Method for preparing thionocarbamates and co-producing 2-mercaptoethanol or O-alkylthioethyl xanthogenate

A technology of alkylthioethyl yellow and alkylthioethyl, which is applied in mercaptan preparation, flotation, solid separation, etc., and can solve the problem of benzylmercaptan's unpleasant smell, etc.

Active Publication Date: 2018-09-25
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthetic routes include chlorohydrin route, ethylene oxide, hydrogen sulfide route, but the method of preparing thiourethane with alkyl xanthate, haloethanol, aliphatic amine etc. as raw materials and co-producing 2-mercaptoethanol at the same time has not been seen. to report
[0005] O-Alkylthioethanol is an important pharmaceutical intermediate, and there are few reports about its preparation method. Johanna prepared 2-benzylthioethanol (Johanna A , Michela B, Anthony L, et al, Inorg.Chim.Acta.2004, 357:2687-2693), but there is an obvious shortcoming in this method that benzylthiol has an unpleasant smell

Method used

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  • Method for preparing thionocarbamates and co-producing 2-mercaptoethanol or O-alkylthioethyl xanthogenate
  • Method for preparing thionocarbamates and co-producing 2-mercaptoethanol or O-alkylthioethyl xanthogenate
  • Method for preparing thionocarbamates and co-producing 2-mercaptoethanol or O-alkylthioethyl xanthogenate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Embodiment 1: Preparation of O-isopropyl-S-hydroxyethyl xanthate

[0094] Add 8.13 parts of 2-chloroethanol with a purity of 99% into the reactor, add 18.9 parts of sodium isopropylxanthate with a purity of 83.54% in batches, stir while adding, then add 15 parts of distilled water, and heat up to the bottle The temperature is 60°C, after 5 hours of constant temperature reaction, cool to room temperature, and separate the liquid to obtain the oil phase O-isopropyl-S-hydroxyethyl xanthate. The analysis shows that O-isopropyl-S-hydroxyethyl xanthate The yield of acid ester was 88.3%. The product was characterized after being purified by column chromatography, the O-isopropyl-S-hydroxyethyl xanthate 1 H NMR as figure 1 As shown, the infrared spectrum is shown in Image 6 shown.

Embodiment 2

[0095] Embodiment 2: the preparation of O-isobutyl-S-hydroxyethyl xanthate

[0096] Add 8.13 parts of 2-chloroethanol with a purity of 99% into the reactor, add 19.32 parts of sodium isobutyl xanthate with a purity of 89.0% in batches, stir while adding, then add 15 parts of distilled water, and heat up to the bottle The temperature is 50°C, after 7 hours of constant temperature reaction, cool to room temperature, and separate the liquid to obtain the oil phase O-isobutyl-S-hydroxyethyl xanthate. The analysis shows that O-isobutyl-S-hydroxyethyl xanthate The yield of acid ester was 78.2%. The product was characterized after being purified by column chromatography, the O-isobutyl-S-hydroxyethyl xanthate 1 H NMR as figure 2 As shown, the infrared spectrum is shown in Figure 7 shown.

Embodiment 3

[0097] Embodiment 3: the preparation of O-isopropyl-N-ethyl thiocarbamate and 2-mercaptoethanol

[0098] Transfer the oil phase obtained in Example 1 to the reactor, then add 7 parts of ethylamine aqueous solution (65-70% content) into the constant pressure dropping funnel below 20°C, heat up to 70°C, react for 1 hour, and cool to At room temperature, wash the reaction liquid with 50 parts of 8.3% sodium hydroxide solution, and separate the liquids to obtain the oil phase: O-isopropyl-N-ethylthiocarbamate with a purity of 96.7%, based on O- The yield of isopropyl-S-hydroxyethylxanthate is 85.7%, the aqueous phase is sodium 2-hydroxyethanethiolate, the purity is 28.097%, based on O-isopropyl-S-hydroxyethylxanthogen The yield of the ester was 98.1%, and 50 parts of hydrochloric acid solution with a concentration of 10.95% was added to the water phase, and acidified at room temperature for 2 hours to obtain the 2-mercaptoethanol product with a yield of 92.34%. The product was ch...

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PUM

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Abstract

The invention belongs to field of mineral flotation collecting agent materials and in particular discloses a method for preparing thionocarbamates. The method comprises the following steps: carrying out esterification reaction on xanthogenate and 2-halogenated ethanol to obtain O-alkyl-S-hydroxyethyl xanthogenate; carrying out ammonolysis reaction on the O-alkyl-S-hydroxyethyl xanthogenate and fatty amine to obtain a mixture of the thionocarbamates and 2-mercaptoethanol; after carrying out alkali washing on the mixture of the thionocarbamates and the 2-mercaptoethanol, carrying out oil-water separation, wherein an oil phase is the thionocarbamates and a water phase is 2-hydroxyethanethiol salt; carrying out acid washing on the 2-hydroxyethanethiol salt to obtain 2-mercaptoethanol. The invention further provides O-alkylthioethyl xanthogenate which is prepared by enabling the 2-hydroxyethanethiol salt and alkyl halide to react to obtain 2-alkylthioethyl ethanol and enabling the 2-alkylthioethyl ethanol to react with carbon disulfide and alkali. According to the method provided by the invention, the yield of the prepared thionocarbamates, 2-mercaptoethanol and O-alkylthioethyl xanthogenate is high and the purity is high; a product is easy to separate and purity and co-production is realized; the cost is saved and the reaction efficiency is also improved; the method is green and environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of mineral collection, and in particular relates to a method for preparing thiourethane and co-producing 2-mercaptoethanol and a new O-alkylthioethyl xanthate collector. Background technique [0002] With the intensification of mining of mineral resources, the ore is becoming poorer, finer, and miscellaneous, and it is becoming more and more difficult to recycle useful minerals. Foam flotation is an important technology for mineral recovery. The physical and chemical properties of the mineral surface are changed by the addition of flotation agents, so that the hydrophobic mineral particles are enriched in the foam layer, and the hydrophilic mineral particles sink in the flotation process. The bottom of the machine, so as to achieve the separation of minerals. Flotation collector is the key technology for the efficient development and utilization of minerals. Since Keller first used xanthate as a flotation c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/04C07C319/02C07C323/12C07C329/14B03D1/012B03D101/02B03D103/04
CPCB03D1/012B03D2201/02B03D2203/04C07C319/02C07C329/14C07C329/16C07C333/04C07C323/12B03D1/008B03D2203/02
Inventor 钟宏黄小平王帅曹占芳
Owner CENT SOUTH UNIV
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