CN103214393A - Oximation method of ketone - Google Patents
Oximation method of ketone Download PDFInfo
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- CN103214393A CN103214393A CN2013101505738A CN201310150573A CN103214393A CN 103214393 A CN103214393 A CN 103214393A CN 2013101505738 A CN2013101505738 A CN 2013101505738A CN 201310150573 A CN201310150573 A CN 201310150573A CN 103214393 A CN103214393 A CN 103214393A
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Abstract
The invention discloses an oximation method of ketone. The method is to carry out an oximation reaction on ketone, ammonia and hydrogen peroxide in the presence of catalysts and solvents. The method is characterized in that a reactor 1 comprises a reaction area and a separation area, wherein most of catalyst particles in a reaction liquid are settled in the separation area and return to the reaction area; the reaction liquid containing a small amount of catalyst grains at the upper part of the separation area flows into an external filter 4 to be subjected to liquid-solid separation; a filtered clear liquid enters a next procedure; after being pressurized by a circulation pump 5 and is cooled by a circulation cooler 6, the filtered reaction liquid containing the catalyst is sufficiently mixed with external materials in a static mixer 7 and is fed back to the reactor 1. By utilizing the oximation method, the external liquid amount and the content of the catalyst in the circulation liquid are reduced to a large extent, the consumption of the catalyst and the operation cost of the device are effectively reduced, and the investment on the external filter, the circulation pump and the circulation cooler is saved.
Description
Technical field
The present invention relates to a kind of oximation process of ketone.Especially pimelinketone, acetone, butanone are distinguished the method that oximate is produced cyclohexanone-oxime, acetoxime, Diacetylmonoxime.
Background technology
Hexanolactam is a main raw material of producing nylon fibre and engineering plastics, and the preparation of cyclohexanone-oxime is the committed step of producing hexanolactam.At present, the method for preparing cyclohexanone-oxime mainly contains Raschig process, NO catalytic reduction method, phosphatic hydroxylamine method, amidoxime method.Wherein, the amidoxime method with its preparation method simply, the advantage of by-product sulphur ammonium not, become the main flow of hexanolactam device development in recent years, the improvement research of relevant cyclohexanone oxamidinating process is still carried out continuing.
Acetoxime and Diacetylmonoxime are mainly used in oxygen scavenging chemical etc.Industrial traditional processing technology mainly contains oxammonium hydrochloride method, oxammonium sulfate method and sodium nitrite method at present.These three kinds of technologies not only complex process, Production Flow Chart is long, facility investment is high, have more serious corrosion and pollution problem, and the hydrochloride of a large amount of low values of association or vitriol byproduct.In the novel process that acetoxime and Diacetylmonoxime are produced, the most representative is that the direct oximate of acetone or butanone prepares acetoxime or Diacetylmonoxime, have transformation efficiency and selectivity height, by product is few, environmentally friendly and the technology characteristic of simple, and the trend that replaces traditional technology is arranged.
Chinese patent ZL02100227.4 discloses the separation method of HTS in a kind of ketone oxamidinating reaction system.Use external settling vessel to realize that HTS separates with the continuous of reaction product ketoxime in this technical scheme.
Chinese patent ZL02100228.2 discloses the method that a kind of cyclohexanone oxamidinating prepares cyclohexanone-oxime.Use external settling vessel to realize that HTS separates with the continuous of reaction product ketoxime in this technical scheme.
Chinese patent ZL200510133880.0 discloses a kind of preparation method of cyclohexanone-oxime.The claim of this technical scheme mainly is that reaction mixture forms cycling stream, and the adding location schemes of pimelinketone, ammonia, hydrogen peroxide on the reactor, does not relate to the separation scheme of reaction mass and catalyzer.
Chinese patent application CN200810227656.1 has announced the Ammoximation reaction of a kind of ketone or aldehyde.What adopt is that reacting slurry carries out multistage liquid-solid the separation through wet cyclone with mineral membrane or metal sintering pipe, and wet cyclone and mineral membrane or metal sintering pipe etc. are the reactor outer filter in this patent, and after all being arranged on recycle pump.
Chinese patent ZL201020046146.7 discloses a kind of cyclohexanone oxamidinating reactor.The core of this patent is by being installed in the film filter of Ammoximation reaction device inside, finishes separating of filtrate and catalyzer.
Chinese patent ZL201120054873.2 discloses a kind of cyclohexanone oxamidinating catalysts tripping device.The principal feature of this technical scheme is that the built-in and external strainer series connection of reactor secondary filters step by step, and the filtrate of built-in filter is directly sent into external strainer and further filtered, and the film pore footpath of external filter film tube aperture ratio built-in filter is little.
Chinese patent application CN201110209393.3 discloses the Ammoximation reaction device of producing cyclohexanone-oxime, and claim mainly is the structure of inside reactor, comprises inner filtering system, liquefied ammonia vaporizing coil, ring distributor, column drainage tube etc.
Chinese patent application CN201210016278.9 discloses the method that a kind of cyclohexanone oxamidinating prepares cyclohexanone-oxime, it is characterized in that: by reactant outer circulation heat-obtaining mode control reaction temperature, reaction product is separated in strainer with HTS.This scheme also is by external strainer is set behind recycle pump, finishes separating of filtrate and catalyzer.
Chinese patent ZL201220142109.5 discloses a kind of external mineral membrane amidoxime catalyzed reaction tripping device, reaction mass carries out systemic circulation between retort, charging pump, external mineral membrane cross-flow filter, mixing tank, wherein a part of material carries out partial circulating in formations such as feeding pipeline, recycle pump, external mineral membrane cross-flow filter, partial circulating pipeline closed circuit.This scheme also is by external strainer is set behind recycle pump, finishes separating of filtrate and catalyzer, and does not relate to the scheme that removes reaction heat.
Chinese patent ZL201220294588.2 relates to a kind of cyclohexanone oxamidinating catalyzer dynamic separation device.This technical scheme realizes separating of catalyzer and feed liquid by the video disc film filtering element in the dynamic separator tank body, and this scheme also is by dynamic separator is set behind recycle pump, finishes separating of filtrate and catalyzer, and does not relate to the scheme that removes reaction heat.
Chinese patent application CN201210328123.9 relates to a kind of method for preparing the reactive system catalyzer filtering separation of cyclohexanone-oxime, and the core of this method is that reactive system catalyzer filtering separation is to adopt catalyzer preseparator and two steps of catalyzer accurate filter to combine to finish whole sepn processes continuously.After this scheme is arranged on recycle pump with the catalyzer preseparator, and do not relate to the scheme that removes reaction heat.
Chinese patent application CN200410018607.9 relates to the technology of a kind of acetone or butanone oxidation production acetoxime or Diacetylmonoxime.Mainly lay particular emphasis on description, do not comprise concrete technology and describe reaction parameter.
Chinese patent application CN201110374542.1 relates to a kind of device for preparing acetoxime, comprises condenser, integral reactor, outer circulation pump.Wherein integral reactor is the turriform reactor.
Chinese patent application CN201010229701.4 relates to a kind of method for preparing acetoxime, it is characterized in that acetone contacts in the presence of solvent, oxygenant, tensio-active agent and catalyzer with ammonia.Claim mainly is to solvent, oxygenant, tensio-active agent and selection of catalysts.
In the full scale plant, generally all adopt membrane filtration to reach the purpose of reaction solution and catalyst separating at present.Because catalyst concn higher (about 4%wt) in the reactive system, and because the impact and the abrasion of agitator paddle, circulating pump impeller, duct wall and appts wall in the reactive system, catalyzer is than cracky, cause filter element to stop up easily, so strainer needs regularly to switch, so that back flushing or regenerated offline.
In the above document, the scheme that has adopts built-in filter, is arranged in the reactor, and this scheme exists cleans the inconvenient more shortcoming of renew cartridge difficulty that reaches; The scheme that has then adopts external strainer, is arranged on outlet of circulating pump, catalyst content height in the reaction solution, and the time that this scheme strainer regularly switches is shorter.
Summary of the invention
The present invention is directed to the deficiency that prior art exists, a kind of oximation process of ketone preferably is provided.
The present invention has announced a kind of oximation process of ketone, is in the presence of catalyzer and solvent, and ketone, ammonia and hydrogen peroxide carry out oximation reaction.Described ketone is selected from pimelinketone or acetone or butanone, and the oximate product is respectively cyclohexanone-oxime or acetoxime or Diacetylmonoxime.This method comprises reactor 1, external strainer 4, recycle pump 5, recirculation cooler 6, static mixer 7 and attached pipe fitting.
Reactor 1 is made up of reaction zone and disengaging zone.Reaction zone is positioned at reactor 1 bottom, and inside has guide shell 9 and agitator 10, reaction solution in the inside and outside interregional pump circulation of guide shell 9 to react fully.The disengaging zone is positioned at reactor 1 top, and inside has weir 2 and catalyzer backward channel 3, and reaction solution keeps certain residence time in weir 2, allows most of granules of catalyst settles down in the reaction solution, returns reaction zone by catalyzer backward channel 3.
The reaction zone outer wall has chuck 8, internal guide cylinder 9 can be selected from double-layered cylinder, cylinder shape coil pipe or their combination of internal solid cylinder, interlayer hollow, if select the double-layered cylinder or the cylinder shape coil pipe of interlayer hollow for use, when leading to water coolant in interlayer or the coil pipe, then guide shell 9 has the function of cooling off reaction solution, part or all of reaction heat can be removed out reactive system; In interlayer or the coil pipe during logical steam, can heating use when driving.Increase the heat interchanging area of chuck 8 and guide shell 9, reaction heat partly or entirely can be removed out reactive system, then can reduce or cancel recirculation cooler 6.
Weir, disengaging zone 2 includes the reaction solution of minor amount of catalyst particles, flows into external strainer 4 from reaction solution outlet 11 and carries out liquid-solid separation, and filter back clear liquid enters next step operation; The reaction solution that contains catalyzer after the filter and adds material send reactor 1 back to behind static mixer 7 thorough mixing after recycle pump 5 superchargings and recirculation cooler 6 coolings.
React employed catalyst grain size at 1-200 μ m.External strainer 4 is arranged between reactor 1 and the recycle pump 5, and it is a kind of candle filter, and separate unit or many series/parallel combinations can be set.Filter core 4 is the metal powder sintering membrane pipe, and the filtering rejection of its percolation is 100%, and material is selected from 300 series stainless steels, Inconel(nickel alloys), nickel, Monel 400, Hastelloy C276, iron aluminium or other nickelic/Chrome metal powder.
Solvent, ammonia, ketone, hydrogen peroxide can add on the circulation line between recirculation cooler 6 and the static mixer 7, and also a plurality of reserved opening 12 that can be provided with on reactor 1 add respectively.Described recycle pump 5 can be separate unit or many parallel connections, and the separate unit flow is at 200-1200m
3/ h, solids content is at 0.5-16%wt in the loop slurry.
The present invention adopts the method that the disengaging zone is set at inside reactor, most of catalyzer is rested on participate in reaction in the reactor, reduce the catalytic amount of bringing external circulating system into, alleviated the working load of external strainer, prolonged the switching time of strainer back flushing and regenerated offline; Also reduce simultaneously the damaged probability in the catalyzer working cycle outside, when the shortening reactive system is operated non-cutting time, reduced the loss of catalyzer, reduced device running cost.
The present invention also is provided with the guide shell that can have cooling effect concurrently when reaction zone is provided with chuck, strengthened the ability that reactor removes reaction heat, can effectively reduce even cancel the outer circulation interchanger; Remove thermal load in the outer circulation when reducing,, can suitably reduce external strainer and recycle pump, can reduce the investment of external strainer, pump and recirculation cooler significantly, also help saving energy and reduce the cost because catalyst content reduces in the outer circulation reaction solution.
Description of drawings
Fig. 1 is a process flow diagram of the present invention.
Among the figure: 1, reactor; 2, weir; 3, catalyzer backward channel; 4, external strainer; 5, recycle pump; 6, recirculation cooler; 7, static mixer; 8, chuck; 9, guide shell; 10 agitators; 11, reaction solution outlet; 12, reserved opening.
Embodiment
Following examples are intended to illustrate the present invention rather than limitation of the invention.The present invention can implement by the described arbitrary mode of summary of the invention.
With 100,000 tons of/year pimelinketone oximate reaction process flow processs is example, as shown in Figure 1, in the presence of concentration 4%wt catalyzer, solvent, ammonia, circulation fluid and the hydrogen peroxide mouth of pipe from the reactor 1 respectively add, participate in the pump circulation in the reaction zone, pimelinketone adds on the circulation fluid pipeline.Pimelinketone, ammonia and hydrogen peroxide carry out oximation reaction in reactor 1.Reaction solution self-separation district flows into external strainer 4 and carries out liquid-solid separation, and filter back clear liquid enters next step operation; The reaction solution that contains catalyzer after the filter and adds pimelinketone and sends back in the reactor 1 behind static mixer 7 thorough mixing after recycle pump 5 superchargings and recirculation cooler 6 coolings.
Claims (6)
1. the oximation process of a ketone is that ketone, ammonia and hydrogen peroxide carry out the method for oximation reaction in the presence of catalyzer and solvent, it comprises reactor (1), external strainer (4), recycle pump (5), recirculation cooler (6), static mixer (7) and attached pipe fitting is characterized in that:
A, reactor (1) are made up of reaction zone and disengaging zone, and reaction zone is positioned at reactor (1) bottom, and inside has guide shell (9) and agitator (10), and outer wall has chuck (8); The disengaging zone is positioned at reactor (1) top, inside has weir (2) and catalyzer backward channel (3), have reaction solution outlet (11), most of granules of catalyst settles down in the disengaging zone in the reaction solution, returns reaction zone by catalyzer backward channel (3);
B, the reaction solution autoreaction liquid outlet (11) that contains minor amount of catalyst particles flow to the further liquid-solid separation of external strainer (4) certainly, and filter back clear liquid enters next step operation; The reaction solution that contains catalyzer after the filter and adds material send reactor (1) back to behind static mixer (7) thorough mixing after recycle pump (5) supercharging and recirculation cooler (6) cooling;
C, in agitator (10) effect down, reaction solution is interregional pump circulation inside and outside guide shell (9).
2. the oximation process of ketone according to claim 1, it is characterized in that: employed catalyst grain size is at 1-200 μ m.
3. the oximation process of ketone according to claim 1, it is characterized in that: guide shell (9) can be double-layered cylinder or the cylinder shape coil pipe or their combination of internal solid cylinder or interlayer hollow.
4. the oximation process of ketone according to claim 1, it is characterized in that: external strainer (4) is a kind of candle filter, and separate unit or many series/parallels combinations can be set.
5. according to the oximation process of claim 1,4 described ketone, it is characterized in that: the filter core of external strainer (4) is the metal powder sintering membrane pipe, and material is selected from 300 series stainless steels or Inconel(nickel alloys) or nickel or Monel 400 or Hastelloy C276 or iron aluminium or other nickelic/Chrome metal powder.
6. the oximation process of ketone according to claim 1, it is characterized in that: described ketone is pimelinketone or acetone or butanone, and the oximate product is respectively cyclohexanone-oxime or acetoxime or Diacetylmonoxime.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103551087A (en) * | 2013-11-08 | 2014-02-05 | 神马实业股份有限公司 | Ammoximation reaction system for preparing cyclohexanone-oxime |
| CN103949191A (en) * | 2014-05-13 | 2014-07-30 | 湖北三宁化工股份有限公司 | Device and method for continuously adding catalysts in cyclohexanone oximation reaction |
| CN104001461A (en) * | 2014-04-24 | 2014-08-27 | 金华精锐制药机械有限公司 | Detachable multifunctional kettle internal jacket easy to clean |
| CN107362765A (en) * | 2017-09-04 | 2017-11-21 | 阳煤集团太原化工新材料有限公司 | Oximation reaction feeding regulating device and adjusting method |
| CN109382071A (en) * | 2018-12-13 | 2019-02-26 | 上海释颉化工技术合伙企业(有限合伙) | A kind of combined type generation reactor being used to prepare hexamethylene diamine |
| CN110394134A (en) * | 2019-08-28 | 2019-11-01 | 沧州旭阳化工有限公司 | Cooling system |
| CN112174850A (en) * | 2019-10-11 | 2021-01-05 | 福建天辰耀隆新材料有限公司 | Cyclohexanone oxime preparation system and preparation method |
| CN112759530A (en) * | 2020-12-30 | 2021-05-07 | 河北美邦工程科技股份有限公司 | Large-scale cyclohexanone-oxime production device and method |
| CN115069184A (en) * | 2022-05-31 | 2022-09-20 | 南通联升电力科技有限公司 | Continuous saponification control system based on distributed IO |
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| CN103551087A (en) * | 2013-11-08 | 2014-02-05 | 神马实业股份有限公司 | Ammoximation reaction system for preparing cyclohexanone-oxime |
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| CN104001461A (en) * | 2014-04-24 | 2014-08-27 | 金华精锐制药机械有限公司 | Detachable multifunctional kettle internal jacket easy to clean |
| CN103949191A (en) * | 2014-05-13 | 2014-07-30 | 湖北三宁化工股份有限公司 | Device and method for continuously adding catalysts in cyclohexanone oximation reaction |
| CN107362765A (en) * | 2017-09-04 | 2017-11-21 | 阳煤集团太原化工新材料有限公司 | Oximation reaction feeding regulating device and adjusting method |
| CN109382071A (en) * | 2018-12-13 | 2019-02-26 | 上海释颉化工技术合伙企业(有限合伙) | A kind of combined type generation reactor being used to prepare hexamethylene diamine |
| CN110394134A (en) * | 2019-08-28 | 2019-11-01 | 沧州旭阳化工有限公司 | Cooling system |
| CN110394134B (en) * | 2019-08-28 | 2024-04-19 | 沧州旭阳化工有限公司 | Cooling system |
| CN112174850A (en) * | 2019-10-11 | 2021-01-05 | 福建天辰耀隆新材料有限公司 | Cyclohexanone oxime preparation system and preparation method |
| CN112759530A (en) * | 2020-12-30 | 2021-05-07 | 河北美邦工程科技股份有限公司 | Large-scale cyclohexanone-oxime production device and method |
| CN112759530B (en) * | 2020-12-30 | 2022-11-11 | 河北美邦工程科技股份有限公司 | Large-scale cyclohexanone-oxime production device and method |
| CN115069184A (en) * | 2022-05-31 | 2022-09-20 | 南通联升电力科技有限公司 | Continuous saponification control system based on distributed IO |
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