Org. Synth. 1930, 10, 96
DOI: 10.15227/orgsyn.010.0096
SODIUM 2-BROMOETHANESULFONATE
[Ethanesulfonic acid, 2-bromo-, sodium salt]
Submitted by C. S. Marvel and M. S. Sparberg.
Checked by Frank C. Whitmore and D. J. Loder.
1. Procedure
In a 5-l. round-bottomed flask, fitted with a reflux condenser, a mechanical stirrer, and a separatory funnel, are placed 615 g. (3.3 moles) of ethylene dibromide (Note 1), 1250 cc. of 95 per cent alcohol, and 450 cc. of water (Note 2). The stirrer is started and the mixture heated to boiling. To the well-stirred boiling mixture a solution of 125 g. (1 mole) of anhydrous sodium sulfite in 450 cc. of water is added through the separatory funnel over a period of about two hours. The solution is boiled under a reflux condenser for two hours after all the sulfite solution has been added. The condenser is then set for distillation, and the alcohol and the ethylene bromide are distilled (Note 3). The remaining water solution is poured into a large evaporating dish and evaporated to dryness on the water bath. The sodium 2-bromoethanesulfonate is extracted from the sodium bromide and unchanged sodium sulfite with 2 l. of boiling 95 per cent alcohol. On cooling the solution, most of the salt crystallizes; the mother liquor is used for a second extraction of the residue. The yield is 165–190 g. (78–90 per cent of the theoretical amount). The product (Note 4) may be further purified by recrystallizing from alcohol and drying in an oven at 110° (Note 5). The recovery on recrystallization is 75–80 per cent.
2. Notes
1.
The large excess of
ethylene dibromide is necessary to reduce the formation of the
disulfonic acid.
2.
The concentration of the alcohol seems to be important; poorer yields were obtained when it was changed in either direction.
3.
By diluting the alcoholic distillate from the reaction mixture with 10 l. of water, it is possible to recover about
400 g. of ethylene dibromide.
4.
This product may contain as much as
2 to 5 per cent of sodium bromide, but it is pure enough for the preparation of
taurine (p. 563). A very pure product can be obtained by a second crystallization from alcohol.
5.
The salt is slightly hygroscopic.
3. Discussion
The directions given in the procedure are based on those of Kohler.
1 Sodium 2-bromoethanesulfonate has also been prepared by treating
ethylene oxide with
sodium bisulfite and converting the
isethionic acid thus obtained to the bromo acid with
hydrobromic acid.
2
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
disulfonic acid
alcohol (64-17-5)
sodium sulfite (7757-83-7)
HYDROBROMIC ACID (10035-10-6)
sodium bromide (7647-15-6)
sodium bisulfite (7631-90-5)
Ethylene oxide (75-21-8)
ethylene dibromide,
ethylene bromide (106-93-4)
Taurine (107-35-7)
Sodium 2-bromoethanesulfonate,
Ethanesulfonic acid, 2-bromo-, sodium salt (4263-52-9)
isethionic acid (107-36-8)
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