CN115947311A - Hydrogen peroxide working solution solvent system - Google Patents
Hydrogen peroxide working solution solvent system Download PDFInfo
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- CN115947311A CN115947311A CN202111176361.8A CN202111176361A CN115947311A CN 115947311 A CN115947311 A CN 115947311A CN 202111176361 A CN202111176361 A CN 202111176361A CN 115947311 A CN115947311 A CN 115947311A
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- imide derivative
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- 239000012224 working solution Substances 0.000 title claims abstract description 84
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 239000002904 solvent Substances 0.000 title claims abstract description 38
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 33
- 150000003949 imides Chemical class 0.000 claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 12
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 64
- 238000005984 hydrogenation reaction Methods 0.000 claims description 48
- 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 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 150000004056 anthraquinones Chemical class 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 15
- 239000012024 dehydrating agents Substances 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 20
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- -1 -tert-butyl imide Chemical class 0.000 description 5
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- VSURRQZMKWVYIC-UHFFFAOYSA-N n-ethyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(CC)C(=O)C1=CC=CC=C1 VSURRQZMKWVYIC-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- MAKLMMYWGTWPQM-UHFFFAOYSA-N 2-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCC)=CC=C3C(=O)C2=C1 MAKLMMYWGTWPQM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-LZFNBGRKSA-N Potassium-45 Chemical compound [45K] ZLMJMSJWJFRBEC-LZFNBGRKSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a hydrogen peroxide working solution solvent system, which comprises the following components: the aromatic hydrocarbon, the imide derivative A and the diisobutyl carbinol are counted by volume parts, the aromatic hydrocarbon is 30 to 95 parts, preferably 60 to 85 parts, the imide derivative A is 2 to 30 parts, and the diisobutyl carbinol is 2 to 20 parts. The solvent system has good dissolving capacity for 2-alkylanthraquinone, especially hydroanthraquinone, the physical and chemical properties of the working liquid are stable, the density and the viscosity are low, the operation efficiency of a hydrogen peroxide device can be greatly improved, a high-quality and high-concentration hydrogen peroxide product can be directly produced, the safety and the reliability of the production process can be improved, the asset investment and the production operation cost are reduced, and the solvent system has good industrial application prospect.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a working solution solvent system in a process for producing hydrogen peroxide by an anthraquinone method.
Background
At present, more than 99% of the hydrogen peroxide products in the world are produced by an anthraquinone process, 2-alkyl anthraquinone is used as a working solution carrier, the anthraquinone working solution is subjected to catalytic hydrogenation and automatic oxidation reaction circularly and alternately, and then the hydrogen peroxide products with different concentrations can be obtained after extraction, refining and concentration. The working solution as the 'blood' of the anthraquinone process has a decisive influence on the production efficiency of each production unit. Under the premise that the physical and chemical properties of the working solution completely meet the industrial requirements, the industrial processH produced by single pass conversion of working fluid, typically in unit volume 2 O 2 Quality (H can be prepared per liter of working solution) 2 O 2 Grams) as an important indicator for the evaluation of productivity.
Because the molecular polarity difference of anthraquinone and its hydrogenated product is large, the single solvent is difficult to meet the above requirements of working solution, and the working solution solvent system is generally compounded by non-polar anthraquinone solvent and polar hydroanthraquinone solvent. The prior working solution solvent system has low solubility to anthraquinone and hydroanthraquinone, which causes low conversion rate of anthraquinone and low hydrogenation efficiency, and further causes large circulation of working solution in the device and small operation elasticity; the working solution has high density and viscosity, so that the extraction and separation effects are poor, the quality of the hydrogen peroxide product is severely limited, the quality grade of the hydrogen peroxide product is low, the consumption of anthraquinone is high, and the requirements of high-purity hydrogen peroxide products cannot be met.
CN1583546A discloses a ternary solvent system of arene, trioctyl phosphate and tetrabutyl urea, compared with a traditional binary working solution of arene and trioctyl phosphate, the solubility of hydroanthraquinone is improved by about 10%, and then the hydrogenation efficiency of the working solution is slightly improved, and the working solution has appropriate physical and chemical indexes of density, viscosity and the like, but the system is high in water intersolubility. CN1552618A discloses an arene + trioctyl phosphate + methyl cyclohexyl acetate ternary solvent system, compared with a traditional arene + trioctyl phosphate binary working solution, the solubility of the system to 2-ethyl anthraquinone can be improved by 30g/L, the hydrogenation efficiency of the working solution can be improved to 9 to 10g/L, and the density and viscosity of the working solution are larger. EP0287421 discloses an aromatic hydrocarbon + N-phenyl N-ethyl Benzamide (BEA) binary solvent system, which has obviously improved solubility on anthraquinone and hydroanthraquinone, but the working solution has higher density and high water solubility, so that the extraction and separation effects are poor, carbon residue in hydrogen peroxide products is higher, the application effect is poor, and the requirements of large-scale industrial application cannot be met.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a hydrogen peroxide working solution solvent system. The working liquid system has the physicochemical properties of lower density, viscosity and the like, has good dissolving capacity for anthraquinone and hydroanthraquinone thereof, can obviously improve the operating efficiency of a hydrogen peroxide device, reduces the asset investment and the production operating cost, and has good industrial application prospect.
The hydrogen peroxide working solution solvent system comprises the following components: aromatic hydrocarbons, imide derivative a and Diisobutylcarbinol (DIBC); wherein the structural formula of the imide derivative A is as follows:
wherein R is 1 、R 2 、R 3 The functional group is one of furan, an aromatic hydrocarbon substituent, benzyl or an alkane substituent with 1 to 8 carbon atoms, and the furan, the aromatic hydrocarbon substituent, the benzyl or the alkane substituent further contains one or more functional groups of alkyl, alkoxy and ester groups; the aromatic hydrocarbon is 30 to 95 parts by volume, preferably 60 to 80 parts by volume, the diisobutylcarbinol is 2 to 20 parts by volume, preferably 5 to 15 parts by volume, and the imide derivative A is 5 to 30 parts by volume, preferably 5 to 15 parts by volume.
In the present invention, the aromatic hydrocarbon is generally C 9 ~C 10 Aromatic hydrocarbons; imide derivative A in the molecule R 1 ~ R 3 Preferably C 2 ~C 6 The normal/isomeric alkyl substituent group can distribute and adjust the carbon atom number of the substituent group at different positions according to different physical and chemical property requirements of the working solution, but the total carbon atom number is not higher than 20.
The invention also provides hydrogen peroxide working solution containing the solvent system, and the working carrier of the working solution is one or more of anthraquinone and derivatives thereof, preferably 2-alkylanthraquinone, and further preferably 2-ethylanthraquinone, 2-butylanthraquinone or 2-amylanthraquinone.
The invention also provides a hydrogenation process for producing hydrogen peroxide by an anthraquinone method, wherein a working solution solvent system containing the imide derivative A and the aromatic hydrocarbon is adopted in the hydrogenation step. The process conditions of the hydrogenation step are: the hydrogenation temperature is 30-80 ℃, the pressure is 0.1-0.7 MPa, and the hydrogenation reactor can be a fluidized bed, a slurry bed or a fixed bed.
The hydrogenation process can adopt a hydrogenation catalyst well known in the technical field of anthraquinone process, the hydrogenation active component is generally Pd, the carrier is generally alumina or silica gel, and an auxiliary agent component such as one or more of Mo, na, K, ni, mg, au, ca, fe and the like can also be added into the catalyst, wherein the hydrogenation active component content is 0.05-5% and the auxiliary agent content is 0.05-3% by weight of the hydrogenation catalyst component.
In the process of applying the hydrogen peroxide working solution to the anthraquinone process, the oxidation step can adopt air or pure oxygen or other conventional oxidants, preferably air. The process conditions for the oxidation step are typically: the oxidation temperature is 25-70 ℃, and the pressure is 0.1-0.5 MPa.
Compared with the existing hydrogen peroxide working solution in industry, the novel working solution provided by the invention has the following characteristics: (1) The solubility of the working solution to 2-alkylanthraquinone can reach more than 180g/L under normal temperature and normal pressure conditions, and the solubility of the working solution to 2-alkylhydroanthraquinone can reach more than 99.8g/L under the working condition of an anthraquinone method, so that the effective anthraquinone concentration in the working solution can be greatly improved, and the hydrogenation conversion rate of anthraquinone can be improved; (2) The hydrogenation efficiency is high, the degradation rate of anthraquinone, and the hydrogenation efficiency of the working solution under the condition of an industrial conventional anthraquinone hydrogenation catalyst can reach more than 13 g/L; (3) The physical and chemical properties of the working solution are suitable for the anthraquinone process, the working solution has low intersolubility with water and low density and viscosity, and can meet the industrial production requirements of hydrogen peroxide.
Detailed Description
The invention is further described below with reference to specific preferred embodiments, without thereby limiting the scope of protection of the invention.
The invention evaluates the solubility of different working solution systems to anthraquinone and hydroanthraquinone and the carbon residue index in hydrogen peroxide products according to the following processes:
(1) Anthraquinone solubility analysis: the solubility of anthraquinone is measured by a solid-liquid dissolution equilibrium method. Under the constant temperature condition of 25 ℃, 2-alkyl anthraquinone is gradually dissolved in 200 mL of working solution, after the anthraquinone reaches solid-liquid two-phase equilibrium and is not dissolved any more, the working solution is stood for 2 hours, 1mL of upper clear solution is taken to be dissolved in acetonitrile after complete layering, and the concentration of the anthraquinone in the working solution is measured by high performance liquid chromatography analysis after 200 times of dilution. The high performance liquid chromatography test conditions are as follows: agilent HPLC 1260, 4.6 × 250mm × 5um Eclipse PAH reverse chromatography column with acetonitrile/water =80/20 as mobile phase, uv detector, detection wavelength 255nm, mobile phase flow rate 1mL/min, sample size 1mL, column temperature 308.15K. In the process of measuring the solubility, the temperature precision is +/-0.03 ℃, the high performance liquid analysis error is 0.1mg, and the average value of three parallel experimental data is the experimental value of the solubility of the anthraquinone measured under the condition.
(2) Hydroanthraquinone solubility analysis: the solubility of the hydroanthraquinone is obtained by a critical hydrogenation experiment, the working solution is subjected to hydrogenation reaction in a transparent and visible fixed bed reactor, the flowing condition of the working solution in the fixed bed layer is observed by a laser detector, and the hydrogenation reaction is stopped when the working solution reaches a critical crystallization precipitation state. Analyzing the composition of the hydrogenated liquid with High Performance Liquid Chromatography (HPLC) to 1mL of hydrogenated liquid, and completely oxidizing with air or oxygen to 5mL of hydrogenated liquid with potassium permanganate (KMnO) 4 ) And (3) analyzing the mass concentration of hydrogen peroxide in the oxidizing solution by a titration method, and calculating the solubility of the hydroanthraquinone in different solvent systems by using the hydrogenation efficiency value under the condition of analyzing the working solution by high performance liquid chromatography without anthraquinone degradation products.
(3) Analysis of carbon residue in hydrogen peroxide: and (3) extracting hydrogen peroxide in the oxidation solution by using deionized water, standing for more than 24 hours, extracting 50mL of extraction liquid at one time after the extraction phase and the raffinate phase are completely layered, and analyzing the content of residual carbon in the extraction liquid by using a TOC carbon residue instrument.
The invention also provides a synthesis method of the imide derivative A, which comprises the following steps:
(1) Dissolving carboxylic acid A and carboxylic acid B in an organic solvent, performing intermolecular dehydration reaction under the conditions of a catalyst A, a dehydrating agent A and high temperature, separating the dehydrating agent A after the reaction is finished, and then performing extraction separation to obtain inorganic extract and organic raffinate containing anhydride C;
(2) Reacting the organic raffinate containing the anhydride C obtained in the step (1) with an ammonia source at a low temperature for a period of time and then at a high temperature for a period of time under the action of a catalyst B and a dehydrating agent B, and separating an inorganic phase after the reaction is finished to obtain an organic solution containing imide D;
(3) Adding a proper amount of halohydrocarbon into an organic solution containing the imide D, carrying out nucleophilic substitution reaction under the condition of weak base or strong base, washing and extracting after the reaction is finished to obtain an organic extraction phase, carrying out reduced pressure distillation to remove the solvent, and drying to obtain the imide derivative product.
In the method of the present invention, the step (1) is to form a polymeric acid anhydride C having a different structural functional group by intermolecular dehydration of a carboxylic acid A and a carboxylic acid B having a different or the same structural functional group.
The dehydration reaction formula in the step (1) is as follows:
in the process of the present invention, the carboxylic acid A (R) described in the step (1) 1 COOH) and carboxylic acid B (R) 2 COOH) wherein R 1 And R 2 Is furan, a mono-substituted or multi-substituted aromatic hydrocarbon substituent or benzyl, or a straight-chain or branched-chain alkane substituent; wherein, the substituent of the aromatic hydrocarbon or the substituent of the benzyl group can be one or more of alkyl, alkoxy, ester group and the like.
In the method, the organic solvent in the step (1) is selected from one or more of dimethylbenzene, trimethylbenzene, chlorobenzene, N-Dimethylformamide (DMF), ethyl acetate or pyridine and the like; the ratio of the organic solvent to the carboxylic acid is 2 to 10mL/g, preferably 3 to 6mL/g.
In the method, the catalyst A in the step (1) is an aqueous solution of sodium methoxide and ferric salt, the molar concentrations of the sodium methoxide and the ferric salt are respectively 0.01 to 5mol/L and 0.1 to 10mol/L, and the dehydrating agent A is P 2 O 5 ；
In the method of the present invention, the carboxylic acid A in the step (1): carboxylic acid B: catalyst A: the mol ratio of the dehydrating agent A is 1: 1: 0.15 to 0.5: 0.5 to 5.
In the method of the invention, the dehydration reaction conditions in the step (1) are as follows: reacting for 18 to 25 hours under the conditions of normal pressure and 40 to 80 ℃. And (3) selecting silica gel of 300-400 meshes by a layer-by-layer analysis method (ethyl acetate: n-hexane = 2). And after the reaction is finished, washing the reaction mixture for 3 times by using deionized water, extracting by using dichloromethane to obtain an organic extraction phase, distilling under reduced pressure to remove the solvent, and drying in an oven to obtain a target product, namely a white solid.
In the method, in the step (2), the reaction is firstly carried out prehydrolysis reaction at the low temperature of 25-50 ℃, and after the reaction substrate is activated in a catalytic system, ammonolysis reaction is carried out at the high temperature of 210-230 ℃.
The ammonolysis reaction formula in the step (2) is as follows:
in the method, the catalyst B and the dehydrating agent B in the step (2) are mixed solutions of triethylamine and potassium carbonate, the molar concentrations of the catalyst B and the dehydrating agent B are respectively 0.01-2mol/L and 0.5-10 mol/L, and 0.5-10, and the molar ratio of the triethylamine to the potassium carbonate is 1: 0.6-2.5.
In the method, the ammonia source in the step (2) is ammonia gas, ammonia water, ammonium bicarbonate or urea and the like, preferably ammonia gas or ammonia water, and the feeding molar ratio of the ammonia source to the acid anhydride C is 1.2 to 10:1.
in the method, the pressure in the step (2) is 0.1 to 0.5MPa.
In the method of the invention, the low-temperature reaction conditions in the step (2) are as follows: reacting for 2 to 5 hours at the temperature of 25 to 50 ℃; the high-temperature reaction conditions are as follows: reaction at 210-230 ℃ for 1-1.5 hours
In the method, the step (2) is preferably carried out in a high-temperature reaction process under the vacuum dehydration condition, wherein the vacuum degree is-0.01 to-0.1 MPa.
In the method of the present invention, in the step (2), preferably, the organic raffinate containing the acid anhydride C is added to the mixed solution of the catalyst B and the dehydrating agent B (triethylamine and potassium carbonate) in a batch feeding manner or a slow titration manner, and the addition time is preferably 25 to 35 minutes.
In the method of the present invention, in the step (3), the hydrogen halide produced by the nucleophilic substitution reaction (. Beta. -elimination reaction) is dissolved in an alkaline aqueous solution, and the target main product is dissolved in an organic solvent.
The reaction equation of the step (3) is as follows (taking brominated alkanes as an example):
in the method of the present invention, the reaction conditions in step (3) are: reacting at 25 to 50 ℃ for 8 to 15 hours.
In the method of the present invention, the drying conditions in step (3) are: drying for 12 to 24 hours under the conditions of normal pressure and temperature of 120 to 140 ℃.
In the method of the present invention, the washing in step (3) is generally performed 2 to 4 times with deionized water.
In the method of the present invention, the halogenated alkane described in step (3) is brominated alkane, chlorinated alkane, etc., preferably brominated alkane, and the molar ratio of the halogenated alkane to the carboxylic acid a is 1.2 to 1.5:1.
the invention also provides a hydrogenation process for producing hydrogen peroxide by an anthraquinone method, wherein the working solution is adopted in the reaction process. Wherein the process conditions of the hydrogenation process are as follows: the hydrogenation temperature is 30-80 ℃, the pressure is 0.1-0.7 MPa, and the hydrogenation reactor can be a fluidized bed, a slurry bed or a fixed bed. The hydrogenation process can adopt a hydrogenation catalyst well known in the technical field of anthraquinone process, the hydrogenation active component is generally Pd, the carrier is generally alumina or silica gel, and an auxiliary agent component such as one or more of Mo, na, K, ni, mg, au, ca, fe and the like can also be added into the catalyst, wherein the hydrogenation active component content is 0.05-5% and the auxiliary agent content is 0.05-3% by weight of the hydrogenation catalyst component.
In the process of applying the hydrogen peroxide working solution to the anthraquinone process, air or pure oxygen or other conventional oxidants can be adopted in the oxidation step, and air is preferred. The process conditions for the oxidation step are typically: the oxidation temperature is 25-70 ℃, and the pressure is 0.1-0.5 MPa.
Detailed Description
Example 1
Synthesis process of N-tertiary butyl di-tert-butyl imideFor example, the specific synthesis process of the imide derivative A is as follows: 176.2 g of t-butyric acid and 75 g of P were put into a 500mL reaction vessel at a time 2 O 5 Heating the system temperature to 65 ℃ with 50mL of mixed solution of sodium methoxide and ferric salt (wherein the sodium methoxide is 6.8g, and the ferrous nitrate is 10 g), reacting for 20 hours at constant temperature, finishing the reaction, and filtering out P 2 O 5 Powder, transferring the reaction solution into a paging funnel, fully washing the reaction solution for three times by using deionized water, and separating out an inorganic aqueous solution; returning the organic raffinate to the reaction kettle, filling a mixed gas of ammonia and nitrogen into a reaction system, increasing the pressure to 0.25 to 0.3MPa, reacting for 2 hours at 35 ℃, pumping a mixed solution of 50mL of potassium carbonate and 45 to 50wt.% of triethylamine into the reaction system for 20 minutes in the reaction process, increasing the temperature of the system to 120 ℃, reacting for 1.5 hours, and separating an inorganic phase from the mixed solution after the system is cooled to room temperature; adding 165g of 1-bromobutane into the residual organic phase reaction liquid, reacting for 12 hours at 35 ℃, selecting silica gel of 300-400 meshes by a layer-by-layer analysis method (ethyl acetate: N-hexane = 2. 1H NMR and MS spectrum analysis of the obtained product prove that the product is N-butyl di-tert-butyl imide, and the total yield is 95.6%.
1H NMR（500MHz，CDCl 3 ）δ=0.9~1.0（m，18H），1.9~2.05（m，1H），2.05~2.15（m，2H），2.25~2.4（m，4H），3.4~3.45（s，2H）；
MS[M+H] + ：241.7。
Example 2
Taking the synthesis process of N-isoamyl 1-isopropyl-2-tert-butyl imide as an example, the preparation method is similar to that of example 1, except that the reaction raw materials and the usage amount of the carboxylic acid A and the carboxylic acid B and the halogenated alkane are slightly adjusted according to the target product. 500 88.1g of t-butyric acid, 74.5g of propionic acid, and 71 g of P were put into a mL reaction vessel at a time 2 O 5 And 30mL of a mixed solution of sodium methoxide and an iron salt (wherein the amount of sodium methoxide is 5.4g, and the amount of ferrous nitrate is 9.1 g), obtaining an intermediate product by the preparation method in example 1, adding 165g of 1-bromopentane into the reaction solution of the intermediate product, reacting at 35 ℃ for 12 hours, selecting 300-400 mesh silica gel by a layer-by-layer analysis method (ethyl acetate: n-hexane = 2). The product was confirmed to have an N-isopentyl 1-isopropyl-2-tert-butylimide structure by 1H NMR and MS spectroscopic analysis, and the yield was 95.6% (based on the starting carboxylic acid).
1H NMR（500MHz，CDCl 3 ）δ=0.95~1.10（m，18H），2.07~2.17（m，1H），2.25~2.4（m，2H），2.5~2.55（m，2H），3.45~3.55（s，2H）；
MS[M+H] + ：241.3。
Example 3
In volume fraction, as C 9 ~C 10 A mixture of arene/diisobutyl carbinol/N-tertiary butyl di-tert-butyl imide =75/5/20 is used as a solvent system to prepare 2-ethyl anthraquinone working solution.
Analyzing the viscosity of the working solution according to GB 11137-20, and evaluating the hydrogenation reaction of the working solution by adopting a 500ml intermittent stirring reaction kettle, wherein the hydrogenation temperature is 45 to 50 ℃, the hydrogenation pressure is 0.1 to 0.3MPa, and the stirring speed is 300 to 400rpm; oxidizing the obtained hydrogenated liquid for 15 to 30 min at the temperature of 30 to 50 ℃ under normal pressure by using air; after the oxidizing solution is extracted for 4 times by pure water, measuring the content of hydrogen peroxide in the extract by a potassium permanganate titration method, and calculating the hydrogenation efficiency of the working solution; the catalyst used in the hydrogenation experiment adopts the Pd/Al which is conventional in the hydrogen peroxide industry 2 O 3 The catalyst has a particle diameter of 0.4 to 0.5mm and a pore volume of 0.6 to 0.7cm 3 The specific surface area is 150 to 180m2/g, and the Pd content is 0.25 to 0.30wt%.
The test result shows that: the working solution solvent system has a density of 0.917g/cm at 20 deg.C 3 The viscosity was 2.331 pas at 25 ℃ under normal pressureUnder the conditions, the solubility of 2-ethyl anthraquinone in the working solution solvent system is 195.1g/L, the solubility of 2-ethyl anthraquinone is 101.8 g/L under the conditions of 50 to 55 ℃ and 0.2 to 0.3MPa, the hydrogenation efficiency of the working solution with the mass concentration of the 2-ethyl anthraquinone of 180g/L is 13.6 g/L, and the organic carbon residue in the hydrogen peroxide product is 150 to 160ppm.
Example 4
In volume fraction, as C 9 ~C 10 A mixture of arene/diisobutylcarbinol/N-isoamyl 1-isopropyl-2-tert-butyl imide =70/15/15 is used as a solvent system to prepare 2-ethylanthraquinone working solution; the service performance evaluation conditions of the working solution system are similar to the process conditions of the example 3, and the only difference is that the hydrogenation temperature is 30 to 40 ℃. The test result shows that: the density of the working solution solvent system is 0.919g/cm at 20 DEG C 3 The viscosity is 2.261 pas, the solubility of the 2-ethyl anthraquinone in the working solution system under the conditions of 25 ℃ and normal pressure is 192.2g/L, the solubility of the 2-ethyl hydroanthraquinone under the conditions of 30 to 40 ℃ and 0.2 to 0.3MPa is 99.8g/L, the hydrogenation efficiency of the working solution with the mass concentration of the 2-ethyl anthraquinone of 180g/L is 13.1g/L, and the organic carbon residue in the hydrogen peroxide product is 140 to 155ppm.
Example 5
In volume fraction, as C 9 ~C 10 A mixture of arene/diisobutylcarbinol/N-ethyl 1-alkoxy-2-heptylimide =60/20/20 is used as a solvent system to prepare 2-amylanthraquinone working solution; the service performance evaluation conditions of the working solution system are similar to the process conditions of the example 3, except that the hydrogenation temperature is 55-65 ℃, and the hydrogenation pressure is 0.25-0.40MPa. The test result shows that: the working solution has a density of 0.927g/cm at 20 deg.C 3 The viscosity is 2.343 Pa.s, the solubility of the 2-amylanthraquinone in the working solution system under the conditions of 25 ℃ and normal pressure is 477.3g/L, the solubility of the 2-amylanthraquinone is 138.1 to 145.8 g/L under the conditions of 55 to 65 ℃ and 0.25 to 0.40MPa, the hydrogenation efficiency of the working solution with the mass concentration of the 2-amylanthraquinone of 460 g/L is 15.1 to 15.5 g/L, and the organic carbon residue in the dioxygen aquatic product is 150 to 160ppm.
Comparative example 1
In volume fraction, as C 9 ~C 10 Aromatic hydrocarbon/trioctyl phosphate =75/25 blendThe compound is used as a solvent system to prepare 2-ethyl anthraquinone working solution, and the working solution system is subjected to performance analysis by adopting the conditions of the example 1. The test result shows that: the working solution has a density of 0.927g/cm at 20 deg.C 3 Viscosity of 2.355 pas, 2-ethyl anthraquinone at 25 deg.C and normal pressure 9 ~C 10 The solubility of an aromatic hydrocarbon/trioctyl phosphate working solution system is 123 to 130 g/L, the solubility of 2-ethyl anthraquinone is 68.5 to 70 g/L under the conditions of 53 to 60 ℃ and 0.25 to 0.30MPa, the hydrogenation efficiency of the working solution with the mass concentration of the 2-ethyl anthraquinone of 125 g/L is 6.5 to 7.3g/L, and the organic carbon residue in the hydrogen peroxide product is 205 ppm.
Comparative example 2
Working solution is prepared according to CN1552618A, example 3, and performance analysis is carried out on the working solution system by adopting the conditions of example 1.
The test result shows that: the density of the working solution is 0.943g/cm at the temperature of 20 DEG C 3 The working solution with the mass concentration of 2-ethyl anthraquinone being 154 g/L and the viscosity being 2.511 pas, the temperature being 53 to 60 ℃, the pressure being 0.25 to 0.30MPa has the solubility to hydroanthraquinone of 51.5 to 53.1g/L, the hydrogenation efficiency being 7.4 to 7.8 g/L, and the organic carbon residue in the hydrogen peroxide being 351ppm.
Comparative example 3
A2-ethylanthraquinone working solution was prepared according to the aromatic hydrocarbon + N-phenyl N-ethylbenzamide (BEA) binary solvent system disclosed in EP0287421, and the performance of the working solution system was analyzed under the conditions of example 1. The test result shows that: the density of the working solution solvent system is 0.929g/cm at the temperature of 20 DEG C 3 The viscosity of the working solution is 2.432 pas, the solubility of the 2-ethyl anthraquinone in the working solution system under the conditions of 25 ℃ and normal pressure is 155 to 163g/L, the solubility of the 2-ethyl anthraquinone under the conditions of 55 to 60 ℃ and 0.25 to 0.30MPa is 85 to 89g/L, the hydrogenation efficiency of the working solution with the mass concentration of the 2-ethyl anthraquinone of 150 g/L is 10.33 g/L, and the organic carbon residue in the hydrogen peroxide product is 554.8 ppm.
Claims (15)
1. A hydrogen peroxide working solution solvent system is characterized by comprising the following components: aromatic hydrocarbons, imide derivative a and diisobutylcarbinol; wherein the structural formula of the imide derivative A is as follows:
wherein R is 1 、R 2 、R 3 The functional group is one of furan, an aromatic hydrocarbon substituent, benzyl or an alkane substituent with 1 to 8 carbon atoms, and the furan, the aromatic hydrocarbon substituent, the benzyl or the alkane substituent further contains one or more functional groups of alkyl, alkoxy and ester groups; 30 to 95 parts of aromatic hydrocarbon, preferably 60 to 80 parts of aromatic hydrocarbon, 2 to 20 parts of diisobutylcarbinol, preferably 5 to 15 parts of diisobutylcarbinol, and 5 to 30 parts of imide derivative A, preferably 5 to 15 parts of imide derivative A.
2. The hydrogen peroxide working solution solvent system according to claim 1, characterized in that: the furan, arene substituent, benzyl or alkane substituent also contains one or more functional groups of alkyl, alkoxy and ester groups.
3. The hydrogen peroxide working solution solvent system according to claim 1, which is characterized in that: the aromatic hydrocarbon is C 9 ~C 10 Aromatic hydrocarbons; imide derivative A in the molecule R 1 ~ R 3 Each being selected from C 2 ~C 6 N/iso alkyl substituent groups of (1).
4. The hydrogen peroxide working solution is characterized in that: the solvent system comprises the working solvent system and the working carrier as defined in any one of claims 1 to 3, wherein the working carrier is one or more of anthraquinone and derivatives thereof, and is preferably 2-alkyl anthraquinone.
5. A hydrogenation process for producing hydrogen peroxide by an anthraquinone method is characterized by comprising the following steps: the hydrogenation step adopts a working solution solvent system containing imide derivative A and aromatic hydrocarbon; the process conditions of the hydrogenation step are as follows: the hydrogenation temperature is 25-80 ℃, and the pressure is 0.1-0.7 MPa.
6. The working solution solvent system for producing hydrogen peroxide by the anthraquinone process according to any one of claims 1 to 3, which is characterized in that: the synthesis method of the imide derivative A comprises the following steps: (1) Dissolving carboxylic acid A and carboxylic acid B in an organic solvent, performing intermolecular dehydration reaction under the conditions of a catalyst A, a dehydrating agent A and high temperature, separating the dehydrating agent A after the reaction is finished, and then performing extraction separation to obtain inorganic extraction liquid and organic raffinate containing anhydride C; (2) Under the action of a catalyst B and a dehydrating agent B, reacting the organic raffinate containing the anhydride C obtained in the step (1) with an ammonia source at a low temperature for a period of time, then reacting at a high temperature for a period of time, and separating an inorganic phase after the reaction is finished to obtain an organic solution containing the imide D; (3) Adding a proper amount of halohydrocarbon into an organic solution containing the imide D, carrying out nucleophilic substitution reaction under the condition of weak base or strong base, washing and extracting after the reaction is finished to obtain an organic extraction phase, carrying out reduced pressure distillation to remove the solvent, and drying to obtain the imide derivative product.
7. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the carboxylic acid A (R) described in the step (1) 1 COOH) and carboxylic acid B (R) 2 COOH) wherein R 1 And R 2 Is furan, a mono-substituted or multi-substituted aromatic hydrocarbon substituent or benzyl, or a straight-chain or branched-chain alkane substituent; wherein, the substituent of the aromatic hydrocarbon or the substituent on the benzyl is one or more of alkyl, alkoxy and ester group.
8. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the organic solvent in the step (1) is selected from one or more of dimethylbenzene, trimethylbenzene, chlorobenzene, N-dimethylformamide, ethyl acetate or pyridine; the proportion of the organic solvent to the carboxylic acid is 2-10mL/g.
9. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the catalyst A in the step (1) is an aqueous solution of sodium methoxide and ferric salt, the molar concentrations of the sodium methoxide and the ferric salt are respectively 0.01 to 5mol/L and 0.1 to 10mol/L, and the dehydrating agent A is P 2 O 5 。
10. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the carboxylic acid A in the step (1): carboxylic acid B: catalyst A: the mol ratio of the dehydrating agent A is 1: 1: 0.15 to 0.5: 0.5 to 5.
11. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the dehydration reaction conditions in the step (1) are as follows: reacting for 18 to 25 hours under the conditions of normal pressure and 40 to 80 ℃.
12. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the catalyst B and the dehydrating agent B in the step (2) are mixed solutions of triethylamine and potassium carbonate, the molar concentrations of the catalyst B and the dehydrating agent B are respectively 0.01-2mol/L and 0.5-10mol/L, and the molar ratio of the triethylamine to the potassium carbonate is 1: 0.6-2.5.
13. The method of claim 6, wherein: the method for synthesizing the imide derivative A is characterized in that: the ammonia source in the step (2) is ammonia gas, ammonia water, ammonium bicarbonate or urea, and the feeding molar ratio of the ammonia source to the acid anhydride C is 1.2 to 10:1.
14. the method of claim 6, wherein: in the synthesis method of the imide derivative A, the pressure in the step (2) is 0.1 to 0.5MPa; the low-temperature reaction conditions are as follows: reacting for 2 to 5 hours at the temperature of 25 to 50 ℃; the high-temperature reaction conditions are as follows: reaction at 310-320 ℃ for 1-1.5 hours.
15. The method of claim 6, wherein: in the method for synthesizing the imide derivative A, the reaction conditions in the step (3) are as follows: reacting for 8 to 15 hours at the temperature of 25 to 50 ℃; the molar ratio of the halogenated alkane to the carboxylic acid A is 1.2 to 1.5:1.
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