CN105754718B - A kind of preparation method of biodiesel - Google Patents
A kind of preparation method of biodiesel Download PDFInfo
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- CN105754718B CN105754718B CN201610261254.8A CN201610261254A CN105754718B CN 105754718 B CN105754718 B CN 105754718B CN 201610261254 A CN201610261254 A CN 201610261254A CN 105754718 B CN105754718 B CN 105754718B
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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
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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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
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- 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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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation methods of biodiesel, using laboratory self-control heteropoly acid Cr-Anderson as catalyst, using vegetable oil and methanol as raw material, under normal pressure, it is heated to reflux biodiesel synthesis, specifically includes the following steps: heteropolyacid catalyst is added in three-necked flask, then deionized water heating stirring is added, it is completely dissolved to catalyst, methanol is added, stirs 1 hour at 60-90 DEG C, then the vegetable oil for being preheated to 60-90 DEG C is added in mixed system, back flow reaction 3-8 hours to get biodiesel；Vegetable oil be any one of Rice oil, soybean oil, corn oil, sunflower oil, cottonseed oil, peanut oil, vegetable oil, methanol molar ratio be 1:6-20, catalyst amount be plant oil quality 0.5-5%；Present invention process is simple, and reaction condition is mild, high production efficiency, stable product quality, can obtain good economic benefit and environmental pollution.
Description
[technical field]
The invention belongs to renewable energy green preparation technical field, specifically a kind of preparation side of biodiesel
Method.
[background technique]
Biodiesel is a kind of mixed aliphatic ester, usually using animal and plant grease and waste grease etc. as raw material,
The product of ester exchange reaction is carried out with alcohol compound under catalysts conditions.The raw material for producing biodiesel in the world mainly wraps
It includes rapeseed oil, soybean oil, palm fibre and puts the vegetable fat such as oil, sunflower oil and civilian and industrial waste grease.
From the point of view of energy security and environmental protection, the energy that development can substitute petroleum is extremely important；The world is each
State all using Renewable Energy Development as energy supply anxiety is alleviated, copes with the important act of climate warming (reduction of greenhouse gas discharge)
It arranges；Compared with various other renewable energy (water energy, wind energy, geothermal energy, solar energy etc.), bio-fuel in addition to cleaning and can be again
Raw outer, it is the energy products that currently the only one kind directly could be produced and be substituted on a large scale transport fuel, has offer concurrently
The function of the energy and materiality production (biobased products), moreover it is possible to using pollutant or organic waste as raw material, realize resource
It recycles and is combined with environmental protection.
Alternative fuel of the biodiesel as petrifaction diesel, have with physical property similar in petrifaction diesel, and biology
The sulfur content of diesel oil is very low, nontoxic to environment, therefore referred to as environmentally friendly fuel.Compared with petrifaction diesel, biology
Diesel oil, which has the advantage that, is mainly reflected in the following aspects: (1) reproducibility；(2) good environmental protection characteristic；It (3) can biology
Degradation；(4) security performance is high；(5) preferable greasy property；(6) good combustion characteristics；(7) biodiesel and petrifaction diesel
Physicochemical property and service performance be it is very similar, under the premise of diesel engine is not transformed, can directly substitute petrifaction diesel makes
With, or with a certain ratio and petrifaction diesel blending use.Therefore, biodiesel is considered as a kind of important petrifaction diesel
Alternative fuel.
Heteropoly acid is a kind of to carry out Spatial Coupling by oxygen atom bridging mode by center hetero atom and coordination polyatom
Multi-oxygen cluster metal complex has highly acid, is a kind of green catalyst.Heteropoly acid usually has catalytic activity high, selective
It is good, nontoxic, do not corrode the advantages that equipment.Heteropoly acid is also shown good as acid catalyst in catalytically synthesizing biological diesel oil
Catalytic performance.
[summary of the invention]
A kind of preparation method of biodiesel is provided present invention aim to solve above-mentioned deficiency, not only technique
Simply, easy to operate, reaction condition is mild, and high production efficiency, stable product quality, can obtain good economic effect
Benefit, and can be reduced environmental pollution.
A kind of preparation method of biodiesel is provided to achieve the above object, and heteropoly acid Cr- is made by oneself with laboratory
Anderson is catalyst, using vegetable oil and methanol as raw material, under normal pressure, is heated to reflux biodiesel synthesis.
The vegetable oil is Rice oil, soybean oil, corn oil, sunflower oil, cottonseed oil, any one in peanut oil.
The vegetable oil, methanol molar ratio be vegetable oil: methanol=1:6-20, the catalyst amount be plant oil
The 0.5-5% of amount.
The time of above-mentioned heating reflux reaction is 1-10h.
The temperature of above-mentioned reaction is 60-90 DEG C.
The preparation method is specifically includes the following steps: heteropolyacid catalyst is added in three-necked flask, and then addition is gone
Ionized water heating stirring, is completely dissolved to catalyst, adds methanol, stirs 1 hour at 60-90 DEG C, then will be preheated to
60-90 DEG C of vegetable oil is added in mixed system, and back flow reaction 3-8 hours to get biodiesel.
It is further comprising the steps of: after the completion of back flow reaction, to be cooled to room temperature, be transferred to standing liquid separation 3-5 in separatory funnel
Hour, upper layer crude biodiesel is subjected to revolving and removes excessive methanol, is then washed 3-5 times with suitable deionized water,
The impurity such as a small amount of glycerol are removed, finally rotates again and removes moisture a small amount of in product, anhydrous calcium chloride is added, essence is obtained by filtration
Biodiesel processed.
The catalyst heteropoly acid Cr-Anderso is [(C4Hg)4N5]{H7[HOCH2C(CH2)3(CrO6)Mo6O18]2, it is described
The preparation method of catalyst heteropoly acid Cr-Anderson is the following steps are included: by Na3[Cr(OH)6Mo6O18] it is dissolved in deionization
In water, then heating stirring, reflux is added pentaerythrite, is heated to reflux 3h, rotate remove solvent after reaction, dry
To red powder；Obtained red powder is dissolved in deionized water again, heating stirring, tetrabutylammonium, flask bottom is then added
Portion obtains a large amount of red catalyst, as catalyst heteropoly acid Cr-Anderson.
The present invention compared with the existing technology, has the advantages that
(1) catalyst is done using laboratory self-control heteropoly acid, it is a kind of green catalyst which, which has highly acid,
Have many advantages, such as that catalytic activity is high, selectivity is good, nontoxic, does not corrode equipment；
(2) saponification problems for making catalyst generation of alkali are avoided, do not need to carry out at dehydration raw material before simultaneous reactions
Reason；
(3) reaction condition is mild, can react under the conditions of methanol eddy；
(4) simple process, easy to operate, high production efficiency, stable product quality can obtain good economic benefit,
The advantages of can be reduced environmental pollution again.
[specific embodiment]
The present invention provides a kind of preparation methods of biodiesel, are to urge with laboratory self-control heteropoly acid Cr-Anderson
Agent under normal pressure, is heated to reflux biodiesel synthesis using vegetable oil and methanol as raw material.Its specific preparation step are as follows: will be miscellaneous
Polyacid catalyst is added in three-necked flask, and deionized water heating stirring is then added, is completely dissolved to catalyst, adds first
Alcohol is stirred 1 hour at 60-90 DEG C, then the vegetable oil for being preheated to 60-90 DEG C is added in mixed system, back flow reaction
3-8 hours to get biodiesel.
It is further comprising the steps of: after the completion of back flow reaction, to be cooled to room temperature, be transferred to standing liquid separation 3-5 in separatory funnel
Hour, upper layer crude biodiesel is subjected to revolving and removes excessive methanol, is then washed 3-5 times with suitable deionized water,
The impurity such as a small amount of glycerol are removed, finally rotates again and removes moisture a small amount of in product, anhydrous calcium chloride is added, essence is obtained by filtration
Biodiesel processed.
Wherein, vegetable oil used is Rice oil, soybean oil, corn oil, sunflower oil, cottonseed oil, appointing in peanut oil
It anticipates one kind；The molar ratio of the vegetable oil, methanol is vegetable oil: methanol=1:6-20, and catalyst amount is plant oil quality
0.5-5%, proportionally feed intake mixing；Catalyst heteropoly acid Cr-Anderson used does not dissolve in methanol, but water
Dissolubility is fine, so suitable deionized water dissolving catalyst is first added before reaction, methanol is then added；The time of reaction is 1-
10h, the temperature of reaction are 60-90 DEG C.Catalyst heteropoly acid Cr-Anderson used is [(C4Hg)4N5]{H7[HOCH2C
(CH2)3(CrO6)Mo6O18]2, the preparation method comprises the following steps: by the Na of 8.9g3[Cr(OH)6Mo6O18] it is dissolved in the deionized water of 50ml
In, then heating stirring, reflux is added 2g pentaerythrite, is heated to reflux 3h, rotate remove solvent after reaction, dry
To red powder；Obtained red powder is dissolved in the deionized water of 50ml, heating stirring, 10g tetrabutylammonium is then added,
It is heteropoly acid Cr-Anderson that drag, which obtains a large amount of red catalyst,.
The preparation method of biodiesel provided by the present invention is made combined with specific embodiments below further explained below:
Embodiment 1
By taking Rice oil as an example.
Take the heteropoly acid (mass ratio 1%) of 0.92g to be added in 250ml three-necked flask, then be added 10ml go from
Sub- water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:9) of 38ml is then added, and it is small that 1 is stirred at 65 DEG C
When, then the 100ml Rice oil for being preheated to 65 DEG C is added in mixed system, back flow reaction 3 hours.It cools down after reaction
It to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, it is excessive that upper layer crude biodiesel is rotated to removing at 60 DEG C
Then methanol uses the deionized water cleaning product of 30ml, repeat 3~5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Revolving removes moisture a small amount of in product, and anhydrous calcium chloride is added, refining rice oil biodiesel is obtained by filtration.After measured, it produces
Rate is 92.5%.
Embodiment 2
By taking soybean oil as an example.
It takes the heteropoly acid (mass ratio 1.5%) of 1.38g to be added in 250ml three-necked flask, going for 10ml is then added
Ionized water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:12) of 50ml is then added, stirs at 60 DEG C
1 hour, then the 100ml soybean oil for being preheated to 60 DEG C is added in mixed system, back flow reaction 5 hours.After reaction
It is cooled to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, upper layer crude biodiesel is rotated at 60 DEG C and was removed
Then the methanol of amount uses the deionized water cleaning product of 30ml, repeat 3-5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Moisture a small amount of in product is evaporated off in backspin, and anhydrous calcium chloride is added, Refined Soybean oil biodiesel is obtained by filtration.After measured,
Yield is 87.3%.
Embodiment 3
By taking peanut oil as an example.
Take the heteropoly acid (mass ratio 2%) of 1.84g to be added in 250ml three-necked flask, then be added 10ml go from
Sub- water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:15) of 63ml is then added, stirs 1 at 70 DEG C
Hour, then the 100ml peanut oil for being preheated to 70 DEG C is added in mixed system, back flow reaction 6 hours.It is cold after reaction
But it to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, it is excessive that upper layer crude biodiesel is rotated to removing at 60 DEG C
Methanol, then use 30ml deionized water cleaning product, repeat 3-5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Revolving removes moisture a small amount of in product, and anhydrous calcium chloride is added, and purification peanut oil biodiesel is obtained by filtration.After measured, it produces
Rate is 90.6%.
Embodiment 4
By taking corn oil as an example.
It takes the heteropoly acid (mass ratio 2.5%) of 2.30g to be added in 250ml three-necked flask, going for 10ml is then added
Ionized water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:20) of 84ml is then added, stirs at 80 DEG C
1 hour, then the 100ml corn oil for being preheated to 80 DEG C is added in mixed system, back flow reaction 8 hours.After reaction
It is cooled to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, upper layer crude biodiesel is rotated at 60 DEG C and was removed
Then the methanol of amount uses the deionized water cleaning product of 30ml, repeat 3-5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Moisture a small amount of in product is evaporated off in backspin, and anhydrous calcium chloride is added, refined maize oil biodiesel is obtained by filtration.After measured,
Yield is 96.2%.
Embodiment 5
By taking cottonseed oil as an example.
Take the heteropoly acid (mass ratio 1%) of 0.92g to be added in 250ml three-necked flask, then be added 10ml go from
Sub- water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:10) of 42ml is then added, stirs 1 at 75 DEG C
Hour, then the 100ml cottonseed oil for being preheated to 75 DEG C is added in mixed system, back flow reaction 5 hours.It is cold after reaction
But it to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, it is excessive that upper layer crude biodiesel is rotated to removing at 60 DEG C
Methanol, then use 30ml deionized water cleaning product, repeat 3-5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Revolving removes moisture a small amount of in product, and anhydrous calcium chloride is added, and purification cottonseed oil biodiesel is obtained by filtration.After measured, it produces
Rate is 85.7%.
Embodiment 6
By taking sunflower oil as an example.
Take the heteropoly acid (mass ratio 2%) of 1.84g to be added in 250ml three-necked flask, then be added 10ml go from
Sub- water heating stirring, is completely dissolved to catalyst, and the methanol (molar ratio 1:15) of 63ml is then added, stirs 1 at 90 DEG C
Hour, then the 100ml sunflower oil for being preheated to 90 DEG C is added in mixed system, back flow reaction 7 hours.After reaction
It is cooled to room temperature, is transferred in separatory funnel and stands liquid separation 3 hours, upper layer crude biodiesel is rotated at 60 DEG C and was removed
Then the methanol of amount uses the deionized water cleaning product of 30ml, repeat 3-5 times, the impurity such as a small amount of glycerol are removed, then at 80 DEG C
Moisture a small amount of in product is evaporated off in backspin, and anhydrous calcium chloride is added, and purification sunflower oil biodiesel is obtained by filtration.Through surveying
It is fixed, yield 76.8%.
The present invention is simultaneously not limited to the embodiments described above, other any without departing from spiritual essence and principle of the invention
Changes, modifications, substitutions, combinations, simplifications made by lower, should be equivalent substitute mode, are included in protection model of the invention
Within enclosing.
Claims (7)
1. a kind of preparation method of biodiesel, it is characterised in that: making heteropoly acid Cr-Anderson by oneself with laboratory is catalysis
Agent under normal pressure, is heated to reflux biodiesel synthesis using vegetable oil and methanol as raw material；The catalyst heteropoly acid Cr-
Anderson is [(C4Hg)4N5]{H7[HOCH2C(CH2)3(CrO6)Mo6O18]2, the catalyst heteropoly acid Cr-Anderson
Preparation method the following steps are included: by Na3[Cr(OH)6Mo6O18] be dissolved in deionized water, heating stirring, it flows back, then
Pentaerythrite is added, is heated to reflux 3h, revolving removes solvent after reaction, is dried to obtain red powder；It is red by what is obtained again
Color powder is dissolved in deionized water, heating stirring, and tetrabutylammonium is then added, and drag obtains a large amount of red catalyst, i.e.,
For catalyst heteropoly acid Cr-Anderson.
2. the preparation method of biodiesel as described in claim 1, it is characterised in that: the vegetable oil is Rice oil, soybean
Oil, corn oil, sunflower oil, cottonseed oil, any one in peanut oil.
3. the preparation method of biodiesel as described in claim 1, it is characterised in that: the molar ratio of the vegetable oil, methanol
For vegetable oil: methanol=1:6-20, the catalyst amount are the 0.5-5% of plant oil quality.
4. the preparation method of biodiesel as described in claim 1, it is characterised in that: the time of heating reflux reaction is 1-
10h。
5. the preparation method of biodiesel as described in claim 1, it is characterised in that: the temperature of reaction is 60-90 DEG C.
6. the preparation method of biodiesel as described in claim 1, which is characterized in that specifically includes the following steps: by miscellaneous more
Acid catalyst is added in three-necked flask, and deionized water heating stirring is then added, is completely dissolved to catalyst, adds first
Alcohol is stirred 1 hour at 60-90 DEG C, then the vegetable oil for being preheated to 60-90 DEG C is added in mixed system, back flow reaction
3-8 hours to get biodiesel.
7. the preparation method of biodiesel as claimed in claim 6, which is characterized in that further comprising the steps of: back flow reaction
After the completion, it is cooled to room temperature, is transferred in separatory funnel and stands liquid separation 3-5 hours, upper layer crude biodiesel is rotated
Excessive methanol is removed, is then washed 3-5 times with suitable deionized water, the impurity such as a small amount of glycerol is removed, finally rotates again
Moisture a small amount of in product is removed, anhydrous calcium chloride is added, refining biodiesel is obtained by filtration.
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| WO2008122790A2 (en) * | 2007-04-05 | 2008-10-16 | University Of York | Heteropolyacid catalysts and biodiesel manufacturing methods using such catalysts |
| CN101294094A (en) * | 2007-04-29 | 2008-10-29 | 华中农业大学 | Method for preparing biological diesel oil by using nano-solid heteropoly acid, heteropolybase catalyst |
| CN101294093B (en) * | 2007-04-29 | 2012-10-10 | 华中农业大学 | Integrated preparation method for biological diesel oil and isolated plant |
| JP5964327B2 (en) * | 2011-02-14 | 2016-08-03 | カウンスィル オブ サイエンティフィック アンド インダストリアル リサーチＣｏｕｎｃｉｌ Ｏｆ Ｓｃｉｅｎｔｉｆｉｃ ＆ Ｉｎｄｕｓｔｒｉａｌ Ｒｅｓｅａｒｃｈ | Improved process for producing fatty acid alkyl esters (biodiesel) from triglyceride oils by using environmentally friendly solid base catalysts |
| CN105080606A (en) * | 2014-05-06 | 2015-11-25 | 东北师范大学 | Polyoxometallate catalyst for preparing biodiesel |
| CN104907098B (en) * | 2015-04-21 | 2017-12-05 | 上海大学 | The co-based fischer-tropsch composite catalyst of metal polyacid, it is prepared and evaluation method |
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Effective date of registration: 20191212 Address after: No. 288, Jingfu village, Yuping Township, Pingjiang County, Yueyang City, Hunan Province Patentee after: Huang Huaming Address before: 200235 No. 120-121, Xuhui District, Shanghai, Caobao Road Patentee before: Shanghai Institute of Applied Technology |
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| TR01 | Transfer of patent right |