CN102633602A - Method for preparing 3-hexine-2,5-glycol under ordinary pressure - Google Patents
Method for preparing 3-hexine-2,5-glycol under ordinary pressure Download PDFInfo
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- CN102633602A CN102633602A CN2012101262163A CN201210126216A CN102633602A CN 102633602 A CN102633602 A CN 102633602A CN 2012101262163 A CN2012101262163 A CN 2012101262163A CN 201210126216 A CN201210126216 A CN 201210126216A CN 102633602 A CN102633602 A CN 102633602A
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Abstract
The invention relates to a method for preparing 3-hexine-2,5-glycol under ordinary pressure. The method comprises the following steps of: reacting acetylene and acetaldehyde in an ordinary-pressure reaction kettle under the catalysis of an efficient solid catalyst potassium tert-butoxide, wherein acetylene and acetaldehyde serve as raw materials, dimethylbenzene serves as solvent, the molar ratio of acetylene to acetaldehyde equals to 1: 2 to 1: 3, the mass ratio of the efficient solid catalyst to acetaldehyde equals to 0.5: 1 to 1: 1, the mass ratio of dimethylbenzene to acetaldehyde is 15: 1 to 20: 1, the reaction temperature ranges from minus 6 DEG C to 3 DEG C, and the reaction time lasts for 2.5 hours to 3.5 hours; and performing water washing and solvent removal on the organic phase of the reaction liquid, and then performing reduced-pressure rectification to obtain the product 3-hexine-2,5-glycol, wherein the productivity can reach 80%, and the purity reaches 99%. When the method is adopted for synthesizing 3-hexine-2,5-glycol, the reaction can be performed under the ordinary pressure; and the preparation method has the characteristics of simple process, low cost, high efficiency and the like.
Description
Technical field
The present invention relates to a kind of 3-hexin-2, the compound method of 5-glycol is specifically related to a kind of normal pressure and prepares 3-hexin-2, the method for 5-glycol.
Background technology
3-hexin-2, the 5-glycol, molecular formula is C
6H
10O
2, structural formula is seen formula 1.
Formula 1
3-hexin-2; The 5-glycol has good wettability, low bubble defoaming, polymolecularity and good rust inhibition etc.; Various excellent characteristic make its purposes very extensively, and rust cleaning etc. is stained with in the acid of the acidleach of the stablizer of the soporific when can be used for paint (particularly water-based paint), medicine intermediate, live fish transportation, special solvent, viscosity depressant, nickel plating or copper-plated lustering agent, chlorinated hydrocarbon, agricultural chemicals, printing and dyeing, prepared Chinese ink, printing ink, the soup of considering, sticker, metallic substance, removing rolled iron phosphorus, hardware pickling descaling, metallic substance or workpiece.Its important application is the crucial active principle as the efficient acidification corrosion inhibitor under HTHP, the concentrated hydrochloric acid in the oil gas well.
According to the difference of processing condition, preparation 3-hexin-2, the method for 5-glycol mainly contains base catalysis method, grignard reagent method and alumina load type catalysis method.But not only raw materials cost is high for the base catalysis method, solvent is volatile, and aftertreatment is loaded down with trivial details, productive rate is lower; Production operation is complicated, equipment requirements is high, side reaction is more because of using form reagent makes for the grignard reagent method; Alumina load type catalysis method reaction can not be carried out under condition of normal pressure, so economic benefit is all relatively poor because of reaction conditions is a low pressure environment.
At present, produce 3-hexin-2 in the world, the producer of 5-glycol mainly is the BASF AG of Germany; The domestic 3-hexin-2 of at present producing, the enterprise of 5-glycol is considerably less, and Sichuan one tame enterprise production is only arranged; And industrial scale is less, and quality product can not reach international standards fully.The technology that BASF adopts is that acetylene and acetaldehyde react generation 3-hexin-2 under 0.6-1.0MPa pressure, the 5-glycol, and yield is about 90%.The Zhijiang River, Sichuan new chemical materials ltd patent (application number: 201110152117.8; Publication number: CN102285867A) described 3-hexin-2; The compound method of 5-glycol, reaction are adjusted to pressure under the 0.5-1.5MPa in autoclave carries out, and the reaction times is 3-10h; Yield is about 70%, and technology is all complicated.
Summary of the invention
The purpose of this invention is to provide a kind of normal pressure and prepare 3-hexin-2, the method for 5-glycol, characteristics such as technology is simple, cost is low, efficient height that it has.
The objective of the invention is to reach through following measure: adopt the high-performance solid catalyzer, acetylene and acetaldehyde can react under normal pressure and generate 3-hexin-2,5-glycol.
A kind of normal pressure among the present invention prepares 3-hexin-2, and the method for 5-glycol is characterized in that comprising successively following step:
1) acetylene and acetaldehyde are raw material, and YLENE is solvent, under the high-performance solid catalyst; In normal-pressure reaction kettle, react; The mol ratio of acetylene and acetaldehyde is 1: 2-1: 3, and the mass ratio of high-performance solid catalyzer and acetaldehyde is 0.5: 1-1: 1, the mass ratio of YLENE and acetaldehyde is 15: 1-20: 1; Temperature of reaction is-6-3 ℃, and the reaction times is 2.5-3.5h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2, the 5-glycol.
Press such scheme, a kind of normal pressure prepares 3-hexin-2, and the method for 5-glycol is characterized in that described high-performance solid catalyzer is a potassium tert.-butoxide.
A kind of normal pressure among the present invention prepares 3-hexin-2, the method for 5-glycol, and its route is seen formula 2.
Formula 2
A kind of normal pressure among the present invention prepares 3-hexin-2, and the method for 5-glycol has following advantage:
1) compare with alumina load type catalysis method, preparation method of the present invention can carry out in normal-pressure reaction kettle, and shortens the reaction times;
2) compare with the base catalysis method, raw material is easy to get among the preparation method of the present invention, cost is lower;
3) compare with the grignard reagent method, preparation method of the present invention is simple to operate, economical rationality, be applicable to industriallization;
4) after preparation method of the present invention reacted completion, aftertreatment technology was simplified, cost is low, productive rate is high.
Embodiment
Further introduce the present invention through embodiment below, but embodiment can not be construed as limiting the invention.
Embodiment 1
1) in normal-pressure reaction kettle, add the 100mL xylene solution that is dissolved with the 18g potassium tert.-butoxide, logical a certain amount of acetylene drips the 25mL xylene solution that is dissolved with 8.8g acetaldehyde, and 2 ℃ of environment react 1h down, add 50mL YLENE, continue reaction 2h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2,5-glycol, yield are 75.5%, and purity is 99%.
Embodiment 2
1) in normal-pressure reaction kettle, add the 100mL xylene solution that is dissolved with the 20g potassium tert.-butoxide, logical a certain amount of acetylene drips the 25mL xylene solution that is dissolved with 8.8g acetaldehyde, and 2 ℃ of environment react 1h down, add 50mL YLENE, continue reaction 2h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2,5-glycol, yield are 76.3%, and purity is 99%.
Embodiment 3
1) in normal-pressure reaction kettle, add the 100mL xylene solution that is dissolved with the 18g potassium tert.-butoxide, logical a certain amount of acetylene drips the 25mL xylene solution that is dissolved with 8.8g acetaldehyde, and-2 ℃ of environment react 1h down, add 50mL YLENE, continue reaction 1.75h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2,5-glycol, yield are 74.5%, and purity is 99%.
Embodiment 4
1) in normal-pressure reaction kettle, add the 100mL xylene solution that is dissolved with the 20g potassium tert.-butoxide, logical a certain amount of acetylene drips the 25mL xylene solution that is dissolved with 8.8g acetaldehyde, and-2 ℃ of environment react 1h down, add 50mL YLENE, continue reaction 1.75h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2,5-glycol, yield are 75.2%, and purity is 99%.
Claims (3)
1. a normal pressure prepares 3-hexin-2, and the method for 5-glycol is characterized in that: adopt the high-performance solid catalyzer, acetylene and acetaldehyde can react under normal pressure and generate 3-hexin-2,5-glycol.
2. a kind of normal pressure as claimed in claim 1 prepares 3-hexin-2, and the method for 5-glycol is characterized in that comprising following step:
1) acetylene and acetaldehyde are raw material, and YLENE is solvent, under the catalysis of high-performance solid catalyzer; In normal-pressure reaction kettle, react; The mol ratio of acetylene and acetaldehyde is 1: 2-1: 3, and the mass ratio of high-performance solid catalyzer and acetaldehyde is 0.5: 1-1: 1, the mass ratio of YLENE and acetaldehyde is 15: 1-20: 1; Temperature of reaction is-6-3 ℃, and the reaction times is 2.5-3.5h;
2) with behind 3 precipitations of reaction solution organic phase washing, carry out rectification under vacuum, collect 119-123 ℃ cut, obtain product 3-hexin-2, the 5-glycol.
3. prepare 3-hexin-2 like claim 1 and 2 described a kind of normal pressures, the method for 5-glycol is characterized in that described high-performance solid catalyzer is a potassium tert.-butoxide.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012101262163A CN102633602A (en) | 2012-04-26 | 2012-04-26 | Method for preparing 3-hexine-2,5-glycol under ordinary pressure |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875332A (en) * | 2012-10-12 | 2013-01-16 | 隆昌天康精细化工有限公司 | Process for synthesizing 3-hexyne-2,5-diol through slurry bed based on low pressure method |
| CN113666802A (en) * | 2021-08-30 | 2021-11-19 | 四川众邦制药有限公司 | Method for synthesizing and extracting and purifying 3-hexyne-2, 5-diol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0285755A2 (en) * | 1987-04-04 | 1988-10-12 | Hüls Aktiengesellschaft | Process for the preparation of alkine diols by the reaction of ketones with acetylene |
| CN1247181A (en) * | 1999-08-25 | 2000-03-15 | 成都惟精防水材料研究所 | One-step synthesizing process of 2,5-dimethyl-2,5-hexanediol |
| CN1312784A (en) * | 1998-08-17 | 2001-09-12 | 巴斯福股份公司 | Process for preparing alkyndialcohol |
| CN102285867A (en) * | 2011-06-08 | 2011-12-21 | 四川之江化工新材料有限公司 | Synthesis method of 3-hexyne-2,5-diol |
-
2012
- 2012-04-26 CN CN2012101262163A patent/CN102633602A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0285755A2 (en) * | 1987-04-04 | 1988-10-12 | Hüls Aktiengesellschaft | Process for the preparation of alkine diols by the reaction of ketones with acetylene |
| CN1312784A (en) * | 1998-08-17 | 2001-09-12 | 巴斯福股份公司 | Process for preparing alkyndialcohol |
| CN1247181A (en) * | 1999-08-25 | 2000-03-15 | 成都惟精防水材料研究所 | One-step synthesizing process of 2,5-dimethyl-2,5-hexanediol |
| CN102285867A (en) * | 2011-06-08 | 2011-12-21 | 四川之江化工新材料有限公司 | Synthesis method of 3-hexyne-2,5-diol |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875332A (en) * | 2012-10-12 | 2013-01-16 | 隆昌天康精细化工有限公司 | Process for synthesizing 3-hexyne-2,5-diol through slurry bed based on low pressure method |
| CN102875332B (en) * | 2012-10-12 | 2014-08-13 | 隆昌天康精细化工有限公司 | Process for synthesizing 3-hexyne-2,5-diol through slurry bed based on low pressure method |
| CN113666802A (en) * | 2021-08-30 | 2021-11-19 | 四川众邦制药有限公司 | Method for synthesizing and extracting and purifying 3-hexyne-2, 5-diol |
| CN113666802B (en) * | 2021-08-30 | 2023-09-01 | 四川众邦新材料股份有限公司 | Method for synthesizing and extracting purified 3-hexyne-2, 5-diol |
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Application publication date: 20120815 |