Syntheses and physical properties of 1-alkoxydiglycerids as insulating oil

SungChun Lee; Hayun Lee; Eun-kyung Kang; Man Sig Lee; Byung Min Lee

Journal of Industrial and Engineering Chemistry, Vol.25, 314-320, May, 2015

DOI10.1016/j.jiec.2014.10.041 Export Citation

Syntheses and physical properties of 1-alkoxydiglycerids as insulating oil

SungChun Lee^{1, 2}, Hayun Lee^{1, 2}, Eun-kyung Kang^{1, 2}, Man Sig Lee³, and Byung Min Lee^{1, 2, †}

¹Department of Green Chemistry and Environmental Biotechnology, University of Science and Technology, 217 Gajeong-ro, Yuseong-gu, Daejeon 305-333, Republic of Korea
²Surface Materials Research Group, Green Chemistry Division, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon 305-600, Republic of Korea
³Green Technology Center, Korea Institute of Industrial Technology, 45, Jongga-ro, Jung-gu, Ulsan 681-310, Republic of Korea

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Vegetable oils are used for insulating oil, but the oils can be readily decomposed by moisture and heat to fatty acids and other oxidation compounds. To solve these problems, oils containing two ester groups and one ether group were synthesized by using alkyl glycidyl ethers and alkanoyl chloride. The yields of the products were in the range of 90?95%. The pour point, viscosity, thermal stability, and biodegradability of the products were tested as well. Pour point of the vegetable oil derivatives is low, and the biodegradability of the products is 85% or even higher.

Keywords:Insulating oil;Alkanoyl chloride;Alkylglycerol;Alkoxydiglycerides;Ether group

[References]

Sheppard HR, IEEE Electric. Insul. Mag., 121 (1986)
Neville K, Handbook of Epoxy Resins, McGraw Hill Book Company, 1967, pp. 78-87.
Linsley KR, Nonflammable small power transformers, American Power Conference, April 29, (1981), pp. 2-7.
Fofana I, Wasserberg V, Borsi H, Gcockenbach E, IEEE Electric. Insul. Mag., 18, 18 (2002)
Renee IA, Afaf RT, Proc. 9th Int. Seminar, The Production of Insulating Oils of Maximum Oxidation Resistance, Cairo, (1994), pp. 254-261.
Reid LE, Gudelis DA, Low pour point transformer oils from paraffinic crudes, US Patent 4,018,666 (1977).
Mercier G, WEMCOL Capacitor Fluid Development, Electrical/Electronics Insulation Conference, Chicago, (1977), pp. 13-48.
Shankar V, Bashishth SK, Gary V, Pasrichal PS, Transformer’s History and its Insulating Oil, Proc. 5th National Conf., New Delhi, March, (2011), p. 45.
Nishikawa S, Oil insulators for electric apparatus, Jpn. Patent 61,260,503 (1986).
Oommen TV, Claiborne CC, Electrical transformers containing electrical insulation fluids comprising high oleic acid oil composition, US Patent 5,949,017 (1999).
Garcı´a-Zapateiro LA, Franco JM, Valencia C, Delgado MA, Gallegos C, J. Ind. Eng. Chem., 19(4), 1289 (2013)
Hong IK, Jeon GS, Lee SB, J. Ind. Eng. Chem., 20(4), 2348 (2014)
Hong IK, Park JW, Kim H, Lee SB, J. Ind. Eng. Chem., 20(5), 3689 (2014)
Goedde GL, Yerges AP, Dielectric fluid for use in power distribution equipment, US Patent 5,766,517 (1998).
Salimon J, Salih N, Yousif E, J. Lipid Sci. Tech., 112, 519 (2010)
Salimon J, Salih N, Yousif E, J. King Saud Uni. Sci., 24, 11 (2012)
Lee BM, The Synthetic Method of Glycidylether without Solvent and Water, Kor. Patent 10-2000-0023327 (2000).
Lligadas G, Ronda JS, Galia M, Cadiz V, ACS, 2825 (2010)
Weiss SB, Kennedy EP, J. Am. Chem. Soc., 78, 3550 (1956)
Noh JK, Noh CS, Noh HS, Park YH, Manufacturing method of insulating oil used vegetable oil and the isolating oil by the method, Kor. Patent 10-2006-0040064 (2006).
Kwon TH, Insulating oil for eco-environment and manufacturing method thereof, Kor. Patent 10-2009-0111443 (2009).
Smith JM, Organic Chemistry, second ed., McGraw-Hill Company, Inc., 2008, pp. 25-28.
Hemmer M, Badent R, Schwab AJ, Electrical Properties of Rape-seed Oil, Annual Report Conference on Electrical Insulation and Dielectric Phenomena, France, (2002), pp. 83-86.

[1] Sheppard HR, IEEE Electric. Insul. Mag., 121 (1986)

[2] Neville K, Handbook of Epoxy Resins, McGraw Hill Book Company, 1967, pp. 78-87.

[3] Linsley KR, Nonflammable small power transformers, American Power Conference, April 29, (1981), pp. 2-7.

[4] Fofana I, Wasserberg V, Borsi H, Gcockenbach E, IEEE Electric. Insul. Mag., 18, 18 (2002)

[5] Renee IA, Afaf RT, Proc. 9th Int. Seminar, The Production of Insulating Oils of Maximum Oxidation Resistance, Cairo, (1994), pp. 254-261.

[6] Reid LE, Gudelis DA, Low pour point transformer oils from paraffinic crudes, US Patent 4,018,666 (1977).

[7] Mercier G, WEMCOL Capacitor Fluid Development, Electrical/Electronics Insulation Conference, Chicago, (1977), pp. 13-48.

[8] Shankar V, Bashishth SK, Gary V, Pasrichal PS, Transformer’s History and its Insulating Oil, Proc. 5th National Conf., New Delhi, March, (2011), p. 45.

[9] Nishikawa S, Oil insulators for electric apparatus, Jpn. Patent 61,260,503 (1986).

[10] Oommen TV, Claiborne CC, Electrical transformers containing electrical insulation fluids comprising high oleic acid oil composition, US Patent 5,949,017 (1999).

[11] Garcı´a-Zapateiro LA, Franco JM, Valencia C, Delgado MA, Gallegos C, J. Ind. Eng. Chem., 19(4), 1289 (2013)

[12] Hong IK, Jeon GS, Lee SB, J. Ind. Eng. Chem., 20(4), 2348 (2014)

[13] Hong IK, Park JW, Kim H, Lee SB, J. Ind. Eng. Chem., 20(5), 3689 (2014)

[14] Goedde GL, Yerges AP, Dielectric fluid for use in power distribution equipment, US Patent 5,766,517 (1998).

[15] Salimon J, Salih N, Yousif E, J. Lipid Sci. Tech., 112, 519 (2010)

[16] Salimon J, Salih N, Yousif E, J. King Saud Uni. Sci., 24, 11 (2012)

[17] Lee BM, The Synthetic Method of Glycidylether without Solvent and Water, Kor. Patent 10-2000-0023327 (2000).

[18] Lligadas G, Ronda JS, Galia M, Cadiz V, ACS, 2825 (2010)

[19] Weiss SB, Kennedy EP, J. Am. Chem. Soc., 78, 3550 (1956)

[20] Noh JK, Noh CS, Noh HS, Park YH, Manufacturing method of insulating oil used vegetable oil and the isolating oil by the method, Kor. Patent 10-2006-0040064 (2006).

[21] Kwon TH, Insulating oil for eco-environment and manufacturing method thereof, Kor. Patent 10-2009-0111443 (2009).

[22] Smith JM, Organic Chemistry, second ed., McGraw-Hill Company, Inc., 2008, pp. 25-28.

[23] Hemmer M, Badent R, Schwab AJ, Electrical Properties of Rape-seed Oil, Annual Report Conference on Electrical Insulation and Dielectric Phenomena, France, (2002), pp. 83-86.