Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose
Deep eutectic solvents (DESs) offer attractive options for the “green” dissolution of cellulose. However, the protic hydroxyl group causes weak dissolving ability of DESs, requiring the substitution of hydroxyl groups in the cation. In this study, a novel allyl-functionalized DES was synthesized and...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
North Carolina State University
2016-08-01
|
| Series: | BioResources |
| Subjects: | |
| Online Access: | http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_4_8457_Ren_Synthesis_Novel_Eutectic_Solvent |
| _version_ | 1828723008363036672 |
|---|---|
| author | Hongwei Ren Chunmao Chen Shaohui Guo Dishun Zhao Qinghong Wang |
| author_facet | Hongwei Ren Chunmao Chen Shaohui Guo Dishun Zhao Qinghong Wang |
| author_sort | Hongwei Ren |
| collection | DOAJ |
| description | Deep eutectic solvents (DESs) offer attractive options for the “green” dissolution of cellulose. However, the protic hydroxyl group causes weak dissolving ability of DESs, requiring the substitution of hydroxyl groups in the cation. In this study, a novel allyl-functionalized DES was synthesized and characterized, and its possible effect on improved dissolution of cellulose was investigated. The DES was synthesized by a eutectic mixture of allyl triethyl ammonium chloride ([ATEAm]Cl) and oxalic acid (Oxa) at a molar ratio of 1:1 and a freezing point of 49 °C. The [ATEAm]Cl-Oxa exhibited high polarity (56.40 kcal/mol), dipolarity/polarizability effects (1.10), hydrogen-bond donating acidity (0.41), hydrogen-bond basicity (0.89), and low viscosity (76 cP at 120 °C) owing to the π-π conjugative effect induced by the allyl group. The correlation between temperature and viscosity on the [ATEAm]Cl-Oxa fit the Arrhenius equation well. The [ATEAm]Cl-Oxa showed low pseudo activation energy for viscous flow (44.56 kJ/mol). The improved properties of the [ATEAm]Cl-Oxa noticeably promoted the solubility (6.48 wt.%) of cellulose. |
| first_indexed | 2024-04-12T12:42:18Z |
| format | Article |
| id | doaj.art-00923810e36f4111958f89e9ef5892f9 |
| institution | Directory Open Access Journal |
| issn | 1930-2126 1930-2126 |
| language | English |
| last_indexed | 2024-04-12T12:42:18Z |
| publishDate | 2016-08-01 |
| publisher | North Carolina State University |
| record_format | Article |
| series | BioResources |
| spelling | doaj.art-00923810e36f4111958f89e9ef5892f92022-12-22T03:32:43ZengNorth Carolina State UniversityBioResources1930-21261930-21262016-08-011148457846910.15376/biores.11.4.8457-8469Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of CelluloseHongwei Ren0Chunmao Chen1Shaohui Guo2Dishun Zhao3Qinghong Wang4China University of Petroleum, Beijing; ChinaChina University of Petroleum, Beijing; ChinaChina University of Petroleum, Beijing; ChinaHebei University of Science and Technology; ChinaChina University of Petroleum, Beijing; ChinaDeep eutectic solvents (DESs) offer attractive options for the “green” dissolution of cellulose. However, the protic hydroxyl group causes weak dissolving ability of DESs, requiring the substitution of hydroxyl groups in the cation. In this study, a novel allyl-functionalized DES was synthesized and characterized, and its possible effect on improved dissolution of cellulose was investigated. The DES was synthesized by a eutectic mixture of allyl triethyl ammonium chloride ([ATEAm]Cl) and oxalic acid (Oxa) at a molar ratio of 1:1 and a freezing point of 49 °C. The [ATEAm]Cl-Oxa exhibited high polarity (56.40 kcal/mol), dipolarity/polarizability effects (1.10), hydrogen-bond donating acidity (0.41), hydrogen-bond basicity (0.89), and low viscosity (76 cP at 120 °C) owing to the π-π conjugative effect induced by the allyl group. The correlation between temperature and viscosity on the [ATEAm]Cl-Oxa fit the Arrhenius equation well. The [ATEAm]Cl-Oxa showed low pseudo activation energy for viscous flow (44.56 kJ/mol). The improved properties of the [ATEAm]Cl-Oxa noticeably promoted the solubility (6.48 wt.%) of cellulose.http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_4_8457_Ren_Synthesis_Novel_Eutectic_SolventCelluloseDissolutionDeep eutectic solventAllyl triethyl ammonium chloride |
| spellingShingle | Hongwei Ren Chunmao Chen Shaohui Guo Dishun Zhao Qinghong Wang Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose BioResources Cellulose Dissolution Deep eutectic solvent Allyl triethyl ammonium chloride |
| title | Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose |
| title_full | Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose |
| title_fullStr | Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose |
| title_full_unstemmed | Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose |
| title_short | Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose |
| title_sort | synthesis of a novel allyl functionalized deep eutectic solvent to promote dissolution of cellulose |
| topic | Cellulose Dissolution Deep eutectic solvent Allyl triethyl ammonium chloride |
| url | http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_4_8457_Ren_Synthesis_Novel_Eutectic_Solvent |
| work_keys_str_mv | AT hongweiren synthesisofanovelallylfunctionalizeddeepeutecticsolventtopromotedissolutionofcellulose AT chunmaochen synthesisofanovelallylfunctionalizeddeepeutecticsolventtopromotedissolutionofcellulose AT shaohuiguo synthesisofanovelallylfunctionalizeddeepeutecticsolventtopromotedissolutionofcellulose AT dishunzhao synthesisofanovelallylfunctionalizeddeepeutecticsolventtopromotedissolutionofcellulose AT qinghongwang synthesisofanovelallylfunctionalizeddeepeutecticsolventtopromotedissolutionofcellulose |