AU2020102849A4 - Method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using one-step visible-light CO2 catalysis method - Google Patents

Method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using one-step visible-light CO2 catalysis method Download PDF

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AU2020102849A4
AU2020102849A4 AU2020102849A AU2020102849A AU2020102849A4 AU 2020102849 A4 AU2020102849 A4 AU 2020102849A4 AU 2020102849 A AU2020102849 A AU 2020102849A AU 2020102849 A AU2020102849 A AU 2020102849A AU 2020102849 A4 AU2020102849 A4 AU 2020102849A4
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light
derivatives
dialkyl urea
directly synthesizing
visible
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Ge DU
Yanxiong Fang
Chengchao Li
Liang Peng
Dalei Sun
Yating YANG
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Guangdong University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses a method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using a one-step visible-light C02 catalysis method, wherein the N, N' dialkyl urea and the derivatives thereof are obtained by synthesizing organic amine and C02 in the presence of a catalyst. The invention aims to provide a method for preparing N, N'-dialkyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant as resources

Description

Method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using one-step visible-light CO 2 catalysis method
TECHNICAL FIELD
[0001] The invention relates to the technical field of environmental protection, in particular to a method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using a one-step visible-light C02 catalysis method.
BACKGROUND
[0002] Emission of carbon dioxide in the flue gas of coal-fired power plants has become the largest source of carbon dioxide emission in China at present. In order to fulfill the commitment and responsibility of carbon emission reduction in China, as reported at present, a general method is to carry out carbon capture post-treatment on the carbon dioxide. The C02 capture is mainly divided into three types: post combustion capture, pre-combustion capture and oxygen-enriched combustion capture. The capture energy consumption and the CO are too high, becoming a common problem. The capture technology after combustion is relatively mature, and especially the application based on an amine chemical absorption method is wide. At present, the main factors restricting the commercial application of this technology are the high energy consumption and cost. In particular, the subsequent C02 desorption, compression and separation and transportation costs are obstacles to its industrialization process. Therefore, if the carbon dioxide in the flue gas of coal-fired power plants can be directly recycled as resources, not only the high energy consumption processes such as desorption, compression and transportation after capture can be effectively avoided, but also low energy consumption, carbon emission reduction and green resource recycling can be achieved with "double gaining". It has very important and considerable economic and social benefits.
SUMMARY
[0003] The invention aims to provide a method for preparing N, N'-dialkyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant as resources.
[0004] The technical scheme of the invention is as follows: a method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using a one-step visible light C02 catalysis method, wherein the N, N'-dialkyl urea and the derivatives thereof are obtained by synthesizing organic amine and C02 in the presence of a catalyst.
[0005] The reaction route involved is as follows:
0
N2 + CO2 - Visible light vwNHi NHy^ + H2P
[0006] 2 'r
[0007] In principle, the method is applicable to any aliphatic alkyl primary amine and the catalyst is any photo-catalytic material with a visible light response.
[0008] In the method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method, the organic amine is one or more of alicyclic amine, aromatic amine and naphthalene amine.
[0009] Any aliphatic alkyl primary amine may be used in the present invention such as aniline, n-propylamine, n-butylamine, triethylamine, n-butylamine, cyclohexylamine, cyclopentylamine, 1, 4-butanediamine, 1, 6-hexanediamine, n pentylamine, cyclopropylamine, n-hexylamine, cyclobutylamine, n-heptylamine, p methylaniline, diphenylamine, isopropylamine, isobutylamine, 2, 2, 4 trimethylcyclohexanediamine, dodecylamine, morpholine, N-methylaniline, diphenylamine, trifluoromethylaniline, 1-naphthylamine, and the like.
[0010] Organic amines used in the present invention are preferably n-butylamine, n propylamine, n-pentylamine, and aniline.
[0011] The catalyst used is any photo-catalytic materials with visual light responses, including all the organic and inorganic semiconductor materials and modified semiconductor materials thereof, such as ZnS, CdS, GaP, SiC, K7[PTi2W1004]6H20, CdxZni+xS, BaCrO4, SrCrO4, BiSbO4, Ini-xMxTaO4 (M=Sc, Ti, V, Cr, Mn, Fe, Co,
Ni, Cu, Zn), Ce2Ti27, Sm2Ti27, Nd2Zr2O7, Sm2Zr2O7, Gd2Ti2O7, TiO2, NaTaO3, ZnFe204, BaCr204, ZnY204, MgAl204, SrIn2O4, LaFeO3, LaNiO3, LaMnO3, Lao.sSr.2COO3, LaMno.5Cuo.03, CdSe, CdS, CdO, Fe203, MoO3, Cu20, MoS2, LaTiO2N, PbBi2Nb209, CaBi204, ZnIn2S4, CdS/TiO2, SnO2/TiO2, TiBi206,
W03/TiO2, Pt/ Ti2, Re complex catalyst (eg. 2, 2' - dipyridyl tricarbonyl rhenium
chlorin (bromide), Co- tetrazole heterocyclic compound, Ni- Carbene complex, thionine, TiO2 modified by surface photo-sensitive agents such as metalloporphyrin compounds, precious metal load modified TiO2 (Pt/ Ti2, Ru/TiO2), LaFeO3, LaNiO3, LaMnO3, Lao.sSr.2COO3, LaMno.5Cuo.03 as well as an organic-inorganic hybrid
catalyst that uses any of the above matters or above similar structures and is based on or grafted on or coated on an organic or inorganic carrier, wherein:
[0012] Organic carriers: functional ionic liquid mesoporous materials, ion exchange resins (Amberlite and Dowex) and spatially modified or structurally optimized polymer carriers.
[0013] Inorganic carriers: carbon nanotubes, graphene, AlPO4 (aluminium phosphate molecular sieve and Berlinite structure), A1203 (alumina), SiO 2 (silica, zeolite), Si-Al molecular sieves with different proportions and structures or the like.
[0014] In principle, types of the solvents used include: dimethyl sulfoxide (DMSO), sulfolane (TMS), propylene carbonate (PC), dimethylformamide (DMF), hexamethylphosphoric triamide (HMPA), N,N-dimethylformamide (DMF), N methylpyrrolidone (NMP), diethylene glycol dimethyl ether (DME), 1,3-dimethyl-2 imidazolinone (DMI), methyl tert-butyl ether (MTBE), Isopropyl ether (DIPE), methyl tert-butyl ether (MTBE), dimethyl sulfoxide (DMSO), anisole, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), diethylene glycol dimethyl ether (DME), dichloromethane (DCM), dioxane (Diox), isopropyl ether (DIPE), pyridine (Py), Acetonitrile (CAN), methyl tert-butyl ether (MTBE), acetone (DMK), isopropyl ether (DIPE), ethyl acetate (EA), ethanol (EtOH), methanol (MeOH), n-butanol, n-amyl alcohol, cyclohexanone, benzyl alcohol, isobutyl acetate, n-propanol, various functional group ionic liquids (IL) with Lewis basic functional group or alkaline functional groups or with L alkalinity or B alkalinity respectively, etc.
[0015] The solvent used in the present invention is preferably N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), N, N-dimethylformamide (DMF), diethylene glycol dimethyl ether (DME), 1, 3-dimethyl-2-imidazolinone (DMI), methyl tert-butyl ether (MTBE), dioxane (Diox), various kinds of functional group ionic liquids (IL) having Lewis basic groups or basic groups, or having L basic and B basic groups, respectively.
[0016] In the method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method, the concentration of the raw material organic amine is in the range of 20-90 wt%, preferably 30-70%; the molar amount of the catalyst is equivalent to 0.01-4.00%, preferably 0.05-2.0%, of the molar amount of the organic amine.
[0017] In the method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method, the molar amount of catalyst is equivalent to 0.01-4.00% of the molar amount of the organic amine, and the weight ratio of the organic amine to the solvent is 1-10:30.
[0018] In the method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method, the reaction temperature is between normal temperature and 120 °C, preferably between and 80 °C, the catalytic light is visible light first, the reaction time is between 4 and 72 hours, and preferably between 12 and 24 hours.
[0019] In the method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method, the reaction pressure is 0.1-8Mpa, preferably 1.0-7.5MPa; and C02 is sourced from combustion tail gas.
[0020] The beneficial effects of the present invention are as follows:
[0021] The method provided by the invention combines a method for amine chemical absorption and capture of carbon dioxide in flue gas of a coal-fired power plant, utilizes an advanced photo-catalytic technology, integrates in-situ absorption and conversion of carbon dioxide in the flue gas of the coal-fired power plant to N, N' dialkyl urea and derivatives thereof, and realizes direct resource utilization of the carbon dioxide in the flue gas of the coal-fired power plant.
DESCRIPTION OF THE INVENTION
[0022] The technical solution of the present invention will be described in further detail below with reference to the specific embodiments, but it is not intended to limit the present invention in any way.
[0023] EMBODIMENT 1:
[0024] A production method for preparing N, N'-dibutyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant as resources:
[0025] 10 ml (about 0.10 mol) of n-butylamine and 30 ml of N-methylpyrrolidone solvent are taken and put into a 100 ml high-pressure sapphire-material reaction kettle with a xenon lamp light source, an air compressor and magnetic stirring, then 1.5 g of BaCeO3 catalyst is added, at a normal temperature coal-fired power plant flue gas of a 1.5 MPa from the Huarun Haifeng carbon capture platform is filled, the reaction kettle is sealed, the air compressor is started, the pressure is increased to 7.5MPa, the xenon lamp light source is simultaneously turned on, the temperature is raised to 40 °C, the constant temperature reaction is carried out for 12 h, a light yellow reaction liquid is taken out after cooling and gas relief to a normal pressure and a normal temperature, the catalyst is filtered, the liquid obtained after the reaction is treated with rotary evaporation, gas chromatography-mass spectrometry is carried out on the rotary evaporation pressure-decreased concentrated solution, and as measured, the capture-in situ catalysis conversion rate of C02 in the flue gas of the coal-fired power plant is %.
[0026] Product component, selectivity and yield are shown in Table 1:
[0027] Table 1. Product Composition, Selectivity and Yield
[0028]
Product composition Selectivity (%) Yield (%)
N, N'-dibutyl urea 95.1 76.1
Butyl isocyanate 4.9 3.92
[0029] EMBODIMENT 2:
[0030] A production method for preparing N, N'-dipropyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant as resources:
[0031] 10ml (about 0.103mol) of n-propylamine and 30 ml of 1, 3-dimethyl-2 imidazolinone solvent are taken and put into a 100 ml high-pressure sapphire-material reaction kettle with a xenon lamp light source, an air compressor and magnetic stirring, then 1.8 g, 1.4g, 2, 2'-bipyridyl tricarbonyl rhenium bromide catalyst is added, at a normal temperature coal-fired power plant flue gas of a 2.0 MPa from the Huarun Haifeng carbon capture platform is filled, the reaction kettle is sealed, the air compressor is started, the pressure is increased to 5.0 MPa, the xenon lamp light source is simultaneously turned on, the temperature is raised to 35 °C, the constant temperature reaction is carried out for 12 h, a light yellow reaction liquid is taken out after cooling and gas relief to a normal pressure and a normal temperature, the catalyst is filtered, the liquid obtained after the reaction is treated with rotary evaporation, gas chromatography-mass spectrometry is carried out on the rotary evaporation pressure decreased concentrated solution, and as measured, the capture-in situ catalysis conversion rate of C02 in the flue gas of the coal-fired power plant is 65%.[0032] Product composition, selectivity and yield are shown in Table 1:
[0033] Table 2. Product Composition, Selectivity and Yield
[0034]
Product composition Selectivity (%) Yield (%)
N, N'-dipropyl urea 90 58.5
Propyl isocyanate 10 6.5
[0035] EMBODIMENT 3:
A production method for preparing N, N'-dihexyl urea by directly recycling carbon dioxide IN flue gas of a coal-fired power plant as resources:
[0037] 1.Olg (about 0.10mol) of n- hexylamine and 30 ml of dioxane solvent are taken and put into a 100ml high-pressure sapphire-material reaction kettle with a xenon lamp light source, an air compressor and magnetic stirring, then 1.6 g of Lao.8Sro.2COO3 catalyst is added, at a normal temperature coal-fired power plant flue gas of a 1.0 MPa from the Huarun Haifeng carbon capture platform is filled, the reaction kettle is sealed, the air compressor is started, the pressure is increased to 4.5 MPa, the xenon lamp light source is simultaneously turned on, the temperature is raised to 40 °C, the constant temperature reaction is carried out for 24 h, a light yellow reaction liquid is taken out after cooling and gas relief to a normal pressure and a normal temperature, the catalyst is filtered, the liquid obtained after the reaction is treated with rotary evaporation, gas chromatography-mass spectrometry is carried out on the rotary evaporation pressure-decreased concentrated solution, and as measured, the capture-in situ catalysis conversion rate of C02 in the flue gas of the coal-fired power plant is 90%.
[0038] Product composition, selectivity and yield are shown in Table 1:
[0039] Table 3. Product Composition, Selectivity and Yield
[0040]
Product composition Selectivity (%) Yield (%)
N, N'-dihexyl urea 96 86.4
Hexyl isocyanate 4 3.6
[0041] EMBODIMENT 4:
[0042] A production method for preparing N, N'-diphenyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant as resources:
[0043] The operation is the same as EMBODIMENT 1, the solvent N methylpyrrolidone (NMP) was replaced by 1-butyl-2, 3-dimethylimidazole tetrafluoroborate ionic liquid, the n-butylamine was replaced by aniline, the catalyst BaCeO3 was replaced by Ru/TiO2, the reaction temperature was 100 °C and the reaction time was 24 h. The other operation conditions were not changed. As measured, the capture-in situ catalysis conversion rate of C02 in the flue gas of the coal-fired power plant is 85%.
[0044] Product composition, selectivity and yield are shown in Table 3:
Table 4. Product Composition, Selectivity and Yield
[0046]
Product composition Selectivity (%) Yield (%)
N, N'-diphenyl urea 98 83.3
Phenyl isocyanate 2 1.7
[0047] EMBODIMENT 5:
[0048] A production method for preparing N, N'-dicyclohexyl urea by directly recycling carbon dioxide in flue gas of a coal-fired power plant:
[0049] Operations are the same as EMBODIMENT 1, the solvent N methylpyrrolidone (NMP) was replaced by tri-tert-butylphosphine tetrafluoroborate ionic liquid, n-butylamine was replaced by cyclohexylamine, the catalyst BaCeO3 was replaced by Ino.5Mno.5TaO4, the reaction temperature was 120 °C, and reaction time was 24 h. Other operation conditions were not changed. As measured, the capture-in situ catalysis conversion rate of C02 in the flue gas of the coal-fired power plant is 68%.
[0050] Product composition, selectivity and yield are shown in Table 4:
[0051] Table 5. Product Composition, Selectivity and Yield
[0052]
Product composition Selectivity(%) Yield (%)
N, N'-dicyclohexyl 95.2 64.7 urea
Cyclohexyl 4.8 3.3 isocyanate
Comparative Embodiment:
[0054] The same operating conditions in EMBODIMENT 1 were used, except that no catalyst was added. As measured, the capture rate of C02 in the flue gas of the coal fired power plant was 50%, and the capture-in situ catalysis conversion rate was 0%.
[0055] The above-mentioned contents are only preferred embodiments of the present invention, and any modifications, equivalent replacements, and improvements that conform to the spirit and spirit of the invention are intended to be included within the scope of the invention.

Claims (10)

Claims
1. A method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using a one-step visible-light C02 catalysis method, wherein the N, N'-dialkyl urea and the derivatives thereof are obtained by synthesizing organic amine and C02 in the presence of a catalyst.
2. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 1, wherein the organic amine is one or more of alicyclic amine, aromatic amine and naphthalene amine.
3. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 2, wherein the alicyclic amine is one of n-propylamine, n-butylamine, isobutylamine, n pentylamine, n-hexylamine, 1, 6-hexanediamine, 1, 4-butanediamine and other aliphatic amines, or one or more of cyclobutylamine, cyclopentylamine, morphine and morpholine; the aromatic amine is one or more of aniline, p-methylaniline, diphenylamine and trifluoromethyl aniline; and the naphthalene amine is one or more of 1-naphthylamine, 2-naphthylamine and beta-naphthylamine.
4. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 1, wherein the catalyst is an inorganic or organic semiconductor material or a modified semiconductor material with visible light responses.
5. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 4, wherein the inorganic semiconductor material is a novel p-n heterojunction photocatalyst or an ohmic contact composite semiconductor consisting of CdSe, CdS, CdO, Fe203, MoO3, Cu20, W0 3 , TiO2, V205, ZnO, TaO3, ZrO2, Ir304, Co304, SnO2, PdO, BiPO4, MoS2, IrO2 or PtO 2; ABO3 structure compounds with structures of perovskite or perovskite-like structures.
The organic semiconductor material is naphthalimide, perylene imide, pentacene, triphenylamine, fullerene, phthalocyanine, perylene derivative or cyanine small molecule type organic semiconductor material, polyacetylene type, polyphenyl, polythiophene, polyaniline, polypyrrole and other polyaromatic ring type, copolymer type high molecular type organic semiconductor material;
The modified semiconductor material is phthalocyanine dye, rose red, 8 hydroxyquinoline, thionin, metalloporphyrin compound and the like.
The photosensitizer modifies a semiconductor of TiO2, 2, 2'-bipyridyl tricarbonyl rhenium chloride (bromide), a cobalt-tetraazacyclo compound and a nickel-carbene complex.
6. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 1, wherein the reaction is carried out in a solvent, and the solvent is dimethyl sulfoxide (DMSO), sulfolane (TMS), propylene carbonate (PC), dimethylformamide (DMF), hexamethylphosphoric triamide (HMPA), N,N-dimethylformamide ( DMF), N methylpyrrolidone (NMP), diethylene glycol dimethyl ether (DME), 1,3-dimethyl-2 imidazolinone (DMI), methyl tert-butyl ether (MTBE), Isopropyl ether (DIPE), methyl ether, tetrahydrofuran (THF), N-dimethylacetamide, diethylene glycol dimethyl ether (DME), dichloromethane (DCM), dioxane (Diox), isopropyl ether (DIPE), pyridine (Py), Acetonitrile (CAN), 1, 3-dimethyl-2- imidazolone, acetone, acetone (DMK), isopropyl ether (DIPE), ethyl acetate (EA), ethanol (EtOH), methanol (MeOH), n-butanol, n-amyl alcohol, various functional group ionic liquids (IL) with Lewis basic functional group or alkaline functional groups or with L alkalinity or B alkalinity respectively, etc.
7. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to any one of claims 1-6, wherein the molar amount of the catalyst is equivalent to 0.01-4.00% of the molar amount of the organic amine.
8. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to claim 6, wherein the molar amount of the catalyst is equivalent to 0.01-4.00% of the molar amount of the organic amine; and the weight ratio of the organic amine to the solvent is 1-10:30.
9. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to any one of claims 1-6, wherein the reaction temperature is from room temperature to 120 °C, the catalytic light is visible light first, and the reaction time is 4-72 hours.
10. The method for directly synthesizing the N, N'-dialkyl urea and the derivatives thereof by using the one-step visible-light C02 catalysis method according to any one of claims 1-6, wherein the reaction pressure is 0.1-8Mpa; and the C02 is sourced from combustion tail gas.
AU2020102849A 2020-10-19 2020-10-19 Method for directly synthesizing N, N'-dialkyl urea and derivatives thereof by using one-step visible-light CO2 catalysis method Ceased AU2020102849A4 (en)

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Cited By (2)

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CN113999383A (en) * 2021-11-16 2022-02-01 东华大学 Carbon dioxide-based high-molecular dye and preparation method and application thereof
CN114591338A (en) * 2022-03-31 2022-06-07 苏州欧康维视生物科技有限公司 Preparation method and application of Syk and VEGFR2 double-target inhibitor

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113999383A (en) * 2021-11-16 2022-02-01 东华大学 Carbon dioxide-based high-molecular dye and preparation method and application thereof
CN113999383B (en) * 2021-11-16 2023-08-29 东华大学 Carbon dioxide-based high-molecular dye and preparation method and application thereof
CN114591338A (en) * 2022-03-31 2022-06-07 苏州欧康维视生物科技有限公司 Preparation method and application of Syk and VEGFR2 double-target inhibitor
CN114591338B (en) * 2022-03-31 2023-05-09 苏州欧康维视生物科技有限公司 Preparation method and application of Syk and VEGFR2 double-target inhibitor

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