CN110172017A - A method of high-purity naphthalic acid is prepared by raw material of naphthalene - Google Patents
A method of high-purity naphthalic acid is prepared by raw material of naphthalene Download PDFInfo
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- CN110172017A CN110172017A CN201910449728.5A CN201910449728A CN110172017A CN 110172017 A CN110172017 A CN 110172017A CN 201910449728 A CN201910449728 A CN 201910449728A CN 110172017 A CN110172017 A CN 110172017A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
The invention discloses a kind of methods for preparing high-purity naphthalic acid as raw material using naphthalene comprising following steps: 1) alkylated reaction, and reaction kettle is added in naphthalene, an isopropyl naphthalene and catalyst, is passed through propylene heating and is reacted, obtains diisopropyl naphthalene；2) rectifying/Crystallization Separation obtains thick 2,6-DIPN by rectifying, then obtains high-purity 2,6-DIPN by method for crystallising；3) oxidation reaction, with Co-Mn-Br series catalysts, one kind or mixture of glacial acetic acid and propionic acid are solvent, and oxygen-containing gas aoxidizes diisopropyl naphthalene liquid phase synthesis 2,6-naphthalenedicarboxylic acid；4) it purifies, by step 3) gains through solid- liquid separation, washs, it is dry, obtain 2,6-naphthalenedicarboxylic acid solid powder.
Description
Technical field
The invention belongs to technical field of coal chemical industry, and in particular to a kind of side that high-purity naphthalic acid is prepared using naphthalene as raw material
Method.
Background technique
2,6- naphthalenedicarboxylic acid (2,6-NDCA) and its derivative are to prepare various polyester, polyurethane material and polymerizable mesogenic
The important monomer of object (LCP) etc..The poly- 2,6- (ethylene naphthalate) that especially 2,6-NDCA and glycol reaction obtain
(PEN), be it is better than ethylene glycol terephthalate (PET) rigidity, intensity is big, the superior high performance material of hot-working character.
By the difference of raw material, the method for industrialized production 2,6-naphthalenedicarboxylic acid can be divided into 2 classes: one kind is with benzene compounds
This is used for the Conventional processing methods of raw material, such as BP-Amoco, Mitsubishi chemical company, Chevron and Finland Optatech
Method, this method step is more, high production cost；Another kind of is the improvement process using naphthalene series compound as raw material, with naphthalene and methyl
Naphthalene is raw material, carries out the synthesis of 2,6-DMN, DMN product is made in a step, then can be obtained 2,6- through isomerization, separating-purifying
DMN, Exxon-Mobil company use this method, this method step is succinct, advantage of lower cost, have novelty.
Wherein industrialized route and route semi-industrial are as follows:
(1) ortho-xylene alkylation, cyclisation, dehydrogenation and isomerization produce 2,6- dimethylnaphthalene, reoxidize production naphthalene diformazan
Acid.Under sylvite catalyst action, at 142 DEG C of reaction temperature, ortho-xylene reacts production 2- amylene neighbour's first with 1,3-butadiene
Benzene；Using the LZY- zeolite of Pt-Cu as catalyst, at 163 DEG C of temperature and pressure 1.4MPa, 1,5- dimethyl tetrahydro naphthalene is produced；
In the presence of catalyst Pt-Re, under the conditions of 400 DEG C of reaction temperature and pressure 1.4MPa, 1,5- dimethylnaphthalene is obtained, in temperature
Under the conditions of 265 DEG C and pressure 0.7MPa, isomerization is carried out, 2,6- dimethylnaphthalene is obtained, through separating-purifying；It is again molten with acetic acid
Agent is bored using manganese acetate, acetic acid and ammonium bromide is catalyst, under 200 DEG C of reaction temperature and pressure 1.8MPa, dialkyl group naphthalene liquid phase
It aoxidizes and 2,6- naphthalenedicarboxylic acid is made.This reaction process is complicated, and synthetic route is long, and technical requirements are high, and reaction condition is harsher, always
Yield is 36% or so.
(2) naphthalene produces 2,6 diisopropyl naphthalenes through liquid-phase alkylation, reoxidizes 2,6-naphthalenedicarboxylic acid processed.It is handled by naphthalene in acid
The mordenite catalyst effect crossed is lower to react with propylene, and the method for the mixture rectifying of reaction obtains thick dialkyl group naphthalene (isomery
The mixture of body), using further isolated 2,6- dialkyl group naphthalene；2,6- dialkyl group naphthalene is in cobalt manganese bromine System Catalyst
In the presence of, using acetic acid as solvent, under 180-200 DEG C and 1-3MPa pressure condition, 2,6- naphthalene is made through air oxidation in liquid phase
Dioctyl phthalate.Such method reaction process step is more, and alkylation and purification are the key that the technologies, the countries such as current Japan, U.S.
Competitively carry out this work.Currently, the industrializing synthesis route of 2,6-NDCA mainly has two, first is that 2- methyl naphthalene acetylation
After obtain 2- methyl -6- acetyl group naphthalene, further oxidation be made 2,6-NDCA.Second is that 2,6- dialkyl group Fluidized bed 2,6-
NDCA, including 2,6- dimethylnaphthalene, 2,6- diethyl naphthalene, 2,6-DIPN liquid phase catalytic oxidation.Although the former has
Yield and selectivity are high, the relatively easy advantage of technique, but preparation 2- methyl -6- acetyl group naphthalene used catalyst is more expensive,
And be difficult to recycle, at high cost, reactant toxicity is big, pollution is big, therefore production scale is also smaller.And the alkylation that the latter passes through naphthalene
Afterwards, it using Co-Mn-Br catalyst system, using lower fatty acid as solvent, is reacted in titanium reactor, 200 DEG C of left sides of temperature
The right side, pressure 3.0MPa or so.Its reaction condition is mild, and easily controllable, and many researchers carry out more research to the technique.
Due to the more other dialkyl group naphthalenes of raw material 2,6- diisopropyl naphthalene (2,6-DIPN) be easier obtain and by many researchers'
Favor, becomes the hot spot of recent patent literature report.2,6- dialkyl group naphthalene (mainly 2,6- dimethylnaphthalene, 2,6- diethyl naphthalene
And 2,6-DIPN) oxidizing process preparation 2,6-NDCA, the catalyst system based on Co-Mn-Br is used, with carbon atom number
Lower aliphatic carboxylic acid for 2~6 is solvent, and liquid phase oxidation is carried out in titanium reactor.Reaction temperature is generally 200 DEG C of left sides
The right side, pressure are 1~3MPa.The great advantage of the reaction is at low cost, and reaction condition is milder, is suitble to large-scale industry metaplasia
It produces.Generally believe that 2,6- dialkyl group Fluidized bed method is most competitive at present.
Summary of the invention
The purpose of the present invention is to provide a kind of synthetic methods of naphthalenedicarboxylic acid, i.e., using naphthalene as raw material, through alkylation, essence
/ synthesis 2,6-naphthalenedicarboxylic acid the route such as Crystallization Separation, oxidation reaction is evaporated, industrial production can be reached.The present invention is with coal chemical industry
Product naphthalene be raw material, through processes such as alkylated reaction, rectifying/Crystallization Separation, oxidation reaction and purifications, in suitable operation item
Under part, the yield of 2,6-naphthalenedicarboxylic acid has reached 85%, and the last purity of product is up to 99.5%.Specific technical solution is as follows.
A method of high-purity naphthalic acid is prepared by raw material of naphthalene, comprising the following steps:
1) reaction kettle is added in naphthalene, an isopropyl naphthalene and catalyst by alkylated reaction, is passed through propylene heating and is reacted,
Obtain diisopropyl naphthalene；
2) rectifying/Crystallization Separation obtains thick 2,6-DIPN, then obtains height by method for crystallising by rectifying
Purity 2,6- diisopropyl naphthalene；
3) oxidation reaction, with Co-Mn-Br series catalysts, one kind or mixture of glacial acetic acid and propionic acid are solvent, oxygenous
Body aoxidizes diisopropyl naphthalene liquid phase synthesis 2,6- naphthalenedicarboxylic acid；
4) it purifies, by step 3) gains through solid- liquid separation, washs, it is dry, obtain 2,6-naphthalenedicarboxylic acid solid powder.
Due to there is 8 hydrogen atoms on naphthalene nucleus, they can be easily replaced alkyl group, and in traditional alkyl
The different types of reaction such as alkylation, isomerization, disproportionation occurs simultaneously under the conditions of change, is generating 2,6- diisopropyl naphthalene (2,6-
DIPN while), other isomers, single isopropyl naphthalene, three or tetra isopropyl naphthalene can also be generated.Therefore, it is necessary to select to close
Suitable catalyst improves the selectivity of reaction, increases by the content of 2,6-DIPN in product, common molecular sieve is urged in this patent
Agent has HZSM-5, H β, HM, HY etc., and resulting experimental result is as shown in table 1, and result can also be embodied in instances.
Further, catalyst described in step 1) includes HZSM-5, H β, HM or HY.
Further, 260 DEG C -300 DEG C of reaction temperature in step 1), reaction time 4-6 hour.
Further, it is reacted in the laggard rearrangement of step 1), 185 DEG C of reaction temperature, reaction time 1.5h.
The naphthalene isopropylation reaction result of 1 different catalysts of table compares
Rearrangement reaction
Thermodynamically more stable, 2,6-DIPN and 2, both 7-DIPN using α substitution products of β substitution product ratios
Can be by the mutual inversion of phases of intermolecular transalkylation, isopropyl group is reset by the transformation of alkyl, by dynamics
Product is converted into thermodynamic product.Therefore, purpose product 2, the content of 6-DIPN can be improved by rearrangement reaction.Rearrangement reaction
185 DEG C of temperature, reaction time 1.5h, experimental result is as shown in table 2.
Influence of 2 rearrangement reaction of table to 2,6-DIPN yield is improved
The yield of 2,6-DIPN significantly increases after rearrangement reaction, and product has occurred under conditions of rearrangement after alkylated reaction
The transfer of alkyl.Aromatic series is rearranged to intramolecular process, migrates base isopropyl as nucleopilic reagent and does electrophilic attack to naphthalene nucleus, to
Stable thermodynamic product 2 is generated, the direction of 6-DIPN is mobile, improves the content of 2,6-DIPN in product.
The separation of dialkyl group naphthalene is more difficult, cannot access high purity product using rectifying merely.The present invention passes through
Rectifying, then the methods of crystallization, recrystallization, washing separate the isomers of diisopropyl naphthalene.Specific method is reaction mixture
Thick diisopropyl naphthalene is obtained with the method for rectifying, then further isolated with the methods of rectifying-crystallisation, solvent crystallization
The 2,6-DIPN of high-purity.
Further, the step 2) Crystallization Separation the following steps are included:
A. product is cut into foreshot (solvent and naphthalene), single isopropyl naphthalene, diisopropyl naphthalene, polyisocyanate propyl through rectification under vacuum
Four part of naphthalene.
B. diisopropyl naphthalene obtains purity through One-step crystallization and is 83% 2,6-DIPN, then is obtained with ethyl alcohol recrystallization pure
The 2,6-DIPN that degree is 98%, yield is up to 85%.
Further, mother liquor selects modified NaY molecular sieve as 2,6-DIPN in One-step crystallization described in above-mentioned steps b
Adsorbent, toluene is desorbing agent, selectively comes out 2,6-DIPN adsorbing separation from mother liquor mixture.
Further, with continuous gas-liquid bubble stirring reactor, Co-Mn-Br series catalysts, with glacial acetic acid and third in step 3)
One or more mixtures of acid are solvent, and oxygen-containing gas aoxidizes diisopropyl naphthalene liquid phase synthesis 2,6-naphthalenedicarboxylic acid.Oxidation is anti-
It can should be carried out under the catalytic condition that one or more heavy metal catalysts form, preferably Co-Mn-Br homogeneous catalysis oxygen
Change, Co/Mn molar ratio is 1.2-4.0, and Br/Co molar ratio adds appropriate alkali metal (such as gold in 1.2-5 in catalyst system
Belong to sylvite or sodium salt) yield of 2,6-naphthalenedicarboxylic acid can be improved, additional amount is 1.6-4 times of Co+Mn molal quantity, wherein alkali metal
Object is closed for potassium or sodium compound or nickel metallization.Catalyst be CO-Mn-Br series catalysts, (Co+Mn) mole and diisopropyl
Base naphthalene mole is comparably 0.10-0.18.
Further, 160-200 DEG C of the temperature of oxidation reaction described in step 3), pressure 1.0-3.0MPa.
Further, it is washed described in step 4) first with glacial acetic acid, reusable heat distillation water washing.
Advantageous effect of the invention
Using naphthalene as raw material, through alkylation, oxidation reaction synthesizing naphthalic acid dimethyl ester technology, 2,6-naphthalenedicarboxylic acid purity
Height meets further esterification requirement.Using cheap naphthalene or alkylnaphthalene as raw material, abundance, reaction condition compares
Mildly, using isolation technics such as rectifying, crystallization, absorption to purpose product 2,6-DIPN carries out separation and purification, can directly obtain height
The 2,6- dialkyl group naphthalene of purity；It is solvent by catalyst, acetic acid and propionic acid of cobalt manganese, at 200 DEG C of temperature, the item of pressure 3.0MPa
It is more than 85% by the 2,6-naphthalenedicarboxylic acid yield of raw material of 2,6-DIPN under part, purity is greater than 98%, has met
Industrially to the requirement of 2,6- naphthalenedicarboxylic acid polymerization reaction.
Detailed description of the invention
Fig. 1 is the synthetic method flow chart of prior art 2,6- dimethylnaphthalene.
Fig. 2 is the preparation method flow chart of high-purity naphthalic acid of the present invention.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples.
According to the present invention, by the propylene alkylating reaction of naphthalene, 2,6- naphthalene diformazan is synthesized through rectifying Crystallization Separation, liquid phase oxidation
One specific embodiment of acid is using stirring bubbling reactor, a certain proportion of molecular sieve catalyst, hydro condition, naphthalane
Glycosylation reaction；Product after reaction is separated through rectifying column, separates an isopropyl naphthalene, diisopropyl naphthalene, triisopropyl naphthalene etc., wherein
The crystallized separation of diisopropyl naphthalene, recrystallization, obtains 98.5% or more 2,6-DIPN；Then by 2,6- diisopropyl
Naphthalene is added in gas-liquid agitation reactor, under the catalyst such as a certain proportion of cobalt acetate, manganese acetate, potassium bromide, potassium acetate, liquid
Phase oxidation reaction, product washs through solid- liquid separation, solid phase with glacial acetic acid, then after being washed with distilled water to remove soluble matter, Gu
Soma is dry to obtain 2,6- naphthalenedicarboxylic acid solid powder.
Embodiment 1:
150g naphthalene, mono- isopropyl naphthalene of 200g, 10g molecular sieve catalyst are added in reaction kettle, the sky in reaction kettle is excluded
Gas is warming up to 280 DEG C from hydrogen to 1.2MPa, starts to be passed through propylene, after reacting 4 hours, cools down, and filtering obtains liquid phase production
Product；Product is separated in rectifying column, then stirs decrease temperature crystalline with blender, and mother liquor is selecting modified NaY molecular sieve
As the adsorbent of 2,6-DIPN, toluene is desorbing agent, is selectively come out 2,6-DIPN adsorbing separation from mixture, most
2,6- diisopropyl naphthalene 75g is obtained eventually；2,6-DIPN is added in gas-liquid agitation bubbling reactor, is added simultaneously
260g glacial acetic acid, tetra- water cobalt acetate of 8g, tetra- water manganese acetate of 8.2g, 10.2g potassium bromide, 8.6g potassium acetate, agitating and heating are warming up to
180 DEG C, pressure 2.6MPa is passed through air oxidation, and 2,6-DIPN 75g is continuously supplied, and reaction stops after 3 hours
Reaction, cooling, reaction solution is through solid- liquid separation, and drying, obtains 62.2g khaki solid powder after being washed with glacial acetic acid and hot distilled water
End, the purity of 2,6-naphthalenedicarboxylic acid is 98.1% after liquid phase analysis.
Embodiment 2:
200g naphthalene, mono- isopropyl naphthalene of 200g, 20g molecular sieve catalyst are added in reaction kettle, the sky in reaction kettle is excluded
Gas is warming up to 260 DEG C from hydrogen to 1.0MPa, starts to be passed through propylene, after reacting 5 hours, cools down, and filtering obtains liquid phase production
Product；Product is separated in rectifying column, is stirred decrease temperature crystalline in blender, is obtained 2,6-DIPN 96g；By 2,6- bis-
Isopropyl naphthalene is added in gas-liquid agitation bubbling reactor, while 300g glacial acetic acid, tetra- water cobalt acetate of 10g, tetra- water of 9.6g is added
Manganese acetate, 14.2g potassium bromide, 10.8g potassium acetate, agitating and heating are warming up to 200 DEG C, and pressure 3.0MPa is passed through air oxygen
Change, 2,6-DIPN 44.67g is continuously supplied, stops reaction after reaction 3 hours, cooling, reaction solution is through solid-liquid point
From, it is dry after being washed with glacial acetic acid and hot distilled water, obtain 85.1g khaki solid powder, 2,6- naphthalenedicarboxylic acid after liquid phase analysis
Purity be 97.8%.
Embodiment 3:
300g naphthalene, mono- isopropyl naphthalene of 200g, 100g triisopropyl naphthalene, 40g molecular sieve catalyst are added in reaction kettle, row
Except the air in reaction kettle, from hydrogen to 2.0MPa, 300 DEG C are warming up to, starts to be passed through propylene, after reacting 6 hours, cooling,
Filtering, obtains liquid-phase product；Product is separated in rectifying column, is stirred decrease temperature crystalline in blender, is obtained 2,6- diisopropyl
Base naphthalene 134g；2,6-DIPN is added in gas-liquid agitation bubbling reactor, while 400g glacial acetic acid, 15g tetra- is added
Water cobalt acetate, tetra- water manganese acetate of 14g, 18g potassium bromide, 12g potassium acetate, agitating and heating are warming up to 200 DEG C, pressure 3.2MPa,
It is passed through air oxidation, 2,6-DIPN is continuously supplied, stops reaction after reaction 4 hours, cooling, reaction solution is through solid-liquid
Separation, it is dry after being washed with glacial acetic acid and hot distilled water, 102.1g khaki solid powder is obtained, 2,6- naphthalene diformazan after liquid phase analysis
The purity of acid is 98.3%.
Technical solution of the present invention is described in detail in above-described embodiment.It is apparent that the present invention is not limited being retouched
The embodiment stated.Based on the embodiments of the present invention, those skilled in the art can also make a variety of variations accordingly, but appoint
What is equal with the present invention or similar variation shall fall within the protection scope of the present invention.
Claims (10)
1. a kind of method for preparing high-purity naphthalic acid as raw material using naphthalene, which comprises the following steps:
1) reaction kettle is added in naphthalene, an isopropyl naphthalene and molecular sieve catalyst by alkylated reaction, is passed through propylene heating and is carried out instead
It answers, obtains diisopropyl naphthalene；
2) rectifying/Crystallization Separation obtains thick 2,6-DIPN, then obtains high-purity by method for crystallising by rectifying
2,6- diisopropyl naphthalene；
3) oxidation reaction, with Co-Mn-Br series catalysts, one kind or mixture of glacial acetic acid and propionic acid are solvent, oxygen-containing gas oxygen
Change diisopropyl naphthalene liquid phase synthesis 2,6- naphthalenedicarboxylic acid；
4) it purifies, by step 3) gains through solid- liquid separation, washs, it is dry, obtain 2,6-naphthalenedicarboxylic acid solid powder.
2. the method according to claim 1, wherein molecular sieve catalyst described in step 1) includes HZSM-
5, H β, HM or HY.
3. the method according to claim 1, wherein 260 DEG C -300 DEG C of reaction temperature, reaction time in step 1)
4-6 hours.
4. the method according to claim 1, wherein being reacted in the laggard rearrangement of step 1), reaction temperature 185
DEG C, reaction time 1.5h.
5. the method according to claim 1, wherein the step 2) Crystallization Separation the following steps are included:
A. product is cut into foreshot, single isopropyl naphthalene, diisopropyl naphthalene, four part of more isopropyl naphthalenes through rectification under vacuum；
B. diisopropyl naphthalene obtains purity through One-step crystallization as 83% 2,6-DIPN, then obtains purity with ethyl alcohol recrystallization and be
98% 2,6-DIPN, yield is up to 85%.
6. according to the method described in claim 5, it is characterized in that, in One-step crystallization described in step b mother liquor select it is modified
Adsorbent of the NaY molecular sieve as 2,6-DIPN, toluene are desorbing agent, selectively inhale 2,6-DIPN from mother liquor mixture
It is attached to separate.
7. the method according to claim 1, wherein Co/Mn in Co-Mn-Br series catalysts described in step 3)
Molar ratio is 1.2-4.0, and Br/Co molar ratio is 1.2-5, and (Co+Mn's) mole mole is comparably 0.10- with diisopropyl naphthalene
0.18。
8. the method according to claim 1, wherein also containing in Co-Mn-Br series catalysts described in step 3)
Sylvite or sodium salt or nickel metallization close object.
9. the method according to claim 1, wherein 160-200 DEG C of the temperature of oxidation reaction described in step 3),
Pressure 1.0-3.0MPa.
10. the method according to claim 1, wherein being washed described in step 4) first with glacial acetic acid, reusable heat steaming
Distilled water washing.
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Cited By (4)
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| CN112441909A (en) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | Synthesis method of 2,6-naphthalene dicarboxylic acid |
| CN113620799A (en) * | 2020-05-08 | 2021-11-09 | 中国石油化工股份有限公司 | Process for producing 2, 6-naphthalenedicarboxylic acid |
| CN113845414A (en) * | 2021-11-25 | 2021-12-28 | 中化学科学技术研究有限公司 | Method for synthesizing 2, 6-naphthalene dicarboxylic acid |
| CN115925531A (en) * | 2022-12-15 | 2023-04-07 | 沧州临港丰亚化工有限公司 | Method for preparing 2, 6-naphthalene dicarboxylic acid by using aromatic anhydride as raw material |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112441909A (en) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | Synthesis method of 2,6-naphthalene dicarboxylic acid |
| CN112441909B (en) * | 2019-09-04 | 2023-04-07 | 中国石油化工股份有限公司 | Method for synthesizing 2,6-naphthalene dicarboxylic acid |
| CN113620799A (en) * | 2020-05-08 | 2021-11-09 | 中国石油化工股份有限公司 | Process for producing 2, 6-naphthalenedicarboxylic acid |
| CN113620799B (en) * | 2020-05-08 | 2024-01-05 | 中国石油化工股份有限公司 | Process for preparing 2,6-naphthalene dicarboxylic acid |
| CN113845414A (en) * | 2021-11-25 | 2021-12-28 | 中化学科学技术研究有限公司 | Method for synthesizing 2, 6-naphthalene dicarboxylic acid |
| CN115925531A (en) * | 2022-12-15 | 2023-04-07 | 沧州临港丰亚化工有限公司 | Method for preparing 2, 6-naphthalene dicarboxylic acid by using aromatic anhydride as raw material |
| CN115925531B (en) * | 2022-12-15 | 2023-07-11 | 信诺立兴(沧州渤海新区)化工有限公司 | Method for preparing 2,6 naphthalene dicarboxylic acid by taking aromatic anhydride as raw material |
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