Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters

Colloids Surf B Biointerfaces. 2019 Oct 1:182:110333. doi: 10.1016/j.colsurfb.2019.06.062. Epub 2019 Jun 28.

Abstract

A sodium alkyl disulfate mixture (SADM) synthesised from microbially produced 3-hydroxy fatty acids methyl esters (HFAMEs), showed 13-fold surface tension decrease when compared with the reference surfactant sodium dodecyl sulfate (SDS). Polyhydroxyalkanoates, accumulated by bacteria intracellularly when supplied with a mixture of fatty acids derived from hydrolysed rapeseed oil, were isolated, depolymerised and methylated to produce HFAMEs in very high yield (90%). A sequential chemical reduction and sulfation of the HFAMEs produced the sodium alkyl disulfates in high yields (>65%). SADM performs also 1.3-times better than dodecyl (1,3) disulfate, in surface tension tests. SADM shows also the formation of a specific critical micelle concentration (CMC) at a concentration 21-fold lower than SDS. The wettability of the SADM mixture is similar to SDS but the foaming volume of SADM is 1.5-fold higher. The foam is also more stable with its volume decreasing 3 times slower over time compared to SDS at their respective CMC values. Established sulfation technologies in chemical manufacturing could use the 3-hydroxy fatty acids methyl esters moiety (3-HFAME) given its origin from rapeseed oil and the extra OH residue on 3-position in the molecule, which affords the opportunity to produce disulfate surfactants with a proven superior performance to monosulphated surfactants. Thus, not only addressing environmental issues by avoiding threats of deforestation and monocultivation associated with palm oil use but also achieve a higher performance with lower use of surfactants.

Keywords: Anionic surfactants; Biobased; Biosurfactants; Hydrotropes; Pseudomonas; Specialty chemicals.

MeSH terms

  • Anions
  • Esters / chemistry
  • Esters / isolation & purification
  • Fatty Acids / chemistry*
  • Fatty Acids / isolation & purification
  • Green Chemistry Technology*
  • Humans
  • Methylation
  • Micelles
  • Polyhydroxyalkanoates / chemistry*
  • Polyhydroxyalkanoates / isolation & purification
  • Pseudomonas chlororaphis / chemistry*
  • Pseudomonas chlororaphis / metabolism
  • Rapeseed Oil / chemistry*
  • Sodium Dodecyl Sulfate / chemistry
  • Surface Tension
  • Surface-Active Agents / chemistry*
  • Surface-Active Agents / isolation & purification
  • Wettability

Substances

  • Anions
  • Esters
  • Fatty Acids
  • Micelles
  • Polyhydroxyalkanoates
  • Rapeseed Oil
  • Surface-Active Agents
  • Sodium Dodecyl Sulfate