A kind of preparation method of thiol compound

A technology for thiol compounds and organic compounds, which is applied in the field of thiol compound preparation, can solve the problems of complicated reaction process, poor catalyst selectivity, increased production cost, etc., and achieves high atomic economic utilization rate, high reaction conversion rate and selectivity. , The effect of easy filtration and recycling

Active Publication Date: 2016-08-17
SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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Problems solved by technology

But when the prior art adopts the second method to prepare mercaptan, its deficiency is: (1) the catalyst MgO, triethylamine etc. that adopt can not only catalyze the addition reaction of hydrogen sulfide and unsaturated organic compound, also can catalyze the product For the addition reaction of mercaptans and unsaturated organic compounds, in order to reduce the occurrence of side reactions, the ratio of hydrogen sulfide to unsaturated organic compound raw materials can only be increased, and because hydrogen sulfide is a gas, the reaction must be carried out under high pressure conditions. Improve the selectivity of the reaction, the reaction conditions are harsh
The high-pressure reaction process not only complicates the reaction process, but also increases the production cost; (2) organic base catalysts such as triethylamine are dissolved in the reaction system, and the separation is troublesome
[0004] The deficiencies of the prior art are mainly due to the poor selectivity of the catalyst under normal pressure conditions

Method used

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  • A kind of preparation method of thiol compound
  • A kind of preparation method of thiol compound
  • A kind of preparation method of thiol compound

Examples

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preparation example Construction

[0029] The preparation method of triethylamine starch quaternary ammonium base catalyst is as follows:

[0030] (1) Preparation of cationic etherifying agent:

[0031] Prepared with reference to the method reported by CHILDERS et al. (WO0010987) with slight changes, that is: add 90g of epichlorohydrin and 50mL of dichloromethane into a 250mL three-necked flask, cool to 10°C, and then add 49g of triethylamine (30min) And continue to react for about 5 hours, and check the reaction end point by gas phase; after the reaction of triethylamine is complete, add 30mL of water, stir for 30min, separate the water phase, continue to use dichloromethane to extract the water phase (50mL×3), and the remaining water phase The content of the product is determined by the Kjeldahl method, and the determination method refers to the literature "Wang Xiaojuan et al. Synthesis of dialdehyde starch-aniline Schiff base [J]. Fine Chemical Industry, 2012, 29, 601-605)"; other cationic etherification T...

Embodiment 1

[0041] In a 100mL four-neck flask, add 1g of triethylamine starch quaternary ammonium base catalyst, 30mL of ethanol, stir, feed nitrogen for 30min, then heat up to 60°C, then feed hydrogen sulfide gas (0.8L / h) into the reaction solution, And add dropwise acrylamide solution (5g diluted to 20mL); after a period of reaction, take samples for liquid phase, liquid quality, and gas analysis, until the liquid phase detection shows that the product content does not change within 1h, stop feeding hydrogen sulfide gas , nitrogen, cooled to room temperature, then the reaction solution was filtered, and the filtrate was distilled under reduced pressure to remove ethanol, the resulting solid was added to 50mL water, and 2mol.L -1 NaOH solution to adjust the pH of the solution to about 8. After stirring for 20-30min, the solution was extracted with ethyl acetate (3×20mL), and the remaining aqueous phase was adjusted to pH 3-4 with 2mol.L-1 hydrochloric acid, and then acetic acid was used t...

Embodiment 2

[0043] Add 1.6 g of methylbenzylamine starch catalyst (DS=0.35) and 20 mL of methanol into a 100 mL four-neck flask, stir, feed nitrogen gas for 30 min, and then cool down to 20° C., then feed hydrogen sulfide gas (0.4 L / h), and methyl vinyl ketone solution (5g diluted to 20mL) was added dropwise; after a period of reaction, samples were taken for liquid phase, liquid mass, and gas analysis until the liquid phase detection showed that the product content did not change within 1h. Finally, stop feeding hydrogen sulfide gas and nitrogen gas, then filter the reaction solution, carry out vacuum distillation on the filtrate, and collect products with a boiling point of 75-77°C. The results of liquid phase and liquid mass analysis show that the conversion rate of methyl vinyl ketone can reach 85%, the selectivity of reaction to form methyl mercaptoethyl ketone is 93%, and the yield is 75%.

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Abstract

The invention provides a preparation method of a thiol compound. According to the preparation method, gas-liquid reaction is carried out on sulfuretted hydrogen and an organic compound containing carbon-carbon double bonds in a solid base catalyst and a reaction solvent through Michael addition under the conditions that the temperature is 20-80 DEG C and the pressure is 0.10-0.12MPa, so as to prepare the thiol compound. The preparation method is mild in reaction condition; the adopted solid base catalyst is strong in alkalinity; the alkaline catalysis position has relatively strong steric hindrance, and the applicability is wide; the solid base catalyst is easy to filter and recover, and can be repeatedly used after being activated; the reaction conversion rate and the selectivity are high; the side reaction is reduced; and the atomic economic utilization rate of the reaction is high.

Description

technical field [0001] The invention belongs to the technical field of preparation of thiol compounds, in particular to a gas-liquid phase reaction of hydrogen sulfide and an organic compound containing a carbon-carbon double bond in a solid base catalyst and a reaction solvent through Michael addition under mild reaction conditions Process for the preparation of thiol compounds. Background technique [0002] Mercaptan is an important organic chemical raw material and organic chemical intermediate. It is widely used in the preparation of pesticide intermediates, pharmaceutical intermediates, optical resins, and chain transfer agents for free radical polymerization. It has a broad market. At present, mercaptan mainly has following 7 kinds of synthetic methods: (1) hydrogen sulfide is raw material method; (2) sodium hydrosulfide (potassium) alkylation method; (3) thiourea method; (4) sodium polysulfide method; ( 5) Sodium thiosulfate method; (6) Sulfate hydrolysis method; (7)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/04C07C323/60C07C323/22C07C323/52C07C323/65C07C323/03C07C321/10
Inventor 易先君程珍柳金章张建林姚刚马韵升
Owner SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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