CN103965029B - Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane - Google Patents
Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane Download PDFInfo
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- CN103965029B CN103965029B CN201310036059.1A CN201310036059A CN103965029B CN 103965029 B CN103965029 B CN 103965029B CN 201310036059 A CN201310036059 A CN 201310036059A CN 103965029 B CN103965029 B CN 103965029B
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 34
- QLCJOAMJPCOIDI-UHFFFAOYSA-N 1-(butoxymethoxy)butane Chemical compound CCCCOCOCCCC QLCJOAMJPCOIDI-UHFFFAOYSA-N 0.000 title claims abstract description 19
- HOMDJHGZAAKUQV-UHFFFAOYSA-N 1-(propoxymethoxy)propane Chemical compound CCCOCOCCC HOMDJHGZAAKUQV-UHFFFAOYSA-N 0.000 title claims abstract description 14
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- -1 methylene diethyl Chemical group 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 18
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 16
- FBDQJKTYMCGBOZ-UHFFFAOYSA-N ethane 1-pentoxypentane Chemical compound CC.CCCCCOCCCCC FBDQJKTYMCGBOZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000010792 warming Methods 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- 238000009834 vaporization Methods 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- 238000005575 aldol reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 238000005265 energy consumption Methods 0.000 abstract description 7
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 230000003750 conditioning effect Effects 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 239000011874 heated mixture Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 229920006324 polyoxymethylene Polymers 0.000 description 12
- 238000005496 tempering Methods 0.000 description 5
- 238000004065 wastewater treatment Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000207 volumetry Methods 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
- C07C41/48—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
-
- 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
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane. The production method comprises the following steps of 1, taking formaldehyde or a formaldehyde derivative, mixing the formaldehyde or formaldehyde derivative and an alcohol raw material, and pre-heating the mixture to a temperature of 70-160 DEG C, 2, feeding the pre-heated mixture into a reactor, adding an acid catalyst into the reactor, carrying out heating until an alcohol-acid condensation reaction occurs and the materials in the reactor vaporize, and 3, releasing the produced gas from the reactor, directly feeding the gas into a rectifying tower communicated with the reactor, carrying out rectification, and taking out the product on the bottom of the rectifying tower, wherein the internal pressure of the rectifying tower is less than zero. The production method only adopts a rectifying tower-based treatment process, does not additionally use a dehydrating agent, and can produce a dibutoxymethane equimolecular quantity conditioning agent having water content less than 100ppm and purity more than 95%. The production method has simple processes and short production time, obviously reduces energy consumption and is suitable for industrial production.
Description
Technical field
The present invention relates to the production method of a kind of dibutoxy methane, methylene diethyl ether, propylal and diamyl oxygen methylmethane.
Background technology
Dibutoxy methane, methylene diethyl ether, propylal and diamyl oxygen methylmethane, be widely used in the industry, not only can be used as the solvent in organic synthesis, the solvent in battery, fuel dope etc., can also as the reagent of organic reaction.
Polyoxymethylene (polyoxymethylene), has another name called polyoxymethylene, and it is that main chain contains (– CH
2– O-) the linear macromolecule polymkeric substance of chain link.In order to obtain the polyoxymethylene resin of suitable molecular weight, if melting index is at the product (its number-average molecular weight is generally 180000-220000g/mol) of 9.0g/10min, need in the course of the polymerization process to utilize the molecular weight of molecular weight regulator to product to regulate and control.Dibutoxy methane, methylene diethyl ether, propylal and diamyl oxygen methylmethane are all extremely suitable as the molecular weight regulator in polyoxymethylene resin polymerization process.But, the copolymerization of trioxymethylene and comonomer dioxolane has very harsh requirement to material purity, especially water content can bring remarkably influenced to the quality of polyoxymethylene: higher water content significantly can increase the unstable end-group content of polyoxymethylene product in polyoxymethylene building-up process, reduces the thermostability of polyoxymethylene simultaneously.Therefore, be used as the dibutoxy methane of molecular weight regulator, methylene diethyl ether, propylal and diamyl oxygen methylmethane to need to be refined to high purity, and, when purity higher than more than 94% time, the quality of water content on polyoxymethylene of molecular weight regulator has remarkably influenced, and the corresponding reduction of the impact of its purity on polyoxymethylene quality.Think at present, the water content of molecular weight regulator is not preferably higher than 100ppm.
At present for the preparation of the method for above-mentioned molecular weight regulator, mainly adopt aldol condensation method.It adopts alcohols feedstock (as butanols, ethanol, propyl alcohol etc.) and formaldehyde, trioxymethylene or paraformaldehyde to react condensation under an acid catalysis to form, and its reaction times is short, and yield is high, is ideal preparation method.But, utilize the dibutoxy methane of produced in conventional processes, methylene diethyl ether, propylal and diamyl oxygen methylmethane, although need to improve its purity by two or more rectifying tower, water content is general also at about 1000ppm, cannot reach the requirement lower than 100ppm.If desired reduce water content again, also need to use dewatering agent, and adding of dewatering agent not only increases production cost, can cause again the decline of product purity simultaneously.
Therefore, for polyoxymethylene production of resins industry, working out the production method of a kind of low moisture, less energy-consumption, the dibutoxy methane of high yield, methylene diethyl ether, propylal and diamyl oxygen methylmethane, is extremely urgent demand.
Summary of the invention
The object of the present invention is to provide the production method of a kind of low moisture, less energy-consumption, the dibutoxy methane of high yield, methylene diethyl ether, propylal and diamyl oxygen methylmethane.
The invention provides the production method of dibutoxy methane, methylene diethyl ether, propylal or diamyl oxygen methylmethane, it comprises the steps:
(1) get formaldehyde or formaldehyde derivatives, mix with alcohols feedstock, be preheated to 70-160 DEG C;
(2) compound after preheating is dropped in reactor, then add acid catalyst, be warming up to and aldol reaction occur and makes material vaporization in reactor;
(3) gas produced is overflowed from reactor, directly enters in the rectifying tower be communicated with reactor, after rectifying, gets rectifier bottoms product, to obtain final product; Wherein, rectifying tower inside is negative pressure.
The acid catalyst that the present invention uses is classical acid catalyzer, as dilute sulphuric acid, and Phenylsulfonic acid etc.Rectifying tower of the present invention is valve tray column or packing tower.
Further, in step (2), 80-200 DEG C is warming up to; In step (3), the pressure of rectifying tower inside is-0.01--0.09MPa.
Further, in step (2), 100-190 DEG C is warming up to.
Wherein, the mass ratio of formaldehyde or formaldehyde derivatives and alcohols feedstock is (1:5) ~ (5:1).
Further, described formaldehyde derivatives is trioxymethylene or paraformaldehyde.
Further, described alcohols feedstock is ethanol, propyl alcohol, butanols or amylalcohol.
Production method of the present invention, only adopts a rectifying tower process, no longer additionally uses dewatering agent, just can obtain the dibutoxy methane equimolecular quantity conditioning agent of water content lower than 100ppm, and purity all can reach more than 95%; The method operation steps is simple, and the production time is shorter, and energy consumption obviously reduces, and is more suitable for industrialized production.
Specific implementation method
Below by way of specific embodiment, the present invention is described further, but the present invention not limit by following examples.
The production method of embodiment 1 dibutoxy methane
The ratio of formaldehyde and butanols 5:1 is added tempering tank, is heated to 70 DEG C, then adds reactor by given pace, add acid catalyst to reactor, be warming up to 180 DEG C, gas constantly enters from reactor effusion the rectifying tower be connected with reactor; Vacuumize system, pressure-controlling is-0.09MPa, and rectifier bottoms obtains the dibutoxy methane product of concentration 95.0%.Rectifying tower top is water and a small amount of organism, enters Waste Water Treatment.The whole mode of production is continuous seepage, without the need to additional dewatering agent in production process.
The production method of embodiment 2 diamyl oxygen methylmethane
Trioxymethylene and amylalcohol add tempering tank in the ratio of 1:5, are heated to 160 DEG C, then add reactor by given pace, add acid catalyst to reactor, are warming up to 200 DEG C, and gas constantly enters from reactor effusion the rectifying tower be connected with reactor; Vacuumize system, pressure-controlling is-0.09MPa, and it is 99.5% diamyl oxygen methylmethane product that rectifier bottoms obtains concentration.Rectifying tower top is water and a small amount of organism, enters Waste Water Treatment.
The production method of embodiment 3 methylene diethyl ether
The ratio of paraformaldehyde and ethanol 1:4 adds tempering tank, is heated to 145 DEG C, then adds reactor by given pace, add acid catalyst to reactor, is warming up to 160 DEG C, and gas constantly enters from reactor effusion the rectifying tower be connected with reactor; Vacuumize system, pressure-controlling is-0.06MPa, and rectifier bottoms obtains the methylene diethyl ether product of concentration 97.8%.Rectifying tower top is water and a small amount of organism, enters Waste Water Treatment.
The production method of embodiment 4 dibutoxy methane
Trioxymethylene and butanols add tempering tank in the ratio of 3:1, are heated to 155 DEG C, then add reactor by given pace, add acid catalyst to reactor, are warming up to 185 DEG C, and gas constantly enters from reactor effusion the rectifying tower be connected with reactor; Vacuumize system, pressure-controlling is-0.09MPa, and rectifier bottoms obtains the dibutoxy methane product of concentration 99.9%.Rectifying tower top is water and a small amount of organism, enters Waste Water Treatment.
The production method of embodiment 5 propylal
Trioxymethylene and propyl alcohol add tempering tank in the ratio of 4:1, are heated to 95 DEG C, then add reactor by given pace, add acid catalyst to reactor, are warming up to 165 DEG C, and gas constantly enters from reactor effusion the rectifying tower be connected with reactor; Vacuumize system, pressure-controlling is-0.09MPa, and rectifier bottoms obtains the propylal product of concentration 99.9%.Rectifying tower top is water and a small amount of organism, enters Waste Water Treatment.
Below by way of test example, beneficial effect of the present invention is described
The water content of the product that test example 1 the present invention produces and purity testing
In embodiment, the purity of final synthetic product utilizes vapor-phase chromatography to measure.The water content of product adopts micro-moisture analyzer (Ka Er-Fei Xiu volumetry or electrolytic process) to measure.Test result lists in table 1.
Table 1
Brief summary:
(1) all adopt more than 2 times rectifying tower purifying in traditional method, and still need to use dewatering agent effectively can reduce the water content of product; And in production method of the present invention, only utilize a rectifying tower just can obtain Ultra-low Moisture Content and highly purified product, break traditional technology prejudice, achieve beyond thought technique effect.
(2) in the present invention, rectifying under reduced pressure carries out, because reactor is directly connected with rectifying tower, it is also reduced pressure atmosphere in reactor, meanwhile, Raw of the present invention has one to be significantly heated to the process of 70-160 DEG C upon mixing, is conducive to after catalyzer is introduced, reaction can be carried out efficiently, thus raising reaction efficiency, Reaction time shorten, saves reaction cost.
For dibutoxy methane, energy consumption and the Cost comparisons of traditional method (comprising the process of two stage rectification tower) and the inventive method are as follows:
Table 2
| Energy consumption/product per ton | Production time | |
| Traditional method | 2-3 ton steam, 30-40 degree electricity | 2.5-3.5 hour |
| The inventive method | 0.7-1.2 ton steam, 11-22 degree electricity | 1-1.5 hour |
(3) the present invention in the reactor reacting by heating time, the heat not only needed for demand fulfillment aldol condensation, also needs reacted material is effectively vaporized simultaneously.Find in test, the product generated in reactor can produce azeotropic with other material, and there is reduced pressure atmosphere, therefore, the temperature condition in determination reactor of the present invention is 80-200 DEG C, in order to ensure reaction and vaporization completely simultaneously, avoid again high temperature to the decomposition of product, can preferred 100-190 DEG C.
As can be seen here, compared with traditional method, production method energy consumption of the present invention significantly reduces, and the production time obviously shortens, and is more suitable for industrialized production.
Claims (6)
1. the production method of dibutoxy methane, methylene diethyl ether, propylal or diamyl oxygen methylmethane, is characterized in that: it comprises the steps:
(1) get formaldehyde or formaldehyde derivatives, mix with alcohols feedstock, be preheated to 70-160 DEG C, described formaldehyde derivatives is trioxymethylene or paraformaldehyde;
(2) compound after preheating is dropped in reactor, then add acid catalyst, be warming up to and aldol reaction occur and makes material vaporization in reactor;
(3) gas produced is overflowed from reactor, directly enters in the rectifying tower be communicated with reactor, after rectifying, gets rectifier bottoms product, to obtain final product; Wherein, rectifying tower inside is negative pressure.
2. production method according to claim 1, is characterized in that: in step (2), be warming up to 80-200 DEG C; In step (3), the pressure of rectifying tower inside is-0.01--0.09MPa.
3. production method according to claim 2, is characterized in that: in step (2), be warming up to 100-190 DEG C.
4. production method according to claim 1 and 2, is characterized in that: described rectifying tower is valve tray column or packing tower.
5. production method according to claim 1, is characterized in that: the mass ratio of formaldehyde or formaldehyde derivatives and alcohols feedstock is (1:5) ~ (5:1).
6. production method according to claim 1 or 5, is characterized in that: described alcohols feedstock is ethanol, propyl alcohol, butanols or amylalcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310036059.1A CN103965029B (en) | 2013-01-30 | 2013-01-30 | Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310036059.1A CN103965029B (en) | 2013-01-30 | 2013-01-30 | Production method of dibutoxymethane, diethoxymethane, dipropoxymethane or dipentyloxymethane |
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| Publication Number | Publication Date |
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| CN103965029A CN103965029A (en) | 2014-08-06 |
| CN103965029B true CN103965029B (en) | 2015-06-24 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106748677A (en) * | 2016-12-09 | 2017-05-31 | 苏州双湖化工技术有限公司 | Take support type acidic ion liquid as the method for catalyst preparation diethoxymethane |
| CN108047006B (en) * | 2017-12-29 | 2021-05-14 | 南京师范大学 | A kind of method for preparing diethoxymethane |
| CN110551007A (en) * | 2019-09-05 | 2019-12-10 | 深圳市前海博扬研究院有限公司 | purification method for preparing dibutoxymethane by acid catalysis |
| CN114751812B (en) * | 2022-04-22 | 2024-11-19 | 甘肃美润新材料科技有限公司 | A method for producing diethoxymethane using paraformaldehyde |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535458A (en) * | 1950-12-26 | Production of formals | ||
| CN102206145A (en) * | 2010-03-31 | 2011-10-05 | 东莞市同舟化工有限公司 | Continuous catalysis and rectification technology for synthesizing diethoxymethane |
| EP2500335A1 (en) * | 2011-03-18 | 2012-09-19 | Technische Universität Kaiserslautern | Method for separating ethylal from ethanol and mixtures containing ethylal |
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2013
- 2013-01-30 CN CN201310036059.1A patent/CN103965029B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535458A (en) * | 1950-12-26 | Production of formals | ||
| CN102206145A (en) * | 2010-03-31 | 2011-10-05 | 东莞市同舟化工有限公司 | Continuous catalysis and rectification technology for synthesizing diethoxymethane |
| EP2500335A1 (en) * | 2011-03-18 | 2012-09-19 | Technische Universität Kaiserslautern | Method for separating ethylal from ethanol and mixtures containing ethylal |
Non-Patent Citations (2)
| Title |
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| 二乙氧基甲烷的制备和应用;张士英等;《合成化学》;19971231;第5卷(第4期);344-348、356 * |
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