CN101844986A - Method for preparing dimethyl carbonate by using carbon dioxide (CO2) - Google Patents
Method for preparing dimethyl carbonate by using carbon dioxide (CO2) Download PDFInfo
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- CN101844986A CN101844986A CN201010183827A CN201010183827A CN101844986A CN 101844986 A CN101844986 A CN 101844986A CN 201010183827 A CN201010183827 A CN 201010183827A CN 201010183827 A CN201010183827 A CN 201010183827A CN 101844986 A CN101844986 A CN 101844986A
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Abstract
The invention discloses a method for preparing dimethyl carbonate by using carbon dioxide (CO2), comprising the following steps: (1) generating water gas; (2) synthesizing methanol; (3) recovering the CO2; (4) synthesizing dimethyl carbonate by making the CO2 directly react with the methanol; and (5) recovering the methanol. According to the technical scheme, the method adopts the CO2 which must be treated to realize the low-carbon economic target as the raw material to prepare the dimethyl carbonate. Because the CO2 is totally produced by the water gas generating furnace, the prior defect of the emission of the CO2 generated by the water gas generating furnace can be avoided. The obsolete intermittent water coal generating furnace is modified to be used for synthesizing the two chemical products of methanol and dimethyl carbonate.
Description
Technical field
The present invention relates to a kind of method for preparing methylcarbonate.
Background technology
Reactions such as methylcarbonate DMC is expected to substitute at numerous areas severe toxicity such as poisonous phosgene, methyl-sulfate (DMS), methyl chloride and methyl-chloroformate comprehensively or carcinogens carries out carbonylation, methylates, esterification and transesterify generate multiple important Chemicals; On the other hand, be the fine chemicals that multiple high added value can be developed, be prepared to raw material with DMC, obtain widespread use in fields such as medicine, agricultural chemicals, synthetic materials, dyestuff, lubricating oil additive, food flavoring agent, electronic chemical products.In addition, other purposes such as solvent, solvent and gasoline dope etc. are also or be about to practicability.So DMC is described as " new matrix " of 21 century organic synthesis, its development will be played huge pushing effect to Coal Chemical Industry, methanol chemistry, the chlorination worker of China.CO
2Being the major industry discharge, also is one of gas that causes Global Greenhouse Effect, a kind of especially potential carbon source.CO
2Activation and utilization caused people more and more intensive pay close attention to.In the energy exhausted day by day today, CO
2It is very extensive to originate, and as raw material, cost is extremely low with it.Use CO
2Synthetic DMC is all significant aspect synthetic chemistry, carbon resource utilization and environment protection.
The synthetic route of methylcarbonate mainly contains phosgenation (comprising phosgenation methyl alcohol method, phosgene sodium alkoxide method), ester-interchange method, methanol solution phase oxidation carbonylation method, methanol gas-phase oxidation/carbonylation two-step approach, methyl alcohol electrolysis carbonylation method (comprising direct method and indirect method), dme oxidative carbonylation method, alcoholysis of urea, methanol gas-phase oxidation/carbonylation direct synthesis technique.Wherein ester-interchange method ratio therein is maximum, and especially at home, what most of enterprises of now having gone into operation used all is ester-interchange method.What the main De Shigu company of methylcarbonate manufacturing enterprise of the U.S. used also is ester exchange process.Ube uses the methanol gas-phase oxidation/carbonylation two-step approach.The synthetic DMC of methanol gas-phase oxidation/carbonylation method is a kind of technology that is being developed.
One, industrialized production process:
A. phosgenation
Phosgenation is classical DMC synthetic method, can be divided into phosgene methyl alcohol method photoreactive gas sodium alkoxide method.
1, phosgenation methyl alcohol method is the method the earliest of producing DMC, and its technological process is: phosgene and methyl alcohol reaction, generate methyl chlorocarbonate earlier, and methyl chlorocarbonate and methyl alcohol further reaction obtain DMC.
COCl
2+CH
3OH→ClCOOCH
3+HCl...........................................(1)
ClCOOCH
3+CH
3OH→(CH
3O)
2CO+HCl...................................(2)
Total reaction: COCl
2+ 2CH
3OH → (CH
3O) CO+2HCl........................... (3)
Advantage: technical maturity, but industrial-scale production DMC.
Shortcoming: complex process, operational cycle length, raw material phosgene severe toxicity, a large amount of hydrochloric acid of by-product, serious environment pollution, to problems such as equipment requirements height, should not promote.
2, phosgene sodium alkoxide method is the improvement of phosgene methyl alcohol method, by phosgene and sodium methylate reaction system DMC.
COCl
2+2CH
3ONa→(CH
3O)
2CO+2NaCl................................(4)
Advantage: avoided phosgene methyl alcohol method by-product to have the hydrochloric acid that severe corrosive is difficult for recovery again.
Shortcoming: still use the highly toxic product phosgene to be raw material.
As raw material, environmental pollution is big with the phosgene of severe toxicity for phosgenation, and grievous injury production line employee's health brings bigger production safety to threaten simultaneously.Paying attention to environment protection and production safety, paying close attention to the 21 century phosgenation of enterprise employee health and progressively eliminated.
B. ester-interchange method
With methyl alcohol and ethylene carbonate (or propylene) ester is raw material, carries out transesterification reaction to methylcarbonate under catalyst action, and by-product second (or third) glycol.Texaco Oil has at first realized the suitability for industrialized production of ester-interchange method, and reaction formula is:
(CH
2O)
2CO+2CH
3OH→(CH
3O)
2CO+CH
2OHCH
2OH.........................(5)
Advantage: its reaction yield is higher, but and by-product ethylene glycol.
Shortcoming: the unit volume equipment capacity is low, the cost of equipment height, and the required energy consumption of separation and purification is bigger.By product hexylene glycol output is huge, but sales difficulty.
C. methanol solution phase oxidation carbonylation method
Produce a kind of of DMC as non-phosgene, gondola ENI chemosynthesis company has realized first that in nineteen eighty-three methanol solution phase oxidation carbonylation method prepares the suitability for industrialized production of DMC, and domestic also have unit to carry out state's research.Chemical equation is:
Advantage: yield height, once through yield are 32%, selectivity by methyl alcohol greater than 98%.
Shortcoming: production equipment adopts tank reactor, and failing to overcome carbon monoxide is subtraction function and these unfavorable factors of catalyzer hydrolysis of time to the selectivity of DMC.For making oxygen level in the tail gas not in explosive range, the controlled oxidation flow velocity must cause the gain in yield of refuse carbonic acid gas to prolong the reaction times of every still effectively, can not in time remove the water that produces in the reactive system.Finally cause selectivity by the carbonyl meter instability, catalyst life is short, and equipment corrosion is big.
D. methanol gas-phase oxidation/carbonylation two-step approach
The emerging product company of space portion of Japan has set up the full scale plant of producing 3000 tons of DMC per year in 1992, reaction divides two sections and carries out.In first section reaction, be raw material, obtain methyl nitrite with methyl alcohol and NO.In second section reaction, methyl nitrite and carbon monoxide generate DMC in the enterprising promoting the circulation of qi phase reaction of Pd series catalysts, and the NO of by-product is re-used as raw material and returns the first step reaction utilization at this moment.Reaction formula is:
2CH
3ONO+CO→2(CH
3O)
2CO+2NO.........................................................(8)
Total reaction:
The characteristics of this method are that CO is reacted under oxygen atmosphere, so to the selectivity of CO up to 90%, the DMC space-time yield is higher, but this reaction exists complex process, the easy blocking pipeline of by-product dimethyl oxalate and problems such as NO preparation and circulation, and oxynitrides and methyl nitrite belong to hazardous chemical.
Advantage: CO reacts under oxygen atmosphere, thus to the selectivity of CO up to 90%, the DMC space-time yield is higher.
Shortcoming: second-stage reaction, complex process, the easy blocking pipeline of by-product dimethyl oxalate and problems such as the need deleterious NO of preparation and its circulation.
Two, the technology of researching and developing
1. methyl alcohol electrolysis carbonylation method
1) indirect method
Employing halogenide such as Robert are made ionogen, add VIII B element simultaneously and carry out the synthetic DMC of methyl alcohol electrolysis carbonylation as catalyzer in ionogen, and its catalyst effect is in proper order: Pd＞Pt, Rh, Ir＞Fe, Ru, Os＞Co＞Ni.Except that VIII B element, its inorganics, organism or complex compound all can be made catalyzer.He finds the halogen ion pair, and this reacts to such an extent that active order is: Br＞Cl＞I.When being ionogen with LiBr, on the carbonyl compound catalyzer of load 5wt% palladium, under the room temperature, reacted 3 hours, generation DMC gets current efficiency and reaches 92%.
Advantage: the current efficiency of indirect method generation DMC is higher.
Shortcoming: carrying out in liquid phase, is ionogen with the halogen ion, has increased reaction complicacy and product separation difficulty.
2) direct method
Kiyoshi etc. are to be dipped in SiO
2H in the fiber
3PO
4Be ionogen, CuCl arranged by load
2, PdCl
2Graphite as electrode, at room temperature carry out the synthetic DMC of direct electrolysis carbonylation effect of gas-phase methanol.
Advantage: direct method is a gas-phase reaction, overcomes the shortcoming of indirect method.
Shortcoming: have serious side reaction, the current efficiency that generates DMC is lower.
2. dme oxidative carbonylation method
Oxidation carbonylation takes place and generates DMC in dme and CO, O2, is very favorable reaction on thermodynamics, and free energy of reaction is changed to-189kJ/mol (100 ℃).
Advantage: only generating methylcarbonate, do not have other by product and water to generate, is the reaction that industrial application value is very arranged.
Shortcoming: but the research report is seldom, and particularly the research to catalyzer is difficult to find.
3. alcoholysis of urea
Utilize gas formulation urea production process, make carbonic acid gas and ammonia urea synthesis, alcoholysis reaction generation DMC takes place in urea under suitable condition then.
CO
2+2NH
3→(NH
2)
2CO+H
2O.................................................................(12)
(NH
2)
2CO+2CH
3OH→(CH
3O)
2CO.............................................................(13)
Advantage: this reaction adopts liquid phase synthesis process to carry out in autoclave, has that raw material is cheap and easy to get, technology is simple, operational condition is gentle and avoid other route to need the characteristics of the complex system of separation of methanol-DMC-water.
Shortcoming: this method exists that equilibrium conversion is low, homogeneous catalyst is difficult to problems such as Separation and Recovery at present.So this method still is in the research exploratory stage at present.
4. methanol gas-phase oxidation/carbonylation direct synthesis technique
This method is with gas-phase methanol and CO, O
2Mixed gas by in the fixed-bed reactor that catalyzer is housed, the direct gas-phase oxidation/carbonylation of methyl alcohol generates DMC:
Advantage: adopted gas-solid phase reaction, both avoided the separation problem of catalyzer in the liquid phase puddling, avoided the use of NO toxic gas in the gas phase indirect method again, and made reaction process become simple, be a synthetic route that prospects for commercial application is arranged very much, by domestic and international experts and scholars' extensive concern.
Shortcoming: but technology is not very ripe, the easy inactivation of catalyzer, methanol conversion is not high, the DMC space-time yield is not high, and when separating because the methyl alcohol ratio is big, separate relatively difficulty.
Technology compares: for the methylcarbonate synthesis technique, phosgenation exists complex process, operational cycle length, raw material phosgene severe toxicity, a large amount of hydrochloric acid of by-product, serious environment pollution to reach shortcomings such as equipment requirements height, does not meet the green science and technology strategy, has been eliminated; Though methanol gas-phase oxidation/carbonylation can solve liquid phase method catalyzer and the not segregative shortcoming of product, problem such as have the easy inactivation of catalyzer, transformation efficiency is not high, technology is immature.It is raw material that ester-interchange method utilizes ethylene (third) alkene ester, and raw material sources are restricted, and depend on the development of petrochemical industry, and this reaction is subjected to thermodynamics equilibrium limit, second (third) glycol that by-product is a large amount of.The scheme contrast is as follows:
| Flow process | Catalyzer | Advantage | Shortcoming |
| Phosgenation | ??COCl 2 | Technology is ripe | Complex process, operational cycle length, raw material phosgene severe toxicity, a large amount of hydrochloric acid of by-product, serious environment pollution, to problems such as equipment requirements height, should not promote |
| Ester-interchange method | Tertiary amine and quaternary ammoniated functional group resin | Reaction yield is higher, and product does not have water to generate | The unit volume equipment capacity is low, the cost of equipment height, and the required energy consumption of separation and purification is bigger |
| The methanol gas-phase oxidation/carbonylation two-step approach | ??NO | CO reacts under oxygen atmosphere, thus to the selectivity of CO up to 90%, the DMC space-time yield is higher | Second-stage reaction, complex process, the easy blocking pipeline of by-product dimethyl oxalate and problems such as the need deleterious NO of preparation and its circulation |
| Flow process | Catalyzer | Advantage | Shortcoming |
| Methyl alcohol electrolysis carbonylation method | VIII B element | Current efficiency is higher | All carry out in liquid phase, needing with the halogen ion is ionogen, has increased the complicacy of reaction and the difficulty of product separation |
| Alcoholysis of urea | The dimethoxy dibutyl tin | Have that raw material is cheap and easy to get, technology is simple, operational condition is gentle and avoid other route to need the characteristics of the complex system of separation of methanol-DMC-water | This method exists that equilibrium conversion is low, homogeneous catalyst is difficult to problems such as Separation and Recovery |
| Methanol solution phase oxidation carbonylation method | ??CuCl | Yield height, once through yield are 32%, selectivity by methyl alcohol greater than 98% | Catalyzer separates with product, catalytic erosion equipment and recycle difficulty and inactivation |
Summary of the invention
Technical problem to be solved by this invention provides a kind of method of utilizing carbonic acid gas to prepare methylcarbonate, raw material CO
2Derive from the water-gas stove fully, avoided the CO of water-gas stove generation in the past
2Discharging.
For solving the problems of the technologies described above, the present invention adopts following technical scheme: utilize carbonic acid gas to prepare the method for methylcarbonate, may further comprise the steps:
One, water-gasization
Pretreated coke is transported to the water-gas stove by certain speed, with the oxygen delivery coal gasifier of intaking, adopt steam generator to feed water vapor by certain flow, make coke and steam reaction, generate carbon monoxide and hydrogen, export from first outlet at the carbonic acid gas that this water-gas stove produces, carbon monoxide and hydrogen mixed gas are from the second outlet output;
Two, methyl alcohol is synthetic
Carbon monoxide and hydrogen mixed gas are after the water cooler cooling, feed moisture eliminator, enter one step of gas holder store buffer, the gas mixture that comes out from gas holder heats back feeding methyl alcohol synthetic reactor by well heater, methyl alcohol after synthetic is discharged at the bottom of tower, and it is standby to be collected in the methyl alcohol basin through condenser;
Three, carbon dioxide recovery
Unreacted carbonic acid gas is got back to steam generator through separator in the methyl alcohol synthetic reactor;
Four, methylcarbonate is synthetic
The carbonic acid gas that the water-gas stove produces feeds DMC reactor and methyl alcohol reaction after cooling off, the resultant DMC product in reaction back enters scrubber tower, making that methyl alcohol is water-soluble enters at the bottom of the tower and it is separated with methylcarbonate, methylcarbonate input DMC rectifying tower is to the methylcarbonate rectification and purification, and the back methylcarbonate of purifying is exported after condenser condenses;
Five, Methanol Recovery
The methyl alcohol that generates in the scrubber tower is squeezed into methanol rectifying tower with pump, and the methyl alcohol that dilutes is carried out rectification and purification methyl alcohol, and the methyl alcohol after the rectifying enters the methyl alcohol basin behind condenser.
In the described methyl alcohol synthesis step, discharge methanol aqueous solution at the bottom of the methyl alcohol synthetic reactor tower and feed the methyl alcohol primary tower, the cooling back feeds methanol rectifying tower rectifying, and rectifying obtains purer methyl alcohol through condensation, and it is standby to be collected in the methyl alcohol basin after the cooling.
Methyl alcohol in the described methyl alcohol basin is introduced into the intermediate buffering jar before entering the DMC reactor.
The present invention has used and has realized that the low-carbon economy target needs the CO of keypoint treatment owing to adopted technique scheme
2Be raw material.Raw material CO
2Derive from the water-gas stove fully, avoided the CO of water-gas stove generation in the past
2Discharging.The intermittent type water-gas stove of having eliminated is transformed, can synthesizing methanol and two kinds of Chemicals of methylcarbonate.
Description of drawings
Fig. 1 prepares the device synoptic diagram of methylcarbonate for the present invention utilizes carbonic acid gas.
Embodiment
Below in conjunction with accompanying drawing the specific embodiment of the present invention is further described.
The present invention adopts carbonic acid gas and the synthetic methylcarbonate of producing of methyl alcohol direct reaction, and reaction formula is:
CO
2+2CH
3OH→(CH
3O)
2CO+H
2O
Carbonic acid gas and methyl alcohol are feedstock production with coke and air all, and whole technological process is three-waste free discharge almost, and technology is simple, and feasibility is strong, meet " the closed cycle thinking " of Green Chemistry, have broad prospect of application.Main characteristic is the CO that the water-gas stove is produced
2Waste gas is unstripped gas, recycles, and realizes the green synthesis process route.
Figure 1 shows that preparation technology's flow process of methylcarbonate of the present invention, may further comprise the steps:
One, water-gasization
Pretreated coke is transported to water-gas stove 3 by certain speed, adopt air separation facility 4 with ambient oxygen partial from storage, keep certain flow and calorific value to be delivered into water-gas stove 3, react: C+O
2→ CO
2C+O
2→ CO; CO+O
2→ CO
2, the carbonic acid gas that is produced is from first outlet, 31 outputs;
Adopt steam generator 1 to feed water vapor by certain flow then, make coke and steam reaction, generate carbon monoxide and hydrogen, reaction formula is: H
2O+C → CO+H
2, the carbon monoxide of generation and hydrogen mixed gas are from second outlet, 32 outputs;
Two, methyl alcohol is synthetic
Carbon monoxide and hydrogen mixed gas feed moisture eliminator 8 after water cooler 6 coolings, enter gas holder one step of 7 store buffers, and the gas mixture that comes out from gas holder 7 heats back feeding methyl alcohol synthetic reactor 9 by well heater 10, and reaction formula is: CO+2H
2→ CH
3OH
Methyl alcohol after synthetic is discharged at the bottom of tower, discharges methanol aqueous solution at the bottom of methyl alcohol synthetic reactor 9 towers to feed methyl alcohol primary tower 17, and the cooling back feeds methanol rectifying tower 18 rectifying, and rectifying obtains purer methyl alcohol, and to be collected in methyl alcohol basin 19 through condenser 16 standby;
Three, carbon dioxide recovery
Unreacted carbonic acid gas is got back to steam generator 1 through separator 13 in the methyl alcohol synthetic reactor 9;
Four, methylcarbonate is synthetic
Methyl alcohol in the described methyl alcohol basin 19 is introduced into intermediate buffering jar 22 before entering DMC reactor 20, the regulation and control methanol usage enters the DMC reactor with appropriate speed.The carbonic acid gas that water-gas stove 3 produces feeds DMC reactor and methyl alcohol reaction after cooling off, reaction formula is:
CO
2+2CH
3OH→(CH
3O)
2CO+H
2O
The resultant DMC product in reaction back enters scrubber tower 23, and make water-soluble enter at the bottom of the tower of methyl alcohol and it is separated with methylcarbonate, 24 pairs of methylcarbonate rectification and purification of methylcarbonate input DMC rectifying tower, the back methylcarbonate of purifying is exported after condenser condenses;
Five, Methanol Recovery
The methyl alcohol that generates in the scrubber tower 23 is squeezed into methanol rectifying tower 25 with pump, and the methyl alcohol that dilutes is carried out rectification and purification methyl alcohol, and the methyl alcohol after the rectifying enters methyl alcohol basin 19 behind condenser.
The invention solves traditional coal gasifier CO
2A large amount of dischargings, the problem of atmosphere pollution.Realized the green synthesis process of methylcarbonate or methyl alcohol from the source, to realizing that low-carbon economy is significant.
CO
2Be that main discharge in the industry also is the gas that causes Global Greenhouse Effect, a kind of especially potential carbon source.Therefore, all be significant aspect synthetic chemistry, carbon resource utilization and the environment protection by carbonic acid gas and the synthetic DMC of methyl alcohol.
Claims (3)
1. utilize carbonic acid gas to prepare the method for methylcarbonate, it is characterized in that: may further comprise the steps: one, water-gasization
Pretreated coke is transported to water-gas stove (3) by certain speed, with the oxygen delivery coal gasifier (3) of intaking, adopt steam generator (1) to feed water vapor by certain flow, make coke and steam reaction, generate carbon monoxide and hydrogen, export from first outlet (31) at the carbonic acid gas that this water-gas stove (3) produces, carbon monoxide and hydrogen mixed gas are from second outlet (32) output;
Two, methyl alcohol is synthetic
Carbon monoxide and hydrogen mixed gas are after water cooler (6) cooling, feed moisture eliminator (8), enter one step of gas holder (7) store buffer, the gas mixture that comes out from gas holder (7) heats back feeding methyl alcohol synthetic reactor (9) by well heater (10), methyl alcohol after synthetic is discharged at the bottom of tower, and it is standby to be collected in methyl alcohol basin (19) through condenser (16);
Three, carbon dioxide recovery
Unreacted carbonic acid gas is got back to steam generator (1) through separator (13) in the methyl alcohol synthetic reactor (9);
Four, methylcarbonate is synthetic
The carbonic acid gas that water-gas stove (3) produces feeds DMC reactor and methyl alcohol reaction after cooling off, the resultant DMC product in reaction back enters scrubber tower (23), making that methyl alcohol is water-soluble enters at the bottom of the tower and it is separated with methylcarbonate, methylcarbonate input DMC rectifying tower (24) is to the methylcarbonate rectification and purification, and the back methylcarbonate of purifying is exported after condenser condenses;
Five, Methanol Recovery
The methyl alcohol that generates in the scrubber tower (23) is squeezed into methanol rectifying tower (25) with pump, and the methyl alcohol that dilutes is carried out rectification and purification methyl alcohol, and the methyl alcohol after the rectifying enters methyl alcohol basin (19) behind condenser.
2. according to the described method of utilizing carbonic acid gas to prepare methylcarbonate of claim 1, it is characterized in that: in the described methyl alcohol synthesis step, at the bottom of methyl alcohol synthetic reactor (9) tower, discharge methanol aqueous solution feeding methyl alcohol primary tower (17), the cooling back feeds methanol rectifying tower (18) rectifying, rectifying obtains purer methyl alcohol through condensation, and it is standby to be collected in methyl alcohol basin (19) after the cooling.
3. according to the described method of utilizing carbonic acid gas to prepare methylcarbonate of claim 1, it is characterized in that: the methyl alcohol in the described methyl alcohol basin (19) is entering the preceding intermediate buffering jar (22) that is introduced into of DMC reactor (20).
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| CN102698567A (en) * | 2012-06-21 | 2012-10-03 | 华陆工程科技有限责任公司 | Method for removing organic matters and carbon dioxide in tail gas by using carbonic ester produced from carbon dioxide and fatty alcohol |
| CN103288645A (en) * | 2012-02-23 | 2013-09-11 | 亚申科技研发中心（上海）有限公司 | Method for separating dimethyl ether and recovering ammonia in co-production process for dimethyl carbonate and dimethyl ether via urea alcoholysis method |
| CN113443989A (en) * | 2021-06-29 | 2021-09-28 | 合肥工业大学 | Coupling CO2Method for synthesizing dimethyl carbonate and co-producing ethylene glycol |
| CN114160056A (en) * | 2021-12-07 | 2022-03-11 | 山东德普化工科技有限公司 | Device for circularly producing dimethyl carbonate |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103288645A (en) * | 2012-02-23 | 2013-09-11 | 亚申科技研发中心（上海）有限公司 | Method for separating dimethyl ether and recovering ammonia in co-production process for dimethyl carbonate and dimethyl ether via urea alcoholysis method |
| CN103288645B (en) * | 2012-02-23 | 2016-03-16 | 亚申科技研发中心（上海）有限公司 | Separation of dimethyl ether in the technique of alcoholysis of urea co-producing dimethyl carbonate and dme also reclaims the method for ammonia |
| CN102698567A (en) * | 2012-06-21 | 2012-10-03 | 华陆工程科技有限责任公司 | Method for removing organic matters and carbon dioxide in tail gas by using carbonic ester produced from carbon dioxide and fatty alcohol |
| CN113443989A (en) * | 2021-06-29 | 2021-09-28 | 合肥工业大学 | Coupling CO2Method for synthesizing dimethyl carbonate and co-producing ethylene glycol |
| CN114160056A (en) * | 2021-12-07 | 2022-03-11 | 山东德普化工科技有限公司 | Device for circularly producing dimethyl carbonate |
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Application publication date: 20100929 |