Related Experiment Video
Updated: Jun 30, 2026

Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst
Published on: June 8, 2016
Microemulsions with alkyldimethyl phosphine oxides and alkyldiethyl phosphine oxides
Renate Tessendorf1, Reinhard Strey, Cosima Stubenrauch
1University College Dublin, School of Chemical and Bioprocess Engineering, Centre for Synthesis and Chemical Biology (CSCB), SFI-Strategic Research Cluster in Solar Energy Conversion, Belfield, Dublin 4, Ireland.
Abstract:
Alkyldimethyl phosphine oxides (C n DMPO) as well as alkyldiethyl phosphine oxides (C n DEPO) with chain lengths of n = 10 (decyl), 12 (dodecyl), and 14 (tetradecyl) were synthesized and purified to study how the formation of microemulsions depends on the size of the headgroup and on the length of the alkyl chain. For that purpose, equal amounts of water and n-octane were taken and surfactant was added to solubilize the two solvents. The resulting fish-shaped phase diagrams for C 10DEPO, C 12DEPO, and C 14DEPO show that the longer the hydrophobic chain the more efficient the surfactant. Simultaneously, the extension of the lamellar phase (L alpha) shifts toward lower total mass fractions gamma of the surfactant, i.e., the tendency to form lyotropic liquid crystals (LCs) increases. These trends are well-known for nonionic alkyl ethylene oxides and can thus be interpreted accordingly. What is astonishing, however, is the significant influence the size of the short side chains has. Replacing two methyl groups by two ethyl groups leads to a drastic drop of the three-phase region toward lower temperatures, while the efficiency remains nearly unchanged. Moreover, the tendency to form LCs decreases significantly.
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
