[N+]([O-])(O)=O.O.[CH3:6][C:7]([CH3:9])=[O:8].[CH3:10][C:11]([CH2:13][CH3:14])=[O:12].O1[CH2:19][CH2:18][CH2:17][CH2:16]1>O1CCOCC1.C(O)C.CO.C(O)CCC.C(O)(C)C.C(O)CC>[C:7]1(=[O:8])[CH2:9][CH2:13][CH2:11][CH2:10][CH2:6]1.[CH2:11]([OH:12])[CH2:13][CH2:14][CH2:6][CH2:7][CH2:9][CH2:16][CH2:17][CH2:18][CH3:19]The conditions that can be used above in subjecting the lignin-containing material to reaction with nitric acid must be mild. The reaction can be carried out using an aqueous mixture containing the lignin-containing material and aqueous nitric acid. The nitric acid used can have a concentration of about 5 to about 100 weight percent nitric acid, preferably about 15 to about 70 weight percent nitric acid. The mixture can contain about 0 to about 95 weight percent water, preferably about 40 to about 80 weight percent water. On a weight basis, the lignin-containing material (on a dry basis) and the nitric acid (as 100 percent nitric acid) can be in the range of about 1:0.1 to about 1:10, preferably about 1:1 to about 1:2. The above is mixed while it is maintained in a temperature range of about -10° to about 150° C., preferably about 20° to about 100° C., and a pressure of about 14.5 to about 1000 pounds per square inch gauge, preferably about 14.5 to about 100 pounds per square inch gauge, for about 1 minute to about 10 hours, preferably about 0.5 to about 2 hours. The resulting reaction product is then subjected to extraction with any suitable polar solvent, for example, a ketone, such as acetone, methylethylketone, cyclohexanone, etc., an alcohol, such as methanol, ethanol, normal propanol, isopropanol, butanol, decanol, and mixtures of the lower alcohols, such as those obtained in the industrial production of fuel grade methanol and ethanol, etc., tetrahydrofuran, dioxane, etc., or mixtures thereof. The extraction can be carried out at temperatures in the range of about 0° to about 200° C. and the extraction can be continued until no further extract is obtained. Removal of polar solvent from the extract can be effected by subjecting the extract to drying or distillation. The solid material obtained is the novel alcohol soluble product used herein.
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