Abstract
Two different organosolv lignins (OSLs), that is, wheat straw and corn stover OSLs, were chemically and enzymatically functionalized. Functional groups were attached via the formation of stable ether bonds exploiting the reactivity of free phenolic OH groups along the lignin backbone. The functional groups introduced a range from compact charged and chargeable building blocks for the generation of surface-active lignins to oligomeric and polymeric species used in lignin block-copolymer productions. Combination of selected functions led to novel charged or chargeable polymeric lignin-based materials. Products could be realized with different degrees of technical loadings in terms of introduced functional groups.
Highlights
Abundant polyphenolic nonfossil-based, but renewable resources continue to have problems in benefitting from the growing trends of sustainability in general and substitution of non-sustainable “traditional” active ingredients in everyday consumer products in particular.[1−3] Especially lignin, despite enormous research efforts, still suffers from its intrinsic diversities and variabilities ranging from differences stemming from natural origins to issues emerging during industrially feasible isolations
The present study screened several synthetic and biosynthetic approaches based on utilization and manipulation of phenolic groups in organosolv lignin (OSL) in order to arrive at a portfolio of fully functionalized and characterized lignins with specific tailored solubility and hydrophobicity characteristics
The non-commercially available reactants used for the functionalization of OSLs were synthesized following and/or adopting literature protocols: (i) N,N,N-trimethyl-9-(oxiran-2-yl)nonan-1-aminium chloride starting from 10-undecenyl chloride;[33,34] (ii) 2-(oxiran-2yl)acetic acid starting from 3-butenoic acid;[33] and (iii) 9-(oxiran-2yl)nonanoic acid starting from 10-undecanoic acid.[33]
Summary
Abundant polyphenolic nonfossil-based, but renewable resources continue to have problems in benefitting from the growing trends of sustainability in general and substitution of non-sustainable “traditional” active ingredients in everyday consumer products in particular.[1−3] Especially lignin, despite enormous research efforts, still suffers from its intrinsic diversities and variabilities ranging from differences stemming from natural origins to issues emerging during industrially feasible isolations. Functionalization of novel industrially isolated lignins has the objective to change or improve their inherent characteristics and performances for making them suitable sustainable materials for specific downstream applications[1−3,19] or for dedicated downstream processing These modifications require control of lignin multifunctionality and are often run using simple and simplest chemistries[1,3,20−22] or sustainable enzymebased processes,[23−28] within which de facto only the laccasebased ones have yet managed to bridge the gap between laboratory or pilot-scale applications and real-life usage.[29]. The development of a rigorous protocol for general chemical modification of lignin can only be prescient from a thorough structural characterization and deep knowledge of the specific lignin chemistry
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