CN113897247B - Preparation of biodiesel by photo-magnetic dual-response emulsion method - Google Patents

Preparation of biodiesel by photo-magnetic dual-response emulsion method Download PDF

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CN113897247B
CN113897247B CN202111191876.5A CN202111191876A CN113897247B CN 113897247 B CN113897247 B CN 113897247B CN 202111191876 A CN202111191876 A CN 202111191876A CN 113897247 B CN113897247 B CN 113897247B
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methanol
catalyst
fatty acid
reaction
soybean oil
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CN113897247A (en
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应安国
鲁小彤
李胜男
王丽敏
黄素娟
刘中秋
刘玉静
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Zhongchuang Lian Investment Hubei New Energy Co.,Ltd.
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Qufu Normal University
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/069—Hybrid organic-inorganic polymers, e.g. silica derivatized with organic groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
    • B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/33—Electric or magnetic properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The invention relates to a method for preparing biodiesel by catalyzing soybean oil with green and high-efficiency solid interface nano particles. The method comprises the steps of taking a double-alkaline ionic liquid loaded by magnetic nano particles and a light responsive monomer as catalysts, and carrying out transesterification reaction on fatty acid substances in soybean oil and methanol at 50-60 ℃ under normal pressure to obtain corresponding fatty acid methyl ester. After the reaction is finished, the catalyst can be quickly recovered through external magnetic field and ultraviolet irradiation, and can be repeatedly used for a plurality of times, the reaction yield is not obviously reduced, and the yield of the effective component of the biodiesel, namely fatty acid methyl ester, reaches 91.05-98.20%. The catalyst system has the advantages of simple operation, good reusability, mild condition, high yield, simple catalyst recovery and good industrial prospect.

Description

Preparation of biodiesel by photo-magnetic dual-response emulsion method
Technical Field
The invention relates to a method for producing biodiesel by catalyzing transesterification of methanol and soybean oil by novel photo/magnetic double-response Pickering solid interface nano particles with high efficiency and no pollution.
Background
Diesel has become an important energy fuel as an important refinery product. With the worldwide popularity of diesel, the demand for diesel in the future will be increasing. Since the 90 s of the 20 th century, biodiesel has been attracting attention due to its superior environmental performance. The biodiesel can be prepared by taking animal and vegetable oil and waste oil as raw materials and performing transesterification reaction with methanol, and the biodiesel comprises an acid-base catalysis method, an enzyme catalysis method and a critical method. The biodiesel synthesized by the process has the following defects: the reaction condition is strict, the process is complex, the service life of the catalyst is short, the corrosiveness is strong, the saponification is easy, and the environment is polluted.
Pickering surfactant materials have received considerable attention in the past decade for similar functionality to conventional molecular surfactants, stabilizing droplet coalescence at the oil/water interface to improve interfacial mass transfer in multiphase systems. Based on the characteristic that the solid catalyst is easy to separate from biodiesel and recycle, the heterogeneous catalyst prepared by grafting the acid-base ionic liquid onto the metal-organic framework or the core-shell composite material is used for producing the biodiesel. The method has the advantages of simplifying the process flow and avoiding pollutant discharge. Has great potential in industrial scale production of biodiesel.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for producing biodiesel by utilizing light/magnetism dual-response Pickering solid interface nano-particle catalysis. The biodiesel is produced by taking the soybean oil and the methanol as raw materials, and the defects that the catalyst is difficult to separate and the mass transfer resistance of a two-phase interface is large are overcome.
The invention provides a preparation method of an optical/magnetic dual-response Pickering solid interface nanoparticle, which comprises the following steps:
1) Dissolving equimolar amounts of triethylene diamine and 2-bromoethyl acid ester in a methanol solution, heating and refluxing for 24 hours under the protection of vacuum nitrogen, and distilling under reduced pressure to remove the solvent to obtain light yellow viscous double-alkali ionic liquid;
2) Dissolving an equimolar amount of spiropyran precursor-SP and triethylamine in tetrahydrofuran solution, slowly dropwise adding acryloyl chloride into the solution under the protection of vacuum nitrogen, stirring for 24 hours at 40 ℃, and removing the solvent by reduced pressure distillation after column chromatography to obtain pale yellow spiropyran pure product;
3) The double alkaline ionic liquid and the spiropyran pure product obtained in the step 1) and the Fe modified by terminal alkene are prepared 3 O 4 Dissolving divinylbenzene and azodiisobutyronitrile in methanol, mechanically stirring at 70 ℃ for 6 hours, after the reaction is completed, cleaning the methanol until the methanol is clear, vacuum drying, adding sodium hydroxide methanol solution into the dried product, stirring, and vacuum drying to obtain the final catalyst.
In one embodiment according to the present invention, the molecular structure of the double basic ionic liquid is shown in the structural formula I.
Structural formula I
The molecular structure of the light-responsive monomer spiropyran is shown as a structural formula II:
structure II
In one embodiment according to the invention, the terminal-ene modified Fe of step 3) is modified with a metal 3 O 4 The molar ratio of divinylbenzene, bis-basic ionic liquid and spiropyran is 1:1:2:3. the initiator is azobisisobutyronitrile.
The invention also provides an optical/magnetic dual-response Pickering solid interface nanoparticle, and the catalyst is prepared according to the preparation method.
In one embodiment according to the invention, the molecular structure of the catalyst is shown in formula III.
Structural formula III
In another aspect of the present invention, there is provided a synthetic method for producing biodiesel, i.e., fatty acid methyl esters, comprising:
methanol and soybean oil are used as reaction substrates, and the catalyst is added to finally obtain the corresponding fatty acid methyl ester.
The yield of the effective component of the biodiesel, namely fatty acid methyl ester, reaches 91.05 to 98.20 percent through detection of a gas chromatograph-mass spectrometer
Preferably, the method further comprises the steps of separating and recovering the catalyst by external magnetic field and ultraviolet irradiation after the reaction is finished; the residue was concentrated under reduced pressure to remove impurities to give the product.
In one embodiment according to the invention, the molar ratio of methanol to soybean oil is 6:1-12:1.
in one embodiment according to the invention, the mass of the catalyst is 0.03-0.05 times that of soybean oil.
In one embodiment according to the present invention, the transesterification reaction time of soybean oil with methanol is 5 to 6 hours.
The beneficial effects of the invention are as follows:
1) After the reaction is finished, the catalyst provided by the invention can be recovered by using an external magnet and ultraviolet irradiation;
2) The catalyst obtained by recycling is washed by methanol, and can be used for the next batch of reaction after vacuum drying, the catalyst is reused for 6 times, and the reaction yield is not obviously reduced.
3) The synthesis method of biodiesel, namely fatty acid methyl ester, has the advantages of high yield, simple operation, simple catalyst recovery, good reusability of a catalytic reaction system, mild reaction conditions and good green industrialized prospect.
Detailed Description
The following detailed description of the preferred embodiments of the invention will provide those skilled in the art with a better understanding of the advantages and features of the invention, so as to make the scope of the invention more clearly and clearly defined.
Example 1 preparation of catalyst
1) The preparation process of the photo/magnetic dual-response Pickering solid interface nano-particles comprises the following steps:
dissolving equimolar amounts of triethylene diamine and 2-bromoethyl acid ester in a methanol solution, heating and refluxing for 24 hours under the protection of vacuum nitrogen, and distilling off the solvent under reduced pressure to obtain light yellow viscous double-alkali ionic liquid. The molecular structure of the double-alkaline ionic liquid is shown as a structural formula I:
structural formula I
2) Dissolving equal molar weight of spiropyran precursor-SP and triethylamine in tetrahydrofuran solution, slowly dropwise adding acryloyl chloride into the solution under the protection of vacuum nitrogen, stirring for 24 hours at 40 ℃, and removing the solvent by reduced pressure distillation after column chromatography to obtain pale yellow spiropyran pure product. The molecular structure of the light-responsive monomer spiropyran is shown as a structural formula II:
structure II
3) The obtained double-alkaline ionic liquid and spiropyran pure product and terminal alkene modified Fe 3 O 4 Dissolving divinylbenzene and azobisisobutyronitrile in methanol, and modifying Fe with terminal alkene 3 O 4 The molar ratio of divinylbenzene, bis-basic ionic liquid and spiropyran is 1:1:2: and 3, mechanically stirring for 6 hours at 70 ℃, after the reaction is finished, cleaning the methanol until the methanol is clear, vacuum drying, adding a sodium hydroxide methanol solution into the dried product, stirring, and vacuum drying to obtain the final catalyst. As shown in structural formula III.
Structural formula III
Example 2
The biodiesel is produced by catalyzing the reaction of methanol and soybean oil by using light/magnetism double-response Pickering solid interface nano particles.
Adding 0.33 g of methanol and 1.00 g of soybean oil (the molar ratio of the methanol to the soybean oil is 9:1) into a 50ml round bottom flask, adding 0.05 g of catalyst into the flask, sealing a glass plug, placing into a constant temperature oil bath pot, magnetically stirring for 300 revolutions per minute, reacting at 50 ℃ for 5 hours, magnetically adsorbing and ultraviolet irradiating to separate the catalyst after the reaction is completed, decompressing residual liquid to obtain the product biodiesel, and collecting and reusing the separated catalyst.
Taking 1 mg of the product, placing the product into a 2 ml sample tube, fixing the volume to 2 ml by using normal hexane, uniformly mixing, and detecting by using a gas chromatograph-mass spectrometer to obtain the yield of the active ingredient of the biodiesel, namely fatty acid methyl ester, which is 91.05%.
Example 3
Putting 0.22 g of methanol and 1.00 g of soybean oil (the molar ratio of the methanol to the soybean oil is 6:1) into a 50ml round bottom flask, adding 0.05 g of catalyst into the flask, sealing a glass plug, placing into a constant temperature oil bath pot, magnetically stirring for 300 revolutions per minute, reacting at 60 ℃ for 5 hours, magnetically adsorbing and ultraviolet irradiating to separate the catalyst after the reaction is completed, decompressing residual liquid to obtain the product biodiesel, and collecting and reusing the separated catalyst.
The yield of fatty acid methyl ester was 92.59% by the same assay as described in example 2.
Example 4
The reaction conditions and measurement methods were the same as in example 2 except that the reaction temperature was 60℃and the yield of fatty acid methyl ester was 98.2%.
Example 5
The reaction conditions and measurement methods were the same as in example 2 except that the catalyst was used in an amount of 0.03 g at a reaction temperature of 60℃and the yield of fatty acid methyl ester was 91.06%.
Example 6
The reaction conditions and measurement method were the same as in example 2 except that the reaction time was 5 hours and the reaction temperature was 60℃and the yield of fatty acid methyl ester was 97.04%.
Example 7
The reaction conditions and measurement were the same as in example 2 except that the amount of methanol was 0.44 g (molar ratio of methanol to soybean oil: 12:1), and the yield of fatty acid methyl ester was 97.1%.
Example 8
0.33 g of methanol, 1 g of soybean oil (molar ratio of methanol to soybean oil is 9:1), the externally-added magnet in example 4 and ultraviolet light are irradiated to recover the catalyst after vacuum drying at 80 ℃ for 3 hours, the catalyst is sequentially added into a 50mL single-port bottle, stirring is carried out at 60 ℃ for 5 hours, the catalyst and the product are separated by using external magnetic force and ultraviolet light, the obtained product is decompressed and concentrated, and finally, the detection is carried out by a gas chromatography-mass spectrometer, wherein the yield of fatty acid methyl ester is 96.45%. The catalyst was reused 6 times, and no significant drop in yield was observed, as shown in Table 1.
Table 1 catalyst performance test table
Number of times Temperature (. Degree. C.) Reaction time (h) Yield (%)
1 60 5 98.2
2 60 5 98.05
3 60 5 98
4 60 5 97.95
5 60 5 97.5
6 60 5 96.45
It should be noted that the foregoing summary and the detailed description are intended to demonstrate practical applications of the technical solution provided by the present invention, and should not be construed as limiting the scope of the present invention. Various modifications, equivalent alterations, or improvements will occur to those skilled in the art, and are within the spirit and principles of the invention. The scope of the invention is defined by the appended claims.

Claims (8)

1. A method for preparing biodiesel by a photo-magnetic double-response Pickering emulsion method is characterized by comprising the steps of taking magnetic nano particles loaded with double-alkaline ionic liquid and photo-responsive monomers as catalysts, and carrying out transesterification reaction on fatty acid substances in soybean oil and methanol at 50-60 ℃ under normal pressure to obtain corresponding fatty acid methyl ester; wherein the catalyst is:
,
the preparation method of the catalyst comprises the following steps:
1) Dissolving equimolar amounts of triethylene diamine and 2-bromoethyl acid ester in a methanol solution, heating and refluxing for 24 hours under the protection of vacuum nitrogen, and distilling under reduced pressure to remove the solvent to obtain light yellow viscous double-alkali ionic liquid;
2) Dissolving Spiropyran precursor-spirogyran and triethylamine with equal molar weight in tetrahydrofuran solution, slowly dripping acryloyl chloride into the solution under the protection of vacuum nitrogen, stirring for 24 hours at 40 ℃, decompressing and distilling to remove solvent after column chromatography to obtain pale yellow Spiropyran pure product,
3) The double alkaline ionic liquid and the spiropyran pure product obtained in the step 1) and the Fe modified by terminal alkene are prepared 3 O 4 Dissolving divinylbenzene and azobisisobutyronitrile in methanol, mechanically stirring at 70deg.C for 6 hr, cleaning with methanol, vacuum drying, and adding sodium hydroxideStirring the methanol solution, drying in vacuum to obtain the final catalyst,
the molecular structure of the double-alkaline ionic liquid is shown as a structural formula I:
,
the molecular structure of the light-responsive monomer spiropyran is shown as a structural formula II:
。
2. the method for producing biodiesel according to claim 1, wherein the terminal-ene-modified Fe in step 3) 3 O 4 The molar ratio of divinylbenzene, bis-basic ionic liquid and spiropyran is 1:1:2:3.
3. the method for preparing biodiesel according to claim 1, wherein the fatty acid substances contained in the soybean oil include stearic acid, palmitic acid, linoleic acid, oleic acid, and linolenic acid.
4. The method for preparing biodiesel according to claim 1, wherein the fatty acid methyl ester is methyl stearate, methyl palmitate, methyl linoleate, methyl oleate, methyl linolenate.
5. The method for preparing biodiesel according to claim 1, wherein the mass of the catalyst is 0.03 to 0.05 times that of soybean oil.
6. The method for preparing biodiesel according to claim 1, wherein the reaction process is solvent-free, the molar ratio of methanol to soybean oil is 6:1-12:1.
7. the method for producing biodiesel according to claim 1 or 5, wherein the reaction time is 5 to 7 hours.
8. The method for preparing biodiesel according to claim 1, wherein after the reaction, the catalyst is recovered by external magnetic field and ultraviolet irradiation, washed with methanol, and dried under vacuum at 80 ℃ for 3 hours for repeated use.
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CN115475657A (en) * 2022-09-24 2022-12-16 曲阜师范大学 Application of multifunctional polymeric ionic liquid solid base in efficient catalysis of conversion of lignin into monocyclic aromatic compounds
CN117225471B (en) * 2023-09-15 2024-02-20 曲阜师范大学 Pickering emulsion interface catalyst, preparation method thereof and method for discarding frying oil-based biodiesel

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CN103212445A (en) * 2013-04-10 2013-07-24 江南大学 Basic ionic liquid modified magnetic nanoparticle catalyst for synthesizing biodiesel and preparation method thereof
CN103881038A (en) * 2014-01-27 2014-06-25 浙江大学 Preparation method and application of triblock copolymer containing spiropyrane group
CN104087555A (en) * 2014-07-16 2014-10-08 江苏东博生物医药有限公司 Folic acid targeting magnetic color-developing nanoparticles and preparation method thereof
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