CN106496046A - The method that solvent-free catalytic hydrogenation produces aminoanisole - Google Patents
The method that solvent-free catalytic hydrogenation produces aminoanisole Download PDFInfo
- Publication number
- CN106496046A CN106496046A CN201610864083.8A CN201610864083A CN106496046A CN 106496046 A CN106496046 A CN 106496046A CN 201610864083 A CN201610864083 A CN 201610864083A CN 106496046 A CN106496046 A CN 106496046A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- hydrogenation reaction
- nitroanisole
- solvent
- catalytic hydrogenation
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method that solvent-free catalytic hydrogenation produces aminoanisole, its step is:Input Nitroanisole and catalyst in hydrogenation reaction kettle;Hydrogenation reaction kettle adopts nitrogen displacement to oxygen content≤0.1%, then with hydrogen exchange to hydrogen content >=99.0%, starts stirring, it is warming up to 70 ± 10 DEG C, hydrogen is passed through, in 0.6~1.0Mpa, reaction temperature carries out catalytic hydrogenation reaction at 80~100 DEG C to control reaction pressure;Reaction terminates, and the reducing solution after filtration sends to reduction liquid/gas separator AUTOMATIC ZONING after cooling;Material after layering is sent to dehydration device and carries out normal pressure or negative pressure dehydration, and waste water sends to wastewater treatment equipment;Moisture≤0.1% in material after dehydration, then pass through the isolated described target product of vacuum distillation.The present invention does not use solvent, is not required to solvent recovery unit, fundamentally solves the problems, such as pollution and solvent recovery of the methanol solvate to environment, saved equipment investment, reduced production cost, improve equipment capacity.
Description
Technical field
The invention belongs to technical field of fine, is related to a kind of Nitroanisole catalytic hydrogenation production aminoanisole
Method, particularly a kind of method that aminoanisole is produced using solvent-free catalytic hydrogenation.
Background technology
Aminoanisole is important dyestuff, spice and medicine intermediate.Current domestic production o-aminoanisole and right
Aminoanisole is mainly with ortho-nitroanisole and paranitroanisole as raw material, urges through sodium sulfide, NaHS or solvent
Change hydrogenating reduction three productions method.Using sodium sulfide or reduction with sodium bisulfide, wastewater flow rate is more;Using solvent catalysis hydrogenation also
Former technique need to add methanol as solvent, and the method has the drawback that the use of solvent brings solvent environmental pollution and solvent
Recovery problem, increased solvent recovery cost.
Content of the invention
The purpose of the present invention is the shortcoming existed for existing process technology, there is provided a kind of safer, environmental protection, produces into
The method that this low solvent-free catalytic hydrogenation produces aminoanisole, to solve the skill that existing aminoanisole method of reducing is present
Art problem.
The present invention technical solution be:A kind of method that solvent-free catalytic hydrogenation produces aminoanisole, including such as
Lower step:
Input Nitroanisole and catalyst in hydrogenation reaction kettle;
Hydrogenation reaction kettle adopts nitrogen displacement to oxygen content≤0.1%, then with hydrogen exchange to hydrogen content >=99.0%, starts
Stirring, is warming up to 70 ± 10 DEG C, is passed through hydrogen, and control reaction pressure in 0.6~1.0Mpa, enter at 80~100 DEG C by reaction temperature
Capable accomplished continuously or intermittently catalytic hydrogenation reaction;
Catalytic hydrogenation reaction terminates, and reducing solution is sent to catalyst filter, carries out catalyst recovery, and the catalyst after recovery is returned
The recycled in hydrogenation reaction kettle, the reducing solution after filtration send to reduction liquid/gas separator AUTOMATIC ZONING after cooling;
Material after layering is sent to dehydration device and carries out normal pressure or negative pressure dehydration, and waste water sends to wastewater treatment equipment;
Moisture≤0.1% in material after dehydration, then by the isolated described target product neighbour's amino of vacuum distillation
Methyl phenyl ethers anisole or paraphenetidine product.
Described Nitroanisole can be ortho-nitroanisole or paranitroanisole, or ortho-nitroanisole
Mixture with paranitroanisole arbitrary proportion.
Described hydrogenation reaction kettle can be one-pot batch reactor, or multi-floating bodies continuous reaction kettle.
Described catalyst is palladium/carbon catalyst, and wherein the weight/mass percentage composition of palladium is 1%~5%, preferably 3%.
Described catalyst amount for raw material Nitroanisole quality 0.02%~5%, preferably 0.05%~0.5%.
Described catalyst filter is using sintering metal film or purpose ceramic-film filter.
The present invention chemical equation be:
Compared with prior art, the present invention has advantages below:1st, ortho-nitroanisole, paranitroanisole or the two arbitrarily compare
The mixture of example is o-aminoanisole, paraphenetidine or the two is mixed by hydrogen reducing under palladium/carbon catalyst effect
Compound, reaction pressure, equipment manufacturing cost are little;2nd, the present invention does not use solvent, is not required to solvent recovery unit, fundamentally solves methanol
The problem of pollution and solvent recovery of the solvent to environment, has saved equipment investment, has reduced production cost, improves equipment product
Energy;3rd, due to reclaiming catalyst using sintering metal film or purpose ceramic-film filter, it is achieved that catalyst recycled, catalyst disappear
Consumption reduces;4th, the reducing solution after filtering catalyst after cooling reduction liquid/gas separator in AUTOMATIC ZONING, reduce workman work
Intensity, improves working environment.In a word, present invention eliminates solvent consumption traditionally, it is therefore prevented that ring caused by solvent volatilization
Border pollution problem, has saved equipment investment, improves equipment capacity, reduces production cost, produces safer, environmental protection, work
Skill is more simple, is conducive to industrial application.
Description of the drawings
Process chart of the accompanying drawing 1 for the present invention.
Specific embodiment
Below by specific embodiment, the invention will be further described.
Realize that major process unit of the invention is:Catalytic hydrogenation reaction kettle, catalyst filter, dehydration device, negative pressure
Separated device etc..
Embodiment 1:
Such as Fig. 1, the method and step of solvent-free catalytic hydrogenation production aminoanisole are as follows:
The ortho-nitroanisole and palladium/carbon catalyst for measuring is put in 1 10m hydrogenation reaction kettle, and catalyst amount is neighbour
The 0.20% of Nitroanisole, is filled with nitrogen displacement 3~4 times, takes gas sample analysis oxygen content≤0.1%, then with hydrogen exchange, takes
Hydrogen content >=99.0% analyzed by gas sample, starts stirring, is warming up to 70 DEG C, is passed through hydrogen, control reaction pressure 0.6~
1.0Mpa, reaction temperature carry out catalytic hydrogenation reaction at 80~100 DEG C.
Catalytic hydrogenation reaction terminates, and by reducing solution by being pumped into catalyst filter, carries out catalyst recovery, after filtration
Catalyst by small part reducing solution carry return to recycled in hydrogenation reaction kettle, the most of reducing solution after filtering catalyst
Go to reduce liquid/gas separator.
Reducing solution after filtering catalyst AUTOMATIC ZONING in reduction liquid/gas separator after cooling, the material after layering goes to take off
Water installations, waste water send to wastewater treatment equipment.
Material after layering carries out normal pressure or negative pressure dehydration by dehydration device, and moisture in the reducing solution after dehydration≤
0.1%.
Reducing solution after dehydration reaches more than 99.3% by the isolated o-aminoanisole of vacuum distillation, product content.
Embodiment 2:
Such as Fig. 1, the method and step of solvent-free catalytic hydrogenation production aminoanisole are as follows:
The paranitroanisole and palladium/carbon catalyst for measuring, catalyst is put in the 10m hydrogenation reaction kettles of two series connection
Consumption for paranitroanisole 0.25%, is filled with nitrogen displacement 3~4 times, takes gas sample analysis oxygen content≤0.1%, then uses hydrogen
Gas is replaced, and is taken gas sample analysis hydrogen content >=99.0%, is started stirring, be warming up to 70 DEG C, be passed through hydrogen, control reaction pressure
In 0.6~1.0Mpa, reaction temperature carries out intermittently or serially catalytic hydrogenation reaction at 80~100 DEG C.
Catalytic hydrogenation reaction terminates, and by reducing solution by being pumped into catalyst filter, carries out catalyst recovery, after filtration
Catalyst by small part reducing solution carry return to recycled in hydrogenation reaction kettle, the most of reducing solution after filtering catalyst
Go to reduce liquid/gas separator.
Reducing solution after filtering catalyst AUTOMATIC ZONING in reduction liquid/gas separator after cooling, the material after layering goes to take off
Water installations, waste water send to wastewater treatment equipment.
Material after layering carries out normal pressure or negative pressure dehydration by dehydration device, and moisture in the reducing solution after dehydration≤
0.1%.
Reducing solution after dehydration reaches 99.2% by the isolated paraphenetidine product of vacuum distillation, product content
More than.
Embodiment 3:
Such as Fig. 1, the method and step of solvent-free catalytic hydrogenation production aminoanisole are as follows:
Ortho-nitroanisole, the mixture of paranitroanisole for measuring is put in the 10m hydrogenation reaction kettles of two series connection
And palladium/carbon catalyst, catalyst amount be ortho-nitroanisole, the 0.30% of the amount of the mixture of paranitroanisole, be filled with nitrogen
Gas is replaced 3~4 times, takes gas sample analysis oxygen content≤0.1%, then with hydrogen exchange, take gas sample analyze hydrogen content >=
99.0%, start stirring, be warming up to 70 DEG C, be passed through hydrogen, control reaction pressure in 0.6~1.0Mpa, reaction temperature 80~
100 DEG C carry out intermittently or serially catalytic hydrogenation reaction.
Catalytic hydrogenation reaction terminates, and by reducing solution by being pumped into catalyst filter, carries out catalyst recovery, after filtration
Catalyst by small part reducing solution carry return to recycled in hydrogenation reaction kettle, the most of reducing solution after filtering catalyst
Go to reduce liquid/gas separator.
Reducing solution after filtering catalyst AUTOMATIC ZONING in reduction liquid/gas separator after cooling, the material after layering goes to take off
Water installations, waste water send to wastewater treatment equipment.
Material after layering carries out normal pressure or negative pressure dehydration by dehydration device, and moisture in the reducing solution after dehydration≤
0.1%.
Reducing solution after dehydration is by the isolated o-aminoanisole of vacuum distillation or paraphenetidine product, product
Content reaches more than 99.3%.
Above-described embodiment is only the preference of the present invention, is not intended to limit the present invention, all within the principle of the present invention
Any modifications and variations that is made, within protection scope of the present invention.
Claims (8)
1. a kind of method that solvent-free catalytic hydrogenation produces aminoanisole, it is characterised in that comprise the steps:
Input Nitroanisole and catalyst in hydrogenation reaction kettle;
Hydrogenation reaction kettle is opened to hydrogen content >=99.0% to oxygen content≤0.1%, then with hydrogen exchange using nitrogen displacement
Dynamic stirring, is warming up to 70 ± 10 DEG C, is passed through hydrogen, and, in 0.6~1.0Mpa, reaction temperature is at 80~100 DEG C for control reaction pressure
Carry out accomplished continuously or intermittently catalytic hydrogenation reaction;
Catalytic hydrogenation reaction terminates, and reducing solution is sent to catalyst filter, carries out catalyst recovery, and the catalyst after recovery is returned
The recycled in hydrogenation reaction kettle, the reducing solution after filtration send to reduction liquid/gas separator AUTOMATIC ZONING after cooling;
Material after layering is sent to dehydration device and carries out normal pressure or negative pressure dehydration, and waste water sends to wastewater treatment equipment;
Moisture≤0.1% in material after dehydration, then pass through the isolated described target product of vacuum distillation.
2. the method for claim 1, it is characterised in that described Nitroanisole is ortho-nitroanisole or to nitro
Methyl phenyl ethers anisole, or the mixture of ortho-nitroanisole and paranitroanisole arbitrary proportion.
3. the method for claim 1, it is characterised in that described hydrogenation reaction kettle is one-pot batch reactor, or
It is multi-floating bodies continuous reaction kettle.
4. the method for claim 1, it is characterised in that described catalyst is palladium/carbon catalyst, the wherein quality of palladium
Percentage composition is 1%~5%.
5. the method for claim 1, it is characterised in that described catalyst is palladium/carbon catalyst, the wherein quality of palladium
Percentage composition is 3%.
6. the method for claim 1, it is characterised in that described catalyst amount is raw material Nitroanisole quality
0.02%~5%.
7. the method for claim 1, it is characterised in that described catalyst amount is raw material Nitroanisole quality
0.05%~0.5%.
8. the method for claim 1, it is characterised in that described catalyst filter is using sintering metal film or pottery
Film filter.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610864083.8A CN106496046A (en) | 2016-09-28 | 2016-09-28 | The method that solvent-free catalytic hydrogenation produces aminoanisole |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610864083.8A CN106496046A (en) | 2016-09-28 | 2016-09-28 | The method that solvent-free catalytic hydrogenation produces aminoanisole |
Publications (1)
Publication Number | Publication Date |
---|---|
CN106496046A true CN106496046A (en) | 2017-03-15 |
Family
ID=58291172
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610864083.8A Pending CN106496046A (en) | 2016-09-28 | 2016-09-28 | The method that solvent-free catalytic hydrogenation produces aminoanisole |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106496046A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108047079A (en) * | 2017-12-29 | 2018-05-18 | 烟台安诺其精细化工有限公司 | The preparation method of 2- amino -4- acetyl-anisidines |
CN108047067A (en) * | 2017-12-29 | 2018-05-18 | 烟台安诺其精细化工有限公司 | The preparation method of m-Anisidine |
CN108129335A (en) * | 2017-12-29 | 2018-06-08 | 烟台安诺其精细化工有限公司 | The preparation method of 2,5- dimethoxyanilines |
CN108129336A (en) * | 2017-12-29 | 2018-06-08 | 烟台安诺其精细化工有限公司 | The preparation method of paraphenetidine |
CN108164425A (en) * | 2017-12-29 | 2018-06-15 | 烟台安诺其精细化工有限公司 | The preparation method of m-phenylene diamine (MPD) |
CN108191677A (en) * | 2017-12-29 | 2018-06-22 | 烟台安诺其精细化工有限公司 | The preparation method of o-aminoanisole |
CN108218727A (en) * | 2017-12-29 | 2018-06-29 | 烟台安诺其精细化工有限公司 | The preparation method of o-aminophenol |
CN108218728A (en) * | 2017-12-29 | 2018-06-29 | 烟台安诺其精细化工有限公司 | The preparation method of 2,4- diamino anisoles |
CN110590585A (en) * | 2019-09-25 | 2019-12-20 | 浙江优创材料科技股份有限公司 | Process for preparing benzocaine by solvent-free hydrogenation |
CN110694636A (en) * | 2019-10-08 | 2020-01-17 | 中南大学 | Carbon-based-multi-metal composite nano catalytic material and preparation method and application thereof |
CN111559966A (en) * | 2020-06-16 | 2020-08-21 | 浙江闰土股份有限公司 | Preparation method of p-anisidine and equipment for preparing p-anisidine |
CN115232012A (en) * | 2022-08-02 | 2022-10-25 | 福建康峰新材料有限公司 | Method for producing m-amino benzotrifluoride by solvent-free hydrogenation process |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1861562A (en) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | Process of producing nitrobenzether aminobenzether amidobenzether from chlorobenzene |
CN1861570A (en) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | Tech. of preparing amino benz methyl-phenoxide by nitro methyl-phenoxide mixture catalyzing hydrogenation |
CN101307000A (en) * | 2008-07-11 | 2008-11-19 | 常州市佳森化工有限公司 | Process for preparing aminoanisol and aniline by using mixture of nitroanisole and nitro chlorobenzene as raw materials |
CN101607919A (en) * | 2009-06-22 | 2009-12-23 | 扬州铭睿达化工科技有限公司 | A kind of nitro-chlorobenzene that mixes reacts the method for producing anisidine in water solvent |
CN101798272A (en) * | 2010-03-13 | 2010-08-11 | 长春工业大学 | Method for synthesizing para aminophenylmethylether by catalytic hydrogenation of paranitroanisole |
CN101823972A (en) * | 2010-05-05 | 2010-09-08 | 江苏利田科技有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
CN102276483A (en) * | 2011-06-30 | 2011-12-14 | 辽宁世星药化有限公司 | Production method of oamino pheylmethyl ether |
CN102320985A (en) * | 2011-07-22 | 2012-01-18 | 嘉兴市中华化工有限责任公司 | Method for producing o-aminoanisole by high-efficient reduction reaction |
CN102391134A (en) * | 2011-09-22 | 2012-03-28 | 江苏康恒化工有限公司 | Method for preparing o-anisidine by catalytic hydrogenation |
CN103073436A (en) * | 2011-10-26 | 2013-05-01 | 常州市佳森化工有限公司 | Method of preparing o-anisidine and p-anisidine through hydrogenation reduction of mixture of o-nitroanisole and p-nitroanisole |
CN203220795U (en) * | 2013-05-20 | 2013-10-02 | 张家港市振方化工有限公司 | Stirring suction filtration device |
CN103709051A (en) * | 2013-12-23 | 2014-04-09 | 于宝江 | Preparation method of o-aminoanisole |
CN105249086A (en) * | 2015-11-13 | 2016-01-20 | 侯彦国 | Preparation process of red date condensed juice high in cAMP content |
CN105272863A (en) * | 2014-06-11 | 2016-01-27 | 宁夏明盛染化有限公司 | Preparation method for p-anisidine |
CN105294456A (en) * | 2014-06-11 | 2016-02-03 | 宁夏明盛染化有限公司 | Method for preparing p-anisidine through catalytic hydrogenation by industrial-scale device |
CN105348038A (en) * | 2015-11-06 | 2016-02-24 | 烟台九目化学制品有限公司 | Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds |
CN105523881A (en) * | 2016-01-15 | 2016-04-27 | 中节能万润股份有限公司 | Method for preparing 1,6-dialkyl pyrene |
-
2016
- 2016-09-28 CN CN201610864083.8A patent/CN106496046A/en active Pending
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1861562A (en) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | Process of producing nitrobenzether aminobenzether amidobenzether from chlorobenzene |
CN1861570A (en) * | 2006-06-19 | 2006-11-15 | 常州市佳森化工有限公司 | Tech. of preparing amino benz methyl-phenoxide by nitro methyl-phenoxide mixture catalyzing hydrogenation |
CN101307000A (en) * | 2008-07-11 | 2008-11-19 | 常州市佳森化工有限公司 | Process for preparing aminoanisol and aniline by using mixture of nitroanisole and nitro chlorobenzene as raw materials |
CN101607919A (en) * | 2009-06-22 | 2009-12-23 | 扬州铭睿达化工科技有限公司 | A kind of nitro-chlorobenzene that mixes reacts the method for producing anisidine in water solvent |
CN101798272A (en) * | 2010-03-13 | 2010-08-11 | 长春工业大学 | Method for synthesizing para aminophenylmethylether by catalytic hydrogenation of paranitroanisole |
CN101823972A (en) * | 2010-05-05 | 2010-09-08 | 江苏利田科技有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
CN102276483A (en) * | 2011-06-30 | 2011-12-14 | 辽宁世星药化有限公司 | Production method of oamino pheylmethyl ether |
CN102320985A (en) * | 2011-07-22 | 2012-01-18 | 嘉兴市中华化工有限责任公司 | Method for producing o-aminoanisole by high-efficient reduction reaction |
CN102391134A (en) * | 2011-09-22 | 2012-03-28 | 江苏康恒化工有限公司 | Method for preparing o-anisidine by catalytic hydrogenation |
CN103073436A (en) * | 2011-10-26 | 2013-05-01 | 常州市佳森化工有限公司 | Method of preparing o-anisidine and p-anisidine through hydrogenation reduction of mixture of o-nitroanisole and p-nitroanisole |
CN203220795U (en) * | 2013-05-20 | 2013-10-02 | 张家港市振方化工有限公司 | Stirring suction filtration device |
CN103709051A (en) * | 2013-12-23 | 2014-04-09 | 于宝江 | Preparation method of o-aminoanisole |
CN105272863A (en) * | 2014-06-11 | 2016-01-27 | 宁夏明盛染化有限公司 | Preparation method for p-anisidine |
CN105294456A (en) * | 2014-06-11 | 2016-02-03 | 宁夏明盛染化有限公司 | Method for preparing p-anisidine through catalytic hydrogenation by industrial-scale device |
CN105348038A (en) * | 2015-11-06 | 2016-02-24 | 烟台九目化学制品有限公司 | Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds |
CN105249086A (en) * | 2015-11-13 | 2016-01-20 | 侯彦国 | Preparation process of red date condensed juice high in cAMP content |
CN105523881A (en) * | 2016-01-15 | 2016-04-27 | 中节能万润股份有限公司 | Method for preparing 1,6-dialkyl pyrene |
Non-Patent Citations (3)
Title |
---|
LI, JING: "Pd Nanoparticles in Ionic Liquid Brush: A Highly Active and Reusable Heterogeneous Catalytic Assembly for Solvent-Free or On-Water Hydrogenation of Nitroarene under Mild Conditions", 《ACS CATALYSIS 》 * |
张建华: "液相催化加氮法合成衬氮基苯甲醚", 《中国氯碱》 * |
马宁等: "液相催化加氢还原制备对氨基苯甲醚", 《河南化工》 * |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108218727A (en) * | 2017-12-29 | 2018-06-29 | 烟台安诺其精细化工有限公司 | The preparation method of o-aminophenol |
CN108047079A (en) * | 2017-12-29 | 2018-05-18 | 烟台安诺其精细化工有限公司 | The preparation method of 2- amino -4- acetyl-anisidines |
CN108129335A (en) * | 2017-12-29 | 2018-06-08 | 烟台安诺其精细化工有限公司 | The preparation method of 2,5- dimethoxyanilines |
CN108129336A (en) * | 2017-12-29 | 2018-06-08 | 烟台安诺其精细化工有限公司 | The preparation method of paraphenetidine |
CN108164425A (en) * | 2017-12-29 | 2018-06-15 | 烟台安诺其精细化工有限公司 | The preparation method of m-phenylene diamine (MPD) |
CN108191677A (en) * | 2017-12-29 | 2018-06-22 | 烟台安诺其精细化工有限公司 | The preparation method of o-aminoanisole |
CN108047067A (en) * | 2017-12-29 | 2018-05-18 | 烟台安诺其精细化工有限公司 | The preparation method of m-Anisidine |
CN108218728A (en) * | 2017-12-29 | 2018-06-29 | 烟台安诺其精细化工有限公司 | The preparation method of 2,4- diamino anisoles |
CN110590585A (en) * | 2019-09-25 | 2019-12-20 | 浙江优创材料科技股份有限公司 | Process for preparing benzocaine by solvent-free hydrogenation |
CN110590585B (en) * | 2019-09-25 | 2022-08-23 | 浙江优创材料科技股份有限公司 | Process for preparing benzocaine by solvent-free hydrogenation |
CN110694636A (en) * | 2019-10-08 | 2020-01-17 | 中南大学 | Carbon-based-multi-metal composite nano catalytic material and preparation method and application thereof |
CN110694636B (en) * | 2019-10-08 | 2021-05-07 | 中南大学 | Carbon-based-multi-metal composite nano catalytic material and preparation method and application thereof |
CN111559966A (en) * | 2020-06-16 | 2020-08-21 | 浙江闰土股份有限公司 | Preparation method of p-anisidine and equipment for preparing p-anisidine |
CN115232012A (en) * | 2022-08-02 | 2022-10-25 | 福建康峰新材料有限公司 | Method for producing m-amino benzotrifluoride by solvent-free hydrogenation process |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106496046A (en) | The method that solvent-free catalytic hydrogenation produces aminoanisole | |
CN106316359B (en) | Method for preparing ceramic membrane support body by using water purification sludge and prepared ceramic membrane support body | |
CN100588745C (en) | Method for reclaiming metals by classified electrolysis of electron wastes | |
CN104310520B (en) | A kind of 4B acid producing waste water comprehensive processing method | |
CN107963994A (en) | A kind of green method for preparing 5 FU 5 fluorouracil | |
CN105731748B (en) | A method of bodied ferric sulfate is produced using sewage treatment plant's iron containing sludge | |
CN102675127A (en) | Method and device for preparing 3,4-dichloroaniline without solvent | |
CN106966562A (en) | A kind of method of the liquid bio-oil of utilization treatment with supercritical fluid municipal sludge production high heating value | |
CN101935281A (en) | Method for preparing m-nitrochlorobenzene, o-nitrochlorobenzene and p-nitrochlorobenzene by using nitrochlorobenzene meta-position oil | |
CN203370393U (en) | Chemical dosing device for strengthening dehydration effect of pressurized filter by using aluminium polychlorid filter aid | |
CN105859813B (en) | A kind of technique that steroidal compounds are reclaimed from the leftover bits and pieces of biological fermentation process production androstenedione | |
CN102994138B (en) | Method for preparing biological aviation kerosene by using swell-cooked dirty oil | |
CN105400960A (en) | Method for pressurizing cobalt-rich copper matte to leach out nickel and cobalt and remove iron | |
CN103757246A (en) | Method for producing high-purity gold | |
CN105836822A (en) | Special sewage treatment agent for aluminum product processing and preparation method of special sewage treatment agent for aluminum product processing | |
CN102603514A (en) | Process for preparing sodium gluconate from crop straws | |
CN106277045A (en) | The technique that a kind of titanium dioxide hydrochloric acid residue resource recycles | |
CN203558901U (en) | Supercritical water oxidization treatment device for coking waste water | |
CN203235409U (en) | Device for collecting and treating waste gas in fluorescent powder waste treatment process | |
CN203112629U (en) | Selenium recovery system for colored glaze material waste water | |
CN102923877A (en) | Treatment technology for mirabilite tailing wastewater | |
CN102030452A (en) | Harmless treatment method and device of oil sludge | |
CN104923543A (en) | Cyanogen-containing tailing slag treatment method | |
CN105540923A (en) | Method for removing 2-mercaptopyridine-N-oxide in wastewater and recycling of 2-mercaptopyridine-N-oxide | |
CN111217442A (en) | Novel multistage ozone reaction tower |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170315 |