Homogeneous synthesis of cellulose fatty esters in ionic liquid (1-butyl-3-methylimidazolium chloride) and study of their comparative antifriction property

Raj K. Singh; Piyush Gupta; Om P. Sharma; Siddharth S. Ray

Journal of Industrial and Engineering Chemistry, Vol.24, 14-19, April, 2015

DOI10.1016/j.jiec.2014.09.031 Export Citation

Homogeneous synthesis of cellulose fatty esters in ionic liquid (1-butyl-3-methylimidazolium chloride) and study of their comparative antifriction property

Raj K. Singh^†, Piyush Gupta¹, Om P. Sharma, and Siddharth S. Ray

Chemical Science Division, CSIR-Indian Institute of Petroleum, Dehradun 248005, India
¹Analytical Science Division, CSIR-Indian Institute of Petroleum, Dehradun 248005, India

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Cellulose fatty esters with different fatty acids as lauric, myristic, palmitic, stearic and oleic acid having same degrees of substitution (DS ∼ 2.0) were prepared homogeneously using 1-butyl-3-methylimidazolium chloride ([C4mim]+Cl?). All samples were characterized by IR and NMR. The triboevaluation in terms of average friction coefficient was done by nanotribometer using 3000 ppm solution of each ester in polyol (pentaerythritol tetraoleate) which is taken as biolube reference fluid. The cellulose esters are found to show antifriction character in the order as myristate > palmitate > laurate > stearate > oleate.

Keywords:Cellulose fatty ester;Ionic liquid;Degree of substitution;Lubricant additive;Friction coefficient

[References]

Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Green Chem., 11, 686 (2009)
Nunez N, Martın-Alfonso JE, Valencia C, Sanchez MC, Franco JM, Ind. Crop. Prod., 37, 500 (2012)
Roper LE, Sauber CA, US Patent No. 4123366 A (1978).
Saga LC, Rukke EO, Liland KH, Kirkhus B, Egelandsdal B, Karlsen J, Volden J, J. Am. Oil Chem. Soc., 88, 1883 (2011)
Wang P, Tao BY, J. Environ. Polym. Degrad., 3, 115 (1995)
Crepy L, Chaveriat C, Banoub J, Martin P, Joly N, ChemSusChem, 2, 165 (2009)
Tosh B, Saikia CN, Dass NN, Carbohydr. Res., 327, 345 (2000)
Satge C, Granet R, Verneuil B, Branland P, Krausz P, Comptes Rendus Chimie, 7, 135 (2004)
Samaranayake G, Glasser WG, Carbohydr. Polym., 22(2), 79 (1993)
Nagel MCV, Heinze T, Polym. Bull., 65(9), 873 (2010)
Biswas A, Gordon S, Michael A, Woods KK, Willett JL, Buchanan CM, Carbohydr. Polym., 68, 555 (2007)
Swatloski RP, Spear SK, Holbrey JD, Rogers RD, J. Am. Chem. Soc., 124(18), 4974 (2002)
Remsing RC, Swatloski RP, Rogers RD, Moyna G, Chem. Commun., 1271 (2006)
Dorn S, Schobitz M, Schlufter K, Heinze T, ACS Symp. Ser., 1033, 275 (2010)
Zhang J, Wu J, Cao Y, Sang S, Zhang J, He J, Cellulose, 16, 299 (2009)
Huang K, Xia J, Li M, Lian J, Yang X, Lin G, Carbohydr. Polym., 83, 1631 (2011)
Joly N, Granet R, Branland P, Verneuil B, Krausz P, J. Appl. Polym. Sci., 97(3), 1266 (2005)
Lowman DW, ACS Symp. Ser., 688, 131 (1998)
Newman RH, Ha M, Melton LD, J. Agric. Food Chem., 42, 1402 (1994)
Wu J, Zhang J, Zhang H, He JS, Ren Q, Guo M, Biomacromolecules, 5(2), 266 (2004)
Singh RK, Sharma OP, Singh AK, Ind. Eng. Chem. Res., 53(25), 10276 (2014)

[Referenced By]

[1] Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Green Chem., 11, 686 (2009)

[2] Nunez N, Martın-Alfonso JE, Valencia C, Sanchez MC, Franco JM, Ind. Crop. Prod., 37, 500 (2012)

[3] Roper LE, Sauber CA, US Patent No. 4123366 A (1978).

[4] Saga LC, Rukke EO, Liland KH, Kirkhus B, Egelandsdal B, Karlsen J, Volden J, J. Am. Oil Chem. Soc., 88, 1883 (2011)

[5] Wang P, Tao BY, J. Environ. Polym. Degrad., 3, 115 (1995)

[6] Crepy L, Chaveriat C, Banoub J, Martin P, Joly N, ChemSusChem, 2, 165 (2009)

[7] Tosh B, Saikia CN, Dass NN, Carbohydr. Res., 327, 345 (2000)

[8] Satge C, Granet R, Verneuil B, Branland P, Krausz P, Comptes Rendus Chimie, 7, 135 (2004)

[9] Samaranayake G, Glasser WG, Carbohydr. Polym., 22(2), 79 (1993)

[10] Nagel MCV, Heinze T, Polym. Bull., 65(9), 873 (2010)

[11] Biswas A, Gordon S, Michael A, Woods KK, Willett JL, Buchanan CM, Carbohydr. Polym., 68, 555 (2007)

[12] Swatloski RP, Spear SK, Holbrey JD, Rogers RD, J. Am. Chem. Soc., 124(18), 4974 (2002)

[13] Remsing RC, Swatloski RP, Rogers RD, Moyna G, Chem. Commun., 1271 (2006)

[14] Dorn S, Schobitz M, Schlufter K, Heinze T, ACS Symp. Ser., 1033, 275 (2010)

[15] Zhang J, Wu J, Cao Y, Sang S, Zhang J, He J, Cellulose, 16, 299 (2009)

[16] Huang K, Xia J, Li M, Lian J, Yang X, Lin G, Carbohydr. Polym., 83, 1631 (2011)

[17] Joly N, Granet R, Branland P, Verneuil B, Krausz P, J. Appl. Polym. Sci., 97(3), 1266 (2005)

[18] Lowman DW, ACS Symp. Ser., 688, 131 (1998)

[19] Newman RH, Ha M, Melton LD, J. Agric. Food Chem., 42, 1402 (1994)

[20] Wu J, Zhang J, Zhang H, He JS, Ren Q, Guo M, Biomacromolecules, 5(2), 266 (2004)

[21] Singh RK, Sharma OP, Singh AK, Ind. Eng. Chem. Res., 53(25), 10276 (2014)