CN106631821A - Method for preparing diaminonaphthalene - Google Patents
Method for preparing diaminonaphthalene Download PDFInfo
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- CN106631821A CN106631821A CN201610939448.9A CN201610939448A CN106631821A CN 106631821 A CN106631821 A CN 106631821A CN 201610939448 A CN201610939448 A CN 201610939448A CN 106631821 A CN106631821 A CN 106631821A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
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Abstract
The invention provides a method for preparing diaminonaphthalene. The method comprises the following steps: carrying out a nitration reaction by adopting sulfuric acid, fuming nitric acid and naphthalene so as to obtain mixed dinitronaphthalene; adding a second organic solvent, the mixed dinitronaphthalene, a catalyst and activated carbon into a reaction kettle, raising the temperature to 60-65 DEG C, adding hydrazine hydrate, and reacting and separating so as to obtain second filtrate and second filter cake; separating and purifying the second filtrate so as to obtain a solid, namely 1,8-diaminonaphthalene; and separating and purifying the second filter cake so as to obtain 1,5-diaminonaphthalene. According to the preparation of the mixed dinitronaphthalene, the nitratlon reaction is carried out by adopting an organic solvent free method, the waste acid can be recycled, and the yield and treatment cost of the three wastes can be reduced. The mixed dinitronaphthalene is directly reduced, the separation cost is reduced, and the market competitiveness is improved for industrial production. By utilizing different physical properties of the mixed dinitronaphthalene in different organic solvents, 1,8-diaminonaphthalene and 1,5-diaminonaphthalene with high purity are separated.
Description
Technical field
The invention belongs to pigment and dye field, are related to the intermediate of pigment and dyestuff, and in particular to a kind of diaminonaphthalene
Preparation method.
Background technology
1,8 1 diaminonaphthalenes are the important intermediates for manufacturing oil color, are mainly used in synthesis C.1. oil-soluble orange 60
Gas and oil dissolubility red 135 # etc., both pigment be widely used in the various materials such as PS, AS, ABS, MMA and hard PVC, PET
Color.Particularly black oil color, the such as successive exploitation of ball point pen ink in recent years, makes the demand of 1,8- diaminonaphthalenes
Increasingly increase.1,5-diaminonaphthalene and 1,8- diaminonaphthalene are two important compounds in diaminonaphthalene isomers, main to use
In the intermediate of dye (face) material, also can be used as resin and the raw material of agricultural chemicals.
The preparation of the mixed dinitronaphthalene of the intermediate of diaminonaphthalene, Chinese patent CN102827007A, CN102276475A,
Have a detailed description in the documents such as CN1194972A.But common problem is in course of reaction, using organic solvent dichloro
Methane, dichloroethanes etc., cause waste acidity recovery to apply mechanically difficulty, it is impossible to repeat to apply mechanically, and produce cost for wastewater treatment height, the three wastes
It is seriously polluted.
Dinitronaphthalene reduction at present prepares the method for diaminonaphthalene to be had：Iron powder reducing method, electrochemical reducing, hydro-reduction
Method and hydrazine hydrate reduction method etc..Chinese patent CN101187031A, CN101575295B, CN102020568A,
Have a detailed description in the documents such as CN98371188.1, CN94110239.4.Although gentle using iron powder reducing process conditions, work
Skill is simple, and side reaction is few, but separating catalyst is difficult, and three-waste pollution is serious, and yield is low, is gradually eliminated；Electrochemistry
Reducing process power consumption is big, at present using more only in laboratory synthesis and semi-industrial production.Catalytic hydrogenating reduction method can have
Effect reduces pollution, and the characteristics of with environmental friendliness, but catalytic hydrogenating reduction method is tight to equipment requirement, noble metal catalyst consumption
Greatly, product quality, yield are unstable.
Hydrazine hydrate reduction method reaction condition is gentle, the method processing ease, process is simple, in high yield, low stain, it is easy to real
Now industrialize.
For example in Chinese patent CN103664645A and CN101823968B documents describe in detail and disclose a kind of hydrazine hydrate
The method that 1,8- of reduction dinitronaphthalene prepares 1,8- diaminonaphthalenes, both the above method is required to separate mixed dinitronaphthalene
Purifying, separating mixed dinitronaphthalene increases product cost, does not play the advantage of hydrazine hydrate reduction method；The method is not suitable for industrialization system
Standby 1,8- diaminonaphthalenes and 1,5- diaminonaphthalenes.Therefore, mixed dinitronaphthalene is directly reduced, how to obtain respectively purity compared with
High 1,8- diaminonaphthalenes and 1,5- diaminonaphthalenes is the problem for needing to solve.
The content of the invention
Based on problems of the prior art, it is an object of the present invention to propose a kind of preparation side of diaminonaphthalene
Method, reduces production cost and is easy to industrialized production.
In order to solve above-mentioned technical problem, the application is adopted the following technical scheme that and is achieved：
A kind of preparation method of diaminonaphthalene, the method is comprised the following steps：
Step one, mixes the synthesis of dinitronaphthalene：
Sulfuric acid is added in reactor, stirring is opened, fuming nitric aicd is subsequently adding, naphthalene is added after being well mixed, after adding
Insulation 1 hour, then heating up carries out nitration reaction, is incubated 2～5 hours, terminates reaction, obtains the first reactant liquor；
First reactant liquor is down to into normal temperature, is filtered, obtain the first filtrate and the first filter cake, the first filtrate is reclaimed, the first filter
Cake is purified through washing with there is the first machine solvent to carry out beating, obtains mixed dinitronaphthalene；
Step 2, the synthesis of 1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
The second organic solvent, mixed dinitronaphthalene, catalyst and activated carbon are added in reactor, 60～65 DEG C are warming up to,
Hydrazine hydrate is added, rear back flow reaction is added 3～9 hours, stops reaction, obtain the second reactant liquor, the second reactant liquor is near often
Temperature, adds water, stirring, filters, and obtains the second filtrate and the second filter cake；
The separation and purification of step 3,1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
The second described filtrate stratification, point liquid, organic phase washing, organic phase temperature control≤100 DEG C are evaporated to nothing
Cut, obtains red brown solid, adds the first organic solvent beating purifying, the solid for obtaining to be 1.8- diaminonaphthalenes；
Described the second filter cake adds acetone, and at 20～30 DEG C 0.5h are reacted, and filters, and filtrate adds water concentration, addition first
Organic solvent beating purifying, the solid for obtaining is 1,5-diaminonaphthalene.
The present invention also has following distinguishing feature：
Specifically, described naphthalene, the mol ratio between sulfuric acid and nitric acid are 1：(4～6)：(2～4), i.e. naphthalene, mass concentration
It is 45 that sulfuric acid and mass concentration for 76% is the mass ratio between 98% fuming nitric aicd：(185.7～278.5)：(45.2～
90.4)。
Preferably, described naphthalene, the mass ratio between sulfuric acid and fuming nitric aicd are：Naphthalene：Mass concentration is 76% sulfuric acid：
Mass concentration is 98% fuming nitric aicd=45：246：56.5.
Specifically, in step one, the reaction temperature of nitration reaction is：Temperature before intensification is 15～30 DEG C, after intensification
Temperature is 70～75 DEG C.
Specifically, in step one, the first described organic solvent is dichloroethanes, methyl alcohol or toluene.
Specifically, in step 2, mixed mol ratio between dinitronaphthalene and hydrazine hydrate is：Mixed dinitronaphthalene：Hydrazine hydrate=
1：(3～5), that is, the mass ratio mixed between dinitronaphthalene and hydrazine hydrate that mass concentration is 80% is：Mixed dinitronaphthalene：Hydrazine hydrate
=60.8：(52.4～87.3),
Specifically, in step 2, described catalyst is ferric trichloride, is mixed between dinitronaphthalene, catalyst and activated carbon
Mass ratio be mixed dinitronaphthalene：Catalyst：Activated carbon=1：(1%～1.5%)：(10%～15%).
Preferably, in step 2, described catalyst is Iron(III) chloride hexahydrate, mixes dinitronaphthalene, catalyst, activated carbon
Mass ratio and hydrazine hydrate between is：Mixed dinitronaphthalene：Catalyst：Activated carbon：Mass concentration is 80% hydrazine hydrate=60.8：
0.61：6.1：61.5.
Specifically, in step 2, the second described organic solvent is in ethanol, dichloroethanes, methyl alcohol, toluene and acetone
More than one combination, the mass ratio between the second organic solvent and mixed dinitronaphthalene is 4：1.
Compared with prior art, beneficial has the technical effect that the present invention：
(I) mix the preparation of dinitronaphthalene carries out nitration reaction using the method for organic solvent-free, and spent acid can be recycled
Apply mechanically, reduce the yield and processing cost of the three wastes.
(II) mix dinitronaphthalene directly to be reduced, reduce separation costs, be that industrialized production improves market competition
Power.
(III) using mixed diaminonaphthalene in different organic solvents, different physical propertys；Isolate purity it is higher 1,
8- diaminonaphthalenes and 1,5-diaminonaphthalene.
Description of the drawings
Fig. 1 is the infared spectrum of 1,8- diaminonaphthalenes.
Fig. 2 is the nuclear magnetic spectrum of 1,8- diaminonaphthalenes.
Fig. 3 is the infared spectrum of 1,5-diaminonaphthalene.
Fig. 4 is the nuclear magnetic spectrum of 1,5-diaminonaphthalene.
The particular content of the present invention is described in more detail with reference to embodiments.
Specific embodiment
Defer to above-mentioned technical proposal, the specific embodiment of the present invention given below, it should be noted that the present invention not office
It is limited to specific examples below, all equivalents done on the basis of technical scheme each fall within the protection model of the present invention
Enclose.The present invention is described in further details with reference to embodiment.
Embodiment 1：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and the method is comprised the following steps：
Step one, mixes the synthesis of dinitronaphthalene：
Addition mass concentration is in agitator, thermometer, reflux condenser, the 500L reactors of high-order dropping tank
76% sulfuric acid 246kg, opens stirring, and keeping temperature is 15～30 DEG C, and the fuming nitric aicd that mass concentration is 98% is then added dropwise
56.5kg, 0.5h are dripped, and naphthalene 45kg is dividedly in some parts after being well mixed, and are added within 2 hours, and after adding 1 hour is incubated, and are then heated up
Nitration reaction is carried out to 70～75 DEG C, 3 hours are incubated, terminates reaction, obtain the first reactant liquor；
First reactant liquor is down to into normal temperature, is filtered, obtain the first filtrate and the first filter cake, the first filtrate is reclaimed, the first filter
Cake carries out beating and purifies through washing, crude product 200kg toluene, obtains the mixed dinitronaphthalene of 76kg；Product liquid chromatograph is analyzed
Purity >=98%.Yield：99.3% (weight in wet base, in terms of naphthalene).
Step 2, the synthesis of 1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
Toluene is added in agitator, thermometer, reflux condenser, the 1000L reactors of high-order dropping tank
242kg, methyl alcohol 62.0kg, stirring is lower to add mixed dinitronaphthalene 76kg (give money as a gift weight 60.8kg), Iron(III) chloride hexahydrate 0.61kg,
Activated carbon 6.1kg, is warming up to 60～65 DEG C, and addition is slowly added dropwise the hydrazine hydrate that 61.5kg mass concentrations are 80%, returns after adding
Stream reaction 5 hours, stops reaction, obtains the second reactant liquor, and the near normal temperature of the second reactant liquor adds water, and stirs, and filters, and obtains
Second filtrate and the second filter cake；
The separation and purification of step 3,1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
The second described filtrate stratification, point liquid, organic phase washing, organic phase temperature control≤100 DEG C are evaporated to nothing
Cut, obtains red brown solid 29.4kg.The beating of 147kg methyl alcohol is added, is stirred 0.5 hour；Under stirring condition, temperature control≤20 DEG C,
176kg water is gradually added into filtrate, 0 DEG C is cooled to, is filtered, baking material obtains product 24.0kg to constant weight, product gas-chromatography
Instrument purity assay=99.4%, yield：54.4% (in terms of mixed dinitronaphthalene).Fig. 1 is the infared spectrum of product, and Fig. 2 is product
Nuclear magnetic resonance map (hydrogen spectrum), from above-mentioned infrared and nuclear magnetic data it can be shown that the product obtained from the second filtrate is
1,8- diaminonaphthalene.
The second described filter cake adds 90kg acetone in 25 ± 5 DEG C, reacts 0.5h, filters, filtrate, plus 43kg water, and normal pressure is dense
Contracting, is cooled to 15 ± 5 DEG C, filters, and obtains solid 17.6kg.45kg toluene is beaten 1 hour, is down to 0 ± 2 DEG C, filters, and baking material is to perseverance
Weight, obtains product 13.8kg, product chromatographic purity >=99.3%, yield：31.2% (in terms of mixed dinitronaphthalene).
Fig. 3 is the infared spectrum of product, and Fig. 4 is the nuclear magnetic resonance map (hydrogen spectrum) of product, can be with table from above-mentioned infrared and nuclear magnetic data
Bright, the product obtained from the second filter cake is 1,5-diaminonaphthalene.
The total recovery of 1,8- diaminonaphthalene and 1,5-diaminonaphthalene is 85.6% (in terms of mixed dinitronaphthalene).
Embodiment 2：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：
The first organic solvent is replaced by methyl alcohol from toluene in the present embodiment.
In second organic solvent, ethanol is replaced by from methyl alcohol, from toluene dichloroethanes is replaced by.
Reflux time in step 2 is 9 hours.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.
In terms of mixed dinitronaphthalene, the yield of 1,8- diaminonaphthalene：53%, the yield of 1,5-diaminonaphthalene：32%, total recovery
For 85%.
Embodiment 3：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：
The first organic solvent is replaced by dichloroethanes from toluene in the present embodiment.
In second organic solvent, from methyl alcohol and toluene acetone is replaced by.
Reflux time in step 2 is 4 hours.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.
In terms of mixed dinitronaphthalene, the yield of 1,8- diaminonaphthalene：51%, the yield of 1,5-diaminonaphthalene：31%, total recovery
For 82%.
Embodiment 4：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：
It is mixed dinitronaphthalene to mix the mol ratio between dinitronaphthalene and hydrazine hydrate in the present embodiment in step 2：Hydrazine hydrate=
1：3, i.e. 52.4kg mass concentrations are 80% hydrazine hydrate.
Reflux time in step 2 is 9 hours.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.
In terms of mixed dinitronaphthalene, the yield of 1,8- diaminonaphthalene is 53.7%, and the yield of 1,5-diaminonaphthalene is 30.5%,
Total recovery is 84.2%.
Embodiment 5：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：
It is mixed dinitronaphthalene to mix the mol ratio between dinitronaphthalene and hydrazine hydrate in the present embodiment in step 2：Hydrazine hydrate=
1：5, i.e. 87.3kg mass concentrations are 80% hydrazine hydrate.
Reflux time in step 2 is 3 hours.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.
In terms of mixed dinitronaphthalene, the yield of 1,8- diaminonaphthalene is 54.4%, and the yield of 1,5-diaminonaphthalene is 31%, always
Yield is 85.5%.
Embodiment 6：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：Naphthalene in step one in the present embodiment：Mol ratio=1 of sulfuric acid：6, i.e. 278.5kg mass concentrations are 76% sulfuric acid.
In terms of naphthalene, the weight in wet base yield for mixing dinitronaphthalene is 99.0% to the product of step one.
Step 2 and step 3 are identical with the step of embodiment 1 two and step 3.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.Yield is also same as Example 1.
Embodiment 7：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：Naphthalene in step one in the present embodiment：Mol ratio=1 of sulfuric acid：4, i.e. 185.7kg mass concentrations are 76% sulfuric acid.
In terms of naphthalene, the weight in wet base yield for mixing dinitronaphthalene is 96.7% to the product of step one.
Step 2 and step 3 are identical with the step of embodiment 1 two and step 3.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.Yield is also same as Example 1.
Embodiment 8：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：Naphthalene in step one in the present embodiment：Mol ratio=1 of nitric acid：2, i.e. 45.2kg mass concentrations are 98% nitric acid.Step
In terms of naphthalene, the weight in wet base yield for mixing dinitronaphthalene is 90.0% to rapid one product.
Step 2 and step 3 are identical with the step of embodiment 1 two and step 3.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.Yield is also same as Example 1.
Embodiment 9：
The present embodiment provides a kind of preparation method of diaminonaphthalene, and other processes of the method are same as Example 1, and difference is only
It is only that：Naphthalene in step one in the present embodiment：Mol ratio=1 of nitric acid：4, i.e. 90.4kg mass concentrations are 98% nitric acid.Step
In terms of naphthalene, the weight in wet base yield for mixing dinitronaphthalene is 99.5% to rapid one product.
Step 2 and step 3 are identical with the step of embodiment 1 two and step 3.
The characterization result of 1,8- diaminonaphthalene is same as Example 1, characterization result and the phase of embodiment 1 of 1,5-diaminonaphthalene
Together.Yield is also same as Example 1.
Claims (9)
1. a kind of preparation method of diaminonaphthalene, it is characterised in that the method is comprised the following steps：
Step one, mixes the synthesis of dinitronaphthalene：
Sulfuric acid is added in reactor, stirring is opened, fuming nitric aicd is subsequently adding, naphthalene is added after being well mixed, 1 is incubated after adding
Hour, then heating up carries out nitration reaction, is incubated 2～5 hours, terminates reaction, obtains the first reactant liquor；
First reactant liquor is down to into normal temperature, is filtered, obtain the first filtrate and the first filter cake, the first filtrate is reclaimed, the first filter cake Jing
Washing is crossed, is purified with there is the first machine solvent to carry out beating, obtain mixed dinitronaphthalene；
Step 2, the synthesis of 1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
The second organic solvent, mixed dinitronaphthalene, catalyst and activated carbon are added in reactor, 60～65 DEG C are warming up to, is added
Hydrazine hydrate, adds rear back flow reaction 3～9 hours, stops reaction, obtains the second reactant liquor, by the near normal temperature of the second reactant liquor, plus
Water, stirring is filtered, and obtains the second filtrate and the second filter cake；
The separation and purification of step 3,1,8- diaminonaphthalene and 1,5-diaminonaphthalene：
The second described filtrate stratification, point liquid, organic phase washing, organic phase temperature control≤100 DEG C are evaporated to without cut,
Red brown solid is obtained, adds the first organic solvent beating purifying, the solid for obtaining to be 1.8- diaminonaphthalenes；
Described the second filter cake adds acetone, reacts 0.5 hour at 20～30 DEG C, filters, and filtrate adds water concentration, and addition first has
Machine solvent beating purifying, the solid for obtaining is 1,5-diaminonaphthalene.
2. the preparation method of diaminonaphthalene as claimed in claim 1, it is characterised in that described naphthalene, between sulfuric acid and nitric acid
Mol ratio be 1：(4～6)：(2～4).
3. the preparation method of diaminonaphthalene as claimed in claim 2, it is characterised in that described naphthalene, sulfuric acid and fuming nitric aicd
Between mass ratio be：Naphthalene：Mass concentration is 76% sulfuric acid：Mass concentration is 98% fuming nitric aicd=45：246：56.5.
4. the preparation method of diaminonaphthalene as claimed in claim 1, it is characterised in that in step one, the reaction of nitration reaction
Temperature is：Temperature before intensification is 15～30 DEG C, and the temperature after intensification is 70～75 DEG C.
5. the preparation method of diaminonaphthalene as claimed in claim 1, it is characterised in that in step one, described first is organic
Solvent is dichloroethanes, methyl alcohol or toluene.
6. the preparation method of diaminonaphthalene as claimed in claim 1, it is characterised in that in step 2, mixes dinitronaphthalene and water
Close hydrazine between mol ratio be：Mixed dinitronaphthalene：Hydrazine hydrate=1：(3～5).
7. the preparation method of diaminonaphthalene as claimed in claim 6, it is characterised in that in step 2, described catalyst is
Ferric trichloride, it is mixed dinitronaphthalene to mix the mass ratio between dinitronaphthalene, catalyst and activated carbon：Catalyst：Activated carbon=1：
(1%～1.5%)：(10%～15%).
8. the preparation method of diaminonaphthalene as claimed in claims 6 or 7, it is characterised in that in step 2, described catalyst
For Iron(III) chloride hexahydrate, mixed mass ratio between dinitronaphthalene, catalyst, activated carbon and hydrazine hydrate is：Mixed dinitronaphthalene：Urge
Agent：Activated carbon：Mass concentration is 80% hydrazine hydrate=60.8：0.61：6.1：61.5.
9. the preparation method of diaminonaphthalene as claimed in claim 1, it is characterised in that in step 2, described second is organic
Solvent is the combination of one or more of ethanol, dichloroethanes, methyl alcohol, toluene and acetone, the second organic solvent and mixed dinitro
Mass ratio between naphthalene is 4：1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110156991A (en) * | 2019-06-10 | 2019-08-23 | 宜宾天原集团股份有限公司 | A kind of preparation method of low thermal expansion coefficient polyimide |
| CN110683957A (en) * | 2019-10-25 | 2020-01-14 | 湖南比德生化科技股份有限公司 | Method for synthesizing, separating and purifying diaminonaphthalene |
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| CN110156991A (en) * | 2019-06-10 | 2019-08-23 | 宜宾天原集团股份有限公司 | A kind of preparation method of low thermal expansion coefficient polyimide |
| CN110683957A (en) * | 2019-10-25 | 2020-01-14 | 湖南比德生化科技股份有限公司 | Method for synthesizing, separating and purifying diaminonaphthalene |
| CN110683957B (en) * | 2019-10-25 | 2022-10-28 | 湖南比德生化科技股份有限公司 | Method for synthesizing, separating and purifying diaminonaphthalene |
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