CN106008177A - Method of purifying dipropylene glycol dimethyl ether - Google Patents
Method of purifying dipropylene glycol dimethyl ether Download PDFInfo
- Publication number
- CN106008177A CN106008177A CN201610336673.3A CN201610336673A CN106008177A CN 106008177 A CN106008177 A CN 106008177A CN 201610336673 A CN201610336673 A CN 201610336673A CN 106008177 A CN106008177 A CN 106008177A
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- Prior art keywords
- dipropylene glycol
- rectification
- methyl ether
- tower
- product
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
Abstract
The invention relates to a method of purifying dipropylene glycol dimethyl ether. The method includes: using a crude dipropylene glycol monomethyl ether product as a raw material; enabling the crude dipropylene glycol monomethyl ether product and excessive mixed aldehyde waste liquid to be in aldolization under catalysis action of sulfuric acid, and enabling propylene glycol in the crude product to be in reaction to generate a cyclic acetal structure; performing negative pressure rectification after the reaction is finished, and respectively collecting solutions after rectification according to difference in ingredients. The method has the advantages that the crude dipropylene glycol monomethyl ether product of propylene glycol ether production enterprises is adopted as the raw material; through the method, product quality can be improved greatly, and producing of a high-quality product is ensured; dipropylene glycol monomethyl ether can be purified to form environment-friendly solvents like high-purity dipropylene glycol monomethyl ether urgently needed by downstream enterprises of waterborne latex, plasticizers, coatings, printing ink and cleaning agents.
Description
Technical field
The invention belongs to the safety in production field of organic solvent, particularly to a kind of side purifying dimethyl ether
Method.
Background technology
Both having contained alcoholic extract hydroxyl group in alcohol ether product, and contained again ehter bond, it is that the field of new such as coating and ink is applied very
Solvent widely.Although the starting of propylene glycol product is later than glycol ether product, but from nineteen eighty-two Europe chemical industry and poison
Reason center has been delivered the toxicity research about glycol ether product and has been reported, it is indicated that glycol ether product is to the bone marrow of animal, lymph
Tissue and embryo all have toxicity in various degree, and after may result in the pathological changes of blood, glycol ether product receives domestic and international one
The restriction of a little rule and standard, its yield is in progressively atrophy.
Owing to several years ago glycol ether series products is classified as and need to close by height by forms such as REACH regulations by European Union area
The material (SVHC) of note, China is also with GB 24,408 2009 " limits of harmful substances in exterior coating for building ", GB
24409 2009 " limits of harmful substances in car paint " and GB 24410 are " in indoor decorating and refurnishing materials water-borne wood coating
Limits of harmful substances " etc. the form of mandatory standard for the second in building external paint, car paint and water-borne wood coating
The harmful substances such as glycol ethers propose limitation requirement, so the most generally limiting use glycol ether product.And
Therewith similar nature but toxicity the lowest propylene glycol series product just obtained developing faster.
Existing propylene glycol monomethyl ether produces and mainly uses expoxy propane and methanol to react under the conditions of base catalyst, raw
Become propylene glycol monomethyl ether and the different methyl ether of by-product propylene glycol, dipropylene glycol methyl ether；Typically by accomplished continuously or intermittently essence in commercial production
Evaporate and alcohol ether product is proposed, the heavy constituent by-product generated during wherein dipropylene glycol methyl ether is propylene glycol monomethyl ether course of reaction, be
A kind of outstanding solvent, has been widely used in Chemical Manufacture.Product due to dipropylene glycol methyl ether general in course of reaction
Measuring less, the general mode using evaporating kettle rectification Batch Process produces proposition.
Generate owing to having a small amount of propylene glycol during etherification reaction, and propylene glycol essence close with dipropylene glycol methyl ether boiling point
Evaporating and be difficult to separation, the most a small amount of heavy constituent impurity may also appear in dipropylene glycol methyl ether finished product.Due to factors above
Product content after dipropylene glycol methyl ether rectification, typically between 95%-96%, has had a strong impact on dipropylene glycol methyl ether and follow-up
The range of application of product.
Methanol solution owing to using when producing propylene glycol monomethyl ether by continuity method now contains a small amount of moisture and causes etherificate
Water reaction in course of reaction oxypropylene and methanol generates a small amount of propylene glycol, and this reaction cannot be avoided.Propylene glycol simultaneously
Owing to dissolving each other with dipropylene glycol methyl ether, four kinds of component boiling spreads of dipropylene glycol methyl ether completely include propylene glycol, it is desirable to directly
The method using rectification separates and unrealistic.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method purifying dimethyl ether, can be greatly improved
Product quality, it is ensured that the manufacture of quality product.
For solving above-mentioned technical problem, the technical scheme is that the method purifying dimethyl ether, its innovation
Point is: with dipropylene glycol methyl ether crude product as raw material, first carries out dipropylene glycol methyl ether crude product and excess under sulfuric acid catalysis
The aldolisation of mixing aldehydes waste liquid, reacts the propylene glycol in crude product and generates cyclic ketal structure；Then carry out after having reacted
Negative pressure rectification, finally collects according to composition difference respectively by the solution after rectification.
Further, described method specifically comprises the following steps that
(1) tower bottoms component analysis: the sulfuric acid catalyst tentatively deviate from will be completed and heavy constituent dipropylene glycol methyl ether squeezes into reaction
Still, measures mass fraction and the mass fraction of Feldalat NM of water in tower bottoms, and then detecting and calculate can be by gas in tower bottoms
The mass fraction of some components of phase chromatograph detection, can be included the third two by some components of gas chromatographic detection in described tower bottoms
The different methyl ether of alcohol methyl ether, propylene glycol, dipropylene glycol methyl ether, propylene glycol and other impurity；
(2) aldolisation: the mixing aldehydes waste liquid and the mass ratio that add excess in dipropylene glycol methyl ether crude product are the sulfur of 0.2%
Acid, is then heated to 90 DEG C and is stirred ensureing uniformly carrying out of reaction, and the insulation persistent period is 3 hours, after having reacted
Mixed material squeezes into tower bottom of rectifying tower；
(3) rectification: under vacuum conditions, be slowly heated this tower bottoms, tower reactor state 100～120 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 60 DEG C ,-0.95Mpa-0.92Mpa, carry out under conditions of reflux ratio 1:2～1:1
Rectification；Water and acetal mixt is taken out by rectification；
(4) secondary rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:1～the condition of 1:9
Under carry out rectification；Dipropylene glycol methyl ether and acetal mixt is taken out by rectification；Contain according to propylene glycol per hour during extraction
Amount is compared, and content of propylene glycol is less than being switched to product after 0.1%；
(5) three rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:9～the condition of 1:1
Under carry out rectification；Dipropylene glycol methyl ether product is taken out by rectification；Tower top temperature more than 130 DEG C after stop extraction, residual liquid barrel filling
Process；Finally, repeating can be by some component of gas chromatographic detection in the tower bottoms after step (1) detects and calculate rectification
Mass fraction；
(6) Product checking analysis: with the highly polar capillary chromatographic column of FFAP, analyze prepared dipropylene glycol on gas chromatograph
Methyl ether, takes 100 mL dipropylene glycol methyl ethers respectively, measures four kinds of isomerisms of dipropylene glycol methyl ether with the special purpose device surveying boiling range
Weight mark sum.
Further, described step (1) use karl Fischer Moisture Meter measure water in the tower bottoms of propylene glycol monomethyl ether
Mass fraction；Use the mass fraction of Feldalat NM in the volumetric determination tower bottoms of acid base titration；Use the highly polar hair of FFAP
Capillary chromatographic column analyzes the area percentage of the component that can be detected by chromatograph in tower bottoms on gas chromatograph, is multiplied by (1-water
The mass fraction of mass fraction-Feldalat NM) after, obtaining this batch of crude product can be divided by the quality of some components of gas chromatographic detection
Number.
Further, described step (2) mixes addition is propylene glycol in tower bottoms 1.2 times of aldehydes waste liquid.
Further, four kinds of isomers mass fraction sums of described dipropylene glycol methyl ether can reach 99.5% with
On.
It is an advantage of the current invention that:
(1) the dipropylene glycol methyl ether crude product of employing propylene glycol manufacturing enterprise is as raw material, by method of purification of the present invention, permissible
It is greatly improved product quality, it is ensured that the manufacture of quality product；Therefore, it is possible to dipropylene glycol methyl ether is purified out the aqueous for downstream
The enterprises such as latex, plasticizer, coating, ink and abluent in the urgent need to the environmentally friendly solvent such as high-purity dipropylene glycol methyl ether；
(2) owing to no longer passing through repeatedly directly rectification and purification product at dipropylene glycol methyl ether, but dipropyl under sulfuric acid catalysis, is carried out
Glycol methyl ether crude product and the aldolisation of the formalin of excess, react the propylene glycol in crude product and generate cyclic ketal structure, protect
Demonstrate,prove the propylene glycol that can disposably remove in product in distillation process；The by-product boiling point simultaneously generated is relatively low, is conducive to
Directly rectification is taken out, and greatly reduces energy consumption；
(3) use by carrying out dipropylene glycol methyl ether crude product and the aldolisation of excessive formalin under sulfuric acid catalysis, and
Carry out rectification separation under negative pressure and can avoid owing under high temperature, dipropylene glycol methyl ether reacts further, generate high boiling point and mix ether and tie
Jiao is brought to equipped with in the rectifying column of filler with steam, it is to avoid blocking rectifying column；
(4) aldolisation of the formalin carrying out dipropylene glycol methyl ether crude product and excess under sulfuric acid catalysis, formaldehyde used are used
Solution is Products by-product, it is possible to effectively reduces the by-product total amount in producing, greatly reduces environmental protection pressure, be achieved in that
The safety and environmental protection of whole technical process produces.
Detailed description of the invention
A kind of method purifying dimethyl ether, with dipropylene glycol methyl ether crude product as raw material, first at sulfuric acid catalysis
Under carry out the aldolisation of formalin of dipropylene glycol methyl ether crude product and excess；Then negative pressure rectification is carried out after having reacted,
Finally the solution after rectification is collected respectively according to composition difference.
The following examples can make professional and technical personnel that the present invention is more fully understood, but the most therefore by this
Bright it is limited among described scope of embodiments.
Embodiment
A kind of new method producing dipropylene glycol methyl ether, step includes:
(1) tower bottoms component analysis: the sulfuric acid catalyst tentatively deviate from will be completed and heavy constituent dipropylene glycol methyl ether squeezes into reaction
Still, measures mass fraction and the mass fraction of Feldalat NM of water in tower bottoms, and then detecting and calculate can be by gas in tower bottoms
The mass fraction of some components of phase chromatograph detection；Certain batch of dipropylene glycol first being used as raw material is measured by karl Fischer Moisture Meter
The mass fraction of ether crude product is 95%, with the mass fraction of the propylene glycol in the volumetric determination tower bottoms of acid base titration is
2.50%, on gas chromatograph, the component that can be detected by chromatograph in tower bottoms is analyzed with the highly polar capillary chromatographic column of FFAP
Area percentage, after being multiplied by (mass fraction of the mass fraction-Feldalat NM of 1-water), obtaining this batch of tower bottoms can be by gas chromatogram
The mass fraction of some components of detection
Propylene glycol monomethyl ether 0.02%
The different methyl ether of propylene glycol 0.03%
Dipropylene glycol methyl ether 95.3%
Propylene glycol 2.52%
Other impurity 2.13%；
(2) aldehyde reaction: (propylene glycol 2500KG, mixing aldehydes gives up to add mixing aldehydes waste liquid in dipropylene glycol methyl ether crude product
Liquid 150KG), sulphuric acid 1KG；It is then heated to 90 DEG C and is stirred ensureing that uniformly carrying out of reaction, insulation persistent period are 3 little
Time about, react rear mixed material and squeezed into tower bottom of rectifying tower；
(3) rectification: under vacuum conditions, be slowly heated this tower bottoms, tower reactor state 100～120 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 60 DEG C ,-0.95Mpa-0.92Mpa, carry out under conditions of reflux ratio 1:2～1:1
Rectification；Water and acetal mixt 130KG is taken out by rectification；
(4) secondary rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:1～the condition of 1:9
Under carry out rectification；Dipropylene glycol methyl ether and acetal mixt 310KG (chromatography DPM content 60%, acetal is taken out by rectification
Content is 25%, other impurity 15%)；Comparing according to content of propylene glycol per hour during extraction, content of propylene glycol is less than
Product it is switched to after 0.1%；
(5) three rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:9～the condition of 1:1
Under carry out rectification；Dipropylene glycol methyl ether product 1600KG is taken out by rectification；Tower top temperature more than 140 DEG C after stop extraction, residual
Liquid barrel filling processes；Finally, analyze in tower bottoms on gas chromatograph with the highly polar capillary chromatographic column of FFAP after completing rectification
The area percentage of the component that can be detected by chromatograph, after being multiplied by (mass fraction of the mass fraction-Feldalat NM of 1-water), is somebody's turn to do
Criticizing finished product can be by the mass fraction of some components of gas chromatographic detection；
(6) Product checking analysis: with the highly polar capillary chromatographic column of FFAP, analyze prepared dipropylene glycol on gas chromatograph
Methyl ether, takes 100 mL dipropylene glycol methyl ethers respectively, measures four kinds of isomerisms of dipropylene glycol methyl ether with the special purpose device surveying boiling range
Weight mark sum.
The dipropylene glycol methyl ether boiling range that the present embodiment prepares meets the requirements, through gas chromatographic analysis, dipropylene glycol first
Four kinds of isomers mass fraction sums of ether can reach 99.5%, can meet downstream water based emulsion, plasticizer, coating,
Ink and the use requirement to high-purity dipropylene glycol methyl ether and subsequent product thereof of the abluent industry.
The ultimate principle of the present invention and principal character and advantages of the present invention have more than been shown and described.The skill of the industry
The art personnel simply explanation it should be appreciated that the present invention is not restricted to the described embodiments, described in above-described embodiment and description
The principle of the present invention, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, these
Changes and improvements both fall within scope of the claimed invention.Claimed scope by appending claims and
Its equivalent defines.
Claims (5)
1. the method purifying dimethyl ether, it is characterised in that: with dipropylene glycol methyl ether crude product as raw material, first exist
The aldolisation of dipropylene glycol methyl ether crude product and the mixing aldehydes waste liquid of excess is carried out, by the propylene glycol in crude product under sulfuric acid catalysis
Reaction generates cyclic ketal structure；Then negative pressure rectification is carried out after having reacted, finally that the solution after rectification is different according to composition
Collect respectively.
The method of purification dimethyl ether the most according to claim 1, it is characterised in that: described method concrete steps
As follows:
(1) tower bottoms component analysis: the sulfuric acid catalyst tentatively deviate from will be completed and heavy constituent dipropylene glycol methyl ether squeezes into reaction
Still, measures mass fraction and the mass fraction of Feldalat NM of water in tower bottoms, and then detecting and calculate can be by gas in tower bottoms
The mass fraction of some components of phase chromatograph detection, can be included the third two by some components of gas chromatographic detection in described tower bottoms
The different methyl ether of alcohol methyl ether, propylene glycol, dipropylene glycol methyl ether, propylene glycol and other impurity；
(2) aldolisation: the mixing aldehydes waste liquid and the mass ratio that add excess in dipropylene glycol methyl ether crude product are the sulfur of 0.2%
Acid, is then heated to 90 DEG C and is stirred ensureing uniformly carrying out of reaction, and the insulation persistent period is 3 hours, after having reacted
Mixed material squeezes into tower bottom of rectifying tower；
(3) rectification: under vacuum conditions, be slowly heated this tower bottoms, tower reactor state 100～120 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 60 DEG C ,-0.95Mpa-0.92Mpa, carry out under conditions of reflux ratio 1:2～1:1
Rectification；Water and acetal mixt is taken out by rectification；
(4) secondary rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:1～the condition of 1:9
Under carry out rectification；Dipropylene glycol methyl ether and acetal mixt is taken out by rectification；Contain according to propylene glycol per hour during extraction
Amount is compared, and content of propylene glycol is less than being switched to product after 0.1%；
(5) three rectification: under vacuum conditions, this tower bottoms of continuous heating, tower reactor state 140～150 DEG C ,-
0.95Mpa-0.90Mpa, tower top state 120～140 DEG C ,-0.95Mpa-0.92Mpa, reflux ratio 1:9～the condition of 1:1
Under carry out rectification；Dipropylene glycol methyl ether product is taken out by rectification；Tower top temperature more than 130 DEG C after stop extraction, residual liquid barrel filling
Process；Finally, repeating can be by some component of gas chromatographic detection in the tower bottoms after step (1) detects and calculate rectification
Mass fraction；
(6) Product checking analysis: with the highly polar capillary chromatographic column of FFAP, analyze prepared dipropylene glycol on gas chromatograph
Methyl ether, takes 100 mL dipropylene glycol methyl ethers respectively, measures four kinds of isomerisms of dipropylene glycol methyl ether with the special purpose device surveying boiling range
Weight mark sum.
The method of purification dimethyl ether the most according to claim 2, it is characterised in that: described step is adopted in (1)
The mass fraction of water in the tower bottoms of propylene glycol monomethyl ether is measured by karl Fischer Moisture Meter；The volumetric method using acid base titration is surveyed
Determine the mass fraction of Feldalat NM in tower bottoms；The highly polar capillary chromatographic column of FFAP is used to analyze tower bottoms on gas chromatograph
In the area percentage of component that can be detected by chromatograph, after being multiplied by (mass fraction of the mass fraction-Feldalat NM of 1-water), obtain
This batch of crude product can be by the mass fraction of some components of gas chromatographic detection.
The method of purification dimethyl ether the most according to claim 2, it is characterised in that: mixed in described step (2)
Close aldehydes waste liquid addition is propylene glycol in tower bottoms 1.2 times.
The method of purification dimethyl ether the most according to claim 2, it is characterised in that: described dipropylene glycol methyl ether
Four kinds of isomers mass fraction sums can reach more than 99.5%.
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| CN201610336673.3A CN106008177A (en) | 2016-05-20 | 2016-05-20 | Method of purifying dipropylene glycol dimethyl ether |
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| CN201610336673.3A CN106008177A (en) | 2016-05-20 | 2016-05-20 | Method of purifying dipropylene glycol dimethyl ether |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866386A (en) * | 2017-03-08 | 2017-06-20 | 南京师范大学 | A kind of method for removing low boiling impurity in polypropylene glycol monomethyl ether |
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| CN101497556A (en) * | 2009-01-20 | 2009-08-05 | 东南大学 | Method for separating and extracting 1,3-propanediol by solid superacid catalyst reaction |
| CN101717327A (en) * | 2009-12-07 | 2010-06-02 | 无锡百川化工股份有限公司 | Method for producing propylene glycol mono-methyl ether with energy conservation |
| CN104211584A (en) * | 2014-09-10 | 2014-12-17 | 百川化工(如皋)有限公司 | Method for preparing dipropylene glycol methyl ether |
| CN105152874A (en) * | 2015-07-23 | 2015-12-16 | 百川化工(如皋)有限公司 | Method for producing dipropylene glycol methylether |
-
2016
- 2016-05-20 CN CN201610336673.3A patent/CN106008177A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101497556A (en) * | 2009-01-20 | 2009-08-05 | 东南大学 | Method for separating and extracting 1,3-propanediol by solid superacid catalyst reaction |
| CN101717327A (en) * | 2009-12-07 | 2010-06-02 | 无锡百川化工股份有限公司 | Method for producing propylene glycol mono-methyl ether with energy conservation |
| CN104211584A (en) * | 2014-09-10 | 2014-12-17 | 百川化工(如皋)有限公司 | Method for preparing dipropylene glycol methyl ether |
| CN105152874A (en) * | 2015-07-23 | 2015-12-16 | 百川化工(如皋)有限公司 | Method for producing dipropylene glycol methylether |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866386A (en) * | 2017-03-08 | 2017-06-20 | 南京师范大学 | A kind of method for removing low boiling impurity in polypropylene glycol monomethyl ether |
| CN106866386B (en) * | 2017-03-08 | 2020-04-21 | 南京师范大学 | Method for removing low-boiling-point impurities in polypropylene glycol monomethyl ether |
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Application publication date: 20161012 |