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1 : *,.,...,., 5,, ( ), t-fedulina@yandex.ru (0,5, 1 ), - ( ), - ( ) 13., 13.,,. :,,,, -,,, 13.,, ( ). - [1]., -, ( ) [2] [3]. 13, [4]. 13,.,, t-fedulina@yandex.ru,, 1, 2 -, 3, 4 5 -, [5], 6 - [6]. ( ) [7]. 13 -d 6 Varian-Gemini ,3 *,.
2 44.,.,. [8]. 13 0,5 NaOD 0,5 NaOD- -d 6 Varian-Gemini , , ,25. -NaOH NaOH 0,5, 3 : 7. 1 NaOH Bruker AC ,2 [8]. 13 [9].,, 150., 1,8 2,0. [8] -.,, ( 3-( )- -2,2,3,3-d 4 D 2 O) (1 4) (5, 6) -d 6, NaOH (0,5 1 ).., C-1 C-4 NaOH 1. -, 13 (1) 1 (.) 5 [8] NaOH. -,, 0,5 - NaOH ( 7 : 3)., -, -, NaOH., -, - [2]. 0,5 NaOH, C-1 C ( 10. ) ( ) (.). ( 3, 4), NaOH 0,5 NaOH -d 6,. - C- - C- NaOH,., - C-1 C-4 NaOH,, - (.) , 1 NaOH, 0,5 NaOH,. -d 6 1 NaOH [8].
3 13 45 (1 4) (5, 6),,. C- C-1 C-2 C-3 C-4 C-5 C-6 1 * -d 6 121,2 129,9 115,8 155,4 115,8 129,9 1 M NaOH 115,6 130,7 119,8 166,7 119,8 130,7 2 * -d 6 119,6 113,4 148,2 147,2 116,1 121,4 0,5 M NaOD: -d 6 112,3 114,4 158,5 152,6 114,9 123,9 0,5 M NaOD 111,2 105,6 149,0 143,5 106,2 114,9 1 M NaOH 114,8 114,1 151,9 157,3 119,7 123,4 3 * -d 6 73,8 137,2 110,1 147,3 145,1 114,9 118,3 0,5 M NaOD: -d 6 77,3 130,3 112,3 157,8 152,2 112,5 121,6 0,5 M NaOD 68,4 121,5 103,3 148,4 143,2 110,4 112,6 1 M NaOH 76,8 130,0 111,9 151,5 156,6 118,9 121,0 4 * -d 6 198,6 128,5 111,0 147,5 151,5 114,9 122,7 0,5 M NaOD: -d 6 205,1 128,6 112,2 152,5 167,9 119,4 127,9 0,5 M NaOD 197,2 119,3 103,3 143,3 158,2 110,2 113,3 1 M NaOH 205,2 121,9 112,0 151,7 166,6 118,7 127,7 5 * -d 6 A 74,0 135,2 110,9 147,2 146,5 112,9 118,8 B 121,2 111,3 148,7 149,9 116,9 120,7 0,5 M NaOD: -d 6 A 76,5 135,0 110,6 146,0 112,6 117,0 B 122,7 112,1 141,9 148,8 114,2 121,0 6 * -d 6 A 70,8 133,0 127,7 114,9 156,7 114,9 127,7 B 121,1 112,6 149,3 148,4 113,8 120,9 1 M NaOH A 72,7 125,9 128,8 119,5 167,0 119,5 128,8 B 122,6 113,1 149,1 148,0 114,3 121,2 * : 1, 2 2- ( ), 3 1-( , 4 1-( , 5 1-(3,4- )-2-(2- -1-, 6 1-(4- )-2-( ,., [10]. - C-1 C-4, -., 157,5., ,8. [11]. C-1 125,7., 133,1. [12]. C-4 C-1 1 NaOH. C- - 71,7. ( ), 73,9. (NaOH), C- 83,9. ( ), 84,3. (NaOH) [8]., 13. -, 1-13.,.,. - -d 6 [8, 13]., 1 NaOH, -,.
4 46.,., NaOH -d 6, C-1 C-4 - -d , - -C-O, - 1 -,,. -.., - (45 48% -O-4 ), -. -,,. ph 13,4, ph 1 NaOH (13,0).,,,, -,,.,, ,, ,. «-».,,,,, C-1 C ,2. C-4, 130,3. C ,2. -3, 124,3. C-6, 115,3. C-2 -, [9, 14]., , 1 NaOH,, [9]. -., 13 -.,,, -. -,, -, -., 13 -,. -.
5 Bennacer E.-M., Kiryushina M.F., Zarubin M.Ya. Effect of organic solvents on cleavage of beta-alkyl-o-arylic bond kinetics // Proceedings of 5 th ISWPC. Raleigh (USA) Pp , Burger K. Solvation, ionic and complex formation reactions in nonaqueous solvents. M., p. 4. Rober D Carbon-13 nuclear magnetic resonance spectrometry // Methods in Lignin Chemistry / eds. S.Y. Lin and C.W. Dence Pp , Shevchenko S.M., Jakobsons J.K., Mishnev A.F., Liepins M.G. The spatial of structure of dilignol -O-4 [1-(4- hydroxyphenyl)-2-(2-methoxy-phenoxy)ethan-1-ol] in crystal and solution // Zhurn. Struct. Khim Vol. 30. Pp Bjorkman A. Studies of finely divided wood. Part I. Extraction of lignin with neutral solvents // Svensk Papperstidn Vol. 59. Pp Akim L.G., Fedulina T.G., Schevchenko S.M. 13 C NMR of lignins in aqueous alkali. I. Ionisation effect on the spectra of model compounds and milled wood lignins // Holzforschung Vol. 50. N3. Pp Shevchenko S.M., Fedulina T.G., Akim L.G. 13 C NMR spectroscopy in aqueous alkali: is it applicable to the black liquor? // Proceedings of 9 th ISWPC. Montreal, Quebec, Canada, Pp. 102(1) 102(4). 10. Sakakibara A. Chemistry of lignin // Wood and Cellulose Chemistry / eds. D.N.-S. Hon and S. Shiraishi Pp Rober D., Chen C.-L. Structural analysis of biodegraded lignins from spruce wood decayed by Phanerochaete chrysosporium by quantitative 13 C NMR spectroscopy // Proceedings of 4 th ISWPC. Paris, France, Vol. 1. Pp Chen C.-L., Rober D. 1 H and 13 C NMR spectroscopy of lignin // Methods in enzimology biomass / eds. W.A. Wood and S.T. Kellog Vol Pp Kiryushina M.F., Fedulina T.G., Soultanov V.S., Zarubin M.Ya. Acid-base interactions of lignin and reaction mixture during alkaline solvolysis // Proceedings of 13 th ISWPC. Auckland, New Zeland, Vol. 3. Pp Akim L.G., Fedulina T.G., Schevchenko S.M. 13 C NMR of lignins in aqueous alkali. II. Ionization effects on the spectra of technical lignins // Holzforschung Vol. 51, N5. Pp Fedulina T.G. *, Kiryushina M.F., Zarubin M.Ya. THE AVAILABILITY OF 13 C NMR SPECTROSCOPY TO THE STUDY OF ALKALINE SOLVOLYSIS OF LIGNIN IN WOOD Saint-Petersburg State Forest Technical University, Institutskiy per., 5, Saint-Petersburg, (Russia), t-fedulina@yandex.ru This article presents the results of investigation of the influence of aqueous sodium hydroxide solutions (0.5M, 1M) containing and not containing of dimethylsulfoxide (DMSO) on the chemical shifts of aromatic carbons of lignin model compounds and spruce milled wood lignin (MWL) in 13 C NMR spectra. It has been established that 13 C NMR spectroscopy may be applied for the study of solvation and ionisation of lignin under alkaline solvolysis by the shift of signals of lignin carbons in above mentioned solutions in comparison with DMSO. It was demonstrated that 13 C NMR spectroscopy is also a convenient method for the study of structure of lignin in situ dissolved in spruce kraft black liquor. Keywords: lignin model compounds, lignin, alkaline solvolysis, sodium hydroxide, dimethylsulfoxide, ionisation, solvation, 13 C NMR spectroscopy. References 1. Bennacer E.-M., Kiryushina M.F., Zarubin M.Ya. Proceedings of 5 th ISWPC. Raleigh (USA), 1989, pp Raikhardt K. Rastvoriteli i effekty sredy v organicheskoi khimii. [Solvents and medium effects in organic chemistry]. oscow, 1991, 763 p. (in Russ.). 3. Burger K. Solvation, ionic and complex formation reactions in nonaqueous solvents. Elsevier, 1984, 286 p. 4. Rober D Carbon-13 nuclear magnetic resonance spectrometry // Methods in Lignin Chemistry. Eds. S.Y. Lin and C.W. Dence Pp Zakis G.F. Sintez model'nykh soedinenii lignina. [Synthesis of lignin model compounds]. Riga, 1980m, 288 p. * Corresponding author.
6 48.,.,. 6. Shevchenko S.M., Jakobsons J.K., Mishnev A.F., Liepins M.G. Zhurn. Struct. Khim, 1989, vol. 30, pp Bjorkman A. Svensk Papperstidn, 1956, vol. 59, pp Akim L.G., Fedulina T.G., Schevchenko S.M. Holzforschung, 1996, vol. 50, no. 3, pp Shevchenko S.M., Fedulina T.G., Akim L.G. Proceedings of 9 th ISWPC. Montreal, Quebec, Canada, 1997, pp. 102(1)- 102(4). 10. Sakakibara A. Chemistry of lignin / Wood and Cellulose Chemistry. Eds. D.N.-S. Hon and S. Shiraishi, 1991, pp Rober D., Chen C.-L. Proceedings of 4 th ISWPC. Paris, France, 1987, vol. 1, pp Chen C.-L., Rober D. Methods in enzimology biomass. Eds. Wood W.A. and Kellog S.T. 1988, vol. 161, pp Kiryushina M.F., Fedulina T.G., Soultanov V.S., Zarubin M.Ya. Proceedings of 13 th ISWPC. Auckland, New Zeland, 2005, vol. 3, pp Akim L.G., Fedulina T.G., Schevchenko S.M. Holzforschung, 1997, vol. 51, no. 5, pp Received December 31, 2011
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