Sulfonic acid methyl esters

Methyl p-Nitrobenzenesulfonate, p-Nitrobenzene-sulfonic acid methyl ester. C,HTNO,S mol wt 217.20. C 38.71%, H 3.25%, N 6.45%, O 36.83%, S 14.76%. Reagent for selective methylation or cysteine residues in chemical modification of proteins Nakagawa, Bender, J. dm. Chem. Sac, 91, 1566(1969). Procedure Heinrikson. Biochem. Bio-phys. Res. Common. 41, 967 (1970). Prepd by the general method of reacting p-nitrobenzenesulfony] chloride with alcohols. See Morgan, Cretcher, J. Am. Chem Soc. 70, 375 (1948). 

Sulfonic acid methyl esters from sulfonic acids SO2OH SO2OGH3... 

Schmid et al. studied in detail the sulfonation reaction of fatty acid methyl esters with sulfur trioxide [37]. They measured the time dependency of the products formed during ester sulfonation. These measurements together with a mass balance confirmed the existence of an intermediate with two S03 groups in the molecule. To decide the way in which the intermediate is formed the measured time dependency of the products was compared with the complex kinetics of different mechanisms. Only the following two-step mechanism allowed a calculation of the measured data with a variation of the velocity constants in the kinetic differential equations. 

Fujiwara et al. used the CMC values of sodium and calcium salts to calculate the energetic parameters of the micellization [61]. The cohesive energy change in micelle formation of the a-sulfonated fatty acid methyl esters, calculated from the dependency of the CMC on the numbers of C atoms, is equivalent to that of typical ionic surfactants (Na ester sulfonates, 1.1 kT Ca ester sulfonates, 0.93 kT Na dodecyl sulfate, 1.1 kT). The degree of dissociation for the counterions bound to the micelle can be calculated from the dependency of the CMC on the concentration of the counterions. The values of the ester sulfonates are also in the same range as for other typical ionic surfactants (Na ester sulfonates, 0.61 Ca ester sulfonates, 0.70 Na dodecyl sulfate, 0.66). 

Fujiwara et al. studied the precipitation phase boundary diagrams of the sodium salts of a-sulfonated myristic and palmitic acid methyl esters in the presence of calcium ions [61]. The time dependency of the precipitation showed that the calcium salts have an extremely slow crystallization rate at room temperatures. This is the reason for the good hardness tolerance of the a-sulfonated fatty acid methyl esters. 

A soap-based powder can be produced in combination with ester sulfonates. Thirty-five percent of a sodium soap mixture (5% lauric acid, 5% myristic acid, 52% palmitic acid, 21% stearic acid, 12% oleic acid, and 5% linoleic acid) is mixed with 15% sodium a-sulfo palm oil fatty acid methyl ester, 3% lauric acid ethoxylate, 5% sodium silicate, 17% sodium carbonate, 20% Na2S04- 10H2O, and 5% water [79]. 

For an enzyme-containing detergent the enzyme is added to a detergent composition with esters and disalts of a-sulfo fatty acids. The detergent granular comprises 7 % sodium a-sulfo hardened palm oil fatty acid methyl ester, 5% disodium salt of a-sulfo hardened palm oil fatty acid, 10% sodium a-olefin (C14 18) sulfonate, 10% zeolite, 5% sodium carbonate, 5% water, and 55% sodium sulfate [82]. 

D. a-Sulfo fatty acid methyl esters (methyl ester sulfonates) 634... 

D. a-Sulfo Fatty Acid Methyl Esters (Methyl Ester Sulfonates)... 

The chemistry of fatty acid methyl ester (FAME) sulfonation is complicated and not yet fully elucidated, but it may be summarized as depicted in the following reaction scheme. The initial reaction between FAME and S03, although fast, is far from instantaneous. Two intermediate products are formed ... 

FAME may in the future become a possible organic feedstock to the sulfonated to fatty acid methyl ester sulfonate (FAMES). This feedstock is naturally renewable as it is produced from oils/fats or fatty acids. There are several possible process routes for the manufacture of FAME. 

Transesterification of fat triglycerides is the predominant method for manufacture of mixed fatty acid methyl esters, and direct esterification of fatty acids (FA) is practiced if very selective cuts of product, in general as an intermediate detergent range alcohol, are desired. Methyl cocoate is a mobile, oily liquid above 25 °C with a yellow tint and a characteristic fatty pungent odor. FAME sulfonation to FAMES is technically possible but been rarely applied up to now (1990) (Table 13). 

An exception to the above are fatty acid methyl esters, which, due to the reaction mechanism involving molecular rearrangements with excess S03, have to be sulfonated at a slightly higher mole ratio of S03 to methyl esters (namely, 1.15-1.20/L). Outside the reaction tubes, in the reactor jacket, cooling water is circulated to control the liquid-film temperature and removing the reaction heat. 

Fatty acid esters, 9 142 Fatty acid ester sulfonates, 23 528-529 Fatty acid ethoxylates, 24 149-150 Fatty acid methyl esters (FAME), 12 429 13 26t... 

Fujiwara, M., T. Okano, H. Amano, H. Asano, and K. Ohbu. 1997. Phase diagram of a-sulfonated palmitic acid methyl ester sodium salt-water systdrangmuirl 3 3345-3348. 

A mixture of 11.8 g of (+/-)-3a,6,7,7a-tetrahydro-4-methyl-2-oxo-ip-indaheptanoic acid methyl ester, 27 ml of ethylene glycol and 300 mg of p-toluene sulfonic acid mono-hydrate in 600 ml of benzene was refluxed with stirring for 18 hours using a Dean-Stark trap to separate the water formed in the reaction. The reaction mixture was cooled and added to 300 ml of cold 5% potassium bicarbonate. The aqueous layer extracted twice with 2 1 benzene-hexene. The combined organic fractions were washed 3 times with saturated aqueous NaCI, dried over sodium sulfate and evaporated to dryness... 

SYNS as-DLMETHYL SULPHATE METHANE-SULPHONTC ACID METHYL ESTER METHYL ESTER of METHANESULFONIC ACID METHYL ESTER of METHANESULPHONIC ACID METHYL METHANE-SULFONATE n METHYL METHANESULPHONATE METHYL METHANSULFONAT (GERMAN) METHYL METHANSULFONATE METHYL METHANSULPHON-ATE MMS NSC-50256... 

Fatty acid methyl esters play a major role in the oleochemical industry. Methyl esters have increasingly replaced fatty acids as starting materials for many oleo-chemicals. They are used as chemical intermediates for a number of oleochemicals, such as fatty alcohols, alkanolamides, a-sulfonated methyl esters, and many more. One other potential use of methyl esters is as a substitute for diesel oil (14). Methyl esters are clean burning with no sulfur dioxide emission. Although the heat of combustion is shghtly lower, there is no engine adjustment necessary and there is no loss in efficiency. 

Coco-Based Surfactants. The most important coconut oil-based surfactants are fatty alcohol sulfate, fatty alcohol ether sulfate, and fatty alcohol polyglycol ether. Two relatively new coco-based surfactants are fatty acid methyl ester sulfonate and alkyl polyglycoside, which is produced from fatty alcohol and starch or sugar, both renewable materials. 

Fatty acid methyl esters sulfonate may be considered a material with a great potential. Its superior sequestering effect on water hardness gives it an advantage over fatty alcohol sulfate. The sulfonation of fatty acid methyl ester is different from that of fatty alcohol. The reaction mechanism involves two steps (31). In the first reaction, the SO3 gas reacts quickly to form sulfoanhydride. In the second step (which takes 40-90 min), the sulfoanhydride becomes the sulfonating agent, reacting with the still-unreacted ester. 

The analysis of surface-active anions comprises the determination of simple aromatic sulfonic acids, hydrotropes (toluene, cumene, and xylene sulfonates), alkane- and alkene sulfonates, fatty alcohol ether sulfates, alkylbenzene sulfonates, and a-sulfofatty acid methyl esters. Many of these compounds are relevant predominantly in the detergent and cleansing industry. 

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