CN116082170A - Preparation method of 4,4' -diaminodiphenyl ether - Google Patents
Preparation method of 4,4' -diaminodiphenyl ether Download PDFInfo
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- CN116082170A CN116082170A CN202211630355.XA CN202211630355A CN116082170A CN 116082170 A CN116082170 A CN 116082170A CN 202211630355 A CN202211630355 A CN 202211630355A CN 116082170 A CN116082170 A CN 116082170A
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- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 238000002425 crystallisation Methods 0.000 claims description 19
- 230000008025 crystallization Effects 0.000 claims description 19
- MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- 239000012043 crude product Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 238000006073 displacement reaction Methods 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
- 239000004642 Polyimide Substances 0.000 description 7
- 229920001721 polyimide Polymers 0.000 description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the field of fine chemical engineering, and in particular relates to a preparation method of 4,4' -diaminodiphenyl ether. The invention prevents the reaction from generating byproducts by controlling the whole reaction stage to the post-treatment stage under the anaerobic environment and adding the antioxidant, so that the prepared product has high purity and good color. The preparation method provided by the invention has high raw material utilization rate, and the raw material utilization rate is more than 95%.
Description
The application is a divisional application of 2021, 02 and 25 months, CN202110210159.6 and entitled "preparation method of 4,4' -diaminodiphenyl ether".
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a preparation method of 4,4' -diaminodiphenyl ether.
Background
4,4' -diaminodiphenyl ether (4, 4' -Diaminodiphenyl ether or 4,4' -Oxydianiline) is called DADPE or ODA for short, and is a fine chemical intermediate with high added value. The Polyimide (PI) is a main monomer for synthesizing Polyimide, polymaleimide and other heat-resistant plastics, wherein the Polyimide (PI) has the advantages of high temperature resistance, high radiation resistance, high mechanical strength and the like, and is used for the aspects of films, coatings, fibers, foamed plastics, photoresist and the like. The continuous use temperature of the PI film reaches 250 ℃, and the short-term use temperature can even reach 450 ℃, so that the PI film can be widely applied to the fields of aviation, navigation, atomic energy, electronic and electric appliance industry and the like. ODA is also a curing agent for synthetic epoxy resins, an intermediate for dyes, a synthetic raw material for fragrances, and the like.
The industrial synthesis of ODA uses DNDPE as a raw material, reduces symmetrical nitro groups to amino groups, and then refines the amino groups. Depending on the reduction method, the non-catalytic hydrogenation reduction method and the catalytic hydrogenation reduction method can be classified. The non-catalytic hydrogenation method has high production cost and the reaction process is not well controlled; the product yield is low and the quality is poor; and the waste water and the iron mud waste residues are more, so that the environmental pollution is serious. The catalytic hydrogenation reduction method for synthesizing ODA has been industrialized abroad, and the process is simple, the raw material hydrogen is low in price and cannot corrode equipment although the high pressure has high requirements on equipment and technical operation, and the prepared product has high yield, high purity, economy and environmental protection and is suitable for continuous production.
US 3192263 adds refined DNDPE, DMA and 1% Pt/C into a glass enamel reactor, and carries out hydrogenation reaction for 2 hours at 83-87 ℃ and normal pressure, wherein the ODA yield is 90%. And transferring the DNDPE just prepared into an autoclave, and carrying out hydrogenation reaction at 50-60 ℃ and 2.7-3.4 MPa, wherein the ODA yield is 94%, which shows that the high-pressure catalytic hydrogenation effect is obvious. The hydrazine and the aqueous solution of sodium bisulphite are added during the post-treatment, so that the product can be prevented from being wet or oxidized. CN1807399a in a volume ratio of methanol to DMF of 1: mixing 0.2-0.5% as solvent, adding DNDPE, 3% and 5% Pd/C to react at 95-100 deg.C and 0.4MPa to obtain ODA with yield of 90.9% and 91.8% respectively. But the purity of the preparation method is low, the process is complex, and the cost is high.
Disclosure of Invention
Aiming at the problems existing in the process of preparing 4,4'-diaminodiphenyl ether by the catalytic method at the present stage, the invention provides a preparation method of 4,4' -diaminodiphenyl ether, which is characterized in that the reaction environment is controlled to contain no oxygen, and the addition of an antioxidant is combined, so that a high-purity product is finally prepared.
The technical scheme of the invention is as follows:
a method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) Uniformly stirring DMF and toluene, adding 4,4 '-dinitrodiphenyl ether, and heating to dissolve the 4,4' -dinitrodiphenyl ether to obtain a mixed material;
(2) Adding a catalyst into the mixture, N 2 Introducing hydrogen for reaction after gas displacement to obtain a reaction solution;
(3) Filtering the obtained reaction liquid to recover the catalyst, adding an antioxidant into the obtained filtrate, replacing with hydrogen, heating for dissolution, and adding water for crystallization; filtering to obtain a solid crude product;
(4) And washing the solid crude product by methanol, centrifugally filtering, and drying in vacuum to obtain the 4,4' -diaminodiphenyl ether.
And (3) adding active carbon in the step (1), and removing the active carbon by reflux filtration.
Before the catalyst is put into the step (2), N 2 Filtering under atmosphere to remove insoluble substances.
The reaction conditions of the step (2) are as follows: the temperature is 60-80 ℃ and the pressure is less than or equal to 1MPA.
The catalyst in the step (2) is a platinum-carbon catalyst.
The weight ratio of platinum in the platinum-carbon catalyst is as follows: 3-8%.
The antioxidant in the step (3) is as follows: EDTA; the addition amount is 0.05-0.1% of 4,4' -dinitrodiphenyl ether.
The antioxidant is added twice, and before water adding crystallization and after water adding crystallization.
The water drop speed in the step (3) of adding water for crystallization is 3-4 kg/min; the water addition is as follows: the weight ratio of the raw materials to the feed liquid is 1:1; the dripping is required to be completed when the temperature in the crystallization kettle is reduced to 40-50 ℃.
The invention has the beneficial effects that:
according to the invention, no oxygen is ensured in the reaction of adding the catalyst, no oxygen is ensured in the filtering process, no oxygen is ensured in the crystallization process, and finally, the antioxidant is added to prevent reaction byproducts, so that the prepared product has high purity and good color.
The adopted catalyst is a platinum carbon catalyst, the cost price is much lower than that of a palladium carbon catalyst in the market, but the catalytic effect is equivalent.
The utilization rate of the product is high, and the utilization rate of the raw materials of the process product is more than 95%.
Detailed Description
Example 1
A method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) 10kg of DMF and 10kg of toluene are stirred uniformly; 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised until the 4,4' -dinitrodiphenyl ether is dissolved;
(2) Platinum carbon catalyst with 8% platinum content is added, N 2 After the gas displacement, introducing hydrogen with the flow of 7L/h; reacting for 2h at 60 ℃ under 1 MPA;
(3) Recovering the catalyst, adding 0.8kg of aromatic amine antioxidant 5057 into the filtrate, replacing by hydrogen, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; the addition amount of water is 20kg; the temperature in the crystallization kettle is required to be reduced to 40-50 ℃ to finish dripping; adding 0.6kg of aromatic amine antioxidant 5057; filtering to obtain a crude product;
(4) The crude product is washed by methanol, centrifugally filtered and dried in vacuum.
Example 2
A method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) 11kg of DMF and 10kg of toluene are stirred uniformly; 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised until the 4,4' -dinitrodiphenyl ether is dissolved;
(2) Adding platinum carbon catalyst with 3% platinum content and N 2 Introducing hydrogen after gas displacement; the flow is 8L/h; reacting for 2h at 80 ℃ under 0.4 MPA;
(3) Recovering the catalyst, adding 0.5kg of aromatic amine antioxidant triphenyl phosphite into the filtrate, replacing with hydrogen, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; 15kg of water; the temperature in the crystallization kettle is required to be reduced to 40-50 ℃ to finish dripping; adding 0.8kg of triphenyl phosphite serving as an aromatic amine antioxidant; filtering to obtain a crude product;
(4) The crude product is washed by methanol, centrifugally filtered and dried in vacuum.
Example 3
A method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) 11kg of DMF and 10kg of toluene are stirred uniformly; 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised until the 4,4' -dinitrodiphenyl ether is dissolved;
(2) Platinum carbon catalyst with 5% platinum content and N 2 Introducing hydrogen after gas displacement; the flow is 9L/h; reacting for 2h at 70 ℃ under 0.5 MPA;
(3) Recovering the catalyst, adding 1.2kg of aromatic amine antioxidant 5057 into the filtrate, replacing by hydrogen, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; the addition amount of water is 18kg; the temperature in the crystallization kettle is required to be reduced to 40-50 ℃ to finish dripping; adding 0.6kg of aromatic amine antioxidant 5057; filtering to obtain a crude product;
(4) The crude product is washed by methanol, centrifugally filtered and dried in vacuum.
Comparative example 1
A method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) 11kg of DMF and 10kg of toluene are stirred uniformly; 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised until the 4,4' -dinitrodiphenyl ether is dissolved;
(2) Platinum carbon catalyst with 5% platinum content and N 2 Introducing hydrogen after gas displacement; the flow is 8L/h; reacting for 2h at 70 ℃ under 0.5 MPA;
(3) Recovering the catalyst, performing hydrogen replacement on the filtrate, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; the addition amount of water is 15kg; the temperature in the crystallization kettle is required to be reduced to 40-50 ℃ to finish dripping; filtering to obtain a crude product;
(4) The crude product is washed by methanol, centrifugally filtered and dried in vacuum.
Comparative example 2
A method for preparing 4,4' -diaminodiphenyl ether, comprising the following steps:
(1) 11kg of DMF and 10kg of toluene are stirred uniformly; 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised until the 4,4' -dinitrodiphenyl ether is dissolved;
(2) Adding a platinum-carbon catalyst with the platinum content of 3%, and introducing hydrogen; the flow is 8L/h; reacting for 2h at 80 ℃ under 0.4 MPA;
(3) Recovering the catalyst, adding 0.5kg of aromatic amine antioxidant triphenyl phosphite into the filtrate, replacing with hydrogen, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; 15kg of water; the temperature in the crystallization kettle is required to be reduced to 40-50 ℃ to finish dripping; adding 0.8kg of triphenyl phosphite serving as an aromatic amine antioxidant; filtering to obtain a crude product;
(4) The crude product is washed by methanol, centrifugally filtered and dried in vacuum.
Examples of the effects
The analyses of the products prepared in examples 1-3 and comparative examples 1, 2 are shown in Table 1:
| project | 4,4' -dinitrodiphenyl ether utilization/% | ODA yield/% | Color of ODA |
| Example 1 | 95.7 | 91.7 | Off-white color |
| Example 2 | 96.8 | 93.4 | Off-white color |
| Example 3 | 96.4 | 92.6 | Off-white color |
| Comparative example 1 | 96.1 | 89.7 | Blackish brown |
| Comparative example 2 | 96.3 | 85.4 | Light grey |
Claims (1)
1. The preparation method of the 4,4' -diaminodiphenyl ether is characterized in that the reaction environment does not contain oxygen and comprises the following steps:
(1) 11kg of DMF and 10kg of toluene are stirred uniformly, 26kg of 4,4 '-dinitrodiphenyl ether is added, and the temperature is raised to dissolve the 4,4' -dinitrodiphenyl ether, so as to obtain a mixed material;
(2) Adding platinum-carbon catalyst with 5% platinum content and N into the mixture 2 Introducing hydrogen after gas displacement, wherein the flow rate of the hydrogen is 9L/h, and reacting for 2h at 70 ℃ and 0.5MPa to obtain a reaction liquid, wherein no oxygen is generated when a catalyst is added for reaction;
(3) Filtering the reaction liquid to recover the catalyst, adding 1.2kg of aromatic amine antioxidant 5057 into the obtained filtrate, replacing with hydrogen, heating for dissolution, adding water for crystallization, wherein the water drop speed is 3-4 kg/min; the addition amount of water is 18kg; dropping is completed when the temperature in the crystallization kettle is reduced to 40-50 ℃; adding 0.6kg of aromatic amine antioxidant 5057; filtering to obtain a solid crude product, wherein no oxygen exists in the filtering process and no oxygen exists in the crystallization process;
(4) And washing the solid crude product by methanol, centrifugally filtering, and drying in vacuum to obtain the 4,4' -diaminodiphenyl ether.
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| CN202211630355.XA CN116082170A (en) | 2021-02-25 | 2021-02-25 | Preparation method of 4,4' -diaminodiphenyl ether |
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| CN202110210159.6A CN113087631A (en) | 2021-02-25 | 2021-02-25 | Preparation method of 4, 4' -diaminodiphenyl ether |
| CN202211630355.XA CN116082170A (en) | 2021-02-25 | 2021-02-25 | Preparation method of 4,4' -diaminodiphenyl ether |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539428A (en) * | 1982-05-10 | 1985-09-03 | Mallinckrodt, Inc. | Preparation of diaminodiphenyl ethers |
| CN102941096A (en) * | 2012-11-27 | 2013-02-27 | 江苏华伦化工有限公司 | Catalyst for preparing 4, 4'-diaminodiphenyl ether, preparation method and application of catalyst |
| CN106496047A (en) * | 2016-10-31 | 2017-03-15 | 南通汇顺化工有限公司 | The method that one kind prepares 4,4 ' diaminodiphenyl ethers |
| CN110639553A (en) * | 2019-10-21 | 2020-01-03 | 西安凯立新材料股份有限公司 | Iron-cobalt composite carbon-copper catalyst and method for continuously producing 4, 4-diaminodiphenyl ether |
| CN111072503A (en) * | 2019-12-28 | 2020-04-28 | 南通汇顺化工有限公司 | Method for preparing 3, 4' -diaminodiphenyl ether |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3192263A (en) * | 1960-08-18 | 1965-06-29 | Du Pont | Production of dinitrophenyl and diaminophenyl ethers |
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- 2021-02-25 CN CN202110210159.6A patent/CN113087631A/en active Pending
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539428A (en) * | 1982-05-10 | 1985-09-03 | Mallinckrodt, Inc. | Preparation of diaminodiphenyl ethers |
| CN102941096A (en) * | 2012-11-27 | 2013-02-27 | 江苏华伦化工有限公司 | Catalyst for preparing 4, 4'-diaminodiphenyl ether, preparation method and application of catalyst |
| CN106496047A (en) * | 2016-10-31 | 2017-03-15 | 南通汇顺化工有限公司 | The method that one kind prepares 4,4 ' diaminodiphenyl ethers |
| CN110639553A (en) * | 2019-10-21 | 2020-01-03 | 西安凯立新材料股份有限公司 | Iron-cobalt composite carbon-copper catalyst and method for continuously producing 4, 4-diaminodiphenyl ether |
| CN111072503A (en) * | 2019-12-28 | 2020-04-28 | 南通汇顺化工有限公司 | Method for preparing 3, 4' -diaminodiphenyl ether |
Non-Patent Citations (1)
| Title |
|---|
| 李广学, 马建华, 蔡春: "硝基苯加氢制备对氨基苯酚的工艺要素研究", 《应用化工》, vol. 33, no. 06, 30 December 2004 (2004-12-30), pages 21 - 24 * |
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