Non-ionic surfactants from renewables – amphiphilic ligands in biphasic reactions

Abstract

Using the water-soluble N-methylglucamine and the non-polar β-myrcene in a biphasic telomerisation with the amphiphilic TPPMS ligand, new surfactants are obtained.

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

“…Transferring the telomerization of myrcene to a highly polar amine, such as the aforementioned N ‐methylglucamine (see section 2.2), results in potentially surface‐active products that are based entirely on a renewable feedstock. The large gap between the polarities of the polyol on one hand and the hydrocarbon on the other, requires the use of an aqueous, biphasic solvent system along with amphiphilic ligands . Another terpene that is a promising building block for valuable chemicals is β‐farnesene, which has recently become available on a larger scale.…”

Facile catalyst recycling by thermomorphic behaviour avoiding organic solvents: a reactive ionic liquid in the homogeneous Pd-catalysed telomerisation of the renewable β-myrcene

“…The former was previously used for the telomerisation of β-myrcene and the latter for the telomerisation of butadiene with dimcarb. 19,25 We assumed that the solubility of the ligand in dimcarb indicates the retention of the active catalyst, where the higher the solubility, the higher the retention. It was observed (Fig.…”

“…β-Myrcene as a renewable raw material 22,23 has been investigated in telomerisation. 24,25 Additionally, it has been used in several amination reactions, such as hydroaminomethylation 26 and hydroamination, [27][28][29] and in other homogeneously catalysed functionalization reactions such as hydroformylation. 30,31 However, its telomerisation was never carried out with dimethylamine and recycling of the homogeneous palladium/phosphorus catalyst was considered but never executed.…”

“…30,31 However, its telomerisation was never carried out with dimethylamine and recycling of the homogeneous palladium/phosphorus catalyst was considered but never executed. 24,25 By application of β-myrcene in the telomerisation with dimcarb, highly branched, tertiary dimethylamines with a third highly branched alkyl chain (C 20 ) at the nitrogen atom can be generated. Related molecules are industrially important for consumer products since surfactants can be formed via alkylation and N-oxidation.…”

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

“…The reaction has been also applied isomaltitol [174] or isosorbide [177] for which a strong solvent effect on the regioselectivity was observed, and to starch by Pinel and colleagues, showing how the issue of solvent and the presence of surfactants is important for such less soluble substrates [178][179][180]. It was also used with N-methyl glucamine and the renewable polyene -myrcene [181] (see section on N-containing compounds). This reaction has attracted significant interest due to its wide scope, efficiency and ability to undergo in clean and safe conditions [182][183][184][185][186].…”