CN103265447A - Method for co-producing isopropanol and N,N-dimethyl acetamide - Google Patents
Method for co-producing isopropanol and N,N-dimethyl acetamide Download PDFInfo
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- CN103265447A CN103265447A CN2013101598126A CN201310159812A CN103265447A CN 103265447 A CN103265447 A CN 103265447A CN 2013101598126 A CN2013101598126 A CN 2013101598126A CN 201310159812 A CN201310159812 A CN 201310159812A CN 103265447 A CN103265447 A CN 103265447A
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- virahol
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Abstract
The invention relates to a method for co-producing isopropanol and N,N-dimethyl acetamide, belonging to a chemical synthesis technology field. The method of the invention solves the problems that isopropanol and N,N-dimethyl acetamide cannot be prepared at the same time, a product conversion rate is low and cost is high. The method comprises the following steps of: under action of a catalyst, using iso butyl acetate and dimethylamine as raw materials, and simultaneously obtain isopropanol and N,N-dimethyl acetamide through reaction. The catalyst is sodium alkoxide, which is one or more selected from sodium methoxide, sodium ethoxide, sodium isopropoxide, and sodium sec-butoxide, wherein a mol ratio of iso butyl acetate to dimethylamine is 1-1.0-6.0), reaction temperature is 20-80 DEG C, an introducing speed of dimethylamine is 10-20g/h. The method for co-producing isopropanol and N,N-dimethyl acetamide in the invention has advantages of high conversion rate and low cost.
Description
Technical field
The present invention relates to the method for the pure and mild acid amides of a kind of coproduction, be specifically related to the method for a kind of coproduction Virahol and N,N-dimethylacetamide, belong to technical field of chemical synthesis.
Background technology
Virahol (molecular formula: C
3H
8O; English name: be a kind of colourless transparent liquid Isopropanol), the smell like ethanol and acetone mixture is arranged, most organic solvents such as water-soluble, pure, ether, benzene, chloroform are a kind of important chemical product and raw material.Be mainly used in synthetic drugs, makeup, plastics, spices, coating etc.
N,N-dimethylacetamide (DMAC) is a kind of colourless transparent liquid, and boiling point is 166.1 ℃, and is flammable, can mix arbitrarily with organic solvents such as water, alcohol, ether, ester, benzene, trichloromethane and aromatic compounds.The application of DMAC is also very extensive, main solvent as heat-resisting synthon, plastics film, coating, medicine, vinyl cyanide spinning, the solvent that also can be used as extractive distillation, also can be used as the catalyzer in the organic synthesis, reactions such as cyclisation, halogenation, cyaniding, alkylation and dehydrogenation are accelerated, can also be improved the yield of primary product.Therefore this product is an industrial chemicals with very big market potentiality.
Mainly contain the hydration method for petrohol in the prior art, the hydration method is divided indirect hydration method and direct hydration method again.The hydration method utilizes propylene and sulfuric acid reaction to generate isopropyl acid sulphate earlier indirectly, makes Virahol through hydrolysis again.Owing to need to use the higher sulfuric acid of concentration in the reaction, can etching apparatus, therefore to the requirement height of equipment, thereby increased production cost.Direct hydration method is that propylene and water are heated, pressurizeed under the effect of catalyzer and carries out hydration reaction, generates Virahol.The catalyzer that these class methods are used has silicotungstic acid homogeneous catalyst, phosphoric acid and acidic cation-exchange resin etc., more use be the phosphoric acid catalyst that carrier is arranged, compare with indirect method, though there are not problems such as sulfuric acid corrosion and diluted acid concentrate in these class methods, the transformation efficiency of reaction is lower, and reaction also has a spot of by product to generate, in addition, the aftertreatment difficulty of reaction, product are difficult for purifying, thereby increase cost.In addition, and the Chinese patent application file (publication number: CN102746113A) relate to the method that a kind of acetone gas phase hydrogenation prepares Virahol, but side reaction takes place in its reaction process easily, catalyzer price height, reaction conditions is difficult for reaching.
And the method at synthetic DMAC mainly contains acetic anhydride method, acetyl chloride method and method of acetic acid in the prior art.Adopt the technology of aceticanhydride and dimethylamine prepared in reaction DMAC fairly simple, quality product is better, but aceticanhydride belongs to easy drugs processed, and the production cost height, and technical process is longer, is unwell to suitability for industrialized production.Acetyl chloride method is raw material with dimethylamine and Acetyl Chloride 98Min., adopt advanced catalyzed reaction and distillation technology, though can strengthen reaction process, cut down the consumption of energy, improve separating effect and product yield, but this method uses ether to be solvent in synthetic, solvent in use is difficult to control and reclaims, and in addition, Acetyl Chloride 98Min. causes corrosion to equipment easily, and ether belongs to the control chemical, buys, stores all inconvenient.Method of acetic acid is the synthetic N,N-dimethylacetamide of raw material for adopting acetic acid and dimethylamine, comprises legal two kinds of catalyzing and condensing method and high compression.This method yield is not very high, contain a large amount of unreacted acetic acid in the product, because acetic acid and N, the N-N,N-DIMETHYLACETAMIDE forms the high boiling point azeotropic mixture, make reaction finish the rectification and purification separation according to a conventional method of back product, must just can finish through series of processes such as neutralization, filtration, distillations, thereby make product purity low, and this synthetic method is to the equipment requirements height.
And correlative study and the document of coproduction Virahol and N,N-dimethylacetamide do not appear in the prior art.
Summary of the invention
The present invention is directed to the above-mentioned problems in the prior art, a kind of conversion rate of products height is provided, the coproduction Virahol that cost is low and the method for N,N-dimethylacetamide.
For achieving the above object, the present invention by the following technical solutions, a kind of coproduction Virahol and N, the method of N-N,N-DIMETHYLACETAMIDE: under the effect of catalyzer, be raw material with Iso Butyl Acetate and dimethylamine, through reaction, be prepared into Virahol and N,N-dimethylacetamide simultaneously.
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, catalyzer is selected one or more in sodium alkoxide, potassium alcoholate, the resene catalyzer for use.
As preferably, described catalyzer is selected sodium alkoxide for use, and described sodium alkoxide is one or more in sodium methylate, sodium ethylate, sodium isopropylate, the sec-butyl alcohol sodium.
Further preferred, described catalyzer is sodium methylate.
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, described method concrete steps with Iso Butyl Acetate and dimethylamine coproduction Virahol and N,N-dimethylacetamide are:
Be 1:(0.001～1.0 in molar ratio) Iso Butyl Acetate and catalyzer are put into reactor, and heat up.
After temperature rises to temperature of reaction, feed dimethylamine in the reactor and react.
After reaction finishes, through distillation, obtain Virahol and N,N-dimethylacetamide simultaneously.
Further, the method concrete steps of described coproduction Virahol and N,N-dimethylacetamide are: Iso Butyl Acetate is added reactor, under temperature is 25～35 ℃ condition catalyzer is added in the reactor, stir and feed dimethylamine down and form reaction solution.The regulation and control temperature of reaction makes temperature of reaction remain on 25～35 ℃.Add vitriol oil neutralization in reaction solution, fractionation is carried out in the back oil bath heating that neutralizes, and slowly heats up air distillation, the cut of collection Virahol and N,N-DIMETHYLACETAMIDE.The oil bath heating is adopted in fractionation of the present invention, is heated evenly, and Heating temperature is than water-bath height, at 100 ℃～250 ℃.
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, the mol ratio of described Iso Butyl Acetate and catalyzer is 1:(0.01～0.5).Appropriate amount of catalysts can improve speed of response and productive rate, catalyzer is crossed speed and the productive rate that can influence reaction at least, but when catalyzer is too much, not only speed of response is not significantly increased, too much catalyzer also can cause the catalyst recovery amount big, inorganic salt increase, and cause difficult treatment, thereby production cost is increased.
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, the mol ratio of described Iso Butyl Acetate and dimethylamine is 1:(1.0～6.0).
As preferably, the mol ratio of described Iso Butyl Acetate and dimethylamine is 1:(1.0～3.0).
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, described temperature of reaction is 20～80 ℃.
As preferably, described temperature of reaction is 30～60 ℃.Under the temperature of reaction of this scope, catalyzer can be brought into play the high efficiency of its Dichlorodiphenyl Acetate isopropyl ester and dimethylamine reaction better, makes coproduction Virahol of the present invention and N,N-DIMETHYLACETAMIDE can obtain higher reaction conversion ratio.
In the method for above-mentioned coproduction Virahol and N,N-dimethylacetamide, the feeding speed of described dimethylamine is 10～20g/h.
As preferably, the feeding speed of described dimethylamine is 13～18g/h.Slowly can cause speed of response slow if the feeding speed of dimethylamine is crossed, productive rate is low excessively.But the excessive velocities that feeds dimethylamine can cause dimethylamine to have little time reaction and just overflow, and causes the waste of raw material easily, therefore, the present invention with the feeding speed control of dimethylamine at 13～18g/h.
The chemical equation of described coproduction Virahol and N,N-dimethylacetamide is as follows:
In sum, the present invention has the following advantages:
1), the present invention adopts Iso Butyl Acetate cheap and easy to get and dimethylamine as basic raw material, the method for this coproduction Virahol and N,N-dimethylacetamide is not only simple to operate, and production cost is low, is fit to large-scale industrialization production.
2), to select sodium alkoxide for use be catalysts in the present invention, greatly improved the transformation efficiency of product, and the yield of Virahol and N,N-dimethylacetamide is all reached more than 95.0%.
3), the present invention adopts continuous conduit reaction, the plant factor height, energy consumption is low, makes this coproduction Virahol and N,N-dimethylacetamide to not pollution of environment, reaches the requirement of Green Chemistry.
Embodiment
In order to make technical problem solved by the invention, technical scheme and beneficial effect clearer, below in conjunction with specific embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explaining the present invention, and be not used in restriction the present invention.
Embodiment 1:
The sodium alkoxide of catalyzer is selected sodium methylate for use.
At the 500mL four-hole boiling flask electric mixing device, thermometer, constant pressure funnel and reflux condensing tube are installed, prolong peace one Calcium Chloride Powder Anhydrous drying tube suitable for reading.The 500g Iso Butyl Acetate is joined in the reaction flask, rise to 30 ℃, slowly the 50g sodium methylate is joined in the reaction flask, stir and feed dimethylamine formation reaction solution down, the feeding speed of dimethylamine is 18g/h.The regulation and control temperature of reaction makes temperature of reaction remain on 30 ℃.The 20g vitriol oil is added reaction flask reaction solution is neutralized, make simple fractionation plant into, fractionation is carried out in the oil bath heating, slowly heats up air distillation.Collect the cut temperature earlier at the cut below 81 ℃, main component is the mixture of dimethylamine, Virahol, Iso Butyl Acetate.Collect cut under the cut temperature is 80～82 ℃ condition from described mixture, temperature can not surpass 120～140 ℃ in the reactor, and the cut main component of collecting is Virahol.When temperature reaches 120～140 ℃, stop air distillation, depleted of steam, and be cooled to 40 ℃, and slowly open vacuum, collect the cut temperature at the cut below 70 ℃, main component is Virahol and N,N-dimethylacetamide, recycled.
The Virahol yield is 96.7%, and content 99.2%, DMAC yield are 95.1%, content 99.8%.
Embodiment 2
The sodium alkoxide of catalyzer is selected sodium ethylate for use.
At the 500mL four-hole boiling flask electric mixing device, thermometer, constant pressure funnel and reflux condensing tube are installed, prolong peace one Calcium Chloride Powder Anhydrous drying tube suitable for reading.The 500g Iso Butyl Acetate is joined in the reaction flask, rise to 28 ℃, slowly the 60g sodium ethylate is joined in the reaction flask, stir and feed dimethylamine formation reaction solution down, the feeding speed of dimethylamine is 13g/h.The regulation and control temperature of reaction makes temperature of reaction remain on 28 ℃.The 20g vitriol oil is added reaction flask neutralizes reaction solution.All the other are all with embodiment 1.
The Virahol yield is 96.9%, and content 99.1%, DMAC yield are 96.0%, content 99.4%.
Embodiment 3
The sodium alkoxide of catalyzer is selected sodium isopropylate for use.
At the 500mL four-hole boiling flask electric mixing device, thermometer, constant pressure funnel and reflux condensing tube are installed, prolong peace one Calcium Chloride Powder Anhydrous drying tube suitable for reading.The 500g Iso Butyl Acetate is joined in the reaction flask, rise to 32 ℃, slowly the 70g sodium isopropylate is joined in the reaction flask, stir and feed dimethylamine formation reaction solution down, the feeding speed of dimethylamine is 15g/h.The regulation and control temperature of reaction makes temperature of reaction remain on 32 ℃.The 20g vitriol oil is added reaction flask neutralizes reaction solution.All the other are all with embodiment 1.
The Virahol yield is 96.6%, and content 99.1%, DMAC yield are 97.0%, content 99.2%.
Embodiment 4
The sodium alkoxide of catalyzer is selected sec-butyl alcohol sodium for use.
At the 500mL four-hole boiling flask electric mixing device, thermometer, constant pressure funnel and reflux condensing tube are installed, prolong peace one Calcium Chloride Powder Anhydrous drying tube suitable for reading.The 500g Iso Butyl Acetate is joined in the reaction flask, rise to 35 ℃, slowly 65g sec-butyl alcohol sodium is joined in the reaction flask, stir and feed dimethylamine formation reaction solution down, the feeding speed of dimethylamine is 17g/h.The regulation and control temperature of reaction makes temperature of reaction remain on 35 ℃.The 20g vitriol oil is added reaction flask neutralizes reaction solution.All the other are all with embodiment 1.
Virahol yield 96.8%, content 99.0%, DMAC yield are 96.5%, content 99.2%.
In sum, in conjunction with four embodiment, the method for coproduction Virahol of the present invention and DMAC has following positively effect:
1), the present invention adopts Iso Butyl Acetate cheap and easy to get and dimethylamine as basic raw material, the method for this coproduction Virahol and N,N-dimethylacetamide is not only simple to operate, and production cost is low, is fit to large-scale industrialization production.
2), to select sodium alkoxide for use be catalysts in the present invention, greatly improved the transformation efficiency of product, and the yield of Virahol and N,N-dimethylacetamide is all reached more than 95.0%.
3), the present invention adopts continuous conduit reaction, the plant factor height, energy consumption is low, makes this coproduction Virahol and N,N-dimethylacetamide to not pollution of environment, reaches the requirement of Green Chemistry.
The above only is preferred embodiment of the present invention, not in order to limiting the present invention, all any modifications of doing within the spirit and principles in the present invention, is equal to and replaces and improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. the method for a coproduction Virahol and N,N-dimethylacetamide is characterized in that, under the effect of catalyzer, is raw material with Iso Butyl Acetate and dimethylamine, through reaction, is prepared into Virahol and N,N-dimethylacetamide simultaneously.
2. the method for a kind of coproduction Virahol according to claim 1 and N,N-dimethylacetamide is characterized in that, described catalyzer is sodium alkoxide, and described sodium alkoxide is one or more in sodium methylate, sodium ethylate, sodium isopropylate, the sec-butyl alcohol sodium.
3. the method for a kind of coproduction Virahol according to claim 1 and 2 and N,N-dimethylacetamide is characterized in that, described method concrete steps with Iso Butyl Acetate and dimethylamine coproduction Virahol and N,N-dimethylacetamide are:
Be 1:(0.001～1.0 in molar ratio) Iso Butyl Acetate and catalyzer are put into reactor, and heat up;
After temperature rises to temperature of reaction, feed dimethylamine in the reactor and react;
After reaction finishes, through distillation, obtain Virahol and N,N-dimethylacetamide simultaneously.
4. the method for a kind of coproduction Virahol according to claim 3 and N,N-dimethylacetamide is characterized in that, the mol ratio of described Iso Butyl Acetate and catalyzer is 1:(0.01～0.5).
5. the method for a kind of coproduction Virahol according to claim 3 and N,N-dimethylacetamide is characterized in that, the mol ratio of described Iso Butyl Acetate and dimethylamine is 1:(1.0～6.0).
6. the method for a kind of coproduction Virahol according to claim 5 and N,N-dimethylacetamide is characterized in that, the mol ratio of described Iso Butyl Acetate and dimethylamine is 1:(1.0～3.0).
7. the method for a kind of coproduction Virahol according to claim 3 and N,N-dimethylacetamide is characterized in that, described temperature of reaction is 20～80 ℃.
8. the method for a kind of coproduction Virahol according to claim 7 and N,N-dimethylacetamide is characterized in that, described temperature of reaction is 30～60 ℃.
9. the method for a kind of coproduction Virahol according to claim 5 and N,N-dimethylacetamide is characterized in that, the feeding speed of described dimethylamine is 10～20g/h.
10. the method for a kind of coproduction Virahol according to claim 9 and N,N-dimethylacetamide is characterized in that, the feeding speed of described dimethylamine is 13～18g/h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2013101598126A CN103265447A (en) | 2013-05-02 | 2013-05-02 | Method for co-producing isopropanol and N,N-dimethyl acetamide |
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| CN2013101598126A CN103265447A (en) | 2013-05-02 | 2013-05-02 | Method for co-producing isopropanol and N,N-dimethyl acetamide |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342862A (en) * | 1964-08-14 | 1967-09-19 | Monsanto Co | Method for producing dimethylacetamide |
| CN102702009A (en) * | 2012-06-11 | 2012-10-03 | 科凯精细化工（上海）有限公司 | Method for synthesizing diethanol amide |
-
2013
- 2013-05-02 CN CN2013101598126A patent/CN103265447A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342862A (en) * | 1964-08-14 | 1967-09-19 | Monsanto Co | Method for producing dimethylacetamide |
| CN102702009A (en) * | 2012-06-11 | 2012-10-03 | 科凯精细化工（上海）有限公司 | Method for synthesizing diethanol amide |
Non-Patent Citations (1)
| Title |
|---|
| 刘婷: "乙酸甲酯胺化制N,N-二甲基乙酰胺的研究", 《甘肃化工》, no. 4, 31 December 2004 (2004-12-31), pages 31 - 33 * |
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Application publication date: 20130828 |