CN108130554A - A kind of method that sodium hypochlorite electro-catalysis 5-HMF prepares FDCA - Google Patents
A kind of method that sodium hypochlorite electro-catalysis 5-HMF prepares FDCA Download PDFInfo
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Abstract
The invention discloses a kind of methods that 5 HMF of sodium hypochlorite electro-catalysis prepares FDCA, it is characterised in that this method is：Mixed solution is obtained after at normal temperatures stirring evenly 5 HMF, sodium hypochlorite and alkaline solution, is mixed into anode electrolysis pond；It takes isometric with the mixed solution and is added in catholyte pond with the alkaline solution of the mixed solution neutral and alkali solution's solute equimolar concentration again；Using anode material as anode electrode, 1 ~ 12h is reacted under the potential of 1.0 2.0V, obtains FDCA.The present invention is for the first time using sodium hypochlorite and its effective chlorine composition of electrolysis as oxidant, it is anode electrode and oxidation reaction catalyst instead of traditional noble metal-based electrode material catalyst using cheap metal and metallic compound, with the mild electro-oxidation reaction of normal temperature and pressure instead of the heat catalysis of traditional high temperature and pressure, greatly reduce cost, simplify reaction process, the energy is saved, further improve the conversion ratio of 5 HMF, the yield and selectivity of FDCA is close, promotes the industrialized production of FDCA.
Description
Technical field
The present invention relates to fine chemistry industry and electrochemical field, specifically a kind of sodium hypochlorite electro-catalysis 5-HMF prepares FDCA
Method.
Background technology
At present, as the fossil fuels such as coal, oil and natural gas are reduced increasingly and the rapid growth of world population, exploitation
Biomass fuel that is renewable and having sustainable development and chemicals are extremely urgent.Lignocellulosic is a kind of in nature
Abundant, cheap and reproducible resource, it can be used to prepare some carbohydrate derivatives, and then can further synthesize 5-
Hydroxymethylfurfural (5-HMF).5-HMF is a kind of important intermediate for preparing the renewable chemicals of biomass and fuel.
2,5- furandicarboxylic acids (FDCA) are the derivatives of a kind of furans that 5-HMF is generated through peroxidization.It is
It is a kind of to synthesize the green monomer of furyl polyester and fine chemicals, and be considered as establishing following " green " chemistry
One of 12 kinds of basic compounds of industry have great potential using value.
In view of this potential using value of FDCA, exploitation green, cheap 5-HMF oxidations prepare FDCA new methods tool
It is significant.Traditional 5-HMF oxidations prepare FDCA, mainly using TEMPO as oxidant, noble metal gold, palladium, platinum etc.
As catalyst (Catal.Lett., 2011,141 (12), 1752.Green Chem., 2011,13 (4), 824.Green
Chem.,2013,15(8),2240.).These methods are higher there are oxidant and catalyst cost and the shortcomings of easy in inactivation.Closely
Also have over year using hydrogen peroxide or oxygen as oxidant, the report of base metal iron and copper as catalyst reduces anti-
Cost is answered, but product income is unsatisfactory, and most reaction conditions are high temperature and pressure, harsher (ACS Catalysis,
2015,5(11): 6529-6544.).With the development of science and technology FDCA is prepared as a kind of new using electrocatalytic oxidation 5-HMF
The synthetic method of type is of interest by people, but expensive noble metal catalyst and relatively low yield, also counteracts that it is used for
Large-scale industrial production.In conclusion nowadays it is badly in need of a kind of using mild reaction condition and the progress of cheap catalyst
Oxidation 5-HMF prepares the scheme of FDCA.
Invention content
In view of the deficiencies of the prior art, the technical issues of present invention intends to solve is to provide a kind of sodium hypochlorite electro-catalysis 5-
The method that HMF prepares FDCA.
The technical solution that the present invention solves the technical problem is to provide a kind of sodium hypochlorite electro-catalysis 5-HMF preparations
The method of FDCA, it is characterised in that this method is：After at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and alkaline solution
To mixed solution, it is mixed into anode electrolysis pond；It takes again isometric with the mixed solution and molten with the mixed solution neutral and alkali
The alkaline solution of liquid solute equimolar concentration is added in catholyte pond；Using anode material as anode electrode, in 1.0-
1~12h is reacted under the potential of 2.0V, obtains FDCA.
Compared with prior art, advantageous effect of the present invention is：For the first time with sodium hypochlorite and its effective chlorine composition of electrolysis
It is anode electrode and oxidation reaction catalyst instead of your traditional gold using cheap metal and metallic compound as oxidant
Belong to base electrode material catalyst, it is anti-instead of the thermocatalytic of traditional high temperature and pressure with the mild electro-oxidation reaction of normal temperature and pressure
Should, cost is greatly reduced, simplifies reaction process, has saved the energy, further improves the conversion ratio of 5-HMF, FDCA's
Yield and selectivity are close, promote the industrialized production of FDCA.The conversion ratio of 5-HMF reaches 100%, FDCA in 6 hours
Yield reach more than 99%, selectivity is close to 100%.
Specific embodiment
Specific embodiments of the present invention are given below.Specific embodiment is only used for that the present invention is further described, unlimited
The application scope of the claims processed.
The present invention provides a kind of methods that sodium hypochlorite electro-catalysis 5-HMF prepares FDCA, it is characterised in that this method
It is：The molar concentration of solute in alkaline solution is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and alkaline solution
For the mixed solution of 0.5M-1M, it is mixed into anode electrolysis pond；Take again it is isometric with the mixed solution and with it is described mix it is molten
The alkaline solution of liquid neutral and alkali solution's solute equimolar concentration is added in catholyte pond；It is electric using anode material as anode
Pole, Ag/AgCl are reference electrode, and platinum filament is auxiliary electrode, and 1~12h is reacted under the potential of 1.0-2.0V, obtains FDCA.
The alkaline solution is potassium hydroxide solution or sodium hydroxide solution；
The anode material is metal simple-substance, metal oxide, metal sulfide, metal phosphide or nucleocapsid；
The nucleocapsid is using metal simple-substance as core, and metal oxide, metal sulfide or the metal phosphide of same metal are
The nucleocapsid of shell；The metal is cobalt, nickel, copper or manganese；The preferred Cu of the anode material, Cu@CuS, Cu@CuO, Ni, Ni@
NiS、Ni@NiP、Ni@NiO、Mn@MnS、 Mn@MnO2、Co@Co9S8, Co@CoP or Co@Co3O4.@represents cladding, such as Cu@
CuO is a kind of nucleocapsid, means that CuO is coated with core Cu as shell；
The molar ratio of the 5-HMF and sodium hypochlorite is 1:1-2；The mass ratio of the 5-HMF and alkaline solution is 1:
50-150；The mass ratio of the 5-HMF and anode material is 10-50:1.
Using H-type electrolytic cell as reaction utensil, separated between anode and cathode with anion-exchange membrane.
This method is at normal temperatures using 5-HMF as reaction substrate, using anode material as anode electrode, sodium hypochlorite conduct
Oxidant, under different potentials, the Cl-, ClO-, Cl that are generated by anode electrolysis sodium hypochlorite2Effective chlorine compositions are waited as oxygen
Agent cooperates with the effect of the adsorption desorption of elctro-catalyst and anode material, 5-HMF is selectively oxidized to obtain FDCA.
Embodiment 1
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Cu@CuS, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 12h under the potential of 1.0V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 95%, selectively reaches 99%.
Embodiment 2
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Cu@CuS, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 8h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 98%, selectively reach 99%.
Embodiment 3
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Cu@CuO, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 10h under the potential of 1.0V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 96%, selectively reaches 99%.
Embodiment 4
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Cu@CuO, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 6h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 99%, selectively reach 99%.
Embodiment 5
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting simple substance Ni, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 8h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 95%, selectively reach 99%.
Embodiment 6
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Ni@NiS, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 12h under the potential of 1.0V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 95%, selectively reaches 99%.
Embodiment 7
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Ni@NiS, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 7h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 97%, selectively reach 99%.
Embodiment 8
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Ni@NiP, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 7h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 95%, selectively reach 98%.
Embodiment 9
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Ni@NiO, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 12h under the potential of 1.0V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 97%, selectively reaches 99%.
Embodiment 10
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Ni@NiO, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 7h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 99%, selectively reach 99%.
Embodiment 11
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Selecting Mn@MnS, Ag/AgCl is ginseng as anode electrode
Than electrode, platinum filament is auxiliary electrode, reacts 9h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 96%, selectively reach 99%.
Embodiment 12
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Select Mn@MnO2As anode electrode, Ag/AgCl is ginseng
Than electrode, platinum filament is auxiliary electrode, reacts 12h under the potential of 1.0V, obtains FDCA..After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 96%, selectively reaches 99%.
Embodiment 13
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Select Mn@MnO2As anode electrode, Ag/AgCl is ginseng
Than electrode, platinum filament is auxiliary electrode, reacts 8h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 99%, selectively reach 99%.
Embodiment 14
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Select Co@Co9S8As anode electrode, Ag/AgCl is ginseng
Than electrode, platinum filament is auxiliary electrode, reacts 8h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 97%, selectively reach 99%.
Embodiment 15
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Select Co@Co3O4As anode electrode, Ag/AgCl is ginseng
Than electrode, platinum filament is auxiliary electrode, reacts 10h under the potential of 1.0V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
Yield to 100%, FDCA reaches 96%, selectively reaches 98%.
Embodiment 16
Sodium hydroxide molar concentration is obtained after at normal temperatures stirring evenly 5-HMF, sodium hypochlorite and sodium hydroxide solution
For the solution of 0.5M, it is mixed into anode electrolysis pond；The molar ratio of wherein 5-HMF and sodium hypochlorite is 1:2；Take equimolar dense again
Isometric sodium hydroxide solution is spent to be added in catholyte pond；Select Co@Co3O4As anode electrode, Ag/AgCl is ginseng
Than electrode, platinum filament is auxiliary electrode, reacts 6h under the potential of 1.5V, obtains FDCA.After testing, the conversion ratio of 5-HMF reaches
The yield of 100%, FDCA reach 99%, selectively reach 100%.
(1) potential range is in 1.3-2.0V, with Cu@CuS, Ni@NiS, Ni@NiP, Mn@MnS, Co@Co9S8、Co@CoP
During for anode material, the conversion ratio of 5-HMF reaches 100% within 3 hours, in 8 hours the yield of FDCA reach 90% with
On, it is selective close to 99%.Especially with Cu@CuO, Ni@NiO, Co@Co3O4、Mn@MnO2It is small at 3 during for anode material
When interior 5-HMF conversion ratio reach 100%, the yield of FDCA reaches more than 99% in 6 hours, and selectivity is close to 100%.
(2) potential range is in 1.0-1.3V, with Cu, Cu@CuS, Ni, Ni@NiS, Ni@NiP, Mn@MnS, Co@Co9S8、
When Co@CoP are anode material, the conversion ratio of 5-HMF reaches 100% within 5 hours, and the yield of FDCA reaches in 12 hours
It is selective close to 95% to more than 85%.Especially with Cu@CuO, Ni@NiO, Co@Co3O4、Mn@MnO2During for anode material,
The conversion ratio of 5-HMF reaches 100% within 5 hours, and the yield of FDCA reaches more than 97% in 12 hours, selectively connects
Nearly 100%.
(3) with Cu@CuO, Ni@NiO, Co@Co3O4、Mn@MnO2It can be repeatedly used during for anode material.It repeats
After 20 times, electrocatalysis characteristic is basically unchanged.
The present invention does not address part and is suitable for the prior art.
Claims (8)
1. a kind of method that sodium hypochlorite electro-catalysis 5-HMF prepares FDCA, it is characterised in that this method is：At normal temperatures by 5-
HMF, sodium hypochlorite and alkaline solution obtain mixed solution after stirring evenly, and are mixed into anode electrolysis pond；It takes and is mixed with described again
Solution is isometric and is added to catholyte pond with the alkaline solution of the mixed solution neutral and alkali solution's solute equimolar concentration
In；Using anode material as anode electrode, 1 ~ 12h is reacted under the potential of 1.0-2.0V, obtains FDCA.
2. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that 5-HMF with
The molar ratio of sodium hypochlorite is 1:1-2.
3. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that 5-HMF with
The mass ratio of alkaline solution is 1:50-150.
4. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that 5-HMF with
The mass ratio of anode material is 10-50:1.
5. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that the alkalinity
Solution is potassium hydroxide solution or sodium hydroxide solution.
6. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that the anode
Material is metal simple-substance, metal oxide, metal sulfide, metal phosphide or nucleocapsid；The nucleocapsid be with
Metal simple-substance is core, and metal oxide, metal sulfide or the metal phosphide of same metal are the nucleocapsid of shell；It is described
Metal is cobalt, nickel, copper or manganese.
7. the method that the sodium hypochlorite electro-catalysis 5-HMF according to claim 1 or 6 prepares FDCA, it is characterised in that described
Anode material is Cu, Cu@CuS, Cu@CuO, Ni, Ni@NiS, Ni@NiP, Ni@NiO, Mn@MnS, Mn@MnO2、Co@Co9S8、Co@
CoP or Co@Co3O4。
8. the method that sodium hypochlorite electro-catalysis 5-HMF according to claim 1 prepares FDCA, it is characterised in that mixed solution
In alkaline solution solute molar concentration be 0.5M-1M.
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| CN110102350A (en) * | 2019-06-10 | 2019-08-09 | 湖南师范大学 | Catalyst and its preparation method and application for oxidative synthesis 2,5- furandicarboxylic acid |
| CN110205645A (en) * | 2019-04-23 | 2019-09-06 | 电子科技大学 | 5 hydroxymethyl furfural electroxidation is the all-hydrolytic device and reaction method of anode reaction |
| CN111334818A (en) * | 2020-02-28 | 2020-06-26 | 浙江糖能科技有限公司 | Device for electrolytic catalytic oxidation and method for preparing 2, 5-furandicarboxylic acid |
| CN112538636A (en) * | 2019-09-20 | 2021-03-23 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 2, 5-furandicarboxylic acid by electrocatalysis of 5-hydroxymethylfurfural oxidation and simultaneously preparing hydrogen by electrolyzing water |
| CN113668000A (en) * | 2021-08-18 | 2021-11-19 | 广州大学 | Gamma-MnO2Preparation method and application thereof |
| CN117742278A (en) * | 2024-02-07 | 2024-03-22 | 四川飞洁科技发展有限公司 | Intelligent monitoring and management method and system for sodium hypochlorite production process |
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| CN109837555A (en) * | 2019-04-11 | 2019-06-04 | 浙江工业大学 | A kind of method that nickel vanadium phosphide catalyst electrocatalytic oxidation produces 2,5- furandicarboxylic acid |
| CN110205645A (en) * | 2019-04-23 | 2019-09-06 | 电子科技大学 | 5 hydroxymethyl furfural electroxidation is the all-hydrolytic device and reaction method of anode reaction |
| CN110106514A (en) * | 2019-05-13 | 2019-08-09 | 浙江大学 | A kind of method that 5 hydroxymethyl furfural electrochemical oxidation prepares 2,5- furandicarboxylic acid |
| CN110102350A (en) * | 2019-06-10 | 2019-08-09 | 湖南师范大学 | Catalyst and its preparation method and application for oxidative synthesis 2,5- furandicarboxylic acid |
| CN110102350B (en) * | 2019-06-10 | 2021-12-10 | 湖南师范大学 | Catalyst for oxidative synthesis of 2, 5-furandicarboxylic acid and preparation method and application thereof |
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