CN106883106A - The method of the efficient catalytic synthesis of dimethoxym ethane - Google Patents
The method of the efficient catalytic synthesis of dimethoxym ethane Download PDFInfo
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- CN106883106A CN106883106A CN201710197458.4A CN201710197458A CN106883106A CN 106883106 A CN106883106 A CN 106883106A CN 201710197458 A CN201710197458 A CN 201710197458A CN 106883106 A CN106883106 A CN 106883106A
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- 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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Abstract
The method of the efficient catalytic synthesis of dimethoxym ethane, it belongs to organic chemical synthesis field.The present invention comprises the following steps：Step 1, the absolute methanol for weighing 30~50 parts respectively according to parts by weight, 12~50 parts of metaformaldehyde, 0.01~0.5 part of composite catalyst；Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, composite catalyst, 80~140 DEG C of heating-up temperature, 100~500rad/min of speed of agitator, 6~14h of reaction time are added under conditions of agitating heating afterwards；The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature；Composite catalyst is the one kind in composite oxide of metal, molecular sieve type catalyst, metal oxide supported molecular sieve type catalyst.Conversion ratio of the present invention is high with selectivity, and reaction condition is gentle, and pressure is normal pressure, and the solid catalyst for using is repeatable to be utilized, and process is simple, operation is easy.
Description
Technical field
The invention belongs to organic chemical synthesis field；The method of the efficient catalytic synthesis of specifically related to a kind of dimethoxym ethane.
Background technology
Dimethoxym ethane has excellent physicochemical property, i.e. good dissolubility, low boiling, property compatible with water good, can answer extensively
For cosmetics, medicine, household supplies, industrial automotive articles for use, insecticide, leather polish, cleaning agent, rubber industry, paint,
In the products such as ink.It is also used as fuel additive, and the combustibility after addition to fuel is significantly improved, and reduces
Noxious gas emission.Can also be used as the substitute of freon in terms of air-conditioning refrigerant.
Typically there is condensation reaction and prepare in dimethoxym ethane, conventional acidic catalyst is realized by absolute methanol and formaldehyde.But
There is formaldehyde water content greatly in the method, be unfavorable for the carrying out of reaction, replace formalin synthesizing dimethoxym ethane to be solution with metaformaldehyde
The certainly effective way of above mentioned problem.Chinese patent CN102557899.A reports methyl alcohol and prepares dimethoxym ethane with metaformaldehyde reaction
Method, but apply dimethylformamide, Isosorbide-5-Nitrae-dioxane solvent in this reaction, organic solvent easily evaporate and exist it is right
The adverse effect factor of environment.Xiao Chunmei etc. reports the reaction with metaformaldehyde with perfluorinated sulfonic resin catalysis methanol, but turns
Rate is relatively low, only reaches 70%.
The content of the invention
It is an object of the present invention to provide the method that a kind of efficient dimethoxym ethane of environmental protection is catalyzed and synthesized.
The present invention is achieved through the following technical solutions：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 30~50 parts respectively according to parts by weight, 12~50 parts of metaformaldehyde, 0.01
~0.1 part of composite catalyst；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80~140 DEG C of heating-up temperature, 100~500rad/min of speed of agitator, 6~14h of reaction time are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, composite catalyst is metal composite oxygen in step 1
One kind in compound, molecular sieve type catalyst, metal oxide supported molecular sieve type catalyst.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, the composite oxide of metal in step 2 includes weight
Amount number is 0~10 part of Fe2O3, the ZnO that parts by weight are 0~10 part, the CuO that parts by weight are 0~10 part, parts by weight
It is 0~10 part of NiO.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, Fe in the composite oxide of metal in step 22O3
Parts by weight be 5 parts, the parts by weight of ZnO are 5 parts, and the parts by weight of NiO are 1 part.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, CuO in the composite oxide of metal in step 2
Parts by weight are 5 parts, and the parts by weight of NiO are 5 parts.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, ZnO in the composite oxide of metal in step 2
Parts by weight are 10 parts, and the parts by weight of NiO are 3 parts.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, the molecular sieve type catalyst in step 2 includes weight
Amount number is 0~10 part of ZSM types molecular sieve, the Y type molecular sieve that parts by weight are 0~10 part.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, the metal oxide supported molecular sieve in step 2
Type catalyst is CuO load type ZSM 5 molecular sieves catalyst, Fe2O3Load type ZSM 5 molecular sieve catalyst, ZnO loads ZSM-5
Type molecular sieve catalyst, NiO load type ZSM 5 molecular sieves catalyst, CuO loads Y zeolite catalyst, Fe2O3Load Y types
Molecular sieve catalyst, ZnO loads Y zeolite catalyst, NiO load one kind of Y zeolite catalyst.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, the parts by weight of absolute methanol are 30 in step 1
Part, the parts by weight of metaformaldehyde are 12 parts, and the parts by weight of composite catalyst are 0.05 part.
The method of the efficient catalytic synthesis of dimethoxym ethane of the present invention, 110 DEG C of heating-up temperature, speed of agitator in step 2
100rad/min, reaction time 8h.
The present invention is using composite oxide of metal, molecular sieve Metal Supported material as catalyst absolute methanol and three
The reaction of polyformaldehyde prepares dimethoxym ethane.These metal oxides include Fe2O3, ZnO, CuO, NiO etc. oxide, and
ZSM, Y type molecular sieve.It is catalyst synthesizing dimethoxym ethane with composite oxide of metal, molecular sieve Metal Supported material, through gas phase color
Spectrum determines the conversion ratio 85.9~98.2% of metaformaldehyde, and the selectivity of dimethoxym ethane is 90~93%.
This method compared with the conventional method, with effect following prominent：Conversion ratio is high with selectivity, reaction condition temperature
With pressure is normal pressure, and the solid catalyst for using is repeatable to be utilized, and process is simple, operation is easy, and raw material is cheap and easy to get.
Brief description of the drawings
Fig. 1 is the gas chromatogram of dimethoxym ethane prepared by the method for specific embodiment one；
Fig. 2 is the scanning electron microscopic picture of catalyst used in the method for specific embodiment one.
Specific embodiment
Specific embodiment one：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 30 parts respectively according to parts by weight, 12 parts of metaformaldehyde, 0.5 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 110 DEG C of heating-up temperature, speed of agitator 100rad/min, reaction time 8h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is that metal is answered in step 1
Close oxide catalyst, Fe in composite oxide of metal2O3Parts by weight be 5 parts, the parts by weight of ZnO are 5 parts, the weight of NiO
Amount number is 1 part.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, after reaction terminates, is cooled to room temperature gas
Analysis of hplc, analysis of spectra are as shown in figure 1, it can be seen that retention time 2.939min is methyl alcohol from Fig. 1, its peak area is
38252.3；Retention time is that 3.326min is dimethoxym ethane, and its peak area is 19001.9；Retention time 3.607min is carbonic acid two
Methyl esters, its peak area is 430.1；Retention time 5.079min is metaformaldehyde, and its peak area is 4363.5.By gas-chromatography
Analysis can accurately detect metaformaldehyde after the method reaction of the efficient catalytic synthesis of dimethoxym ethane described in present embodiment
Conversion ratio, the selectivity of dimethoxym ethane, the yield of dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, used composite catalyst is that metal is answered
Close oxide catalyst, Fe in composite oxide of metal2O3Parts by weight be 5 parts, the parts by weight of ZnO are 5 parts, the weight of NiO
Amount number is 1 part.
It can be seen that the SEM pictures of the catalyst used in the method for specific embodiment one from accompanying drawing 2, can be with from figure
Find out that catalyst compounds surface topography is evenly distributed.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 98.2%, the selection of dimethoxym ethane
Property 93.0%, dimethoxym ethane yield be 88%.
Specific embodiment two：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 50 parts respectively according to parts by weight, 35 parts of metaformaldehyde, 0.1 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 100 DEG C of heating-up temperature, speed of agitator 200rad/min, reaction time 10h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is molecular sieve in step 1
Type catalyst, in molecular sieve type catalyst the parts by weight of ZSM types molecular sieve be 10 parts, the parts by weight of Y type molecular sieve be 10
Part.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 94.9%, the selection of dimethoxym ethane
Property 92.5%, dimethoxym ethane yield be 86.8%.
Specific embodiment three：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 45 parts respectively according to parts by weight, 40 parts of metaformaldehyde, 0.05 part compound
Catalyst；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80 DEG C of heating-up temperature, speed of agitator 500rad/min, reaction time 14h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is Fe in step 12O3It is negative
Carry type ZSM 5 molecular sieve catalyst.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 91.9%, the selection of dimethoxym ethane
Property 92.1%, dimethoxym ethane yield be 84.4%.
The products collection efficiency of three kinds of embodiments and the conversion ratio table of comparisons of metaformaldehyde are as shown in table 1：
The method table of comparisons of the efficient catalytic synthesis of the dimethoxym ethane of table 1
Specific embodiment four：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 32 parts respectively according to parts by weight, 18 parts of metaformaldehyde, 0.2 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80 DEG C of heating-up temperature, speed of agitator 300rad/min, reaction time 9h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is CuO loads in step 1
Type ZSM 5 molecular sieve catalyst.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 92.9%, the selection of dimethoxym ethane
Property 92.1%.
Specific embodiment five：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 32 parts respectively according to parts by weight, 18 parts of metaformaldehyde, 0.2 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80 DEG C of heating-up temperature, speed of agitator 300rad/min, reaction time 6h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is NiO loads in step 1
Y zeolite catalyst.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 89.9%, the selection of dimethoxym ethane
Property 90.3%.
Specific embodiment six：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 32 parts respectively according to parts by weight, 18 parts of metaformaldehyde, 0.2 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80 DEG C of heating-up temperature, speed of agitator 200rad/min, reaction time 9h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is ZnO loads in step 1
Type ZSM 5 molecular sieve catalyst.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 94.9%, the selection of dimethoxym ethane
Property 92.3%.
Specific embodiment seven：
A kind of method of the efficient catalytic synthesis of dimethoxym ethane, comprises the following steps：
Step 1, the absolute methanol for weighing 32 parts respectively according to parts by weight, 18 parts of metaformaldehyde, 0.2 part compound are urged
Agent；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards in the bar of agitating heating
Composite catalyst, 80 DEG C of heating-up temperature, speed of agitator 200rad/min, reaction time 9h are added under part；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
The method of the efficient catalytic synthesis of the dimethoxym ethane described in present embodiment, composite catalyst is Fe in step 12O3It is negative
Carry Y zeolite catalyst.
The conversion ratio for measuring metaformaldehyde by gas chromatographic analysis in present embodiment is 94.9%, the selection of dimethoxym ethane
Property 92.7%.
Claims (10)
1. the method that a kind of efficient catalytic of dimethoxym ethane synthesizes, it is characterised in that：Comprise the following steps：
Step 1, the absolute methanol for weighing 30~50 parts respectively according to parts by weight, 12~50 parts of metaformaldehyde, 0.01~0.5
The composite catalyst of part；
Step 2, by the load weighted absolute methanol of step 1, metaformaldehyde add reactor in, afterwards under conditions of agitating heating
Add composite catalyst, 80~140 DEG C of heating-up temperature, 100~500rad/min of speed of agitator, 6~14h of reaction time；
The mixed solution obtained after step 3, step 2 reaction, filters after being cooled to room temperature, obtains described dimethoxym ethane.
2. the method that the efficient catalytic of dimethoxym ethane according to claim 1 synthesizes, it is characterised in that：It is combined in step 1 and is urged
Agent is the one kind in composite oxide of metal, molecular sieve type catalyst, metal oxide supported molecular sieve type catalyst.
3. the method that the efficient catalytic of dimethoxym ethane according to claim 2 synthesizes, it is characterised in that：Metal in step 2
Composite oxides include Fe that parts by weight are 0~10 part2O3, the ZnO that parts by weight are 0~10 part, parts by weight be 0~10
The CuO, the NiO that parts by weight are 0~10 part of part.
4. the method that the efficient catalytic of dimethoxym ethane according to claim 3 synthesizes, it is characterised in that：Metal in step 2
Fe in composite oxides2O3Parts by weight be 5 parts, the parts by weight of ZnO are 5 parts, and the parts by weight of NiO are 1 part.
5. the method that the efficient catalytic of dimethoxym ethane according to claim 3 synthesizes, it is characterised in that：Metal in step 2
The parts by weight of CuO are 5 parts in composite oxides, and the parts by weight of NiO are 5 parts.
6. the method that the efficient catalytic of dimethoxym ethane according to claim 3 synthesizes, it is characterised in that：Metal in step 2
The parts by weight of ZnO are 10 parts in composite oxides, and the parts by weight of NiO are 3 parts.
7. the method that the efficient catalytic of dimethoxym ethane according to claim 2 synthesizes, it is characterised in that：Molecule in step 2
Sieve-type catalyst includes ZSM types molecular sieve, the Y type molecular sieve that parts by weight are 0~10 part that parts by weight are 0~10 part.
8. the method that the efficient catalytic of dimethoxym ethane according to claim 2 synthesizes, it is characterised in that：Metal in step 2
Oxide carried molecular sieve type catalyst is CuO load type ZSM 5 molecular sieves catalyst, Fe2O3Load type ZSM 5 molecular sieve is urged
Agent, ZnO load type ZSM 5 molecular sieves catalyst, NiO load type ZSM 5 molecular sieves catalyst, CuO load Y type molecular sieves are urged
Agent, Fe2O3Load Y zeolite catalyst, ZnO loads Y zeolite catalyst, NiO load Y zeolite catalyst
It is a kind of.
9. the method that the efficient catalytic of dimethoxym ethane according to claim 1 synthesizes, it is characterised in that：Without water beetle in step 1
The parts by weight of alcohol are 30 parts, and the parts by weight of metaformaldehyde are 12 parts, and the parts by weight of composite catalyst are 0.05 part.
10. the method that the efficient catalytic of dimethoxym ethane according to claim 1 synthesizes, it is characterised in that：Temperature is heated in step 2
110 DEG C of degree, speed of agitator 100rad/min, reaction time 8h.
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| CN102557899A (en) * | 2012-02-07 | 2012-07-11 | 同济大学 | Methylal catalytic synthesizing method employing methanol and trioxymethylene |
| CN103664547A (en) * | 2012-09-05 | 2014-03-26 | 中国石油化工股份有限公司 | Method for synthesizing polyformaldehyde dimethyl ether |
| CN103755535A (en) * | 2014-01-03 | 2014-04-30 | 中国科学院山西煤炭化学研究所 | Preparation method of polyformaldehyde dimethyl ether |
| CN104151147A (en) * | 2013-05-16 | 2014-11-19 | 中国石油化工股份有限公司 | Method for synthesizing polyoxymethylene dimethyl ether by using polyoxymethylene |
| CN104292084A (en) * | 2014-09-05 | 2015-01-21 | 中国科学院山西煤炭化学研究所 | Method for preparing polyoxymethylene dimethyl ether under catalysis of molecular sieve with high silica-alumina ratio |
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2017
- 2017-03-29 CN CN201710197458.4A patent/CN106883106A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101972644A (en) * | 2010-11-09 | 2011-02-16 | 中国海洋石油总公司 | Method for preparing polyformaldehyde dimethyl ether by using loaded niobium oxide catalyst |
| CN102557899A (en) * | 2012-02-07 | 2012-07-11 | 同济大学 | Methylal catalytic synthesizing method employing methanol and trioxymethylene |
| CN103664547A (en) * | 2012-09-05 | 2014-03-26 | 中国石油化工股份有限公司 | Method for synthesizing polyformaldehyde dimethyl ether |
| CN104151147A (en) * | 2013-05-16 | 2014-11-19 | 中国石油化工股份有限公司 | Method for synthesizing polyoxymethylene dimethyl ether by using polyoxymethylene |
| CN103755535A (en) * | 2014-01-03 | 2014-04-30 | 中国科学院山西煤炭化学研究所 | Preparation method of polyformaldehyde dimethyl ether |
| CN104292084A (en) * | 2014-09-05 | 2015-01-21 | 中国科学院山西煤炭化学研究所 | Method for preparing polyoxymethylene dimethyl ether under catalysis of molecular sieve with high silica-alumina ratio |
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