Sodium undecanoate

Larabee, C.E., Jr. and Sprague, E.D. (1986) Aggregation of sodium undecanoate and sodium 10-undecenoate in water at 37 °C vapor pressure osmometry. Journal of Colloid and Interface Science, 114 (1), 256-260. 

Anionic micellar systems were found to increase the rate of the acid catalyzed hydrolysis of acetylsalicylic acid (Nogami et al., 1962), methantheline bromide (Nogami and Awazu, 1962), n-butyl acetate, t-butyl acetate, ethyl p-aminobenzoate, and ethyl o-aminobenzoate (Sakurada et al., 1967), but decreased that of methyl benzoate slightly (Sakurada et al., 1967). The acid catalyzed hydrolysis of anionic amphi-philes also generally tend to be accelerated by micellization (Table 5). The rates of the acid catalyzed hydrolyses of sodium sulfoethyl do-decanoate, sodium undecanoate, and sodium sulfobutyl caprylate are significantly greater in micellar than in non-micellar solutions while that of sodium dodecyl sulfoacetate is unaffected by micelle formation (Meguro and Hikota, 1968). 

In view of the results obtained up to the present time, there seems little chance of succeeding with a topochemical polymerisation of micellar systems. Micellar polymerisation is nevertheless a specific process which promises some useful applications. As an example, it makes possible a radical polymerisation of low reactivity monomers (e.g., sodium undecanoate). It can also produce high molecular weight polymers. 

The mesogenic units with methylenic spacers were prepared by reacting the sodium salt of either 4-methoxy-4 -hydroxybiphenyl or 4-phenylphenol with a bromoester in DMF at 82° C for at least 4 hours in the presence of tetrabutylammonium hydrogen sulfate (TBAH) as phase transfer catalyst. In this way, ethyl 4-(4-oxybi-phenyl)butyrate, ethyl 4-(4-methoxy-4 -oxybiphenyl)butyrate, ethyl 4-(4-oxybiphenyl)valerate, ethyl 4-(4-methoxy-4 -oxybiphenyl)-valerate, n-propyl 4-(4-oxybiphenyl)undecanoate and n-propyl 4-(4-methoxy-4 -oxybiphenyl)undecanoate were obtained. These esters were hydrolyzed with base and acidified to obtain the carboxylic acids. The corresponding potassium carboxylates were obtained by reaction with approximately stoichiometric amounts of potassium hydroxide. Experimental details of these syntheses were described elsewhere (27). 

A carboxylato surfmer III has been studied by Guillaume, Guillot and Pichot [22], for the purpose of preparing latexes carrying only carboxylic surface groups. Sodium acrylamido undecanoate (SAU) has been used, with a cmc at 25 °C of 5 x 10" mol/1. It has been utilized in copolymerization with styrene (S) and butylacrylate (B), initiated at 70 °C by an azocarboxy compound. The reactivity ratios with S and B were measured (S) or estimated (B) from the Q, e scheme the partition coefficient of SAU and of the comonomer between water and organic phases were also measured, so that a simulation of the copolymerization process was obtained which shows an S shape for the conversion of SAU, indicating that most of that surfmer is polymerized only at... 

Undecanoic acid may be obtained from the product of part (g) by use of the haloform reaction followed by treatment with acid. Upon the addition of iodine and sodium hydroxide (to form sodium hypoiodite, NaOT), methyl... 

In one instance, the corbien-carboxaldehyde was reduced with sodium borohydride to the corresponding alcohol, and 0-alkylated with co-undecanoic acid in THF, to produce compound 10 in moderate yield. 

This is ethyl 10-(/>-iodophenyl)undecanoate. It can be assayed by the flask-combustion method using 30 mg, 1 ml 0-02N thiosulphate = 0 001388 g or the alkali-fusion method given under Chiniofon Sodium. 1 ml 0 1 N thiosulphate == 0-006939 g. In the U.S.P. the iodine is assayed as under Injection of Iodised Oil using 300 mg. 

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