CN110511125A - A method of polymethoxy dimethyl ether is synthesized using sulfuric acid type eutectic solvent - Google Patents
A method of polymethoxy dimethyl ether is synthesized using sulfuric acid type eutectic solvent Download PDFInfo
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- CN110511125A CN110511125A CN201910896634.2A CN201910896634A CN110511125A CN 110511125 A CN110511125 A CN 110511125A CN 201910896634 A CN201910896634 A CN 201910896634A CN 110511125 A CN110511125 A CN 110511125A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
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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
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention belongs to cetane additive for diesel oil polymethoxy dimethyl ethers to synthesize field, a kind of more particularly to method using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, implement as follows: weighing tetrabutylammonium chloride and sulfuric acid, under conditions of ice bath, sulfuric acid is added dropwise into tetrabutylammonium chloride until forming clear solution, sulfuric acid type eutectic solvent can be obtained；(2) synthesize polymethoxy dimethyl ether process: the amount of trying to please is the autoclave of 100ml, weigh a certain amount of methanol, metaformaldehyde and sulfuric acid type eutectic solvent, nitrogen is poured in a high pressure reaction kettle and carries out synthetic reaction, it is placed into recovery room temperature after reaction, the yield of polymethoxy dimethyl ether is determined using gas-chromatography.In preparation process of the present invention, the synthetic method of used catalyst is simple, is not necessarily to last handling process, substantially reduces the production cost for reducing catalyst.
Description
Technical field
The invention belongs to the synthesis field of diesel cetane-number improver polymethoxy dimethyl ether more particularly to a kind of uses
The method of sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether.
Background technique
Since that there are efficiencies of combustion during burning is lower for diesel oil, combustibility is poor, the tail gas pollution ring of discharge
The problems such as border.Effective method is that cetane number improver is added in diesel oil to improve the combustibility of diesel oil, therefore
The cetane number improver of synthesizing efficient has important practical significance.
Polymethoxy dimethyl ether, also known as PODEn are a kind of polyether compounds of low molecular weight, with higher to contain
Oxygen amount and its Cetane number is higher, a small amount of polymethoxy dimethyl ether is added in diesel oil can effectively improve improvement diesel oil
Combustibility, effectively lower tail gas in pernicious gas discharge, effectively reduce pollution on the environment.Polymethoxy diformazan
The synthesis of ether is usually to be synthesized under the catalytic action of strongly acidic catalyst with raw materials such as methanol, dimethyl ether and paraformaldehydes.
The catalyst of early stage is mostly that corrosive organic acid such as sulfuric acid and trifluoromethanesulfonic acid is catalyst, and the shortcomings that this catalyst is pair
More serious corrosion is caused in the equipment of synthesis polymethoxy dimethyl ether.Chinese Academy of Sciences Lanzhou Chemical Physics research (CN
101962318A, CN 102757323, CN 108299166A) ionic liquid synthesis PODEn has been adopted, yield is close to 50%.On
State the ionic liquid of synthesis although catalytic effect with higher, but the preparation process of ionic liquid is quite born miscellaneous, usually needs
Sulfonic group isoreactivity group is grafted on cation, needs to purify in preparation process to remove impurity, and reaction time
It is longer.
2003, Abbott etc. ABBOTT A P, CAPPER G, DAVIES D L, RASHEED R K,
TAMBYRAJAH V. Novel solvent properties of choline chloride/urea mixtures[J]
.Chem. Commun., 2003: 70-71 ] have found for the first time it is a kind of formed by quaternary ammonium salt and amide compound it is physico
Learn solvent-eutectic solvent of good properties.Eutectic solvent is with the receptor (ammonium of hydrogen bond donor (organic acid, alcohol etc.) and hydrogen bond
Salt, metal chloride etc.) it is that raw material is synthesized by hydrogen bond.The physicochemical properties of eutectic solvent and ionic liquid extremely phase
Seemingly, therefore also it is classified as a kind of novel ion liquid or ionic liquid analog [Wei Lu, Fan Youjun eutectic is molten by someone
Agent and its application study progress [J] chemistry notification, 2011,74(4): 333-339 WEI Lu, FAN You-jun.
Progress of Deep Eutectic Solvents and Their Applications [J]. CHEMISTRY,
2011,74(4): 333-339].This solvent synthesis process is simple and atom utilization is up to 100%, is a kind of novel green
Solvent.Currently, eutectic solvent has caused the extensive attention of countries in the world researcher, and in separation process, chemical reaction, function
Energy material and electrochemistry etc. fields show good application prospect.But just at present, eutectic solvent is not yet applied to gather
The synthesis field of methoxyl group dimethyl ether.
Summary of the invention
The purpose of the present invention is to provide a kind of methods using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether.
Sulfuric acid type eutectic solvent can be used as catalyst in the synthesis of this polymethoxy dimethyl ether, and catalyst can be effectively reduced
Preparation time and production cost, the high income of purpose product are conducive to the industrialization of technique.
In order to solve the above technical problems, the present invention is implemented as follows:
A method of polymethoxy dimethyl ether is synthesized using sulfuric acid type eutectic solvent, is implemented as follows:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, and under conditions of ice bath, sulfuric acid is added dropwise
Into tetrabutylammonium chloride until forming clear solution, sulfuric acid type eutectic solvent can be obtained；
(2) methanol, metaformaldehyde and step (1) the sulfuric acid type eutectic solvent, In the synthesis of polymethoxy dimethyl ether: are taken
It is filled with nitrogen in autoclave and carries out synthetic reaction；It is placed into after reaction and restores room temperature to get the poly- first of purpose product
Oxygroup dimethyl ether.
As a preferred embodiment, in step (1) of the present invention, the molar ratio of the tetrabutylammonium chloride and sulfuric acid is 1:1.
Further, in the step (1) of the present invention, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise to tetrabutyl chlorine
Change in ammonium, 10 min of stirring can form clear solution, and sulfuric acid type eutectic solvent can be obtained.
Further, in step (2) of the present invention, the molar ratio of methanol and metaformaldehyde is 2~3:1~4.
Further, in step (2) of the present invention, synthetic reaction pressure is 0.5~3Mpa.
Further, in step (2) of the present invention, synthesis reaction temperature is 80~150 DEG C.
Further, in step (2) of the present invention, synthesising reacting time is 4~10h.
The structural formula of sulfuric acid type eutectic solvent used in the present invention:
In preparation process of the present invention, all reagents are commercial product, are not necessarily to cumbersome preparation.In preparation process of the present invention, adopted
Catalyst is both catalyst and extractant, to reduce production cost, simplifies synthesis polymethoxy dimethyl ether
Program.In addition, the present invention achieves good balance between raising conversion ratio and enhancing environmental protection efficacy.In this polymethoxy two
Sulfuric acid type eutectic solvent can be used as catalyst in the synthesis of methyl ether, and preparation time and the production of catalyst can be effectively reduced
Cost, the high income of purpose product are conducive to the industrialization of technique.
Detailed description of the invention
Present invention will be further explained below with reference to the attached drawings and specific embodiments.Protection scope of the present invention not only office
It is limited to the statement of following content.
Fig. 1 is the infrared spectrum for the sulfuric acid type eutectic solvent that the present invention synthesizes.
A- sulfuric acid type eutectic solvent in figure, b- tetrabutylammonium chloride, c- sulfuric acid.
Specific embodiment
A method of polymethoxy dimethyl ether being synthesized using sulfuric acid type eutectic solvent, following steps are implemented:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, is being placed with the tetrabutyl under condition of ice bath
Sulfuric acid is added dropwise in the conical flask of ammonium chloride while stirring until mixture formation clear solution, it is low total to can be obtained sulfuric acid type
Molten solvent；
(2) synthesize polymethoxy dimethyl ether process: the amount of trying to please is the autoclave of 100ml, weighs a certain amount of methanol, trimerization
Formaldehyde and sulfuric acid type eutectic solvent, are filled with nitrogen in a high pressure reaction kettle, it is made to maintain certain pressure.In certain temperature
With synthetic reaction is carried out under pressure, be placed into recovery room temperature after reaction, polymethoxy dimethyl ether determined using gas-chromatography
Yield.In the step (1) of the present invention, the molar ratio of tetrabutylammonium chloride and sulfuric acid is 1:1, and reaction temperature is 0 DEG C, sulfuric acid
Adding manner be added dropwise.
In step (2) of the present invention, the molar ratio of methanol and metaformaldehyde additional amount is 2~3:1~4.Reaction kettle
Pressure is 0.5Mpa~3MPa, and 80~150 DEG C of reaction temperature, the reaction time is 4~10h.
Embodiment 1
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.2g sulfuric acid type eutectic are molten
Agent is filled with nitrogen in a high pressure reaction kettle, maintains it under pressure of 2.5Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 42%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 2
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.3g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 2.5Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 45%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 3
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 2.5Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 49%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 4
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 5.3g, 16.2g metaformaldehyde and 0.4g sulfuric acid type eutectic
Solvent pours nitrogen in a high pressure reaction kettle, maintains it under pressure of 2.5Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 43%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 5
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 2.0Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 41.2%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 6
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 2.0Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 39%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 7
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 3.0Mpa.It is anti-that 10h synthesis is carried out in 120 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 51%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 8
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 3.0Mpa.6h synthetic reaction is carried out in 120 DEG C of temperature,
It is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 46.1%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 9
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 3.0Mpa.It is anti-that 10h synthesis is carried out in 100 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 48.3%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
Embodiment 10
The amount of trying to please is the autoclave of 100ml, weighs the methanol of 6.4g, 9.0g metaformaldehyde and 0.4g sulfuric acid type eutectic are molten
Nitrogen is poured in agent in a high pressure reaction kettle, maintains it under pressure of 3.0Mpa.It is anti-that 10h synthesis is carried out in 150 DEG C of temperature
It answers, is placed into recovery room temperature after reaction, gas-chromatography is used to determine the yield of polymethoxy dimethyl ether for 53%.
The synthesis of sulfuric acid type eutectic solvent: in molar ratio: 1:1 weighs tetrabutylammonium chloride and sulfuric acid, in the item of ice bath
Under part, under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride, 10 min of stirring can form transparent molten
Sulfuric acid type eutectic solvent can be obtained in liquid.
It is to be understood that being merely to illustrate the present invention above with respect to specific descriptions of the invention and being not limited to this
Technical solution described in inventive embodiments, those skilled in the art should understand that, still the present invention can be carried out
Modification or equivalent replacement, to reach identical technical effect；As long as meet use needs, all protection scope of the present invention it
It is interior.
Claims (7)
1. a kind of method using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, which is characterized in that as follows
Implement:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, and under conditions of ice bath, sulfuric acid is added dropwise
Into tetrabutylammonium chloride until forming clear solution, sulfuric acid type eutectic solvent can be obtained；
(2) methanol, metaformaldehyde and step (1) the sulfuric acid type eutectic solvent, In the synthesis of polymethoxy dimethyl ether: are taken
It is filled with nitrogen in autoclave and carries out synthetic reaction；It is placed into after reaction and restores room temperature to get the poly- first of purpose product
Oxygroup dimethyl ether.
2. the method according to claim 1 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
Be: in the step (1), the molar ratio of the tetrabutylammonium chloride and sulfuric acid is 1:1.
3. the method according to claim 2 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
It is: in the step (1), under the conditions of whipping temp is 0 DEG C, sulfuric acid is added dropwise into tetrabutylammonium chloride until being formed transparent
Solution.
4. the method according to claim 3 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
Be: in the step (2), the molar ratio of methanol and metaformaldehyde is 2~3:1~4.
5. the method according to claim 4 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
Be: in the step (2), synthetic reaction pressure is 0.5~3Mpa.
6. the method according to claim 5 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
Be: in the step (2), synthesis reaction temperature is 80~150 DEG C.
7. the method according to claim 6 using sulfuric acid type eutectic solvent synthesis polymethoxy dimethyl ether, feature
Be: in the step (2), synthesising reacting time is 4~10h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101962318A (en) * | 2009-07-24 | 2011-02-02 | 中国科学院兰州化学物理研究所 | Method for synthesizing polymethoxy dimethyl ether under catalysis of geminal dicationic ionic liquid |
| CN102757323A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院兰州化学物理研究所 | Method for preparing alkoxy ether compounds |
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2019
- 2019-09-23 CN CN201910896634.2A patent/CN110511125B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101962318A (en) * | 2009-07-24 | 2011-02-02 | 中国科学院兰州化学物理研究所 | Method for synthesizing polymethoxy dimethyl ether under catalysis of geminal dicationic ionic liquid |
| CN102757323A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院兰州化学物理研究所 | Method for preparing alkoxy ether compounds |
Non-Patent Citations (1)
| Title |
|---|
| 李进军等: "《绿色化学导论》", 31 August 2015, 武汉大学出版社 * |
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