Tetrabutylammonium bromide (TBABr)-Based deep eutectic solvents (DESs) and their physical properties

Molecules

Volumn 19, Issue 6, 2014, Pages 8011-8026

  Yusof, Rizana ^a,b   Abdulmalek, Emilia ^a   Sirat, Kamaliah ^a   Rahman, Mohd Basyaruddin Abdul ^a  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITI TEKNOLOGI MARA   (Malaysia)

Author keywords

Deep eutectic solvent; Density; Ionic conductivity; Tetrabutylammonium bromide; Viscosity

Indexed keywords

QUATERNARY AMMONIUM DERIVATIVE; SOLVENT; TETRABUTYLAMMONIUM;

CHEMISTRY; VISCOSITY;

QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS; VISCOSITY;

EID: 84903289203     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19068011     Document Type: Article

References (41)

1. Gorke J.T.; Srienc F.; Kazlauskas R.J. Toward advanced ionic liquids. Polar enzyme-friendly solvents for biocatalysis. Biotechnol. Bioprocess Eng. 2010 15 40-53.
2. Gorke J.T.; Srienc F.; Kazlauskas R.J. Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem. Commun. (Camb.) 2008 10 1235-1237.
3. Dhake K.P. Qureshi Z.S. Singhal R.S. Bhanage B.M. Candida antarctica lipase B-catalyzed synthesis of acetamides using [BMIM(PF6)] as a reaction medium Tetrahedron Lett. 2009 50 2811-2814.
4. Olivier-Bourbigou H.; Magna L.; Morvan D. Ionic liquids and catalysis: Recent progress from knowledge to applications. Appl. Catal. A Gen. 2010 373 1-56.
5. Tavares A.P.M.; Rodrí guez O.; Macedo E.A. New Generations of Ionic Liquids Applied to Enzymatic Biocatalysis. In Ionic Liquids-New Aspects for the Future; Kadokawa J. Ed.; InTech: Rijeka Croatia 2013; pp. 537-556. Available online: http://www.intechopen.com/books/ionicliquids-new-aspects-for- the-future/new-generations-of-ionic-liquids-applied-to-enzymatic-biocatalysis (accessed on 2 March 2013).
6. Lau R.M.; Van Rantwijk F.; Seddon K.R.; Sheldon R.A. Lipase-Catalyzed Reactions in Ionic Liquids. Org. Lett. 2000 2 1-3.
7. Ventura S.P.M.; Gonç alves A.M.M.; Sintra T.; Pereira J.L.; Gonç alves F.; Coutinho J.A.P. Designing ionic liquids: The chemical structure role in the toxicity. Ecotoxicology 2013 22 1-12.
8. Egorova K.S.; Ananikov V.P. Toxicity of ionic liquids: Eco(cyto)activity as complicated but unavoidable parameter for task-specific optimization. ChemSusChem 2014 7 336-360.
9. Zhang Q.; de Oliveira Vigier K.; Royer S.; Jérô me F. Deep eutectic solvents: Syntheses properties and applications. Chem. Soc. Rev. 2012 41 7108-7146.
10. Domí nguez de María P.; Maugeri Z. Ionic liquids in biotransformations: From proof-of-concept to emerging deep-eutectic-solvents. Curr. Opin. Chem. Biol. 2011 15 220-225.
11. Abbott A.P.; Capper G.; Davies D.L.; Rasheed R.K.; Tambyrajah V. Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. (Camb.) 2003 1 70-71.
12. Abbo tt A.P.; Boothby D.; Capper G.; Davies D.L.; Rasheed R.K. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. J. Am. Chem. Soc. 2004 126 9142-914 7.
13. Francisco M.; van den Bruinhorst A.; Zubeir L.F.; Peters C.J.; Kroon M.C. A new low transition temperature mixture (LTTM) formed by choline chloride + lactic acid: Characterization as solvent for CO2 capture. Fluid Phase Equilib. 2013 340 77-84.
14. Harris R.C. Physical Properties of Alcohol Based Deep Eutectic Solvents. PhD Thesis University of Leicester Leicester UK August 2008.
15. Maugeri Z.; Domí nguez de María P. Novel choline-chloride-based deep-eutectic-solvents with renewable hydrogen bond donors: Levulinic acid and sugar-based polyols. RSC Adv. 2012 2 4 21-425.
16. Ru C.; König B. Low melting mixtures in organic synthesis-an alternative to ionic liquids? Green Chem. 2012 14 2969-2982.
17. Zhao H.; Baker G.A.; H olmes. S. New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel. Org. Biomol. Chem. 2011 9 1908-1916.
18. Chary M.V.; Keerthysri N.C.; Vupallapati S.V.N.; Lingai ah N.; Kantevari S. Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient novel neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles. Catal. Commun. 2008 9 2013-2017.
19. Jain N.; Kumar A.; Chauhan S.; Chauhan S.M.S. Chemical and biochemical transformations in ionic liquids. Tetrahedron 2005 61 1015-1060.
20. Duan E.; Guo B.; Zhan g M.; Yang B.; Zhang D. pH Measurements of Caprolactam Tetrabutyl Ammonium Bromide Ionic Liquids in Solvents. J. Chem. Eng. Data 2010 55 3278-3281.
21. Hayyan A.; Mjalli F.S.; AlNashef I .M.; Al-Wahaibi T.; Al-Wahaibi Y.M.; Hashim M.A. Fruit sugar-based deep eutectic solvents and their physical properties. Thermochim. Acta 2012 541 70-75.
22. Hayyan A.; Mjalli F.S.; AlNashef I.M.; Al-Wahaibi Y.M.; Al-Wahaibi T.; Hashim M.A. Glucose-based deep eutectic solvents: Physical properties. J. Mol. Liq. 2013 178 137-141.
23. Kareem M.A.; Mjalli F.S.; H ashim M.A.; Alnashef I.M. Phosphonium-Based Ionic Liquids Analogues and Their Physical Properties. J. Chem. Eng. Data 2010 55 4632-4637.
24. Francisco M.; van den Bruinhorst A.; Kroon M.C. Low-transition- temperature mixtures (LTTMs): A new generation of designer solvents. Angew. Chem. Int. Ed. Engl. 2013 52 3074-3085.
25. Ram írez-Verduzco L.F. Density and viscosity of biodiesel as a function of temperature: Empirical models. Renew. Sustain. Energy Rev. 2013 19652-665.
26. Hayyan A.; Hashim M.A.; Mjalli F.S.; Hayyan M.; AlNashef I.M. A novel phosphoniumbased deep eutectic catalyst for biodiesel production from industrial low grade crude palm oil. Chem. Eng. Sci. 2013 92 81-88.
27. Ghatee M.H.; Zare M.; Mo osavi F.; Zolghadr A.R. Temperature-Dependent Density and Viscosity of the Ionic Liquids 1-Alkyl-3-methylimidazolium Iodides: Experiment and Molecular Dynamics Simulation. J. Chem. Eng. Data 2010 55 3084-3088.
28. Pacak P. Refractivity and density of some organic solvents. Chem. Pap. 1991 45 227-232.
29. Abbott A.P.; Barron J.C.; Ryder K.S.; Wilson D. Eutectic-based ionic liquids with metalcontaining anions and cations. Chem. Eur. J. 2007 13 6495-6501.
30. Ribe J.; Onink F.; Meindersma G.W.; de Haan B. Density viscosity and surface tension of synthesis grade imidazolium pyridini um and pyrrolidinium based room temperature ionic liquids. J. Chem. Eng. Data 2009 54 2803-2812.
31. Ghatee M.H.; Bahrami M.; Khanjari N. Measurement and study of density surface tension and visc osity of quaternary ammonium-based ionic liquids ([N222(n)]Tf2N). J. Chem. Thermodyn. 2013 65 42-52.
32. Abbott A.P.; Harris R.C.; Ryder K.S.; D'Agostino C.; Gladden L.F.; Mantle M.D. Glycerol eutectics as sustainable solvent systems. Green Chem. 2011 13 82-90.
33. Yue D.; Jing Y.; Ma J.; Yao Y.; Jia Y. Physicochemical properties of ionic liquid analogue cont aining magnesium chloride as temperature and composition dependence. J. Therm. Anal. Calorim. 2011 110 773-780.
34. Bonhô te P.; Dias A.P.; Armand M.; Papageorgiou N.; Kalyanasundaram K.; Grä tzel M. Hydrophobic Highly Conductive Ambient-Temperature Molten Salts. Inorg. Chem. 1998 37 1168-1178.
35. Abbott A.P.; Capper G.; Davies D.L.; Rasheed R.K. Ionic liquid analogues formed from hydrated metal salts. Chem. Eur. J. 2004 10 3769-3774.
36. Abbott A.P.; Capper G.; Gray S. Design of improved deep eutectic solvents using hole theory. ChemPhysChem 2006 7 803-806.
37. Dikio E.D.; Nelana S.M.; Isabirye D.A. ; Ebenso E.E. Density dynamic viscosity and derived properties of binary mixtures of methanol ethanol n-propanol and n-butanol with pyridine at T = (293.15 303.15 313.15 and 323.15) K. Int. J. Electrochem. Sci. 2012 7 11101-11122.
38. Herná ndez-Galván M.A.; García-Sánchez F.; Mací as-Salinas R. Liquid viscosities of benzene n-tetradecane and benzene + n-tetradecane from 313 to 393 K and pressures up to 60 MPa: Experiment and modeling. Fluid Phase Equilib. 2007 262 51-60.
39. Ochȩdzan-SiodZak W.; Dziubek K.; SiodZak D. Densities and viscosities of imidazolium and pyridinium chloroaluminate ionic liquids. J. Mol. Liq. 2013 177 85-93.
40. Abdul R ahman M.B.; Jumbri K.; Basri M.; Abdulmalek E.; Sirat K.; Salleh A.B. Synthesis and physico-chemical properties of new tetraethylammonium-based amino acid chiral ionic liquids. Molecules 2010 15 2388-2397.
41. Bandré s I.; Montano D.F.; Gascón I.; Cea P.; Lafuente C. Study of the conductivity behavior of pyridinium-based ionic liquids. Electrochim. Acta 2010 55 2252-2257.