CN105237409A - Method used for reductive amination using jet reactor - Google Patents
Method used for reductive amination using jet reactor Download PDFInfo
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- CN105237409A CN105237409A CN201410246202.4A CN201410246202A CN105237409A CN 105237409 A CN105237409 A CN 105237409A CN 201410246202 A CN201410246202 A CN 201410246202A CN 105237409 A CN105237409 A CN 105237409A
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006268 reductive amination reaction Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000002347 injection Methods 0.000 claims abstract description 33
- 239000007924 injection Substances 0.000 claims abstract description 33
- 238000005576 amination reaction Methods 0.000 claims abstract description 21
- 230000009467 reduction Effects 0.000 claims abstract description 21
- 230000002829 reductive effect Effects 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 hydride azo compound Chemical class 0.000 claims abstract description 7
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract description 3
- 150000002832 nitroso derivatives Chemical class 0.000 claims abstract description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 230000009849 deactivation Effects 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000004907 flux Effects 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000012141 concentrate Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method used for reductive amination using a jet reactor, and belongs to the field of chemical technology. According to the method, the jet reactor is adopted. The jet reactor comprises a reactor, an ejector, a circulating pump, a concentration device, a heat exchanger, and a mixer. The jet reactor is used for chemical product hydrogenation reduction. According to the method, a mixture containing a catalyst, raw materials, and a target amination product is taken as a dynamic fluid, high speed liquid flow is obtained via injection, and stable turbulent flow is formed at a nozzle, and in addition, negative pressure is formed around the nozzle, entrainment of hydrogen is realized, and gas-liquid-solid complete mixing reaction is realized. After reaction, and obtained product is subjected to condensation separation so as to obtain partially aminated products; a concentrate containing the catalyst and a reduced material are subjected to preheating using the heat exchanger, and mixing using the mixer, and then are delivered into the ejector for circular reaction. The method can be used for obtaining amines via reduction of nitro compounds, nitroso compounds, azo-compounds, azoxy compounds, and hydride azo compound.
Description
Technical field
The present invention relates to a kind of instrument and supplies method of liquid-phase hydrogenatin reduction amination, belong to chemical engineering process and equipment technical field.
Background technology
Aminated compounds is important Organic Chemicals and Chemicals, as: aniline, 4-ADPA etc., the Chemicals obtained by it and intermediate have kind more than 300, have a wide range of applications in the industries such as dyestuff, medicine, agricultural chemicals, explosive, spices, thiofide, exploitation prospect is very wide.
Shortening method is carried out owing to can make reaction orientation, and side reaction is few, good product quality, and productive rate is high, is therefore the developing direction that amine is produced, all can adopts hydrogenating reduction to containing nitro, nitroso-group, azoxy and hydrodiazo based compound.The method of current realization of industrialization reduction amination is mainly divided into gas phase hydrogenation method and By Liquid-phase Hydrogenation Process.Gas phase hydrogenation method is only applicable to the material of lower, the easy gasification of boiling point, and energy consumption is higher; By Liquid-phase Hydrogenation Process is not by the restriction being reduced boiling point substance, and the scope of application is wider, has the advantages such as temperature of reaction is low, side reaction is few, catalysis load is high, equipment capacity is large, gross investment is low, has caused the concern of people in recent years.
The injection reactor being applicable to solution-air or gas-liquid-solid reaction is proposed by Flugel the earliest, and its principle of work utilizes flow at high speed to go mutually to entrainment other phase, makes each phase close contact, produce violent stirring, reach well-mixed effect to complete reaction.The VanDierendonck detailed analysis excellent properties of injection reactor, and point out that this reactor replaces the first-selection that stirred reactor becomes heterophase reactor, there is many uniquenesses, excellent performance: 1. mass-transfer performance is good; 2. efficiency of conducting heat is large; 3. turndown ratio and working volume large; 4. unit volume power input is large; 5. structure is simple, without stirring part, is easy to the continuous of reaction process; 6. good seal performance; 7. be easy to engineering amplify.Research subsequently for injection reactor is never interrupted, and injection reactor is paid close attention to widely by as a kind of novel heterophase reactor in recent years.
Chemithon company of the U.S. obtained the patent of jet sulfonation reactor in about 1975, be used in sulfonation industrial production by injection reactor the earliest, and achieved good effect.China has also carried out the related application research of injection reactor successively, such as: patent CN201020001010.4 discloses a kind of injection circulation reactor for the preparation of polyoxyether, patent CN200910228980.X discloses a kind of method utilizing injection circulation reactor to prepare organic isocyanate.
Injection reactor makes reactant fully mix, and is conducive to reinforcing mass transfer and heat transfer, accelerates speed of reaction, improves concentration and temperature distribution, suppresses side reaction, improves the selectivity of reaction.Therefore, research and development novel injection reaction unit has broad application prospects, and especially in solution-air, the heterogeneous reaction field such as gas-liquid-solid, embodies numerous excellent properties than other heterophase reactor.
Summary of the invention
The object of the invention is problem that is high for energy consumption during prior art reduction amination, low conversion rate, provide a kind of adopt injection reactor to carry out liquid-phase hydrogenatin reduction amination device and processing method.There is reactor turndown ratio large, reaction-ure conversion-age and selectivity high, catalyst levels is few, the life-span is long, less investment, low power consumption and other advantages.
Technical scheme of the present invention: utilize injection reactor to carry out the method for reduction amination, comprise nitro-compound, nitroso compound, azo-compound, azoxy compound, hydrogenated azo compound obtains the method for amine through reduction, it is characterized in that by spraying reaction unit as follows to carry out: spray reaction unit and comprise reactor, injector, recycle pump, concentrating unit, interchanger and mixing tank, wherein, injector is by nozzle, reception chamber forms, nozzle is connected with screw thread or flange with reactor head, reception chamber is fixed on reactor wall, distance between nozzle and reception chamber is fixed or adjustable, the reactor head of described injection reaction unit arranges gas inlet and catalyst inlet, in reactor, heat-exchanger rig is set, reactor bottom is provided with material outlet, and connect recycle pump, concentrating unit, interchanger and mixing tank successively with pipeline, and material inlet is set between interchanger and concentrating unit.
First with the air in nitrogen replacement whole process, then with the nitrogen in hydrogen exchange whole process, again the target amination reaction mixture adding catalyzer is added in reactor by reactor head entrance, start recycle pump and interchanger, make material at injection reaction unit internal recycle, and to control reactor pressure be 0.5 ~ 3.0MPa.
Heating medium is passed in heat-exchanger rig and interchanger in reactor, controlling reactor temperature is 20 ~ 300 DEG C, thing will be reduced by the material inlet arranged between interchanger and concentrating unit to add, injector is entered after interchanger, mixing tank, controlling hydrogen soakage with being reduced thing mol ratio is 1 ~ 15:1 hybrid reaction, and material in the reactor mean residence time is 10 ~ 120min.
Reacted material passes into described concentrating unit from reactor bottom outlet through recycle pump, and the concentrated solution containing catalyzer enters reaction cycle, and concentrating unit purified liquor outlet is described aminate.
Described injector is venturi-type eductors, and injector hydrogen soakage is fixed or by distance adjustment between nozzle and reception chamber, makes hydrogen be 1 ~ 15:1 with the mol ratio being reduced thing.
Describedly be reduced thing to add inbound traffics be spray total flux 0.001% ~ 90%, and to export aminate molar flow identical with concentrating unit.
Described catalyzer is with SiO
2, Al
2o
3, silica gel, diatomite or gac be carrier, wherein at least containing one or more in copper, chromium, zinc, iron, nickel, palladium and platinum and oxide compound thereof.
Described control reactor internal recycle mass flow of catalyst is be reduced amount flow 0.001% ~ 10%.
Described concentrating unit can be centrifugal concentrating, filtering and concentrating or flash concentration.
In described reaction unit during catalyst deactivation, in reactor bottom exit portion or all discharge, add from catalyst inlet simultaneously.
Airwater mist cooling mixing is rapidly and efficiently most important for liquid phase catalytic hydrogenation reduction reaction.The present invention uses injection reactor to carry out liquid phase catalytic hydrogenation, the liquid phase jet wherein formed by venturi-type eductors nozzle has strong Involving velocity to gas, make each phase close contact, and produce violent stirring, effectively can improve the mixing efficiency between airwater mist cooling.Injection reactor makes reactant fully mix, and is conducive to reinforcing mass transfer and heat transfer, accelerates speed of reaction, improves concentration and temperature distribution, suppresses side reaction, improves the selectivity of reaction, thus reduces production cost and improve throughput.Meanwhile, the injection reaction unit structure that the present invention adopts is simple, and cost of investment is low, and technique is simple, stable.
Accompanying drawing explanation
Fig. 1 sprays reaction unit structural representation in the embodiment of the present invention.
In figure, 1-reactor; 2-injector; 3-recycle pump; 4-concentrating unit; 5-interchanger; 6-mixing tank; 7-products pot; 8-feedstock pump; 9-head tank; 10-catalyst inlet; 11-gas inlet; 12-aminate exports; 13-reactor bottom outlet.
Embodiment
Below in conjunction with drawings and Examples, the inventive method is illustrated further.
In embodiment, the injection reaction unit of liquid-phase hydrogenatin reduction amination, as shown in Figure 1, comprising:
A () a set of injection reaction unit for liquid-phase hydrogenatin reduction amination, mainly comprises reactor 1 and connects recycle pump 3, concentrating unit 4, interchanger 5 and mixing tank 6 successively with pipeline.
B () is arranged on the injector 2 that reactor head is designed by venturi principle, be made up of nozzle and reception chamber two portions, wherein nozzle is connected with screw thread or flange with reactor 1 top, and reception chamber is fixed on reactor 1 inwall, and the distance between nozzle and reception chamber is fixed or adjustable.
(c) heat-exchanger rig be arranged in reactor 1.
D catalyst inlet 10, that () is arranged on reactor 1 top is arranged on gas inlet 11 and the material outlet 13 be arranged on bottom reactor 1 at reactor 1 top.
E () is for collecting the products pot 7 of concentrating unit 4 purified liquor outlet 12 aminate.
F () is arranged on the raw materials mouth between concentrating unit 4 and interchanger 5, will be reduced thing pump into by feedstock pump 8 from head tank 9.
Liquid-phase hydrogenatin reduction amination processing method described in the embodiment of the present invention is specific as follows:
With the air in nitrogen replacement whole process, then with the nitrogen in hydrogen exchange whole process, the target amination reaction mixture adding catalyzer is added in reactor by reactor 1 top catalyst entrance 10, starting recycle pump makes all pipelines all be full of solution, makes solution in reactor 1 account for 1/3 ~ 1/2 of reactor 1 volume; And to control reactor pressure be 0.5 ~ 3.0Mpa; In reactor 1, pass into heat transferring medium in heat-exchanger rig and interchanger 5, make temperature in reactor 1 be 20 ~ 300 DEG C.
Be reduced the preparation of thing feed rate according to setting and initially add reaction unit internal object aminate solution, make catalyzer be reduced amount 0.001% ~ 10%.Controlling injector hydrogen soakage with the mol ratio being reduced thing is 1 ~ 15:1.
Control is reduced thing feed rate, and making to be reduced thing residence time in reactor 1 is 10 ~ 120min.Be reduced thing to be added by feedstock pump 8, through interchanger 5 preheating, and under mixing tank effect, solid-liquid mixed.
Spray reacted aminate to be discharged by reactor bottom, pass in concentrating unit through recycle pump, cutting out partial aminate, containing catalyzer concentrated solution be reduced thing and be mixed into circulating reaction next time.
When after catalyst member inactivation, 13 can be exported by reactor bottom and partly or entirely get rid of, suitably add at reactor head catalyst inlet 10 simultaneously.
embodiment:
As shown in Figure 1 for reacting in the injection reaction unit of liquid-phase hydrogenatin reduction amination, concrete implement parameter and result as shown in the table.
Claims (7)
1. the method utilizing injection reactor to carry out reduction amination, relate to nitro-compound, nitroso compound, azo-compound, azoxy compound or hydrogenated azo compound and carry out reducing continuously the method obtaining corresponding aminated compounds in injection reaction unit, it is characterized in that comprising the following steps:
(1) prepare to spray reaction unit, described injection reaction unit comprises reactor, injector, recycle pump, concentrating unit, interchanger and mixing tank, and described injector is made up of nozzle, reception chamber, and nozzle is connected with screw thread or flange with reactor head; The reactor head of described injection reaction unit arranges gas feed and catalyst inlet, in reactor, heat-exchanger rig is set, bottom is provided with material outlet, connects recycle pump, concentrating unit, interchanger and mixing tank successively, and arrange material inlet between interchanger and concentrating unit;
(2) the target amination reaction mixture adding catalyzer is added in reactor by reactor head material inlet, ON cycle pump makes material at injection reaction unit internal recycle, hydrogen enters in reactor by gas inlet, and control reactor pressure is 0.5 ~ 3.0MPa;
(3) controlling reactor temperature by heat-exchanger rig is 20 ~ 300 DEG C, added being reduced thing by the material inlet between interchanger and concentrating unit, injector is entered after interchanger, mixing tank, controlling hydrogen soakage with being reduced thing mol ratio is 1 ~ 15:1 hybrid reaction, and material in the reactor mean residence time is 10 ~ 120min;
(4) reacting rear material passes into described concentrating unit from reactor bottom outlet through recycle pump, and the concentrated solution containing catalyzer enters reaction cycle, and concentrating unit purified liquor outlet is described aminate.
2. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that described injector is venturi-type eductors.
3. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that being reduced thing, to add inbound traffics be spray total flux 0.001% ~ 90%, and to export aminate molar flow identical with concentrating unit.
4. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that described catalyzer is with SiO
2, Al
2o
3, silica gel, diatomite or gac be carrier, wherein at least containing one or more in copper, chromium, zinc, iron, nickel, palladium and platinum and oxide compound thereof.
5. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that controlling reactor internal recycle mass flow of catalyst is be reduced amount flow 0.001% ~ 10%.
6. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that concentrating unit is centrifugal concentrating, filtering and concentrating or flash concentration.
7. utilize injection reactor to carry out the method for reduction amination according to claim 1, it is characterized in that when catalyst deactivation, in reactor bottom exit portion or all discharge, add from catalyst inlet simultaneously.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410246202.4A CN105237409A (en) | 2014-06-05 | 2014-06-05 | Method used for reductive amination using jet reactor |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410246202.4A CN105237409A (en) | 2014-06-05 | 2014-06-05 | Method used for reductive amination using jet reactor |
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| CN105237409A true CN105237409A (en) | 2016-01-13 |
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ID=55035284
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| CN201410246202.4A Pending CN105237409A (en) | 2014-06-05 | 2014-06-05 | Method used for reductive amination using jet reactor |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369421A (en) * | 2018-10-31 | 2019-02-22 | 中农发河南农化有限公司 | A kind of novel production process carrying out amidogen ether synthesis using high-pressure injector |
| CN109810024A (en) * | 2019-03-28 | 2019-05-28 | 南京工业大学 | Injection loop reactor for preparing pentamethylene diisocyanate and use method thereof |
| CN109942065A (en) * | 2017-12-21 | 2019-06-28 | 上海电气集团股份有限公司 | A kind of reduction fluidized bed and application thereof and application method |
| CN111233703A (en) * | 2020-02-24 | 2020-06-05 | 山东金石新材料有限公司 | Primary diamine production equipment and method for producing primary diamine by adopting same |
| CN112723989A (en) * | 2019-10-14 | 2021-04-30 | 中国石油化工股份有限公司 | Olefin hydration reaction method and system |
| CN113856565A (en) * | 2021-10-14 | 2021-12-31 | 沈阳化工研究院有限公司 | Device and method for preparing p-trifluoromethoxyaniline through continuous catalytic hydrogenation |
| CN114618396A (en) * | 2022-03-21 | 2022-06-14 | 南京诚志清洁能源有限公司 | Propylene carbonylation reaction device and method |
| CN115594616A (en) * | 2022-10-09 | 2023-01-13 | 浙江迪邦化工有限公司（Cn） | Multistage continuous sulfonation method of 1-aminoanthraquinone |
| CN115636752A (en) * | 2022-09-29 | 2023-01-24 | 宁夏瑞泰科技股份有限公司 | Method for preparing o-phenylenediamine by using jet loop reactor |
| CN116041621A (en) * | 2021-10-28 | 2023-05-02 | 中国石油化工股份有限公司 | Hydrogenated nitrile rubber and preparation method thereof |
| CN117466810A (en) * | 2023-12-26 | 2024-01-30 | 北京弗莱明科技有限公司 | Industrial continuous production method of picloram |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109942065A (en) * | 2017-12-21 | 2019-06-28 | 上海电气集团股份有限公司 | A kind of reduction fluidized bed and application thereof and application method |
| CN109942065B (en) * | 2017-12-21 | 2024-04-12 | 上海电气集团股份有限公司 | Reduction fluidized bed and application and use method thereof |
| CN109369421A (en) * | 2018-10-31 | 2019-02-22 | 中农发河南农化有限公司 | A kind of novel production process carrying out amidogen ether synthesis using high-pressure injector |
| CN109810024A (en) * | 2019-03-28 | 2019-05-28 | 南京工业大学 | Injection loop reactor for preparing pentamethylene diisocyanate and use method thereof |
| CN112723989A (en) * | 2019-10-14 | 2021-04-30 | 中国石油化工股份有限公司 | Olefin hydration reaction method and system |
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