Production of aminoalkylsulfonic acids

Details Production of aminoalkylsulfonic acids Production of aminoalkylsulfonic acids

1986-02-03

1987-04-14

Siegel, Alan

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C14302

Patent

active

046577041

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field:
This invention relates to a process for preparing aminoalkylsulfonic acids at a low production cost and with a high yield.
2. Background Art:
Aminoalkylsulfonic acids are useful compounds as intermediate raw materials for pharmaceutical products, surfactants, pH buffers, etc. Among such aminoalkylsulfonic acids, 2-aminoethylsulfonic acid is an extremely useful compound because it per se has such pharmacological effects as detoxification effect, fatigue-relieving effect and nourishing and tonifying effect.
The following processes have heretofore been known as preparation processes of aminoalkylsulfonic acids:
(1) To react sulfur dioxide gas and water with ethyleneimine (Japanese Patent Publication Nos. 23007/1965 and 16807/1972);
(2) To react ethylene chloride with sodium sulfite to form sodium 2-chloroethylsulfonate, with which a liquid mixture of anhydrous ammonia or a 27% aqueous solution of ammonia and ammonium carbonate, or an alkylamine is heated under elevated pressure to react them together [Ind. Eng. Chem., 39, 906 (1947)];
(3) To react a hydroxylalkylsulfonic acid with ammonia or an alkylamine under elevated pressure (U.S. Pat. Nos. 1,932,907 and 1,999,614);
(4) To oxidize 2,2-disubstituted thiazolidine with hydrogen peroxide (Japanese Patent Laid-open No. 26654/1982);
(5) To react 2-aminoethanol sulfate with sodium sulfite (J. Chem. Soc., 1943, 4); and
(6) To react a hydrogen halide salt of a 2-halogeno-ethylamine with a sulfite [(Ind. Eng. Chem., 39, 906 (1947); and J. Am. Chem. Soc., 58, 191 (1936)].
These conventional processes are however accompanied by such serious problems as will be mentioned below. The process (1) involves some serious hazards from the viewpoint of safety since it uses, as raw materials, ethyleneimine which has extremely strong toxicity and carcinogenicity and is expensive and sulfur dioxide which induces chest pain, cough and dyspnea when it is inhaled. Moreover, the reaction is an extremely exothermic and thus involves a great problem from the viewpoint of reaction control upon effecting the reaction on an industrial scale. In the process (2) or (3), it is necessary to conduct the reaction by heating ammonia or an alkylamine under elevated pressure. The processes (2) and (3) are each accompanied with another drawback that its industrial application requies extremely expensive production facilities. On the other hand, the process (4) requires to use hydrogen peroxide which is very dangerous in handling it and, accordingly, involves a safety problem. Besides, the operation becomes irksome because ketones, which are by-produced, must be recovered and recycled. In the case of each of the processes (5) and (6), there is a merit that the raw materials are easy to handle because they are safe compounds. However, they were still accompanied by such problems as will be referred to below. In the process (5), the reaction between the sulfate and sodium sulfite is extremely slow and requires heating over a long period of time. Moreover, the sulfate per se is a compound liable to hydrolysis. Due to the hydrolysis of the sulfate upon undergoing a reaction with sodium sulfite, monoethanolamine is unavoidably by-produced. In addition to an extremely low yield, the process (5) is accompanied by a variety of problems such as the separation and recovery of the thus by-produced monoethanolamine. Although the process (6) can achieve a relatively high yield, for example, 80% in the case of 2-bromoethylamine, the yield is still insufficient to employ the process (6) on an industrial scale. In order to make the yield still higher, it is indispensable to use the sulfite to large excess, thereby raising another problem as to the separation and recovery of the sulfite. In the case of 2-chloroethylamine, the process (6) can provide a yield still lower than the process (5) and cannot thus be considered as an industrial preparation process.
As has been described in detail, none of the conventional processes was considered to be a satisfactory process, because they ar

REFERENCES:
Gilbert, "Sulfonation and Related Reactions", (1965), p. 137.
Gilbert, "Sulfonation and Related Factors", (1965), pp. 148 and 149.
J. Chem. Soc., (1936), pp. 191 and 192.

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