H3N6]+ = hexylammonium, [HN(CH2CH2OH)3]+ = triethanolammonium, [H2N22]+= diethylammonium), and a second cocrystal [C2C1im]Cl•0.5H2TPA. The formation of these salts suggest a viable method to purify H2TPA because of preferred salt formation at low energy conditions. One elegant route using 1-ethyl-3-methylimidazolium chloride ([C2C1im]Cl) could be especially promising because the cocrystal [C2C1im]Cl•0.5H2TPA was readily isolated and is easily dissociated when exposed to ambient conditions into crystalline H2TPA and a liquid of hydrated [C2C1im]Cl. |
| first_indexed | 2024-03-07T21:52:05Z |
| format | Article |
| id | doaj.art-1f6dbabc7f134ba29f6740b5aec8d785 |
| institution | Directory Open Access Journal |
| issn | 2772-4220 |
| language | English |
| last_indexed | 2024-03-07T21:52:05Z |
| publishDate | 2024-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Ionic Liquids |
| spelling | doaj.art-1f6dbabc7f134ba29f6740b5aec8d7852024-02-25T04:36:39ZengElsevierJournal of Ionic Liquids2772-42202024-06-0141100079Novel strategies for terephthalic acid processing under soft conditions using ionic liquidsGeetha Bolla0Amrita Nayak1Gregory Chatel2Varun Debbeti3C. Corey Hines4Steven P. Kelley5Thomas P. Vaid6Allan S. Myerson7Robin D. Rogers8Department of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USADepartment of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, MA 02139, USADepartment of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL 35487, USA; Corresponding author.Terephthalic acid (H2TPA) solubility in several ionic liquids (ILs) at multiple concentrations is higher than for any other known solvents at lower temperatures and pressures which suggests low energy purification of H2TPA from its major impurity, 4-carboxybenzaldehyde (4-CBA) might be possible. To understand the mechanism several strategies were explored to purify H2TPA by taking advantage of this high solubilizing power of ILs for H2TPA in the crystallization of unique salts and cocrystals. Using either zwitterionic carboxylate IL-precursors or direct salt formation with carboxylate ILs or amines, a series of salts of mono, dibasic and two ionic cocrystals were obtained including monobasic, [C1C1im][HTPA], [N4441][HTPA], [C4C1im][HTPA]•0.5H2TPA (a cocrystal), and [C1Him][HTPA] ([C1C1im]+ = 1,3-dimethylimidazolium, [N4441]+ = tribuytlmethylammonium, [C1Him]+ = 1-methyl-3-H-imidazolium), dibasic [C1C1im]2[TPA], [C4C1im]2[TPA], [N4444]2[TPA], [C1Him]2[TPA], [H2N22]2[TPA], [H3N6]2[TPA], and [HN(CH2CH2OH)3]2[TPA] ([C4C1im]+ = 1-butyl-3-methylimidazolium, [N4444]+ = tetrabuylammonium, [H3N6]+ = hexylammonium, [HN(CH2CH2OH)3]+ = triethanolammonium, [H2N22]+= diethylammonium), and a second cocrystal [C2C1im]Cl•0.5H2TPA. The formation of these salts suggest a viable method to purify H2TPA because of preferred salt formation at low energy conditions. One elegant route using 1-ethyl-3-methylimidazolium chloride ([C2C1im]Cl) could be especially promising because the cocrystal [C2C1im]Cl•0.5H2TPA was readily isolated and is easily dissociated when exposed to ambient conditions into crystalline H2TPA and a liquid of hydrated [C2C1im]Cl.http://www.sciencedirect.com/science/article/pii/S2772422024000028Terephthalic acidPurificationIonic liquidsSolubilityIonic cocrystalsCrystallization |
| spellingShingle | Geetha Bolla Amrita Nayak Gregory Chatel Varun Debbeti C. Corey Hines Steven P. Kelley Thomas P. Vaid Allan S. Myerson Robin D. Rogers Novel strategies for terephthalic acid processing under soft conditions using ionic liquids Journal of Ionic Liquids Terephthalic acid Purification Ionic liquids Solubility Ionic cocrystals Crystallization |
| title | Novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| title_full | Novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| title_fullStr | Novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| title_full_unstemmed | Novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| title_short | Novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| title_sort | novel strategies for terephthalic acid processing under soft conditions using ionic liquids |
| topic | Terephthalic acid Purification Ionic liquids Solubility Ionic cocrystals Crystallization |
| url | http://www.sciencedirect.com/science/article/pii/S2772422024000028 |
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