The Chemistry of Wood and Kraft Pulping. 1
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1 The Chemistry of Wood and Kraft Pulping 1
2 Typical Composition of Wood Cellulose (41-53%) Hemicellulose (25-41%) Lignin (16-33%) Extractives (2-5%) Inorganics (<1%) Nitrogen compounds (traces) 2
3 Compositions of Several North American Pulpwood Species Species Cellulose, % Hemicelluloses, % Lignin, % Balsam Fir Eastern Hemlock Eastern White Cedar White Spruce Jack Pine Tamarack Typical Softwood Beech Trembling Aspen White Elm Red Maple White Birch Yellow Birch Typical Hardwood ragauskas@hotmail.com 3
4 Cellulose (1) ne sugar Linear Long Reducing and nonreducing ends Partly crystalline 4
5 Cellulose (2) H H H H 4 H H 1 H H H H H H -Cellulose n ragauskas@hotmail.com 5
6 Hemicelluloses More than one sugar Branched or substituted Short Reducing and nonreducing ends Generally not crystalline 6
7 Xylan (1) Primary hemicellulose in hardwoods Linear chain backbone of xylose units Substituents are 4--methylglucuronic acid, acetate groups and, in some, arabinose Substituents prevent crystallization, but may be removed during pulping and bleaching 7
8 Xylan (2) H 4 H H 3 C HC H 1 α β H H H HH 2 C 4 1α 3 H 1 H 4 H 1 β H 4-β D-Xylp-1 4-β D-Xylp-1 4-β D-Xylp-1 4-β D-Xylp β D-Xyp Me-α D-Glc pa 2 1 α-l-araf ragauskas@hotmail.com 8
9 Glucomannan (1) Chief hemicellulose component of softwoods Straight chain backbone of mannose units and a smaller number of glucose units More vulnerable than xylan to chemical degradation ragauskas@hotmail.com 9
10 Glucomannan (2) HH 2 C 4 H H R β R 1 HH 2 C 4 R R 1 R 4 HH 2 C R 1 β H HH 2 C H H 1 α 4-β D-Glcp-1 4-β D-Manp-1 4-β D-Manp-1 4-β D-Manp-1 6 2,3 1 α-d-galp Ac ragauskas@hotmail.com 10
11 Lignin Native lignin is a polymer of coniferyl alcohol, sinapyl alcohol, and p-coumaryl alcohol H R 2 β 6 5 γ α 1 4 H 2 3 R 1 Coniferyl alcohol/guaiacyl: R 1 =Me, R 2 =H Sinapyl alcohol/ syringyl: R 1 =R 2 =Me pcoumaryl alcohol: R 1 =R 2 =H A heterogeneous, branched and cross-linked polymer with phenylpropane units linked by C-C and C- bonds Cross-linked with polysaccharide chains ragauskas@hotmail.com 11
12 Beta--4 Linkage SW: 50% HW: 60% 12
13 Alpha--4 Linkage SW: 2-8% HW: 7% 13
14 5-5 Linkage 5-20% 14
15 4--5 Linkage SW: 4% HW: 7% 15
16 Beta-5, Beta-1 and Beta-Beta Linkages SW: 9-12% HW: 6% SW: 7% HW: 7% SW: 2% HW: 3% 16
17 Lignin Reactions During Kraft Pulping Fragmentation Alpha- and beta- aryl ether cleavage in free phenolic units Enol ether formation Alpha- and beta- aryl ether cleavage in etherified units C-C bond cleavage Condensation Bonding to carbohydrates ther reactions 17
18 Alpha-Aryl Ether Cleavage in Free Phenolic Unit 18
19 Beta-Aryl Ether Cleavage in Free Phenolic Units 19
20 Enol Ether Formation 20
21 Beta-Aryl Ether Cleavage in Etherified Units 21
22 C-C Bond Cleavage 22
23 Condensation: Competitive Addition of Nucleophiles to QM s ragauskas@hotmail.com 23
24 Condensation with Formaldehyde 24
25 Kraft Pulping Resistant Structures 25
26 Quinone Formation During Kraft Pulping 26
27 Lignin Carbohydrates Bonds 27
28 ther Reactions: Formation of Stilbenes and Enol Ethers 28
29 Residual Lignin Structure Phenolic hydroxyl groups Beta-aryl ethers C-C bonds Condensation products Functional group analysis Linkages to carbohydrates 29
30 Phenolic Hydroxyl Groups in Dissolved and Residual Lignins 3.2 Phenolic hydroxyl content (mmol/g) Kraft lignins Residual lignins Unbleached kappa number 10 Phenolic hydroxyl content of various kraft (from black liquor) and residual lignins versus unbleached kappa number Froass, Peter M.; Ragauskas, Arthur J.; Jiang, Jian E. NMR studies. Part 3. Analysis of lignins from modern kraft pulping technologies. Holzforschung (1998), 52(4), Froass, Peter M.; Ragauskas, Arthur J.; Jiang, Jian-er. Nuclear Magnetic Resonance Studies. 4. Analysis of Residual Lignin after Kraft Pulping. Industrial & Engineering Chemistry Research (1998), 37(8),
31 Beta-Aryl Ethers in Residual and Dissolved Lignins Cγ in β--4 (per aromatic unit) Residual lignins Kraft lignins Unbleached kappa number Content of Cγ in β--4 structures for various kraft (from black liquor) and residual lignin versus unbleached kappa number 31
32 Functional Groups in Lignin Wood/Pulp Froass, Peter M.; Ragauskas, Arthur J.; Jiang, Jian-er. Chemical structure of residual lignin from kraft pulp. Journal of Wood Chemistry and Technology (1996), 16(4),
33 Hexenuronic Acid Formation MeGlcA HexA H 3 C H H C 2 H H Kraft pulping H H H 2 C H + CH 3 - xylan Xylan ragauskas@hotmail.com 33
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