CN106977406A - The method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene - Google Patents
The method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene Download PDFInfo
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- CN106977406A CN106977406A CN201710141103.3A CN201710141103A CN106977406A CN 106977406 A CN106977406 A CN 106977406A CN 201710141103 A CN201710141103 A CN 201710141103A CN 106977406 A CN106977406 A CN 106977406A
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- catalytic hydrogenation
- hydriding
- synthesizing amino
- amino naphthalene
- continuous autoclave
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a kind of method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, comprise the following steps:In the first order hydriding reactor that catalyst is added to multipoles reactors, the air in hydriding reactors at different levels is replaced with hydrogen, and continue to be passed through hydrogen into hydriding reactors at different levels, the mixed liquor containing nitronaphthalene and antitoxinization auxiliary agent is continuously added in first order hydriding reactor again, carry out hydrogenation, the completely rear automatic overflow of first order hydriding reactor carries out hydrogenation into second level hydriding reactor, by that analogy;The completely rear automatic overflow of afterbody hydriding reactor is settled to kettle is settled, and bottom catalyst is applied to first order hydriding reactor after reclaiming, and supernatant liquor distills precipitation after filtering, obtains amino naphthalenes.This method adds antitoxinization auxiliary agent, can greatly reduce sulfur-bearing thing and catalyst is poisoned, catalyst can be recycled;Other this method also has the advantages that production cost is low, production efficiency is high, technique is simple and convenient to operate, conversion ratio and high income.
Description
Technical field
The present invention relates to fine chemistry industry preparing technical field, more particularly to a kind of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene
Method.
Background technology
Amino naphthalenes include:Amino naphthalenes, 2- amino naphthalenes, 1,5-diaminonaphthalene, 1,8- diaminonaphthalenes etc., it is most of to be used to make a living
Produce the important intermediate of dyestuff, synthetic material, medicine etc..Wherein amino naphthalenes also known as alpha naphthylamine, α-amino-naphthalene, alpha-naphthylamine or amino
Naphthalene, is white needles, with niff.Water is slightly soluble in, ethanol, ether is soluble in.The product are direct dyes, acid dye
The intermediate of a variety of dye products such as material, azoic dyes and disperse dyes, is the primary raw material of a variety of rubber antioxidants, is also used for
Organic synthesis.Amino naphthalenes industrial production mainly obtains nitronaphthalene using crude naphthalene nitrification and restores obtained amino naphthalenes, main reduction
Method has akali sulphide or iron powder reducing method and catalytic hydrogenating reduction method, sodium sulfide reducing method as described in patent CN101973894A,
Using sulphur and caustic soda producing alpha naphthylamine by reduction, the major defect existed has:Product yield is low, poor appearance, and produces a large amount of
Difficult waste water, waste residue, do not meet the requirement of cleanly production, and high energy consumption does not meet the requirement of energy-saving and emission-reduction, gradually urged
Change hydrogenating reduction method to replace.The characteristics of catalytic hydrogenating reduction method has environment-friendly, can efficiently reduce three waste discharge, improve
The yield of product.Having realized the catalyst of industrial applications mainly has palladium carbon, a Raney's nickel, but is due to that crude naphthalene is brought into and contained on a small quantity
Catalyst and easily poisoned in oxidation of sulfur compound impurities, actual hydrogenation process by sulfur-containing compound, catalyst can not be recycled, and be caused
Catalyst cost remains high.Other catalyst report has ambrose alloy composite catalyst or nitrogen doped carbon nanotube, such as Chinese patent
CN102304053A and CN105753717A, but experimental stage is all rested at present, it there are no industrialization report.In addition, these
Catalytic hydrogenation synthesis alpha naphthylamine generally uses Batch Process mode in the prior art, and inefficiency, catalyst activity is low, yield
It is low, it is necessary to which continuous supplement, applies mechanically the few short life of number of times, operation inconvenience is now in experiment or lab scale stage, industrializing implementation
It is more difficult.
The content of the invention
The technical problem to be solved in the present invention be overcome the deficiencies in the prior art to can be recycled there is provided a kind of catalyst,
Production cost is low, production efficiency is high, technique is simple and convenient to operate, the synthesis of the continuous autoclave catalytic hydrogenation of conversion ratio and high income
The method of amino naphthalenes.
In order to solve the above technical problems, the present invention uses following technical scheme:
A kind of method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, comprises the following steps:
In the first order hydriding reactor that catalyst is added to multipoles reactors, the sky in hydriding reactors at different levels is replaced with hydrogen
Gas, and continuing toward being passed through hydrogen in hydriding reactors at different levels, then be continuously added to contain nitronaphthalene in first order hydriding reactor and antitoxinization is helped
The mixed liquor of agent, carries out hydrogenation, and the completely rear automatic overflow of first order hydriding reactor carries out hydrogenation into second level hydriding reactor,
By that analogy;Afterbody hydriding reactor completely after automatic overflow settled to kettle is settled, be applied to the after the recovery of bottom catalyst
One-level hydriding reactor, supernatant liquor distills precipitation after filtering, obtains amino naphthalenes.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the antitoxinization auxiliary agent include ammoniacal liquor,
Organic base, phosphate or acetate.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the organic base include ethylenediamine or
Triethylamine.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the acetate include sodium acetate or
Potassium acetate etc..
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the phosphate include ammonium phosphate salt,
Sodium ascorbyl phosphate, potassium phosphate etc..
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the catalyst includes palladium carbon or thunder
Buddhist nun's nickel.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the nitronaphthalene containing 1- and antitoxinization
In the mixed liquor of auxiliary agent, the mass ratio of the 1- nitronaphthalenes and antitoxinization auxiliary agent is 1: 0.01~0.04.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the nitronaphthalene containing 1- and antitoxinization
In the mixed liquor of auxiliary agent, in addition to solvent, the mass ratio of the nitronaphthalene, solvent and antitoxinization auxiliary agent for 1: 1~5: 0.01~
0.04。
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that the solvent include alcohols, aromatic hydrocarbons,
Halogenated hydrocarbons or amine solvent.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that in hydriding reactors at different levels, hydrogenation
Reaction temperature is 40~200 DEG C, and hydrogen pressure is 0.1~5.0Mpa.
The method of above-mentioned continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, it is preferred that described nitronaphthalene is:1- nitros
Naphthalene, 2- nitronaphthalenes, 1,5- dinitronaphthalene, 1,8- dinitronaphthalene, corresponding product is respectively:1- amino naphthalenes, 2- amino naphthalenes, 1,5-
Diaminonaphthalene, 1,8- diaminonaphthalenes.
Compared with prior art, the advantage of the invention is that:
1st, the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene of the invention, with the addition of antitoxinization auxiliary agent, antitoxinization is helped
Agent can be ammoniacal liquor, organic base, phosphate or acetate, can greatly reduce sulfur-bearing thing and catalyst is poisoned so that catalysis
Agent can be recycled, and extend the service life of catalyst, and reaction raw materials, catalyst and antitoxinization auxiliary agent are simple and easy to get, drop
Low production cost.
2nd, the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene of the invention, is carried out multistage using multipoles reactors
Continuous autoclave hydrogenation, technique is simple, easy to operate, production efficiency height, reaction conversion ratio and high income, meets industrial metaplasia
Production is required.
3rd, further, the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene of the invention, can add aprotic solvent
As the retarder thinner of raw material 1- nitronaphthalenes, so that reaction is carried out, such as toluene, dichloroethanes, these aprotic solvent can
Recycle, the water for reacting generation is easily separated, is easy to industrialized production, can thoroughly replace amine solvent of the prior art.
Embodiment
Below in conjunction with specific preferred embodiment, the invention will be further described, but not thereby limiting the invention
Protection domain.
Following examples and comparative example carry out continuous autoclave catalytic hydrogenation synthesizing amino naphthalene using multipoles reactors,
The multipoles reactors include the first order hydriding reactor, second level hydriding reactor and sedimentation kettle being sequentially connected in series, first order hydriding reactor
Continuous liquid adding device is additionally provided with being respectively equipped with the hydriding reactor of the second level on continuous aerator, first order hydriding reactor;The first order
The volume of hydriding reactor and second level hydriding reactor is 200L.
Embodiment 1:
2kg aqueous 50% Raney's nickel is added into first order hydriding reactor, closes after hydriding reactors at different levels, passes through continuous aerating
Device is passed through nitrogen into hydriding reactors at different levels three times, to replace the air in hydriding reactors at different levels, then is passed through hydrogen three times, to replace
Nitrogen in hydriding reactors at different levels.Add what is be made up of 1- nitronaphthalenes and toluene into first order hydriding reactor by continuous liquid adding device
Mixed liquor, and mass concentration are 4% biphosphate sodium water solution, and the flow for the mixed liquor that 1- nitronaphthalenes and toluene are constituted is
112kg/h, the flow of 4% biphosphate sodium water solution is 16.8kg/h, and it is 90 DEG C, the hydrogen pressure of hydriding reactors at different levels to control material temperature
For 1.6MPa, first automatic overflow is hydrogenated into second level hydriding reactor after first order hydriding reactor carries out hydrogenation, hydroful
Automatic overflow is settled to kettle is settled after reaction, second level hydriding reactor hydroful, and sedimentation bottom portion catalyst is applied to after reclaiming
First order hydriding reactor, supernatant liquor distills precipitation after filtering, obtains 1- amino naphthalenes, conversion ratio 100%, yield 99.5%.Even
After reforwarding row 1000 hours, conversion ratio 99.8%, yield 99.5%.
Comparative example 1:
This comparative example is substantially the same manner as Example 1, and it only difference is that:It is added without the biphosphate of mass concentration 4%
Sodium water solution, conversion ratio 100%, yield 99.5%.Conversion ratio 65%, yield 55% after continuously running 100 hours.
Embodiment 2:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Replaced using the sodium acetate of mass concentration 4%
The sodium dihydrogen phosphate of mass concentration 4% in embodiment 1.Conversion ratio 100%, yield 99.5%.After continuous operation 1000 hours
Conversion ratio 98%, yield 97.6%.
Embodiment 3:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Replace aqueous using aqueous 50% palladium carbon
The mass fraction of palladium is 3% in 50% Raney's nickel, palladium carbon.Conversion ratio 100%, yield 99.5%.After continuous operation 800 hours
Conversion ratio 98.6%, yield 98%.
Embodiment 4:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:By reaction temperature control in 120 DEG C, conversion ratio
100%, yield 99.5%.Conversion ratio 99.5%, yield 99% after continuously running 1000 hours.
Embodiment 5:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:By reaction temperature control at 80 DEG C, continuous fortune
Row conversion ratio 99%, yield 98.5% after 1000 hours.
Embodiment 6:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:By reaction temperature control at 60 DEG C, continuous fortune
Row conversion ratio 98%, yield 97.6% after 1000 hours.
Embodiment 7:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Hydrogen Vapor Pressure is controlled into 1.0MPa, conversion ratio
100%, yield 99.5%.Conversion ratio 99.6%, yield 99% after continuously running 1000 hours.
Embodiment 8:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Hydrogen Vapor Pressure is controlled into 2.0MPa, conversion ratio
100%, yield 99.5%.Conversion ratio 99.5%, yield 99.1% after continuously running 1000 hours.
Embodiment 9:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Embodiment 1 is replaced using 1,2- dichloroethanes
Toluene be used as retarder thinner, conversion ratio 100%, yield 99.5%.Conversion ratio 99.6%, yield after continuously running 1000 hours
99%.
Embodiment 10:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:The 1,2- bis- of embodiment 1 is replaced using methanol
Chloroethanes is used as retarder thinner, conversion ratio 100%, yield 99.5%.Conversion ratio 99.7%, yield after continuously running 1000 hours
99.4%.
Embodiment 11:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:The 1,2- bis- of embodiment 1 is replaced using ethanol
Chloroethanes is used as retarder thinner, conversion ratio 100%, yield 99.5%.Conversion ratio 99.6%, yield after continuously running 1000 hours
99.3%.
Embodiment 12:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:The 1- of embodiment 1 is replaced using 2- nitronaphthalenes
Nitronaphthalene, conversion ratio 100%, yield 99.5%.Conversion ratio 99.6%, yield 99.3% after continuously running 1000 hours.
Embodiment 13:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Embodiment 1 is replaced using 1,5- dinitronaphthalene
1- nitronaphthalenes, conversion ratio 100%, yield 99.5%.Conversion ratio 99.6%, yield 99.3% after continuously running 1000 hours.
Embodiment 14:
The present embodiment is substantially the same manner as Example 1, and it only difference is that:Embodiment 1 is replaced using 1,8- dinitronaphthalene
1- nitronaphthalenes, conversion ratio 100%, yield 99.5%.Conversion ratio 99.6%, yield 99.3% after continuously running 1000 hours.
Described above is only the preferred embodiment of the present invention, and protection scope of the present invention is not limited merely to above-mentioned implementation
Example.All technical schemes belonged under thinking of the present invention belong to protection scope of the present invention.It is noted that for the art
Those of ordinary skill for, improvements and modifications under the premise without departing from the principles of the invention, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (11)
1. a kind of method of continuous autoclave catalytic hydrogenation synthesizing amino naphthalene, comprises the following steps:
In the first order hydriding reactor that catalyst is added to multipoles reactors, the air in hydriding reactors at different levels is replaced with hydrogen,
And continue toward being passed through hydrogen in hydriding reactors at different levels, then be continuously added in first order hydriding reactor containing nitronaphthalene and antitoxinization auxiliary agent
Mixed liquor, carries out hydrogenation, the completely rear automatic overflow of first order hydriding reactor carries out hydrogenation into second level hydriding reactor, with this
Analogize;The completely rear automatic overflow of afterbody hydriding reactor is settled to kettle is settled, and bottom catalyst is applied to the first order after reclaiming
Hydriding reactor, supernatant liquor distills precipitation after filtering, obtains amino naphthalenes.
2. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 1, it is characterised in that described antitoxin
Changing auxiliary agent includes ammoniacal liquor, organic base, phosphate or acetate.
3. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 2, it is characterised in that described organic
Alkali includes ethylenediamine or triethylamine.
4. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 2, it is characterised in that the acetic acid
Salt includes sodium acetate or potassium acetate etc..
5. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 2, it is characterised in that the phosphoric acid
Salt includes ammonium phosphate salt, sodium ascorbyl phosphate, potassium phosphate etc..
6. the method for the continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to any one of Claims 1 to 5, its feature exists
In the catalyst includes palladium carbon or Raney's nickel.
7. the method for the continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to any one of Claims 1 to 5, its feature exists
In in the mixed liquor of the nitronaphthalene containing 1- and antitoxinization auxiliary agent, the mass ratio of the 1- nitronaphthalenes and antitoxinization auxiliary agent is 1:
0.01~0.04.
8. the method for the continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to any one of Claims 1 to 5, its feature exists
In, in the mixed liquor of the nitronaphthalene containing 1- and antitoxinization auxiliary agent, in addition to solvent, the nitronaphthalene, solvent and antitoxinization are helped
The mass ratio of agent is 1: 1~5: 0.01~0.04.
9. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 8, it is characterised in that the solvent
Including alcohols, aromatic hydrocarbons, halogenated hydrocarbons or amine solvent.
10. the method for the continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to any one of Claims 1 to 5, its feature exists
In in hydriding reactors at different levels, the reaction temperature of hydrogenation is 40~200 DEG C, and hydrogen pressure is 0.1~5.0Mpa.
11. the method for continuous autoclave catalytic hydrogenation synthesizing amino naphthalene according to claim 1, it is characterised in that described
Nitronaphthalene is:1- nitronaphthalenes, 2- nitronaphthalenes, 1,5- dinitronaphthalene, 1,8- dinitronaphthalene, corresponding product is respectively:1- amino
Naphthalene, 2- amino naphthalenes, 1,5-diaminonaphthalene, 1,8- diaminonaphthalenes.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107827790A (en) * | 2017-11-22 | 2018-03-23 | 浙江嘉化新材料有限公司 | A kind of methyl sulphonyl benzene synthetic method of 1 methyl 4 |
CN108689863A (en) * | 2018-06-08 | 2018-10-23 | 浙江工业大学 | A method of preparing 5,6,7,8- tetrahydrochysenes-naphthalidine by raw material of 1,8- dinitronaphthalene |
CN113956301A (en) * | 2021-11-24 | 2022-01-21 | 浙江大学 | Multi-kettle series continuous hydrogenation method and device for sugar alcohol production |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB799871A (en) * | 1955-05-10 | 1958-08-13 | Du Pont | Hydrogenation catalysts and process |
GB1460409A (en) * | 1974-08-10 | 1977-01-06 | Bayer Ag | Process for the manufacture 'f di- and triamino naphthalenes |
CN1123790A (en) * | 1994-08-08 | 1996-06-05 | 拜尔公司 | A process for producing aromatic amines |
CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Production method of o-chloroaniline |
CN101544569A (en) * | 2009-05-18 | 2009-09-30 | 南通海迪化工有限公司 | Method for preparing 1,5-diaminonaphthalene through catalytic hydrogenation |
CN103360267A (en) * | 2013-07-23 | 2013-10-23 | 淮安嘉诚高新化工股份有限公司 | Continuous liquid-phase catalytic hydrogenation reduction method for production of o-chloroaniline |
CN106467467A (en) * | 2016-08-26 | 2017-03-01 | 南通龙翔化工有限公司 | A kind of method that fixed bed continuous catalytic hydrogenation prepares diaminonaphthalene |
-
2017
- 2017-03-10 CN CN201710141103.3A patent/CN106977406A/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB799871A (en) * | 1955-05-10 | 1958-08-13 | Du Pont | Hydrogenation catalysts and process |
GB1460409A (en) * | 1974-08-10 | 1977-01-06 | Bayer Ag | Process for the manufacture 'f di- and triamino naphthalenes |
CN1123790A (en) * | 1994-08-08 | 1996-06-05 | 拜尔公司 | A process for producing aromatic amines |
CN101333169A (en) * | 2007-03-01 | 2008-12-31 | 淮安嘉诚高新化工股份有限公司 | Production method of o-chloroaniline |
CN101544569A (en) * | 2009-05-18 | 2009-09-30 | 南通海迪化工有限公司 | Method for preparing 1,5-diaminonaphthalene through catalytic hydrogenation |
CN103360267A (en) * | 2013-07-23 | 2013-10-23 | 淮安嘉诚高新化工股份有限公司 | Continuous liquid-phase catalytic hydrogenation reduction method for production of o-chloroaniline |
CN106467467A (en) * | 2016-08-26 | 2017-03-01 | 南通龙翔化工有限公司 | A kind of method that fixed bed continuous catalytic hydrogenation prepares diaminonaphthalene |
Non-Patent Citations (1)
Title |
---|
王成武等: "催化加氢还原法制备甲萘胺", 《上海化工》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107827790A (en) * | 2017-11-22 | 2018-03-23 | 浙江嘉化新材料有限公司 | A kind of methyl sulphonyl benzene synthetic method of 1 methyl 4 |
CN108689863A (en) * | 2018-06-08 | 2018-10-23 | 浙江工业大学 | A method of preparing 5,6,7,8- tetrahydrochysenes-naphthalidine by raw material of 1,8- dinitronaphthalene |
CN113956301A (en) * | 2021-11-24 | 2022-01-21 | 浙江大学 | Multi-kettle series continuous hydrogenation method and device for sugar alcohol production |
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Application publication date: 20170725 |