CN111500373B - Preparation method of biodiesel - Google Patents
Preparation method of biodiesel Download PDFInfo
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- CN111500373B CN111500373B CN202010343432.8A CN202010343432A CN111500373B CN 111500373 B CN111500373 B CN 111500373B CN 202010343432 A CN202010343432 A CN 202010343432A CN 111500373 B CN111500373 B CN 111500373B
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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
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
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- 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
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
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- 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
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- 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
- C11B3/16—Refining fats or fatty oils by mechanical means
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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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- 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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Abstract
The invention discloses a preparation method of biodiesel, which comprises the following steps: carrying out glycerol esterification reaction, ester exchange reaction, dealcoholization, sedimentation and methyl ester rectification on the raw material acidified oil to obtain BD100 biodiesel; the transesterification reaction process adopts calcium glyceroxide as a catalyst, calcium glyceroxide solid forms a calcium glyceroxide methanol solution through the processes of catalyst preparation, filtration and dissolution, and then is used for catalyzing the transesterification reaction process of the acidified oil, the regeneration of calcium oxide is further realized through the processes of dealcoholization, sedimentation, glycerol rectification and steam conversion, and the regenerated calcium oxide is reused in the catalyst preparation process; the method has the characteristics of low raw material requirement, wide application range, high product yield, no solid waste, wide source of the catalyst raw material, regeneration and reuse and the like, and is suitable for industrial production. The method of the invention can economically, green, efficiently and stably produce BD100 biodiesel.
Description
Technical Field
The invention belongs to the technical field of grease chemical industry, and particularly relates to a preparation method of biodiesel.
Background
Biodiesel oilThe fuel has the advantages of no pollution, biodegradability, good combustion performance and the like, and is a green energy source with wide application prospect. The acidified oil is one of the important raw materials of the existing biodiesel enterprises, usually contains a large amount of free fatty acid, and needs to be subjected to deacidification treatment and then prepared into the biodiesel by an alkali catalysis method. At present, the process of industrially preparing the biodiesel by taking the acidified oil as the raw material generally adopts concentrated H 2 SO 4 The catalytic esterification method is combined with a KOH (or NaOH) catalytic ester exchange method, and the two-step method has the problems of high acid value of sulfuric acid wastewater and esterification products, serious saponification side reaction, low yield of biodiesel products and the like.
The glycerol esterification deacidification method is a green and efficient deacidification method, and can well solve the problem that the acid value of sulfuric acid wastewater and esterification products is higher. Chinese patent CN205077009U, CN105623861B, CN105779139A, CN104694256A successively discloses relevant glycerol esterification reaction devices and processes, confirms the effectiveness and feasibility of the glycerol esterification deacidification method, and can reduce the loss of biodiesel products. Subsequently, chinese patent CN108330001B discloses a continuous glycerol esterification deacidification device, which realizes the continuity of the glycerol esterification deacidification process in a multi-kettle series connection mode, and the acid value can be below 1.0 mgKOH/g. Chinese patent CN108277090B further discloses a preparation method of low-sulfur biodiesel based on a glycerol esterification deacidification method, and the method can be used for producing high-grade biodiesel with the sulfur content of less than 10 ppm.
However, in the actual biodiesel production process, a small amount of free fatty acid (acid value of 1.0mgKOH/g is equivalent to 0.5% of residual fatty acid) still remains after the raw material acidified oil is subjected to acid reduction treatment by a glycerol esterification method, and in the subsequent ester exchange reaction, the free fatty acid is very easy to be subjected to saponification reaction with a KOH or NaOH catalyst, so that the problems of difficult separation of biodiesel from glycerol, reduction of the yield of biodiesel and glycerol, increase of the yield of asphalt, difficult regeneration of the catalyst and the like are caused.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, and provides a preparation method of biodiesel, which is particularly suitable for the process of producing biodiesel from acidified oil.
The preparation method of the biodiesel is characterized by comprising the following steps: carrying out glycerol esterification reaction, ester exchange reaction, dealcoholization, sedimentation and methyl ester rectification on the raw material acidified oil to obtain BD100 biodiesel; the transesterification reaction process adopts calcium glyceroxide as a catalyst, calcium glyceroxide solid forms a calcium glyceroxide methanol solution through the processes of catalyst preparation, filtration and dissolution, and then is used for catalyzing the transesterification reaction process of the acidified oil, the regeneration of calcium oxide is further realized through the processes of dealcoholization, sedimentation, glycerol rectification and steam conversion, and the regenerated calcium oxide is reused in the catalyst preparation process; wherein, the crude methanol distilled from the dealcoholization process is rectified and recovered by methanol to obtain refined methanol which is reused in the calcium glycerolysis process; the crude glycerol obtained by the settling procedure is rectified and recovered by glycerol to obtain refined glycerol which is then recycled in the glycerol esterification reaction procedure or the catalyst preparation procedure.
The preparation method of the biodiesel is characterized in that the acidified oil comprises vegetable acidified oil or waste grease containing free fatty acid.
The preparation method of the biodiesel is characterized in that the reaction conditions of the ester exchange reaction process are as follows: the reaction is carried out under normal pressure, the dosage of the methanol is 30 to 50 percent of the weight of the oil, the dosage of the catalyst calcium glycerolate is 0.2 to 2 percent of the weight of the oil, the reaction temperature is between 50 and 65 ℃, and the reaction time is between 2 and 4 hours.
The preparation method of the biodiesel is characterized in that in the preparation of the catalyst, calcium oxide solid and glycerol react in methanol to obtain a calcium glycerolate catalyst; the reaction conditions of the catalyst preparation process are as follows: the reaction temperature is 30-60 ℃, the reaction time is 2-4 h, and the molar ratio of calcium oxide, glycerol and methanol is 1.
The preparation method of the biodiesel is characterized in that the filtrate produced in the filtering process is distilled to remove methanol water and recover glycerol, the operating temperature is 50-60 ℃, and the operating pressure is 10-20 kPa.
The preparation method of the biodiesel is characterized in that the methyl ester rectification condition is that the temperature of kettle liquid is controlled to be 180-200 ℃, and the operating pressure is controlled to be 100-500 Pa; the glycerol rectification conditions are that the temperature of kettle liquid is controlled at 160-200 ℃, and the operating pressure is controlled at 500-1000 Pa.
The preparation method of the biodiesel is characterized in that the operating temperature of the steam conversion process is 700-850 ℃.
In the invention, the plant asphalt produced by methyl ester rectification can be used as heavy oil fuel for boiler fuel.
By adopting the technology, compared with the prior art, the invention has the following beneficial effects:
1. the method organically combines the glycerin esterification green deacidification technology with the glycerin calcium methanol solution catalytic transesterification technology, provides an economic, green, efficient and good-universality biodiesel preparation method, and has the advantages of low raw material requirement, simple process, high product yield, no solid waste generation, wide catalyst raw material source, regeneration and reuse and the like.
2. The glycerol esterification deacidification technology provides an ideal raw material which is anhydrous, has a low acid value and contains emulsifiers (monoglyceride and diglyceride) for the ester exchange reaction process, and the calcium glycerolate methanol solution provides a calcium glycerolate catalytic system with low saponification rate and high catalytic activity for the ester exchange reaction process, so that the greening, high-efficiency, economical and high-yield of the ester exchange reaction process are realized, the generation of saponified substances is reduced, the yield of biodiesel and glycerol is greatly improved, and the generation of asphalt is reduced.
3. The steam conversion process realizes regeneration of calcium oxide serving as a raw material of the catalyst, and simultaneously produces a byproduct of carbon monoxide and hydrogen synthesis gas. The invention can economically, green, efficiently and stably produce BD100 biodiesel.
Drawings
FIG. 1 is a process flow diagram for producing biodiesel according to an embodiment of the present application.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
The biodiesel feedstock used in example 1 was a palmitic acid oil (acid value: 160 mgKOH/g) having a fatty acid methyl ester content distribution as shown in Table 1.
TABLE 1 amount of fatty acid methyl ester in biodiesel made from palmitic acid oil
| Composition (I) | C 12:0 | C 14:0 | C 16:0 | C 18:0 | C 18:1 | C 18:2 |
| Mass fraction% | 0.15 | 1.08 | 41.03 | 5.10 | 43.55 | 9.09 |
The process flow for preparing the biodiesel according to the embodiment is shown in figure 1, and the process for preparing the biodiesel comprises the following processes:
1) Esterification reaction of glycerol: preheating raw material palmitic acid oil to 240 ℃, adding glycerol to perform a glycerol esterification reaction (fresh glycerol is used during the first secondary production, and recycled glycerol can be used later), controlling the glycerol esterification temperature to 240 ℃, and reacting for 2 hours;
2) Ester exchange reaction: cooling the feed liquid after the glycerol esterification reaction to 60 ℃, adding a methanol solution of calcium glycerolate for carrying out ester exchange reaction for 3 hours;
3) Dealcoholizing: after the ester exchange reaction is finished, flash evaporation dealcoholization is carried out while the ester exchange reaction is hot, wherein the temperature of the flash evaporation dealcoholization is 60 ℃, and the pressure is 15kPa. Wherein, the crude methanol obtained by flash evaporation dealcoholization is rectified by methanol to obtain recycled methanol which can be reused in the calcium glycerolate dissolving procedure;
4) And (3) settling: and settling the material liquid after dealcoholization to obtain crude glycerol and crude methyl ester. Wherein the obtained crude glycerol is rectified by glycerol to obtain recycled glycerol (which can be reused in a glycerol esterification reaction process or a catalyst preparation process), and the tower kettle obtains the glycerol asphalt. The glycerol asphalt is subjected to steam conversion at 800 ℃ (namely the glycerol asphalt and the steam are subjected to steam conversion reaction at 800 ℃), so that calcium oxide regeneration is realized, and meanwhile, a byproduct of synthesis gas which takes carbon monoxide and hydrogen as main components is generated (the total volume content of the carbon monoxide and the hydrogen in the synthesis gas is more than 80%), and the regenerated calcium oxide can be recycled for the catalyst preparation process;
5) Methyl ester rectification: crude methyl ester obtained by settling is rectified by methyl ester to obtain BD100 biodiesel, plant asphalt is obtained at the tower bottom and used as heavy oil fuel, and the calorific value of the plant asphalt reaches 9300Kcal/kg.
The calcium glycerolate-methanol solution used in this example was obtained through the procedures of catalyst preparation, filtration, and dissolution, and the specific process was: mixing the calcium oxide solid with glycerol and methanol, and then carrying out a reaction for preparing the catalyst, wherein the preparation temperature is 60 ℃, and the reaction time is 3 hours; after the reaction is finished, filtering the reaction mixed solution, obtaining a filter cake which is a calcium glycerolate product by filtering, and dissolving the calcium glycerolate product by using methanol (fresh methanol is used for the first time, a small amount of fresh methanol can be used later, and a large amount of recycled methanol can be used later), thus obtaining a calcium glycerolate methanol solution which is used for catalyzing the transesterification reaction process of the acidified oil.
After the reaction for preparing the catalyst is finished, filtering to obtain filtrate containing methanol, water and glycerin, performing methanol removal and water removal operation on the filtrate (namely, evaporating the methanol water component in the filtrate), and recycling the obtained reclaimed glycerin for the catalyst preparation process. Wherein the distilled methanol-water mixed solution is rectified by methanol to obtain recycled methanol which can be reused in the calcium glycerolate dissolving procedure.
The biodiesel is prepared from the palmitic acid oil by the process, the quality results of all the materials are shown in table 2, and the indexes of the obtained biodiesel product are shown in table 3.
In table 2, the feed liquid before the glycerin esterification reaction means the sum of the mass of the palmitic acid oil and the glycerin material in the glycerin esterification reaction step. The charge amount of the solid calcium oxide refers to the mass of the solid calcium oxide raw material used in the preparation of the catalyst. The charge amount of calcium glycerolate solid (wet weight) means the mass of the filter cake obtained by filtration after the completion of the catalyst preparation step. The output quality of the recycled glycerol refers to the sum of the quality of the glycerol obtained in the two processes of the methanol removal and water purification process and the glycerol rectification process.
TABLE 2 table of the mass of each material flow in the biodiesel preparation process
| Name of material | Mass per gram of feed/output |
| Palmitic acid oil | 1000 |
| Feed liquid before glycerin esterification reaction | 1170 |
| Feed liquid after glycerol esterification reaction | 1052 |
| Solid calcium oxide | 3.8 |
| Calcium glycerolate solid (Wet weight) | 15 |
| Calcium glycerolate methanol solution | 400 |
| Feed liquid after ester exchange reaction | 1452 |
| Transesterification feed liquid after dealcoholization | 1163 |
| Recycled methanol | 285 |
| Crude methyl ester after delamination | 953 |
| Crude glycerin after layering | 208 |
| BD100 biodiesel | 845 |
| Plant asphalt | 102 |
| Recycled glycerol | 220 |
| Glycerol asphalt | 30 |
| Regenerated calcium oxide | 3.4 |
TABLE 3 biodiesel quality analysis Table
| Measurement item | Biodiesel product | GB25199-2017 standard |
| Iodine number (gI) 2 /(100g)) | 53.67 | - |
| Kinematic viscosity (mm) at 40 ℃ 2 /s) | 3.68 | 1.9-6.0 |
| Density (g/cm) at 20 deg.C 3 ) | 0.8872 | 0.82-0.90 |
| Acid value (mgK ornin/g) | <0.1 | ≤0.5 |
| Ash content (wt%) | 0.004 | ≤0.02 |
| Fatty acid methyl esterEster content (wt%) | 99.67 | ≥96.5 |
| Ca 2+ Content (mg/kg) | 2.74 | ≤5 |
| Free Glycerol content (wt%) | 0.01 | ≤0.02 |
| Glyceride content (wt%) | 0.02 | ≤0.8 |
| Total glycerol content (wt%) | 0.02 | ≤0.24 |
Example 2 comparison of the effectiveness of calcium glycerolate catalyst in transesterification reactions with conventional KOH catalyst
The technology of the invention is as follows: calcium glycerolate was prepared starting from 3.4g of the calcium oxide regenerated in example 1, at a preparation temperature of 40 ℃ (the rest of the catalyst preparation conditions refer to example 1). The prepared calcium glycerolate catalyst is dissolved by methanol at 55 ℃ to form a calcium glycerolate methanol solution. 150g of the calcium glycerolate methanol solution prepared in example 2 was subjected to transesterification with 500g of the feed solution obtained in example 1 after the esterification reaction of glycerol at 60 ℃ (the amount of calcium glycerolate is 1.0wt% based on the weight of the oil), and the reaction time was 3 hours. After the ester exchange reaction is finished, the procedures of dealcoholization, sedimentation, glycerin rectification and methyl ester rectification are carried out, and the result data of the experimental process are shown in a table 4.
Conventional techniques using KOH as a transesterification catalyst: 150g of KOH methanol solution was mixed with 500g of the glycerin esterification reaction feed solution obtained in example 1, and subjected to transesterification reaction at 60 ℃ for 1 hour (the amount of KOH was 1.0wt% based on the weight of the oil). After the ester exchange reaction is finished, the procedures of dealcoholization, sedimentation, glycerin rectification and methyl ester rectification are carried out, and the result data of the experimental process is shown in Table 4.
The results of the experiments in the transesterification reaction using calcium glycerolate of the present invention as the catalyst and KOH of the conventional technology as the catalyst are shown in Table 4.
TABLE 4 comparison of the results of the transesterification of the present technology with conventional KOH technology for biodiesel production
In addition to the above embodiments, other embodiments of the present invention are also possible. All technical solutions formed by adopting equivalent substitutions or equivalent transformations fall within the protection scope of the claims of the present invention.
Claims (6)
1. A preparation method of biodiesel is characterized by comprising the following steps: carrying out glycerol esterification reaction, ester exchange reaction, dealcoholization, sedimentation and methyl ester rectification on the raw material acidified oil to obtain BD100 biodiesel; the method comprises the following steps of performing transesterification reaction, namely, mixing calcium oxide solid with glycerol and methanol, performing reaction for catalyst preparation, filtering reaction mixed liquid after the reaction is finished, obtaining a filter cake, namely a calcium glycerolate product, dissolving the calcium glycerolate product with methanol to form a calcium glycerolate methanol solution, performing transesterification reaction for catalyzing acidified oil, further performing dealcoholization, sedimentation, glycerol rectification and water vapor conversion to realize regeneration of calcium oxide, and reusing regenerated calcium oxide in the catalyst preparation process; wherein the crude methanol evaporated in the dealcoholization procedure is rectified and recycled to obtain refined methanol which is then reused in the calcium glyceroxide dissolving procedure; the crude glycerol obtained by the settling procedure is rectified and recovered by glycerol to obtain refined glycerol which is then recycled in the glycerol esterification reaction procedure or the catalyst preparation procedure;
the glycerol asphalt produced in the glycerol rectification procedure is converted by water vapor to realize calcium oxide regeneration, and meanwhile, a byproduct of synthesis gas taking carbon monoxide and hydrogen as main components is produced, wherein the operating temperature of the water vapor conversion procedure is 700-850 ℃;
the temperature of the glycerol esterification reaction is 240 ℃, and the reaction time is 2h;
the reaction conditions of the ester exchange reaction process are as follows: reacting under normal pressure, wherein the using amount of the methanol is 30-50% of the weight of the oil, the using amount of the catalyst calcium glycerolate is 0.2-2% of the weight of the oil, the reaction temperature is 50-65 ℃, and the reaction time is 2-4 h.
2. The method of claim 1, wherein the acidified oil comprises vegetable acidified oil or waste oil containing free fatty acids.
3. The method according to claim 1, wherein the reaction conditions of the catalyst preparation step are as follows: the reaction temperature is 30 to 60 ℃, the reaction time is 2 to 4 hours, and the molar ratio of the calcium oxide to the glycerol to the methanol is 1:10 to 15:7 to 15.
4. The method for preparing biodiesel according to claim 3, wherein in the preparation of the catalyst, the molar ratio of calcium oxide, glycerol and methanol is 1.
5. The method according to claim 1, wherein the filtrate obtained in the filtration step is distilled to remove methanol and water therefrom and to recover glycerin, and the operating temperature is 50 to 60 ℃ and the operating pressure is 10 to 20kPa.
6. The method for preparing biodiesel according to claim 1, wherein the methyl ester rectification conditions are that the kettle temperature is controlled within 180 to 200 ℃, and the operating pressure is controlled within 100 to 500Pa; the glycerol rectification condition is that the temperature of the kettle liquid is controlled within 160 to 200 ℃, and the operating pressure is controlled within 500 to 1000Pa.
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| CN112574826A (en) * | 2020-11-21 | 2021-03-30 | 贵州锦江生物能源科技有限公司 | Device and method for preparing fatty acid methyl ester by continuous ester exchange |
| CN112592767A (en) * | 2020-11-21 | 2021-04-02 | 贵州锦江生物能源科技有限公司 | Device and method for continuously producing biodiesel |
| CN113652307A (en) * | 2021-08-26 | 2021-11-16 | 湖南新金浩茶油股份有限公司 | Method for preparing biodiesel from tea oil cake meal |
| CN113755250B (en) * | 2021-10-09 | 2024-03-12 | 浙江工业大学 | Treatment process of biodiesel by-product crude glycerin containing solid base catalyst |
| CN114410383B (en) * | 2022-02-20 | 2023-07-25 | 浙江工业大学 | Method for preparing biodiesel by using waste grease |
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