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(12) Patent Application Publication (10) Pub. No.: US 2014/0110070 A1 Vuorinen Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0110070 A1 Vuorinen Et Al US 201401 10070A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0110070 A1 Vuorinen et al. (43) Pub. Date: Apr. 24, 2014 (54) METHOD FORCATALYTICOXIDATION OF (30) Foreign Application Priority Data CELLULOSE AND METHOD FOR MAKINGA CELLULOSE PRODUCT Jun. 9, 2011 (FI) ...................................... 2O115566 (75) Inventors: Tapani Vuorinen, Espoo (FI); Timo Publication Classification Paikkönen, Helsinki (FI); Markus Nuopponen, Helsinki (FI) (51) Int. Cl. D2C3/00 (2006.01) (73) Assignee: UPM-KYMMENE CORPORATION, (52) U.S. Cl. Helsinki (FI) CPC ...................................... D21C3/003 (2013.01) USPC ............................. 162/60: 162/73; 162/181.1 (21) Appl. No.: 14/124,520 (57) ABSTRACT (22) PCT Filed: Jun. 8, 2012 In a method for catalytic oxidation of cellulose a heterocyclic nitroxyl radical is used as catalyst, hypochlorite is used as (86). PCT No.: PCT/F2012/050573 main oxidantacting as oxygen Source, and a tertiary amine or S371 (c)(1), chlorine dioxide as an activator of the heterocyclic nitroxyl (2), (4) Date: Dec. 6, 2013 radical. Patent Application Publication Apr. 24, 2014 Sheet 1 of 11 US 2014/0110070 A1 & (pulp 10) conventional NaBr assisted TEMPO oxidation S (pulp 26) hexamethylenetetram ine assisted TEMPO oxidation : (pulp 31) DABCO assisted TEMPO oxidation X (pulp 36) duinuclidine y s y * Ys S s assisted TEMPO O 50 1OO 150 2OO 250 oxidation Time, min FIG. 1 Patent Application Publication Apr. 24, 2014 Sheet 2 of 11 US 2014/0110070 A1 60 due Š (pulp. 18) duinuclidine assisted TEMPO oxidation (5.3 mmol NaClO/g pulp) ... (pulp 20) quinuclidine aSSisted TEMPO oxidation (7.1 mmol NaClO/g pulp) Time, min FIG 2 time, min FIG. 3 Patent Application Publication Apr. 24, 2014 Sheet 3 of 11 US 2014/0110070 A1 O 5O 1OO 150 200 250 300 time, min FIG. 4 0,50 0.45 0.40 0.35 0.30 0.25 0.20 10 15 2.0 2,5 3,O 3.5 40 45 5.0 55 mmol NaClO 1 g pulp FIG. 5 Patent Application Publication Apr. 24, 2014 Sheet 4 of 11 US 2014/0110070 A1 12 11 1,0 0,9 O,8 O.7 O,6 0.5 0.4 O,3 0.2 0,1 O,O mmol COOH 1 g pulp (1-phase) FIG. 6 240 220 2OO 18O 16O 140 12O 1OO 8O 6O 40 2O O 5O 1 OO 15O 200 25O 3OO 350 4OO 45O 5OO 55O 6OO 2-phase viscosity (ml/g) FIG. 7 Patent Application Publication Apr. 24, 2014 Sheet 5 of 11 US 2014/0110070 A1 1 2 D carboxylates 10 aldehydes O O O O,8 O O 50 1OO 150 200 time, min FIG. 8 O,38 0.36 0,34 O,30 1,0 15 2,0 2,5 3,0 3,5 4,0 Pulp consistency (%) FIG. 9 Patent Application Publication Apr. 24, 2014 Sheet 6 of 11 US 2014/0110070 A1 35 S. pulp 1 30 25 Š O & & pulp 2 m20 'S & pulp 3 S. 5 s s & & & & pulp 4 O S s Šs &&.S $8.88. & & sS. O 40 80 120 16O 200 240 280 3 2O 36 reaction time, min FIG 10 90 80 pulp 5 70 O 60 $ pulp 6 m30 40 8 pulp 7 20 S & pulp 8 10 S. S. •S & S O - : Š: S S. O 40 80 120 16O 200 240 280 320 360 400 reaction time, min FIG 11 Patent Application Publication Apr. 24, 2014 Sheet 7 of 11 US 2014/0110070 A1 105 90 & pulp 9 ,75 & N pulp 10 m60 + pm . 8. Oulo 11 3O S $. S S X & & & pulp 12 15 is . O S X X& S. O 40 8O 12O 16O 20O 240 reaction time, min FIG. 12 pulp. 13 o120 N pulp 14 b80 - & pulp 15 2 O SS & S S pulp 16 8 & & & O 50 1 OO 150 200 250 3OO 350 reaction time, min FIG. 13 Patent Application Publication Apr. 24, 2014 Sheet 8 of 11 US 2014/0110070 A1 3 6 SSaxxx xxxx xxxx xxxx xxxxxaasaxxx xxxxx xxxx xxxx xxxx axxx xxx xxxx xxxx xxxx xxxxaasaxxx xxx xxxx xxxx xxxx xxxx xxxx xxxx xxxx xxxx xxxx xxxx xxxxx s S 3 O *formate &DMSO wŠRef Time, min 1.5 2 2.5 3 3.5 4. 4.5 5 mmol NaClO/g pulp Patent Application Publication Apr. 24, 2014 Sheet 9 of 11 US 2014/0110070 A1 3. n-propanol O.O.9 mM TEMPO nM NaBrpH 10 25C O2+n-propanol O.9 mM TEMPO 2 nM NaBrpH 10 250C Š2+n-propanol O.O9 | TEMPO 16 WNaB 1OO min reaction time, min propanol pH 1 O 5 FG 16 60 e - 50 C 50 -------- 35 C rea 25 C. 40 s2 T',y E 30 "Ya CS ^ 2 20- Yal R \ 2OO time, min FIG. 17 Patent Application Publication Apr. 24, 2014 Sheet 10 of 11 US 2014/0110070 A1 O.35 O.25 pulp consistency '6 FIG. 18 mmol TEMPO fig pulp FIG. 19 Patent Application Publication Apr. 24, 2014 Sheet 11 of 11 US 2014/0110070 A1 S. 2 $ HOC U mol/ O Š pH Time, min FIG. 20 O 6O 120 180 24O 3OO 360 Time, min US 2014/01 10070 A1 Apr. 24, 2014 METHOD FOR CATALYTIC OXDATION OF residues from the final cellulose product. Bromine com CELLULOSE AND METHOD FOR MAKINGA pounds also accumulate in process waters. Further, the use of CELLULOSE PRODUCT bromine in industrial scale is undesirable. Use of large amounts of sodium bromide cause corrosion problems in the FIELD OF THE INVENTION equipment. Bromine compounds are generally recognized as 0001. The invention relates to a method for catalytic oxi hazardous to health, for example bromate which is formed as dation of cellulose using a heterocyclic nitroxyl radical as a result of side reactions is a suspected carcinogen. catalyst. SUMMARY OF THE INVENTION BACKGROUND OF THE INVENTION 0008. It is a purpose of the invention to provide a method 0002 Cellulose is a renewable natural polymer that can be for effectively and selectively oxidizing the C-6 hydroxyl converted to many chemical derivatives. The derivatization groups of cellulose by avoiding the use of bromine com takes place mostly by chemical reactions of the hydroxyl pounds. groups in the B-D-glucopyranose units of the polymer. By 0009. One purpose of the invention is to avoid excessive chemical derivatization the properties of the cellulose can be use of chemicals and to provide an economical method for the altered in comparison to the original chemical form while oxidation of cellulose. retaining the polymeric structure. Reaction selectivity is 0010. It is a further object to provide a method for making important so that a derivative of desired chemical structure a cellulose product without the use of bromine compounds. could be obtained. 0011. In the catalytic oxidation of cellulose, the heterocy 0003. Heterocyclic nitroxyl compounds are known as clic nitroxyl radical is activated by a tertiary amine or chlorine catalysts that participate in the selective oxidation of C-6 dioxide. hydroxyl groups of cellulose molecules to aldehydes and 0012. By a proper choice of the activator the nitroxyl radi carboxylic adds, the corresponding oxoammonium salt being cal can be activated to the oxidized state without the use of known as the active direct oxidant in the reaction series. One bromide. of these chemical oxidation catalysts known for a longtime is 0013 Bromine compounds, especially sodium or potas “TEMPO, i.e. 2.2.6,6-tetramethylpiperidinyl-1-oxy free sium bromide, can be replaced by a tertiary amine compound radical. Thus, the oxidized forms of the nitroxyl radicals, which acts as cocatalyst and activates the heterocyclic N-ni N-oxoammoniumions, act as direct oxidants in the oxidation troxyl compound. In this role, the tertiary amine, which has of the target cellulose molecule, whereas a main oxidant is the general formula RR'R''N, alternates between oxidized used to bring oxygen to the reaction series and convert the form, quaternary ammonium cation RR'R"N" and reduced nitroxyl compound back to the oxidized form. form, the tertiary amine RR'R"N. Suitable tertiary amines are 0004. It is known to oxidize primary alcohols to aldehydes cyclic amines, such as hexamethylenetetramine, 1,4-diazabi and carboxylic acids through "TEMPO by using sodium cyclo[2.2.2]octane (DABCO) and quinuclidine. Hypochlo hypochlorite as the main oxidant (for example Anelli, P. L.; rite can be used as the main oxidant. The consumption of Biffi, C.; Montanari, F.; Quici, S.; J. Org. Chem. 1987, 52, tertiary amine is clearly lower compared with the consump 2559). To improve the yield in the oxidation of the alcohols to tion of bromides in conventional methods. carboxylic acids, a mixture of sodium hypochlorite and 0014. According to another embodiment, chlorine dioxide sodium chlorate was also used (Zhao, M. M.: Li, J.; Mano, E.; is used as the activator of the heterocyclic N-nitroxyl com Song, Z. J.; Tschaen, D. M.; Org. Synth. 2005, 81, 195). pound. The main oxidant is hypochlorite. It is preferable to 0005. It is also known procedure to catalytically oxidize perform the oxidation reaction in a two-step process where in cellulose in native cellulose fibers through "TEMPO by the first step, at a neutral or basic pH, chlorine dioxide is used using Sodium hypochlorite as main oxidant (oxygen source) as the activator and hypochlorite, for example sodium and sodium bromide as activator (Saito, T. et al.: Cellulose hypochlorite (NaClO), as the main oxidant. In a second step, Nanofibers Prepared by TEMPO-Mediated Oxidation of the pH is made acidic and the remaining aldehyde groups of Native Cellulose, Biomacromolecules 2007, 8, 2485-2491).
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