CN104892371B - A kind of preparation method of glycol dimethyl ether - Google Patents
A kind of preparation method of glycol dimethyl ether Download PDFInfo
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- CN104892371B CN104892371B CN201510246776.6A CN201510246776A CN104892371B CN 104892371 B CN104892371 B CN 104892371B CN 201510246776 A CN201510246776 A CN 201510246776A CN 104892371 B CN104892371 B CN 104892371B
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- Prior art keywords
- glycol monoethyl
- monoethyl ether
- ether
- glycol
- sodium chloride
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 42
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 27
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000011780 sodium chloride Substances 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 12
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 11
- 239000011734 sodium Substances 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 239000012266 salt solution Substances 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims abstract description 4
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical group O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012065 filter cake Substances 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 abstract description 22
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 238000003756 stirring Methods 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 8
- -1 ethers organic compound Chemical class 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 238000009423 ventilation Methods 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 3
- 230000003519 ventilatory effect Effects 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003385 sodium Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IXCZEYQFCLQBNN-UHFFFAOYSA-N COC.[Na] Chemical compound COC.[Na] IXCZEYQFCLQBNN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000008282 halocarbons 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
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 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 kind of preparation method of glycol dimethyl ether, belongs to ethers organic compound synthesis technical field.This method adds a certain amount of glycol monoethyl ether in a kettle first, then a certain amount of alkali is put into glycol monoethyl ether and is stirred for the first time, reacting liquid temperature is cooled to 15~20 DEG C, put into a certain amount of alkali for the second time again and reaction system is cooled after stirring, reacting liquid temperature is controlled at 25~30 DEG C, reaction generation glycol monoethyl ether sodium salt；Then it is passed through monochloro methane gas into the glycol monoethyl ether sodium salt solution of generation, the sodium chloride crystal for having white slowly separates out, reaction solution is colourless or extremely light light yellow, by reacting liquid filtering, filter cake is clean sodium chloride, filtrate is the ethylene glycol dimethyl ether solution of sodium chloride, filtrate is distilled, efflux is glycol dinitrate ether product.The inventive method can obtain the higher byproduct sodium chloride of purity simultaneously, and realize the clean manufacturing of glycol dimethyl ether.
Description
Technical field
The invention belongs to ethers organic compound synthesis technical field, and in particular to a kind of preparation side of glycol dimethyl ether
Method.
Background technology
Glycol dimethyl ether is a kind of colourless neutral liquid for having ethers smell, when boiling point is 83 DEG C, 25 DEG C at ambient pressure
Density is 0.87g/cm3, its chemical property is highly stable, is often used as aprotic polar solvent, can dissolve various resins and fibre
Dimension element, can also be miscible with arbitrary proportion with water, alcohol, hydrocarbon, ether, ester, ketone etc..
At present, the industrial process of glycol dimethyl ether is mainly Williamson synthetic methods, and halogenated hydrocarbons selects chloromethane
Alkane, in order to reduce production cost, industrial is typically raw material using caustic soda, but the method can produce more by-product
Thing increases energy consumption, it is necessary to substantial amounts of organic media.Chinese patent 1142482A reports to be synthesized by methylating agent of chloromethanes
Glycol dimethyl ether method, this method makes it act on forming second two with piece alkali first using glycol monoethyl ether as initiation material
Alcohol monomethyl ether sodium salt, then methyl chloride gas is passed through into the sodium salt solution, reaction solution distillation finally can be obtained into glycol dimethyl ether
Product and sodium chloride byproduct.In conventional methods where, because reaction condition controls bad or process design unreasonable, chlorination
Bronzing would generally be presented in sodium byproduct, and the decolorization of sodium chloride is complex, can also greatly increase production cost, finally
The economic value of sodium chloride is lost substantially.Because side product chlorinated sodium can not be a kind of extremely unreasonable effective for industrialization
Production technology, let alone clean manufacturing.It is not inconsistent with the relevant law ＆ policy of country, thus by the industry of glycol dimethyl ether
It is trend of the times that production, which switchs to clean manufacturing,.
In the traditional processing technology of glycol dimethyl ether, by-product is caused due to the impurity that raw material ethylene glycol monomethyl ether is brought
Thing sodium chloride is easily contaminated and sends out technical problem russet, it is necessary to change from the angle of production technology to conventional method
Enter, get hold of the opportunity of charging, control reaction temperature, the clean manufacturing of final achievable glycol dimethyl ether.
The content of the invention
A kind of technical problem present in traditional processing technology of the present invention for existing glycol dimethyl ether, there is provided second two
The clean method for preparing of diethylene glycol dimethyl ether；In the inventive method, while the higher byproduct sodium chloride of purity is obtained, and make its tool
There is the economic benefit of maximum；The inventive method makes full use of the caused heat of reaction itself, saves production process to greatest extent
In energy consumption.Make the production technology of glycol dimethyl ether turn into cycle production process, so as to realize the cleaning of glycol dimethyl ether
Production.
The preparation method of glycol dimethyl ether provided by the present invention comprises the following steps that：
(1) a certain amount of glycol monoethyl ether is added in a kettle, is then put into for the first time into glycol monoethyl ether
A certain amount of alkali, and be stirred, reacting liquid temperature is then cooled to 15 DEG C~20 DEG C, then for the second time to ethylene glycol list first
A certain amount of alkali is put into ether, reaction system is cooled after being sufficiently stirred, reacting liquid temperature is controlled at 25 DEG C~30 DEG C, instead
Answer the glycol monoethyl ether and sodium hydroxide reaction generation glycol monoethyl ether sodium salt in kettle；The glycol monoethyl ether and hydrogen-oxygen
The mol ratio for changing sodium is 1:0.5, the piece alkali number that the first time puts into glycol monoethyl ether is with described for the second time to second two
The piece alkali number put into alcohol monomethyl ether is identical.
(2) monochloro methane gas is passed through in the glycol monoethyl ether sodium salt solution of generation into the step (1), keeps anti-
It is 0.05MPa~0.5MPa to answer pressure in kettle, and controls temperature of reaction system to be continuously passed through monochloro methane gas at 70 DEG C~75 DEG C
Body 8 hours, along with being passed through for monochloro methane gas, the sodium chloride crystal for having white slowly separates out, until reaction terminates, instead
It is colourless or extremely light light yellow to answer liquid, will not become bronzing.
(3) reacting liquid filtering for obtaining above-mentioned steps (2), filter cake are clean sodium chloride, and filtrate is the second of sodium chloride
Glycol dimethyl ether solution, filtrate is distilled, and efflux is glycol dinitrate ether product, and residual solid is sodium chloride crude product.
Chemical equation involved in the present invention is as follows：
The present invention has following technical characterstic：
(1) in charging, by adjusting controlling reaction temperature reaction process, it so not only can guarantee that each component suitable
Under conditions of fully react, moreover it is possible to reduce the generation of side reaction, so as to improve raw material availability, reduce the waste of raw material.
(2) when piece alkali is added into glycol monoethyl ether, distribution is gradually added into, and can so ensure the thing added every time
Material is reacted away quickly, will not produce the sedimentation caking phenomenon of high-volume solid.If conversely, disposably fed intake to piece alkali,
It is easy to cause the accumulation of a large amount of piece alkali for having not enough time to reaction, the contact area between reactant reduces, and reaction carries out slow；
And substantial amounts of heat is had after input piece alkali and is released, if whole reaction system heat exchange is uneven, hot-spot can be caused, therewith
More side reaction can be produced to occur, some security incidents are there is also when serious.
(3) when being passed through monochloro methane into glycol monoethyl ether sodium salt solution, cooling measure is taken, side reaction hair can be reduced
It is raw.Because glycol monoethyl ether sodium salt and monochloro methane reaction are exothermic reactions, glycol monoethyl ether sodium salt holds very much at high temperature
Side reaction easily occurs and forms accessory substance, accessory substance is yellow or Red viscous transparency liquid, and property is relatively stable, with the overwhelming majority
Organic matter intermiscibility is good, so, the side product chlorinated sodium of generation is easy to contaminated and carries red." control of the present invention
Temperature of reaction system processed is at 70~75 DEG C " this side reaction can be avoided to occur, therefore the sodium chloride quality of generation can be made more preferable, slightly
Processing can be used as sterling sale, can not only substantially reduce production cost, can also bring more preferable economic benefit.
Brief description of the drawings
Fig. 1 is the process flow diagram of preparation method of the present invention.
Embodiment
Embodiment 1：
1Kg glycol monoethyl ether liquid is put into a kettle, then while stirring to input 0.263Kg inside reactor
Piece alkali, while the cooling water of reactor is opened, control reactor temperature is at 18~19 DEG C, when piece alkali solid is wholly absent,
Piece alkali 0.263Kg is added again, continues to stir, while controls reactor temperature in the range of 27~29 DEG C, treats piece alkali whole
Continue stirring 20 minutes during disappearance, each component is fully reacted.Then, monochloro methane gas is slowly introducing into reactor, is protected
It is 0.05~0.5MPa to hold reacting kettle inner pressure, is released due to having big calorimetric in ventilatory response, need to open big condensed water, is made anti-
Kettle internal temperature is answered to be maintained at 70~75 DEG C, duration of ventilation is 8 hours.After ventilation terminates, mixed liquor is distilled, distillate
For diethylene glycol dimethyl ether liquid, weigh 1.02Kg, yield 86.4%, and residual solid is colourless sodium chloride crystal, is weighed
0.670Kg。
Embodiment 2：
1.7Kg glycol monoethyl ether liquid is put into a kettle, then while stirring to input inside reactor
0.447Kg piece alkali, while the cooling water of reactor is opened, control reactor temperature treats that piece alkali solid is wholly absent at 18 DEG C
When, piece alkali 0.447Kg is added again, continues to stir, while reactor temperature is controlled in the range of 27~28 DEG C, treat that piece alkali is complete
Portion continues stirring 25 minutes when disappearing, each component is fully reacted.Then, monochloro methane gas is slowly introducing into reactor,
Holding reacting kettle inner pressure is 0.05~0.5MPa, is released due to having big calorimetric in ventilatory response, need to open big condensed water, make
Reactor internal temperature is maintained at 74~75 DEG C, and duration of ventilation is 8 hours.After ventilation terminates, mixed liquor is distilled, distillated
Thing is diethylene glycol dimethyl ether liquid, and weigh 1.79Kg, yield 89.1%, and residual solid is colourless sodium chloride crystal, is weighed
1.160Kg。
Embodiment 3：
2.3Kg glycol monoethyl ether liquid is put into a kettle, then while stirring to input inside reactor
0.605Kg piece alkali, while the cooling water of reactor is opened, control reactor temperature treats that piece alkali solid is complete near 18 DEG C
During disappearance, piece alkali 0.605Kg is added again, continues to stir, while control reactor temperature to treat piece in the range of 27~28 DEG C
Alkali continues stirring 30 minutes when all disappearing, each component is fully reacted.Then, monochloro methane gas is slowly introducing into reactor
Body, holding reacting kettle inner pressure are 0.05~0.5MPa, are released due to having big calorimetric in ventilatory response, need to open big condensation
Water, reactor internal temperature is set to be maintained at 73~75 DEG C, duration of ventilation is 8 hours.After ventilation terminates, mixed liquor is steamed
Evaporate, distillate is diethylene glycol dimethyl ether liquid, and weigh 2.375Kg, yield 87.2%, and residual solid is brilliant for colourless sodium chloride
Body, weigh 1.541Kg.
Claims (1)
1. a kind of preparation method of glycol dimethyl ether, it is characterised in that this method comprises the following steps that：
（1）A certain amount of glycol monoethyl ether is added in a kettle, is then put into for the first time into the glycol monoethyl ether
A certain amount of sodium hydroxide, and be stirred, reacting liquid temperature is then cooled to 15 DEG C~20 DEG C, then for the second time to ethylene glycol
A certain amount of sodium hydroxide is put into monomethyl ether, reaction system is cooled after being sufficiently stirred, reacting liquid temperature is controlled at 25 DEG C
~30 DEG C, glycol monoethyl ether and sodium hydroxide reaction generation glycol monoethyl ether sodium salt in the reactor；The second two
The mol ratio of alcohol monomethyl ether and sodium hydroxide is 1:0.5, the amount of sodium hydroxide that the first time puts into glycol monoethyl ether
It is identical with the amount of sodium hydroxide that described second puts into glycol monoethyl ether；
（2）To the step（1）Monochloro methane gas is passed through in the glycol monoethyl ether sodium salt solution of middle generation, keeps described anti-
It is 0.05 MPa~0.5MPa to answer pressure in kettle, and controls temperature of reaction system to be continuously passed through monochloro methane at 70 DEG C~75 DEG C
Gas 8 hours, along with being passed through for monochloro methane gas, the sodium chloride crystal for having white slowly separates out, until reaction terminates；
（3）By the step（2）Obtained reacting liquid filtering, filter cake are clean sodium chloride, and filtrate is the ethylene glycol of sodium chloride
Dimethyl ether solution, filtrate is distilled, efflux is glycol dinitrate ether product, and residual solid is sodium chloride crude product.
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| 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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| 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 |
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| CN104892371B true CN104892371B (en) | 2018-03-30 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| 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 |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1142482A (en) * | 1996-07-05 | 1997-02-12 | 朱国华 | Production of polyethylene glycol dimethyl ether |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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