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Published in: Cellulose 6/2011

01-12-2011

Chromophores in cellulosics, VI. First isolation and identification of residual chromophores from aged cotton linters

Authors: Thomas Rosenau, Antje Potthast, Karin Krainz, Yuko Yoneda, Thomas Dietz, Zenaida Peralta-Inga Shields, Alfred D. French

Published in: Cellulose | Issue 6/2011

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Abstract

In the present work, aged cotton linters have been analyzed for their chromophore content according to the CRI (“chromophore release & identification”) method. Despite the very low contents in the ppb range, nine chromophores have been unambiguously identified, which makes this account the first one on defined chromophoric structures isolated from cotton. A common feature of the chromophores are 2-hydroxy-[1,4]benzoquinone, 2-hydroxyacetophenone and 5,8-dihydroxynaphthoquinone moieties, which resemble chromophoric structures found in other cellulosic substrates, such as bleached pulps or fibers. The finding of these compounds in lignin-free cotton linters confirms the previous hypothesis that those chromophores are formed from (oxidized) carbohydrate structures rather than from lignin fragments.

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Literature
go back to reference Adorjan I, Potthast A, Rosenau T, Sixta H, Kosma P (2004) Discoloration of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell). Part 1: studies on model compounds and pulps. Cellulose 12(1):51–57 Adorjan I, Potthast A, Rosenau T, Sixta H, Kosma P (2004) Discoloration of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell). Part 1: studies on model compounds and pulps. Cellulose 12(1):51–57
go back to reference Bader RFW (1990) Atoms in molecules: a quantum theory (International series of monographs on chemistry 22). Oxford University Press, Oxford Bader RFW (1990) Atoms in molecules: a quantum theory (International series of monographs on chemistry 22). Oxford University Press, Oxford
go back to reference Brockmann H, Greve H, Waldmüller W (1971) Dimerisierung und cyclo-Trimerisierung von Naphthazarin und 5.6.7.8-Tetrahydro-chinizarin. Chem Ber 104:1436–1454CrossRef Brockmann H, Greve H, Waldmüller W (1971) Dimerisierung und cyclo-Trimerisierung von Naphthazarin und 5.6.7.8-Tetrahydro-chinizarin. Chem Ber 104:1436–1454CrossRef
go back to reference Crosby AH, Lutz RE (1956) A study of an oxidative-amination method for the synthesis of aminoquinones. J Am Chem Soc 78(6):1233–1235CrossRef Crosby AH, Lutz RE (1956) A study of an oxidative-amination method for the synthesis of aminoquinones. J Am Chem Soc 78(6):1233–1235CrossRef
go back to reference Gamble GR (2007) The effect of bale ageing on cotton fiber chemistry, processing performance, and yarn quality. J Cotton Sci 11:98–103 Gamble GR (2007) The effect of bale ageing on cotton fiber chemistry, processing performance, and yarn quality. J Cotton Sci 11:98–103
go back to reference Gamble GR (2008) Method for the prediction of the rate of +b color change in upland cotton (Gossypium hirsutum L.) as a function of storage temperatures. J Cotton Sci 12:171–177 Gamble GR (2008) Method for the prediction of the rate of +b color change in upland cotton (Gossypium hirsutum L.) as a function of storage temperatures. J Cotton Sci 12:171–177
go back to reference Jene PG, Pernin CG, Ibers JA (2001) Comparison of conventional and synchrotron X-ray structure determinations of the adduct 1, 2, 4, 5-tetrahydroxybenzene-2, 5-dihydroxy-1, 4-benzoquinone (1/1) and a conventional X-ray structure determination of 1, 2, 4, 5-tetrahydroxybenzene monohydrate. Acta Cryst C 57:730–734CrossRef Jene PG, Pernin CG, Ibers JA (2001) Comparison of conventional and synchrotron X-ray structure determinations of the adduct 1, 2, 4, 5-tetrahydroxybenzene-2, 5-dihydroxy-1, 4-benzoquinone (1/1) and a conventional X-ray structure determination of 1, 2, 4, 5-tetrahydroxybenzene monohydrate. Acta Cryst C 57:730–734CrossRef
go back to reference Krainz K, Potthast A, Suess U, Dietz T, Nimmerfroh N, Rosenau T (2009) Effects of selected key chromophores on cellulose integrity upon bleaching. Holzforschung 63(6):647–656CrossRef Krainz K, Potthast A, Suess U, Dietz T, Nimmerfroh N, Rosenau T (2009) Effects of selected key chromophores on cellulose integrity upon bleaching. Holzforschung 63(6):647–656CrossRef
go back to reference Lagercrantz C (1964) Formation of stable radicals in alkaline solution of some monosaccharides. Acta Chem Scand 18(5):1321–1324CrossRef Lagercrantz C (1964) Formation of stable radicals in alkaline solution of some monosaccharides. Acta Chem Scand 18(5):1321–1324CrossRef
go back to reference Ledl F, Schleicher E (1990) New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed Engl 29(6):565–706CrossRef Ledl F, Schleicher E (1990) New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed Engl 29(6):565–706CrossRef
go back to reference Manzocco L, Calligaris S, Mastrocola D, Nicoli MC, Lerici CR (2000) Review of non-enzymatic browning and antioxidant capacity in processed foods. Trends Food Sci Technol 11(9–10):340–346CrossRef Manzocco L, Calligaris S, Mastrocola D, Nicoli MC, Lerici CR (2000) Review of non-enzymatic browning and antioxidant capacity in processed foods. Trends Food Sci Technol 11(9–10):340–346CrossRef
go back to reference Martins SIFS, Jongen WMF, van Boekel MAJS (2000) A review of Maillard reaction in food and implications to kinetic modeling. Trends Food Sci Technol 11(9–10):364–373CrossRef Martins SIFS, Jongen WMF, van Boekel MAJS (2000) A review of Maillard reaction in food and implications to kinetic modeling. Trends Food Sci Technol 11(9–10):364–373CrossRef
go back to reference Olsson K, Pernemalm PA, Theander O (1978) Formation of aromatic compounds from carbohydrates. Part 7. Acta Chem Scand B 32:249–256CrossRef Olsson K, Pernemalm PA, Theander O (1978) Formation of aromatic compounds from carbohydrates. Part 7. Acta Chem Scand B 32:249–256CrossRef
go back to reference Popoff T, Theander O (1972) Formation of aromatic compounds from carbohydrates. Part 1. Carbohydr Res 22:135–149CrossRef Popoff T, Theander O (1972) Formation of aromatic compounds from carbohydrates. Part 1. Carbohydr Res 22:135–149CrossRef
go back to reference Popoff T, Theander O (1976a) Formation of aromatic compounds from carbohydrates. Part 3. Acta Chem Scand B 30:397–402CrossRef Popoff T, Theander O (1976a) Formation of aromatic compounds from carbohydrates. Part 3. Acta Chem Scand B 30:397–402CrossRef
go back to reference Popoff T, Theander O (1976b) Formation of aromatic compounds from carbohydrates. Part 4. Acta Chem Scand B 30:705–710CrossRef Popoff T, Theander O (1976b) Formation of aromatic compounds from carbohydrates. Part 4. Acta Chem Scand B 30:705–710CrossRef
go back to reference Popoff T, Theander O, Westerlund E (1978) Formation of aromatic compounds from carbohydrates. Part 6. Acta Chem Scand B 32:1–7CrossRef Popoff T, Theander O, Westerlund E (1978) Formation of aromatic compounds from carbohydrates. Part 6. Acta Chem Scand B 32:1–7CrossRef
go back to reference Rao TVP, Venkateswarlu V (1965) Chemical eximination of Embelia ribes-VII. Synthesis of some new N-bis(anhydrobenzoquinones). Tetrahedron 21:389–390CrossRef Rao TVP, Venkateswarlu V (1965) Chemical eximination of Embelia ribes-VII. Synthesis of some new N-bis(anhydrobenzoquinones). Tetrahedron 21:389–390CrossRef
go back to reference Rokita S (ed) (2009) Ortho-Quinone methides in Wiley series on reactive intermediates in chemistry and biology, vol 1. Wiley, New York Rokita S (ed) (2009) Ortho-Quinone methides in Wiley series on reactive intermediates in chemistry and biology, vol 1. Wiley, New York
go back to reference Rosenau T, Potthast A, Milacher W, Adorjan I, Hofinger A, Kosma P (2004a) Discoloration of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell). Part 2: isolation and identification of chromophores. Cellulose 12(2):197–208 Rosenau T, Potthast A, Milacher W, Adorjan I, Hofinger A, Kosma P (2004a) Discoloration of cellulose solutions in N-methylmorpholine-N-oxide (Lyocell). Part 2: isolation and identification of chromophores. Cellulose 12(2):197–208
go back to reference Rosenau T, Potthast A, Milacher W, Hofinger A, Kosma P (2004b) Isolation and identification of residual chromophores in cellulosic materials. Polymer 45(19):6437–6443CrossRef Rosenau T, Potthast A, Milacher W, Hofinger A, Kosma P (2004b) Isolation and identification of residual chromophores in cellulosic materials. Polymer 45(19):6437–6443CrossRef
go back to reference Rosenau T, Adorjan I, Potthast A, Kosma P (2005) Isolation and identification of residual chromomophores in cellulosic materials. Macromol Symp 223(1):239–252CrossRef Rosenau T, Adorjan I, Potthast A, Kosma P (2005) Isolation and identification of residual chromomophores in cellulosic materials. Macromol Symp 223(1):239–252CrossRef
go back to reference Rosenau T, Potthast A, Kosma P, Suess H-U, Nimmerfroh N (2007) First isolation and identification of residual chromophores from aged bleached pulp samples. Holzforschung 61(6):656–661CrossRef Rosenau T, Potthast A, Kosma P, Suess H-U, Nimmerfroh N (2007) First isolation and identification of residual chromophores from aged bleached pulp samples. Holzforschung 61(6):656–661CrossRef
go back to reference Semmingsen D (1977) The crystal and molecular structure of 2, 5-Dihydroxy-1, 4-benzoquinone at −162 °C. Acta Chem Scand B 31:11–14CrossRef Semmingsen D (1977) The crystal and molecular structure of 2, 5-Dihydroxy-1, 4-benzoquinone at −162 °C. Acta Chem Scand B 31:11–14CrossRef
go back to reference Suess HU, Filho CL (2003) How to improve brightness stability of Eucalyptus Kraft pulp. Proceedings ABTCP 2003, 36° Congresso Internacional de Celulose e Papel, São Paulo, Brazil Suess HU, Filho CL (2003) How to improve brightness stability of Eucalyptus Kraft pulp. Proceedings ABTCP 2003, 36° Congresso Internacional de Celulose e Papel, São Paulo, Brazil
go back to reference Theander O, Nelson DA (1978) Aqueous, high-temperature transformation of carbohydrates relative to utilization of biomass. Adv Carbohydr Chem Biochem 46:273–326CrossRef Theander O, Nelson DA (1978) Aqueous, high-temperature transformation of carbohydrates relative to utilization of biomass. Adv Carbohydr Chem Biochem 46:273–326CrossRef
go back to reference Theander O, Westerlund E (1980) Formation of aromatic compounds from carbohydrates. Part 8. Acta Chem Scand B 34:701–705CrossRef Theander O, Westerlund E (1980) Formation of aromatic compounds from carbohydrates. Part 8. Acta Chem Scand B 34:701–705CrossRef
Metadata
Title
Chromophores in cellulosics, VI. First isolation and identification of residual chromophores from aged cotton linters
Authors
Thomas Rosenau
Antje Potthast
Karin Krainz
Yuko Yoneda
Thomas Dietz
Zenaida Peralta-Inga Shields
Alfred D. French
Publication date
01-12-2011
Publisher
Springer Netherlands
Published in
Cellulose / Issue 6/2011
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-011-9585-0

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