CN103304442B - Process for synthesizing diacetylmonoxime ethyl ether by continuous reactions in microtube - Google Patents
Process for synthesizing diacetylmonoxime ethyl ether by continuous reactions in microtube Download PDFInfo
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 67
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 title claims abstract description 61
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 title abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 50
- 239000003513 alkali Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000005516 engineering process Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000004853 microextraction Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 35
- 102000029749 Microtubule Human genes 0.000 claims description 27
- 108091022875 Microtubule Proteins 0.000 claims description 27
- 210000004688 microtubule Anatomy 0.000 claims description 27
- 238000000605 extraction Methods 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000013517 stratification Methods 0.000 claims description 9
- 238000013375 chromatographic separation Methods 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000007600 charging Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000004065 wastewater treatment Methods 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 29
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 4
- 229940008406 diethyl sulfate Drugs 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 2
- 239000012467 final product Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000001020 rhythmical effect Effects 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process for synthesizing diacetylmonoxime ethyl ether by continuous reactions in a microtube. In the process, diacetylmonoxime and diethyl sulfate are directly reacted to synthesize diacetylmonoxime ethyl ether in a condition that the temperature is 30-45 DEG C and the pressure is 0.1MPa in the presence of strong base with the adoption of a continuous reaction technology in the microtube, wherein the strong base is sodium hydroxide, potassium hydroxide or an alcamine compound. In the process, diethyl sulfate, the alkali liquor and diacetylmonoxime are respectively fed by a precise micro pump, wherein diacetylmonoxime sequentially mixed with the alkali liquor and diethyl sulfate reacts in a microtube reactor. The product through a heat exchanger is condensed and collected at low temperature, and is stewed and layered by a chromatographic separator. A water phase is extracted and separated by a micro extraction tower, and an oil phase containing diacetylmonoxime ethyl ether is rectified and purified by a rectifying tower, so that the final product diacetylmonoxime ethyl ether is obtained. The process is high in selectivity of diacetylmonoxime ethyl ether, mass transfer and heat transfer can be remarkably enhanced, and hydrolysis of diethyl sulfate is effectively avoided. The process is simple in process, long in stable transfer time, low in cost, easy to amplify and suitable for the industrialized production requirement.
Description
Technical field
The technique that the present invention relates to the micro-inner reaction tube synthesizing butanone oxime of a kind of serialization ether, belongs to fine chemical technology field.
Background technology
Oxime ether is the organic synthesis intermediate that a kind of added value is very high, can be for the synthesis of a series of medicine, agricultural chemicals product innovation.The direct synthesizing oxime ether of O-alkylation rhythmic reaction of oxime, adopts oxime and alkylating reagent to carry out under highly basic existence condition, reacts to have that system temperature is wayward, alkylating reagent utilization ratio is not high, the problem of unstable product quality.As use in the reaction of ethyl sulfate as ethylization reagent synthesizing butanone oxime ether [" Zhejiang chemical industry ", 2012], reaction conditions is that the ratio of the amount of substance of Diacetylmonoxime, ethyl sulfate and sodium hydroxide is 1:1.3:1, and ethyl sulfate time for adding is 1h, at 25 DEG C, reacts 8h.Although the yield of Diacetylmonoxime ether reaches 92.65%, because ethyl sulfate character is active, especially in water, easily decompose, in rhythmic reaction, need to adopt the method that slowly drips continuously ethyl sulfate to feed in raw material, complicated operation, wayward, the operating time is long, cost is high, and plant factor is low.Temperature of reaction system is easily ascended to heaven, and reaction may excessively be carried out, unstable product quality.Due to long reaction time, the complete excessive ethyl sulfate of unreacted almost all divides and takes off, and causes waste and the equipment corrosion of raw material.Do not meet the requirement of suitability for industrialized production.
In microtubule reactor, carry out building-up reactions and become new study hotspot in chemical engineering and synthetic chemistry field, but also have certain distance from industrial large-scale application.Compare with the chemical reaction carrying out in popular response device (as batch reactor), because the physical size of microtubule reactor is very little, be generally 10-3000 μ m, can improve mass transfer, driving force of heat transfer, significantly strengthen the flow pattern of quality and heat transfer process and improvement fluid.In micro equipment, owing to having reduced fluid thickness, corresponding specific surface area is significantly improved, and has strengthened reaction process and mass transfer, heat transfer simultaneously.In micro-reactive system, the strengthening of transmittance process can improve transformation efficiency, selectivity and the speed of reaction of product effectively.Adopt microtubule reaction technology, have reaction volume and greatly reduce, the reaction times also shortens greatly, and the security of equipment is improved significantly, and the throughput of unit time and unit volume exceedes the advantages such as batch process.Traditional reactor need to improve throughput by iodine equipment step by step, and microtubule reactor can be realized by the number that increases functional unit, can guarantee the security of operation.
Summary of the invention
The object of this invention is to provide a kind of defect that can overcome in rhythmic reaction, and energy consumption is low, the technique of the micro-inner reaction tube synthesizing butanone oxime of the serialization of excellent property ether.Its technology contents is:
A technique for the micro-inner reaction tube synthesizing butanone oxime of serialization ether, adopts reaction technology in serialization microtubule, is 30-45 DEG C in temperature, and pressure is under the condition of 0.1MPa and highly basic existence, and Diacetylmonoxime and ethyl sulfate are reacted to direct synthesizing butanone oxime ether; Highly basic is sodium hydroxide, potassium hydroxide or alcamine compound, and described serialization microtubule is microtubule reactor.
Ethyl sulfate, alkali lye and Diacetylmonoxime use respectively first, second, third precise micro pump charging, Diacetylmonoxime reacts after the first micro mixer, the second micro mixer mix with alkali lye and ethyl sulfate successively in the microtubule reactor with temperature regulator, product cryogenic condensation after interchanger is collected, chromatographic separation device stratification, water, through micro-extraction tower extracting and separating, obtains finished product Diacetylmonoxime ether containing the oil phase product of Diacetylmonoxime ether through rectifying tower rectification and purification.
Described microtubule reactor inside diameter is 1mm-2.1mm.
The residence time is 3min-3h.
Described Diacetylmonoxime, ethyl sulfate and alkali lye uses the charging of precise micro pump, and Diacetylmonoxime is 1:(1-1.25 with the ratio of the amount of substance of ethyl sulfate, highly basic): (1-1.15).
Described Diacetylmonoxime mixes through micro mixer with alkali lye and ethyl sulfate successively, after mixing, forms stable liquid-liquid plug flow.
Described the first micro mixer, the second micro mixer is selected from T-shaped mixing tank and SIMM-V2 type micro mixer.
Described extraction agent is selected from ether, methyl tertiary butyl ether, toluene.
Described extraction agent is through the recycling use of extraction agent recovery tower.
After rectifying, the complete reaction raw materials of unreacted reclaims and uses.
The water obtaining after chromatographic separation enters production wastewater treatment system after reclaiming Diacetylmonoxime metal-salt and alkali.
Compared with prior art, tool has the following advantages in the present invention:
(1), in reaction, without slowly dripping ethyl sulfate, operating time and cost have been reduced;
(2) in continuous microtubule reaction process, mass transfer and heat transfer process are strengthened greatly, in reactor, material concentration keeps substantially constant substantially, reacting balance, reduce the decomposition of the ethyl sulfate producing because of excessive concentration in traditional reactor, reduce the side reaction that local temperature is crossed thermal initiation, improved quality product;
(3) in continuous microtubule reaction process, form stable liquid-liquid plug flow and flow, the steady running time is long;
(4) after reaction finishes, organism and the complete reaction raw materials of unreacted remaining in water product obtain efficient recovery;
(5) flow process is simple, easy to operate, is easy to amplify, and meets industrialization production requirements.
Brief description of the drawings
Fig. 1 is the process flow sheet of the micro-inner reaction tube synthesizing butanone oxime of serialization ether.
In figure, ethyl sulfate 1, alkali lye 2, Diacetylmonoxime 3, the first precise micro pump (ethyl sulfate fresh feed pump) 4, the second precise micro pump (alkali lye fresh feed pump) 5, the 3rd precise micro pump (Diacetylmonoxime fresh feed pump) 6, the first micro mixer 7, the second micro mixer 8, reactor 9 in microtubule with temperature regulator, interchanger 10, chromatographic separation device 11, micro-extraction tower 12, Diacetylmonoxime ether product 13, rectifying tower 14, extraction agent 15, extraction agent recovery tower 16, the reaction raw materials 17 that unreacted is complete, the water 18 obtaining after chromatographic separation, finished product Diacetylmonoxime ether 19.
Embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is described further.
The method of the micro-inner reaction tube synthesizing butanone oxime of serialization ether, adopts reaction technology in serialization microtubule, is 30-45 DEG C in temperature, and pressure is under the condition of 0.1MPa and highly basic existence, and Diacetylmonoxime and ethyl sulfate are reacted to direct synthesizing butanone oxime ether.Adopt the direct synthesizing butanone oxime ether of reaction technology in serialization microtubule, significantly reinforcing mass transfer and heat transfer, can reduce reducing side reaction of ethyl sulfate, and flow process is simple, and the steady running time is long, with low cost, is easy to amplify, and meets industrialization production requirements.
Ethyl sulfate 1, alkali lye 2, Diacetylmonoxime 3 uses respectively the first precise micro pump (ethyl sulfate fresh feed pump) 4, the second precise micro pump (alkali lye fresh feed pump) 5, the 3rd precise micro pump (Diacetylmonoxime fresh feed pump) 6 chargings, Diacetylmonoxime successively with alkali lye and ethyl sulfate through the first micro mixer 7, after mixing, the second micro mixer 8 in reactor 9, reacts in the microtubule with temperature regulator, product is through interchanger 10 cryogenic condensation collecting reaction products, obtain the oil phase containing Diacetylmonoxime ether product through chromatographic separation device 11 stratification, residual Diacetylmonoxime ether in water, Diacetylmonoxime and ethyl sulfate etc. reclaim with 12 extractions of micro-extraction tower.Oil phase product 13 use rectifying tower 14 rectification and purification containing Diacetylmonoxime ether product obtain finished product Diacetylmonoxime ether 19.Extraction agent 15 is by 16 recycling uses of extraction agent recovery tower.After rectifying, the complete reaction raw materials 17 of unreacted can be realized reclaiming and use.The water 18 obtaining after chromatographic separation can enter production wastewater treatment system after reclaiming Diacetylmonoxime metal-salt and alkali.
embodiment 1
Adopting microtubule reactor inside diameter is 2.1mm, length 5m.
Diacetylmonoxime, ethyl sulfate, 18% aqueous sodium hydroxide solution are taking the ratio of amount of substance as 1:1.25:1.15.Continuously feeding, temperature of reaction is 30 DEG C, the residence time is 20min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction.Product carries out gas chromatographic analysis with GC1690 type gas chromatograph.Chromatographic column is that (specification: 30m × 0.32mm × 0.25 μ is type capillary column m), fid detector carry out quantitative Analysis to GsBP-INOWAX taking propyl carbinol as internal standard substance.Analytical procedure, lower same.The transformation efficiency of Diacetylmonoxime is 83.41%, and the yield of Diacetylmonoxime ether is 16.80%, and selectivity is 16.80%.
embodiment 2
Adopting microtubule reactor inside diameter is 2.1mm, length 5m.
Diacetylmonoxime, ethyl sulfate, 18% aqueous sodium hydroxide solution are taking the ratio of amount of substance as 1:1:1.Continuously feeding, temperature of reaction is 30 DEG C, the residence time is 3min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction, product gas chromatographic analysis.The transformation efficiency of Diacetylmonoxime is 87.64%, Diacetylmonoxime ether yield be 15.81%, selectivity is 18.04%.
embodiment 3
Adopting microtubule reactor inside diameter is 1mm, length 20m.
Diacetylmonoxime, ethyl sulfate, 18% aqueous sodium hydroxide solution are taking the ratio of amount of substance as 1:1:1.Continuously feeding, temperature of reaction is 40 DEG C, the residence time is 60min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction, product gas chromatographic analysis.The transformation efficiency of Diacetylmonoxime is 77.87%, Diacetylmonoxime ether yield be 53.10%, selectivity is 68.19%.
embodiment 4
Adopting microtubule reactor inside diameter is 1mm, length 60m.
Diacetylmonoxime, ethyl sulfate, 18% aqueous sodium hydroxide solution are taking the ratio of amount of substance as 1:1:1.Continuously feeding, temperature of reaction is 45 DEG C, the residence time is 180min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction, product gas chromatographic analysis.The transformation efficiency of Diacetylmonoxime is 74.86%, Diacetylmonoxime ether yield be 43.49%, selectivity is 45.94%.
embodiment 5
Adopting reactor inside diameter in microtubule is 1mm, length 20m.
Diacetylmonoxime, ethyl sulfate, 30% potassium hydroxide aqueous solution are taking the ratio of amount of substance as 1:1:1 continuously feeding, and temperature of reaction is 45 DEG C, and the residence time is 30min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction, product gas chromatographic analysis.The transformation efficiency of Diacetylmonoxime is 82.56%, Diacetylmonoxime ether yield be 55.03%, selectivity is 66.65%.
embodiment 6
Adopting reactor inside diameter in microtubule is 1mm, length 20m.
Diacetylmonoxime, ethyl sulfate, trolamine are taking the ratio of amount of substance as 1:1:1 continuously feeding, and temperature of reaction is 45 DEG C, and the residence time is 30min.Utilize cryogenic condensation collecting reaction product, product is got oil phase through stratification, and the remaining organism in water reclaims with extraction agent extraction, product gas chromatographic analysis.The transformation efficiency of Diacetylmonoxime is 72.70%, Diacetylmonoxime ether yield be 24.11%, selectivity is 33.16%.
The result of above-described embodiment 1 to 6 is as shown in table 1 below:
Table 1 embodiment result table look-up
In above-described embodiment, described microtubule reactor inside diameter is 1mm, 2.1mm, between specification be suitable for as 1.6 mm those skilled in the art will know that also, but do not give an example here.In above-described embodiment; ketoxime is that 1:1:1 is more excellent embodiment with the ratio of the amount of substance of ethyl sulfate, highly basic; but 1:(1-1.25): (1-1.15) those skilled in the art will know that also and be suitable for, comprise that other predictable distortion on open basis of the present invention is all within protection scope of the present invention.
Claims (9)
1. the technique of the micro-inner reaction tube synthesizing butanone oxime of a serialization ether, it is characterized in that adopting reaction technology in serialization microtubule, be 30-45 DEG C in temperature, pressure is under the condition of 0.1MPa and highly basic existence, and Diacetylmonoxime and ethyl sulfate are reacted to direct synthesizing butanone oxime ether; Highly basic is sodium hydroxide, potassium hydroxide or alcamine compound, and described serialization microtubule is microtubule reactor;
Ethyl sulfate, alkali lye and Diacetylmonoxime use respectively first, second, third precise micro pump charging, Diacetylmonoxime reacts after the first micro mixer, the second micro mixer mix with alkali lye and ethyl sulfate successively in the microtubule reactor with temperature regulator, product cryogenic condensation after interchanger is collected, chromatographic separation device stratification, water, through micro-extraction tower extracting and separating, obtains finished product Diacetylmonoxime ether containing the oil phase product of Diacetylmonoxime ether through rectifying tower rectification and purification; Described Diacetylmonoxime mixes through micro mixer with alkali lye and ethyl sulfate successively, after mixing, forms stable liquid-liquid plug flow.
2. technique as claimed in claim 1, is characterized in that described microtubule reactor inside diameter is 1mm-2.1mm.
3. technique as claimed in claim 1, is characterized in that the residence time is 3min-3h.
4. technique as claimed in claim 1, is characterized in that described Diacetylmonoxime, ethyl sulfate and alkali lye use the charging of precise micro pump, and Diacetylmonoxime is 1:(1-1.25 with the ratio of the amount of substance of ethyl sulfate, highly basic): (1-1.15).
5. technique as claimed in claim 1, is characterized in that described the first micro mixer, the second micro mixer are selected from T-shaped mixing tank and SIMM-V2 type micro mixer.
6. technique as claimed in claim 1, is characterized in that the extraction agent that described extraction adopts is selected from ether, methyl tertiary butyl ether, toluene.
7. technique as claimed in claim 1, is characterized in that described extraction agent is through the recycling use of extraction agent recovery tower.
8. technique as claimed in claim 1, is characterized in that after rectifying, and the complete reaction raw materials of unreacted reclaims and uses.
9. technique as claimed in claim 1, is characterized in that the water obtaining after chromatographic separation enters production wastewater treatment system after reclaiming Diacetylmonoxime metal-salt and alkali.
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| CN111974324A (en) * | 2020-09-17 | 2020-11-24 | 苏州昊帆生物股份有限公司 | Continuous preparation device of ethionamide and method for preparing ethionamide |
| CN114307893B (en) * | 2020-09-30 | 2023-10-31 | 沈阳化工研究院有限公司 | Reaction device and process method suitable for continuous synthesis of fluorescent whitening agent |
| CN114591197A (en) * | 2022-03-01 | 2022-06-07 | 浙江圣安化工股份有限公司 | Process method for continuously synthesizing oxime ether |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101224405A (en) * | 2007-10-18 | 2008-07-23 | 清华大学 | Reactor or mixer with micromesh structure |
| CN102911079A (en) * | 2011-08-02 | 2013-02-06 | 宁波欧迅化学新材料技术有限公司 | Method of using ketoxime ether for preparation of alkoxyl amine hydrochloride and alkoxyl amine hydrochloride preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101224405A (en) * | 2007-10-18 | 2008-07-23 | 清华大学 | Reactor or mixer with micromesh structure |
| CN102911079A (en) * | 2011-08-02 | 2013-02-06 | 宁波欧迅化学新材料技术有限公司 | Method of using ketoxime ether for preparation of alkoxyl amine hydrochloride and alkoxyl amine hydrochloride preparation method |
Non-Patent Citations (2)
| Title |
|---|
| 丁酮肟法制备乙氧胺的新工艺研究;俞勇等;《浙江化工》;20121231;第43卷(第9期);35-36、34 * |
| 俞勇等.丁酮肟法制备乙氧胺的新工艺研究.《浙江化工》.2012,第43卷(第9期),35-36、34. |
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