CN114539066A - Green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid - Google Patents
Green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid Download PDFInfo
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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 45
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000002194 synthesizing effect Effects 0.000 title claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 62
- 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 31
- 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
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 10
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000011968 lewis acid catalyst Substances 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 238000001308 synthesis method Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 3
- 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
- 238000001914 filtration Methods 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
- 239000000987 azo dye Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-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
- 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 1
- 150000004056 anthraquinones Chemical class 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
- 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
- 238000001256 steam distillation Methods 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 method for green and efficient synthesis of 2-benzoyl-3-nitrobenzoic acid belongs to the technical field of anthraquinone dye intermediate synthesis. The method comprises the steps of dissolving 3-nitrophthalic anhydride and benzene in FeCl3‑AlCl3The compound catalyst is used for catalyzing reflux reaction to prepare the 2-benzoyl-3-nitrobenzoic acid. Using FeCl3‑AlCl3Compared with the traditional single Lewis acid catalyst, the composite catalyst has higher catalytic efficiency. In addition, the method is simple to operate, safe, environment-friendly and economic, has high product yield and purity of over 98 percent, and is suitable for industrial production of the 2-benzoyl-3-nitrobenzoic acid.
Description
Technical Field
The invention relates to a method for green and efficient synthesis of 2-benzoyl-3-nitrobenzoic acid, and belongs to the technical field of synthesis of anthraquinone dye intermediates.
Background
Anthraquinone dyes are the second most synthetic dyes in the world except azo dyes, have better performance compared with azo dyes, and do not use aromatic amine carcinogenic compounds in the production process, so the anthraquinone 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 series dyes, has an increasing demand year by year, and is popular in domestic and foreign markets.
Currently, 2-benzoyl-3-nitrobenzoic acid is synthesized mainly by reacting 3-nitrobenzoic anhydride with phenylmagnesium bromide. Japanese Fuji film company (Japanese Fuji film company, Japanese patent laid-open No. 59, 137945 (1984)) has studied the synthesis of 2-benzoyl-3-nitrobenzoic acid as intermediate by nitration of phthalic anhydride to 3-nitrobenzoic anhydride, which is then reacted with phenyl magnesium bromide in carbon-based addition reaction.
In addition, the literature reports that 2-benzoyl-3-nitrobenzoic acid is synthesized 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 problems in the prior art, the invention aims to provide a method for synthesizing 2-benzoyl-3-nitrobenzoic acid in an environment-friendly and efficient manner.
The invention is realized by the following technical scheme:
a green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid comprises the following steps: mixing 3-nitrophthalic anhydride, benzene and FeCl3-AlCl3Mixing the composite catalysts, and heating to react to obtain the 2-benzoyl-3-nitrobenzoic acid, wherein the reaction formula is as follows:
the FeCl3-AlCl3The composite catalyst comprises FeCl3And AlCl3。
Specifically, the method comprises the following reaction steps: mixing 3-nitrophthalic anhydride, benzene and FeCl3-AlCl3Mixing the composite catalyst, and heating for reaction. After the reaction is finished, cooling to room temperature, adding an HCl aqueous solution into the system, heating to reflux, removing unreacted benzene by steam distillation, filtering out a reaction mixture while the reaction mixture is hot, and cooling and separating out a crude product of the 2-benzoyl-3-nitrobenzoic acid. Finally, the crude product is purified to obtain a pure product of the 2-benzoyl-3-nitrobenzoic acid。
The 3-nitrophthalic anhydride, benzene and FeCl mentioned in step (a)3-AlCl3The mol ratio of the composite catalyst is 1:3: 1.7-1.8.
FeCl described in step (ii)3-AlCl3The composite catalyst comprises FeCl3And AlCl3Preferably, FeCl3-AlCl3FeCl in composite catalyst3The mole fraction of (B) is 10-100%, and more preferably FeCl3-AlCl3FeCl in composite catalyst3Is 50% to 100%, most preferably FeCl3-AlCl3FeCl in composite catalyst3The mole fraction of (A) is 90-98%.
Further preferably: the specific reaction step is to mix dry FeCl3-AlCl3Adding the composite catalyst into dry benzene, heating and refluxing for 0.5h, and then slowly adding 3-nitrophthalic anhydride into the reaction system to start reaction until the reaction is finished.
More preferably: in the step, the heating reflux reaction temperature is 70-90 ℃, and the reaction time is 3-4 h.
Further preferably: the HCl aqueous solution in the step (1) is a 2.5% HCl solution in volume fraction.
Further preferred is: the purification step in the step is to dissolve the crude product of the 2-benzoyl-3-nitrobenzoic acid in an anhydrous sodium carbonate solution, filter and acidify the crude product by hydrochloric acid, and separate the crude product to obtain a 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 obtained reaction raw materials of 3-nitrophthalic anhydride and benzene, thereby reducing the production cost. (2) The method adopts FeCl3-AlCl3Compared with the traditional single Lewis acid catalyst, the composite catalyst has good selectivity and higher catalytic efficiency. (3) The method has the advantages of simple reaction conditions, convenient and safe operation, and environmental-friendly and economic 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-accessible principle, simple reaction conditions, and simultaneous productionThe yield and purity are high, and the method is suitable for the industrial production of the 2-benzoyl-3-nitrobenzoic acid.
Detailed Description
The reaction equation for synthesizing 2-benzoyl-3-nitrobenzoic acid is as follows:
example 1:
adding dry FeCl into a two-neck round-bottom flask in advance3(6.48 g, 0.04 mol), dried AlCl3(53.2 g, 0.40 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.44 mol, 1.7 eq, FeCl in it)3The molar fraction is 9 percent), dissolved in dry benzene (69 mL, 0.78 mol, 3 eq), heated to 80 ℃ and refluxed for 0.5h, then 3-nitrophthalic anhydride (50 g, 0.26mol, 1 eq) is slowly added under the condition of keeping the temperature, and the reaction is continued for 3h under stirring. After the reaction is finished, cooling to room temperature, adding an HCl aqueous solution (the volume fraction of HCl is 2.5%) which is equal to the volume of benzene into the reaction system, heating to reflux, distilling by using steam to remove unreacted benzene, filtering the reaction mixture while the reaction mixture is hot, and cooling and separating out the crude product of the 2-benzoyl-3-nitrobenzoic acid. Finally, the crude product was dissolved in anhydrous sodium carbonate solution, filtered and acidified with hydrochloric acid, and separated to give pure 2-benzoyl-3-nitrobenzoic acid (21.08g, 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 of methanol-waterV:V=3:2), and additionally 0.5% by mass of anhydrous Na each was added2SO4And 1.6% phosphoric acid; chromatographic column with octadecylsilane chemically bonded silica as filler (C18, 4.6X 250 mm, 5 μm); the detection wavelength is 254 nm; the flow rate is 1.0 mL/min; the column temperature is 30 ℃; test solution: about 50mg of sample was taken and taken into a 10mL volumetric flask, dissolved in methanol and diluted to the mark.
Example 2:
the synthesis method is as in example 1, except that FeCl is added3(14.27 g, 0.088 mol)，AlCl3(46.81 g, 0.352 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.44 mol, 1.7 eq, FeCl in it)3Molar fraction of 20%), to give pure 2-benzoyl-3-nitrobenzoic acid (24.57g, 35%) with a purity of 98.4% (HPLC).
Example 3:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(21.38g, 0.132 mol)，AlCl3(40.96 g, 0.308 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.44 mol, 1.7 eq, FeCl in it)3Mole fraction of 30%) to obtain pure 2-benzoyl-3-nitrobenzoic acid (25.27 g, 36%) with purity of 98.6% (HPLC).
Example 4:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(35.68g, 0.22 mol)，AlCl3(29.26 g, 0.22 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.44 mol, 1.7 eq, FeCl in it)3Mole fraction of 50%), and the final product was 98.3% (HPLC) pure 2-benzoyl-3-nitrobenzoic acid (32.30 g, 46%).
Example 5:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(37.26 g, 0.23 mol)，AlCl3(30.59 g, 0.23 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it3Mole fraction of 50%), and finally pure 2-benzoyl-3-nitrobenzoic acid (36.51 g, 52%) with a purity of 98.2% (HPLC).
Example 6:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(38.07g, 0.235 mol)，AlCl3(31.26 g, 0.235 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.47 mol, 1.8 eq, FeCl in it)3The mole fraction is 50 percent), and finally the pure 2-benzoyl-3-nitrobenzoic acid (33 g) is obtained47%) and 98.6% purity (HPLC).
Example 7:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(52.23 g, 0.322 mol)，AlCl3(18.35 g, 0.138 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it3Mole fraction of 70%), and the final product was 98.4% pure 2-benzoyl-3-nitrobenzoic acid (39.32 g, 56%).
Example 8:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(67.15 g, 0.414 mol)，AlCl3(6.12 g, 0.046 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it390% by mole fraction) to obtain pure 2-benzoyl-3-nitrobenzoic acid (49.14g, 70%) with a purity of 98.2% (HPLC).
Example 9:
the synthesis method is as in example 1, except that FeCl is added3(68.64 g, 0.423 mol)，AlCl3(4.92 g, 0.037 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it392% by mole fraction) to obtain pure 2-benzoyl-3-nitrobenzoic acid (50.55 g, 72%) with a purity of 98.3% (HPLC).
Example 10:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(70.13 g, 0.432 mol)，AlCl3(3.72 g, 0.028 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl among them394% mole fraction) to obtain pure 2-benzoyl-3-nitrobenzoic acid (52.66 g, 75%) with 98.4% purity (HPLC).
Example 11:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(70.88 g, 0.437 mol)，AlCl3(3.06 g, 0.023 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it395% mole fraction) to obtain pure 2-benzoyl-3-nitrobenzoic acid (53.36 g, 76%) with purity of 98.6% (HPLC).
Example 12:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(73.12g, 0.451 mol)，AlCl3(1.20 g, 0.009 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it398% by mole fraction) to obtain pure 2-benzoyl-3-nitrobenzoic acid (45.63 g, 65%) with a purity of 98.3% (HPLC).
Example 13:
the synthesis method is as in example 1, and differs from example 1 in that FeCl is contained therein3(73.87g, 0.455 mol)，AlCl3(0.665 g, 0.005 mol), FeCl obtained by mixing the two3-AlCl3Composite catalyst (0.46 mol, 1.75 eq, FeCl in it3Molar fraction 99%), and finally pure 2-benzoyl-3-nitrobenzoic acid (42.78 g, 61%) with a purity of 98.5% (HPLC).
Example 14:
adding dry FeCl into a two-neck round-bottom flask in advance3(74.61g, 0.46 mol, 1.75 eq) was dissolved in dry benzene (69 mL, 0.78 mol, 3 eq), heated to 80 ℃ and refluxed for 0.5h, then 3-nitrophthalic anhydride (50 g, 0.26mol, 1 eq) was added slowly under constant temperature, and the reaction was continued for 3h with stirring. After the reaction is finished, cooling to room temperature, adding an HCl aqueous solution (the volume fraction of HCl is 2.5%) which is equal to the volume of benzene into the reaction system, heating to reflux, distilling by using steam to remove unreacted benzene, filtering the reaction mixture while the reaction mixture is hot, and cooling and separating out the crude product of the 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 (39.28g, 56%) with a purity of 98.5% (HPLC).
The specific examples set forth 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 variations, modifications and substitutions may be made without departing from the spirit of the present invention, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. A green and efficient method for synthesizing 2-benzoyl-3-nitrobenzoic acid is characterized in that 3-nitrophthalic anhydride, benzene and FeCl are added3-AlCl3Mixing the composite catalysts, and heating to react to obtain the 2-benzoyl-3-nitrobenzoic acid, wherein the reaction formula is as follows:
the FeCl3-AlCl3The composite catalyst comprises FeCl3And AlCl3。
2. The method for green high-efficiency synthesis of 2-benzoyl-3-nitrobenzoic acid according to claim 1, wherein the 3-nitrophthalic anhydride, benzene, FeCl3-AlCl3The mol ratio of the composite catalyst is 1:3: 1.7-1.8.
3. The method for green high-efficiency synthesis of 2-benzoyl-3-nitrobenzoic acid according to claim 1, wherein the FeCl is3-AlCl3FeCl in composite catalyst3The mole fraction of (A) is 50% -100%.
4. The method for green high-efficiency synthesis of 2-benzoyl-3-nitrobenzoic acid according to claim 3, wherein the FeCl is3-AlCl3FeCl in composite catalyst3The mole fraction of (A) is 90-98%.
5. According to any one of claims 1 to 4The method for green and efficient synthesis of 2-benzoyl-3-nitrobenzoic acid is characterized in that dry FeCl is added3-AlCl3Adding the composite catalyst into dry benzene, heating and refluxing for 0.5h, adding 3-nitrophthalic anhydride, and continuing heating and reacting until the reaction is finished.
6. The method for green high-efficiency synthesis of 2-benzoyl-3-nitrobenzoic acid according to any one of claims 1 to 4, characterized in that the reaction temperature is 70-90 ℃.
7. The method for green high-efficiency synthesis of 2-benzoyl-3-nitrobenzoic acid according to any one of claims 1 to 4, characterized in that: the reaction time is 3-4 h.
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|---|---|---|---|---|
| US4500636A (en) * | 1983-01-27 | 1985-02-19 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
| CN1827587A (en) * | 2005-11-24 | 2006-09-06 | 东华大学 | Process for synthesizing 2-(4'-amino benzoyl) benzoic acid |
| CN106008187A (en) * | 2016-06-04 | 2016-10-12 | 江阴市长江化工有限公司 | Preparation method of synthetic anthraquinone |
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Patent Citations (3)
| 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 |
| CN1827587A (en) * | 2005-11-24 | 2006-09-06 | 东华大学 | Process for synthesizing 2-(4'-amino benzoyl) benzoic acid |
| CN106008187A (en) * | 2016-06-04 | 2016-10-12 | 江阴市长江化工有限公司 | Preparation method of synthetic anthraquinone |
Non-Patent Citations (4)
| Title |
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