CN101898135B - Amorphous catalyst for catalytic hydrogenation of 2-cyan-4-nitroaniline and preparation method of 2,5-diamincyanophenyl - Google Patents
Amorphous catalyst for catalytic hydrogenation of 2-cyan-4-nitroaniline and preparation method of 2,5-diamincyanophenyl Download PDFInfo
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- CN101898135B CN101898135B CN201010229163A CN201010229163A CN101898135B CN 101898135 B CN101898135 B CN 101898135B CN 201010229163 A CN201010229163 A CN 201010229163A CN 201010229163 A CN201010229163 A CN 201010229163A CN 101898135 B CN101898135 B CN 101898135B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims description 15
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 15
- 229910052796 boron Inorganic materials 0.000 claims abstract description 12
- 230000009467 reduction Effects 0.000 claims description 12
- 230000035484 reaction time Effects 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052723 transition metal Inorganic materials 0.000 abstract description 9
- 150000003624 transition metals Chemical class 0.000 abstract description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052759 nickel Inorganic materials 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
- 229910000808 amorphous metal alloy Inorganic materials 0.000 description 17
- 239000000047 product Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 7
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- YVXLBNXZXSWLIK-UHFFFAOYSA-N 2,5-diaminobenzonitrile Chemical compound NC1=CC=C(N)C(C#N)=C1 YVXLBNXZXSWLIK-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940078494 nickel acetate Drugs 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention relates to an amorphous catalyst for the catalytic hydrogenation of 2-cyan-4-nitroaniline and a method for preparing 2,5-diamincyanophenyl through catalytic hydrogenation by using the catalyst. The amorphous catalyst is prepared from nickel, boron and transition metal M and is characterized by comprising 20-70% of Ni, 30-60% of B and 0-10% of transition metal M in mole percent. The catalytic hydrogenation reaction of catalytic hydrogenation is performed under the action of the catalyst so as to prepare 2,5-diamincyanophenyl. Cyan in 2-cyan-4-nitroaniline can not be reduced by using the catalyst for catalytic hydrogenation, and the hydrogenation reaction of 2-cyan-4-nitroaniline has high conversion rate, good selectivity and safe technology operation.
Description
Technical field
The present invention relates to a kind of amorphous catalyst of 2 cyano 4 nitro aniline catalytic hydrogenation, and through this catalyst to catalyzing hydrogenating preparation 2,5-diaminobenzene nitrile method.
Background technology
2,5-diaminobenzene nitrile is a kind of organic chemical industry's intermediate, is the important source material of synthetic dyestuffs, medicine, macromolecular material, and its modified product as existing macromolecular material has caused extensive attention now.Also do not see 2 in the industry at present, the preparation method's of 5-diaminobenzene nitrile report, and by the 2 cyano 4 nitro aniline Synthetic 2,5-diaminobenzene nitrile main method step is for amino with a nitroreduction on the phenyl ring.
With nitroreduction is the amino technology that in industry, has many maturations.Mainly contain iron powder reducing method, sodium sulfide reducing method, hydrazine hydrate reduction method and catalytic hydrogenating reduction method.The iron powder reducing method is reducing agent with the iron powder, and this method product yield is low, is merely about 75%, and labor strength is big, and has a large amount of three wastes, and environmental pollution is serious, belongs to eliminating technology.Though it is sodium sulfide reducing method cost is low, more than the iron powder reducing method three wastes.The hydrazine hydrate reduction method is solvent with the low-carbon alcohols, and hydrazine hydrate is reducing agent (hydrogen donor), and the product quality that this method is produced is general, and yield is also relatively poor, and the hydrazine hydrate price is high, and fringe cost is high, and toxicity is big, so technology has also obtained restriction.Catalytic hydrogenation process is simple, and employing hydrogen is reducing agent, and the three wastes are less, be the main method of the nitro compound reducing of present advanced country popularization, and impurity is few, and product yield is high.The key of catalytic hydrogenation process is according to different raw materials and preparation of product different catalyst.The catalyst of hydrogenating reduction mainly contains noble metal platinum, palladium etc.; This activity of such catalysts is high; But process conditions are very strict when being applied to the 2 cyano 4 nitro aniline hydrogenating reduction; If process conditions control is bad, can be amino with cyanic acid also while hydrogenating reduction, so selectivity have descended on the contrary.The Raney Raney nickel is that the nitro compound that extensively adopts at present is reduced to amino catalyst.But, operate and careless slightlyly promptly possibly cause serious fire because the Raney Raney nickel very easily catches fire.Simultaneously, Raney Raney nickel activity in the reduction of 2 cyano 4 nitro aniline is not high, and hydrogenation pressure requires than higher, therefore in industry, equipment material is required high.Therefore invent a kind of active high, selectivity is also high, the catalyst that is unlikely to make the cyanic acid in the 2 cyano 4 nitro aniline to be reduced is the technical problem that the technical staff of chemical technology field needs to be resolved hurrily always.Granted publication day be December 30 in 2009 Ri Granted publication number for disclosing a kind of preparation and application of amorphous nickel alloy catalyst in the patent of invention of CN100576339C; It is highly profitable to the use longevity people that improve reaction efficiency, shortening reaction time, prolongation catalyst, and then selectivity is not high but be applied to the 2 cyano 4 nitro aniline catalytic hydrogenation.
Summary of the invention
The object of the invention is exactly the defective to prior art, and a kind of amorphous catalyst of 2 cyano 4 nitro aniline catalytic hydrogenation is provided, and through this catalyst to catalyzing hydrogenating preparation 2,5-diaminobenzene nitrile method.Adopt catalyst of the present invention, 2 cyano 4 nitro aniline hydrogenation reaction conversion ratio is high, good, the technological operation safety of selectivity.
Technical scheme of the present invention is achieved in that it is made up of nickel, boron and transition metal M, and it is characterized in that: the molar percentage of each element is in the catalyst: Ni20-70%, B 30-60%, transition metal M 0-10%.
The present invention's technical scheme preferably is: the molar percentage of each element is in the catalyst: Ni 45%, B 50%, transition metal M 5%.Metallic nickel is that form with Ni-B or Ni-B-M amorphous alloy exists in the catalyst.Described transition metal M be among Fe, Co, Mo, the Cr one or more.The adding of boron forms easily that long-range is unordered, the amorphous alloy structure of shortrange order, helps improving the hydrogenation activity and the selectivity of catalyst.
The better technical scheme of the present invention is: metallic nickel is that form with the Ni-B-Co-Cr amorphous alloy exists in the catalyst.
Preparation of catalysts method of the present invention is: in temperature is in 0-100 ℃; The KBH4-NaOH mixed aqueous solution is added drop-wise in the aqueous solution of metal ion and reacts; Reacted 50-60 minute; To guarantee that metal ion reduces fully, wherein the molar percentage of metallic element is in the aqueous solution of metal ion: Ni20-70%, B30-60%, transition metal M 0-10%; Be washed till neutrality with deionized water then, use washing with alcohol, drying again.
The present invention 2; The preparation method of 5-diaminobenzene nitrile is: 2 cyano 4 nitro aniline is carried out hydrogenation reduction under the effect of catalyst; Make 2; 5-diaminobenzene nitrile, wherein said catalyst is made up of nickel, boron and transition metal M, and the molar percentage of each element is in the catalyst: Ni20-70%, B 30-60%, transition metal M 0-10%.
The present invention 2, and 5-diaminobenzene nitrile preparation method preferably is: metallic nickel is that form with Ni-B or Ni-B-M amorphous alloy exists in the described catalyst.Reasonable is that the molar percentage of each element in the described catalyst is: Ni 45%, B 50%, Co 2%, Cr3%.
Wherein the hydrogenation reduction condition is: reaction temperature 50-120 ℃, and reaction pressure 0.5-1.5MPa, reaction time 2-8 hour, the mass ratio of catalyst and raw material 2 cyano 4 nitro aniline was 0.005-0.025: 1.
Added boron element in the catalyst of the present invention, the adding of boron forms easily that long-range is unordered, the amorphous alloy structure of shortrange order, helps improving the hydrogenation activity and the selectivity of catalyst.Adopt catalyst of the present invention to carry out hydrogenating reduction, the cyanic acid in the 2 cyano 4 nitro aniline is not reduced, 2 cyano 4 nitro aniline hydrogenation reaction conversion ratio is high, good, the technological operation safety of selectivity.
The specific embodiment
Below in conjunction with embodiment the present invention is done and to further describe:
The preparation of embodiment 1.Ni-B-Co amorphous alloy catalyst and 2 cyano 4 nitro aniline hydrogenation are used
Greater than 13, concentration is that the 2.0M potassium borohydride aqueous solution is added drop-wise in the mixed solution of 2M nickel acetate and 0.2M cobalt acetate with freshly prepared pH value, and hierarchy of control reaction temperature is 25 ℃; Reaction 30min; Gained black precipitate centrifugation is washed till neutrality with distilled water, uses absolute ethanol washing again; Dry then, the mol ratio of element is Ni47.6%, B47.6%, Co4.8% in the obtained amorphous alloy catalyst.
In the 1L stainless steel autoclave, add 82g (0.5mol) 2 cyano 4 nitro aniline, 300ml methyl alcohol, the above-mentioned Ni-B-Co amorphous alloy catalyst of 0.5g; Hydrogen exchange three times fills hydrogen then to 1Mpa, is warming up to 80 ℃ under stirring; When Hydrogen Vapor Pressure drops to 0.5Mpa, fill hydrogen again to 1Mpa, when Hydrogen Vapor Pressure does not change, stop reaction, the reaction time is 4 hours; The reactant liquor cooling is filtered the catalyst preservation that obtains and is applied mechanically, and filtrating boils off solvent methanol through Rotary Evaporators and gets product 66.5g; Survey content 99.2%, yield 99.1%.
The preparation of embodiment 2.Ni-B-Cr amorphous alloy catalyst and 2 cyano 4 nitro aniline hydrogenation are used
With freshly prepared pH value greater than 13; Concentration is that the 2.0M potassium borohydride aqueous solution is added drop-wise in the mixed solution of 2.0M nickel acetate and 0.15M chromic nitrate, and hierarchy of control reaction temperature is 25 ℃, reaction 30min; Gained black precipitate centrifugation; Be washed till neutrality with distilled water, use absolute ethanol washing again, the mol ratio of element is Ni48.2%, B48.2%, Cr3.6%. in the obtained amorphous alloy catalyst
In the 1L stainless steel autoclave, add 82g (0.5mol) 2 cyano 4 nitro aniline, 300ml methyl alcohol, 0.5gNi-B-Cr amorphous alloy catalyst; Hydrogen exchange three times fills hydrogen then to 1Mpa, is warming up to 80 ℃ under stirring; When Hydrogen Vapor Pressure drops to 0.5Mpa, fill hydrogen again to 1Mpa, when Hydrogen Vapor Pressure does not change, stop reaction, the reaction time is 8 hours; The reactant liquor cooling is filtered the catalyst preservation that obtains and is applied mechanically, and filtrating boils off solvent methanol through Rotary Evaporators and gets product 66.6g; Survey content 99.4%, yield 99.3%.
The preparation of embodiment 3.Ni-B amorphous alloy catalyst and 2 cyano 4 nitro aniline hydrogenation are used
With freshly prepared pH value greater than 13; Concentration is that the 2.0M potassium borohydride aqueous solution is added drop-wise in the 2.0M nickel acetate solution, and hierarchy of control reaction temperature is 25 ℃, reaction 30min; Gained black precipitate centrifugation; Be washed till neutrality with distilled water, use absolute ethanol washing again, the mol ratio of element is Ni50%, B50% in the obtained amorphous alloy catalyst.
In the 1L stainless steel autoclave, add 82g (0.5mol) 2 cyano 4 nitro aniline, 300ml methyl alcohol, 0.5gNi-B amorphous alloy catalyst; Hydrogen exchange three times fills hydrogen then to 1Mpa, is warming up to 80 ℃ under stirring; When Hydrogen Vapor Pressure drops to 0.5Mpa, fill hydrogen again to 1Mpa, when Hydrogen Vapor Pressure does not change, stop reaction, the reaction time is 2 hours; The reactant liquor cooling is filtered the catalyst preservation that obtains and is applied mechanically, and filtrating boils off solvent methanol through Rotary Evaporators and gets product 66.2g; Survey content 99.0%, yield 98.6%.
The preparation of embodiment 4.Ni-B-Co-Cr amorphous alloy catalyst and 2 cyano 4 nitro aniline hydrogenation are used
With freshly prepared pH value greater than 13; Concentration is that the 2.0M potassium borohydride aqueous solution is added drop-wise in the mixed solution of 2.0M nickel acetate, 0.1M cobalt nitrate and 0.1M chromic nitrate, and hierarchy of control reaction temperature is 25 ℃, reaction 30min; Gained black precipitate centrifugation; Be washed till neutrality with distilled water, use absolute ethanol washing again, the mol ratio of element is Ni 45%, B 50%, Co 2%, Cr3% in the obtained amorphous alloy catalyst.
In the 1L stainless steel autoclave, add 82g (0.5mol) 2 cyano 4 nitro aniline, 300ml methyl alcohol, 0.5gNi-B-Co-Cr amorphous alloy catalyst; Hydrogen exchange three times fills hydrogen then to 1Mpa, is warming up to 80 ℃ under stirring; When Hydrogen Vapor Pressure drops to 0.5Mpa, fill hydrogen again to 1Mpa, when Hydrogen Vapor Pressure does not change, stop reaction, the reaction time is 5 hours; The reactant liquor cooling is filtered the catalyst preservation that obtains and is applied mechanically, and filtrating boils off solvent methanol through Rotary Evaporators and gets product 66.9g; Survey content 99.4%, yield 99.4%.
Comparative example 1.RaneyNi catalyst 2 cyano 4 nitro aniline hydrogenation
In the 1L stainless steel autoclave, add 82g (0.5mol) 2 cyano 4 nitro aniline, 300ml methyl alcohol, 0.5gRaneyNi catalyst; Hydrogen exchange three times fills hydrogen then to 1Mpa, is warming up to 80 ℃ under stirring; When Hydrogen Vapor Pressure drops to 0.5Mpa, fill hydrogen again to 1Mpa, when Hydrogen Vapor Pressure does not change, stop reaction, the reaction time is 4 hours; The reactant liquor cooling is filtered the catalyst preservation that obtains and is applied mechanically, and filtrating boils off solvent methanol through Rotary Evaporators and gets product 65.7g; Survey content 98.2%, yield 97.1%.
Claims (1)
1. one kind 2; The preparation method of 5-diaminobenzene nitrile, it is that 2 cyano 4 nitro aniline is carried out hydrogenation reduction under the effect of amorphous catalyst, makes 2; 5-diaminobenzene nitrile; The molar percentage of each element is in the wherein said amorphous catalyst: Ni 45%, B 50%, Co 2%, Cr3%, and the hydrogenation reduction condition is: reaction temperature 50-120 ℃, reaction pressure 0.5-1.5MPa; Reaction time 2-8 hour, the mass ratio of catalyst and raw material 2 cyano 4 nitro aniline was 0.005-0.025:1.
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CN102614881B (en) * | 2012-03-04 | 2013-08-14 | 浙江大学 | Method and used catalytic agent for synthesizing N-butylethylamine |
CN103896804B (en) * | 2014-04-28 | 2016-03-30 | 西安凯立新材料股份有限公司 | A kind of liquid phase catalytic hydrogenation prepares the method for 2,5-diamino cyanophenyl |
CN105753738B (en) * | 2016-04-05 | 2018-10-12 | 长春工业大学 | A kind of method of nitrobenzoyl catalytic hydrogenation of nitriles synthesizing amino benzonitrile |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1196975A (en) * | 1997-04-24 | 1998-10-28 | 中国石油化工总公司 | Non-crystalline alloy catalyst containing Ni and B, its prepn. and application |
CN1375357A (en) * | 2002-01-18 | 2002-10-23 | 南开大学 | Amorphous alloy catalyst for hydrogenating cyclobufene sultone and its prepn. and application |
CN1660774A (en) * | 2004-12-28 | 2005-08-31 | 浙江工业大学 | Method for preparing o-chloroaniline |
CN1666816A (en) * | 2004-03-11 | 2005-09-14 | 上海师范大学 | Co-Fe-B amorphous alloy catalyst, its preparation method and application |
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CN1196975A (en) * | 1997-04-24 | 1998-10-28 | 中国石油化工总公司 | Non-crystalline alloy catalyst containing Ni and B, its prepn. and application |
CN1375357A (en) * | 2002-01-18 | 2002-10-23 | 南开大学 | Amorphous alloy catalyst for hydrogenating cyclobufene sultone and its prepn. and application |
CN1666816A (en) * | 2004-03-11 | 2005-09-14 | 上海师范大学 | Co-Fe-B amorphous alloy catalyst, its preparation method and application |
CN1660774A (en) * | 2004-12-28 | 2005-08-31 | 浙江工业大学 | Method for preparing o-chloroaniline |
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