CN114591279B - Synthesis method of 2, 3-naphthalene dianhydride - Google Patents
Synthesis method of 2, 3-naphthalene dianhydride Download PDFInfo
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- CN114591279B CN114591279B CN202210389386.4A CN202210389386A CN114591279B CN 114591279 B CN114591279 B CN 114591279B CN 202210389386 A CN202210389386 A CN 202210389386A CN 114591279 B CN114591279 B CN 114591279B
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- naphthalene dianhydride
- maleic anhydride
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- naphthalene
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- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000001308 synthesis method Methods 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005052 trichlorosilane Substances 0.000 claims abstract description 9
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 239000005049 silicon tetrachloride Substances 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 101150116295 CAT2 gene Proteins 0.000 description 3
- 101100392078 Caenorhabditis elegans cat-4 gene Proteins 0.000 description 3
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 3
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 3
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 3
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 3
- 101100005280 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-3 gene Proteins 0.000 description 3
- 101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 239000012847 fine chemical Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
-
- 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
Abstract
The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a synthesis method of 2, 3-naphthalene dianhydride, which takes phthalic dicarboxaldehyde and maleic anhydride as raw materials and synthesizes 2, 3-naphthalene dianhydride by one step, wherein the synthesis steps are as follows: adding an organic solvent, a catalyst, maleic anhydride, phthalic aldehyde and alkali into a reactor, reducing the temperature of the system to-60 to-20 ℃, dropwise adding trichlorosilane or silicon tetrachloride, reacting for 4-10 hours at-60 to-20 ℃, and then heating and refluxing for 5-30 hours to finish the reaction; after the reaction is finished, diatomite is used for filtering, the reaction liquid is concentrated, and then 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product. The synthesis method has the advantages of few reaction steps, no pollution, simplicity, high efficiency, low cost, high product yield and capability of realizing industrialized mass production.
Description
Technical Field
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a synthesis method of 2, 3-naphthalene dianhydride.
Background
Anhydrides are an important class of organic compounds. 2, 3-naphthalene dianhydride is also called 2, 3-naphthalene dicarboxylic anhydride and 2, 3-naphthalene dicarboxylic anhydride, is commonly used for synthesizing liquid crystal materials, medicines, dyes and the like, is an important intermediate for organic chemical industry and fine chemical industry, is also a curing agent for epoxy resin, and has very wide application.
There are few reports on the synthesis of 2, 3-naphthalene dianhydride. J.org.chem.1988,53,2353-2354, the synthesis of 2, 3-naphthalene dianhydride using acetal and maleic anhydride as starting materials is reported. The method is carried out in two steps, and concentrated sulfuric acid and acetic anhydride are needed in the second step. Although the total yield of the method is more than 85%, the reaction pollution is large, and dangerous goods concentrated sulfuric acid and easy drug acetic anhydride are used, so that the method is difficult to be used for mass production. In addition, CN106748752B also reports the synthesis of 2, 3-naphthalene dianhydride using a similar method, but the starting material is phthalic dicarboxaldehyde, which is synthesized through five steps of reactions.
J.am.chem.Soc.2017,139,4435-4442, reported a one-step synthesis of 2, 3-naphthalene dianhydride using maleic anhydride and α, α, α ', α' -tetrabromoo-xylene as raw materials, reacting for 4.5 hours at 70 ℃ under the action of sodium iodide, with a yield of 50%. The method has the defects of poor atom economy, low yield, environmental protection, high raw material cost and the like.
Organic letters 2011,13,3960-3963. Sc (OTf) is reported 3 The catalyst is prepared from phthalic aldehyde and maleic anhydride by one-step synthesis under the condition of triethylsilane. The method has simple steps, but the reaction yield is lower and only 40 percent.
The reported method has the defects of serious environmental pollution, long reaction steps, low yield and the like, and is difficult to realize industrialized mass production.
Disclosure of Invention
The invention aims at solving the technical problems existing in the prior art, and provides a method which has the advantages of few reaction steps, no pollution, easily available raw materials, low cost, high product yield and suitability for mass production of 2, 3-naphthalene dianhydride.
The technical scheme adopted by the invention is as follows:
a method for synthesizing 2, 3-naphthalene dianhydride takes phthalic aldehyde and maleic anhydride as raw materials, and synthesizes 2, 3-naphthalene dianhydride by one step, the synthesis steps are as follows: adding an organic solvent, a catalyst, maleic anhydride, phthalic aldehyde and alkali into a reactor, reducing the temperature of the system to-60 to-20 ℃, dropwise adding trichlorosilane or silicon tetrachloride, reacting for 4-10 hours at-60 to-20 ℃, and then heating and refluxing for 5-30 hours to finish the reaction; after the reaction is finished, filtering by using diatomite, concentrating the reaction solution, separating out 2, 3-naphthalene dianhydride, filtering, recrystallizing and drying to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product; the reaction general formula is as follows:
further, the organic solvent is anhydrous tetrahydrofuran, anhydrous dichloromethane, anhydrous toluene, anhydrous dioxane or anhydrous benzene.
Further, the mass ratio of the organic solvent to the maleic anhydride is 1.5-2.5:1.
Further, the catalyst is any one of a cat-1, a cat-2, a cat-3, a cat-4 and a cat-5, and the structural formulas of the cat-1, the cat-2, the cat-3, the cat-4 and the cat-5 are as follows:
further, the molar ratio of the catalyst to the maleic anhydride is 0.05-0.2:1.
Further, the base is triethylamine, dicyclohexylmethylamine, 4-dimethylaminopyridine or sodium carbonate.
Further, the molar ratio of the base to the maleic anhydride is 5-15:1.
Further, the molar ratio of the phthalic dicarboxaldehyde to the maleic anhydride is 1.5-4:1.
Further, the molar ratio of the trichlorosilane or the silicon tetrachloride to the maleic anhydride is 4-10:1.
Compared with the prior art, the invention has the beneficial effects that:
1. according to the invention, phthalic dicarboxaldehyde and maleic anhydride are used as raw materials, phosphorus oxide is used as a catalyst, alkali is used as an additive, and 2, 3-naphthalene dianhydride is synthesized in one step in an organic solvent under the action of trichlorosilane or silicon tetrachloride, so that the raw materials are easy to obtain, the cost is low, the reaction steps are few, and the method is pollution-free and suitable for mass production of 2, 3-naphthalene dianhydride.
2. The yield of the 2, 3-naphthalene dianhydride product synthesized by one step can reach 63-88%, the product yield is high, and the synthesis method is simple and efficient, can realize industrial production, and contributes to the large-scale production of the 2, 3-naphthalene dianhydride.
Detailed Description
The invention will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention.
Example 1
Adding anhydrous tetrahydrofuran (the mass ratio of the anhydrous tetrahydrofuran to the maleic anhydride is 1.5:1), cat-1 (0.05 mole), maleic anhydride (1 mole), phthalic dicarboxaldehyde (1.5 mole) and triethylamine (5 mole) into a reactor, reducing the temperature of the system to-40 ℃, dropwise adding silicon tetrachloride (4 mole), reacting for 4 hours at the temperature of-40 ℃, and heating and refluxing for 20 hours; after the reaction is finished, diatomite is used for filtering, the reaction solution is concentrated to a certain concentration, and then 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product, and the yield reaches 88 percent.
Example 2
In a reactor, anhydrous methylene dichloride (the mass ratio of the anhydrous methylene dichloride to maleic anhydride is 2:1), cat-2 (0.1 mol), maleic anhydride (1 mol), phthalic dicarboxaldehyde (2 mol) and dicyclohexylmethyl amine (6 mol) are added, the temperature of the system is reduced to minus 20 ℃, trichlorosilane (5 mol) is dropwise added, the reaction is carried out for 10 hours at minus 20 ℃, and the reaction is finished after heating and refluxing for 30 hours; after the reaction is finished, diatomite is used for filtering, the reaction solution is concentrated to a certain concentration, and then 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product, and the yield reaches 75 percent.
Example 3
In a reactor, anhydrous toluene (the mass ratio of the anhydrous toluene to maleic anhydride is 2.5:1), cat-3 (0.15 mol), maleic anhydride (1 mol), phthalic dicarboxaldehyde (3 mol) and sodium carbonate (15 mol) are added, the system temperature is reduced to minus 60 ℃, silicon tetrachloride (10 mol) is dropwise added, the reaction is carried out for 4 hours at minus 60 ℃, and the reaction is finished after heating and refluxing for 10 hours; after the reaction is finished, diatomite is used for filtering, the reaction solution is concentrated to a certain concentration, and then 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product, and the yield reaches 63%.
Example 4
In a reactor, anhydrous dioxane (the mass ratio of the anhydrous dioxane to the maleic anhydride is 2.2:1), cat-4 (0.2 mol), maleic anhydride (1 mol), phthalic dicarboxaldehyde (4 mol) and 4-dimethylaminopyridine (10 mol) are added, the system temperature is reduced to-50 ℃, trichlorosilane (8 mol) is dropwise added, the reaction is carried out for 5 hours at-50 ℃, and the reaction is finished after heating and refluxing for 8 hours; after the reaction is finished, diatomite is used for filtering, the reaction solution is concentrated to a certain concentration, and then 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product, and the yield reaches 85 percent.
Example 5
Adding anhydrous benzene (the mass ratio of the anhydrous benzene to the maleic anhydride is 1.8:1), cat-5 (0.07 mol), maleic anhydride (1 mol), phthalic dicarboxaldehyde (2.5 mol) and 4-dimethylaminopyridine (5 mol) into a reactor, reducing the temperature of the system to-25 ℃, dropwise adding trichlorosilane (5 mol), reacting for 4 hours at-25 ℃, and heating and refluxing for 5 hours; after the completion, the reaction solution is concentrated to a certain concentration by using diatomite for filtration, and then the 2, 3-naphthalene dianhydride is separated out, filtered, recrystallized and dried to obtain a pale yellow solid, wherein the yield reaches 63%.
According to the embodiment 1-5 of the invention, the yield of the 2, 3-naphthalene dianhydride product synthesized by one step can reach 63-88%, the product yield is high, the raw materials used by the method are easy to obtain, the raw material cost is low, the reaction steps are few, no pollution is caused, the synthesis method is concise and efficient, the method is suitable for mass production of 2, 3-naphthalene dianhydride, and industrial production can be realized.
Claims (8)
1. A method for synthesizing 2, 3-naphthalene dianhydride is characterized in that phthalic aldehyde and maleic anhydride are used as raw materials, and the 2, 3-naphthalene dianhydride is synthesized by one step, and the synthesis steps are as follows: adding an organic solvent, a catalyst, maleic anhydride, phthalic aldehyde and alkali into a reactor, reducing the temperature of the system to-60 to-20 ℃, dropwise adding trichlorosilane or silicon tetrachloride, reacting for 4-10 hours at-60 to-20 ℃, and then heating and refluxing for 5-30 hours to finish the reaction; after the reaction is finished, filtering by using diatomite, concentrating the reaction solution, separating out 2, 3-naphthalene dianhydride, filtering, recrystallizing and drying to obtain a light yellow solid, namely a 2, 3-naphthalene dianhydride product; the reaction general formula is as follows:
the catalyst is any one of a catalyst-1, a catalyst-2, a catalyst-3, a catalyst-4 and a catalyst-5, and the structural formulas of the catalyst-1, the catalyst-2, the catalyst-3, the catalyst-4 and the catalyst-5 are as follows:
2. the method for synthesizing 2, 3-naphthalene dianhydride according to claim 1, wherein the organic solvent is anhydrous tetrahydrofuran, anhydrous methylene chloride, anhydrous toluene, anhydrous dioxane or anhydrous benzene.
3. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 2, wherein the mass ratio of the organic solvent to maleic anhydride is 1.5-2.5:1.
4. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 1, wherein the molar ratio of the catalyst to maleic anhydride is 0.05 to 0.2:1.
5. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 1, wherein the base is triethylamine, dicyclohexylmethylamine, 4-dimethylaminopyridine or sodium carbonate.
6. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 5, wherein the molar ratio of the base to the maleic anhydride is 5 to 15:1.
7. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 1, wherein the molar ratio of phthalic aldehyde to maleic anhydride is 1.5-4:1.
8. The method for synthesizing 2, 3-naphthalene dianhydride according to claim 1, wherein the molar ratio of trichlorosilane or silicon tetrachloride to maleic anhydride is 4 to 10:1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS643180A (en) * | 1987-06-25 | 1989-01-06 | Nippon Steel Chem Co Ltd | Production of phthalic anhydride |
| CN106748752A (en) * | 2017-01-22 | 2017-05-31 | 河北凡克化工有限公司 | A kind of preparation method of 2,3 naphthalenedicarboxylic acid |
| CN108698984A (en) * | 2015-12-18 | 2018-10-23 | H·科斯特 | Novel bicyclic compounds as drug, particularly for treating Parkinson's disease |
-
2022
- 2022-04-13 CN CN202210389386.4A patent/CN114591279B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS643180A (en) * | 1987-06-25 | 1989-01-06 | Nippon Steel Chem Co Ltd | Production of phthalic anhydride |
| CN108698984A (en) * | 2015-12-18 | 2018-10-23 | H·科斯特 | Novel bicyclic compounds as drug, particularly for treating Parkinson's disease |
| CN106748752A (en) * | 2017-01-22 | 2017-05-31 | 河北凡克化工有限公司 | A kind of preparation method of 2,3 naphthalenedicarboxylic acid |
Non-Patent Citations (2)
| Title |
|---|
| Engaging Morita–Baylis–Hillman Reaction for the Generation of Isobenzofuran and the Consequent Entry into Highly Substituted Aromatic Systems;Vijay Nair et al.;Synthesis(第12期);1967-1970 * |
| Facile Sc(OTf)3-Catalyzed Generation and Successive Aromatization of Isobenzofuran from o-Dicarbonylbenzenes;Yuta Nishina et al.;Org. Lett.;第13卷(第15期);3960-3963 * |
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