CN104892371A - Method for producing glycol dimethyl ether - Google Patents
Method for producing glycol dimethyl ether Download PDFInfo
- Publication number
- CN104892371A CN104892371A CN201510246776.6A CN201510246776A CN104892371A CN 104892371 A CN104892371 A CN 104892371A CN 201510246776 A CN201510246776 A CN 201510246776A CN 104892371 A CN104892371 A CN 104892371A
- Authority
- CN
- China
- Prior art keywords
- ethylene glycol
- glycol monomethyl
- monomethyl ether
- sodium
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title abstract description 16
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 28
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- KYOYGCKMMSFSNW-UHFFFAOYSA-N [Na].COCCO Chemical compound [Na].COCCO KYOYGCKMMSFSNW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 239000012266 salt solution Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 239000012065 filter cake Substances 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 16
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 5
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 10
- 235000011121 sodium hydroxide Nutrition 0.000 abstract description 5
- 229940050176 methyl chloride Drugs 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- -1 ether organic compound Chemical class 0.000 abstract description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 238000005273 aeration Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 150000003385 sodium Chemical class 0.000 description 3
- 238000009423 ventilation Methods 0.000 description 3
- 230000003519 ventilatory effect Effects 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/04—Chlorides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a method for producing glycol dimethyl ether, and belongs to the technical field of ether organic compound synthesis. The method is as below: first adding a certain amount of ethylene glycol monomethyl ether to a reaction kettle, adding for the first time a certain amount of in the ethylene glycol monomethyl ether caustic soda and stirring; cooling the reaction solution temperature to 15-20 DEG C; adding a certain amount of caustic soda for the second time and stirring; cool the reaction system, and controlling the temperature of the reaction solution at 25-30 DEG C; reacting to form ethylene glycol monomethyl ether sodium salt; introducing methyl chloride gas to the ethylene glycol monomethyl ether sodium salt solution to precipitate white sodium salt crystals slowly, wherein the reaction liquid is a colorless or very light pale yellow; filtering the reaction liquid to obtain a filter cake of clean sodium chloride and a filtrate of an ethylene glycol dimethyl ether solution of sodium chloride; and distilling the filtrate to obtain an effluent of glycol dimethyl ether product. The method of the present invention can obtain high purity by-product sodium chloride, and realize clean production of glycol dimethyl ether.
Description
Technical field
The invention belongs to ethers organic compound synthesis technical field, be specifically related to a kind of preparation method of glycol dimethyl ether.
Background technology
Glycol dimethyl ether is a kind of colourless neutral liquid having ethers smell, and boiling point is 83 DEG C at ambient pressure, and when 25 DEG C, density is 0.87g/cm
3, its chemical property is highly stable, is often used as aprotic polar solvent, can dissolve various resin and Mierocrystalline cellulose, also can be miscible with arbitrary proportion with water, alcohol, hydrocarbon, ether, ester, ketone etc.
At present, the industrial process mainly Williamson synthesis method of glycol dimethyl ether, methyl chloride selected by halohydrocarbon, in order to reduce production cost, industrial general use caustic soda is raw material, but this method can produce more by product, need a large amount of organic mediums, increase energy consumption.It is the glycol dimethyl ether method that methylating agent synthesizes that Chinese patent 1142482A reports with methyl chloride, the method take ethylene glycol monomethyl ether as starting raw material, first itself and the effect of sheet alkali is made to form ethylene glycol monomethyl ether sodium salt, in this sodium salt solution, pass into methyl chloride gas again, finally reaction solution distillation can be obtained glycol dinitrate ether product and sodium chloride byproduct.In conventional methods where; because reaction conditions control is bad or process design is unreasonable, sodium-chlor byproduct can present sorrel usually, and the desolventing technology of sodium-chlor is comparatively complicated; also greatly can increase production cost, the economic worth of final sodium-chlor is lost substantially.Because side product chlorinated sodium can not be effective to industrialization, be the very irrational production technique of one, let alone cleaner production.Be not inconsistent with the regulations policy of country, thus transferring the industrial production of glycol dimethyl ether to cleaner production is trend of the times.
In the traditional processing technology of glycol dimethyl ether, the impurity brought due to raw material ethylene glycol monomethyl ether and cause side product chlorinated sodium easily contaminated and send out technical problem russet, need to improve from the angle of production technique traditional method, get hold of reinforced opportunity, control temperature of reaction well, finally can realize the cleaner production of glycol dimethyl ether.
Summary of the invention
The present invention is directed to the technical problem existed in the traditional processing technology of existing glycol dimethyl ether, a kind of clean method for preparing of glycol dimethyl ether is provided; In this inventive method, obtain the higher byproduct sodium-chlor of purity simultaneously, and make it have maximum economic benefit; The inventive method makes full use of the heat that reaction self produces, and saves the energy consumption in production process to greatest extent.Make the production technique of glycol dimethyl ether become cycle production process, thus realize the cleaner production of glycol dimethyl ether.
Preparation method's concrete steps of glycol dimethyl ether provided by the present invention are as follows:
(1) a certain amount of ethylene glycol monomethyl ether is added in a kettle., then first time drops into a certain amount of alkali in ethylene glycol monomethyl ether, and stir, then reacting liquid temperature is cooled to 15 DEG C ~ 20 DEG C, second time drops into a certain amount of alkali in ethylene glycol monomethyl ether again, to reaction system cooling after abundant stirring, controlled by reacting liquid temperature at 25 DEG C ~ 30 DEG C, the ethylene glycol monomethyl ether in reactor and sodium hydroxide react generating glycol monomethyl ether sodium salt; The mol ratio of described ethylene glycol monomethyl ether and sodium hydroxide is 1:0.5, and the sheet alkali number that described first time drops in ethylene glycol monomethyl ether is identical with the sheet alkali number that described second time drops in ethylene glycol monomethyl ether.
(2) monochloro methane gas is passed in the ethylene glycol monomethyl ether sodium salt solution generated in described step (1), maintenance reacting kettle inner pressure is 0.05MPa ~ 0.5MPa, and control temperature of reaction system at 70 DEG C ~ 75 DEG C, pass into monochloro methane gas continuously 8 hours, along with passing into of monochloro methane gas, the sodium chloride crystal of meeting adularescent is slowly separated out, until reaction terminates, reaction solution is colourless or extremely light light yellow, and can not redden brown.
(3) by reacting liquid filtering that above-mentioned steps (2) obtains, filter cake is clean sodium-chlor, and filtrate is the ethylene glycol dimethyl ether solution of sodium-chlor, filtrate is distilled, effluent liquid is glycol dinitrate ether product, and residual solid is sodium-chlor crude product.
Chemical equation involved in the present invention is as follows:
The present invention has following technical characterstic:
(1) when reinforced, by regulating controlling reaction temperature reaction process, can not only ensure that each component is fully reacted under suitable conditions, can also reduce the generation of side reaction, thus improve raw material availability like this, reducing the waste of raw material.
(2) when adding sheet alkali in ethylene glycol monomethyl ether, distribute and add gradually, can ensure that the material at every turn added is reacted away very soon like this, the sedimentation caking phenomenon of solid in enormous quantities can not be produced.Otherwise if carry out disposable feeding intake to sheet alkali, be easy to the accumulation causing a large amount of sheet alkali not having enough time to react, the contact area between reactant reduces, and reaction is carried out slowly; And have a large amount of heat release after dropping into sheet alkali, if whole reaction system heat exchange is uneven, can local superheating be caused, more side reaction can be produced thereupon and occur, time serious, also there will be some security incidents.
(3) when passing into monochloro methane in ethylene glycol monomethyl ether sodium salt solution, take cooling measure, side reaction can be reduced and occur.Thermopositive reaction because ethylene glycol monomethyl ether sodium salt and monochloro methane react, at high temperature ethylene glycol monomethyl ether sodium salt is easy to that side reaction occurs and forms by product, by product is yellow or Red viscous transparent liquid, character is comparatively stable, good with most organism intermiscibility, so the side product chlorinated sodium of generation is easy to contaminated and with redness." the controlling temperature of reaction system at 70 ~ 75 DEG C " that the present invention relates to can avoid this side reaction to occur, therefore the sodium-chlor quality of generation can be made better, process a little and namely can be used as sterling sale, not only greatly can reduce production cost, better economic benefit can also be brought.
Accompanying drawing explanation
Fig. 1 is the process flow diagram of preparation method of the present invention.
Embodiment
Embodiment 1:
Drop into 1Kg ethylene glycol monomethyl ether liquid in a kettle., then inside reactor, 0.263Kg sheet alkali is dropped into while stirring, open the water coolant of reactor simultaneously, control reactor temperature at 18 ~ 19 DEG C, when the solid completely dissolve of sheet alkali, again add sheet alkali 0.263Kg, continue to stir, control reactor temperature simultaneously within the scope of 27 ~ 29 DEG C, when sheet alkali all disappears, continue stirring 20 minutes, each component is fully reacted.Then, in reactor, slowly pass into monochloro methane gas, maintenance reacting kettle inner pressure is 0.05 ~ 0.5MPa, heat release in a large number owing to having when ventilatory response, and need open large water of condensation, make reactor internal temperature remain on 70 ~ 75 DEG C, aeration time is 8 hours.After ventilation terminates, distill mixed solution, overhead product is diethylene glycol dimethyl ether liquid, and weigh 1.02Kg, productive rate 86.4%, and residual solid is colourless sodium chloride crystal, and weigh 0.670Kg.
Embodiment 2:
Drop into 1.7Kg ethylene glycol monomethyl ether liquid in a kettle., then inside reactor, 0.447Kg sheet alkali is dropped into while stirring, open the water coolant of reactor simultaneously, control reactor temperature at 18 DEG C, when the solid completely dissolve of sheet alkali, again add sheet alkali 0.447Kg, continue to stir, control reactor temperature simultaneously within the scope of 27 ~ 28 DEG C, when sheet alkali all disappears, continue stirring 25 minutes, each component is fully reacted.Then, in reactor, slowly pass into monochloro methane gas, maintenance reacting kettle inner pressure is 0.05 ~ 0.5MPa, heat release in a large number owing to having when ventilatory response, and need open large water of condensation, make reactor internal temperature remain on 74 ~ 75 DEG C, aeration time is 8 hours.After ventilation terminates, distill mixed solution, overhead product is diethylene glycol dimethyl ether liquid, and weigh 1.79Kg, productive rate 89.1%, and residual solid is colourless sodium chloride crystal, and weigh 1.160Kg.
Embodiment 3:
Drop into 2.3Kg ethylene glycol monomethyl ether liquid in a kettle., then inside reactor, 0.605Kg sheet alkali is dropped into while stirring, open the water coolant of reactor simultaneously, control reactor temperature near 18 DEG C, when the solid completely dissolve of sheet alkali, again add sheet alkali 0.605Kg, continue to stir, control reactor temperature simultaneously within the scope of 27 ~ 28 DEG C, when sheet alkali all disappears, continue stirring 30 minutes, each component is fully reacted.Then, in reactor, slowly pass into monochloro methane gas, maintenance reacting kettle inner pressure is 0.05 ~ 0.5MPa, heat release in a large number owing to having when ventilatory response, and need open large water of condensation, make reactor internal temperature remain on 73 ~ 75 DEG C, aeration time is 8 hours.After ventilation terminates, distill mixed solution, overhead product is diethylene glycol dimethyl ether liquid, and weigh 2.375Kg, productive rate 87.2%, and residual solid is colourless sodium chloride crystal, and weigh 1.541Kg.
Claims (1)
1. a preparation method for glycol dimethyl ether, is characterized in that the method concrete steps are as follows:
(1) a certain amount of ethylene glycol monomethyl ether is added in a kettle., then first time drops into a certain amount of alkali in described ethylene glycol monomethyl ether, and stir, then reacting liquid temperature is cooled to 15 DEG C ~ 20 DEG C, second time drops into a certain amount of alkali in ethylene glycol monomethyl ether again, to reaction system cooling after abundant stirring, controlled by reacting liquid temperature at 25 DEG C ~ 30 DEG C, the ethylene glycol monomethyl ether in described reactor and sodium hydroxide react generating glycol monomethyl ether sodium salt; The mol ratio of described ethylene glycol monomethyl ether and sodium hydroxide is 1:0.5, and the sheet alkali number that described first time drops in ethylene glycol monomethyl ether is identical with the sheet alkali number that described second time drops in ethylene glycol monomethyl ether;
(2) monochloro methane gas is passed in the ethylene glycol monomethyl ether sodium salt solution generated in described step (1), described reacting kettle inner pressure is kept to be 0.05MPa ~ 0.5MPa, and control temperature of reaction system at 70 DEG C ~ 75 DEG C, pass into monochloro methane gas continuously 8 hours, along with passing into of monochloro methane gas, the sodium chloride crystal of meeting adularescent is slowly separated out, until reaction terminates;
(3) by reacting liquid filtering that described step (2) obtains, filter cake is clean sodium-chlor, and filtrate is the ethylene glycol dimethyl ether solution of sodium-chlor, filtrate is distilled, effluent liquid is glycol dinitrate ether product, and residual solid is sodium-chlor crude product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510246776.6A CN104892371B (en) | 2015-05-14 | 2015-05-14 | A kind of preparation method of glycol dimethyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510246776.6A CN104892371B (en) | 2015-05-14 | 2015-05-14 | A kind of preparation method of glycol dimethyl ether |
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| Publication Number | Publication Date |
|---|---|
| CN104892371A true CN104892371A (en) | 2015-09-09 |
| CN104892371B CN104892371B (en) | 2018-03-30 |
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|---|---|---|---|
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| Country | Link |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110183313A (en) * | 2019-06-27 | 2019-08-30 | 河北迈太特化工有限公司 | A kind of preparation method of diethylene glycol dimethyl ether |
| CN112246279A (en) * | 2020-07-09 | 2021-01-22 | 上海芾楠企业服务中心 | Catalyst and preparation method of ethylene glycol dimethyl ether |
| CN112624910A (en) * | 2021-01-13 | 2021-04-09 | 河南红东方化工股份有限公司 | Production method of diethylene glycol dimethyl ether |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1142482A (en) * | 1996-07-05 | 1997-02-12 | 朱国华 | Production of polyethylene glycol dimethyl ether |
-
2015
- 2015-05-14 CN CN201510246776.6A patent/CN104892371B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1142482A (en) * | 1996-07-05 | 1997-02-12 | 朱国华 | Production of polyethylene glycol dimethyl ether |
Non-Patent Citations (1)
| Title |
|---|
| 芮培欣等: "Williamson反应合成二乙二醇二甲醚及其合成条件优化", 《江西化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110183313A (en) * | 2019-06-27 | 2019-08-30 | 河北迈太特化工有限公司 | A kind of preparation method of diethylene glycol dimethyl ether |
| CN112246279A (en) * | 2020-07-09 | 2021-01-22 | 上海芾楠企业服务中心 | Catalyst and preparation method of ethylene glycol dimethyl ether |
| CN112246279B (en) * | 2020-07-09 | 2021-10-01 | 上海芾楠企业服务中心 | Catalyst and preparation method of ethylene glycol dimethyl ether |
| CN112624910A (en) * | 2021-01-13 | 2021-04-09 | 河南红东方化工股份有限公司 | Production method of diethylene glycol dimethyl ether |
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| Publication number | Publication date |
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| CN104892371B (en) | 2018-03-30 |
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