Water-Doped Brønsted Acidic Protic Ionic Liquids for Enhanced Tributyl Citrate Synthesis in a Two-Phase Esterification System.
Brønsted acidic ionic liquids
esterification
plasticizers
protic ionic liquids
tributyl citrate
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
03 Mar 2024
03 Mar 2024
Historique:
revised:
24
02
2024
received:
03
01
2024
pubmed:
4
3
2024
medline:
4
3
2024
entrez:
3
3
2024
Statut:
aheadofprint
Résumé
Tributyl citrate (TBC) plays a crucial role as a plasticizer, enhancing the flexibility of polymers such as polyvinyl chloride. Its biodegradability and non-toxic nature contribute to eco-friendly appeal, making it a preferred additive in diverse industries, including food packaging, medical devices, toys, and consumer goods. Herein, a method for the synthesis of TBC using inexpensive Brønsted acidic protic ionic liquids (ILs) in a two-phase reaction system is presented. The esterification process is carried out with high yield (>99 %), selectivity (up to 98 %) and short reaction time of 2 h. The catalyst in the form of IL shows excellent performance and stability, desirable for industrial applications.
Identifiants
pubmed: 38433098
doi: 10.1002/asia.202400006
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202400006Subventions
Organisme : Silesian University of Technology
ID : 04/050/BKM23/0176
Organisme : Silesian University of Technology
ID : LIDER/24/0100//L-9/17/NCBR/2018
Organisme : National Centre for Research and Development, Poland
Informations de copyright
© 2024 Wiley-VCH GmbH.
Références
J. P. Harmon, R. Otter, ACS Sustainable Chem. Eng. 2018, 6, 2078-2085.
F. Chiellini, M. Ferri, A. Morelli, L. Dipaola, G. Latini, Prog. Polym. Sci. 2013, 38, 1067-1088.
http://ec.europa.eu/transparency/regdoc/rep/3/2015/PL/3-2015-2067-PL-F1-1.PDF, Date Accessed: 23.02.2019, n.d.
J. M. Ferri, V. Fombuena Borràs, M. Fernando, A. Carrasco, I. N. Vikhareva, G. K. Aminova, A. K. Mazitova, Polym. 2022, 14, 1888.
I. N. Vikhareva, G. K. Aminova, A. K. Mazitova, Molecules 2021, 26, Doi: 10.3390/MOLECULES26164833.
L. A. Dupont, V. P. Gupta, J. Vinyl Technol. 1993, 15, 100-104.
L. Dahbi, A. Farce, N. Kambia, I. Séverin, T. Dine, E. Moreau, V. Sautou, M. C. Chagnon, Arch. Toxicol. 2022, 96, 899-918.
W. D. Arendt, J. Lang, J. Vinyl Addit. Technol. 1998, 4, 184-188.
I. O. Maydanova, S. N. Lakeev, O. V. Ishalina, A. P. Nikitina, Russ. J. Appl. Chem. 2020, 93, 1883-1887.
S. S. Jagarlapudi, H. S. Cross, T. Das, W. A. Goddard, ACS Appl. Mater. Interfaces 2023, 15, 24858-24867.
V. Najafi, H. Abdollahi, Eur. Polym. J. 2020, 128, 109620.
B. M. Elsiwi, O. Garcia-Valdez, H. C. Erythropel, R. L. Leask, J. A. Nicell, M. Maric, ACS Sustainable Chem. Eng. 2020, 8, 12409-12418.
G. Godbille-Cardona, J. A. Nicell, M. Marić, R. L. Leask, J. Vinyl Addit. Technol. 2023, 29, 283-293.
I. P. Gross, R. H. Saatkamp, M. P. Sanches, A. L. Parize, A. T. N. Pires, ACS Appl. Polym. Mater. 2022, Doi: 10.1021/ACSAPM.2C01273/SUPPL_FILE/AP2C01273_SI_001.PDF.
D. L. Cai, X. Yue, B. Hao, P. C. Ma, J. Cleaner Prod. 2020, 274, 122781.
F. Song, C. Huang, X. Zhu, C. Liu, Y. Zhou, P. Jia, J. Appl. Polym. Sci. 2021, 138, 50809.
S. Feng, P. Zhang, P. Jiang, Z. Zhang, J. Deng, Z. Cao, Eur. Polym. J. 2022, 169, 111125.
W. Gao, P. Jiang, Q. Gu, H. Zhang, P. Zhang, A. Haryono, New J. Chem. 2021, 45, 123-130.
A. Alhanish, M. Abu Ghalia, Biotechnol. Prog. 2021, 37, e3210.
https://ihsmarkit.com/products/plasticizers-chemical-economics-handbook.html, “https://ihsmarkit.com/products/plasticizers-chemical-economics-handbook.html, date accessed: 23.02.2019.,” n.d.
G. Bleys, “Technology Watch Plast. essenscia 2015, http://PUR.
M. G. A. Vieira, M. A. Da Silva, L. O. Dos Santos, M. M. Beppu, Eur. Polym. J. 2011, 47, 254-263.
M. Berovic, M. Legisa, Biotechnol. Annu. Rev. 2007, 13, 303-343.
S. Anastassiadis, I. G. Morgunov, S. V. Kamzolova, T. V. Finogenova, Recent Pat. Biotechnol. 2008, 2, 107-123.
A. R. Angumeenal, D. Venkappayya, LWT-Food Sci. Technol. 2013, 50, 367-370.
Z. Yang, Z. Bai, H. Sun, Z. Yu, X. Li, Y. Guo, H. Zhang, Microb. Cell Fact. 2014, 13, Doi: 10.1186/s12934-014-0182-4.
P. L. Show, K. O. Oladele, Q. Y. Siew, F. A. Aziz Zakry, J. C.-W. Lan, T. C. Ling, Front. Life Sci. 2015, 8, 271-283.
H. M. Park, M. Misra, L. T. Drzal, A. K. Mohanty, Biomacromolecules 2004, 5, 2281-2288.
L. V. Labrecque, R. A. Kumar, V. Davé, R. A. Gross, S. P. McCarthy, J. Appl. Polym. Sci. 1997, 66, 1507-1513.
K. Y. Nandiwale, P. Gogoi, V. V. Bokade, Chem. Eng. Res. Des. 2015, 98, 212-219.
J. Han, M. Zhang, H. Zhang, H. Liu, S. Xu, J. Vinyl Addit. Technol. 2022, 28, 751-761.
P. Jia, H. Xia, K. Tang, Y. Zhou, Polym. 2018, 10, 1303.
R. Quintana, O. Persenaire, Y. Lemmouchi, J. Sampson, S. Martin, L. Bonnaud, P. Dubois, Polym. Degrad. Stab. 2013, 98, 1556-1562.
S. Jiang, R. Guan, H. Chen, J. Zhao, S. Zha, Z. Ke, J. Wuhan Univ. Technol. Mater. Sci. Ed. 2014, 29, 553-560.
Y. Lemmouchi, M. Murariu, A. M. Dos Santos, A. J. Amass, E. Schacht, P. Dubois, Eur. Polym. J. 2009, 45, 2839-2848.
A. Chaos, A. Sangroniz, A. Gonzalez, M. Iriarte, J. R. Sarasua, J. del Río, A. Etxeberria, Polym. Int. 2019, 68, 125-133.
N. Ljungberg, B. Wesslén, Polymer 2003, 44, 7679-7688.
T. Mekonnen, P. Mussone, H. Khalil, D. Bressler, J. Mater. Chem. A 2013, 1, 13379-13398.
M. M. Fiume, B. A. Heldreth, W. F. Bergfeld, D. V. Belsito, R. A. Hill, C. D. Klaassen, D. C. Liebler, J. G. Marks, R. C. Shank, T. J. Slaga, P. W. Snyder, F. A. Andersen, n.d., Doi: 10.1177/1091581814526891.
L. Wang, B. Ding, M. Zhang, RSC Adv. 2019, 9, 33124-33129.
K. Shi, H. Yu, S. Lakshmana Rao, T. C. Lee, J. Agric. Food Chem. 2012, 60, 5988-5993.
Z. Yang, H. Bi, Y. Bi, D. Rodrigue, M. Xu, X. Feng, Polym. Compos. 2019, 40, 1384-1394.
S. Wang, L. Xu, L. Xu, C. Tian, Y. Guan, Int. J. Polym. Sci. 2018, 2018, Doi: 10.1155/2018/1953563.
Z. Yang, M. Peng, Y. Li, X. Wu, T. Gui, Y. Li, F. Zhang, X. Chen, H. Kita, Membranes (Basel). 2022, 12, Doi: 10.3390/MEMBRANES12121269.
O. M. Osorio-Pascuas, M. A. Santaella, G. Rodriguez, A. Orjuela, Ind. Eng. Chem. Res. 2015, 54, 12534-12542.
M. A. Santaella, M. F. Gutiérrez, A. Orjuela, Chem. Eng. J. 2022, 433, 133199.
W. F. Bohorquez, O. M. Osorio-Pascuas, M. A. Santaella, A. Orjuela, Ind. Eng. Chem. Res. 2020, 59, 19203-19211.
H. Yang, H. Song, H. Zhang, P. Chen, Z. Zhao, J. Mol. Catal. A 2014, 381, 54-60.
L. Wang, B. Ding, M. Zhang, RSC Adv. 2019, 9, 33124-33129.
Z. Zhifeng, X. Junming, J. Jianchun, L. Yanju, H. Yuanbo, Bull. Chem. Soc. Ethiop. 2011, 25, 147-150.
Y. Lu, S. Xu, F. Zhao, AIP Conf. Proc. 2017, 1794, 50007.
M. A. Santaella, A. Orjuela, A. Suaza, J. L. Rivera, A. F. Martínez, G. Rodríguez, Ind. Eng. Chem. Res. 2020, 59, 10583-10594.
J. D. Fonseca, A. M. Latifi, A. Orjuela, G. Rodríguez, I. D. Gil, Comput. Chem. Eng. 2020, 132, 106603.
N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150.
C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 2005, 18, 275-297.
M. B. Shiflett, Ed., Commercial Applications of Ionic Liquids, Springer International Publishing, Cham, 2020.
J. Pernak, D. K. Kaczmarek, T. Rzemieniecki, M. Niemczak, Ł. Chrzanowski, T. Praczyk, J. Agric. Food Chem. 2020, 68, 4588-4594.
K. Matuszek, A. Chrobok, F. Coleman, K. R. Seddon, M. Swadźba-Kwaśny, Green Chem. 2014, 16, 3463.
A. Brzéczek-Szafran, K. Erfurt, M. Swadźba-Kwaśny, T. Piotrowski, A. Chrobok, ACS Sustainable Chem. Eng. 2022, 10, 13568-13575.
N. Barteczko, J. Więcławik, A. Tracz, E. Pankalla, K. Erfurt, P. Latos, S. Boncel, K. Matuszek, A. Chrobok, Materials (Basel). 2021, 14, Doi: 10.3390/MA14206219.
Y. Leng, J. Wang, D. Zhu, X. Ren, H. Ge, L. Shen, Angew. Chem. 2009, 121, 174-177.
A. Brzęczek-Szafran, J. Więcławik, N. Barteczko, A. Szelwicka, E. L. Byrne, A. Kolanowska, M. Swadzba-Kwasny, A. Chrobok, Green Chem. 2021, DOI 10.1039/D1GC00515D.
J. J. Bailey, E. L. Byrne, P. Goodrich, P. Kavanagh, M. Swadzba-Kwasny, Green Chem. 2024, 26, 1092-1131.
J. D. Holbrey, M. Swadźba-Kwaśny, A. Mcgrogan, E. L. Byrne, R. Guiney, T. F. Headen, T. G. A. Youngs, A. Chrobok, Phys. Chem. Chem. Phys. 2023, 25, 9785-9795.
A. Grymel, P. Latos, K. Matuszek, K. Erfurt, N. Barteczko, E. Pankalla, A. Chrobok, Catal 2020, 10, 457.
U. Dorosz, N. Barteczko, P. Latos, K. Erfurt, E. Pankalla, A. Chrobok, Catalysts 2019, 10, 37.
K. Matuszek, A. Brzeczek-Szafran, D. Kobus, D. R. Macfarlane, M. Swadźba-Kwaśny, A. Chrobok, Aust. J. Chem. 2019, 72, 130-138.
X. U. Junming, J. Jianchun, Z. Zhiyue, L. Jing, Process Saf. Environ. Prot. 2010, 88, 28-30.
G. Li, F. Wu, H. Tong, Adv. Mater. Res. 2011, 233-235, 155-159.
J. Xu, J. Jiang, L. V. Wei, Y. Gao, Chem. Eng. Commun. 2010, 198, 474-482.
A. Yuan, H. Liang, Z. Huang, D. Wei, ScienceAsia 2021, 47, 187-194.
H. Li, S. Zhao, W. Zhang, H. Du, X. Yang, Y. Peng, D. Han, B. Wang, Z. Li, Fuel 2023, 342, 127786.