Association extraction for vitamin E recovery from deodorizer distillate by in situ formation of deep eutectic solvent

AIChE Journal

Volumn 63, Issue 6, 2017, Pages 2212-2220

  Qin, Lei ^a   Li, Jiangsheng ^a   Cheng, Hongye ^a   Chen, Lifang ^a   Qi, Zhiwen ^a   Yuan, Weikang ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

association extraction; deep eutectic solvent; deodorizer distillate; freezing points; vitamin E

Indexed keywords

EUTECTICS; FREEZING; PHASE TRANSITIONS; RECOVERY; SALTS; SOLVENTS; TERNARY SYSTEMS;

AMERICAN INSTITUTE OF CHEMICAL ENGINEERS; DEEP EUTECTIC SOLVENTS; DEODORIZER DISTILLATES; EXTRACTION EFFICIENCIES; FREEZING POINT; QUATERNARY AMMONIUM SALT; REPRESENTATIVE COMPOUND; VITAMIN-E;

EXTRACTION;

EID: 85007452583     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.15606     Document Type: Article

References (48)

1. Karrer P, Demole V. Synthesis and biological titration of vitamin E. Schweiz Med Wochenschr. 1938;33:954.
2. Ge Y, Yan H, Hui B, Ni Y, Wang S, Cai T. Extraction of natural vitamin E from wheat germ by supercritical carbon dioxide. J Agric Food Chem. 2002;50:685–689.
3. Martins PF, Ito VM, Batistella CB, Maciel MRW. Free fatty acid separation from vegetable oil deodorizer distillate using molecular distillation process. Sep Purif Technol. 2006;48:78–84.
4. Liu D, Shi J, Posada LR, Kakuda Y, Xue SJ. Separating tocotrienols from palm oil by molecular distillation. Food Rev Int. 2008;24:376–391.
5. Abdul Hadi N, Ng MH, Choo YM, Hashim MA, Jayakumar NS. Performance of choline-based deep eutectic solvents in the extraction of tocols from crude palm oil. J Am Oil Chem Soc. 2015;92:1709–1716.
6. Ni X, Xing H, Yang Q, Wang J, Su B, Bao Z, Yang Y, Ren Q. Selective liquid–liquid extraction of natural phenolic compounds using amino acid ionic liquids: a case of α-tocopherol and methyl linoleate separation. Ind Eng Chem Res. 2012;51:6480–6488.
7. Fang T, Goto M, Wang X, Ding X, Geng J, Sasaki M, Hirose T. Separation of natural tocopherols from soybean oil byproduct with supercritical carbon dioxide. J Supercrit Fluids 2007;40:50–58.
8. Chu BS, Baharin BS, Che Man YB, Quek SY. Separation of vitamin E from palm fatty acid distillate using silica: I equilibrium of batch adsorption. J Food Eng. 2004;62:97–103.
9. Top AGM, Leong LW, Ong AS, Kawada T, Watanabe H, Tsuchiya N. Production of high concentration tocopherols and tocotrienols from palm-oil by-products. U.S. Patent 5,190,618, 1993.
10. Torres CF, Torrelo G, Señorans FJ, Reglero G. A two steps enzymatic procedure to obtain sterol esters, tocopherols and fatty acid ethyl esters from soybean oil deodorizer distillate. Process Biochem. 2007;42:1335–1341.
11. Vicente G, Paiva A, Fornari T, Najdanovic-Visak V. Liquid–liquid equilibria for separation of tocopherol from olive oil using ethyl lactate. Chem Eng J. 2011;172:879–884.
12. Dos Santos Freitas L, Jacques RA, Richter MF, Silva AL, Caramão EB. Pressurized liquid extraction of vitamin E from Brazilian grape seed oil. J Chromatogr A 2008;1200:80–83.
13. Qin L, Zhang J, Cheng H, Chen L, Qi Z, Yuan W. Selection of imidazolium-based ionic liquids for vitamin E extraction from deodorizer distillate. ACS Sustain Chem Eng. 2016;4:583–590.
14. Han J, Lei Z, Dong Y, Dai C, Chen B. Process intensification on the separation of benzene and thiophene by extractive distillation. AIChE J. 2015;61:4470–4480.
15. Lyu Z, Zhou T, Chen L, Ye Y, Sundmacher K, Qi Z. Reprint of: Simulation based ionic liquid screening for benzene–cyclohexane extractive separation. Chem Eng Sci. 2014;115:186–194.
16. Cadena C, Anthony JL, Shah JK, Morrow TI, Brennecke JF, Maginn EJ. Why is CO2 so soluble in imidazolium-based ionic liquids? J Am Chem Soc. 2004;126:5300–5308.
17. Chau J, Obuskovic G, Jie X, Mulukutla T, Sirkar KK. Solubilities of CO2 and helium in an ionic liquid containing poly(amidoamine) dendrimer Gen 0. Ind Eng Chem Res. 2013;52:10484–10494.
18. Raeissi S, Florusse LJ, Peters CJ. Purification of flue gas by ionic liquids: carbon monoxide capture in [bmim][Tf2N]. AIChE J. 2013;59:3886–3891.
19. Song Z, Zhou T, Zhang J, Cheng H, Chen L, Qi Z. Screening of ionic liquids for solvent-sensitive extraction -with deep desulfurization as an example. Chem Eng Sci. 2015;129:69–77.
20. Yang Q, Xing H, Su B, Bao Z, Wang J, Yang Y, Ren Q. The essential role of hydrogen-bonding interaction in the extractive separation of phenolic compounds by ionic liquid. AIChE J. 2013;59:1657–1667.
21. Li M, Pham PJ, Pittman, CU, Jr., Li T. Selective solid-phase extraction of α-tocopherol by functionalized ionic liquid-modified mesoporous SBA-15 adsorbent. Anal Sci. 2008;24:1245–1250.
22. Brennecke JF, Maginn EJ. Ionic liquids: innovative fluids for chemical processing. AIChE J. 2001;47:2384–2389.
23. Chau J, Obuskovic G, Jie X, Sirkar KK. Pressure swing membrane absorption process for shifted syngas separation: modeling vs. experiments for pure ionic liquid. J Membr Sci. 2014;453:61–70.
24. Alvarez-Guerra E, Irabien A, Ventura SPM, Coutinho JAP. Ionic liquid recovery alternatives in ionic liquid-based three-phase partitioning (ILTPP). AIChE J. 2014;60:3577–3586.
25. Yin J, Wang J, Li Z, Li D, Yang G, Cui Y, Wang A, Li C. Deep desulfurization of fuels based on an oxidation/extraction process with acidic deep eutectic solvents. Green Chem. 2015;17:4552–4559.
26. Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC. Natural deep eutectic solvents – solvents for the 21st century. ACS Sustain Chem Eng. 2014;2:1063–1071.
27. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V. Novel solvent properties of choline chloride/urea mixtures. Chem Commun. 2003;1:70–71.
28. Dai Y, van Spronsen J, Witkamp GJ, Verpoorte R, Choi YH. Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 2013;766:61–68.
29. Bi W, Tian M, Row KH. Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. J Chromatogr A 2013;1285:22–30.
30. Martins M, Aroso IM, Reis RL, Duarte ARC, Craveiro R, Paiva A. Enhanced performance of supercritical fluid foaming of natural-based polymers by deep eutectic solvents. AIChE J. 2014;60:3701–3706.
31. Pena-Pereira F, Namieśnik J. Ionic liquids and deep eutectic mixtures: sustainable solvents for extraction processes. ChemSusChem. 2014;7:1784–1800.
32. Smith EL, Abbott AP, Ryder KS. Deep eutectic solvents (DESs) and their applications. Chem Rev. 2014;114:11060–11082.
33. Pulati N, Lupinsky A, Miller B, Painter P. Extraction of bitumen from oil sands using deep eutectic ionic liquid analogues. Energy Fuels 2015;29:4927–4935.
34. Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM. Using deep eutectic solvents based on methyl triphenyl phosphunium bromide for the removal of glycerol from palm-oil-based biodiesel. Energy Fuels 2011;25:2671–2678.
35. Leron RB, Li M-H. Solubility of carbon dioxide in a choline chloride–ethylene glycol based deep eutectic solvent. Thermochim Acta 2013;551:14–19.
36. Mulyono S, Hizaddin HF, Alnashef IM, Hashim MA, Fakeeha AH, Hadj-Kali MK. Separation of BTEX aromatics from n-octane using a (tetrabutylammonium bromide + sulfolane) deep eutectic solvent - experiments and COSMO-RS prediction. RSC Adv. 2014;4:17597–17606.
37. Yang D, Hou M, Ning H, Zhang J, Ma J, Yang G, Han B. Efficient SO2 absorption by renewable choline chloride-glycerol deep eutectic solvents. Green Chem. 2013;15:2261–2265.
38. Zhang H, Tang B, Row K. Extraction of catechin compounds from green tea with a new green solvent. Chem Res Chin Univ. 2014;30:37–41.
39. García A, Rodríguez-Juan E, Rodríguez-Gutiérrez G, Rios JJ, Fernández-Bolaños J. Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). Food Chem. 2016;197:554–561.
40. Hou Y, Li Z, Ren S, Wu W. Separation of toluene from toluene/alkane mixtures with phosphonium salt based deep eutectic solvents. Fuel Process Technol. 2015;135:99–104.
41. Lei Z, Dai C, Chen B. Gas solubility in ionic liquids. Chem Rev. 2014;114:1289–1326.
42. Abbott AP, Capper G, Gray S. Design of improved deep eutectic solvents using hole theory. ChemPhysChem. 2006;7:803–806.
43. Shannon MS, Tedstone JM, Danielsen SPO, Hindman MS, Irvin AC, Bara JE. Free volume as the basis of gas solubility and selectivity in imidazolium-based ionic liquids. Ind Eng Chem Res. 2012;51:5565–5576.
44. Klamt A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena. J Phys Chem. 1995;99:2224–2235.
45. Eckert F, Klamt A. Fast solvent screening via quantum chemistry: COSMO-RS approach. AIChE J. 2002;48:369–385.
46. Yang Q, Xing H, Bao Z, Su B, Zhang Z, Yang Y, Dai S, Ren Q. One of the distinctive properties of ionic liquids over molecular solvents and inorganic salts: enhanced basicity stemming from the electrostatic environment and “free” microstructure. J Phys Chem B 2014;118:3682–3688.
47. Guo W, Hou Y, Ren S, Tian S, Wu W. Formation of deep eutectic solvents by phenols and choline chloride and their physical properties. J Chem Eng Data 2013;58:866–872.
48. Yang Q, Xing H, Cao Y, Su B, Yang Y, Ren Q. Selective separation of tocopherol homologues by liquid−liquid extraction using ionic liquids. Ind Eng Chem Res. 2009;48:6417–6422.