CN111116378A - Method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene - Google Patents
Method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene Download PDFInfo
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- CN111116378A CN111116378A CN201911327020.9A CN201911327020A CN111116378A CN 111116378 A CN111116378 A CN 111116378A CN 201911327020 A CN201911327020 A CN 201911327020A CN 111116378 A CN111116378 A CN 111116378A
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- dinitronaphthalene
- diaminonaphthalene
- selective reduction
- solvent
- catalyst
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- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 title claims abstract description 29
- AVCSMMMOCOTIHF-UHFFFAOYSA-N 1,8-dinitronaphthalene Chemical compound C1=CC([N+]([O-])=O)=C2C([N+](=O)[O-])=CC=CC2=C1 AVCSMMMOCOTIHF-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000009467 reduction Effects 0.000 title claims abstract description 24
- 230000002194 synthesizing effect Effects 0.000 title claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 8
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
- 239000010941 cobalt Substances 0.000 claims abstract description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 4
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 11
- 239000012295 chemical reaction liquid Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 239000002351 wastewater Substances 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 2
- 229910000510 noble metal Inorganic materials 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000007789 sealing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 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 1
- XNKFCDGEFCOQOM-UHFFFAOYSA-N 1,2-dinitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C21 XNKFCDGEFCOQOM-UHFFFAOYSA-N 0.000 description 1
- ZPSZXWVBMOMXED-UHFFFAOYSA-N 2-(2-bromo-5-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=CC=C1Br ZPSZXWVBMOMXED-UHFFFAOYSA-N 0.000 description 1
- UBZVRROHBDDCQY-UHFFFAOYSA-N 20749-68-2 Chemical compound C1=CC(N2C(=O)C3=C(C(=C(Cl)C(Cl)=C3C2=N2)Cl)Cl)=C3C2=CC=CC3=C1 UBZVRROHBDDCQY-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 1, 8-diaminonaphthalene by selectively reducing 1, 8-dinitronaphthalene, which is a method for only generating 1, 8-diaminonaphthalene by adding a catalyst into a solvent and controlling the temperature and time to completely reduce nitro groups. The solvent can be one of methanol, ethanol, isopropanol or DMF, the catalyst is one of nickel, cobalt, platinum and palladium noble metals, and the catalytic reduction only reduces nitro groups, so that the selectivity is high, the reduction rate is high, almost 100 percent of reduction is realized, the yield is high (more than 95 percent), the wastewater amount is less than 5 percent, the problems of incomplete reduction and low yield of the prior method are solved, and the method is suitable for industrial production. The purity of the 1, 8-diaminonaphthalene prepared by the method is up to more than 99%, the reduction rate of the raw material is high, almost 100% reduction is realized, the yield is higher than 95%, and the generated wastewater is less than 5% of the total yield.
Description
Technical Field
The invention relates to a method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene.
Background
1, 8-diaminonaphthalene is an important dye intermediate, with grayish-red to gray or dark-brown needle crystals of the formula C10H10N2CAS number: 479-27-6, molecular weight 158.1998, 1, 8-diaminonaphthalene is an important intermediate for preparing oil-soluble pigment, has annual output of over ten thousand tons, and is mainly used for synthesizing solvent orange 60 and solvent red 135, which are widely used for coloring polystyrene, organic glass, rigid polyvinyl chloride and ABS.
CN: 1100403A discloses a process for preparing 1, 5-diaminonaphthalene and 1, 8-diaminonaphthalene by mixing dinitronaphthalene, iron powder, alcohol, water, glacial acetic acid, caustic soda and sodium bisulfite in a certain proportion, stirring, heating, keeping warm, diluting, precipitating, filtering and drying, which has serious environmental pollution and is a useless process route in the near future for the clear text of the state.
101823968 discloses a method for preparing 1, 8-diaminonaphthalene by reducing 1, 8-dinitronaphthalene with hydrazine hydrate, but the catalyst has the advantages of low activity, low selectivity, low yield and high cost, and is suitable for reducing short-line aromatic hydrocarbon.
CN: 101187031A adopts dilute sulfuric acid solution as electrolyte, and 1, 8-dinitronaphthalene is electrolytically reduced under the drive of constant potential through four steps of equipment preparation, electrolyte preparation, electrolysis and post-treatment, and the yield is 36.2-75.5%. It is difficult to use in industrial production due to the low yield.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects that the reduction rate is lower than 80 percent and the yield is lower than 70 percent in the production of 1, 8-dinitronaphthalene in the prior art, and provides a method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene, which can improve the reduction rate and the yield.
In order to solve the technical problems, the invention provides the following technical scheme:
a method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene comprises the following steps:
s1, sequentially adding 1, 8-dinitronaphthalene, a solvent and a catalyst into a hydrogenation high-pressure kettle, replacing air in the kettle, adding hydrogen after replacement, keeping the pressure in the kettle at 1.5-3MPa, starting stirring, heating to 55-75 ℃ in the kettle, preserving heat for reaction, and finishing the reaction;
s2, taking out the reaction liquid in the S1, performing suction filtration on the reaction liquid, and filtering out the catalyst;
s3, distilling the filtrate of S2 under reduced pressure, evaporating the solvent and recovering the solvent;
and S4, cooling and crystallizing to obtain the 1, 8-diaminonaphthalene solid.
Further, the catalyst used in S1 is any one of nickel, cobalt, platinum, palladium or Pd. These catalysts can lower the activation energy and facilitate the breaking of old bonds and the formation of new bonds. These metals may be used as a catalyst, may be adsorbed on C, or may be used as an active adsorbent, or may be ionic.
Further, the solvent used in S1 is any one of methanol, ethanol, isopropanol or DMF. Ethanol or isopropanol is preferred.
Further, the heat preservation time is 4-12 hours.
Furthermore, the amount of solvent used in S1 is 8-12 times the mass of 1, 8-dinitronaphthalene.
Further, the distillation temperature in S3 is 45-55 ℃.
Further, the crystallization temperature in S4 is below-10 ℃.
On the other hand, the selection of the catalyst is closely related to the solvent of the reaction, the magnitude of the pressure, the temperature of the reaction and the time, and the adjustment of one catalyst can generate great difference, so that the results have great difference, and the ideal yield can not be obtained by simple experiments.
The invention has the following beneficial effects: the invention discloses a method for preparing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene, which is a method for only generating 1, 8-diaminonaphthalene by adding a catalyst into a solvent and controlling the temperature and time to completely reduce nitro groups. The solvent can be one of methanol, ethanol, isopropanol or DMF, the catalyst is one of nickel, cobalt, platinum and palladium noble metals, and the catalytic reduction only reduces nitro groups, so that the selectivity is high, the reduction rate is high, almost 100 percent of reduction is realized, the yield is high (more than 95 percent), the wastewater amount is less than 5 percent, the problems of incomplete reduction and low yield of the prior method are solved, and the method is suitable for industrial production. The purity of the 1, 8-diaminonaphthalene prepared by the method is up to more than 99%, the reduction rate of the raw material is high, the raw material can be reduced by 100%, the impurities are few, the boiling point of the solvent is low, the distillation is easy, the yield is high, the yield is up to more than 95%, and the generated waste water is little and less than 5% of the total amount.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Example 1
The first step is as follows: taking 30g of 1, 8-dinitronaphthalene and 300g of ethanol, adopting Pd as a catalyst, adsorbing the Pd on C to prepare Pd/C, wherein the addition amount of the Pd/C is 1.7g, and the mass percent of the Pd is about 5%, so that the catalyst has a good catalytic effect and is low in price; adding the mixture into a high-pressure reaction kettle, sealing the reaction kettle, replacing the air in the kettle with nitrogen for about 3 times, and replacing the nitrogen with hydrogen for about 3 times;
the second step is that: heating the temperature in the kettle to 65 ℃, and keeping the temperature for 6 hours, wherein the pressure is controlled to be 1.5 MPa;
the third step: after the reaction is finished, taking out reaction liquid, filtering out the catalyst, distilling out the solvent under reduced pressure, cooling to below-10 ℃, crystallizing and filtering out 20.6g of the product 1, 8-diaminonaphthalene. The purity of the product is over 97.2 percent and the yield is 94.7 percent.
Example 2
The first step is as follows: adding 80g of 1, 8-dinitronaphthalene, 300g of isopropanol and 4.8g of Pd/C into a high-pressure reaction kettle, sealing the reaction kettle, replacing the air in the kettle with nitrogen for about 3 times, and replacing the nitrogen with hydrogen for about 3 times;
the second step is that: heating the temperature in the kettle to 65 ℃, and keeping the temperature for 4 hours, wherein the pressure is controlled to be 1.5 MPa;
the third step: after the reaction is finished, taking out reaction liquid, filtering out the catalyst, distilling out the solvent under reduced pressure, cooling to the temperature of below-10 ℃, crystallizing and filtering out 55.8g of the product 1, 8-diaminonaphthalene, and detecting that the product purity is more than 98.3 percent and the yield is 96.2 percent.
Example 3
Adding 30g of 1, 8-dinitronaphthalene, 300g of ethanol and 1.8g of Pd/C into a high-pressure reaction kettle, sealing the reaction kettle, replacing the air in the kettle with nitrogen for about 3 times, and replacing the nitrogen with hydrogen for about 3 times;
the second step is that: heating the temperature in the kettle to 70 ℃, and keeping the temperature for 10 hours, wherein the pressure is controlled to be 2 MPa;
the third step: after the reaction is finished, taking out reaction liquid, filtering out the catalyst, distilling out the solvent under reduced pressure, cooling to below-10 ℃, crystallizing and filtering out 21.2g of the product 1, 8-diaminonaphthalene with the purity of 99.1 percent and the yield of 97.7 percent.
Example 4
The first step is as follows: adding 80g of 1, 8-dinitronaphthalene, 300g of isopropanol and Pd/C4.8g into a high-pressure reaction kettle, sealing the reaction kettle, replacing the air in the kettle with nitrogen for about 3 times, and replacing the nitrogen with hydrogen for about 3 times;
the second step is that: heating the temperature in the kettle to 70 ℃, and keeping the temperature for 6 hours, wherein the pressure is controlled to be 2 MPa;
the third step: after the reaction is finished, taking out reaction liquid, filtering out the catalyst, distilling out the solvent under reduced pressure, cooling to the temperature of below-10 ℃, crystallizing and filtering out 57.1g of the product 1, 8-diaminonaphthalene, and detecting that the product purity is 99.4 percent and the yield is 98.5 percent.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene is characterized by comprising the following steps:
s1, sequentially adding 1, 8-dinitronaphthalene, a solvent and a catalyst into a hydrogenation high-pressure kettle, replacing air in the kettle, adding hydrogen after replacement, keeping the pressure in the kettle at 1.5-3MPa, starting stirring, heating to 55-75 ℃ in the kettle, preserving heat for reaction, and finishing the reaction;
s2, taking out the reaction liquid in the S1, performing suction filtration on the reaction liquid, and filtering out the catalyst;
s3, distilling the filtrate of S2 under reduced pressure, evaporating the solvent and recovering the solvent;
and S4, cooling and crystallizing to obtain the 1, 8-diaminonaphthalene solid.
2. The method for selective reduction of 1, 8-dinitronaphthalene to 1, 8-diaminonaphthalene according to claim 1, wherein the catalyst used in S1 is any one of nickel, cobalt, platinum, palladium or Pd.
3. The method for selective reduction of 1, 8-dinitronaphthalene to 1, 8-diaminonaphthalene according to claim 1, wherein the solvent used in S1 is any one of methanol, ethanol, isopropanol or DMF.
4. The method for selective reduction of 1, 8-dinitronaphthalene to 1, 8-diaminonaphthalene according to claim 1, wherein the holding time in S1 is 4 to 12 hours.
5. The method for the selective reduction synthesis of 1, 8-diaminonaphthalene according to claim 1, 8-dinitronaphthalene, wherein the mass of the solvent used in S1 is 8 to 12 times the mass of 1, 8-dinitronaphthalene.
6. The method for the selective reduction of 1, 8-dinitronaphthalene to 1, 8-diaminonaphthalene according to claim 1, wherein the distillation temperature in S3 is 45-55 ℃.
7. The method for the selective reduction of 1, 8-dinitronaphthalene to 1, 8-diaminonaphthalene according to claim 1, wherein the crystallization temperature in S4 is below-10 ℃.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911327020.9A CN111116378A (en) | 2019-12-20 | 2019-12-20 | Method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene |
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| CN201911327020.9A CN111116378A (en) | 2019-12-20 | 2019-12-20 | Method for synthesizing 1, 8-diaminonaphthalene by selective reduction of 1, 8-dinitronaphthalene |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115448868A (en) * | 2022-07-25 | 2022-12-09 | 青海黄河上游水电开发有限责任公司西宁太阳能电力分公司 | Method for strengthening catalytic hydrogenation reaction of nitro compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4026944A (en) * | 1974-08-10 | 1977-05-31 | Bayer Aktiengesellschaft | Process for manufacturing diaminonaphthalene |
| CN101575295A (en) * | 2009-05-20 | 2009-11-11 | 江苏工业学院 | A kind of method that dinitronaphthalene catalytic hydrogenation prepares diaminonaphthalene |
| CN102924298A (en) * | 2012-11-15 | 2013-02-13 | 泰莱斯（南通）医药化工有限公司 | Separation method of 1,5-diaminonaphthalene and 1,8-diaminonaphthalene |
-
2019
- 2019-12-20 CN CN201911327020.9A patent/CN111116378A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4026944A (en) * | 1974-08-10 | 1977-05-31 | Bayer Aktiengesellschaft | Process for manufacturing diaminonaphthalene |
| CN101575295A (en) * | 2009-05-20 | 2009-11-11 | 江苏工业学院 | A kind of method that dinitronaphthalene catalytic hydrogenation prepares diaminonaphthalene |
| CN102924298A (en) * | 2012-11-15 | 2013-02-13 | 泰莱斯（南通）医药化工有限公司 | Separation method of 1,5-diaminonaphthalene and 1,8-diaminonaphthalene |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115448868A (en) * | 2022-07-25 | 2022-12-09 | 青海黄河上游水电开发有限责任公司西宁太阳能电力分公司 | Method for strengthening catalytic hydrogenation reaction of nitro compound |
| CN115448868B (en) * | 2022-07-25 | 2024-01-26 | 青海黄河上游水电开发有限责任公司西宁太阳能电力分公司 | Method for strengthening catalytic hydrogenation reaction of nitro compound |
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