Org. Synth. 1938, 18, 77
DOI: 10.15227/orgsyn.018.0077
TAURINE
[I]
Submitted by C. S. Marvel and C. F. Bailey.
Checked by Frank C. Whitmore and D. J. Loder.
1. Procedure
A solution of
110 g. (0.52 mole) of sodium 2-bromoethanesulfonate (p. 558) in about
2 l. (28 moles) of concentrated aqueous ammonia (sp. gr. 0.9) is allowed to stand for five to seven days
(Note 1) and is then evaporated to dryness. The last of the water is removed by heating on a
steam bath. The residue is dissolved in the minimum quantity of hot water (about 500 cc.) and, if necessary, treated with
5 g. of Norite. The colorless solution is concentrated to 65–70 cc., and
250 cc. of 95 per cent alcohol is added. In a short time
taurine mixed with some
sodium bromide separates. When crystallization is complete, the crude
taurine is collected on a filter and recrystallized by dissolving in 100 cc. of hot water and then adding to the solution enough
95 per cent ethyl alcohol (about 500 cc.) to give a final concentration of
80 per cent of alcohol. The
taurine which separates is usually free from bromides. However, occasional runs must be recrystallized four or five times to remove all the
sodium bromide. The yield of pure
taurine (Note 2) is
31–36 g. (
48–55 per cent of the theoretical amount).
2. Notes
1.
The reaction is about 25 per cent complete in five hours, 60 per cent complete in thirty hours, and 90 per cent complete in five days, as indicated by titration of the bromide ion.
2.
The purity of the
taurine prepared by this method was established by analysis.
[II]
Submitted by Frank Cortese
Checked by C. S. Marvel and C. L. Fleming.
1. Procedure
A solution of
615 g. (3 moles) of β-bromoethylamine hydrobromide (p. 91) and
416 g. (3.3 moles) of anhydrous u.s.p. sodium sulfite (Note 1) in 2.4 l. of water is concentrated on the steam bath to a minimum volume; thirty-six to forty-eight hours is required for this operation. After the mixture has cooled, the cold, moist cake is triturated with
1.5 l. of concentrated hydrochloric acid and collected on an asbestos mat in a
Büchner funnel. The precipitate is washed ten times with
150-cc. portions of concentrated hydrochloric acid. The filtrate is mixed well, decanted from precipitated salts if necessary, and concentrated over a free flame to a volume of 600 cc.
Two and four-tenths liters of 95 per cent ethyl alcohol is added, with vigorous stirring, to the hot mixture. After fifteen minutes, the product is collected on a filter, washed with 95 per cent ethyl alcohol until it is colorless, and air-dried. The crude material is purified by dissolving it in four times its weight of hot water, adding Norite, filtering, and adding to the hot filtrate five volumes of 95 per cent ethyl alcohol.
This product is practically pure taurine; it decomposes at 305–310° (Maquenne block). The yield is 255–275 g. (68–73 per cent of the theoretical amount).
2. Notes
1.
An equivalent quantity
(831 g.) of the more expensive crystalline sodium sulfite may be used.
3. Discussion
Taurine is generally prepared from ox bile
1 or the large muscle of the abalone.
2 It has been obtained from the oxidation of
cystamine3 and the decarboxylation of
cysteic acid;
4 from
ethyleneimine and
sulfur dioxide;
5 from
chloroethanesulfonic acid and
ammonia;
6 from
2-mercaptothiazoline by oxidation with
bromine water;
7 and from
acetaldehyde by a complex set of reactions involving sulfonation, formation of the aldehyde
ammonia and the imidosulfonic acid, and finally reduction.
8 Taurine is usually synthesized either from
bromoethanesulfonic acid and
ammonia9—Procedure I, or from
β-bromoethylamine hydrobromide and
sodium sulfite10
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
bromine water
ethyl alcohol (64-17-5)
acetaldehyde (75-07-0)
hydrochloric acid (7647-01-0)
ammonia (7664-41-7)
sodium sulfite (7757-83-7)
sulfur dioxide (7446-09-5)
sodium bromide (7647-15-6)
Norite (7782-42-5)
β-Bromoethylamine hydrobromide (2576-47-8)
Taurine (107-35-7)
ethyleneimine (9002-98-6)
Sodium 2-bromoethanesulfonate (4263-52-9)
cystamine
cysteic acid
chloroethanesulfonic acid
2-mercaptothiazoline
bromoethanesulfonic acid
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