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Method for synthesizing propargyl alcohol

A synthesis method and technology of propargyl alcohol, which are applied in the fields of halogen elimination, hydrolysis preparation, organic chemistry, etc., can solve the problems of difficulty in dehydration, low cost and high energy consumption, and achieve the effect of reducing the difficulty of dehydration.

Active Publication Date: 2017-08-11
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of this method is that it uses cheap raw materials to synthesize propynyl alcohol, and the cost is low; the disadvantage is that a large amount of inorganic salt is produced by-product, and due to the use of low-concentration liquid caustic soda, the water content of propynyl alcohol is large, dehydration is difficult, and energy consumption is high.
In 1979, the Northeast Pharmaceutical General Factory first developed a method for synthesizing propynyl alcohol with 1,3-dichloropropene. The result was similar to that reported in WO2001074747. The dehydrochlorination uses 3% to 10% dilute alkali, and the yield is higher when concentrated alkali is used. Low, so that only low-concentration propargyl alcohol solution can be obtained, which increases the difficulty of dehydration

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. In a 2000ml reaction flask, add 900ml of water and 3.3mol of sodium carbonate, stir and mix evenly, then add 3mol of cis-1,3-dichloropropene (333g, content 99%), heat to 105°C, vigorously stir and reflux for 8 hours , with gas chromatography detection cis 1,3-dichloropropene residue <0.5% is the end of reflux, after the end of reflux, stand for layering, and the upper organic phase is sucked into the receiving bottle to obtain 248g 3-chloropropenol (water content is 5%), yield 85.0%;

[0026] pale yellow liquid, 1 HNMR (600MHz, DMSO-d6): δ6.26-6.27(m, 1H), δ5.97-6.0(m, 1H), δ4.93(t, 1H), δ4.11-4.16(m, 1H) , δ3.39 (t, 2H), δ2.5-2.51 (m, 1H), the following examples will not be repeated.

[0027] 2. Add the lower aqueous phase obtained in step 1 into a crystallization bottle, cool down to 5°C, and precipitate sodium bicarbonate. After the precipitation is complete, extract and concentrate the mother liquor, and concentrate to obtain 600ml of water. Put the remaining c...

Embodiment 2

[0032] 1. In a 2000ml reaction flask, add 900ml of water and 3.33mol of sodium carbonate, stir and mix evenly, then add 3mol of cis-1,3-dichloropropene (333g, content 99%), heat to 84°C, vigorously stir and reflux for 6 hours , the residual amount of cis-1,3-dichloropropene detected by gas chromatography <0.5% is the end of the reflux. After the reflux is over, let it stand for stratification, suck the red liquid in the upper layer into the receiving bottle, keep it warm and layered, and get 250g of 3-chloropropene in the upper layer Alcohol crude product (water content is 4%), yield 86.53%;

[0033]2. In a 2000ml reaction bottle, add 250g dimethyl sulfoxide, 0.72g hydroquinone and 3-chloropropenol obtained in step 1, heat to 70°C, and add 108g caustic soda in 20 times at the same time. The addition time is about 1 hour. After the addition, keep stirring for 2 hours. After the reaction is completed, cool down to 40°C. Add concentrated hydrochloric acid to neutralize to pH = 7....

Embodiment 3

[0036] 1. In a 2000ml reaction flask, add 900ml of water and 3.35mol of sodium carbonate, stir and mix evenly, then add 3mol of cis-1,3-dichloropropene (333g, content 99%), heat to 84°C, and vigorously stir and reflux for 8 hours , the residual amount of cis-1,3-dichloropropene detected by gas chromatography <0.5% is the end of the reflux. After the reflux is completed, let it stand for stratification, suck the red liquid in the upper layer into the receiving bottle, keep it warm and layered, and get 255g of 3-chloropropenol in the upper layer (water content is 5%), yield 87.3%;

[0037] 2. In a 2000ml reaction bottle, add 750g dimethyl sulfoxide, 1g hydroquinone and 3-chloropropenol obtained in step 1, heat to 80°C, and add 110g caustic soda in 20 times at the same time, the addition of caustic soda The time is about 0.5 hours. After the addition, keep stirring for 2 hours. After the reaction is completed, cool down to 40°C, add 37wt% concentrated hydrochloric acid to neutral...

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Abstract

The invention discloses a method for synthesizing propargyl alcohol. The method includes hydrolyzing 1, 3-dichloropropene in saturated alkali metal carbonate solution to obtain 3-chloropropene alcohol; removing hydrogen chloride from the 3-chloropropene alcohol under the condition of the presence of a polar solvent dimethyl sulfoxide and hydroxide of alkali metal so as to obtain the propargyl alcohol. The method has the advantages that the 1, 3-dichloropropene is used as a raw material, the raw material can come from wide sources, is inexpensive and is easily available, the propargyl alcohol is easy to dehydrate, energy can be saved, and environments can be protected; the propargyl alcohol obtained by the aid of the method is high in yield and purity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing propynyl alcohol. Background technique [0002] Propargyl alcohol is a key intermediate widely used in medicine, pesticides, electroplating and resin industries, and is mainly used in the preparation of pharmaceutical sulfadiazine, fosfomycin drugs, pesticide moxachlor, and electroplating nickel plating brightener. Regarding the synthesis of propynyl alcohol, calcium carbide was used to produce acetylene in the early stage, and then acetylene and formaldehyde were added to synthesize butynediol, and 30% propynyl alcohol was produced as a by-product. So far, this method is still the main source of obtaining propynyl alcohol, such as DE3717471, DE3717470, DE3717468, EP305688, DE10333598, SU1832674, DE4415380, CN104387236, US20140275639, CN103638937 and other patent applications all adopt this method. Someone tried to change the catalyst to increase the yi...

Claims

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Application Information

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IPC IPC(8): C07C29/58C07C33/042C07C29/12C07C33/42
CPCC07C29/12C07C29/58C07C33/042C07C33/423
Inventor 胡莉萍胡冠丰
Owner JINGCHU UNIV OF TECH
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