CN106268938B - A kind of bisgallic acid position solid-carrying type ionic-liquid catalyst of biodiesel synthesis and preparation method thereof - Google Patents

A kind of bisgallic acid position solid-carrying type ionic-liquid catalyst of biodiesel synthesis and preparation method thereof Download PDF

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CN106268938B
CN106268938B CN201610631674.0A CN201610631674A CN106268938B CN 106268938 B CN106268938 B CN 106268938B CN 201610631674 A CN201610631674 A CN 201610631674A CN 106268938 B CN106268938 B CN 106268938B
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CN106268938A (en
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范明明
刘慧�
张萍波
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Jiangnan University
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    • 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
    • B01J31/0292—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 immobilised on a substrate
    • B01J31/0295—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 immobilised on a substrate by covalent attachment to the substrate, e.g. silica
    • 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
    • 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
    • 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
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • 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)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses bisgallic acid position solid-carrying type ionic-liquid catalysts of a kind of biodiesel synthesis and preparation method thereof.With acid mesoporous material SO4 2‑/ZrO2‑SiO2For carrier, by acidic ion liquid [Ps im] HSO4It is immobilized in the SO through chemical bonding4 2‑/ZrO2‑SiO2On carrier, the ionic liquid supported type catalyst SO for possessing bisgallic acid position is obtained4 2‑/ZrO2‑SiO2IL, i.e. ionic liquid are providedThe Lewis acid position that sour position and carrier are provided.It is an advantage of the current invention that preparing gained SO4 2‑/ZrO2‑SiO2IL catalyst for soybean oil and methanol transesterification biodiesel synthesis, catalyst show in the reaction high activity, be easily recycled, thermal stability is good, corrosivity is small the advantages that, it is expected to become the cleaning procedure route of great competitiveness.

Description

A kind of bisgallic acid position solid-carrying type ionic-liquid catalyst of biodiesel synthesis and its preparation Method
Technical field
The present invention relates to bisgallic acid position solid-carrying type ionic-liquid catalysts of a kind of biodiesel synthesis and preparation method thereof, belong to In catalytically synthesizing biological diesel oil technical field.
Background technology
The rise of oil price and the increase of oil product demand promote people to find other reproducible novel energies, come It is a kind of reproducible liquid fuel from the biodiesel of triglycerides, is expected to the increase of compensation petroleum fuel demand.Biological bavin The main component of oil is carbon chain lengths in C12-C22Fatty-acid monoester, have physicochemical properties similar with petrifaction diesel, And possess renewable, zero sulphur emissions, it is biodegradable, nontoxic the advantages that.
Biodiesel generally by animal and plant fat (such as soybean oil, sunflower oil, palm oil) and short chain alcohol (such as methanol, Ethyl alcohol) it is made by acid or base-catalyzed transesterification.Base catalysis, mild condition, but raw material need to be pre-processed, complex process； Industrially application is more is usually homogeneity acid for acidic catalyst, and such as sulfuric acid, though catalytic activity is high, side reaction is few, pair sets Standby corrosion is big, it is difficult to recycle, product need to neutralize washing, generate a large amount of pollution；Solid acid catalyst can be eliminated together Many technologies and environmental problem caused by matter acid catalyst, but catalytic activity is relatively low.Therefore, Recent study personnel pay close attention to The research and development of the new and effective solid acid catalyst of biodiesel synthesis.
Ionic liquid (Ionic Liquids, ILs) is due to many excellent characteristics, such as excellent electric conductivity, wider Liquid range, adjustable physicochemical properties and good thermal stability, be widely used as catalyst.But the valence of ionic liquid Lattice are expensive, consumption is big and are difficult to detach in use and reuse, thus with a certain distance from having from industrial applications.In order to The above problem is solved, ionic liquid is made to obtain industrial applications early, scientists start to explore synthesis load-type ion liquid (SILs), i.e., ionic liquid is loaded on a solid carrier in method physically or chemically, it is made both to have retained ionic liquid characteristic While also have solid phase it is easily separated and recycling the advantages that.
Pure silicon mesoporous material such as SBA-15, MCM-41 etc. have regular pore passage structure, excellent Surface Physical Chemistry Matter and good heat and the advantages that hydrothermal stability, are used as all kinds of catalyst carriers, but pure silicon mesoporous material itself acid amount with Acid strength is weak, thus catalytic activity is relatively low.Super acids SO4 2-/ZrO2Itself there is the high acid strength better than liquid acid, but exist Porosity is poor, specific surface area is small and active component SO4 2-The shortcomings of being easy to run off, the organic reaction participated in for macromolecular have one Fixed limitation.By the structural advantage and SO of pure silicon mesoporous material4 2-/ZrO2Highly acid advantage combine, can be obtained sour strong Spend higher mesoporous material i.e. SO4 2-/ZrO2-SiO2.Ionic liquid is immobilized on this stronger Jie of acidity in the method for chemistry Porous materials, you can obtain the solid acid catalyst for possessing mesoporous type, which had both possessed what ionic liquid was providedAcid also possesses the Lewis acid that carrier is provided.Gained bisgallic acid position solid-carrying type ionic-liquid catalyst is not only active It is high and easily separated, repeatable to utilize, it is a kind of novel, efficient green catalyst.
Invention content
The object of the present invention is to provide a kind of efficient, stable, segregative bisgallic acid position solid-carrying type is ionic liquid-catalyzed The preparation method of agent, and the application that the catalyst is synthesized in biodiesel is provided.
The preparation method of bisgallic acid position solid-carrying type ionic-liquid catalyst of the present invention, detailed process is as follows,
(1) mesoporous material SO4 2-/ZrO2-SiO2Synthesis：It is a concentration of that 58mL is added in the F127 of the MW=12600 of 1g In the HCl solution of 2mol/L, 30~40 DEG C are uniformly mixed, and the TMB of 4.6mL is added in above-mentioned solution, continue constant temperature and stir 2~3h is mixed, TEOS, Zr (n-OBu) are sequentially added into above-mentioned reaction mixture4(NH4)2SO4Aqueous solution, control silicon and The molar ratio of zirconium is 0.5~2:1, the molar ratio of sulphur and zirconium is 0.5~2:1, obtained colloidal sol continues in 30~40 DEG C of constant temperature 1~2d is stirred, mixed liquor is transferred in stainless steel hydrothermal reaction kettle, 1~4d of crystallization at 100~120 DEG C, it is solidifying to obtain white Glue, vacuum filtration are washed 6~10 times, and 80~100 DEG C of dryings 12~for 24 hours, products therefrom is obtained in 600 DEG C of 3~8h of constant temperature calcining Mesoporous material SO4 2-/ZrO2-SiO2；
(2) bisgallic acid position solid-carrying type ionic-liquid catalyst SO4 2-/ZrO2-SiO2The preparation of-IL：Using toluene as solvent, will walk Suddenly 1~3g mesoporous materials SO obtained by (1)4 2-/ZrO2-SiO2Respectively with 3- chloropropyl triethoxysilanes, the miaow of 2~3mmol Azoles and 1,3-propane sultone, which are uniformly mixed, is incorporated in 90~120 DEG C of 24~48h of reflux, then using dichloromethane as solvent, by gained The H of product and 2~3mmol2SO4React at room temperature 24~72h, be filtered, washed, dry after up to bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
Bisgallic acid position solid-carrying type ionic-liquid catalyst produced by the present invention is used for the application of biodiesel synthesis, specific to walk It is rapid as follows：
By vegetable fat and short chain alcohol with oleyl alcohol molar ratio 1:10~45 are added autoclave, add based on grease matter The bisgallic acid position solid-carrying type ionic-liquid catalyst of amount 1.5~10.5% reacts 1~6h at 110~160 DEG C, after reaction, It centrifuges out solid catalyst and continues cycling through utilization, gained reaction mixture stratification again, lower layer is glycerine and excessive Methanol, supernatant liquid are biodiesel and unreacted soybean oil, and biodiesel is evaporated under reduced pressure to after liquid separation.
Above-mentioned vegetable fat is any type of soybean oil, palm oil, rapeseed oil or cottonseed oil, and short chain alcohol is methanol, second One kind of alcohol or propyl alcohol.
The invention has the advantages that：
(1) the bisgallic acid position solid-carrying type ionic-liquid catalyst prepared by has excellent catalytic activity,Acid and Lewis acid synergistic effect can make biodiesel yield up to 97% or more；
(2) catalyst has regular meso-hole structure, is conducive to heat transfer and mass transfer；
(3) the easily separated recycling of catalyst is repeated and is utilized, and reduces pollution.
Specific implementation mode
The following examples are further illustrations of the invention, it is not intended to limit the scope of the present invention.
【Embodiment 1】
Mesoporous material SO4 2-/ZrO2-SiO2Synthesis：A concentration of 2mol/L of 58mL are added in the F127 of the MW=12600 of 1g HCl solution in, 40 DEG C are uniformly mixed, and the TMB of 4.6mL is added in above-mentioned solution, continue constant temperature and stir 3h, to above-mentioned TEOS, Zr (n-OBu) are sequentially added in reaction mixture4(NH4)2SO4Aqueous solution, the molar ratio of silicon and zirconium is 2:1, sulphur Molar ratio with zirconium is 1:1, obtained colloidal sol continues to stir 2d in 40 DEG C of constant temperature, and it is anti-that mixed liquor is transferred to stainless steel hydro-thermal It answers in kettle, crystallization 2d at 120 DEG C obtains white gels, and vacuum filtration is washed 8 times, and for 24 hours, products therefrom is in 600 for 100 DEG C of dryings DEG C constant temperature calcining 5h, obtains mesoporous material SO4 2-/ZrO2-SiO2；
Bisgallic acid position solid-carrying type ionic-liquid catalyst SO4 2-/ZrO2-SiO2The preparation of-IL：Using toluene as solvent, by step (1) the 1g mesoporous materials SO obtained by4 2-/ZrO2-SiO2Respectively with 3- chloropropyl triethoxysilanes, imidazoles and the 1,3- of 2mmol Propane sultone is uniformly mixed to be incorporated in 110 DEG C of reflux 48h, then using dichloromethane as solvent, by the H of products therefrom and 2mmol2SO4 React at room temperature 72h, be filtered, washed, dry after up to bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 91.56%, raw after recycling 5 times The yield of object diesel oil is 82.47%.
【Embodiment 2】
In the case where the preparation condition of catalyst is identical with embodiment 1, only by the silicon and zirconium in preparation method Molar ratio be changed to 1.5:1, obtain bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 94.78%, raw after recycling 5 times The yield of object diesel oil is 83.88%.
【Embodiment 3】
In the case where the preparation condition of catalyst is identical with embodiment 1, only by the silicon and zirconium in preparation method Molar ratio be changed to 1:1, obtain bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 97.03%, raw after recycling 5 times The yield of object diesel oil is 88.20%.
【Embodiment 4】
In the case where the preparation condition of catalyst is identical with embodiment 1, only by the silicon and zirconium in preparation method Molar ratio be changed to 0.5:1, obtain bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 93.88%, raw after recycling 5 times The yield of object diesel oil is 84.09%.
【Embodiment 5】
In the case where the preparation condition of catalyst is identical with embodiment 1, only by the sulphur and zirconium in preparation method Molar ratio be changed to 0.5:1, obtain bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 91.48%, raw after recycling 5 times The yield of object diesel oil is 82.79%.
【Embodiment 6】
In the case where the preparation condition of catalyst is identical with embodiment 1, only by the sulphur and zirconium in preparation method Molar ratio be changed to 1.5:1, obtain bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
It is added to 4g soybean oils and 4.4g methanol in the autoclave of 50mL, adds the above-mentioned SO of 0.15g4 2-/ ZrO2-SiO2- IL catalyst reacts 5h at 150 DEG C, and the yield of gained biodiesel is 96.53%, raw after recycling 5 times The yield of object diesel oil is 85.22%.

Claims (3)

1. a kind of preparation method of the bisgallic acid position solid-carrying type ionic-liquid catalyst of biodiesel synthesis, it is characterised in that including with Lower process,
(1) mesoporous material SO4 2-/ZrO2-SiO2Synthesis：A concentration of 2mol/L of 58mL are added in the F127 of the MW=12600 of 1g HCl solution in, 30~40 DEG C are uniformly mixed, and the TMB of 4.6mL is added in above-mentioned solution, continue constant temperature stirring 2~ 3h sequentially adds TEOS, Zr (n-OBu) into above-mentioned reaction mixture4(NH4)2SO4Aqueous solution, control rubbing for silicon and zirconium You are than being 0.5~2:1, the molar ratio of sulphur and zirconium is 0.5~2:1, obtained colloidal sol in 30~40 DEG C of constant temperature continue stirring 1~ Mixed liquor is transferred in stainless steel hydrothermal reaction kettle by 2d, 1~4d of crystallization at 100~120 DEG C, obtains white gels, and vacuum is taken out Filter is washed 6~10 times, and 80~100 DEG C of dryings 12~for 24 hours, products therefrom obtains mesoporous material in 600 DEG C of 3~8h of constant temperature calcining SO4 2-/ZrO2-SiO2；
(2) bisgallic acid position solid-carrying type ionic-liquid catalyst SO4 2-/ZrO2-SiO2The preparation of-IL：Using toluene as solvent, by step (1) 1~3g mesoporous materials SO obtained by4 2-/ZrO2-SiO2Respectively with 3- chloropropyl triethoxysilanes, the imidazoles of 2~3mmol It is uniformly mixed with 1,3-propane sultone and is incorporated in 90~120 DEG C of 24~48h of reflux, then using dichloromethane as solvent, gained is produced The H of object and 2~3mmol2SO4React at room temperature 24~72h, be filtered, washed, dry after up to bisgallic acid position solid-carrying type ionic liquid SO4 2-/ZrO2-SiO2-IL。
2. the catalyst that the preparation method of catalyst as described in claim 1 obtains is used for the work of catalytically synthesizing biological diesel oil Skill, it is characterised in that including following procedure：
By vegetable oil and short chain alcohol with oleyl alcohol molar ratio 1:10~45 are added autoclave, add based on plant oil quality 1.5~10.5% bisgallic acid position solid-carrying type ionic-liquid catalyst reacts 1~6h at 110~160 DEG C, after reaction, from The heart isolates solid catalyst and continues cycling through utilization, and stratification, lower layer are glycerine and excessive first to gained reaction mixture again Alcohol, supernatant liquid are biodiesel and unreacted soybean oil, and biodiesel is evaporated under reduced pressure to after liquid separation.
3. the technique of catalytically synthesizing biological diesel oil according to claim 2, which is characterized in that vegetable oil is soybean oil, palm fibre Any type of palmitic acid oil, rapeseed oil or cottonseed oil, short chain alcohol is one kind of methanol, ethyl alcohol or propyl alcohol.
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