Nothing Special   »   [go: up one dir, main page]

CN107641084A - A kind of method for producing nitroparaffins co-production ketoxime - Google Patents

A kind of method for producing nitroparaffins co-production ketoxime Download PDF

Info

Publication number
CN107641084A
CN107641084A CN201610587135.1A CN201610587135A CN107641084A CN 107641084 A CN107641084 A CN 107641084A CN 201610587135 A CN201610587135 A CN 201610587135A CN 107641084 A CN107641084 A CN 107641084A
Authority
CN
China
Prior art keywords
formula
reaction
nitroparaffins
ketoxime
ketone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610587135.1A
Other languages
Chinese (zh)
Other versions
CN107641084B (en
Inventor
张英伟
王朋
张新志
王耀红
范远朋
张绍岩
杨克明
张敏生
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beijing Risun Technology Co Ltd
Original Assignee
Beijing Risun Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beijing Risun Technology Co Ltd filed Critical Beijing Risun Technology Co Ltd
Priority to CN201610587135.1A priority Critical patent/CN107641084B/en
Publication of CN107641084A publication Critical patent/CN107641084A/en
Application granted granted Critical
Publication of CN107641084B publication Critical patent/CN107641084B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The application is related to a kind of method for producing nitroparaffins co-production ketoxime, and methods described is included in the presence of the molecular sieve catalyst of ketone ammoxidation, using ketone, ammonia and hydrogen peroxide as reaction raw materials, generates nitroparaffins, co-production ketoxime.The present processes technological reaction mild condition, safety and environmental protection, separation is simple, product purity is high, and the yield of nitroparaffins in adjustable product, to obtain the ratio of required nitroparaffins and ketoxime, thus the application method of coproduction ketoxime while nitroparaffins are produced enhances the production elasticity of nitroparaffins, improves the economic benefit of whole piece technique.

Description

A kind of method for producing nitroparaffins co-production ketoxime
Technical field
The application is related to a kind of method for producing nitroparaffins co-production ketoxime, in particular to one kind using specifically Catalyst, using ketone, ammonia and hydrogen peroxide as raw material, the method for production nitroparaffins co-production ketoxime.
Background technology
Nitroparaffins are a kind of important fine chemical materials, as 2- nitropropanes can be used for producing 2- amino -2- first Base isopropanol etc..The production method of this nitroparaffins is all nitrification process (such as Chinese patent application using alkane at present Disclosed in CN201080047327.4), and Chinese patent application CN201010592408.4 is gone back in reactor etc. Certain improvement is carried out.But operational hazards, seriously polluted low with target product selectivity in these methods, still be present Problem.
Ketoxime, such as acetoxime, as less toxic, efficient reducing agent, not only it is used as boiler water feeding extensively in recent years Oxygen scavenger, the reducing agent for preparing graphene can also be used as (as disclosed in Chinese patent application CN201110122237.3 ).The industrial conventional method for preparing ketoxime is hydroxylamine hydrochloride or HAS method and sodium nitrite method, and they all have dirt The problem of dye is serious, amount of by-products is big and cost is high.In Chinese patent application CN200410018607.9 and CN201310038328.8 also discloses the method using acetone ammoxidation production acetoxime, and it uses the substantial amounts of tert-butyl alcohol or different Propyl alcohol makees solvent.Although there is the generation of 2- nitropropanes in this course of reaction, it is selectively no more than 10%, is acetoxime The accessory substance of production.
However, in the method disclosed in above patent, all without reference to by the way of ketone ammoxidation with high selectivity The method for producing nitroparaffins co-production ketoxime.
Therefore, develop a kind of catalytic reaction using ketone ammoxidation and produce nitroparaffins coproduction ketoxime simultaneously, and green Environmental protection, the method that reaction condition is gentle and feed stock conversion is high, selectivity of product is high are necessary.
The content of the invention
The application is directed to developing a kind of simpler than conventional method, safe and environment-friendly, economical and stably produces nitroparaffin The method of hydrocarbon co-production ketoxime.The molecular sieve catalyst of ketone ammoxidation can be utilized according to the production method of the application, with ketone, ammonia With hydrogen peroxide as raw material, the production co-production ketoxime of nitroparaffins is carried out.
It is described according to the one of the application embodiment there is provided a kind of method for producing nitroparaffins co-production ketoxime Method includes:It is former using the ketone shown in formula 1, ammonia and hydrogen peroxide as reaction in the presence of the molecular sieve catalyst of ketone ammoxidation Material, the nitroparaffins shown in production 2, the ketoxime shown in presentation 3 in parallel
Wherein, R1And R2The aryl of C1-C6 alkyl, C3-C12 cycloalkyl or C6-C12 is represented independently of one another, it is excellent Selection of land, R1And R2The aryl of C1-C4 alkyl, C3-C6 cycloalkyl or C6-C9 is represented independently of one another, it is highly preferred that R1 And R2Methyl, ethyl, cyclopropyl, cyclobutyl, phenyl, aminomethyl phenyl, 3,5-dimethylphenyl or ethylo benzene are represented independently of one another Base.
The chemical reaction that said process is related to is:
[reaction equation 1]
[reaction equation 2]
In reaction equation 1 and formula 2, R1And R2It is as defined above.
Reaction equation 1 represents the preparation process of nitroparaffins, and reaction equation 2 represents that the pair in nitroparaffins preparation process is anti- Should, i.e. the reaction of coproduction ketoxime.Reaction represented by above-mentioned reaction equation 1 and reaction equation 2 occurs simultaneously, by reaction condition, The regulation change of the addition of catalyst, the ratio of material and solvent composition can generate nitroparaffins and ketone containing different proportion The product of oxime.
For example, acetone, butanone, cyclohexanone, acetophenone etc. can be selected from as the ketone shown in the formula 1 of raw material reactant.It is excellent Selection of land, the ketone can be acetone, so as to be 2- nitropropanes as the nitroparaffins shown in the formula 2 of reaction product, make Can be acetoxime for the ketoxime shown in the formula 3 of accessory substance.But the application is not limited to that.
According in the present processes, the molecular sieve catalyst for the ketone ammoxidation of the application can be titanium silicon molecule Sieve catalyst.Preferably, the molecular sieve catalyst can be TS-1, TS-2, Ti-MWW, Ti-ZSM-48, Ti-MOR or Ti- HMS molecular sieve catalysts, it is highly preferred that the molecular sieve catalyst can be TS-1, Ti-MWW or Ti-HMS.
According in the present processes, the dosage of the molecular sieve catalyst can be the formula 1 as raw material reactant The about 0.1%-40% of the quality of shown ketone, it is preferable that can be about 1%-30%.
It can be carried out in a solvent according to the present processes.The solvent can be selected from water, methanol, ethanol, isopropyl The one or more of alcohol or the tert-butyl alcohol etc..The dosage of the solvent is not particularly limited, it is preferred that the solvent is with making Mass ratio for the ketone shown in the formula 1 of raw material reactant is about 1-9:1.
According in the present processes, the ammonia as raw material reactant can be used in the form of ammonia or ammoniacal liquor, excellent Choosing is used in the form of ammoniacal liquor.The mol ratio of wherein ammonia and the ketone shown in formula 1 can be about 1-6:1, preferably from about 1-3:1. Ammonia can disposably be added reaction system or in about 1 hour to about 12 hours, preferably in about 3 hours to about 8 hours It is added in reaction system.
According in the present processes, the hydrogen peroxide as raw material reactant can use 20% to 50% quality dense The aqueous hydrogen peroxide solution of degree.The mol ratio of hydrogen peroxide and the ketone shown in formula 1 can be about 1-3:1, preferably from about 1.25- 2.5:1.Hydrogen peroxide preferably can be added to reaction system in about 2 hours to about 15 hours in about 3 hours to about 8 hours In.
According in the present processes, involved reaction can be in about 35 DEG C to about 100 DEG C, preferably from about 45 DEG C to about 85 Carried out at a temperature of DEG C.Reaction pressure can be about 0.1MPa to about 1.0MPa, preferably from about 0.1MPa to about 0.5MPa.
It can be further comprised isolating and purifying reaction product (i.e. nitroparaffins and formula 3 shown in formula 2 according to the present processes Shown ketoxime) process.Specifically, the reaction solution comprising nitroparaffins and ketoxime obtained after reaction is terminated was carried out Then filter carries out azeotropic distillation to isolate molecular sieve catalyst to filtrate, separate the azeotropic mixture of water outlet and nitroparaffins successively And the azeotropic mixture of water and ketoxime.Thus ketoxime and nitroparaffins can be separated from reaction system, reaches separation reaction product Purpose.
According in the present processes, it is preferable that the ketone is acetone, and the nitroparaffins are 2- nitropropanes, and The ketoxime is acetoxime.
According in the present processes, rectifying column can be used to carry out the azeotropic distillation.Anti- as raw material using acetone In the case of answering thing, the temperature of the tower bottom of rectifying tower can be about 85 DEG C to about 100 DEG C, when the tower top temperature of the rectifying column Distillate the azeotropic mixture of water and 2- nitropropanes when being about 85 DEG C to about 92 DEG C, water and acetoxime are distillated at about 92 DEG C to about 95 DEG C Azeotropic mixture.
For example, when producing 2- nitropropane co-production acetoximes using acetone as raw material, acetone conversion can be about 90% can be about 60% to about 96% to the overall selectivity of about 100%, 2- nitropropanes and acetoxime, 2- nitropropanes in product It can be about 0.1 with the mol ratio of acetoxime:1 to about 10:1.Wherein, acetone conversion is calculated as below:
Acetone molal quantity * before acetone conversion X%=(acetone molal quantity after acetone molal quantity-reaction before reaction)/reaction 100%
The overall selectivity of acetoxime and 2- nitropropane hydrocarbon is calculated as below:
The molal quantity of 2- nitropropanes in 2- nitropropane selectivity S1%=reaction products/(acetone molal quantity before reaction- Acetone molal quantity after reaction) * 100%
The molal quantity of acetoxime in acetoxime selectivity S2%=reaction products/(before reaction third after acetone molal quantity-reaction Ketone molal quantity) * 100%
The selective S2% of the selective S1%+ acetoximes of overall selectivity S%=2- nitropropanes
When using the method for the production nitroparaffins co-production ketoxime according to the application, higher raw material conversion can be obtained Rate and products collection efficiency, and nitroparaffin in product can be adjusted by changing catalyst, raw material proportioning, reaction temperature and solvent etc. The ratio of hydrocarbon.For example, nitro in reaction product can be improved when raising temperature, the addition for increasing catalyst, hydrogen peroxide The ratio of alkane.
According to the application embodiment, for example, when reaction temperature is in 55 DEG C to 65 DEG C of scope, TS-1 catalyst Mass ratio with acetone is 1:5, and the mol ratio of hydrogen peroxide and acetone is 1.3:When 1, in reaction product 2- nitropropanes with The mol ratio (i.e. S1/S2) of acetoxime can be 1:3-1:2;And when changing reaction condition, for example, reaction temperature is improved to 70 DEG C extremely The mass ratio of 80 DEG C of scope, TS-1 catalyst and acetone is 1:3.3, and the mol ratio of hydrogen peroxide and acetone is about 1.8:1 When, the mol ratio of 2- nitropropanes and acetoxime can be 1 in reaction product:1-1.5:1.
[beneficial effect]
Relative to traditional method that production nitroparaffins are nitrified by alkane, according in the production method of the application, work Skill reaction condition is gentle, safety and environmental protection, separation is simple, product purity is high, and can be by changing catalyst, raw material proportioning, reaction Temperature and the proportion of composing of solvent reclaimed water and various alcohol etc. adjust the yield of nitroparaffins in product, with the nitre needed for obtaining The ratio of base alkane and ketoxime, thus the application method of coproduction ketoxime while nitroparaffins are produced enhances nitroparaffins Production elasticity, be advantageous to improve whole piece technique economic benefit.
Embodiment
Hereinafter, the application will be described in detail with reference to according to embodiments herein, but scope of the present application is not It is only limitted to following examples.
Reagent specification source and tester and method:
Ammonia is provided by ammonia steel cylinder, acetone, ammoniacal liquor (20%-30%) and hydrogen peroxide (30%-51%), ethanol, butanol, Tert-butyl alcohol etc. is that analysis is pure, is Beijing Chemical Plant commercially available prod.Product analysis:The concentration of ammonia and hydrogen peroxide uses titrimetry Method;Water is determined using microwater device;Remaining component uses gas chromatograph for determination.SEM, XRD and original are used to the sign of catalyst Sub- absorption apparatus determines surface topography, crystal type and the element composition of catalyst respectively.
Embodiment 1
Using 500mL three neck glass flasks as reactor, 10g Ti-MWW molecular sieve catalytics are sequentially added thereto Agent, the 50g tert-butyl alcohols, 50g water and 38g acetone, and it is put into flask the magnetic stir bar of polytetrafluoroethylene (PTFE) material.Among flask Interface connects condenser pipe backflow, and two side interfaces were pumped into ammoniacal liquor (the 45g/ hours of 135g concentration 25% with peristaltic pump in 3 hours respectively Speed) and 87g concentration 33% aqueous hydrogen peroxide solution (speed of 29g/ hours).Reaction temperature is set as 60 DEG C, magnetic force Stir as 160 revs/min, reaction pressure 0.1MPa.Ammoniacal liquor and aqueous hydrogen peroxide solution kept after feeding reaction condition after Continuous reaction 2 hours.
Reaction result be acetone conversion about 99%, 2- nitropropanes selectivity about 25%, acetoxime selectivity about 71%.
Reacted material is filtered, secondary filter after catalyst is cleaned with 10g water, filtrate merged, into essence Evaporate tower lock out operation.Tower bottom of rectifying tower temperature is set as 100 DEG C, and tower top temperature is in 85 DEG C to 92 DEG C azeotropic distillation water outlets and 2- nitre The azeotropic mixture of base propane, in 92 DEG C to 95 DEG C azeotropic distillation water outlets and the azeotropic mixture of acetoxime.
Embodiment 2
Using 500mL three neck glass flasks as reactor, sequentially add thereto 15g TS-1 molecular sieve catalysts, 100g water and 38g acetone, and it is put into flask the magnetic stir bar of polytetrafluoroethylene (PTFE) material.Flask intermediary interface connects condenser pipe Backflow, two side interfaces were passed through the 26L ammonias (speed of 87 ml/mins under the control of gas mass flow gauge in 5 hours respectively Rate) and it was passed through with peristaltic pump the aqueous hydrogen peroxide solution (speed of 24g/ hours) of 120g concentration 33% in 5 hours.Reaction temperature Degree is set as 68 DEG C, and magnetic agitation is 160 revs/min, reaction pressure 0.1MPa.After ammonia and aqueous hydrogen peroxide solution are fed Reaction condition is kept to continue reaction 2 hours.
Reaction result is acetone conversion about 98%, 2- nitropropanes selectivity about 60.5%, and acetoxime selectivity is about 34%.
Processing to reacted material afterwards is identical with described by embodiment 1.
Embodiment 3
Using 500mL stainless steel cauldron as reactor, 5gTi-HMS molecular sieve catalysts are sequentially added thereto With 5gTS-1 molecular sieve catalysts, 100g isopropanols and 38g acetone, using mechanical agitation oar mixed material.It is disposable to add 89g The ammoniacal liquor of concentration 25%, the aqueous hydrogen peroxide solution (15g/ of 120g concentration 25% was then passed through in 8 hours with high pressure constant-flux pump The speed of hour).Reaction temperature is set as 55 DEG C, and agitating paddle is 160 revs/min, reaction pressure 0.5MPa.Hydrogen peroxide is water-soluble Liquid keeps reaction condition to continue reaction 2 hours after feeding.
Reaction result is acetone conversion about 100%, 2- nitropropanes selectivity about 15.5%, and acetoxime selectivity is about 80.5%.
Processing to reacted material afterwards is identical with described by embodiment 1.
Embodiment 4
Using 500mL three neck glass flasks as reactor, sequentially add thereto 15g TS-1 molecular sieve catalysts, 100g water and 38g acetone, and it is put into flask the magnetic stir bar of polytetrafluoroethylene (PTFE) material.Flask intermediary interface connects condenser pipe Backflow, two side interfaces were passed through the 26L ammonias (speed of 87 ml/mins under the control of gas mass flow gauge in 5 hours respectively Rate) and it was passed through with peristaltic pump the aqueous hydrogen peroxide solution (speed of 30g/ hours) of 150g concentration 33% in 5 hours.Reaction temperature Degree is set as 74 DEG C, and magnetic agitation is 160 revs/min, reaction pressure 0.1MPa.After ammonia and aqueous hydrogen peroxide solution are fed Reaction condition is kept to continue reaction 2 hours.
Reaction result is acetone conversion about 98%, 2- nitropropanes selectivity about 70.5%, and acetoxime selectivity is about 15%.
Processing to reacted material afterwards is identical with described by embodiment 1.

Claims (10)

1. a kind of method for producing nitroparaffins co-production ketoxime, methods described include:In the molecular sieve catalyst of ketone ammoxidation In the presence of, using the ketone shown in formula 1, ammonia and hydrogen peroxide as reaction raw materials, the nitroparaffins shown in production 2, presentation 3 in parallel Shown ketoxime
Wherein, R1And R2The aryl of C1-C6 alkyl, C3-C12 cycloalkyl or C6-C12 is represented independently of one another, preferably Ground, R1And R2The aryl of C1-C4 alkyl, C3-C6 cycloalkyl or C6-C9 is represented independently of one another, it is highly preferred that R1With R2Methyl, ethyl, cyclopropyl, cyclobutyl, phenyl, aminomethyl phenyl, 3,5-dimethylphenyl or ethylphenyl are represented independently of one another.
2. according to the method for claim 1, wherein, the ketone shown in the formula 1 is selected from acetone, butanone, cyclohexanone, benzene second Ketone, it is preferable that the ketone shown in the formula 1 is acetone.
3. according to the method for claim 1, wherein, the molecular sieve catalyst is titanium-silicon molecular sieve catalyst, it is preferable that The molecular sieve catalyst is TS-1, TS-2, Ti-MWW, Ti-ZSM-48, Ti-MOR or Ti-HMS molecular sieve catalyst, more excellent Selection of land, the molecular sieve catalyst are TS-1, Ti-MWW or Ti-HMS.
4. according to the method for claim 1, wherein, the dosage of the molecular sieve catalyst is the ketone shown in the formula 1 The 0.1%-40% of quality, it is preferable that the dosage of the molecular sieve catalyst is the 1%- of the quality of the ketone shown in the formula 1 30%.
5. according to the method for claim 1, wherein, methods described is carried out in a solvent, the solvent is selected from water, first Alcohol, ethanol, the one or more of isopropanol or the tert-butyl alcohol, wherein, the mass ratio of the solvent and the ketone shown in the formula 1 For 1-9:1.
6. according to the method for claim 1, wherein, the ammonia is used in the form of ammonia or ammoniacal liquor, preferably with ammoniacal liquor Form used, wherein, the mol ratio of the ketone shown in the ammonia and the formula 1 is 1-6:1, preferably 1-3:1, wherein, institute State ammonia and disposably added reaction system or in 1 hour to 12 hours, reaction was preferably added in 3 hours to 8 hours In system.
7. according to the method for claim 1, wherein, the hydrogen peroxide uses the peroxidating of 20% to 50% mass concentration Aqueous solution of hydrogen, wherein, the mol ratio of the hydrogen peroxide and the ketone shown in formula 1 is 1-3:1, preferably 1.25-2.5:1, wherein, The hydrogen peroxide was preferably added in reaction system in 2 hours to 15 hours in 3 hours to 8 hours.
8. according to the method for claim 1, wherein, the reaction that methods described is related to is at 35 DEG C to 100 DEG C, and preferably 45 DEG C extremely Carried out at a temperature of 85 DEG C, wherein, the pressure of the reaction is 0.1MPa to 1.0MPa, preferably 0.1MPa to 0.5MPa.
9. according to the method for claim 1, wherein, methods described further comprises:What is obtained after reaction is terminated includes The reaction solution of the ketoxime shown in nitroparaffins and the formula 3 shown in the formula 2 is filtered is urged with isolating the molecular sieve Agent, azeotropic distillation then is carried out to filtrate, separate water outlet and the azeotropic mixture and water of nitroparaffins and the azeotropic of ketoxime successively Thing, it is preferable that methods described carries out the azeotropic distillation using rectifying column.
10. according to the method for claim 9, wherein, the ketone shown in the formula 1 is acetone, the nitroparaffin shown in the formula 2 Hydrocarbon is 2- nitropropanes, and the ketoxime shown in the formula 3 is acetoxime, wherein, the temperature of the tower bottom of rectifying tower is 85 DEG C To 100 DEG C, the azeotropic mixture of water and 2- nitropropanes is distillated when the tower top temperature of the rectifying column is 85 DEG C to 92 DEG C, 92 DEG C extremely The azeotropic mixture of water and acetoxime is distillated at 95 DEG C.
CN201610587135.1A 2016-07-22 2016-07-22 Method for producing nitroalkane and co-producing ketoxime Active CN107641084B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610587135.1A CN107641084B (en) 2016-07-22 2016-07-22 Method for producing nitroalkane and co-producing ketoxime

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610587135.1A CN107641084B (en) 2016-07-22 2016-07-22 Method for producing nitroalkane and co-producing ketoxime

Publications (2)

Publication Number Publication Date
CN107641084A true CN107641084A (en) 2018-01-30
CN107641084B CN107641084B (en) 2020-08-18

Family

ID=61109645

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610587135.1A Active CN107641084B (en) 2016-07-22 2016-07-22 Method for producing nitroalkane and co-producing ketoxime

Country Status (1)

Country Link
CN (1) CN107641084B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110003013A (en) * 2019-03-26 2019-07-12 山东理工大学 Catalytic distillation prepares the green method of nitroparaffins
CN110511126A (en) * 2019-09-25 2019-11-29 山东省化工研究院 The method of by-product nitroparaffins is handled in a kind of ammoxidation oximation reaction of TS-1 catalysis
CN115557840A (en) * 2022-11-04 2023-01-03 浙江新化化工股份有限公司 Preparation method of 2-nitropropane and catalyst used in preparation method
CN115845915A (en) * 2021-09-24 2023-03-28 北京旭阳科技有限公司 Modified titanium-silicon catalyst, preparation method thereof and method for preparing nitroalkane by using same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101757945A (en) * 2009-12-25 2010-06-30 湘潭大学 Titanium-silicon molecular sieve TS-1 catalyst for catalyzing ketone oximation reaction
CN105732393A (en) * 2016-04-05 2016-07-06 宁波欧迅化学新材料技术有限公司 Synthesizing method of 2-nitropropane
CN106045859A (en) * 2016-07-01 2016-10-26 定州旭阳科技有限公司 Method for preparing 2-nitropropane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101757945A (en) * 2009-12-25 2010-06-30 湘潭大学 Titanium-silicon molecular sieve TS-1 catalyst for catalyzing ketone oximation reaction
CN105732393A (en) * 2016-04-05 2016-07-06 宁波欧迅化学新材料技术有限公司 Synthesizing method of 2-nitropropane
CN106045859A (en) * 2016-07-01 2016-10-26 定州旭阳科技有限公司 Method for preparing 2-nitropropane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
卓佐西: "选择性合成肟反应导向的钛硅分子筛催化活性中心及其转化行为的研究", 《工程科技Ⅰ辑》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110003013A (en) * 2019-03-26 2019-07-12 山东理工大学 Catalytic distillation prepares the green method of nitroparaffins
CN110003013B (en) * 2019-03-26 2021-11-05 山东理工大学 Green method for preparing nitroalkane by catalytic distillation
CN110511126A (en) * 2019-09-25 2019-11-29 山东省化工研究院 The method of by-product nitroparaffins is handled in a kind of ammoxidation oximation reaction of TS-1 catalysis
CN110511126B (en) * 2019-09-25 2022-09-23 山东省化工研究院 Method for treating byproduct nitroalkane in ammoxidation oximation reaction catalyzed by TS-1
CN115845915A (en) * 2021-09-24 2023-03-28 北京旭阳科技有限公司 Modified titanium-silicon catalyst, preparation method thereof and method for preparing nitroalkane by using same
CN115557840A (en) * 2022-11-04 2023-01-03 浙江新化化工股份有限公司 Preparation method of 2-nitropropane and catalyst used in preparation method
CN115557840B (en) * 2022-11-04 2023-11-10 浙江新化化工股份有限公司 Preparation method of 2-nitropropane and catalyst used in preparation method

Also Published As

Publication number Publication date
CN107641084B (en) 2020-08-18

Similar Documents

Publication Publication Date Title
CN107641084A (en) A kind of method for producing nitroparaffins co-production ketoxime
WO2018121042A1 (en) Production method for high-quality pure hexanediamine
JP5918253B2 (en) How to make pure methylal
TW200804234A (en) Process for preparing aniline
EP1309530B1 (en) Process for dehydrohalogenation of halogenated compounds
TWI488834B (en) Purification of acetonitrile
CN113816874B (en) Process method for synthesizing 4-cyano-2-fluorobenzyl alcohol
JP2021528472A (en) Process for the preparation of cyclopropane compounds using diazo compounds
CN110003013B (en) Green method for preparing nitroalkane by catalytic distillation
CN113329994B (en) Method for continuously preparing 5-cyanodiol
TWI259174B (en) Process for treating an aqueous medium containing cyclohexanone oxime and cyclohexanone
CN108863874A (en) A kind of method of continuous synthesis dibenzyl aminodithioformic acid sodium
CN109627172A (en) Using the ethamine production system and technique of extraction-rectification processing waste water
JPH02147A (en) Synthesis of n,n-dialkylhydroxylamine
CN103450028B (en) Method for preparing cyclohexylamine and dicyclohexylamine from nitrobenzene through one-step catalytic hydrogenation
CN116283745B (en) Method for preparing 2,3, 6-trichloropyridine and co-producing trichloroacetyl chloride from 3-chloropyridine
CN101234996B (en) Green synthesis method for ketazine
US7390929B2 (en) Method for the continuous synthesis of monoalkyl-hydrazines with a functionalized alkyl group
WO2019008594A1 (en) Continuous process for the preparation of 2-(1h-imidazol-4-yl) ethanamine and pharmaceutically acceptable salts thereof
CN109608303B (en) Preparation method of high-purity alpha-vinylchloride cyclopropane
JP2022505786A (en) Production of hydroxyethylpiperazine
CN117342972A (en) Method for preparing dihydroxypropyl hydroxylamine, reaction system and obtained product
WO2002070474A1 (en) Process for producing lactam
US9102585B2 (en) Efficient continuous process for manufacturing of 4-aminodiphenylamine from aniline and nitrobenzene
CN117466836A (en) Method for synthesizing allyl tertiary amine

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant