Synthesis and Study of 4, 4-12-12 Alkyl Phenol Polyoxyethylene Sulfonate Gemini Surfactant

Background: Gemini surfactants have good prospect of application development in various fields for their superior performance in foaming, wettability, and emulsification with lower critical micelle concentration (CMC) than conventional mono-surfactants. Objective: The purpose of this study was to synthesize an ionic sulfonate Gemini surfactant, which is mainly used as an oil flooding agent, to improve oil recovery and reduce oil production cost. Methods: With 4-dodecyl phenol, diethylene glycol and triethylene glycol as the raw materials to synthesize two sulfonate Gemini surfactants. The single factor experiment combined with Box-Behnken center composite experimental design, the optimum reaction conditions were determined. The optimal reaction condition of sulfonation was determined by orthogonal test. The product structure was characterized by nuclear magnetic resonance and infrared. Results: The mass fraction of sodium hydroxide ω(NaOH), temperature and the quality ratio of hexadecyl trimethyl ammonium bromide to dodecyl phenol were 18%, 93.5°C and 14.2%, respectively. Under the condition of ice bath, the molar ratio of chlorosulfonic acid to 4, 4- 12-12 alkyl phenol polyoxyethylene ether was 2.02:1 and reaction for 5h. The critical micelle concentration was determined to be 2×10-4, 1.05×10-4, respectively. Conclusion: Two sulfonate Gemini surfactants, namely 5, 5-dilauryl alkyl-2,2'-(diethylene glycol oxygen base) sodium diphenyl sulfonate and 5,5-dilauryl alkyl-2,2'-(triethylene glycol oxygen base) sodium diphenyl sulfonate (recorded as III and IV, respectively) were synthesized. The synthesized surfactants have excellent emulsification ability.

The enol content of simple carbonyl compounds: an approach based upon pKa estimation

Rate constants for oxygen-base-catalyzed enolization of di- and tricarbonyl compounds can be correlated by a Marcus equation, with hydroxide requiring a slightly different curve from other oxyanions. Data for monocarbonyl compounds fall on a slightly different, but similar, set of curves. The equilibrium constants for enolization for a set of monocarbonyl compounds were derived from recent work in this laboratory. These correlations permit estimation of pKaKeto for a number of other monocarbonyl compounds from kinetics data in the literature. Elaboration of methods previously developed permits estimation of pKaEnol. From the values of pKaEnol and pKaKeto, pKEnol can be derived. It is pointed out that pKaKeto for acetone and acetophenone can be determined from the kinetics of the reaction with hypochlorite in base; the values so derived are in good agreement with those used in this work. pKEnol values are reported for: 1,3-dichloroacetone, 2.0; 1,1-dichloroacetone, 4.9; ethyl pyruvate, 4.2; bromoacetone, 3.5; chloroacetone, 3.7; l-phenyl-2-propanone, 4.5 (CH2); 7.2 (CH3); p-nitroacetophenone, 7.1; ethyl levulinate, 5.6; methoxyacetone, 6.9 (CH2); 7.6 (CH3); benzalacetone, 7.6; p-methoxyacetophenone, 7.8; 3-methyl-2-butanone, 8.0 (CH); 2,4-dimethyl-3-pentanone, 9.4.