Synthesis of ethanethiol (ethyl mercaptan)

Preparation of ethanethiol (ethyl mercaptan)

Preparation of ethanethiol (ethyl mercaptan) from sodium ethyl sulfate and potassium hydrogen sulfide

Preparation of ethanethiol (ethyl mercaptan) from sodium ethyl sulfate and potassium hydrogen sulfide

Preparation of ethanethiol (ethyl mercaptan) from sodium ethyl sulfate and potassium hydrogen sulfide

Two parts by volume of 99% alcohol are added to a mixture of 1 part by volume of sulfuric acid (d=1.84) and 1 part of 20 % fuming sulfuric acid, the temperature being kept below 70° C. The mixture is allowed to cool overnight, then diluted with ice-cold water, and poured with stirring on to a mixture of ice and a solution containing 8 parts by weight of sodium carbonate crystals. Additional sodium carbonate is added to adjust the pH to neutral, and the neutral solution is concentrated until a crust of salt forms on the surface. On cooling, separated sodium sulfate is filtered and the filtrate containing sodium ethyl sulfate, measuring about 3 volumes, is mixed with a solution of potassium sulfide, prepared by saturating with hydrogen sulfide a solution of 1.6 parts by weight of potassium hydroxide in 3 parts by volume of water. The reaction mixture is gradually heated, and the ethanethiol distilled over. It is freed from ethanethiol by treatment with concentrated sodium hydroxide solution, in which ethanethiol dissolves. Any undissolved oil is separated, after which the ethanethiol is reprecipitated by addition of acid.

Preparation of ethanethiol (ethyl mercaptan) from ethyl chloride and potassium hydrogen sulfide

Preparation of ethanethiol (ethyl mercaptan) from ethyl chloride and potassium hydrogen sulfide

Preparation of ethanethiol (ethyl mercaptan) from ethyl chloride and potassium hydrogen sulfide

A solution of potassium (or sodium) hydrogen sulfide is treated with ethyl chloride in a autoclave, fitted with a stirrer and connected to a condenser. Slightly excess than one mole of ethyl chloride is used, some ethyl alcohol also being added to facilitate reaction. The reaction mixture is gently warmed, with continuous stirring, to 50-60° C, and maintained at this temperature until the reaction to be completed (titration of test portions with acid, using methyl orange as indicator). The ethanethiol, which is mixed with alcohol and some diethyl sulfide, is distilled over, converted into its sodium salt, after which the alcohol and diethyl sulfide are removed by a second distillation, and reprecipitated by the addition of inorganic acid. Ethanethiol boils at 36° C insoluble in water, soluble in most organic solvents.

Organic medical chemicals, by M. Barrowliff, 32-33, 1921

IUPAC Name

ethanethiol

InChI

InChI=1S/C2H6S/c1-2-3/h3H,2H2,1H3

InChI Key

DNJIEGIFACGWOD-UHFFFAOYSA-N

Canonical SMILES

CCS

MeSH Synonyms

ethanethiol, ethanethiol silver salt (+2), ethanethiol sodium salt, ethyl mercaptan

Depositor-Supplied Synonyms

Ethanethiol, ETHYL MERCAPTAN, Mercaptoethane, Ethyl hydrosulfide, Thioethanol, 75-08-1, 1-Mercaptoethane, Ethyl sulfhydrate, Ethyl thioalcohol, Thioethyl alcohol, Aethanethiol, Aethylmercaptan, Ethaanthiol, Ethylmercaptaan, Ethylmerkaptan, Etilmercaptano, Etantiolo, ethylmercaptan, ethyl-mercaptan, Mercaptan C2, LPG ethyl mercaptan 1010, Etantiolo [Italian], Ethaanthiol [Dutch], Aethanethiol [German], Ethylmerkaptan [Czech], Ethylmercaptaan [Dutch], Aethylmercaptan [German], Etilmercaptano [Italian], NSC 93877, HSDB 814, DNJIEGIFACGWOD-UHFFFAOYSA-N, EINECS 200-837-3, UN2363, AI3-26618, ethanothiol, ethanthiol, ethane thiol, Thioethyl Group, 1-Ethylthiol, EtSH, Ethanethiol solution, QuadraPure® DET, QuadraPure(TM) DET, AC1L1MBI, 32812-83-2, ACMC-1BH8A, C2H5SH, WLN: SH2, E3708_ALDRICH, Ethanethiol (ethyl mercaptan), KSC224Q0L, UNII-M439R54A1D, W527505_ALDRICH, 506818_SUPELCO, 668575_ALDRICH, CTK1C4805, MolPort-001-608-909, LTBB001434, M439R54A1D, 811-51-8 (hydrochloride salt), NSC93877, ANW-13589, NSC-93877, QuadraPure(TM) Bis(ethyl mercaptan), QuadraPure® Bis(ethyl mercaptan), 811-50-7 (mercury(+2) salt), AKOS000120313, RL04863, RTR-024200, UN 2363, AN-23836, LS-65753, SC-88053, DB-004032, TR-024200, E0036, FT-0625727, Ethyl mercaptan [UN2363] [Flammable liquid], InChI=1/C2H6S/c1-2-3/h3H,2H2,1H, Ethyl mercaptan [UN2363] [Flammable liquid], 146587-EP2377849A2, I09-1618, XL1

Removed Synonyms

Beta-Mercaptoethanol, Ethanethiol, sodium salt, CID6343, 2,3-DIHYDROXY-1,4-DITHIOBUTANE, S-[(1-Oxyl-2,2,5,5-Tetramethyl-2,5-Dihydro-1h-Pyrrol-3-Yl)methyl] Methanesulfonothioate, 6982-46-3, BME, DTT, MTN, SCC

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