Class Agenda. Wood Chemistry. PSE 406/Chem E 470. Lignin Functional Groups Phenolic Hydroxyl. Lignin Functional Groups Methoxyl.
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1 Class Agenda PSE 40/Chem E 40 Lecture 11 Lignin Structure Functional groups» Methoxyl, phenolic hydroxyl, aliphatic hydroxyl, carbonyl Lignin structures Lignin carbohydrate complexes Lignin analytical procedures Lignin trivial facts Appendix PSE 40 Lecture 11 1 PSE 40 Lecture 11 Phenolic ydroxyl Methoxyl 15-0 free phenolic hydroxyl/0c: Softwood -15 free phenolic hydroxyl/0c: ardwood Reactivity» Units containing free phenolic hydroxyl groups much more susceptible to cleavage reactions - hydrolysis of α and β aryl ether linkages» Structures much more reactive towards modification reactions C R R Free Phenolic ydroxyl Etherified Phenolic ydroxyl ~0.5/C in softwoods ~1.5/C in hardwoods Generally resistant to acid and alkali S cleaves to form thiols, mercaptans (Kraft mill odor) Syringyl (both) R Guaiacyl (one) PSE 40 Lecture 11 PSE 40 Lecture
2 Aliphatic ydroxyl Carbonyl Groups Majority of aliphatic hydroxyl groups are primary: on γ carbon» Site relatively non-reactive» In some species, γ carbon oxygen linked through ester linkage to ρ-coumaric acid, etc Benzyl alcohols» Debated amount: 1-40/0 C in spruce» Play dominant role in delignification reactions PSE 40 Lecture 11 5 C C C Primary Alcoho Benzyl Alcohol ρ-coumaric Acid Total carbonyl groups 0/0C in spruce» 1/ Conjugated Structures Coniferaldehyde and α-keto structures Play important role in delignifcation reactions» 1/ Non-conjugated Structures Glyceraldehyde from β -1 coupling Larger amount in certain hardwoods and grasses due to esters. Conjugated Carbonyl Groups C Glyceraldehyde PSE 40 Lecture 11 Type Group C Carbonyl (α-keto group) Coniferaldehyde Non-Conjugated Carbonyl Groups R Lignin Structure Sakakibara Lignin-Carbohydrate Complex C 1 C C Carb oh ydrate 5 15 C C 14 C C 4 C C C 1 C 1 C C C C 1 C C C 1 C C 0 C All purified holocellulose materials contain a certain amount of lignin All purified lignin fractions contain a certain amount of monosaccharides LCCshave been enzymatically prepared from lignin and monosaccharide model compounds Significant work studying isolated LCCs» No definitive information on exact covalent bonding patterns» Generally accepted bonding patterns PSE 40 Lecture 11 PSE 40 Lecture 11
3 Lignin-Carbohydrate Complex Proposed Linkages Lignin-Carbohydrate Complex General Information C C C C C C C Xyl-Xyl-Xyl Xyl-Xyl-Xyl Benzyl Ester Linkage Benzyl Ether Linkage C C Man-Glu-Man Phenolic Glycosidic Linkage Mw of isolated LCCs 00 15,000 LCC linkage stability» Esters: alkali labile, acid labile» Ethers: selectively alkali labile, mildly acid labile» Glycosides: mildly alkali labile, acid labile Formation during pulping processes possible LCCs: residual lignin and bleaching» Removal of that last little bit of lignin» Enzyme assisted bleaching PSE 40 Lecture 11 PSE 40 Lecture 11 Lignin Structure Analytical Procedures Lignin Trivial Facts I All analysis require model compound studies! Linkages» Enzymatic dehydrogenation (test tube studies)» Degradation studies (see appendix)» NMR Functional groups» Wet Chemistry techniques» Spectroscopy Solubility» Native lignins: limited/no solubility in all solvents without modification Molecular Weight» Average Mw for softwood ~0,000, lower for hardwoods» Polydispersity ~.5-.0» Mw measured for lignosulfonates as high as 1,000,000 PSE 40 Lecture PSE 40 Lecture 11 1
4 Lignin Trivial Facts II Elemental Composition MWL» Spruce C..40 ( ) 0. C.. ( ) 0.» Beech C.50. ( ) 1.4 C..5 ( ) 1.4 UV Absorption» Strong adsorption at 05 and 0nm» Carbohydrates do not adsorb at 0nm Compression Wood (Softwoods)» igh % lignin (~40%), high % of ρ-hydroxy units (to 0%) Tension Wood (ardwoods)» Reduced lignin content Lecture 11 Appendix PSE 40 Lecture 11 1 PSE 40 Lecture Lignin Structure Elucidation Studies Nitrobenzene xidation Lignin Structure Elucidation Studies Permanganate xidation C C C C 1 C C Car bo hydrate 15 C 14 1 C C C 1 C C 15 C /Na N Vanillin (5% yield, softwoods) Syringaldehyde (hardwoods) 1 C C C C C C C C C C C Carbohydrate C C C 1 C C 1 1. Alklylation. KMn4 xidation. xi dation 4. Methylation C C C C C C CC C C C C PSE 40 Lecture PSE 40 Lecture
5 Lignin Structure Elucidation Studies Acidolysis Lignin Structure: Adler C 1 Car bohydr at e 15 C 14 Dioxane C C C 1 l C C 1 ibbert's Ketones C C PSE 40 Lecture 11 1 PSE 40 Lecture 11 1 Lignin Structure: Freudenberg Lignin Structure: Nimz PSE 40 Lecture 11 1 PSE 40 Lecture
6 Lignin Structure: Forss PSE 40 Lecture 11 1
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