CN112457189A - Preparation method of palm oil fatty acid ethyl ester - Google Patents
Preparation method of palm oil fatty acid ethyl ester Download PDFInfo
- Publication number
- CN112457189A CN112457189A CN202011188107.5A CN202011188107A CN112457189A CN 112457189 A CN112457189 A CN 112457189A CN 202011188107 A CN202011188107 A CN 202011188107A CN 112457189 A CN112457189 A CN 112457189A
- Authority
- CN
- China
- Prior art keywords
- palm oil
- naoh
- fatty acid
- ethyl ester
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a preparation method of palm oil fatty acid ethyl ester, which comprises the following steps: preheating palm oil, taking NaOH, putting into absolute ethyl alcohol under the protection of nitrogen, and completely dissolving the NaOH into the absolute ethyl alcohol by using ultrasonic treatment to obtain an NaOH ethanol solution; mixing the preheated palm oil with NaOH ethanol solution, and then connecting the mixture with a condensing reflux device for reaction; after the reaction is finished, pouring the reaction solution into a separating funnel, and adding petroleum ether with the same volume as the reaction solution; then, washing the reaction solution for 8 times by using a NaCl solution to demulsify the reaction solution until the lower solution is clear and transparent, standing and layering the reaction solution, discharging the lower water phase layer each time, and separating out unsaponifiable matters, glycerol and NaOH catalysts; and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester. The method takes the palm oil as the main raw material, prepares the fatty acid ethyl ester by using the absolute ethyl alcohol, has short preparation process, no corrosion, easy separation of products and higher yield.
Description
Technical Field
The invention relates to a method for preparing palm oil fatty acid ethyl ester.
Background
Fatty acid esters are the form in which a fatty acid and an alcohol are bonded via an ester bond. The types of alcohols bound to the fatty acid are mainly methanol, ethanol, propanol, butanol, etc., and thus fatty acid methyl ester, fatty acid ethyl ester, fatty acid propyl ester, fatty acid butyl ester, etc. can be prepared therefrom.
Fatty acid esters have a wide range of applications, but the most useful field of fatty acid esters is the field of biodiesel, and the use of inedible vegetable oils for preparing biodiesel has received much attention from researchers. Compared with other commonly used raw oil for preparing biodiesel, the palm oil has very high oil yield and can meet the development requirement of biological energy, so the palm oil is the main raw material stock for developing the biodiesel. Research on the preparation of biodiesel from various inedible vegetable oils has shown that inedible vegetable oils contain high saturated fatty acids, and the presence of high saturated fatty acids is advantageous for improving calorific value, but adversely affects low-temperature properties, viscosity, and the like. Among them, fatty acid methyl ester and fatty acid ethyl ester are mainly used because of their low price.
Fatty acid ethyl esters are prepared using animal/vegetable lipids such as palm oil, soybean oil, canola oil, fish oil, coconut oil, and the like and free fatty acids derived from animal/vegetable lipids by transesterification using an alcohol and a catalyst at high temperature, and can be obtained by a process of separating glycerin, unreacted fatty acids, unreacted ethanol, and the like (Fuel, 2009, 88 (3): 579-582). Chinese patent application No. 201110201711.1 mentions a method for preparing fatty acid ethyl ester using soybean oil.
At present, two main methods for preparing fatty acid ethyl ester at home and abroad are available, one is fatty acid ethyl ester prepared by the reaction of fatty acid and ethanol, and the other is fatty acid ethyl ester prepared by the transesterification of grease and ethanol. The oil and fat ethanol ester exchange method has short time, the final product is easy to separate, and the solvent can be recovered. Therefore, the method of transesterification of fats and oils with ethanol is basically used. The transesterification method of oil and ethanol can be divided into acid catalysis method, alkali catalysis method and biological enzyme catalysis method according to different types of catalysts, the alkali catalyst has high catalysis efficiency relative to the acid catalyst, the required reaction temperature is low, the raw oil can be prevented from being oxidized and decomposed, and the price is low relative to the biological enzyme catalyst. Encinar et al studied the effect of different concentrations of acid and base catalysts on the yield of tallow biodiesel and found that NaOH was more efficient than sodium methoxide and that the best yield was obtained at 9% NaOH (Bioresource Technology, 2011, 102 (23): 10907-.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for preparing fatty acid ethyl ester which takes palm oil as a main raw material and can be widely used in food without using chemical substances which are possibly harmful to human bodies or can cause irritation.
The technical scheme for solving the technical problems is as follows:
a preparation method of palm oil fatty acid ethyl ester comprises the following steps:
(1) preheating palm oil to 65-75 ℃;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) according to the weight percentage of NaOH being 0.5-2.0% of the weight of palm oil, the molar ratio of absolute ethyl alcohol to palm oil is 3-7: 1, taking NaOH, putting the NaOH into absolute ethyl alcohol, and performing ultrasonic treatment to completely dissolve the NaOH into the absolute ethyl alcohol to obtain an NaOH ethanol solution;
(4) mixing the preheated palm oil with NaOH ethanol solution, and then connecting the mixture with a condensing reflux device to react for 60-180 min at the temperature of 65-80 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing with NaCl solution with the mass fraction of 5% to demulsify the reaction liquid until the lower layer solution is clear and transparent, standing and layering, discharging the lower layer water phase layer each time, and separating out unsaponifiable matters, glycerol and NaOH catalysts;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
Preferably, in the above-described method for producing palm oil fatty acid ethyl ester: the preheating temperature of the palm oil in the step (1) is 65 ℃.
Preferably, in the above-described method for producing palm oil fatty acid ethyl ester: in the step (3), the weight of NaOH is 0.8 percent of the weight of palm oil.
Preferably, in the above-described method for producing palm oil fatty acid ethyl ester: the molar ratio of the absolute ethyl alcohol to the palm oil in the step (3) is 3: 1.
preferably, in the above-described method for producing palm oil fatty acid ethyl ester: the reaction temperature in step (4) was 70 ℃.
Preferably, in the above-described method for producing palm oil fatty acid ethyl ester: the reaction time in step (4) was 90 min.
Compared with the prior art, the invention has the following beneficial effects:
1. compared with an acid catalysis method, the method has more advantages, the catalysis rate of the base catalyst is higher than that of the acid catalyst, so that the reaction time is relatively short, the consumption of ethanol and the catalyst by the base catalysis method is less, and the fatty acid ethyl ester prepared by the reaction of the base catalysis method has light color and accords with the purchase psychology of consumers;
2. methanol is known to be harmful to the human body and causes blindness and severe vomiting, but ethanol is metabolized and converted into acetic acid in the body, which has little toxicity to the human body; the method is used for alcohols of fatty acid esters, and has economic advantages by using methanol and ethanol, wherein the main sources of the methanol are nonrenewable resources such as natural gas and coal, while the source of the ethanol is renewable resource, and the ethanol is greener and safer when used for preparing fatty acid ethyl ester from edible palm oil;
3. the invention has the advantages of high economic benefit, simple process method, production cost saving, increased utilization rate of raw materials, reduced energy consumption and the like.
Detailed Description
The present invention will be further described with reference to the following examples, but it should be noted that the scope of the present invention is not limited to these examples.
Example 1:
(1) preheating 25.00g of palm oil to 70 ℃ in a constant-temperature water bath kettle;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) weighing NaOH which is 0.8 percent of the weight of palm oil, putting the NaOH into weighed absolute ethyl alcohol (the molar ratio of the absolute ethyl alcohol to the palm oil is 3: 1), and treating the mixture for 10 min by using ultrasonic waves with the ultrasonic power of 200W to completely dissolve the NaOH into the absolute ethyl alcohol to obtain NaOH ethanol solution;
(4) pouring NaOH and absolute ethyl alcohol solution dissolved by ultrasonic waves into a preheated three-neck flask with the volume of 100 mL of palm oil, and then connecting a condensation reflux device to react for 90 min at 70 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing the reaction solution for 8 times by using a NaCl solution with the mass fraction of 5% to demulsify the reaction solution until the lower layer solution is clear and transparent, standing and layering the reaction solution, discharging a lower water phase layer each time, and separating unsaponifiable matters, glycerol and a NaOH catalyst;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
Example 2:
(1) preheating 25.00g of palm oil to 65 ℃ in a constant-temperature water bath kettle;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) weighing NaOH which is 0.5 percent of the weight of palm oil, putting the NaOH into weighed absolute ethyl alcohol (the molar ratio of the absolute ethyl alcohol to the palm oil is 4: 1), and treating the mixture for 10 min by using ultrasonic waves with the ultrasonic power of 200W to completely dissolve the NaOH into the absolute ethyl alcohol to obtain NaOH ethanol solution;
(4) pouring NaOH and absolute ethyl alcohol solution dissolved by ultrasonic waves into a preheated three-neck flask with the volume of 100 mL of palm oil, and then connecting a condensation reflux device to react for 60 min at the temperature of 65 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing the reaction solution for 8 times by using a NaCl solution with the mass fraction of 5% to demulsify the reaction solution until the lower layer solution is clear and transparent, standing and layering the reaction solution, discharging a lower water phase layer each time, and separating unsaponifiable matters, glycerol and a NaOH catalyst;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
Example 3:
(1) preheating 25.00g of palm oil to 75 ℃ in a constant-temperature water bath kettle;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) weighing NaOH which is 1.5 percent of the weight of palm oil, putting the NaOH into weighed absolute ethyl alcohol (the molar ratio of the absolute ethyl alcohol to the palm oil is 5: 1), and treating the mixture for 10 min by using ultrasonic waves with the ultrasonic power of 200W to completely dissolve the NaOH into the absolute ethyl alcohol to obtain NaOH ethanol solution;
(4) pouring NaOH and absolute ethyl alcohol solution dissolved by ultrasonic waves into a preheated three-neck flask with the volume of 100 mL of palm oil, and then connecting a condensation reflux device to react for 120 min at the temperature of 80 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing the reaction solution for 8 times by using a NaCl solution with the mass fraction of 5% to demulsify the reaction solution until the lower layer solution is clear and transparent, standing and layering the reaction solution, discharging a lower water phase layer each time, and separating unsaponifiable matters, glycerol and a NaOH catalyst;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
Example 4:
(1) preheating 25.00g of palm oil to 70 ℃ in a constant-temperature water bath kettle;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) weighing NaOH which is 2.0 percent of the weight of palm oil, putting the NaOH into weighed absolute ethyl alcohol (the molar ratio of the absolute ethyl alcohol to the palm oil is 7: 1), and treating the mixture for 10 min by using ultrasonic waves with the ultrasonic power of 200W to completely dissolve the NaOH into the absolute ethyl alcohol to obtain NaOH ethanol solution;
(4) pouring NaOH and absolute ethyl alcohol solution dissolved by ultrasonic waves into a preheated three-neck flask with the volume of 100 mL of palm oil, and then connecting a condensation reflux device to react for 180 min at the temperature of 75 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing the reaction solution for 8 times by using a NaCl solution with the mass fraction of 5% to demulsify the reaction solution until the lower layer solution is clear and transparent, standing and layering the reaction solution, discharging a lower water phase layer each time, and separating unsaponifiable matters, glycerol and a NaOH catalyst;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
Claims (6)
1. The preparation method of palm oil fatty acid ethyl ester is characterized by comprising the following steps: the method comprises the following steps:
(1) preheating palm oil to 65-75 ℃;
(2) introducing nitrogen with the flow rate of 25 mL/min into the three-neck flask for protection so as to remove oxygen in a reaction system;
(3) according to the weight percentage of NaOH being 0.5-2.0% of the weight of palm oil, the molar ratio of absolute ethyl alcohol to palm oil is 3-7: 1, taking NaOH, putting the NaOH into absolute ethyl alcohol, and performing ultrasonic treatment to completely dissolve the NaOH into the absolute ethyl alcohol to obtain an NaOH ethanol solution;
(4) mixing the preheated palm oil with NaOH ethanol solution, and then connecting the mixture with a condensing reflux device to react for 60-180 min at the temperature of 65-80 ℃;
(5) after the reaction is finished, pouring the reaction liquid into a separating funnel while the reaction liquid is hot in time, and adding petroleum ether with the boiling range of 60-90 ℃ and the volume amount equal to that of the reaction liquid; then, washing with NaCl solution with the mass fraction of 5% to demulsify the reaction liquid until the lower layer solution is clear and transparent, standing and layering, discharging the lower layer water phase layer each time, and separating out unsaponifiable matters, glycerol and NaOH catalysts;
(6) and (3) carrying out rotary evaporation on the reaction liquid at-0.98 MPa and 60 ℃ for 60 min to obtain the palm oil fatty acid ethyl ester.
2. The method for preparing palm oil fatty acid ethyl ester according to claim 1, wherein the method comprises the following steps: the preheating temperature of the palm oil in the step (1) is 65 ℃.
3. The method for preparing palm oil fatty acid ethyl ester according to claim 1, wherein the method comprises the following steps: in the step (3), the weight of NaOH is 0.8 percent of the weight of palm oil.
4. The method for preparing palm oil fatty acid ethyl ester according to claim 1, wherein the method comprises the following steps: the molar ratio of the absolute ethyl alcohol to the palm oil in the step (3) is 3: 1.
5. the method for preparing palm oil fatty acid ethyl ester according to claim 1, wherein the method comprises the following steps: the reaction temperature in step (4) was 70 ℃.
6. The method for preparing palm oil fatty acid ethyl ester according to claim 1, wherein the method comprises the following steps: the reaction time in step (4) was 90 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011188107.5A CN112457189A (en) | 2020-10-30 | 2020-10-30 | Preparation method of palm oil fatty acid ethyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011188107.5A CN112457189A (en) | 2020-10-30 | 2020-10-30 | Preparation method of palm oil fatty acid ethyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112457189A true CN112457189A (en) | 2021-03-09 |
Family
ID=74835610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011188107.5A Pending CN112457189A (en) | 2020-10-30 | 2020-10-30 | Preparation method of palm oil fatty acid ethyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112457189A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113248368A (en) * | 2021-05-19 | 2021-08-13 | 江苏达成生物科技有限公司 | Method for reducing content of acylglyceride impurities in long-chain dibasic acid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1411042A1 (en) * | 2002-10-15 | 2004-04-21 | Cosmo Engineering Co., Ltd. | Method for producing fatty acid alcohol ester |
| CN1858161A (en) * | 2006-06-02 | 2006-11-08 | 中国农业科学院油料作物研究所 | Process for preparing biological diesel oil using palm oil |
| CN104140885A (en) * | 2013-05-12 | 2014-11-12 | 南京工业大学 | Method for preparing anti-oxidative fatty acid ester by using oil-containing plant seeds as raw material |
| CN106906052A (en) * | 2017-03-21 | 2017-06-30 | 广西科技大学 | A kind of new method for preparing vegetable fatty acetoacetic ester |
-
2020
- 2020-10-30 CN CN202011188107.5A patent/CN112457189A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1411042A1 (en) * | 2002-10-15 | 2004-04-21 | Cosmo Engineering Co., Ltd. | Method for producing fatty acid alcohol ester |
| CN1858161A (en) * | 2006-06-02 | 2006-11-08 | 中国农业科学院油料作物研究所 | Process for preparing biological diesel oil using palm oil |
| CN104140885A (en) * | 2013-05-12 | 2014-11-12 | 南京工业大学 | Method for preparing anti-oxidative fatty acid ester by using oil-containing plant seeds as raw material |
| CN106906052A (en) * | 2017-03-21 | 2017-06-30 | 广西科技大学 | A kind of new method for preparing vegetable fatty acetoacetic ester |
Non-Patent Citations (1)
| Title |
|---|
| 钟俊良等，: ""棕榈油脂肪酸乙酯制备的研究"", 《2015年粮油食品新技术与新装备科技论坛暨行业发展峰会论文集》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113248368A (en) * | 2021-05-19 | 2021-08-13 | 江苏达成生物科技有限公司 | Method for reducing content of acylglyceride impurities in long-chain dibasic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Meneghetti et al. | Ethanolysis of castor and cottonseed oil: A systematic study using classical catalysts | |
| CN101372539B (en) | Method for producing environment-friendly type plasticiser using waste oil and oil foot | |
| Paiva et al. | Non-edible babassu oil as a new source for energy production–a feasibility transesterification survey assisted by ultrasound | |
| CN100569914C (en) | A kind of method of utilizing producing biodiesel from high acid number grease | |
| Jeong et al. | Batch (one-and two-stage) production of biodiesel fuel from rapeseed oil | |
| CN101688150A (en) | Biodiesel production | |
| CN101215233B (en) | Technique for producing fatty acid methyl ester | |
| CN102876465A (en) | Method for preparing biodiesel by using kitchen waste oil | |
| CN101215475B (en) | Middle and low temperature preparation method for biological diesel oil by using plants fruits and seeds oil and special-purpose distillation tower for the same | |
| AU2014203729A1 (en) | Method for improving yield of enzymatic preparation of biodiesel from greases | |
| CN112457189A (en) | Preparation method of palm oil fatty acid ethyl ester | |
| CN100360644C (en) | Production process of biological diesel | |
| KR100790298B1 (en) | Manufacturing method of high purity fatty acid alkylester and fatty acid alkylester manufactured therefrom | |
| Panneerselvam et al. | Biodiesel production from mutton tallow | |
| CN100526427C (en) | Method and catalyst for producing biological diesel oil by high-acid value grease | |
| Zeng et al. | A review of transesterification from low-grade feedstocks for biodiesel production with supercritical methanol | |
| CN101531913A (en) | Method for preparing biodiesel | |
| CN101423767A (en) | Method for preparing biodiesel by alcohol extraction and solid base catalysis two-step method | |
| CN100402631C (en) | Method for synthesizing biodiesel | |
| CN102071107A (en) | Method for preparing monoglyceride under supercritical carbon dioxide (CO2) condition | |
| CN101892128A (en) | Method for catalytic production of branching biological diesel by resin | |
| CN101289628A (en) | Process for producing biodiesel from mixed fatty acid | |
| CN101225324B (en) | One-step method for preparing biodiesel by low-acid catalytic fatty or fatty acid | |
| CN202610209U (en) | High acid value oil and fat preparation biodiesel device | |
| CN1970693A (en) | Process for preparing biological diesel oil by using soapstock |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |