Study of cystine schiff base esters as new environmentally benign multifunctional biolubricant additives

Raj K. Singh; Shubham Pandey; Rakesh C. Saxena; Gananath D. Thakre; Neeraj Atray; Siddharth S. Ray

Journal of Industrial and Engineering Chemistry, Vol.26, 149-156, June, 2015

DOI10.1016/j.jiec.2014.11.027 Export Citation

Study of cystine schiff base esters as new environmentally benign multifunctional biolubricant additives

Raj K. Singh^†, Shubham Pandey, Rakesh C. Saxena, Gananath D. Thakre¹, Neeraj Atray², and Siddharth S. Ray

Chemical Science Division, CSIR-Indian Institute of Petroleum, Dehradun 248 005, India
¹Tribology Division, CSIR-Indian Institute of Petroleum, Dehradun 248 005, India
²Bio Fuels Division, CSIR-Indian Institute of Petroleum, Dehradun 248 005, India

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Two additives CySBE-A and B were prepared via a two step synthesis. First, the cystine schiff base (CySB) was synthesized utilizing 3,5-di-t-butyl-4-hydroxybenzaldehyde. In the second step, its esterification with lauroyl alcohol and 2-ethyl hexanol results the final products CySBE-A and B respectively. Both additives were evaluated as multifunctional additive in polyol base oil for antioxidant, antifriction, antiwear and anticorrosion property. Universal oxidation test (IP-306) was used for evaluating antioxidant property. Antifriction and antiwear properties in terms of average friction coefficient and wear scar diameter (WSD) were evaluated using four ball test. The CySBE-A was found to be effective than CySBE-B.

Keywords:Cystine schiff base ester;Antioxidant;Antifriction;Antiwear;Anticorrosion

[References]

Rudnick LR, Additives L: Chemistry and Applications, 2nd ed., CRC Press, Taylor & Francis, 2009.
Bartz WJ, Tribol. Int., 31, 35 (1998)
Nagendramma P, Kaul S, Renew. Sust. Energ. Rev., 16, 764 (2012)
Erhan SZ, Asadaukas S, Ind. Crop. Prod., 11, 277 (2000)
Karmakar G, Ghosh P, ACS Sustain. Chem. Eng., 1, 1364 (2013)
Spikes HA, Tribol. Lett., 17, 469 (2004)
Hewstone RK, Sci. Total Environ., 156, 243 (1994)
Swami KK, Prakash S, Sarin R, Tuli DK, Bhatnagar AK, Lubr. Sci., 15, 361 (2013)
Li W, Wu Y, Wang X, Liu W, Tribol. Lett., 47, 381 (2012)
Li W, Jiang C, Chao M, Wang X, ACS Sustain. Chem. Eng., 2, 798 (2014)
Singh RK, Kukrety A, Singh AK, ACS Sustain. Chem. Eng., 2, 1959 (2014)
Saga LC, Rukke EO, Liland KH, Kirkhus B, Egelandsdal B, Karlsen J, Volden J, J. Am. Oil Chem. Soc., 88, 1883 (2011)
Roper LE, Sauber CA, US patent no. 4123366 A (1978).
Singh RK, Sharma OP, Singh AK, Ind. Eng. Chem. Res., 53(25), 10276 (2014)
Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos G, Green Chem., 11, 686 (2009)
Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Carbohydr. Polym., 83, 151 (2011)
Sanchez R, Stringari GB, Franco JM, Valencia C, Gallegos C, Carbohydr. Polym., 85, 705 (2011)
Gallego R, Arteaga JF, Valencia C, Franco JM, Molecules, 18, 6532 (2013)
Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Chem. Eng. Res. Des., 86(10A), 1073 (2008)
Minami I, Mori S, Isogai Y, Hiyoshi S, Inayama T, Nakayama S, Tribol. Trans., 53, 713 (2010)
Khatri PK, Thakre GD, Jain SL, Ind. Eng. Chem. Res., 82, 15829 (2013)
Minami I, Watanabe N, Nanao H, Mori S, Fukumoto K, Ohno H, Chem. Lett., 37(3), 300 (2008)
Singh AK, Singh RK, J. Surfactants Deterg., 15, 399 (2012)
Levin M, Wiklund P, Leygraf C, Corros. Sci., 58, 104 (2012)
IP 306, Institute of Petroleum Testing Methods for Petroleum, Fuel products: High Temperature Universal Oxidation Test Method, Part I, Institute of Petroleum, UK, 2004.
ASTM D4172, Standard Test Method For Wear Preventive Characteristics of Lubricating Fluid (Four-Ball Method), 2010.
Champion FA (Ed.), Corrosion Testing Procedure, Champion & Hall, 1964, p. 66.
Ailor WA (Ed.), Handbook of Corrosion Testing and Evaluation, John Wiley & Sci, Inc., 1971, p. 119.
ASTM D664-11a, Standard Test Method for Acid Number Products by Potentiometric Titration, 2011.
Agarwala VS, Rajan KS, Sen PK, US patent no. 5,147,567 (1992).
Gopi D, Govindaraju KM, Kavitha L, J. Appl. Electrochem., 40(7), 1349 (2010)
Emregul KC, Akay AA, Atakol O, Mater. Chem. Phys., 93(2-3), 325 (2005)
Shokry H, Yuasa M, Sekine I, Issa RM, El-baradie HY, Gomma GK, Corrosion Sci., 40, 2173 (1998)
Wan Y, Liu WM, Xue Q, Lubr. Sci., 7, 187 (1995)

[Referenced By]

[1] Rudnick LR, Additives L: Chemistry and Applications, 2nd ed., CRC Press, Taylor & Francis, 2009.

[2] Bartz WJ, Tribol. Int., 31, 35 (1998)

[3] Nagendramma P, Kaul S, Renew. Sust. Energ. Rev., 16, 764 (2012)

[4] Erhan SZ, Asadaukas S, Ind. Crop. Prod., 11, 277 (2000)

[5] Karmakar G, Ghosh P, ACS Sustain. Chem. Eng., 1, 1364 (2013)

[6] Spikes HA, Tribol. Lett., 17, 469 (2004)

[7] Hewstone RK, Sci. Total Environ., 156, 243 (1994)

[8] Swami KK, Prakash S, Sarin R, Tuli DK, Bhatnagar AK, Lubr. Sci., 15, 361 (2013)

[9] Li W, Wu Y, Wang X, Liu W, Tribol. Lett., 47, 381 (2012)

[10] Li W, Jiang C, Chao M, Wang X, ACS Sustain. Chem. Eng., 2, 798 (2014)

[11] Singh RK, Kukrety A, Singh AK, ACS Sustain. Chem. Eng., 2, 1959 (2014)

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

[13] Roper LE, Sauber CA, US patent no. 4123366 A (1978).

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

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

[16] Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Carbohydr. Polym., 83, 151 (2011)

[17] Sanchez R, Stringari GB, Franco JM, Valencia C, Gallegos C, Carbohydr. Polym., 85, 705 (2011)

[18] Gallego R, Arteaga JF, Valencia C, Franco JM, Molecules, 18, 6532 (2013)

[19] Sanchez R, Franco JM, Delgado MA, Valencia C, Gallegos C, Chem. Eng. Res. Des., 86(10A), 1073 (2008)

[20] Minami I, Mori S, Isogai Y, Hiyoshi S, Inayama T, Nakayama S, Tribol. Trans., 53, 713 (2010)

[21] Khatri PK, Thakre GD, Jain SL, Ind. Eng. Chem. Res., 82, 15829 (2013)

[22] Minami I, Watanabe N, Nanao H, Mori S, Fukumoto K, Ohno H, Chem. Lett., 37(3), 300 (2008)

[23] Singh AK, Singh RK, J. Surfactants Deterg., 15, 399 (2012)

[24] Levin M, Wiklund P, Leygraf C, Corros. Sci., 58, 104 (2012)

[25] IP 306, Institute of Petroleum Testing Methods for Petroleum, Fuel products: High Temperature Universal Oxidation Test Method, Part I, Institute of Petroleum, UK, 2004.

[26] ASTM D4172, Standard Test Method For Wear Preventive Characteristics of Lubricating Fluid (Four-Ball Method), 2010.

[27] Champion FA (Ed.), Corrosion Testing Procedure, Champion & Hall, 1964, p. 66.

[28] Ailor WA (Ed.), Handbook of Corrosion Testing and Evaluation, John Wiley & Sci, Inc., 1971, p. 119.

[29] ASTM D664-11a, Standard Test Method for Acid Number Products by Potentiometric Titration, 2011.

[30] Agarwala VS, Rajan KS, Sen PK, US patent no. 5,147,567 (1992).

[31] Gopi D, Govindaraju KM, Kavitha L, J. Appl. Electrochem., 40(7), 1349 (2010)

[32] Emregul KC, Akay AA, Atakol O, Mater. Chem. Phys., 93(2-3), 325 (2005)

[33] Shokry H, Yuasa M, Sekine I, Issa RM, El-baradie HY, Gomma GK, Corrosion Sci., 40, 2173 (1998)

[34] Wan Y, Liu WM, Xue Q, Lubr. Sci., 7, 187 (1995)