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Part of the book series: Springer Series in Wood Science ((SSWOO))

Abstract

The term “hydrogenation” is often used indiscriminately and imprecisely to describe a number of processes involving reactions of molecular hydrogen. In characterizing the reactions of hydrogen with lignin, the pertinent terms may be defined as follows:

  • Hydrogenation: the addition of hydrogen (H2) to a multiple bond

  • Hydrogenolysis: a process in which cleavage of a carbon-carbon or carbon-hetero atom single bond is accomplished by reaction with hydrogen

Depending on the reaction conditions and catalyst, one or combinations of the foregoing processes may occur during the reaction of hydrogen with lignin.

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References

  • Adkins H (1954) Catalytic hydrogenation of esters to alcohols. In: Adams R (ed) Organic reactions, Vol. VIII, Wiley, New York, 9

    Google Scholar 

  • Augustine RL, Caputa AV (1965) Δ1(9)-Octalone-2 Org Syn 45:80–82

    Google Scholar 

  • Bhaskaran TA, Schuerch C (1969) A study of non-volatile hydrogenated maple wood lignin. TAPPI 52: 1948–1952

    CAS  Google Scholar 

  • Bhattacharya A, Schuerch C (1960) Lignin from the alkaline hydrogenation of sugar maple- wood III. Chromatographic separation of higher molecular weight fractions and a structural study. TAPPI 43: 840–844

    CAS  Google Scholar 

  • Brauns FE (1952) The chemistry of lignin. Academic Press, New York, 511–535

    Google Scholar 

  • Brauns FE, Brauns DA (1960) The chemistry of lignin: supplement volume. Academic Press, New York, 486–497

    Google Scholar 

  • Brewer C, Cooke LM, Hibbert H (1948) Studies on lignin and related compounds LXXXIV. The high pressure hydrogenation of maple wood. J Am Chem Soc 70: 57–59

    Article  PubMed  CAS  Google Scholar 

  • Brown SA, Neish AC (1959) Studies of lignin biosynthesis using isotopic carbon. VIII. Isolation of radioactive hydrogenolysis products of lignin. J Am Chem Soc 81: 2419 - 2424

    Article  CAS  Google Scholar 

  • Coscia CJ, Schubert WJ, Nord FF (1961) Investigations on lignins and lignification XXIV. The application of hydrogenation, hydrogenolysis, and vapor phase chromatography in the study of lignin and structure. J Org Chem 26: 5085–5091

    Article  CAS  Google Scholar 

  • Eachus SW, Dence CW (1975) Hydrogenation of lignin model compounds in the presence of a homogeneous catalyst. Holzforschung 29: 41–48

    Article  CAS  Google Scholar 

  • Faix O, Meier D (1987) Pyrolytic and hydrogenolytic studies on lignocelluloses, pulps, and lignins. Int Symp Wood Pulp Chem (Paris) 4th, Oral Presentations Imprimeric Jacques Poncet, 1: 253–257

    Google Scholar 

  • Fieser LF (1955) Experiments in organic chemistry. 3rd edn. D.C. Heath, Boston, 284–285

    Google Scholar 

  • Freudenberg K, Geiger H (1963) Pinoresinolid und andere Zwischenprodukte der Ligninbildung. Chem Ber 96: 1265–1270

    Article  CAS  Google Scholar 

  • Freudenberg K, Lautsch W, Piazolo G, Scheffer A (1941) Die Druckhydrierung des Lignins und Ligninhaltigen Ablaugen der Fichte. Chem Ber 74: 171–183

    Google Scholar 

  • Godard HP, McCarthy JL, Hibbert H (1941) Studies on lignin and related compounds LXII. High pressure hydrogenation of wood using copper chromite catalyst (Part 1). J Am Chem Soc 63: 3061–3065

    Article  CAS  Google Scholar 

  • Goheen DW (1971) Low molecular weight chemicals. In: Sarkanen KV, Ludwig CH (eds) Lignins. Occurrence, formation, structure and reactions. Wiley-Interscience, New York, 818–821

    Google Scholar 

  • Granath M, Schuerch C (1953) Preliminary separation of maple hydrol lignin. J Am Chem Soc 75: 707–709

    Article  CAS  Google Scholar 

  • Harris EE, D’Ianni J, Adkins H (1938) Reaction of hardwood lignin with hydrogen. J Am Chem Soc 60: 1467–1470

    Article  CAS  Google Scholar 

  • Hrutfiord BF (1971) Reduction and Hydrogenolysis. In: Sarkanen KV, Ludwig CH (eds) Lignins. Occurrence, formation, structure and reactions. Wiley-Interscience, New York, 487–509

    Google Scholar 

  • Hwang BH, Sakakibara A (1979) Hydrogenolysis of protolignin XV. Further isolation of some compounds from hardwood lignin. Mokuzai Gakkaishi 25: 647–652

    CAS  Google Scholar 

  • Hwang BH, Sakakibara A (1981) Hydrogenolysis of protolignin XVIII. Isolation of a new dimeric compound with a heterocycle involving α, β-diether. Holzforschung 35: 297–300

    CAS  Google Scholar 

  • Hwang BH, Sakakibara A, Miki K (1981) Hydrogenolysis of protolignin XVII. Isolation of three dimeric compounds with γ-O-4, ß-1, and ß-O-4 linkages from hardwood lignin. Holzforschung 35: 229–232

    Article  CAS  Google Scholar 

  • Kashima H, Osada T (1961) High pressure hydrogenolysis of lignin. J Soc Chem Ind Jpn 64: 916–919

    Article  CAS  Google Scholar 

  • Klemola A, Pepper JM (1969) 2-(2-Methoxy-4-n-propyIphenoxy)-propan-l-ol as a new spruce lignin hydrogenolysis product. Chem Commun 1048

    Google Scholar 

  • Lai YZ, Sarkanen KV (1971) Isolation and structural studies. In: Sarkanen KV, Ludwig CH (eds) Lignins. Occurrence, formation, structure and reactions. Wiley-Interscience, New York, 182–185

    Google Scholar 

  • Lautsch W (1941) Über die oxydative und hydrierende Destruktion des Holzes, des Lignins und der schwefelhaltige Ablaugen der Fichte. Cellul Chem 19: 69–87

    CAS  Google Scholar 

  • Lautsch W, Piazolo G (1943) Über die Hydrierung von Lignin und ligninhaltigen Stoffen mit Wasserstoff abgebenden Mitteln, insbesondere Alkoholen. Chem Ber 76: 486–498

    Google Scholar 

  • Lee YW, Pepper JM (1978) Lignin and related compounds VII. The isolation of a trimeric lignin compound by the hydrogenolysis of spruce wood. Tetrahedron Lett 5061–5062

    Google Scholar 

  • Lindblad A (1931) Preparation of oils from wood by hydrogenation. Ing Vetenskaps Akad Handl 107: 7–59

    Google Scholar 

  • Lundquist K, Miksche GE, Ericsson L, Berndtson L (1967) Über das Vorkommen von Glyceraldehyde-2-Aryl-Ätherstrukturen. Tetrahedron Lett: 4587–4591

    Google Scholar 

  • Matsukura M, Sakakibara A (1969) Hydrogenolysis of protolignin IV. Isolation of a dimeric material of “condensed type”. Mokuzai Gakkaishi 15: 297–302

    CAS  Google Scholar 

  • Matsukura M, Sakakibara A (1973a) Hydrogenolysis of protolignin V. Isolation of some dimeric compounds with carbon to carbon linkage. Mokuzai Gakkaishi 19: 131–135

    CAS  Google Scholar 

  • Matsukura M, Sakakibara A (1973b) Hydrogenolysis of protolignin VI. Isolation of a new trimeric compound with carbon to carbon linkage. Mokuzai Gakkaishi 19: 137–140

    CAS  Google Scholar 

  • Matsukura M, Sakakibara A (1973c) Hydrogenolysis of protolignin VIII. Isolation of a dimer with Cß—ß′ linkage and a biphenyl. Mokuzai Gakkaishi 19: 171–176

    CAS  Google Scholar 

  • McMillen DF, Malhotra R, Hum GP, Chang S-J (1985) Hydrogen-transfer-promoted bond scission initiated by coal fragments. J Energy Fuels 1: 193–198

    Article  Google Scholar 

  • Miki K, Renganathan V, Gold MH (1986) Mechanism of ß-aryl ether dimeric lignin model compound oxidation by lignin peroxidase of Phanerochaete chrysosporium. Biochemistry 25: 4790–4796

    Article  CAS  Google Scholar 

  • Nahum L (1965) Delignification of wood by hydrogenation in presence of dicobalt octacarbonyl. Ind Eng Chem 4: 71–74

    CAS  Google Scholar 

  • Ohta M, Sakakibara A (1969) Hydrogenolysis of protolignin III. Isolation of diguaiacylpropanol and chromatographic detection of some monomers. Mokuzai Gakkaishi 15: 247–250

    CAS  Google Scholar 

  • Olcay A (1963) Investigations on lignins and lignification XXIX. Hydrogenation products of spruce milled-wood lignin and of related model compounds. Holzforschung 17: 105–109

    Article  CAS  Google Scholar 

  • Parker PE, Coalson RL, Schuerch C (1966) The structure of dimers from the alkaline hydrogenation of lignin. Adv Chem Ser 59: 249–260

    Article  Google Scholar 

  • Parkhust HJ, Huibers DTA, Jones MWJ (1980) Production of phenol from lignin. Am Chem Soc Div Petrol Chem 25: 657–667

    Google Scholar 

  • Pavlic AA, Adkins H (1946) Preparation of a Raney nickel catalyst. J Am Chem Soc 68: 141

    Article  Google Scholar 

  • Pearl IA (1967) The chemistry of lignin. Marcel Dekker, New York, 210–220

    Google Scholar 

  • Pepper JM, Fleming RW ( 1978 Lignin and related compounds V. The hydrogenolysis of aspen wood lignin using rhodium-on-charcoal as catalyst. Can J Chem 56: 896–898

    Article  CAS  Google Scholar 

  • Pepper JM, Lee YM (1969) Lignin and related compounds I. A comparative study of catalysts for lignin hydrogenolysis. Can J Chem 47: 723–727

    Article  CAS  Google Scholar 

  • Pepper JM, Lee YM (1970) Lignin and related compounds II. Studies using ruthenium and Raney nickel as catalysts for lignin hydrogenolysis. Can J Chem 48: 477–479

    Article  CAS  Google Scholar 

  • Pepper JM, Steck W (1963) The effect of time and temperature on the hydrogenation of aspen lignin. Can J Chem 41: 2867–2875

    Article  CAS  Google Scholar 

  • Pepper JM, Supathna P (1978) Lignin and related compounds VII. A study of variables affecting the hydrogenolysis of spruce wood lignin using a rhodium-on-charcoal catalyst. Can J Chem 56: 899–902

    Article  CAS  Google Scholar 

  • Pepper JM, Rahman MD (1987) Lignin and related compounds. XI. Selected degradation of aspen poplar lignin by catalytic hydrogenolysis. Cellul Chem Technol 21: 233–239

    CAS  Google Scholar 

  • Rahman RD, Pepper JM (1988) Lignin and related compounds. XII. Catalytic degradation of proto and isolated aspen lignins under initially alkaline conditions. J Wood Chem Technol 8: 313–322

    Article  CAS  Google Scholar 

  • Sakakibara A, Araki T, Takahashi S (1957) Studies on pressure hydrogenolysis of lignin I. Heating of sulfite liquor with ethanol and sodium hydroxide under pressure. Bull Gov For Exp Stn 93: 113–117

    Google Scholar 

  • Sakakibara A, Oda K, Kubota M (1964) Hydrogenolysis of lignin V. Hydrogenolysis with the catalysts metal carbonyl and nickel carbonate. Bull Gov For Exp Stn 166: 159–171

    Google Scholar 

  • Sakakibara A, Sudo K, Kishi M, Aoyama M, Hwang (1980) Hydrogenolysis of protolignin XVI. Isolation of ß-O-4 and ß-ß type compounds. Mokuzai Gakkaishi 26: 628–632

    CAS  Google Scholar 

  • Sudo K, Hwang BH, Sakakibara A (1978) Isolation of a-O-y compound from hydrogenolysis products of lignin. Mokuzai Gakkaishi 24: 424–425

    CAS  Google Scholar 

  • Sudo K, Mullard DJ, Pepper JM (1981) Lignin and related compounds VIII. Lignin monomers and dimers from hydrogenolysis of aspen poplar wood using rhodium-on-charcoal catalyst. Can J Chem 59: 1028–1031

    Article  CAS  Google Scholar 

  • Sudo K, Pepper JM (1982) Lignin and related compounds. IX. The isolation of a dimer with a benzylisochroman structure from the hydrogenolysis products of aspen lignin. Can J Chem 60: 229–230

    Article  CAS  Google Scholar 

  • Sudo K, Sakakibara A (1973) Hydrogenolysis of protolignin VII. Isolation of D,L- syringaresinol, biphenyl, and diarylpropane from hardwood lignin. Mokuzai Gakkaishi 19: 165–169

    CAS  Google Scholar 

  • Sudo K, Sakakibara A (1974a) Hydrogenolysis of protolignin IX. Isolation of a trimeric compound linked with biphenyl- and Cß-C5-linkages. Mokuzai Gakkaishi 20: 327–330

    CAS  Google Scholar 

  • Sudo K, Sakakibara A (1974b) Hydrogenolysis of protolignin X. Isolation of two dimeric compounds with ß-aryl ether linkage. Mokuzai Gakkaishi 20: 331–335

    CAS  Google Scholar 

  • Sudo K, Sakakibara A (1974c) Hydrogenolysis of protolignin XI. Isolation of a dimer with Cß-C6 and a trimer with two Cß-C5 linkages. Mokuzai Gakkaishi 20: 396–401

    CAS  Google Scholar 

  • Sudo K, Sakakibara A (1975) Hydrogenolysis of protolignin XII. Isolation of dimeric and trimeric compounds with carbon to carbon linkages. Mokuzai Gakkaishi 21: 165–169

    Google Scholar 

  • Sudo K, Sakakibara A (1977) Hydrogenolysis of protolignin XIII. Isolation of trimeric biphenyl and lignin type compounds. Mokuzai Gakkaishi 23: 151–155

    CAS  Google Scholar 

  • Sudo K, Sakakibara A (1979) Hydrogenolysis of protolignin XIV. Isolation of a dimeric compound with α-O-γ linkage. Mokuzai Gakkaishi 25: 61–66

    CAS  Google Scholar 

  • Vuori A, Bredenberg JB-son (1984) Hydrogenolysis and hydrocracking of the carbon- oxygen bond 5. Hydrogenolysis of 4-propylguaiacol by sulfided CoO-MoO3/γ-Al2O3. Holzforschung 38: 253–262

    Article  CAS  Google Scholar 

  • Wada I, Ohta M, Sakakibara A (1969) Hydrogenolysis of protolignin II. Isolation of some hydrogenolysis products. Mokuzai Gakkaishi 15: 218–221

    CAS  Google Scholar 

  • Wada I, Sakakibara A (1969) Hydrogenolysis of protolignin I. Hydrogenolysis products under various reaction conditions. Mokuzai Gakkaishi 15: 214–218

    CAS  Google Scholar 

  • Yasuda S, Sakakibara A (1975) Hydrogenolysis of protolignin in compression wood I. Isolation of two dimers with Cß-C5 and Cß-C3 composed of p-hydroxyphenyl and guaiacyl nuclei and two p-hydroxyphenyl nuclei, respectively. Mokuzai Gakkaishi 21: 370–375

    CAS  Google Scholar 

  • Yasuda S, Sakakibara A (1976) Hydrogenolysis of protolignin in compression wood II. Isolation of two dimers with ß-aryl ether linkage and phenylisochroman structure. Mokuzai Gakkaishi 22: 606–612

    CAS  Google Scholar 

  • Yasuda S, Sakakibara A (1977a) Hydrogenolysis of protolignin in compression wood III. Isolation of four dimeric compounds with carbon to carbon linkage. Mokuzai Gakkaishi 23: 114–119

    CAS  Google Scholar 

  • Yasuda S, Sakakibara A (1977b) Hydrogenolysis of protolignin in compression wood IV. Isolation of a diphenyl ether and three dimeric compounds with carbon to carbon linkage. Mokuzai Gakkaishi 23: 383–387

    CAS  Google Scholar 

  • Yasuda T, Sakakibara A (1981) Hydrogenolysis of protolignin in compression wood V. Isolation of two trimeric compounds with y-lactone ring. Holzforschung 35: 183–187

    Article  CAS  Google Scholar 

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© 1992 Springer-Verlag Berlin Heidelberg

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Sakakibara, A. (1992). Hydrogenolysis. In: Lin, S.Y., Dence, C.W. (eds) Methods in Lignin Chemistry. Springer Series in Wood Science. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-74065-7_24

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  • DOI: https://doi.org/10.1007/978-3-642-74065-7_24

  • Publisher Name: Springer, Berlin, Heidelberg

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