CN114539066B - Method for synthesizing 2-benzoyl-3-nitrobenzoic acid - Google Patents
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- VQCAQTNPROLAJK-UHFFFAOYSA-N 2-benzoyl-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 VQCAQTNPROLAJK-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 239000002131 composite material Substances 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000011968 lewis acid catalyst Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000001308 synthesis method Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WTPAXIMTWYTETA-UHFFFAOYSA-N (3-nitrobenzoyl) 3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)OC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 WTPAXIMTWYTETA-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C201/16—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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid belongs to the technical field of anthraquinone dye intermediate synthesis. The method prepares the 2-benzoyl-3-nitrobenzoic acid by the catalytic reflux reaction of 3-nitrophthalic anhydride and benzene in FeCl 3-AlCl3 composite catalyst. Compared with the traditional single Lewis acid catalyst, the FeCl 3-AlCl3 composite catalyst has higher catalytic efficiency. In addition, the method is simple and safe to operate, environment-friendly and economic, has high product yield and purity of more than 98%, and is suitable for industrial production of 2-benzoyl-3-nitrobenzoic acid.
Description
Technical Field
The invention relates to a green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid, belonging to the technical field of anthraquinone dye intermediate synthesis.
Background
Anthraquinone series dyes are the second largest synthetic dyes in the world except azo dyes, have better performance than azo dyes and do not use aromatic amine carcinogenic compounds in the production process, so the anthraquinone series dyes are widely applied. The 2-benzoyl-3-nitrobenzoic acid is widely applied to the fields of dyes, medicines, pesticides, other fine chemicals and the like, is used as an important intermediate for producing anthraquinone dyes, has increased demand year by year and is popular in both domestic and foreign markets.
At present, 2-benzoyl-3-nitrobenzoic acid is synthesized by reacting 3-nitroanhydride with phenylmagnesium bromide. Japanese Fuji film Co (Japanese Fuji film Co., japanese patent application laid-open No. 59, 137945 (1984)) has studied to produce 3-nitroaniline from phthalic anhydride by nitration and then by carbon-based addition reaction with phenylmagnesium bromide to synthesize intermediate 2-benzoyl-3-nitrobenzoic acid.
In addition, there are reports of synthesizing 2-benzoyl-3-nitrobenzoic acid by 3-nitrobenzoic anhydride and benzene under the catalysis of Lewis acid, but the method has the problems of poor reaction selectivity and low yield.
Disclosure of Invention
Aiming at the defects and the problems in the prior art, the invention aims to provide a green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid.
The invention is realized by the following technical scheme:
A green method for efficiently synthesizing 2-benzoyl-3-nitrobenzoic acid comprises the following steps: mixing 3-nitrophthalic anhydride, benzene and FeCl 3-AlCl3 composite catalyst, heating and reacting to obtain 2-benzoyl-3-nitrobenzoic acid, wherein the reaction formula is as follows:
；
The FeCl 3-AlCl3 composite catalyst comprises FeCl 3 and AlCl 3.
Specifically, the reaction steps of the method are as follows: mixing 3-nitrophthalic anhydride, benzene and FeCl 3-AlCl3 composite catalyst, heating and reacting. After the reaction is finished, cooling to room temperature, adding HCl aqueous solution into the system, heating to reflux, distilling with water vapor to remove unreacted benzene, filtering out the reaction mixture while the reaction mixture is hot, and cooling to separate out a crude product of 2-benzoyl-3-nitrobenzoic acid. And finally, purifying the crude product to obtain a pure 2-benzoyl-3-nitrobenzoic acid product.
The molar ratio of the 3-nitrophthalic anhydride to the benzene to the FeCl 3-AlCl3 composite catalyst in the step is 1:3:1.7-1.8.
The FeCl 3-AlCl3 composite catalyst in the step comprises FeCl 3 and AlCl 3, preferably, the mole fraction of FeCl 3 in the FeCl 3-AlCl3 composite catalyst is 10% -100%, more preferably, the mole fraction of FeCl 3 in the FeCl 3-AlCl3 composite catalyst is 50% -100%, and most preferably, the mole fraction of FeCl 3 in the FeCl 3-AlCl3 composite catalyst is 90% -98%.
Further preferred is: the specific reaction steps are that the dried FeCl 3-AlCl3 composite catalyst is added into dried benzene, heated and refluxed for 0.5h, and then 3-nitrophthalic anhydride is slowly added into the reaction system to start the reaction until the reaction is finished.
Further preferred are: the heating reflux reaction temperature in the step is 70-90 ℃ and the reaction time is 3-4h.
Further preferred is: the aqueous HCl solution in the step is 2.5% HCl solution in volume fraction.
Further preferred is: the purification step is to dissolve the crude product of the 2-benzoyl-3-nitrobenzoic acid in anhydrous sodium carbonate solution, filter and acidify the solution by hydrochloric acid, and separate the solution to obtain the pure product of the 2-benzoyl-3-nitrobenzoic acid.
Compared with the prior art, the invention has the following remarkable advantages: (1) The method adopts two cheap and easily available reaction raw materials of 3-nitrophthalic anhydride and benzene, thereby reducing the production cost. (2) Compared with the traditional single Lewis acid catalyst, the method adopts the FeCl 3-AlCl3 composite catalyst, and has good selectivity and higher catalytic efficiency. (3) The method has the advantages of simple reaction conditions, convenient and safe operation, and environment-friendly and economical post-treatment mode. (4) The 2-benzoyl-3-nitrobenzoic acid synthesized by the method has high yield and purity of more than 98 percent. (5) The method has the advantages of easily obtained principle, simple reaction condition, and high product yield and purity, and is suitable for industrial production of 2-benzoyl-3-nitrobenzoic acid.
Detailed Description
The reaction equation for synthesizing 2-benzoyl-3-nitrobenzoic acid is as follows:
example 1:
Dried FeCl 3 (6.48 g, 0.04 mol), dried AlCl 3 (53.2 g, 0.40 mol) and a FeCl 3-AlCl3 composite catalyst (0.44 mol, 1.7 eq, wherein the mole fraction of FeCl 3 is 9%) mixed with the mixture, dissolved in dried benzene (69 mL, 0.78 mol, 3 eq), heated to 80 ℃ and refluxed for 0.5h, and then 3-nitrophthalic anhydride (50 g,0.26 mol, 1 eq) was slowly added under the condition of keeping the temperature, and the reaction was continued with stirring for 3h. After the reaction, cooling to room temperature, adding HCl aqueous solution (volume fraction of HCl is 2.5%) with the same volume as benzene into the reaction system, heating to reflux, distilling with water vapor to remove unreacted benzene, filtering out the reaction mixture while the reaction mixture is hot, and cooling to separate out a crude product of 2-benzoyl-3-nitrobenzoic acid. Finally, the crude product was dissolved in anhydrous sodium carbonate solution, filtered and acidified with hydrochloric acid, and isolated to give pure 2-benzoyl-3-nitrobenzoic acid (21.08 g, 30%) with a purity of 98.5% (HPLC).
The liquid phase detection method of the 2-benzoyl-3-nitrobenzoic acid comprises the following steps: mobile phase methanol-water (V: v=3:2), and anhydrous Na 2SO4 and phosphoric acid 1.6% by mass respectively were added; chromatography column octadecylsilane chemically bonded silica as filler (C18, 4.6X1250 mm,5 μm); the detection wavelength is 254 nm; the flow rate is 1.0 mL/min; column temperature is 30 ℃; test solution: samples were taken at approximately 50mg into 10mL volumetric flasks, dissolved in methanol and diluted to scale.
Example 2:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(14.27 g, 0.088 mol),AlCl3 (46.81 g, 0.352, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.44, mol, 1.7, eq, wherein FeCl 3 was 20% by mole fraction) and the pure 2-benzoyl-3-nitrobenzoic acid (24.57 g, 35%) was obtained in a purity of 98.4% (HPLC).
Example 3:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(21.38g, 0.132 mol),AlCl3 (40.96 g, 0.308 mol) was used as a mixed FeCl 3-AlCl3 composite catalyst (0.44 mol, 1.7 eq, wherein the molar fraction of FeCl 3 was 30%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (25.27 g, 36%) with a purity of 98.6% (HPLC).
Example 4:
the synthesis method was conducted in accordance with example 1, except that FeCl 3(35.68g, 0.22 mol),AlCl3 (29.26 g, 0.22, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.44, mol, 1.7, eq, wherein the molar fraction of FeCl 3 was 50%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (32.30, g, 46%) with a purity of 98.3% (HPLC).
Example 5:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(37.26 g, 0.23 mol),AlCl3 (30.59 g, 0.23, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46, mol, 1.75, eq, wherein the molar fraction of FeCl 3 was 50%) as a mixture, and the pure 2-benzoyl-3-nitrobenzoic acid (36.51 g, 52%) was obtained in a purity of 98.2% (HPLC).
Example 6:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(38.07g, 0.235 mol),AlCl3 (31.26 g, 0.235, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.47, mol, 1.8, eq) in which FeCl 3 was 50% by mole fraction to obtain pure 2-benzoyl-3-nitrobenzoic acid (33, g, 47%) with a purity of 98.6% (HPLC).
Example 7:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(52.23 g, 0.322 mol),AlCl3 (18.35 g, 0.138 mol) was used as a mixed FeCl 3-AlCl3 composite catalyst (0.46 mol, 1.75 eq, wherein the molar fraction of FeCl 3 was 70%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (39.32 g, 56%) with a purity of 98.4% (HPLC).
Example 8:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(67.15 g, 0.414 mol),AlCl3 (6.12, g, 0.046, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46, mol, 1.75, eq, wherein the molar fraction of FeCl 3 was 90%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (49.14 g, 70%) with a purity of 98.2% (HPLC).
Example 9:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(68.64 g, 0.423 mol),AlCl3 (4.92 g, 0.037, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46, mol, 1.75, eq, wherein the mole fraction of FeCl 3 was 92%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (50.55, g, 72%) with a purity of 98.3% (HPLC).
Example 10:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(70.13 g, 0.432 mol),AlCl3 (3.72, g, 0.028, mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46, mol, 1.75, eq, wherein the molar fraction of FeCl 3 was 94%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (52.66, g, 75%) with a purity of 98.4% (HPLC).
Example 11:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(70.88 g, 0.437 mol),AlCl3 (3.06 g, 0.023, 0.023 mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46, 0.46 mol, 1.75, 1.75 eq, wherein the molar fraction of FeCl 3 was 95%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (53.36 g, 76%) with a purity of 98.6% (HPLC).
Example 12:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(73.12g, 0.451 mol),AlCl3 (1.20 g, 0.009 mol) was used as the FeCl 3-AlCl3 composite catalyst (0.46 mol, 1.75 eq, wherein the molar fraction of FeCl 3 was 98%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (45.63 g, 65%) with a purity of 98.3% (HPLC).
Example 13:
The synthesis method was conducted in accordance with example 1, except that FeCl 3(73.87g, 0.455 mol),AlCl3 (0.665 g, 0.005 mol) was used as a FeCl 3-AlCl3 composite catalyst (0.46 mol, 1.75 eq, wherein the molar fraction of FeCl 3 was 99%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (42.78 g, 61%) with a purity of 98.5% (HPLC).
Example 14:
Dried FeCl 3 (74.61 g, 0.46 mol, 1.75 eq) was added in advance to a two-necked round bottom flask, dissolved in dried benzene (69 mL, 0.78 mol, 3 eq), heated to 80 ℃ for reflux for 0.5h, then 3-nitrophthalic anhydride (50 g, 0.26mol, 1 eq) was slowly added under heat-preserving conditions, and stirring was continued for 3h. After the reaction, cooling to room temperature, adding HCl aqueous solution (volume fraction of HCl is 2.5%) with the same volume as benzene into the reaction system, heating to reflux, distilling with water vapor to remove unreacted benzene, filtering out the reaction mixture while the reaction mixture is hot, and cooling to separate out a crude product of 2-benzoyl-3-nitrobenzoic acid. Finally, the crude product was dissolved in anhydrous sodium carbonate solution, filtered and acidified with hydrochloric acid, and isolated to give pure 2-benzoyl-3-nitrobenzoic acid (39.28 g, 56%) with a purity of 98.5% (HPLC).
The specific examples described above illustrate only preferred embodiments of the invention and are not intended to limit the scope of the invention. It should be noted that any modifications, improvements and substitutions made without departing from the spirit of the invention are within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the claims appended hereto.
Claims (4)
1. A method for synthesizing 2-benzoyl-3-nitrobenzoic acid is characterized in that 3-nitrophthalic anhydride, benzene and FeCl 3-AlCl3 composite catalyst are mixed and heated for reaction to obtain 2-benzoyl-3-nitrobenzoic acid, and the reaction formula is as follows:
；
The FeCl 3-AlCl3 composite catalyst comprises FeCl 3 and AlCl 3;
the mole fraction of FeCl 3 in the FeCl 3-AlCl3 composite catalyst is 90% -95%;
The molar ratio of the 3-nitrophthalic anhydride, benzene and FeCl 3-AlCl3 composite catalyst is 1:3:1.7-1.8.
2. The method for synthesizing 2-benzoyl-3-nitrobenzoic acid according to claim 1, wherein the dried FeCl 3-AlCl3 composite catalyst is added into dried benzene, after heating and refluxing for 0.5 h, 3-nitrophthalic anhydride is added, and the heating reaction is continued until the reaction is finished.
3. The method for synthesizing 2-benzoyl-3-nitrobenzoic acid according to claim 1, wherein the reaction temperature is 70-90 ℃.
4. A method for synthesizing 2-benzoyl-3-nitrobenzoic acid according to claim 1, characterized in that: the reaction time is 3-4 hours.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4500636A (en) * | 1983-01-27 | 1985-02-19 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
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| CN100387571C (en) * | 2005-11-24 | 2008-05-14 | 东华大学 | A kind of synthetic method of 2-(4'-aminobenzoyl) benzoic acid |
| CN106008187B (en) * | 2016-06-04 | 2018-08-28 | 江阴市长江化工有限公司 | A kind of preparation method of synthesis anthraquinone |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4500636A (en) * | 1983-01-27 | 1985-02-19 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
Non-Patent Citations (1)
| Title |
|---|
| Lawrence, Walter A.，等.Fridel and Crafts' reaction-nitrophthalic anhydrides and acetylaminophthalic anhydrides with benzene and aluminium chloride.《Journal of the American Chemical Society》.1920,第42卷1871-9，1874页倒数第2段-1875页第1段. * |
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