CN107866276A - A kind of polyacid site ion solid catalyst based on fatty amine and preparation method thereof - Google Patents
A kind of polyacid site ion solid catalyst based on fatty amine and preparation method thereof Download PDFInfo
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- CN107866276A CN107866276A CN201711106537.6A CN201711106537A CN107866276A CN 107866276 A CN107866276 A CN 107866276A CN 201711106537 A CN201711106537 A CN 201711106537A CN 107866276 A CN107866276 A CN 107866276A
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- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
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- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- 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
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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
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Abstract
The invention discloses a kind of polyacid site ion solid catalyst based on fatty amine and preparation method thereof, more amine aqueous solutions of certain mass fraction are formed in solvent by the way that the amine compound containing multiple amidos is dissolved in, again by the solution and 1,3 propane sultones or 1,4 butyl sultone one-step method are reacted, and are reacted after terminating through filtering, washing, dry obtained polyacid site ion solid catalyst.The catalyst acid site is more, catalytic activity is high, easily separated recovery, and its preparation method process is simple, operation is environmentally friendly, reaction condition is gentle, possesses the potentiality of large-scale production.Catalyst prepared by the present invention is used to achieve good effect in the production of biodiesel.
Description
Technical field
The present invention relates to a kind of catalysis material synthesis technical field, specifically a kind of polyacid site based on fatty amine
Ion solid catalyst and preparation method thereof.
Background technology
Biodiesel is a kind of renewable, nontoxic, low emission green fuel, be considered as conventional fossil fuel most have it is latent
The substitute of power, mainly it is made by esterification or animal and vegetable oil ester exchange reaction, its production process must add catalyst to carry
High efficiency.In view of importance of the catalyst in production of biodiesel, one is had become on its research at present
Focus.Up to the present, the catalyst of conventional production of biodiesel is homogeneous soda acid, solid acid-base and biology enzyme.But
Homogeneous acid catalyst such as concentrated sulfuric acid etc., although catalytic activity is high, the problems such as corrosivity is strong, seriously polluted be present.Inorganic base
Catalyst can cause the saponification of grease.The problem of catalytic activity is low and active component is easy to run off be present in solid acid-base.Biology
Enzymatic is although environment-friendly, but production cost is high, and the reaction raw materials such as short chain alcohol easily cause the inactivation of enzyme.
Ionic-liquid catalyst is referred to as because being received significant attention with designability, heat-flash stability, strong electric conductivity etc.
A kind of green catalyst.Generally, ionic liquid typically by alkyl imidazole, alkyl pyridine or fatty amine be parent by it is quaternized with
It is made again with organic acid or inorganic acid dissociation after sulfonation.
Chinese patent CN 101514292 discloses a kind of method that presence of acidic ionic liquid catalyst prepares biodiesel, with alkane
The sulfonic acid type ion liquid of base imidazoles, alkyl pyridine and fatty amine is that catalysis prepares micro-biodiesel, reactions steps in the technique
Complexity, and parent comprise only one can be with quaternized active nitrogen site, therefore sour site is less, and catalytic activity is relatively low, and
Using when the problem of larger equipment corrosion, ionic liquid dosage and difficult separation and recycling be present.
Chinese patent CN105132187 discloses a kind of for catalysis biological grease and methanol reaction preparation biodiesel
The preparation method of acidic ionic liquid catalysts, specifically dibromobutane is first reacted with parent morpholine to be formed with double-core nitrogen
The intermediate of avtive spot, then by carrying out sulfonic acid funtionalized with PS, finally carry out ion friendship with sulfuric acid again
Get final double-core sulfonic acid funtionalized ionic liquid in return.Although prepared catalyst has preferable performance, this method is deposited
It is complicated in process, it is longer the time required to acid dissociation, and prepared homogeneous catalyst separation be present with reclaiming the problem of difficult, from
And limit its large-scale application in the industry.
In summary, the conventional ion liquid catalyst for production of biodiesel, it is low and be difficult to point to generally there are activity
The shortcomings that from recovery.The former is due to the basic parent of most of ionic liquids（Alkyl imidazole, pyridine, tertiary amine）It can only provide
One avtive spot so that catalyst acid site is less, the latter be due to then the raw material that uses during production of biodiesel and
Final product is mostly liquid so that ionic-liquid catalyst is difficult the recovery that is separated from reaction system, so that can not the company of realization
Continuous production.So a kind of ion solid catalyst with polyacid site of production, raising for catalyst activity and its with production
The quick separating of thing, so as to realize that the continuous production of biodiesel seems extremely important.
The content of the invention
It is an object of the invention to provide a kind of polyacid site ion solid catalyst for catalysis for preparing biodiesel oil and
Its preparation method, to overcome the drawbacks described above of prior art, for catalysis for preparing biodiesel oil provide it is a kind of it is more green, efficient,
The big catalyst of prospects for commercial application.
Based on above-mentioned purpose, the following content of the invention is herein proposed：
A kind of polyacid site ion solid catalyst based on fatty amine, by polyamine compounds and group containing multiple sulfonic acid groups
Into its acid number is 1.03 ~ 1.95mmol/g.
When the catalyst is used to be catalyzed oleic acid and the reaction of methanol preparation biodiesel, yield is 85.32 ~ 99.34%.
A kind of preparation method of the polyacid site ion solid catalyst based on fatty amine：By the fatty amine containing multiple amidos
Compound is dissolved in more amine aqueous solutions that certain mass fraction is formed in organic solvent, then by the solution and PS or 1,
4- butyl sultone single step reactions, react after terminating through filtering, washing, dry obtained polyacid site ion solid catalyst.
Described reaction raw materials are polyamine compounds, it is preferable that can select ethylenediamine, propane diamine, butanediamine, penta 2
Amine, hexamethylene diamine, heptamethylene diamine, octamethylenediamine, diethylenetriamine, triethylene tetramine, TEPA and pentaethylene hexamine etc. are polyaminated
Compound；
The solvent can be water, ethanol, methanol, dimethyl sulfoxide (DMSO), acetone, acetonitrile, 1-METHYLPYRROLIDONE, N, N- dimethyl
The one kind therein such as formamide, DMA；
The mass fraction of more amine aqueous solutions is 1 ~ 100wt%；
The polyamines is 1 with the mol ratio of 1,3- propane sultones or 1,4- butyl sultones:1~1:10；
More amine aqueous solutions are 25 ~ 60 DEG C with the reaction temperature of 1,3- propane sultones or 1,4- butyl sultones；
The reaction time of more amine aqueous solutions and 1,3- propane sultones or 1,4- butyl sultones is 0.5 ~ 12h；
The drying temperature is 60 ~ 120 DEG C, and drying time is 6 ~ 12h.
The present invention is reaction raw materials from the fatty amine containing multiple amidos, with PS or Isosorbide-5-Nitrae-fourth sulfonic acid
Lactone in a mild condition, can be prepared by by a step sulfonation.With Chinese patent CN 101514292 disclosed in a kind of be based on alkane
The sulfonic acid type ion liquid phase ratio of base imidazoles, alkyl pyridine and fatty amine, due to the polyacid site based on fatty amine in the present invention
The preparation method of ion solid catalyst is simple, without acid dissociation, therefore the problem of equipment corrosion is not present in application, and institute
It is more that ion solid catalyst acid site is made, catalytic activity is high, and usage amount is small, and industrialization cost is relatively low.With Chinese patent
One kind disclosed in CN105132187 using morpholine as parent, by with dibromobutane, PS and sulfuric acid reaction system
The double-core sulfonic acid funtionalized ionic liquid obtained is compared, the polyacid site ion solid catalyst reaction based on fatty amine in the present invention
Time is short, and reaction system is easily separated and the easy recycling of catalyst, and industrial applications value is higher.In a word, with showing
There is ionic-liquid catalyst synthetic technology to compare, catalyst involved in the present invention is direct by one-step method under mild conditions
Synthesis, needs not move through acid dissociation and is formed, therefore this method has the advantages of process is simple, cost is cheap, green, made
Standby catalyst has sour site more and the advantages of easily separated recovery, and prospects for commercial application is wide.Meanwhile prepared using the present invention
Method, it can easily select property preferably ion solid catalyst by adjusting ion solid preparation technology.
Polyamines ion solid catalyst in polyacid site of the present invention is applied to oleic acid and methanol prepares biodiesel
Production in achieve good result.Not only catalytic activity is high during the course of the reaction but also is by simple process after the reaction
Recycling can be achieved, it is pollution-free, so as to greatly reduce the application cost of catalyst.
Specific implementation method
By embodiment in detail below, the invention will be further elaborated.
Embodiment 1
The methanol solution for the ethylenediamine that mass fraction is 5wt% is added dropwise in 1,3- propane sultones（Ethylenediamine and the sulphurs of 1,3- third
The mol ratio 1 of acid lactone:1）, 4h is reacted at 30 DEG C, reaction is washed after terminating through filtering, methanol, 60 DEG C of drying 12h, is obtained
Polyacid site ion solid catalyst, its acid number are 1.25mmol/g.
By methanol and oleic acid with molar ratio of alcohol to acid 10:1 adds reactor, adds above-mentioned ion solid catalyst, is catalyzed
Agent addition is the 2.0% of oleic acid quality, and reaction temperature is 60 DEG C, reacts 1 h, you can biodiesel crude product is obtained, then through subtracting
Separated methanol is pressed, obtains refined products biodiesel, biodiesel yield, biodiesel are calculated by gas chromatographic analysis
Yield is 90.95%.
Embodiment 2
By mass fraction be 10wt% diethylenetriamine acetonitrile solution dropwise into 1,3- propane sultones（Diethylenetriamine
With the mol ratio 1 of 1,3- propane sultones:2）, 2h is reacted at 40 DEG C, reaction is done after terminating through filtering, acetonitrile washing, 120 DEG C
Dry 6h processed, polyacid site ion solid catalyst is made, its acid number is 1.62mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, finally
Biodiesel yield is 96.56%.
Embodiment 3
The 1-METHYLPYRROLIDONE solution for the triethylene tetramine that mass fraction is 50wt% is added dropwise in 1,3- propane sultones
（The mol ratio 1 of triethylene tetramine and 1,3- propane sultones:3）, 3h is reacted at 30 DEG C, is reacted after terminating through filtering, N- first
The washing of base pyrrolidones, obtained polyacid site ion solid catalyst is dried, its acid number is 1.70 mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 97.71%.
Embodiment 4
The ethanol solution for the TEPA that mass fraction is 20wt% is added dropwise in 1,3- propane sultones（TEPA
With the mol ratio 1 of 1,3- propane sultones:4）, 0.5h is reacted at 60 DEG C, reaction is washed after terminating through filtering, ethanol, 60 DEG C
12h processed is dried, polyacid site ion solid catalyst is made, its acid number is 1.85mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 98.17%.
Embodiment 5
The acetone soln for the pentaethylene hexamine that mass fraction is 20wt% is added dropwise in 1,3- propane sultones（Pentaethylene hexamine
With the mol ratio 1 of 1,3- propane sultones:5）, 4h is reacted at 50 DEG C, reaction is done after terminating through filtering, acetone washing, 60 DEG C
Dry 12h processed, is made polyacid site ion solid catalyst, and its acid number is：1.95mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 99.34%.
Embodiment 6
The aqueous isopropanol for the propane diamine that mass fraction is 20wt% is added dropwise in 1,3- propane sultones（Propane diamine and 1,3-
The mol ratio 1 of propane sultone:6）, 5h is reacted at 40 DEG C, reaction is washed after terminating through filtering, isopropanol, 60 DEG C of dry systems
12h, is made polyacid site ion solid catalyst, and its acid number is：1.38mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 94.24%.
Embodiment 7
The N,N-dimethylformamide solution for the butanediamine that mass fraction is 20wt% is added dropwise in 1,3- propane sultones（Fourth
The mol ratio 1 of diamines and 1,3- propane sultones:7）, 12h is reacted at 25 DEG C, is reacted after terminating through filtering, N, N- dimethyl
Formamide washing, 60 DEG C of drying 12h, are made polyacid site ion solid catalyst, and its acid number is：1.32mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 93.53%.
Embodiment 8
The DMAC N,N' dimethyl acetamide solution for the pentanediamine that mass fraction is 10wt% is added dropwise in 1,3- propane sultone solution
（Pentanediamine and 1,3- propane sultones mol ratio 1:10）, 6h is reacted at 40 DEG C, is reacted after terminating through filtering, N, N- dimethyl
Acetamide washing, 60 DEG C of drying 12h, are made polyacid site ion solid catalyst, and its acid number is：1.26mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 92.32%.
Embodiment 9
The dimethyl sulphoxide solution for the hexamethylene diamine that mass fraction is 10wt% is added dropwise in PS solution（Oneself two
The mol ratio 1 of amine and PS:10）, 7h is reacted at 40 DEG C, reaction is washed after terminating through filtering, dimethyl sulfoxide (DMSO)
Wash, 60 DEG C of drying 12h, polyacid site ion solid catalyst is made, its acid number is：1.18mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 91.46%.
Embodiment 10
The ethanol solution for the heptamethylene diamine that mass fraction is 1wt% is added dropwise in PS solution（Heptamethylene diamine and 1,3-
The mol ratio 1 of propane sultone:10）, 4h is reacted at 40 DEG C, reaction is washed after terminating through filtering, ethanol, 60 DEG C of dry systems
12h, is made polyacid site ion solid catalyst, and its acid number is：1.10mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 89.32%.
Embodiment 11
The aqueous solution for the octamethylenediamine that mass fraction is 100wt% is added dropwise in Isosorbide-5-Nitrae-butyl sultone solution（Octamethylenediamine and Isosorbide-5-Nitrae-
The mol ratio 1 of butyl sultone:10）, 4h is reacted at 40 DEG C, reaction is dried through filtering, water washing, 60 DEG C after terminating and made
12h, is made polyacid site ion solid catalyst, and its acid number is：1.03mmol/g.
Prepared catalyst is used for oleic acid and prepares biodiesel with methanol, application conditions are same as Example 1, biology
Diesel yield is 85.32%.
In addition, by the above-mentioned used filtered recovery of catalyst, recycle under the same reaction conditions 6 times, this is urged
Agent still shows original catalytic activity, therefore the stability of the polyacid site ion solid catalyst is higher.
The result of above example shows, using the preparation method of the present invention, by controlling in catalyst preparation process
Various conditions, including fatty amine species, the species of solvent and its concentration, the temperature and time of reaction, can effectively be controlled made
The property of standby ion solid, and the ion solid catalyst with excellent catalytic performance can be therefrom selected, it is allowed to possess
The condition of large-scale application in terms of biodiesel is prepared.
The foregoing description of the disclosed embodiments, professional and technical personnel in the field are enable to realize or using the present invention.
A variety of modifications to these embodiments will be apparent for those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, it is of the invention
The embodiments shown herein is not intended to be limited to, and is to fit to and principles disclosed herein and features of novelty phase one
The most wide scope caused.
Claims (8)
- A kind of 1. polyacid site ion solid catalyst based on fatty amine, it is characterised in that：The catalyst is by containing multiple sulphurs The polyamine compounds composition of acid groups, its acid number is 1.03 ~ 1.95mmol/g.
- 2. a kind of preparation method of polyacid site ion solid catalyst based on fatty amine according to claim 1, its It is characterised by：Amine compound containing multiple amidos is dissolved in more amine aqueous solutions that certain mass fraction is formed in solvent, then will The solution reacts with PS or Isosorbide-5-Nitrae-butyl sultone one-step method, reacts after terminating through filtering, washing, dry system Obtain polyacid site ion solid catalyst.
- 3. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：The described amine compound containing multiple amidos includes ethylenediamine, propane diamine, butanediamine, pentanediamine, hexamethylene diamine, heptan Diamines, octamethylenediamine, diethylenetriamine, triethylene tetramine, TEPA and five secondOne or more in alkene hexamine.
- 4. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：Solvent includes water, ethanol, methanol, dimethyl sulfoxide (DMSO), acetone, acetonitrile, 1-METHYLPYRROLIDONE, N, N- dimethyl formyls One kind in amine, DMAC N,N' dimethyl acetamide.
- 5. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：The mass fraction of more amine aqueous solutions is 1 ~ 100wt%.
- 6. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：Polyamines is 1 with the mol ratio of 1,3- propane sultones or 1,4- butyl sultones:1~1:10.
- 7. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：More amine aqueous solutions are 25 ~ 60 DEG C with the reaction temperature of 1,3- propane sultones or 1,4- butyl sultones；Reaction time is 0.5~12h。
- 8. the preparation method of the polyacid site ion solid catalyst according to claim 2 based on fatty amine, its feature It is：Drying temperature is 60 ~ 120 DEG C, and drying time is 6 ~ 12h.
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| CN109174179A (en) * | 2018-08-21 | 2019-01-11 | 福州大学 | A kind of preparation method of self-curing ionic liquid |
| CN109847798A (en) * | 2019-03-15 | 2019-06-07 | 福州大学 | A kind of preparation method of solid type ionic-liquid catalyst |
| CN111001440A (en) * | 2019-12-26 | 2020-04-14 | 福州大学 | Polyacid site ionic liquid catalyst and preparation method and application thereof |
| CN112387308A (en) * | 2020-12-23 | 2021-02-23 | 福州大学 | Self-supporting solid acidic ionic liquid catalyst and preparation method thereof |
| CN116328741A (en) * | 2023-04-23 | 2023-06-27 | 福州大学 | Magnetic Hg 2+ Method for preparing adsorbent |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109174179A (en) * | 2018-08-21 | 2019-01-11 | 福州大学 | A kind of preparation method of self-curing ionic liquid |
| CN109847798A (en) * | 2019-03-15 | 2019-06-07 | 福州大学 | A kind of preparation method of solid type ionic-liquid catalyst |
| CN111001440A (en) * | 2019-12-26 | 2020-04-14 | 福州大学 | Polyacid site ionic liquid catalyst and preparation method and application thereof |
| CN112387308A (en) * | 2020-12-23 | 2021-02-23 | 福州大学 | Self-supporting solid acidic ionic liquid catalyst and preparation method thereof |
| CN116328741A (en) * | 2023-04-23 | 2023-06-27 | 福州大学 | Magnetic Hg 2+ Method for preparing adsorbent |
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