CN101456794A - Method for producing 4-chloro-3-hydroxyl-1-butene - Google Patents
Method for producing 4-chloro-3-hydroxyl-1-butene Download PDFInfo
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- CN101456794A CN101456794A CNA2009100287354A CN200910028735A CN101456794A CN 101456794 A CN101456794 A CN 101456794A CN A2009100287354 A CNA2009100287354 A CN A2009100287354A CN 200910028735 A CN200910028735 A CN 200910028735A CN 101456794 A CN101456794 A CN 101456794A
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Abstract
The invention relates to a method for producing 4-chlorine-3-hydroxyl-1-butylene, which is to take 1,3-butadiene as a raw material, and perform addition reaction under the action of hypochlorous acid to obtain the 4-chlorine-3-hydroxyl-1-butylene, wherein the temperature of the addition reaction is between 10 DEG C below zero and 10 DEG C. The method prepares the target product by directly taking the hypochlorous acid as a catalyst and performing addition reaction on the 1,3-butadiene, and can completely avoid the precipitation phenomenon, reduce the equipment investment, improve the utilization rate of equipment, and simplify the operation.
Description
Technical field
The present invention relates to a kind of method of the 4-of production chloro-3-hydroxyl-1-butylene.
Background technology
4-chloro-3-hydroxyl-1-butylene is a kind of important organic chemical industry's intermediate.Once introduced in RICHARDG.KADESCH VOL68 with 1,3-butadiene and carbonic acid gas and lead to the amount of 6:1 in 3.5% the calcium hypochlorite solution, this kind method because the concentration of Losantin is too low, causes equipment too big in Chemical Manufacture; In addition, desire is strict controlled in 6:1 with the velocity ratio of 1,3 divinyl and carbonic acid gas, actual being not easy operated, and a large amount of precipitation of calcium carbonate that produce in the reaction process also can cause a large amount of wastes of raw material 1,3-butadiene, so this method is unwell to Chemical Manufacture.
Summary of the invention
Technical problem to be solved by this invention is in order to overcome the deficiencies in the prior art, the production method of a kind of facility investment 4-chloro-3-hydroxyl-1-butylene low, simple to operate to be provided.
For solving above technical problem, the present invention takes following technical scheme:
A kind of production method of 4-chloro-3-hydroxyl-1-butylene is a raw material with the 1,3-butadiene, addition reaction takes place under hypochlorous effect obtain described 4-chloro-3-hydroxyl-1-butylene, and the temperature of addition reaction is between-10～10 ℃.
As the further embodiment of the present invention: at first mineral acid is joined that reaction makes hypochlorous acid in the aqueous solution of hypochlorous an alkali metal salt or alkaline earth salt, and then in reaction solution, feed 1,3-butadiene.
The mass percent of described mineral acid is preferably 10%～20%.
The mass percent of salt is preferably 40%～50% in the aqueous solution of described hypochlorous an alkali metal salt or alkaline earth salt.
Because the technique scheme utilization, the present invention compared with prior art has following advantage:
Directly be oxygenant with hypochlorous acid, 1,3-butadiene carried out addition make target product, can thoroughly solve sedimentation problem, reduction equipment drops into, and improves plant factor and simplifies the operation.
Embodiment
Below the specific embodiment of the present invention is described, but be not limited to these embodiment.
Embodiment 1
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 0～3 ℃, hydrochloric acid 300 grams of dropping 15%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl, keep temperature of reaction between 0～3 ℃, after 1 hour, reach reaction end with the starch potassium iodide paper detection, the discovery system does not have and sinks to the bottom, the aqueous solution merges diethyl ether solution with extracted with diethyl ether (6000 milliliters are divided six extractions), reclaim ether, get 221 gram solid 4-chloro-3-hydroxyl-1-butylene.Yield 48.7%.
Embodiment 2
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 0～3 ℃, hydrochloric acid 150 grams of dropping 30%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl keeps temperature of reaction between 0～3 ℃, after 1 hour, reach reaction end with the starch potassium iodide paper detection, the discovery system does not have and sinks to the bottom, and the aqueous solution is with extracted with diethyl ether (6000 milliliters are divided six extractions), merge diethyl ether solution, reclaim diethyl ether solution, obtain 207 grams, 4-chloro-3-hydroxyl-1-butylene.Yield 45.6%.
Embodiment 3
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 8～10 ℃, hydrochloric acid 300 grams of dropping 15%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl, keep temperature of reaction between 8～10 ℃, after 1 hour, detect with starch potassium iodide paper and to reach reaction end, the discovery system does not have and sinks to the bottom, (6000 milliliters of extracted with diethyl ether of the aqueous solution, divide the i.e. 1000 milliliters of * 6 of six extractions), merge diethyl ether solution, reclaim and go diethyl ether solution to obtain 210 gram 4-chloro-3-hydroxyl-1-butylene.Yield 46.35%.
Embodiment 4
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 8～10 ℃, hydrochloric acid 300 grams of dropping 15%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl, keep temperature of reaction between 2～3 ℃, after 1 hour, detect with starch potassium iodide paper and to reach reaction end, the discovery system does not have and sinks to the bottom, and the aqueous solution is with extracted with diethyl ether (six extractions of 6000 milliliters of branches i.e. 1000 milliliters of * 6), merge diethyl ether solution, reclaim and go diethyl ether solution to obtain 220 gram 4-chloro-3-hydroxyl-1-butylene.Yield 48.6%.
Embodiment 5
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 0～3 ℃, sulfuric acid 300 grams of dropping 15%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl, keep temperature of reaction between 0～3 ℃, after 1 hour, detect with starch potassium iodide paper and to reach reaction end, the discovery system does not have and sinks to the bottom, and the aqueous solution is with extracted with diethyl ether (six extractions of 6000 milliliters of branches i.e. 1000 milliliters of * 6), merge diethyl ether solution, reclaim and go diethyl ether solution to obtain 202 gram 4-chloro-3-hydroxyl-1-butylene.Yield 44.6%.
Embodiment 6
The aqueous sodium hypochlorite solution that in 1000 milliliters reaction flask, adds 700 grams 50%, controlled temperature is between 0～3 ℃, phosphoric acid 300 grams of dropping 15%, make and be acid, in reaction flask, feed 1 then, the 3-divinyl, keep temperature of reaction between 0～3 ℃, after 1 hour, detect with starch potassium iodide paper and to reach reaction end, the discovery system does not have and sinks to the bottom, and the aqueous solution is with extracted with diethyl ether (six extractions of 6000 milliliters of branches i.e. 1000 milliliters of * 6), merge diethyl ether solution, reclaim and go diethyl ether solution to obtain 208 gram 4-chloro-3-hydroxyl-1-butylene.Yield 45.9%.
Comparative example
The Eusol (main component is a Losantin) that in 1000 milliliters reaction flask, adds 800 grams 3.5%, back controlled temperature is between 0～3 ℃, in reaction flask, lead to 1,3-divinyl and carbonic acid gas (the control flow velocity is 6 to 1), after 1 hour, reach reaction end with the starch potassium iodide paper detection, a large amount of muddy in the discovery system, cross a large amount of post precipitations of elimination extracted with diethyl ether (six extractions of 6000 milliliters of branches i.e. 1000 milliliters of * 6), merge diethyl ether solution, recovery goes diethyl ether solution to obtain 15 gram 4-chloro-3-hydroxyl-1-butylene, yield 46.3%.
Above-described only is preferred implementation of the present invention.Should be pointed out that for the person of ordinary skill of the art under the prerequisite that does not break away from patent principle of the present invention, can also make some distortion and improvement, these also should be considered as belonging to protection scope of the present invention.
Claims (4)
1, a kind of production method of 4-chloro-3-hydroxyl-1-butylene is characterized in that: be raw material with the 1,3-butadiene, addition reaction takes place and generates described 4-chloro-3-hydroxyl-1-butylene in it under hypochlorous effect, and the temperature of addition reaction is between-10～10 ℃.
2, the production method of a kind of 4-chloro-3-hydroxyl-1-butylene according to claim 1, it is characterized in that: at first mineral acid is joined in the aqueous solution of hypochlorous an alkali metal salt or alkaline earth salt, reaction makes hypochlorous acid, and then feeds 1,3-butadiene in reaction solution.
3, the production method of a kind of 4-chloro-3-hydroxyl-1-butylene according to claim 2, it is characterized in that: the mass percent of described mineral acid is 10%～20%.
4, according to the production method of claim 2 or 3 described a kind of 4-chloro-3-hydroxyl-1-butylene, it is characterized in that: the mass percent of salt is 40%～50% in the aqueous solution of described hypochlorous an alkali metal salt or alkaline earth salt.
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| CNA2009100287354A CN101456794A (en) | 2009-01-04 | 2009-01-04 | Method for producing 4-chloro-3-hydroxyl-1-butene |
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| CNA2009100287354A CN101456794A (en) | 2009-01-04 | 2009-01-04 | Method for producing 4-chloro-3-hydroxyl-1-butene |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104961626A (en) * | 2015-05-15 | 2015-10-07 | 中国科学院化学研究所 | Hydroxyl bromine compound preparation method |
| CN106831511A (en) * | 2017-01-24 | 2017-06-13 | 郯城博化化工科技有限公司 | A kind of preparation method of multi-thiol compound |
-
2009
- 2009-01-04 CN CNA2009100287354A patent/CN101456794A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104961626A (en) * | 2015-05-15 | 2015-10-07 | 中国科学院化学研究所 | Hydroxyl bromine compound preparation method |
| CN106831511A (en) * | 2017-01-24 | 2017-06-13 | 郯城博化化工科技有限公司 | A kind of preparation method of multi-thiol compound |
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Open date: 20090617 |