CN110511125B - Method for synthesizing polymethoxy dimethyl ether by adopting sulfuric acid type eutectic solvent - Google Patents
Method for synthesizing polymethoxy dimethyl ether by adopting sulfuric acid type eutectic solvent Download PDFInfo
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Abstract
The invention belongs to the field of synthesis of polymethoxy dimethyl ether as a diesel cetane additive, and particularly relates to a method for synthesizing polymethoxy dimethyl ether by using a sulfuric acid type eutectic solvent, which is implemented by the following steps: weighing tetrabutylammonium chloride and sulfuric acid, and dropwise adding sulfuric acid into the tetrabutylammonium chloride under the ice bath condition until a transparent solution is formed, so as to obtain a sulfuric acid type eutectic solvent; (2) the process for synthesizing polymethoxy dimethyl ether comprises the following steps: taking a high-pressure reaction kettle with the capacity of 100ml, weighing a certain amount of methanol, trioxymethylene and a sulfuric acid type eutectic solvent, filling nitrogen into the high-pressure reaction kettle, carrying out synthetic reaction, placing the high-pressure reaction kettle to the room temperature after the reaction is finished, and determining the yield of the polymethoxy dimethyl ether by adopting gas chromatography. In the preparation process, the synthesis method of the adopted catalyst is simple, the post-treatment process is not needed, and the production cost of the catalyst is greatly reduced.
Description
Technical Field
The invention belongs to the field of synthesis of polymethoxy dimethyl ether as a diesel cetane number improver, and particularly relates to a method for synthesizing polymethoxy dimethyl ether by using a sulfuric acid type eutectic solvent.
Background
The problems that the combustion efficiency of diesel oil is low, the combustion performance is poor, the discharged tail gas pollutes the environment and the like exist in the combustion process of the diesel oil. The effective method is to add the cetane number improver into the diesel oil to improve the combustion performance of the diesel oil, so that the synthesis of the high-efficiency cetane number improver has important practical significance.
Polyoxymethylene dimethyl ether, also called PODEN, is a polyether compound with low molecular weight, has higher oxygen content and higher cetane number, and can effectively improve the combustion performance of diesel oil by adding a small amount of polyoxymethylene dimethyl ether into the diesel oil, effectively reduce the emission of harmful gases in tail gas and effectively reduce the pollution to the environment. The synthesis of polyoxymethylene dimethyl ethers is generally carried out by using methanol, dimethyl ether, paraformaldehyde and other raw materials under the catalysis of a strong acid catalyst. The early catalysts are mostly corrosive organic acids such as sulfuric acid, trifluoromethanesulfonic acid and the like, and the catalysts have the defect of causing severe corrosion to equipment for synthesizing polymethoxy dimethyl ether. PODEN was synthesized in yields of approximately 50% from ionic liquids as obtained from the chemical and physical research in the Central academy of Lanzhou (CN 101962318A, CN 102757323, CN 108299166A). Although the synthesized ionic liquid has a high catalytic effect, the preparation process of the ionic liquid is quite complex, active groups such as sulfonic groups and the like are generally required to be grafted onto cations, purification is required to remove impurities in the preparation process, and the reaction time is long.
In 2003, Abbott et al [ ABBOTT A P, CAPPER G, DAVIES D L, RASHEED R K, TAMBYRAQAH V. Novel solvent properties of chlorine chloride/urea mixturees [ J ]. Chem. Commun., 2003: 70-71 ] discovered for the first time a solvent-eutectic solvent formed from a quaternary ammonium salt and an amide compound with excellent physicochemical properties. The eutectic solvent is synthesized by hydrogen bonds by taking hydrogen bond donors (organic acid, alcohol and the like) and hydrogen bond acceptors (ammonium salt, metal chloride and the like) as raw materials. The physical and chemical properties of the Eutectic solvent are very similar to those of the ionic liquid, so that the Eutectic solvent is also classified as a novel ionic liquid or ionic liquid analogue [ Walu, friend, development of Eutectic solvent and application research thereof [ J ]. chemical bulletin, 2011,74 (4): 333-. The solvent has simple synthesis process and atom utilization rate up to 100%, and is a novel green solvent. At present, eutectic solvents attract extensive attention of researchers in various countries in the world, and show good application prospects in the fields of separation processes, chemical reactions, functional materials, electrochemistry and the like. However, the eutectic solvent is not applied to the field of synthesis of polymethoxy dimethyl ether at present.
Disclosure of Invention
The invention aims to provide a method for synthesizing polymethoxy dimethyl ether by adopting a sulfuric acid type eutectic solvent. The sulfate type eutectic solvent in the synthesis of the polymethoxy dimethyl ether can be used as a catalyst, the preparation time and the production cost of the catalyst can be effectively reduced, the yield of the target product is high, and the industrialization of the process is facilitated.
In order to solve the technical problem, the invention is realized as follows:
a method for synthesizing polymethoxy dimethyl ether by adopting a sulfuric acid type eutectic solvent is implemented according to the following steps:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, and dropwise adding sulfuric acid into the tetrabutylammonium chloride under the ice bath condition until a transparent solution is formed, so as to obtain a sulfuric acid type eutectic solvent;
(2) and (3) synthesis of polymethoxy dimethyl ether: filling nitrogen into a high-pressure reaction kettle by taking methanol, trioxymethylene and the sulfuric acid type eutectic solvent in the step (1) and carrying out synthetic reaction; after the reaction is finished, the mixture is placed to the room temperature, and the target product polymethoxy dimethyl ether is obtained.
As a preferable scheme, in the step (1) of the invention, the molar ratio of the tetrabutylammonium chloride to the sulfuric acid is 1: 1.
Further, in the step (1), sulfuric acid is dripped into tetrabutylammonium chloride under the condition that the stirring temperature is 0 ℃, and a transparent solution can be formed after stirring for 10 min, so that the sulfuric acid type eutectic solvent can be obtained.
Furthermore, in the step (2), the molar ratio of the methanol to the trioxymethylene is 2-3: 1-4.
Furthermore, in the step (2), the synthesis reaction pressure is 0.5-3 MPa.
Further, in the step (2), the synthesis reaction temperature is 80-150 ℃.
Further, in the step (2), the synthesis reaction time is 4-10 h.
The structural formula of the sulfuric acid type eutectic solvent used in the invention is as follows:
in the preparation process of the invention, all reagents are commercial products, and complicated preparation is not needed. In the preparation process of the invention, the adopted catalyst is both a catalyst and an extracting agent, thereby reducing the production cost and simplifying the procedure for synthesizing the polymethoxy dimethyl ether. In addition, the invention has good balance between the improvement of the conversion rate and the enhancement of the environmental protection efficiency. The sulfate type eutectic solvent in the synthesis of the polymethoxy dimethyl ether can be used as a catalyst, the preparation time and the production cost of the catalyst can be effectively reduced, the yield of the target product is high, and the industrialization of the process is facilitated.
Drawings
The invention is further described with reference to the following figures and detailed description. The scope of the invention is not limited to the following expressions.
FIG. 1 is an infrared spectrum of a sulfuric acid type eutectic solvent synthesized in the present invention.
In the figure, a-sulfuric acid type eutectic solvent, b-tetrabutylammonium chloride and c-sulfuric acid.
Detailed Description
A method for synthesizing polymethoxy dimethyl ether by adopting a sulfuric acid type eutectic solvent comprises the following steps:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, and dropwise adding sulfuric acid while stirring in a conical flask containing tetrabutylammonium chloride under an ice bath condition until a mixture forms a transparent solution, thus obtaining a sulfuric acid type eutectic solvent;
(2) the process for synthesizing polymethoxy dimethyl ether comprises the following steps: a high-pressure reaction kettle with the capacity of 100ml is taken, a certain amount of methanol, trioxymethylene and a sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to maintain a certain pressure. Carrying out synthetic reaction at a certain temperature and pressure, placing the mixture to return to room temperature after the reaction is finished, and determining the yield of the polymethoxy dimethyl ether by adopting gas chromatography. In the step (1), the molar ratio of tetrabutylammonium chloride to sulfuric acid is 1:1, the reaction temperature is 0 ℃, and the sulfuric acid is added dropwise.
In the step (2), the molar ratio of the addition amount of the methanol to the trioxymethylene is 2-3: 1-4. The pressure of the reaction kettle is 0.5 MPa-3 MPa, the reaction temperature is 80-150 ℃, and the reaction time is 4-10 h.
Example 1
A high-pressure reaction kettle with the capacity of 100ml is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.2g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the high-pressure reaction kettle at the pressure of 2.5 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 42% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 2
A100 ml high-pressure reaction kettle is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.3g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 2.5 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 45% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 3
A100 ml high-pressure reaction kettle is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 2.5 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 49% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 4
A100 ml high-pressure reaction kettle is taken, 5.3g of methanol, 16.2g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 2.5 MPa. The synthetic reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 43% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 5
A100 ml high-pressure reaction kettle is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 2.0 MPa. The synthetic reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to be recovered to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 41.2% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 6
A100 ml high-pressure reaction kettle is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 2.0 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 39% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 7
A high-pressure reaction kettle with the capacity of 100ml is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 3.0 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 120 ℃, the reaction is placed to be recovered to room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 51% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 8
A high-pressure reaction kettle with the capacity of 100ml is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 3.0 MPa. The synthetic reaction is carried out for 6 hours at the temperature of 120 ℃, the reaction is placed to be recovered to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 46.1% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 9
A high-pressure reaction kettle with the capacity of 100ml is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 3.0 MPa. The synthetic reaction is carried out for 10 hours at the temperature of 100 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 48.3% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
Example 10
A high-pressure reaction kettle with the capacity of 100ml is taken, 6.4g of methanol, 9.0g of trioxymethylene and 0.4g of sulfuric acid type eutectic solvent are weighed, and nitrogen is filled into the high-pressure reaction kettle to keep the pressure of the high-pressure reaction kettle at 3.0 MPa. The synthesis reaction is carried out for 10 hours at the temperature of 150 ℃, the reaction is placed to the room temperature after the reaction is finished, and the yield of the polymethoxy dimethyl ether is determined to be 53% by adopting gas chromatography.
Synthesis of sulfuric acid type eutectic solvent: according to molar ratio: 1:1, weighing tetrabutylammonium chloride and sulfuric acid, dropwise adding sulfuric acid into the tetrabutylammonium chloride under the condition of ice bath and at the stirring temperature of 0 ℃, and stirring for 10 min to form a transparent solution, thus obtaining the sulfuric acid type eutectic solvent.
It should be understood that the detailed description of the present invention is only for illustrating the present invention and is not limited by the technical solutions described in the embodiments of the present invention, and those skilled in the art should understand that the present invention can be modified or substituted equally to achieve the same technical effects; as long as the use requirements are met, the method is within the protection scope of the invention.
Claims (1)
1. A method for synthesizing polymethoxy dimethyl ether by adopting a sulfuric acid type eutectic solvent is characterized by comprising the following steps:
(1) synthesis of sulfuric acid type eutectic solvent: weighing tetrabutylammonium chloride and sulfuric acid, and dropwise adding the sulfuric acid into the tetrabutylammonium chloride at the stirring temperature of 0 ℃ until a transparent solution is formed, so as to obtain a sulfuric acid type eutectic solvent; the molar ratio of tetrabutylammonium chloride to sulfuric acid is 1: 1;
(2) and (3) synthesis of polymethoxy dimethyl ether: filling nitrogen into a high-pressure reaction kettle by taking methanol, trioxymethylene and the sulfuric acid type eutectic solvent in the step (1) and carrying out synthetic reaction; after the reaction is finished, the mixture is placed to the room temperature to be recovered, and the target product polymethoxy dimethyl ether is obtained; the synthesis reaction temperature is 80-150 ℃; the synthesis reaction time is 4-10 h; the molar ratio of the methanol to the trioxymethylene is 2-3: 1-4; the synthesis reaction pressure is 0.5-3 Mpa.
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| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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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