NL2033281A - Method for purifying fatty acid methyl esters - Google Patents

Method for purifying fatty acid methyl esters Download PDF

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Publication number
NL2033281A
NL2033281A NL2033281A NL2033281A NL2033281A NL 2033281 A NL2033281 A NL 2033281A NL 2033281 A NL2033281 A NL 2033281A NL 2033281 A NL2033281 A NL 2033281A NL 2033281 A NL2033281 A NL 2033281A
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fatty acid
acid methyl
methyl ester
water
solution
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NL2033281A
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Dutch (nl)
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Ren Peng
Ping Yuan
Li Yin
Ma Min
Wang Yiyong
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Suzhou Fengbei Biotech Co Ltd
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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
    • 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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • 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
    • C11B3/006—Refining fats or fatty oils by extraction
    • 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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/04—Refining fats or fatty oils by chemical reaction with acids

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fertilizers (AREA)

Abstract

The present disclosure provides a method for purifying fatty acid methyl esters, which comprises mixing crude fatty acid methyl ester with nitric acid to react organic sulfur in the crude fatty acid methyl ester with nitric acid, and then washing the reaction system with an aqueous glycerin solution, and then separating oil and water in the system washed with the aqueous glycerin solution to give a desulfurized fatty acid methyl esters. In the present disclosure, organic sulfur such as glucosinolate is decomposed into water—soluble sub— stances such as carboxylic acid, glucose, thione and hydrogen sulfate ions by using nitric acid, and then the adsorption of sulfides in the elution water is increased by glycerol, thereby removing these water—soluble substances, to prepare desulfurized fatty acid methyl esters, not only the prepara— tion process has low energy consumption, the preparation method is simple, and there is basically no loss of fatty acid methyl esters; the water phase produced after washing in the 20 present application can also be used as fermentation water for bio—organic fertilizer, the whole preparation process is pol— lution—free and does not generate exhaust gas, waste water and solid waste, which is green and environmentally friendly, and is especially suitable for industrial production.

Description

NL 35070-FE/bk
METHOD FOR PURIFYING FATTY ACID METHYL ESTERS
TECHNICAL FIELD OF THE INVENTION
[0001] The present disclosure relates to a method for puri- fying fatty acid methyl esters.
BACKGROUND OF THE INVENTION
[0002] Petroleum, coal, natural gas and other petrochemical resources are non-renewable resources. With the advancement of industrialization, their total amount is becoming in short sup- ply increasingly, and the development of renewable energy has become a global hotspot, while the amount of bioenergy is in- creasing year by year due to its green, environmentally friendly and renewable nature, especially fatty acid methyl esters are not only used as energy sources but also as excellent chemical solvents. The catering industry in our country is developed, and the waste oil is large in quantity and low in cost as an excellent raw material for fatty acid methyl esters, however, due to that the waste oil is mostly recycled oil processed at high tempera- ture, it inevitably contains fat-soluble organic sulfides, and the content of the organic sulfides substance is above 200 ppm.
Biodiesel produced from these raw materials will produce a large amount of sulfur dioxide and release it into the atmosphere, causing great harm to the environment and people's health, and limiting the application of fatty acid methyl esters.
[0003] Therefore, the desulfurization technology of fatty acid methyl esters has been widely studied, mainly including hydrodesulfurization and non-hydrodesulfurization. The hy- drodesulfurization requires the production plant to have a hydrogenation supporting production line. Although the hydro- genation can reduce the sulfur content, it destroys the chemical structure of biodiesel and limits its use as a safe solvent.
Non-hydrodesul furization mainly includes multi-stage distilla- tion and adsorption desulfurization. Patent CN110041956A discloses a continuous stripping distillation desulfurization method for crude biodiesel, where through multi-stage distilla- tion, the sulfur content in the product is reduced to below 50 ppm, but the multistage distillation has high energy consumption and large loss, especially the distillation process causes the ineffective waste problem of the fractions of a large amount of fatty acid methyl esters enriched with organic sulfur. Existing manufacturers do not have a good treatment method. Generally, they can only control the rectification process, reduce losses and recover by multiple distillations. However, for the frac- tions enriched with sulfur content, the method of re- distillation cannot be used, resulting in waste of fatty acid methyl esters. Patent CN108822884A discloses a liquid ionic salt sulfur extractant, which can reduce the sulfur content, however, the preparation process of the extractant is complicated and the preparation cost of the extractant is high, so it is not suitable for industrial production.
SUMMARY OF THE INVENTION
[0004] The technical problem to be solved by the present dis- closure provides a method for purifying fatty acid methyl esters with simple steps and low cost.
[0005] To achieve the above purpose, a technical solution employed by the present disclosure is:
[0006] The present disclosure provides a method for purifying fatty acid methyl esters, which comprises mixing crude fatty acid methyl ester with nitric acid to react organic sulfur in the crude fatty acid methyl ester with nitric acid, and then washing the reaction system with an aqueous glycerin solution, and then separating oil and water in the washed system to give an oil phase containing desulfurized fatty acid methyl esters.
[0007] Preferably, the reaction temperature is controlled to be 60 to 75 °C, further 65 to 75 °C, more further 65 to70 °C.
[0008] Further preferably, the reaction time is controlled to be 1 to 2 h, further 1.5 to 2 h.
[0009] Preferably, the nitric acid is an aquecus nitric acid solution, and the mass concentration of the aqueous nitric acid solution is 5 to 10%.
[0010] Further preferably, the feeding mass ratio of the crude fatty acid methyl ester to the aqueous nitric acid solution is 100: {1 to 3).
[0011] Preferably, the aqueous nitric acid solution is fed in one-time or in batches in the form of atomization.
[0012] Further preferably, the aqueous nitric acid solution is fed in batches in the form of atomization, and the feeding times of the aqueous nitric acid solution is 2 to 3 times.
[0013] Preferably, before and/or during and/or after mixing the crude fatty acid methyl ester with nitric acid, stirring the reaction system, and controlling the stirring speed to be 60 to 100 rpm.
[0014] Preferably, the separation of the oil and water in the washed system comprises warming the system to 90 to 95 °C after washing, and then cooling the system to 25 to 30 °C to realize oil-water separation in the system.
[0015] Preferably, the feeding mass ratio of the aqueous glyc- erin solution to the crude fatty acid methyl ester is (5 to 10): 100.
[0016] Further preferably, the mass concentration of the aqueous glycerin solution is 3 to 5%.
[0017] Preferably, the method for purifying fatty acid methyl esters further comprises detecting the oil phase obtained after washing, the detecting comprises taking part of the oil phase, and then mixing the oil phase with distilled water to prepare a mixed solution, with the mass ratio of the oil phase to the distilled water in the mixed solution being (3 to 8): 100, then detecting the pH of the mixed solution, and the washing is qual- ified when the pH of the mixed solution is 6 to 8, otherwise washing the reaction system again until the pH of the mixed solution prepared by mixing the oil phase and distilled water is 6 to 8.
[0018] Preferably, the method for purifying fatty acid methyl esters further comprises after oil-water separation, performing vacuum distillation on the separated oil phase to give desulfu- rized fatty acid methyl esters.
[0019] Further preferably, the temperature of vacuum distil- lation is controlled to be 120 to 130 °C.
[0020] More further preferably, the pressure of vacuum dis- tillation is controlled to be 0.05 to 0.08 MPa.
[0021] Preferably, the method for purifying fatty acid methyl esters further comprises after oil-water separation, adjusting the pH of the separated water phase to 6 to 8 with a potassium hydroxide solution of a mass concentration of 3 to 8 3, then the mixed solution after adjustment can be used as fermentation water for biological fertilizer.
[0022] Preferably, the crude fatty acid methyl ester com- prises organic sulfur and long-chain fatty acid methyl esters, the organic sulfur comprises glucosinolates and their metabo- lites, and the long-chain fatty acid methyl esters are fatty acid methyl esters with carbon chain lengths of 8 to 22.
[0023] Further preferably, the long-chain fatty acid methyl esters comprise one or more of selected from the group consisting of methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl oleate, me- thyl linoleate, methyl linolenate, methyl erucate, and methyl arachiate.
[0024] According to some preferred implementations, the method for purifying fatty acid methyl esters comprises the fol- lowing steps:
[0025] (1) Mixing crude fatty acid methyl ester with an aque- ous nitric acid solution with a mass concentration of 5 to 10% 5 to react organic sulfur in the crude fatty acid methyl ester with nitric acid, wherein the feeding mass ratio of the crude fatty acid methyl ester to the aqueous nitric acid solution is 100: (1 to 3), the aqueous nitric acid solution is fed in batches in the form of atomization, the reaction temperature is con- trolled to be 60 to 75 °C, and the reaction time is controlled to be 1 to 2 hy;
[0026] (2) After the reaction of step (1) is completed, wash- ing the reaction system with an aqueous glycerin solution with a mass concentration of 3 to 5%, wherein the feeding mass ratio of the aqueous glycerin solution to the crude fatty acid methyl ester is (5 to 10): 100;
[0027] (3) After the reaction of step (2) is completed, warm- ing the system of step (2) to 90 to 95 °C, and then cooling the system to 25 to 30 °C to carry out oil-water separation to obtain oil phase and water phase;
[0028] (4) Performing vacuum distillation on the oil phase to give desulfurized fatty acid methyl esters, wherein the temper- ature of vacuum distillation is controlled to be 120 to 130 °C, and the pressure is controlled to be 0.05 to 0.08 MPa;
[0029] (5) Adjusting the pH of the water phase to 6 to 8 with an aqueous potassium hydroxide solution of a mass concentration of 3 to 8 % to obtain fermentation water that can be used for preparing organic fertilizers.
[0030] Due to the use of the above technical solutions, the present disclosure has the following advantages over the prior art:
[0031] In the present disclosure, organic sulfur such as glu- cosinolate is decomposed into water-soluble substances such as carboxylic acid, glucose, thione and hydrogen sulfate ion by using nitric acid, and then these water-soluble substances are removed by washing, and an aqueous glycerin solution is used instead of water as elution, the aqueous glycerin solution can adsorb and elute the produced sulfur and nitrogen compounds, thereby effectively preparing desulfurized fatty acid methyl es- ters, not only the preparation process has low energy consumption, the preparation method is simple, and there is ba- sically no loss of fatty acid methyl esters; the water phase produced after washing in the present application can also be used as fermentation water for bio-organic fertilizer, the whole preparation process is pollution-free and does not generate ex- haust gas, waste water and solid waste, which is green and environmentally friendly, and is especially suitable for indus- trial production.
DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS
[0032] In the following, specific implementations of the pre- sent disclosure are explained.
[0033] The applicant found that the organic sulfur in the present application is mostly glucosinolates and their metabo- lites, and due to the high liposolubility of glucosinolates and their metabolites, simple washing methods cannot separate them from fatty acid methyl esters. The inventor first thought of using oxidative acid, namely nitric acid to treat the crude fatty acid methyl ester, so that organic sulfur is decomposed into water-soluble substances such as carboxylic acid, glucose, thi- one and hydrogen sulfate ion under the action of nitric acid, and then these water-soluble substances are removed by washing with an aqueous glycerin solution, thereby achieving effective desulfurization of the crude fatty acid methyl ester. Further, the washing liquid after washing in this application can also be used as fermentation water for bio-organic fertilizer, and no waste liquid is produced in the whole process of this applica- tion, which meets the needs of green development.
[0034] According to some implementations, the method for pu- rifying fatty acid methyl esters comprises the following steps:
[0035] (1) Mixing crude fatty acid methyl ester with nitric acid to react organic sulfur in the crude fatty acid methyl ester with nitric acid;
[0036] (2) After the reaction of step (1) is completed, wash- ing the reaction system with an aqueous glycerin solution;
[0037] (3) Carry out oil-water separation on the system of step (2) to obtain oil phase and water phase;
[0038] (4) Performing vacuum distillation on the oil phase to give desulfurized fatty acid methyl esters;
[0032] (5) Adjusting the pH of the water phase with potassium hydroxide to obtain fermentation water that can be used for preparing organic fertilizers.
[0040] Further, the reaction temperature in the above step (1) is 60 to 75 °C, for example, 60 °C, 61 °C, 62 °C, 63 °C, 64 °c, 65 °c, 66 °C, 67 °C, 68 °C, 69 °c, 70 °c, 71 °c, 72 °c, 73 °c, 74 °C, 75 °C. If the reaction temperature is too high, the nitric acid will decompose, which will affect the reaction rate and desulfurization effect; if the reaction temperature is too low, the nitric acid will sediment too fast and affect the desulfurization effect the one hand, and it will affect the effect of oil-water separation on the other hand. The reaction time can be adjusted according to the feeding amount of the reactants and the reaction temperature, and preferably, the re- action time is 1 to 2 h.
[0041] In some implementations of the present disclosure, the nitric acid in this application is preferably fed in the form of an adqueous nitric acid solution. The mass concentration of the aqueous nitric acid solution is 5 to 10%, for example, 5 %, 6%, 7%, 8 3, 9 3, 10 2%. The higher the mass concentration of the aqueous nitric acid solution, the higher the local temperature when the aqueous nitric acid solution is mixed with the crude fatty acid methyl ester, and there is a risk of local overheat- ing; the lower the mass concentration of the aqueous nitric acid solution, the aguecus nitric acid solution cannot completely decompose organic sulfur, which affects the desulfurization ef- fect.
[0042] In some implementations of the present disclosure, the feeding mass ratio of the crude fatty acid methyl ester to the aqueous nitric acid solution in this application is 100: (1 to 3), for example, 100: 1, 100: 2, 100: 3. The feeding amount of the aqueous nitric acid solution should not be too large, if the feeding amount of the aqueous nitric acid solution is too large, the difficulty of washing is increased on the one hand, and a small amount of hydrolysis of fatty acid methyl esters may be caused on the other hand, thereby affecting the yield of fatty acid methyl esters; the feeding amount of the nitric acid aqueous solution should not be too small, otherwise the organic sulfur cannot be completely decomposed, which will affect the desulfu- rization effect.
[0043] Further, the feeding mode of the aqueous nitric acid solution can be drop feeding or atomization feeding. Preferably, the aqueous nitric acid solution is fed in the form of atomiza- tion. Feeding can be one-time feeding or feeding in batches, in order to prevent local overheating when the aqueous nitric acid solution is mixed with fatty acid methyl esters, the mode of feeding in batches is preferably used, for example, the atomized aqueous nitric acid solution is put into the crude fatty acid methyl ester in 2 to 3 times. In addition, before and/or during and/or after mixing the aquecus nitric acid solution with the fatty acid methyl esters, the reaction system is stirred, and the stirring speed is 60 to 100 rpm, for example, 60 rpm, 70 rpm, 80 rpm, 90 rpm, 100 rpm.
[0044] In the above-mentioned steps (2), the feeding amount of the aqueous glycerin solution can be adjusted according to the feeding amount of the aqueous nitric acid solution and the sulfur content of the raw materials, and when the feeding amount of the aqueous nitric acid solution is too large or the sulfur content of the raw materials is too high, the feeding amount of the aqueous glycerol solution is increased to remove the sulfur and nitrogen compounds generated in the reaction; when the feed- ing amount of the aqueous nitric acid solution is small or the sulfur content of the raw materials is low, the feeding amount of the aqueous glycerin solution can be appropriately reduced.
Preferably, the feeding mass ratio of the aqueous glycerin so- lution to the crude fatty acid methyl ester is (5 to 10): 100, for example, 5: 100, 6: 100, 7: 100, 8: 100, 9: 100, 10: 100.
[0045] Further, the oil phase obtained after washing is de- tected to judge whether the washing is qualified. The detecting method comprises taking part of the oil phase to mix the oil phase with water to prepare a mixed solution, with the mass ratio of the oil phase to water in the mixed solution being (3 to 8): 100, for example, 3: 100, 4: 100, 5: 100, 6: 100, 7: 100, 8: 100, then detecting the pH of the mixed solution, and the washing is qualified when the pH of the mixed solution is 6 to 8, oth- erwise washing the reaction system again until the pH of the mixed solution prepared by mixing the oil phase and water is 6 to 8.
[0046] According to some specific and preferable implementa- tions, the above step (3) further comprises warming the system to 90 to 95 °C, and then cooling the system to 25 to 30 °C to realize oil-water separation in the system. Compared with di- rectly separating the washed system, raising the temperature of the washed system first and then cooling it down for oil-water separation can effectively improve the yield of fatty acid methyl esters. Preferably, the temperature of the system can be cooled to 25 to 30 °C by natural cooling and then oil-water separation can be carried out.
[0047] According to some specific and preferable implementa- tions, the above step (2) further comprises washing with an aqueous glycerin solution, wherein the mass concentration of the agueous glycerin solution is 3 to 5%, for example, the mass ratio of glycerin to water may be 3: 100, 4: 100, 5: 100. For raw materials with high sulfur content, the preferred mass ratio of glycerol to water is 5: 100, and the mass concentration of the aqueous glycerin solution can be adjusted according to the sulfur content of the raw materials.
[0048] According to some specific and preferable implementa- tions, the distillation temperature in the above step (4) is 120 to 130 °C, for example, 120 °C, 121 °C, 122 °C, 123 °C, 124 °C, 125 °C, 126 °c, 127 °C, 128 °C, 129 °C, 130 °C. If the distil- lation temperature is too high, the energy consumption is too large, thus increasing the cost; if the distillation temperature is too low, the water removal rate decreases, and the water removal effect is poor.
[0049] Further, the pressure of distillation is 0.05 to 0.08
Mpa, for example, 0.05 Mpa, 0.06 Mpa, 0.07 Mpa, 0.08 Mpa.
[0050] According to some specific and preferable implementa- tions, potassium hydroxide in the above step (5) is an aqueous potassium hydroxide solution, with a mass concentration of 3 to 8%, for example, 3 %, 4 2, 5 %, 6 %, 7 %, 8 2. Adjusting the pH of the separated water phase to 6 to 8 with an aqueous potassium hydroxide solution, the mixed solution after adjustment can be used as fermentation water for biological fertilizer.
[0051] The crude fatty acid methyl ester in this application comprises organic sulfur and long-chain fatty acid methyl es- ters, the organic sulfur comprises glucosinolate and its metabolites, and the long-chain fatty acid methyl esters are fatty acid methyl esters with carbon chain lengths of 8 to 22.
Further, the long-chain fatty acid methyl esters comprise one or more of selected from the group consisting of methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmi- tate, methyl stearate, methyl oleate, methyl linoleate, methyl linolenate, methyl erucate, and methyl arachiate.
[0052] In the following, the present disclosure is further described combining with embodiments. However, the present dis- closure is not limited to the following embodiments. The implementation conditions adopted in the embodiments can be fur- ther adjusted according to different requirements of specific use, and the unspecified implementation conditions are the con- ventional conditions in the industry. The technical features involved in the respective implementations of the present dis- closure can be combined with each other as long as they do not conflict with each other.
[0053] The sulfur contents were determined according to SH T 0689-2000 Standard test method for determination of total sulfur in light hydrocarbons, motor fuels and oils by ultraviolet flu- orescence.
[0054] Blank: untreated fatty acid methyl esters, namely crude fatty acid methyl ester, its main components are fatty acid methyl esters, water and organic sulfur, the organic sulfur is mainly glucosinolate and its metabolites, wherein the mass content of fatty acid methyl esters in crude fatty acid methyl ester was higher than 99 %, the water content was < 1%, and the sulfur content was 260 ppm.
[0055] The crude fatty acid methyl esters in the following embodiments and comparative examples are all in the same batch as the untreated fatty acid methyl esters.
[0056] Unless otherwise specified, "parts" in the following embodiments and comparative examples refer to "parts by weight".
[0057] Embodiment 1
[0058] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor, wherein, the mass con- centration of the nitric acid solution was 10 %, and the nitric acid solution was added at twice and the system was stirred after the nitric acid solution was added to mix the nitric acid solu- tion and the fatty acid methyl ester evenly, and the amount of the nitric acid solution added each time was controlled to be consistent.
[0059] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 70 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 52 aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the aqueous glycerol solution was added to the reaction system in 3 times and the addition amount was the same each time,
[0060] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.5 to 6.8.
[0061] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 1. The pH of the water phase was adjusted to 6.8 to 7.2 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0062] Embodiment 2
[0063] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor at one time, wherein, the mass concentration of the nitric acid solution was 5%.
[0064] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 65 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 5% aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the adueous glycerol solution was added to the reaction system in 2 times and the addition amount was the same each time.
[0065] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.7 to 6.9.
[0066] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 2, and the pH of the water phase was adjusted to 7.2 to 7.4 with a 5 % KOH solution, which was used as fermentation water for bioc-organic fertilizer at the desired pH.
[0067] Embodiment 3
[0068] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor, wherein, the mass con- centration of the nitric acid solution was 10 +, and the nitric acid solution was added at twice and the system was stirred after the nitric acid solution was added to mix the nitric acid solu- tion and the fatty acid methyl ester evenly, and the amount of the nitric acid solution added each time was controlled to be consistent.
[0069] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 70 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 3% aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the aqueous glycerol solution was added to the reaction system in 3 times and the addition amount was the same each time. The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.1 to 6.4.
[0070] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 3. The pH of the water phase was adjusted to 7.3 to 7.5 with a 5 3 KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0071] Embodiment 4
[0072] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor, wherein, the mass con- centration of the nitric acid solution was 10 3, and the nitric acid solution was added at 3 times and the system was stirred after the nitric acid solution was added to mix the nitric acid solution and the fatty acid methyl ester evenly, and the amount of the nitric acid solution added each time was controlled to be consistent.
[0073] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 70 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 4% aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the aqueous glycerol solution was added to the reaction system in 3 times and the addition amount was the same each time. The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.3 - 6.6,
[0074] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 4. The pH of the water phase was adjusted to 7.1 to 7.3 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0075] Embodiment 5
[0076] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor, wherein, the mass con- centration of the nitric acid solution was 10 3, and the nitric acid solution was added at twice and the system was stirred after the nitric acid solution was added to mix the nitric acid solu- tion and the fatty acid methyl ester evenly, and the amount of the nitric acid solution added each time was controlled to be consistent.
[0077] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 60 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 5% aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the aqueous glycerol solution was added to the reaction system in 3 times and the addition amount was the same each time.
[0078] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.7 to 7.0.
[0079] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 5. The pH of the water phase was adjusted to 7.2 to 7.6 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0080] Comparative example 1
[0081] 100 parts of crude fatty acid methyl ester were added into a reactor, then the reactor was heated to 70 °C and kept at the temperature. After 2 hours, the system was washed with water, wherein the total addition amount of water was 10 parts, and the water was added to the system in 3 times and the addition amount was the same each time.
[0082] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, and the oil phase was dehydrated by vacuum distillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 6. The pH of the water phase was adjusted to 7.6 to 7.9 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0083] Comparative example 2
[0084] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of sulfuric acid solution atomized by an atomizer were added into the reactor, wherein, the mass concentration of the sulfuric acid solution was 10 %, and the sulfuric acid solution was added at twice and the system was stirred after the sulfuric acid solution was added to mix the sulfuric acid solution and the fatty acid methyl ester evenly, and the amount of the sulfuric acid solution added each time was controlled to be consistent.
[0085] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 70 °C and kept warm to carry out the reaction. After reacting for 2 hours, the reaction system was washed with a 3% aqueous glycerol solution, wherein the total addition amount of the aqueous glycerol solution was 10 parts, and the aqueous glycerol solution was added to the reaction system in 3 times and the addition amount was the same each time.
[0086] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 6.0 to 6.5.
[0087] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 7. The pH of the water phase was adjusted to 7.2 to 7.5 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0088] Comparative example 3
[0089] 100 parts of crude fatty acid methyl ester were added into a reactor, then 2 parts of nitric acid solution atomized by an atomizer were added into the reactor, wherein, the mass con- centration of the nitric acid solution was 10 3, and the nitric acid solution was added at twice and the system was stirred after the nitric acid solution was added to mix the nitric acid solu- tion and the fatty acid methyl ester evenly, and the amount of the nitric acid solution added each time was controlled to be consistent.
[0090] The stirring device in the reactor was started, the stirring speed was controlled to be 100 rpm, and the reactor was heated to 70 °C and kept warm to carry out the reaction. After 2 hours, the system was washed with distilled water, wherein the total addition amount of water was 10 parts, and the distilled water was added to the system in 3 times and the addition amount was the same each time.
[0091] The washed system was heated to 95 °C, then stopped heating and cooled to 25 °C naturally to separate the water phase and the oil phase, then 5 parts of the oil phase were taken, 100 parts of distilled water were added to the oil phase to prepare a mixed solution, and the pH of the mixed solution was detected, the washing was qualified when the pH of the mixed solution was measured to be 5.3 to 5.5.
[0092] The remaining oil phase was dehydrated by vacuum dis- tillation under the conditions of 0.05 MPa and 120 °C, to give a desulfurized finished fatty acid methyl ester 8. The pH of the water phase was adjusted to 7.6 to 7.9 with a 5 % KOH solution, which was used as fermentation water for bio-organic fertilizer at the desired pH.
[0093] The test results of the above-mentioned embodiments and comparative examples are shown in Table 1.
[0094] Table 1
[0095]
Sulphur content
Samples (ppm)
Blanks Crude fatty acid methyl 260 ester
Fmbodiment 1 Finished fatty acid me- 44 thyl ester 1
Finished fatt id -
Embodiment 2 tHishe ALLY aci me 48 thyl ester 2
Finish f i -
Embodiment 3 inished fatty acid me 48 thyl ester 3 embodiment 4 Finished fatty acid me- 47 thyl ester 4
Finish Ê -
Embodiment 5 inished fatty acid me 57 thyl ester 5
Comparative Finished fatty acid me- 58 example 1 thyl ester 6
Comparative Finished fatty acid me- 144 example 2 thyl ester 7
Comparative Finished fatty acid me- 67 example 3 thyl ester 8
[0096] The above detailed describes the present disclosure, and is intended to make those skilled in the art being able to understand the present disclosure and thereby implement it, and should not be concluded to limit the protective scope of this disclosure. Any equivalent variations or modifications according to the spirit of the present disclosure should be covered by the protective scope of the present disclosure.

Claims (14)

CONCLUSIESCONCLUSIONS 1. Een methode voor het zuiveren van vetzuurmethylesters, gekenmerkt door het omvatten van: mengen van ruw vetzuur- methylester met salpeterzuur om organische zwavel in de ruwe vetzuurmethylester te laten reageren met salpeter- zuur; en dan wassen van het reactiesysteem met een waterige glycerineoplossing; en dan scheiden van olie en water in het gewassen systeem om een olie fase te verkrij- gen die een ontzwaveld vetzuurmethylester bevat.A method for purifying fatty acid methyl esters, characterized by comprising: mixing crude fatty acid methyl ester with nitric acid to react organic sulfur in the crude fatty acid methyl ester with nitric acid; and then washing the reaction system with an aqueous glycerin solution; and then separating oil and water in the washed system to obtain an oil phase containing a desulfurized fatty acid methyl ester. 2. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, met het kenmerk dat de reactietemperatuur wordt beheerst op 60-75 °C en/of de reactietijd wordt be- heerst tot 1-2 uur.The method for purifying fatty acid methyl esters according to claim 1, characterized in that the reaction temperature is controlled at 60-75°C and/or the reaction time is controlled at 1-2 hours. 3. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, met het kenmerk dat het salpeterzuur een waterige salpeterzuuroplossing is met een massaconcentra- tie van 53-103, en/of de voedingsmassaverhouding van de ruwe vetzuurmethylester tot de waterige salpeterzuuroplos- sing 100: (1-3) is.3. The method for purifying fatty acid methyl esters according to claim 1, characterized in that the nitric acid is an aqueous nitric acid solution with a mass concentration of 53-103, and/or the feed mass ratio of the crude fatty acid methyl ester to the aqueous nitric acid solution 100: (1-3) is. 4. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 3 met het kenmerk dat de waterige salpeterzuur oplossing in geatomiseerde vorm wordt toegevoerd, in één keer of in batches.4. The method for purifying fatty acid methyl esters according to claim 3, characterized in that the aqueous nitric acid solution is supplied in an atomized form, at one time or in batches. 5. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 4, met het kenmerk dat de waterige salpeterzuuroplossing in een geatomiseerde vorm in 2-3 batches wordt toegevoerd.The method for purifying fatty acid methyl esters according to claim 4, characterized in that the aqueous nitric acid solution is fed in an atomized form in 2-3 batches. 6. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, gekenmerkt door voor en/of tijdens en/of na het mengen van de ruwe vetzuurmethylester met salpeterzuur roeren van het reactiesysteem en beheersen van de roer- snelheid van 60-100 tpm.6. The method for purifying fatty acid methyl esters according to claim 1, characterized by stirring the reaction system before and/or during and/or after mixing the crude fatty acid methyl ester with nitric acid and controlling the stirring speed from 60-100 rpm . 7. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, met het kenmerk dat de scheiding van de olie en het water in het gewassen systeem omvat: verhitting van het systeem tot 90-95 °C na het wassen, en afkoeling van het systeem tot 25-30 °C om olie/water scheiding in het systeem te bewerkstelligen.7. The method for purifying fatty acid methyl esters according to claim 1, characterized in that the separation of the oil and water in the washed system comprises: heating the system to 90-95 °C after washing, and cooling the the system to 25-30 °C to achieve oil/water separation in the system. 8. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, gekenmerkt door een voedingsmassa-verhouding van de waterige glycerineoplossing tot de ruwe vetzuurme- thylester van (5-10):100 en/of waarbij de massaconcentratie van de waterige glycerineoplossing 3%-5% bedraagt.8. The method for purifying fatty acid methyl esters according to claim 1, characterized by a feed mass ratio of the aqueous glycerin solution to the crude fatty acid methyl ester of (5-10):100 and/or wherein the mass concentration of the aqueous glycerin solution is 3 %-5%. 9. De methode voor het zuiveren van vetzuurmethylesters vol- gens claim 1, met het kenmerk dat methode voor het zuiveren van vetzuurmethylesters verder omvat: bepalen van de olie fase, verkregen na het wassen, waarbij het bepalen omvat: nemen van een deel van de olie fase; mengen van de olie fase met gedestilleerd water om een mengsel te berei- den met een voedingsmassa-verhouding van de olie fase tot het gedestilleerde water in het mengsel van (3-8):100; en het meten van een pH van het mengsel, waarbij wanneer de DH van het mengsel 6-8 als gewassen wordt gekwalificeerd; en anders, het opnieuw wassen van het reactiesysteem tot- dat de pH van het mengsel bereid door het mengen van de olie fase en het gedestilleerde water 6-8 bedraagt.9. The method for purifying fatty acid methyl esters according to claim 1, characterized in that the method for purifying fatty acid methyl esters further comprises: determining the oil phase obtained after washing, the determining comprising: taking part of the oil phase; mixing the oil phase with distilled water to prepare a mixture having a feed mass ratio of the oil phase to the distilled water in the mixture of (3-8):100; and measuring a pH of the mixture, wherein when the DH of the mixture 6-8 qualifies as washed; and otherwise, washing the reaction system again until the pH of the mixture prepared by mixing the oil phase and the distilled water is 6-8. 10. De methode voor het zuiveren van vetzuurmethylesters volgens claim 1, gekenmerkt door: na de olie/waterige fa- sescheiding, een vacuumdestillatie van de afgescheiden olie fase uit te voeren om ontzwavelde vetzuurmethylester te verkrijgen, waarbij de temperatuur van de vacuumdestil- latie wordt geregeld op 120-130 °C, en de druk wordt geregeld op 0,05-0,08 Mpa.10. The method for purifying fatty acid methyl esters according to claim 1, characterized by : after the oil/aqueous phase separation, conducting a vacuum distillation of the separated oil phase to obtain desulfurized fatty acid methyl ester, the temperature of the vacuum distillation being regulated at 120-130 °C, and the pressure is controlled at 0.05-0.08 Mpa. 11. De methode voor het zuiveren van vetzuurmethylesters volgens claim 1, gekenmerkt door: na de olie/water schei- ding, de afgescheiden waterige fase op pH 6-8 brengen met behulp van een kaliumhydroxideoplossing met een massacon- centratie van 3%-8% om een aangepast mengsel te verkrijgen dat kan worden gebruikt als een fermentatiemedium voor een biologische meststof.11. The method for purifying fatty acid methyl esters according to claim 1, characterized by : after the oil/water separation, adjusting the separated aqueous phase to pH 6-8 using a potassium hydroxide solution with a mass concentration of 3%-8 % to obtain an adapted mixture that can be used as a fermentation medium for an organic fertilizer. 12. De methode voor het zuiveren van methylvetzuuresters volgens claim 1, met het kenmerk dat het ruwe vetzuurme- thylesterproduct organische zwavel en een lang-ketenige vetzuurmethylester bevat, waarbij de organische zwavel glucosinolaat en een metoboliet daarvan bevat en de lang- ketenige vetzuurmethylester een vetzuurmethylester met een keten van 8-22 koolstofatomen is.12. The method for purifying methyl fatty acid esters according to claim 1, characterized in that the crude fatty acid methyl ester product contains organic sulfur and a long chain fatty acid methyl ester, wherein the organic sulfur contains glucosinolate and a metabolite thereof and the long chain fatty acid methyl ester contains a fatty acid methyl ester with a chain of 8-22 carbon atoms. 13. De methode voor het zuiveren van vetzuurmethylesters volgens claim 12, met het kenmerk dat de vetzuurmethyles- ter met lange keten een of meer van de volgende stoffen bevat: methylcaprylaat, methylcapraat, methyllauraat, me- thylmyristaat, methylpalmitaat, methylstearaat, methyloleaat, methyllinolenaat, methylerucaat en methy- larachidaat.13. The method for purifying fatty acid methyl esters according to claim 12, characterized in that the long chain fatty acid methyl ester contains one or more of the following: methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl oleate, methyl linolenate , methyl erucate and methyl arachidate. 14. De methode voor het zuiveren van vetzuurmethylesters volgens een van de claims 1 tot en met 13,met het kenmerk dat de methode voor het zuiveren van vetzuurmethylesters de volgende stappen omvat: (1) het mengen van ruw vetzuurmethylesterproduct met een waterige salpeterzuuroplossing met een massaconcentra- tie van 52-103 om organische zwavel in de ruwe vetzuurmethylester te laten reageren met salpeterzuur, waarbij de massaverhouding van de toevoer van het ruwe vetzuurmethylester tot de waterige salpeterzuuroplossing 100:{1-3) is, de waterige salpeterzuuroplossing in geato- miseerde vorm in batches wordt toegevoerd, de reactietemperatuur wordt geregeld op 60-75 °C en de reac- tietijd 1-2 uur is; (2) na de reactie in stap (1), het wassen van het reac- tiesysteem met een waterige glycerineoplossing met een massaconcentratie van 3%-5%, waarbij de voedingsmassa-ver- houding van de waterige glycerineoplossing tot de ruwe vetzuurmethylester (5-10):100 is; (3) na het wassen in stap (2), verhitting van het sys- teem in stap (2) tot 90-95 °C, en dan natuurlijke afkoeling van het systeem tot 25-30 °C om olie en water te scheiden om een oliefase en een waterfase te verkrijgen;14. The method for purifying fatty acid methyl esters according to any one of claims 1 to 13, characterized in that the method for purifying fatty acid methyl esters comprises the following steps: (1) mixing crude fatty acid methyl ester product with an aqueous nitric acid solution containing a mass concentration of 52-103 to react organic sulfur in the crude fatty acid methyl ester with nitric acid, where the mass ratio of the feed of the crude fatty acid methyl ester to the aqueous nitric acid solution is 100:{1-3), the aqueous nitric acid solution in atomized form is fed in batches, the reaction temperature is controlled at 60-75°C and the reaction time is 1-2 hours; (2) after the reaction in step (1), washing the reaction system with an aqueous glycerin solution at a mass concentration of 3%-5%, the nutrient mass ratio of the aqueous glycerin solution to the crude fatty acid methyl ester (5 -10):100; (3) after washing in step (2), heating the system in step (2) to 90-95 °C, and then natural cooling of the system to 25-30 °C to separate oil and water to to obtain an oil phase and a water phase; (4) vacuumdestilleren van de olie fase om de ontzwa- velde vetzuurmethylester te verkrijgen, waarbij de temperatuur van de vacuumdestillatie bij verlaagde druk wordt geregeld op 120-130 °C en de druk wordt geregeld op 0,05-0,08 MPa; en (5) de waterige fase op pH 6-8 brengen door middel van een kaliumhydroxideoplossing met een massaconcentratie van 34-84, zodat een fermentatiemedium ontstaat voor de berei- ding van organische meststoffen.(4) vacuum distilling the oil phase to obtain the desulfurized fatty acid methyl ester, wherein the temperature of the vacuum distillation under reduced pressure is controlled at 120-130°C and the pressure is controlled at 0.05-0.08 MPa; and (5) adjusting the aqueous phase to pH 6-8 by means of a potassium hydroxide solution with a mass concentration of 34-84, to provide a fermentation medium for the preparation of organic fertilizers.
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