Bacterial biodegradation of ethyoxylated surfactants

Agricultural, industrial and domestic use of surfactants leads to the entry of these compounds into terrestrial and aquatic ecosystems. Synthetic surfactants vary significantly in structure, but most consist of alkyl or alkylphenol groups attached to nonionic or anionic hydrophilic moieties. Continued use of these compounds is usually justified on the basis that they do not cause pollution problems because they undergo biodegradation by micro-organisms present in soils and surface waters. In accomplishing biodegradation, micro-organisms, predominantly bacteria, are exploiting these potentially useful resources of reduced carbon to derive energy and support growth in situations which are otherwise frequently oligotrophic. This paper reviews aspects of surfactant biodegradation, especially in relation to alcohol and alkylphenol ethoxylates used extensively as adjuvants for agrochemicals. In principle, bacteria can employ two strategies to gain access to the aliphatic chains in alcohol ethoxylate surfactants: separation of the hydrophobic chain from the hydrophile (central fission), or direct attack on the omega-terminal of the alkyl chain of the intact surfactant. Direct exocleavage of ethylene glycol units from the polyethylene glycol (PEG) chain also provides a third route to assimilable carbon. In pure cultures of known degraders or in mixed environmental samples, all three strategies are exploited, some even within the same organism. Central fission occurs predominantly at the alkyl-ether bond, but may also occur within the PEG chain itself, thus producing various glycol intermediates which accumulate in pure cultures but appear only transiently in mixed environmental samples. Against this background, the relative resistance of some alkylphenol ethoxylates to biodegradation can be assessed in mechanistic terms. The steric bulk of the aryl nucleus effectively eliminates the central fission pathway. Moreover, some alkyl phenol ethoxylates contain branched alkyl chains which restrict omega-/beta-oxidation. As a result, ethoxylate shortening appears to be the major course of biodegradation observed so far. Not surprisingly, these surfactants are observed to undergo extensive primary biodegradation (removal of surfactant properties) but relatively restricted ultimate degradation to carbon dioxide and normal cell components.