Dimethyl Thiodiglycolate synthesis
- Product Name:Dimethyl Thiodiglycolate
- CAS Number:16002-29-2
- Molecular formula:C6H10O4S
- Molecular Weight:178.21
96-34-4
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Yield: 93%
Reaction Conditions:
with sodium sulfide;sodium hydroxide;sodium dihydrogenphosphate;methyl tributylammonium chloride in water;toluene; pH=6.0 - 6.7 at 30 - 35; for 3 h;Product distribution / selectivity;
Steps:
1; 3
EXAMPLE 1In a 1 ltr. jacketed glass reactor, 17.9 g of sodium dihydrogenphosphate dihydrate were dissolved in 84.2 g of water (pH=3.9) and adjusted to pH=6.0 with 6.7 g of sodium hydroxide solution (32%). The buffer solution was warmed to 33° C. and admixed with 13.0 g of tributylmethylammonium chloride solution (75% in water) and 40.0 g of methyl chloroacetate. Simultaneously, 611.2 g of sodium sulphide solution (16% in water) and 182.1 g of methyl chloroacetate were metered in at 30-35° C. within 2 h. Subsequently, a further 19.3 g of sodium sulphide solution (16% in water) were metered in and the mixture was stirred at 33° C. for a further 1 h. The reaction solution was admixed with 130 ml of toluene, stirred vigorously and then the lower phase was removed. After the toluene had been distilled off at approx. 300 mbar, 226.6 g of a clear liquid comprising 93% dimethyl thiodiglycolate and 6% toluene were obtained. This corresponds to a yield of 93% of theory.; EXAMPLE 3In a 1 ltr. jacketed glass reactor, 17.9 g of sodium dihydrogenphosphate dihydrate were dissolved in 84.2 g of water (pH=3.9) and adjusted to pH=6.0 with 6.7 g of sodium hydroxide solution (32%). The buffer solution was warmed to 33° C. and admixed with 13.0 g of tributylmethylammonium chloride solution (75% in water) and 40.0 g of methyl chloroacetate. Simultaneously, 611.2 g of sodium sulphide solution (16% in water) and 182.1 g of methyl chloroacetate were metered in at 30-35° C. within 2 h. Subsequently, a further 19.3 g of sodium sulphide solution (16% in water) were metered in and the mixture was stirred at 33° C. for a further 1 h. The reaction solution was admixed with 130 ml of toluene and stirred vigorously. Subsequently, the lower phase was removed. After the toluene had been distilled off at approx. 300 mbar, 226.6 g of a clear liquid comprising 93% dimethyl thiodiglycolate and 6% toluene were obtained. This corresponds to a yield of 93% of theory.
References:
SALTIGO GMBH US2009/163736, 2009, A1 Location in patent:Page/Page column 2
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16002-29-2
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