CN105419952B - A kind of method of biodiesel synthesis in eutectic system - Google Patents
A kind of method of biodiesel synthesis in eutectic system Download PDFInfo
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- CN105419952B CN105419952B CN201510895001.1A CN201510895001A CN105419952B CN 105419952 B CN105419952 B CN 105419952B CN 201510895001 A CN201510895001 A CN 201510895001A CN 105419952 B CN105419952 B CN 105419952B
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- eutectic
- biodiesel
- eutectic system
- sulfonic acid
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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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- 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)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of methods of biodiesel synthesis in eutectic system.Raw material is vegetable oil, methanol, and in N- propyl sulfonic acid-N, N, N- trihydroxy ethyl ammonium/glycerol composition eutectic system, agitating and heating obtains biodiesel under normal pressure.Advantage of the present invention are as follows: (1) sodium hydroxide catalyst is used, it is low in cost, catalytic activity is high, dosage is few；(2) reaction condition is mild, can react under the conditions of normal pressure, methanolic reflux temperature；(3) formed eutectic solvent, eliminates emulsion, simplifies process flow；(4) product purity is high, and impurity is few；(5) the eutectic catalyst system of eutectic solvent and sodium hydroxide composition, easily recycles, and is halogen-free ion in system, safe and reliable to environment, metal equipment.
Description
One technical field
The present invention relates to the methods of biodiesel synthesis in eutectic system, belong to technical field of chemical material preparation.This
Method is suitable for using vegetable oil, methanol as raw material, the occasion of biodiesel synthesis.
Two background techniques
As a kind of novel renewable and clean energy resource, biodiesel is with oil plants such as oil crops, oil palm and Chinese pistaches
The oil plants such as forest fruit, engineering microalgae water plant and animal fat, biodiesel etc. are liquid fuel made of raw material, are
Good petroleum diesel substitute.Biodiesel is typical " green energy resource ", greatly develops biodiesel and sends out Economic Sustainability
Exhibition promotes energy substitution, mitigates environmental pressure, and control urban atmospheric pollution has important strategic importance.
Biodiesel synthesis is the soda acid ester exchange reaction that can be catalyzed, generally use strong acid (sulfuric acid) or highly basic (KOH with
NaOH) make catalyst, it is strong there is catalytic erosion and be not readily separated after reacting recycling or product reaction process and after
Processing stage is easy saponification, generates a large amount of waste water, and the discharge of salkali waste (acid) liquid is easy the disadvantages of causing secondary pollution to environment.Cause
This, eliminating saponification phenomenon becomes the task of top priority of biodiesel large-scale application with the discharge for reducing spent acid salkali waste.
The physicochemical properties and ionic liquid extremely phase of eutectic solvent (Deep Eutectic Solvents, DESs)
Seemingly, therefore also it is classified as a kind of novel ion liquid by someone.Eutectic solvent is usually the quaternary ammonium by certain stoichiometric ratio
The eutectic mixture that salt and hydrogen-bond donor (such as amide, carboxylic acid and polyalcohol compound) are composed.As a kind of novel
Green solvent aroused widespread concern at present, be a kind of environmentally friendly material be also current Green Chemistry
One of Hot Contents of research field (J M DeSimone.For recent reviews.Science, 2002,297:
799.), eutectic solvent has many advantages, such as low melting point, selective dissolution power, low volatility, high thermal stability, designability.
In recent years, eutectic is tied up in biodiesel preparation and is also gradually applied, and choline chloride/glycerol is eutectic
Molten solvent can be used for the processes such as post-processing, the separating-purifying in biodiesel preparation, in the case where yield is unaffected, base
Originally the emulsion in postprocessing working procedures is eliminated.
Three summary of the invention
Phenomenon, product is easily separated, product is pure without being saponified for mild, reaction process that the purpose of the present invention is to provide reaction conditions
Degree is high, is halogen-free ion in entire reaction system and the side of biodiesel synthesis that catalyst system can recycle
Method.
The technical solution for realizing the aim of the invention is as follows: a kind of novel preparation method of biodiesel is with sodium hydroxide
Catalyst, in the eutectic solvent of N- propyl sulfonic acid-N, N, N- trihydroxy ethyl ammonium and glycerol composition, by vegetable oil, methanol
Heating stirring obtains biodiesel under normal pressure.
The method that biodiesel is prepared in a kind of eutectic system of the present invention, concrete measure is to be with sodium hydroxide
Catalyst, the eutectic solvent of N- propyl sulfonic acid-N, N, N- trihydroxy ethyl ammonium and glycerol composition, vegetable oil, methanol are raw material,
It is heated to reflux under normal pressure 2-4 hours and obtains biodiesel；Supercooling forms liquid-liquid two-phase system to room temperature after completion of the reaction,
Upper layer is crude product, and lower layer is eutectic system, the crude product that liquid separation obtains washed, dry after obtain biodiesel oil product；
Contain the complete raw material of unreacted, catalyst, by-product glycerin in lower layer's eutectic system, can be recycled and reuses.
Vegetable oil used in the present invention can be cottonseed oil, genetically engineered soybean oil, castor oil etc..
The molar ratio of N- propyl sulfonic acid-N, N, N- trihydroxy ethyl ammonium and glycerol is 1: 1.0 in eutectic system of the present invention
~3.0, wherein it is preferred that 1: 1.0~1.5.
The molar ratio of material used in the present invention is vegetable oil: methanol :=1: 3~8, wherein it is preferred that 1: 4~6.
Used catalyst dosage of the present invention is the 0.5~5% of plant oil quality, wherein it is preferred that 1；0.8~1.5%.
Eutectic system dosage (the sum of N- propyl sulfonic acid-N, N, N- trihydroxy ethyl ammonium and qualities of glycerin) of the present invention
It is the 5~15% of plant oil quality, wherein it is preferred that 8~10%；The material, catalyst proportionally feed intake mixing.
Vegetable oil used in the present invention, catalyst, eutectic solvent are commercial sources, and directly purchase uses.
The eutectic solvent of N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium of the present invention and glycerol composition, without prior
It is prefabricated, homogeneous transparent liquid is automatically formed in system after the reaction that feeds intake.
Vegetable oil used in the present invention, catalyst sodium hydroxide, methanol etc. are commercial sources, and directly purchase uses.Institute
N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium can directly buy commercially available reagent or bibliography self-control (Industrial&
Engineering Chemistry Research.2006,45 (24): 7982-7984).
Chemical principle is as follows based on the present invention:
In formula, R is the carbochain of fatty acid in vegetable oil.
A kind of preparation method of the biodiesel provided according to the present invention, key problem in technology are to use sodium hydroxide for catalysis
Agent, in the eutectic solvent of N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium and glycerol composition, by vegetable oil, methanol in normal pressure
Lower heating stirring obtains biodiesel.
Beneficial effect
(1) sodium hydroxide used in the present invention is catalyst, and N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium forms low with glycerol
Eutectic system can accommodate the by-product glycerin that reaction generates, and be rapidly separated it with biodiesel product, therefore reaction process
In, reaction balance can be promoted to carry out to the line of production, the effect of concerted catalysis can be played.
It (2) is inducer using N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium, existing hydrogen bond donor in structure also has hydrogen
Key receptor acts on simultaneously with glycerol, acts synergistically, and two kinds of substances can provide 1 hydrogen bond receptor center, in 2 hydrogen bond donors
The heart obtains novel eutectic system, and compared with betaine type eutectic system, eutectic of the invention ties up to acid, alkali environment
Middle tolerance is high, will not decompose in air or moisture.
(3) compared with the low donor system that traditional choline chloride or other quaternary ammonium halides form, the present invention is provided
Eutectic substance whole system in not halogens such as chloride ion-containing, it is safe and reliable to metal equipment especially stainless steel equipment, can
It is very stable to acid, alkali to be resistant to prolonged heating, it is suitable for industrialization and generates.
(4) present invention can be primary by all raw materials without preformed catalyst without prefabricated eutectic agent (DES)
Property be added reaction kettle in, it is only necessary to 2 steps for whole operation: (1) synthetic reaction；(2) it washes, is dry, technology achieved
Effect is to simplify the technological process of production, reduces the investment of equipment and cost, improves production efficiency.
(5) the method equipment of eutectic system biodiesel synthesis provided by the invention is simple, process flow is less, rear to locate
Reason is convenient, without complicated separating-purifying；Cost of material is low, from a wealth of sources；Organic solvent is not used in reaction process, product is pure
Degree is high, greatly reduces three waste discharge, is suitble to environmental-friendly chemical process.
Four specific embodiments
The present invention will be further described for the following examples, and the purpose is to can be best understood from the contents of the present invention.But
It is that embodiment does not limit the scope of the invention in any way.The technical staff of this professional domain is in scope of the invention as claimed
The modifications and adaptations inside made also should belong to right and protection scope of the invention.
Embodiment 1
In the three neck round bottom flask of 100mL, 2.24g N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added, 0.76g is sweet
Oily (molar ratio 1: 1), 30g (0.034mol) soybean oil (average molecular weight 878.25) heat 10 minutes under 65 DEG C of water-baths
(viscosity for reducing vegetable oil), adds 0.3g (0.0075mol) NaOH, 6g methanol (0.1875mol), normal pressure under 65 DEG C of water-baths
It is stirred at reflux reaction 4.0 hours, is cooled to room temperature, is transferred to separatory funnel layering (rapidly layering), lower layer is excessive methanol, sweet
Oil, eutectic solvent, NaOH mixture；Upper layer is product, after hot water washs 3~5 times, 400Pa, is dried in vacuo at 80 DEG C
Net product 25.7g is obtained, yield is about 85%.
Embodiment 2
In the three neck round bottom flask of 100mL, 2.98gN- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added, 1.52g is sweet
Oily (molar ratio 1: 1), 30g (0.034mol) soybean oil (average molecular weight 878.25) heat 10 minutes under 65 DEG C of water-baths, then
The NaOH of addition 0.15g, 8.7g methanol (0.27mol), 4.5g eutectic solvent (N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium/
Glycerine molar ratio is 1: 1.5), atmospheric agitation back flow reaction 2.0 hours, is cooled to room temperature, is transferred to liquid separation under 65 DEG C of water-baths
Funnel layering (layering rapidly), lower layer are the mixture of excessive methanol, glycerol, eutectic solvent, NaOH；Upper layer is product, warp
After hot water washs 3~5 times, 400Pa, vacuum drying obtains net product 26.0g at 80 DEG C, and yield is about 86%.
Embodiment 3
In the three neck round bottom flask of 100mL, 1.98g N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added, 2.02g is sweet
Oily (molar ratio 1: 3), 30g soybean oil (average molecular weight 878.25) heat 10 minutes under 65 DEG C of water-baths, add 1.5g's
NaOH, 8g methanol, atmospheric agitation back flow reaction 3.0 hours, is cooled to room temperature under 65 DEG C of water-baths, is transferred to separatory funnel layering
(layering rapidly), lower layer are the mixture of excessive methanol, glycerol, eutectic solvent, NaOH；Upper layer is product, through hot water washing 3
After~5 times, 400Pa, vacuum drying obtains net product 26.6g at 80 DEG C, and yield is about 88%.
Embodiment 4
In the three neck round bottom flask of 100mL, 0.89gN- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium, 0.61g third is added
Triol (molar ratio 1: 2), 30g soybean oil (average molecular weight 878.25) are heated 10 minutes under 65 DEG C of water-baths, are added
0.4gNaOH, 3.27g methanol, atmospheric agitation back flow reaction 4.0 hours, is cooled to room temperature under 65 DEG C of water-baths, is transferred to liquid separation leakage
Bucket layering (layering rapidly), lower layer are the mixture of excessive methanol, glycerol, eutectic solvent, NaOH；Upper layer is product, through heat
After water washing 3~5 times, 400Pa, vacuum drying obtains net product 24.2g at 80 DEG C, and yield is about 80%.
Embodiment 5
In the three neck round bottom flask of 100mL, 2.39g N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added, 0.81g is sweet
Oily (molar ratio 1: 1), 31.9g (0.034mol) castor oil (average molecular weight 933.44) heat 10 minutes under 65 DEG C of water-baths,
0.3g (0.0075mol) NaOH, 6g methanol (0.1875mol) is added, atmospheric agitation back flow reaction 4.0 is small under 65 DEG C of water-baths
When, be cooled to room temperature, be transferred to separatory funnel layering (rapidly layering), lower layer be excessive methanol, glycerol, eutectic solvent,
The mixture of NaOH；Upper layer is product, and after hot water washs 3~5 times, 400Pa, vacuum drying obtains net product at 80 DEG C
28.2g, yield are about 85%.
Embodiment 6
In the three neck round bottom flask of 100mL, 1.99g N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added, 1.01g is sweet
Oily (molar ratio 1: 1.5), 29.5g (0.034mol) cottonseed oil (average molecular weight 865.5) heat 10 points under 65 DEG C of water-baths
Clock adds 0.3g (0.0075mol) NaOH, 6g methanol (0.1875mol), and reaction 4.0 hours is stirred at reflux under 65 DEG C of water-baths,
It is cooled to room temperature, is transferred to separatory funnel layering (layering rapidly), lower layer is excessive methanol, glycerol, eutectic solvent, NaOH
Mixture；Upper layer is product, and after hot water washs 3~5 times, 400Pa, vacuum drying obtains net product 25.7g, yield at 80 DEG C
About 85%.
Embodiment 7
In the three neck round bottom flask of 1000mL, 17.87g N- propyl sulfonic acid-N, N, N- trihydroxyethyl ammonium is added,
12.13g glycerol (molar ratio 1: 2), 300g (0.34mol) soybean oil (average molecular weight 878.25), is heated under 65 DEG C of water-baths
10 minutes, add 3g (0.075mol) NaOH, 60g methanol (1.875mol), atmospheric agitation back flow reaction 4.0 under 65 DEG C of water-baths
Hour, be cooled to room temperature, be transferred to separatory funnel layering (rapidly layering), lower layer be excessive methanol, glycerol, eutectic solvent,
The mixture of NaOH；Upper layer is product, and after hot water washs 3~5 times, 400Pa, vacuum drying obtains net product at 80 DEG C
258g, yield are about 86%.
Embodiment 8
In the three neck round bottom flask of 100mL, 30g (0.034mol) soybean oil (average molecular weight 878.25) is added in 65
It is preheated 10 minutes under DEG C water-bath, after adding 0.3g (0.0075mol) NaOH, 6g methanol (0.1875mol) and embodiment 1
Eutectic-the catalyst system for the lower layer that liquid separation separates and recovers in treatment process, remaining operation obtain pure production with embodiment 1
Product 25.7g, yield are about 85%.
Claims (4)
1. a kind of method of biodiesel synthesis in eutectic system, it is characterised in that: using sodium hydroxide as catalyst, N- sulfonic acid
The eutectic system of propyl-N, N, N- trihydroxy ethyl ammonium and glycerol composition, vegetable oil, methanol are raw material, are heated under normal pressure
Reflux obtains biodiesel for 2-4 hours, and material used is disposably to feed intake；Supercooling forms liquid-to room temperature after completion of the reaction
Liquid two-phase system, upper layer are crude products, and lower layer is eutectic system, the crude product that liquid separation obtains washed, dry after given birth to
Object diesel product；Contain the complete raw material of unreacted, catalyst, by-product glycerin in lower layer's eutectic system, it is recyclable to lay equal stress on
It is multiple to use；
The preparation reaction of biodiesel is as follows:
In formula, R is the carbochain of fatty acid in vegetable oil；Wherein, vegetable oil is castor oil, genetically engineered soybean oil, cottonseed oil.
2. the method for biodiesel synthesis in a kind of eutectic system according to claim 1, it is characterised in that: composition is low
N- propyl sulfonic acid-N, N, N- the trihydroxy ethyl ammonium of eutectic system and the molar ratio of glycerol are 1: n, n=1.0~3.0.
3. the method for biodiesel synthesis in a kind of eutectic system according to claim 1, it is characterised in that: object used
The molar ratio of material is vegetable oil: methanol :=1: n, n=3~8, and catalyst amount is the 0.5~5% of plant oil quality, eutectic
System dosage is the 5~15% of plant oil quality, wherein eutectic system dosage refers to N- propyl sulfonic acid-N, N, N- trihydroxy
The sum of ethyl ammonium and qualities of glycerin, the material, catalyst proportionally feed intake mixing.
4. the method for biodiesel synthesis in a kind of eutectic system according to claim 1, it is characterised in that: N- sulfonic acid
The eutectic solvent of propyl-N, N, N- trihydroxy ethyl ammonium and glycerol composition, without prefabricated in advance, after the reaction that feeds intake in system
Automatically form homogeneous transparent liquid.
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| CN108950091B (en) * | 2018-07-31 | 2021-12-03 | 河北科技大学 | Eutectic solvent, preparation method thereof and application of eutectic solvent in preparation of glucose by hydrolyzing cellulose |
| CN110105619B (en) * | 2019-04-26 | 2020-12-25 | 中国科学院山西煤炭化学研究所 | Controllable degradation recovery method of polyurethane |
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| CN101058552A (en) * | 2006-04-18 | 2007-10-24 | 上海师范大学 | Double-functional group ionic liquid and preparation method |
| CN103525562A (en) * | 2013-10-25 | 2014-01-22 | 常州大学 | Method for preparing biodiesel through inducing eutectic system on site |
| CN103525561A (en) * | 2013-10-12 | 2014-01-22 | 盐城师范学院 | Method for preparing biodiesel in eutectic system |
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| CN101058552A (en) * | 2006-04-18 | 2007-10-24 | 上海师范大学 | Double-functional group ionic liquid and preparation method |
| CN103525561A (en) * | 2013-10-12 | 2014-01-22 | 盐城师范学院 | Method for preparing biodiesel in eutectic system |
| CN103525562A (en) * | 2013-10-25 | 2014-01-22 | 常州大学 | Method for preparing biodiesel through inducing eutectic system on site |
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