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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 bile1 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:

References and Notes
  1. Hammarsten, Z. physiol. Chem. 32, 456 (1901); Tauber, Beitr. chem. Physiol. Path. 4, 324 (1904).
  2. Schmidt and Watson, J. Biol. Chem. 33, 499 (1918).
  3. Schöberl, Z. physiol. Chem. 216, 193 (1933).
  4. Friedmann, Beitr. chem. Physiol. Path. 3, 1 (1903); White and Fishman, J. Biol. Chem. 116, 457 (1936).
  5. Gabriel, Ber. 21, 2667 (1888).
  6. Kolbe, Ann. 122, 42 (1862); Anschütz, ibid. 415, 97 (1918).
  7. Gabriel, Ber. 22, 1154 (1889).
  8. Auzies, Rev. gén. chim. 14, 278 (Chem. Zentr. 1911, II, 1433).
  9. Marvel, Bailey, and Sparberg, J. Am. Chem. Soc. 49, 1836 (1927).
  10. Reychler, Bull. soc. chim. Belg. 32, 247 (1923); Cortese, J. Am. Chem. Soc. 58, 191 (1936).

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