Enzymatic Synthesis of Lignin‐Based Concrete Dispersing Agents

Lignin is the most abundant aromatic biopolymer, functioning as an integral component of woody materials. In its unmodified form it shows limited water solubility and is relatively unreactive, so biotechnological lignin valorisation for high‐performance applications is greatly underexploited. Lignin can be obtained from the pulp and paper industry as a by‐product. To expand its application, a new synthesis route to new dispersing agents for use as concrete additives was developed. The route is based on lignin functionalisation by enzymatic transformation. Screening of lignin‐modifying systems resulted in functionalised lignin polymers with improved solubility in aqueous systems. Through grafting of sulfanilic acid or p‐aminobenzoic acid by fungal laccases, lignin became soluble in water at pH≤4 or pH≤7, respectively. Products were analysed and evaluated in miniaturised application tests in cement paste and mortar. Their dispersing properties match the performance criteria of commercially available lignosulfonates. The study provides examples of new perspectives for the use of lignin.

[1]  C. Crestini,et al.  On the structure of softwood kraft lignin , 2017 .

[2]  Bert M. Weckhuysen,et al.  Wege zur Verwertung von Lignin: Fortschritte in der Biotechnik, der Bioraffination und der Katalyse , 2016 .

[3]  John Ralph,et al.  Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis , 2016, Angewandte Chemie.

[4]  M. Richter,et al.  Novel materials through Nature's catalysts , 2015 .

[5]  C. Boeriu,et al.  Enzymatic modification of different lignins through oxidative coupling with hydrophilic compounds , 2015 .

[6]  L. Avérous,et al.  Chemical modification of lignins: Towards biobased polymers , 2014 .

[7]  M. Richter,et al.  Laccase versus Laccase-Like Multi-Copper Oxidase: A Comparative Study of Similar Enzymes with Diverse Substrate Spectra , 2013, PloS one.

[8]  I. Arends,et al.  Enzyme Initiated Radical Polymerizations , 2012 .

[9]  D. Rentsch,et al.  Reactions of a sulfonamide antimicrobial with model humic constituents: assessing pathways and stability of covalent bonding. , 2012, Environmental science & technology.

[10]  F. G. Calvo-Flores,et al.  Lignin as renewable raw material. , 2010, ChemSusChem.

[11]  G. Guebitz,et al.  Reactivity of long chain alkylamines to lignin moieties: implications on hydrophobicity of lignocellulose materials. , 2010, Journal of biotechnology.

[12]  A. Ragauskas,et al.  Synthetic Applications of Laccase in Green Chemistry , 2009 .

[13]  M. Brochier-Salon,et al.  Lignins as Macromonomers for Polyurethane Synthesis: A Comparative Study on Hydroxyl Group Determination , 2008 .

[14]  T. Kudanga,et al.  Laccase‐Mediated Wood Surface Functionalization , 2008 .

[15]  J. Pennington,et al.  N-15 NMR study of the immobilization of 2,4- and 2,6-dinitrotoluene in aerobic compost. , 2008, Environmental science & technology.

[16]  Sergio Riva,et al.  Laccases: blue enzymes for green chemistry. , 2006, Trends in biotechnology.

[17]  M. Lalk,et al.  Nuclear amination catalyzed by fungal laccases: reaction products of p-hydroquinones and primary aromatic amines. , 2005, The Journal of organic chemistry.

[18]  M. Lund,et al.  Enzymatic modification of kraft lignin through oxidative coupling with water-soluble phenols , 2001, Applied Microbiology and Biotechnology.

[19]  Mai,et al.  Chemo-enzymatic synthesis and characterization of graft copolymers from lignin and acrylic compounds. , 2000, Enzyme and microbial technology.

[20]  K. Thorn,et al.  Covalent Binding of Aniline to Humic Substances. 2. 15N NMR Studies of Nucleophilic Addition Reactions , 1996 .

[21]  D. Cocke,et al.  Chemical and physical effects of sodium lignosulfonate superplasticizer on the hydration of portland cement and solidification/stabilization consequences , 1995 .

[22]  Huai N. Cheng ENHANCING LACCASE ACTIVITY USING PRO-OXIDANTS AND PRO-DEGRADANTS CROSS REFERENCE TO RELATED APPLICATIONS , 2017 .

[23]  A. Hüttermann,et al.  Enzymatic co-polymerization of lignin with low-molecular mass compounds , 2004, Applied Microbiology and Biotechnology.