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Synthesis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols and the properties of related sulfides

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Abstract

Reaction of 2,6-di-tert-butylphenol with aliphatic linear and branched diols in an alkaline medium at a temperature of 180-220°C leads to the formation of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols. The increase in the product yield and reducing the reaction temperature was reached at the catalysis of this reaction with zinc oxide. The structure of the diphenylalkane derivatives generated in side reaction was proved and the structural influence of the length of the aliphatic residue on the antioxidant effectiveness of the sulfides derived from the corresponding hydroxyalkylphenols was examined.

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References

  1. Ershov, V.V., Volod’kin, A.A., Kudrina, L.I., and Vol’eva, V.B., USSR Inventor’s Certificate no. 727614, 1978, Byul. Izobret., 1980, no. 14.

  2. Krysin, A.P., Pustovskikh, I.I., Borisenko, L.A., Koptyug, V.A., and Gorodetskaya, N.N., USSR Inventor’s Certificate no. 877918, 1979, Byul. Izobret., 2009, no. 26.

  3. Parker, D.K. and Kline, R.H., US Patent no. 4260832, 1979, Chem. Abstr., 1981, vol. 95, no. 9, P80467g.

    Google Scholar 

  4. Krysin, A.P. and Pokrovskii, L.M., Zh. Obshch. Khim., 2008, vol 78, no. 9, pp. 1496–1501.

    Google Scholar 

  5. Krysin, A.P. and Khalikova, N.U., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., 1984, no. 2, pp. 131–132

  6. Nikulicheva, O.N., Krysin, A.P., and Fadeeva, V.P., Zh. Prikl. Khim., 2008, vol. 81, no. 9, pp. 1517–1522.

    Google Scholar 

  7. Prosenko, A.E., Markov, A.F., Pinko, P.I., Krysin, A.P., and Koptyug, V.A., USSR Inventor’s Certificate no. 1658601, 1989, Byul. Izobret., 1995, no. 26.

  8. Lugova, L.I., Makarova, G.P., Tsvetkova, A.I., Sotnikova, L.K., Dudinova, L.N., and Lazareva, N.P., Coll. of Publications: Organic Compounds, New Stabilizers. Synthesis, Properties, and Processing of Polyphenols, Leningrad: Plastpolymer, 1984, pp. 152–158.

    Google Scholar 

  9. Demidov,a V.M., Lugova, L.I., Prosenko, A.E., Kim, A.M., Koptyug, V.A., Krysin, A.P., Shiryaeva, L.V., and Dudinova, L.N., USSR Inventor’s Certificate no. 979428, 1981, Byul. Izobret., 1982, no. 45.

  10. Makarova, G.P., Lugova, L.I., Prosenko, A.E., Kim, A.M., Koptyug, V.A., Krysin, A.P., Sotnikova, L.K., Tsvetkova, A.I., Lazareva, N.P., Sokolova, T.G., Kirillova, E.I., Emel’yanova, A.T., Lenin, E.S., Kuznetsova, S.V., and Malakhova, G.P., USSR Inventor’s Certificate no. 988840, 1983, Byul. Izobret., 1983, no. 2.

  11. Storozhok, N.M., Gureeva, N.V., and Krysin, A.P., Nauchnyi Vestnik Tomskoi Med. Akad., 2003, vol. 23, no. 1, pp. 18–22.

    Google Scholar 

  12. Perevozkina, M.G., Storozhok, N.M., Krysin, A.P., and Borisenko, V.E., Izv. Akad. Nauk, Ser. Khim., 2006, no. 8, pp. 1330–1337.

  13. Anisimova, I.L., Krysin, A.P., and Storozhenko, V.G., Atlas spektrov aromaticheskikh i geterotsiklicheskikh soedinenii. IK-, UF- i PMR-spektry 2-tret-butyl- i 2,6-di-tret-butylfenolov (Atlas of the Spectra of Aromatic and Heterocyclic Compounds. IR, UV, and 1H NMR Spectra of 2-tert-Butyl- and 2,6-Di-tert-butylphenols), Koptyug, V.A., Ed., Novosibirsk, 1983, no. 25.

  14. Plekhanova, L.G., Nikifopov, G.A., Ershov, V.V., and Zakharov, E.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1973, no. 4, p. 843.

  15. Gorbunov, B.N., Gurvich, Ya.A., and Maslova, I.P., Khimiya i tekhnologiya stabilizatorov polimernykh materialov (Chemistry and Technology of the Stabilizers of Chemical Materials), Moscow: Khimiya, 1981, p. 255.

    Google Scholar 

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Correspondence to A. P. Krysin.

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Original Russian Text © A.P. Krysin, I.I. Pustovskikh, V.A. Koptyug, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 10, pp. 1691–1696.

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Krysin, A.P., Pustovskikh, I.I. & Koptyug, V.A. Synthesis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols and the properties of related sulfides. Russ J Gen Chem 80, 2001–2006 (2010). https://doi.org/10.1134/S1070363210100208

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  • DOI: https://doi.org/10.1134/S1070363210100208

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