CN101081818A - Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound - Google Patents
Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound Download PDFInfo
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- CN101081818A CN101081818A CNA2007100118056A CN200710011805A CN101081818A CN 101081818 A CN101081818 A CN 101081818A CN A2007100118056 A CNA2007100118056 A CN A2007100118056A CN 200710011805 A CN200710011805 A CN 200710011805A CN 101081818 A CN101081818 A CN 101081818A
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- methoxyl
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- anisidine
- alloy
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- -1 methoxyl nitro compound Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 9
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 title abstract 3
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 229910045601 alloy Inorganic materials 0.000 claims abstract description 13
- 239000000956 alloy Substances 0.000 claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 5
- 229910052742 iron Inorganic materials 0.000 claims abstract description 5
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010791 quenching Methods 0.000 claims abstract description 3
- 230000000171 quenching effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 21
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012018 catalyst precursor Substances 0.000 claims description 6
- 238000004904 shortening Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000906 Bronze Inorganic materials 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 229910000808 amorphous metal alloy Inorganic materials 0.000 claims description 2
- 239000010974 bronze Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 239000010419 fine particle Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000001577 simple distillation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000003965 capillary gas chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- PDIKQPGNGBZFRQ-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)benzene-1,4-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(OC)=CC=C1NC1=CC=C(N)C=C1.C1=CC(OC)=CC=C1NC1=CC=C(N)C=C1 PDIKQPGNGBZFRQ-UHFFFAOYSA-N 0.000 description 1
- MRQIXHXHHPWVIL-ISLYRVAYSA-N Sudan I Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 MRQIXHXHHPWVIL-ISLYRVAYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention belongs to the field of application technology of skeleton nickel, and is especially high selectivity catalytic process of hydrogenating methoxyl nitro compound to produce methoxyl aniline. Under mild condition, methoxyl nitrobenzene is hydrogenated selectively in the presence of catalyst. The main catalyst has precursor of NiAlM alloy prepared through high temperature melting and quenching, with the modifying component M is one of Fe, Mn, Mo, Cr and W, or their proper combination. The precursor is activated in water solution of NaOH to eliminate Al to form skeleton nickel-base catalyst with very high hydrogenating activity and selectivity. Methoxyl aniline may be prepared through one-step reaction in yield over 99 %, and the preparation process has high selectivity, stable catalyst activity, long catalyst service life, reuseability of the catalyst and low cost.
Description
Technical field
The invention belongs to the applied technical field of shortening.Relate to the application in the preparation anisidine of Ni-based high reactivity of a class skeleton and high-selectivity hydrogenation catalyst.This technology can be selected hydrogenation preparing with methoxy nitrobenzene under mild conditions be highly purified anisidine.
Background technology
Anisidine is important organic intermediate, is widely used in the preparation of dyestuff, medicine, pigment, spices product.For example, P-nethoxyaniline is used for synthetic ice dyestuff, as purplish red color base GP, Fast Blue VB salt, azoic coupling component AS-RL, azoic coupling component AS-SG, the blue B look salt of peace peace, direct everbright fast orange F3G and reactive dyestuffs etc., anisidine also is important medicine intermediate, such as being used for the synthetic of " Quinacrime ".
Anisidine makes by the reduction of methoxy nitrobenzene usually.Domestic manufacturing enterprise still uses with serious pollution iron powder method and sulfuration alkaline process in a large number at present, and replacing these backward technologies with cleaning technique has been trend of the times.The shortening technology uses hydrogen to be reductive agent, and reaction orientation is carried out, and does not produce harmful side product, and waste gas and waste liquid discharging is few, does not relate to strong acid, highly basic medium, has the technology advanced person, yield height, good product quality, advantage such as environmentally friendly.Therefore, the technology of methoxy nitrobenzene efficient catalytic hydrogenation preparing anisidine has great importance.
Summary of the invention
The object of the present invention is to provide a kind of simple and easy, repeated a kind of methoxyl nitro compound object height selective catalytic hydrogenation good and lower production cost to prepare the method for anisidine, the compound of reaction type is:
Technical solution of the present invention is: a kind of methoxyl nitro compound object height selective catalytic hydrogenation prepares the method for anisidine, reaction conditions is: add raw material methoxy nitrobenzene, solvent and modified skeletal nickel catalyst in still formula high-pressure reactor, the mass percent of catalyzer and reaction solution is 0.5～15wt%, and solvent and neighbour or a mass ratio to methoxy nitrobenzene are 20: 1～1: 1; Reaction pressure is normal pressure～10MPa, and temperature of reaction is room temperature～200 ℃, stirs reaction 0.5～4h down; After reaction finished, cooling was left standstill, and took out supernatant liquid simple distillation and can obtain product, and catalyst recirculation is used.The composition of catalyzer and preparation method are:
A, catalyst precursor are made up of Primary Catalysts and promotor, Primary Catalysts is a nickel, promotor is one or more the mixing among Al, Mo, Fe, Mn, Cr, the Cu, and integral body is expressed as NiM, and wherein component M is one or more mixing of Al, Mo, Fe, Mn, Cr, Cu;
The preparation method of b, catalyst precursor alloy alloy is: with solid Ni, Al, M according to mass percent Ni:30-60%, Al:60-30%, the ratio of M:0.1-10% is warmed up to 1000-1600 ℃ under argon shield, make its fusing form the uniform alloy liquation, the fused alloy uses the cooling bronze drum quenching of high speed rotating to 30-80 ℃ in argon gas atmosphere, form the thin bar of amorphous alloy, become fine particle with ball mill grinding then, the catalyst powder art of selecting the different grain size scope with sub-sieve is standby, and normally used size range is the 10-100 micron;
The activation method of c, catalyst precursor alloy, powdered alloy is slowly joined in 10～25%NaOH solution, launch to remove in 15～120 minutes Al down, with the washing of deoxidation deionized water repeated multiple times at 70～105 ℃, be neutral to solution, form skeleton nickel based structures catalyzer.
First-selected range of reaction temperature is 60～100 ℃, and the reaction pressure scope is normal pressure～5Mpa.Described solvent is: the mixture of one or more in methyl alcohol, ethanol, Virahol, tetrahydrofuran (THF), hexanaphthene, sherwood oil, dioxane, perhydronaphthalene, benzene, toluene, ethylbenzene, the hexahydroaniline.Described methoxy nitrobenzene comprises that O-methoxy oil of mirbane, meta-methoxy oil of mirbane reach methoxy nitrobenzene.
The invention has the beneficial effects as follows:
1, the methoxy nitrobenzene shortening prepares in the anisidine process, and production technique is simple, and cleanliness without any pollution is fit to suitability for industrialized production.
2, the methoxy nitrobenzene shortening prepares in the anisidine process, adopts relatively mild reaction conditions, has overcome the high request of severe condition to production unit.
3, catalyst activity is stable, and the life-span is long, and can apply mechanically repeatedly, has reduced production cost.
Embodiment
The present invention is further illustrated below in conjunction with embodiment.
Embodiment 1
In being the still formula high-pressure reactor of 70mL, volume puts into 6g to methoxy nitrobenzene, the 20mL solvent, 0.5g catalyzer, airtight back be with nitrogen replacement air three times, and then with hydrogen exchange nitrogen three times, charge into 0.5MPa hydrogen then, put into slowly heat temperature raising of water-bath, adjust hydrogen valve, make system pressure reach 1MPa, after 30 minutes, reaction is finished.Capillary gas chromatography is carried out in the sampling of cooling back, to methoxy nitrobenzene transformation efficiency 100%, and p-aminophenyl amine selectivity 100%.
Embodiment 2
In being the still formula high-pressure reactor of 70mL, volume puts into 6g O-methoxy oil of mirbane, the 20mL solvent, 0.5g catalyzer, airtight back is with nitrogen replacement air three times, and then with hydrogen exchange nitrogen three times, puts into the slow heat temperature raising of water-bath, adjust hydrogen valve, make system pressure reach 1.5MPa, after 30 minutes, reaction is finished.The sampling carrying out of cooling back capillary gas chromatography, O-methoxy oil of mirbane transformation efficiency 100%, ORTHO ANISIDINE selectivity 100%.
Embodiment 3
In being the still formula high-pressure reactor of 70mL, volume puts into 6g meta-methoxy oil of mirbane, the 20mL solvent, 0.5g catalyzer, airtight back be with nitrogen replacement air three times, and then with hydrogen exchange nitrogen three times, charge into 0.5MPa hydrogen then, put into slowly heat temperature raising of water-bath, adjust hydrogen valve, make system pressure reach 2.0MPa, kept 1 hour, reaction is finished.The sampling carrying out of cooling back capillary gas chromatography, meta-methoxy oil of mirbane transformation efficiency 100%, m-anisidine selectivity 100%.
Claims (6)
1, a kind of methoxyl nitro compound object height selective catalytic hydrogenation prepares the method for anisidine, it is characterized in that, reaction conditions is: add raw material methoxy nitrobenzene, solvent and modified skeletal nickel catalyst in still formula high-pressure reactor, the mass percent of catalyzer and reaction solution is 0.5～15wt%, and solvent and neighbour or a mass ratio to methoxy nitrobenzene are 20: 1～1: 1; Reaction pressure is normal pressure～10MPa, and temperature of reaction is room temperature～200 ℃, stirs reaction 0.5～4h down; After reaction finished, cooling was left standstill, and took out supernatant liquid simple distillation and can obtain product, and catalyst recirculation is used.
2, a kind of methoxyl nitro compound object height selective catalytic hydrogenation according to claim 1 prepares the method for anisidine, it is characterized in that the composition of described catalyzer and preparation method are:
A, catalyst precursor are made up of Primary Catalysts and promotor, Primary Catalysts is a nickel, promotor is one or more the mixing among Al, Mo, Fe, Mn, Cr, the Cu, and integral body is expressed as NiM, and wherein component M is one or more mixing of Al, Mo, Fe, Mn, Cr, Cu;
The preparation method of b, catalyst precursor alloy alloy is: with solid Ni, Al, M according to mass percent Ni:30-60%, Al:60-30%, the ratio of M:0.1-10% is warmed up to 1000-1600 ℃ under argon shield, make its fusing form the uniform alloy liquation, the fused alloy uses the cooling bronze drum quenching of high speed rotating to 30-80 ℃ in argon gas atmosphere, form the thin bar of amorphous alloy, become fine particle with ball mill grinding then, the catalyst fines of selecting the different grain size scope with sub-sieve is standby, and normally used size range is the 10-100 micron;
The activation method of c, catalyst precursor alloy, the alloy powder art is slowly joined in 10～25%NaOH solution, launch to remove in 15～120 minutes Al down, with the washing of deoxidation deionized water repeated multiple times at 70～105 ℃, be neutral to solution, form skeleton nickel based structures catalyzer.
3, a kind of methoxyl nitro compound object height selective catalytic hydrogenation according to claim 1 prepares the method for anisidine, it is characterized in that described range of reaction temperature is 60～100 ℃.
4, a kind of methoxyl nitro compound object height selective catalytic hydrogenation according to claim 1 prepares the method for anisidine, it is characterized in that described reaction pressure scope is normal pressure～5Mpa.
5, a kind of methoxy nitrobenzene highly selective shortening according to claim 1 prepares the method for anisidine, it is characterized in that described solvent is: the mixture of one or more in methyl alcohol, ethanol, Virahol, tetrahydrofuran (THF), hexanaphthene, sherwood oil, dioxane, perhydronaphthalene, benzene, toluene, ethylbenzene, the hexahydroaniline.
6, a kind of methoxy nitrobenzene highly selective shortening according to claim 1 prepares the method for anisidine, it is characterized in that, described methoxy nitrobenzene comprises that O-methoxy oil of mirbane, meta-methoxy oil of mirbane reach methoxy nitrobenzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100118056A CN101081818A (en) | 2007-06-18 | 2007-06-18 | Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100118056A CN101081818A (en) | 2007-06-18 | 2007-06-18 | Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound |
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| Publication Number | Publication Date |
|---|---|
| CN101081818A true CN101081818A (en) | 2007-12-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100118056A Pending CN101081818A (en) | 2007-06-18 | 2007-06-18 | Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101805318A (en) * | 2010-04-09 | 2010-08-18 | 大连理工大学 | Method for preparing succinic anhydride in high-selective and hydrogenating manner by using quenching Raney nickel to catalyze maleic anhydride under mild condition |
| 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 |
| 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 |
| CN101481314B (en) * | 2008-11-07 | 2012-05-23 | 甘肃中科药源生物工程有限公司 | Method for preparing X substituted aniline from X substituted nitrobenzene |
| CN101514162B (en) * | 2008-11-07 | 2012-05-23 | 甘肃中科药源生物工程有限公司 | Method for preparing X-substituted diaminobenzene from X-substituted dinitrobenzene |
| CN103302257A (en) * | 2013-06-07 | 2013-09-18 | 苏州市泰力达科技有限公司 | Preparation method of aniline hydrogenating amorphous nickel-aluminum catalyst |
| CN101475488B (en) * | 2008-11-07 | 2014-06-18 | 甘肃中科药源生物工程有限公司 | Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene |
| CN108191675A (en) * | 2014-06-11 | 2018-06-22 | 宁夏中盛新科技有限公司 | The method that paraphenetidine is prepared with the device catalytic hydrogenation of industrially scalable |
| CN109053462A (en) * | 2018-08-14 | 2018-12-21 | 浙江今晖新材料股份有限公司 | A kind of preparation method of para-fluoroaniline |
| CN109647457A (en) * | 2018-12-06 | 2019-04-19 | 中国科学院山西煤炭化学研究所 | A kind of naphthalene adds the catalyst and preparation method and application of hydrogen naphthane and decahydronaphthalene |
-
2007
- 2007-06-18 CN CNA2007100118056A patent/CN101081818A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481314B (en) * | 2008-11-07 | 2012-05-23 | 甘肃中科药源生物工程有限公司 | Method for preparing X substituted aniline from X substituted nitrobenzene |
| CN101514162B (en) * | 2008-11-07 | 2012-05-23 | 甘肃中科药源生物工程有限公司 | Method for preparing X-substituted diaminobenzene from X-substituted dinitrobenzene |
| CN101475488B (en) * | 2008-11-07 | 2014-06-18 | 甘肃中科药源生物工程有限公司 | Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene |
| CN101805318A (en) * | 2010-04-09 | 2010-08-18 | 大连理工大学 | Method for preparing succinic anhydride in high-selective and hydrogenating manner by using quenching Raney nickel to catalyze maleic anhydride under mild condition |
| 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 |
| CN101823972B (en) * | 2010-05-05 | 2015-03-25 | 江苏利田科技股份有限公司 | Process for cleanly producing o (p) - aminoanisole (phenetidine) by coupling simulated moving bed |
| 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 |
| CN103302257A (en) * | 2013-06-07 | 2013-09-18 | 苏州市泰力达科技有限公司 | Preparation method of aniline hydrogenating amorphous nickel-aluminum catalyst |
| CN108191675A (en) * | 2014-06-11 | 2018-06-22 | 宁夏中盛新科技有限公司 | The method that paraphenetidine is prepared with the device catalytic hydrogenation of industrially scalable |
| CN108250085A (en) * | 2014-06-11 | 2018-07-06 | 宁夏明盛染化有限公司 | The method that paraphenetidine is prepared with the device catalytic hydrogenation of industrially scalable |
| CN109053462A (en) * | 2018-08-14 | 2018-12-21 | 浙江今晖新材料股份有限公司 | A kind of preparation method of para-fluoroaniline |
| CN109647457A (en) * | 2018-12-06 | 2019-04-19 | 中国科学院山西煤炭化学研究所 | A kind of naphthalene adds the catalyst and preparation method and application of hydrogen naphthane and decahydronaphthalene |
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