CN116836053A - Method for preparing vegetable oleic acid through repeated rectification - Google Patents
Method for preparing vegetable oleic acid through repeated rectification Download PDFInfo
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- CN116836053A CN116836053A CN202310814689.0A CN202310814689A CN116836053A CN 116836053 A CN116836053 A CN 116836053A CN 202310814689 A CN202310814689 A CN 202310814689A CN 116836053 A CN116836053 A CN 116836053A
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- oleic acid
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- oleate
- rectification
- porous adsorbent
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 205
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 158
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 157
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 157
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 157
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 157
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 157
- 238000000034 method Methods 0.000 title claims abstract description 59
- 235000013311 vegetables Nutrition 0.000 title claims abstract description 31
- 239000003463 adsorbent Substances 0.000 claims abstract description 52
- 229940049964 oleate Drugs 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000000706 filtrate Substances 0.000 claims abstract description 24
- 238000001914 filtration Methods 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000012046 mixed solvent Substances 0.000 claims abstract description 16
- 238000007127 saponification reaction Methods 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 15
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 14
- 239000008158 vegetable oil Substances 0.000 claims abstract description 14
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 12
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 12
- 238000004108 freeze drying Methods 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 29
- 229910021389 graphene Inorganic materials 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 108010010803 Gelatin Proteins 0.000 claims description 12
- 238000001354 calcination Methods 0.000 claims description 12
- 239000008273 gelatin Substances 0.000 claims description 12
- 229920000159 gelatin Polymers 0.000 claims description 12
- 235000019322 gelatine Nutrition 0.000 claims description 12
- 235000011852 gelatine desserts Nutrition 0.000 claims description 12
- 239000012298 atmosphere Substances 0.000 claims description 10
- 239000000499 gel Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 description 140
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 235000019871 vegetable fat Nutrition 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000007790 solid phase Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000009776 industrial production Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021315 omega 9 monounsaturated fatty acids Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing vegetable oleic acid by multiple times of rectification. The invention comprises the following steps: in a solvent, performing saponification reaction on fatty acid methyl ester in vegetable oil under alkaline conditions to obtain a mixture, and performing freeze drying on the obtained mixture to obtain oleate; recrystallizing the obtained oleate to obtain purified oleate, redissolving in a solvent, adding a porous adsorbent, adding acid for neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid; rectifying the primary oleic acid; repeating the above operation at least twice to obtain medium-grade oleic acid; adding the medium-grade oleic acid into a water-containing mixed solvent containing a porous adsorbent, and crystallizing by cooling step by step to obtain the vegetable oleic acid. The method has the advantages of simple process, simple operation and lower cost, and can be used for producing the oleic acid with high quality requirement on a large scale.
Description
Technical Field
The invention relates to the technical field of preparation of high-purity oleic acid, in particular to a method for preparing vegetable oleic acid through repeated rectification.
Background
Oleic acid (Oleica) of the formula C 18 H 34 O 2 Is a monounsaturated Omega-9 fatty acid, also called cis-9-octadecenoic acid, which is unsaturated fatty acid containing one double bond in natural oil and fat, and exists in natural animal oil and vegetable oil in glyceride form. Oleic acid, especially high purity oleic acid, is an important fine chemical product and can be widely applied to paint ink, coating, mineral flotation agent, film antistatic agent, slipping agent, textile auxiliary agent, explosive emulsifier and the like.
The raw materials of the industrial oleic acid in China mainly come from animal (vegetable) oil, acidified oil (a byproduct of refining vegetable oil), swill oil, recovered oil of catering industry, tall oil and the like. Depending on the source and the preparation process used, the index of oleic acid will vary considerably, thus leading to a diversity of applications of oleic acid products.
In recent years, the purity of oleic acid is mostly maintained at 70% -80%. Among known production methods, solvent separation, emulsion separation, chromatographic separation using an adsorbent, ion exchange chromatographic separation, selective hydrogenation of linoleic acid and linolenic acid to oleic acid, etc., but these methods cannot meet the requirements for industrially producing high-purity oleic acid on a large scale, in order to expand the production scale, researchers have focused on other production methods such as a freeze-press method, a crystallization press method, a rectification method, an organic solvent method, a surfactant method, a urea complexation method, etc. Wherein, the urea complexation method and the organic solvent method have high production cost; the separation degree of the surfactant method is too low to meet the industrial requirements, and the surfactant method is basically eliminated; the freezing and squeezing method has low efficiency and large occupied area, and cannot achieve large-scale industrialized production; nowadays, the most used for preparing oleic acid of high purity is the rectification process as well as the crystallization press filtration process.
The rectification method realizes separation and storage according to different carbon chain lengths and different boiling points of fatty acids. Since the oleic acid is mainly a mixture of C16 and C18, C16 can be well separated by a rectification method, but the separation of homologues of the C18 rectification method is difficult, so that the freezing point of oleic acid produced by the rectification method is generally higher, generally higher than 15 ℃, and oleic acid with a lower freezing point is difficult to obtain by the method.
The crystallization press filtration method is a method for effectively separating saturated acid fatty acid and unsaturated fatty acid with low melting point by cooling to form crystal precipitation of high melting point hexadecanoic acid and stearic acid and then separating by diaphragm press filtration, and is an industrial production method suitable for high-quality oleic acid. The crystallization press filtration method is to heat the fatty acid to ensure that all saturated fatty acid is completely dissolved, put the fatty acid into a crystallization tank, perform crystallization press filtration and perform program cooling. Crystallizing and filtering to obtain oleic acid. The process method is simple, and can realize large-scale industrial production. The disadvantage is that more strict process control is required, liquid fatty acid is easily entrained in the hard cake, and the product yield is reduced.
In order to meet the requirement of high-purity oleic acid in industrial production, development of a process method with high product yield and high oleic acid purity is urgently needed.
Disclosure of Invention
Therefore, the invention aims to solve the technical problems of low yield and low purity of oleic acid in industrial production in the prior art.
In order to solve the technical problems, the invention provides a method for preparing vegetable oleic acid through repeated rectification. The method has the advantages of simple process, simple operation and lower cost, and can be used for producing the oleic acid with high quality requirement on a large scale.
The invention is realized by the following technical scheme:
the invention aims to provide a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In a solvent, performing saponification reaction on fatty acid methyl ester in vegetable oil under alkaline conditions to obtain a mixture, and performing freeze drying on the obtained mixture to obtain oleate;
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding a porous adsorbent, adding acid to perform a neutralization reaction, and filtering to obtain a filtrate, wherein the filtrate is primary oleic acid;
(3) Rectifying the primary oleic acid in the step (2);
(4) Repeating the step (3) for at least two times to obtain medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a water-containing mixed solvent containing a porous adsorbent, and crystallizing by cooling step by step to obtain the vegetable oleic acid;
in the step (3), a rectification system in the rectification treatment comprises a dehydration degassing tower, an evaporation tower, a rectification tower and an oleic acid tower; and adding a porous adsorbent into the rectifying tower.
In one embodiment of the present invention, in step (1), the solvent is an aqueous solution of an alcohol. Further, the water content is 2wt% to 10wt%. Preferably 2wt%, 3wt%, 4wt%, 5wt%, 6wt%, 7wt%, 8wt%, 9wt%, 10wt% and the like. Or any value between any two values.
In one embodiment of the present invention, in step (1), the saponification reaction conditions: the heating temperature is 90-95 ℃ and the saponification reaction time is 1-2 hours.
In one embodiment of the present invention, in the step (1), the alkaline condition agent of the alkaline condition is sodium hydroxide and/or potassium hydroxide, and the pH value of the alkaline condition is 10-11.
In one embodiment of the present invention, in step (2), the porous adsorbent is prepared by the following method: dispersing gelatin into a solvent at 65-85 ℃, adding graphene oxide, mixing to obtain gelatin-graphene oxide, stirring until a gel state is formed, and calcining in an atmosphere containing organic gas to obtain the porous adsorbent.
In one embodiment of the invention, the solvent is water.
In one embodiment of the invention, the mass ratio of the gelatin to the graphene oxide is 1:1-2. Preferably 1:1. 1: 2. 1:1.5, etc.
In one embodiment of the invention, the calcining conditions are: the temperature is 600-900 ℃; the time is 3h-12h.
Further, the organic gas is one or more of methane, ethylene and ethane.
In one embodiment of the present invention, in step (2), the porous adsorbent is used in an amount of 20wt% to 30wt%.
In one embodiment of the invention, in the step (2), the rectification pressure is 100MPa-200MPa, the temperature of the top discharge hole of the rectification column in the rectification system is 195-200 ℃, and the temperature of the bottom material of the rectification column is 240-245 ℃; the temperature of a top discharge hole in the oleic acid tower is 160-165 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220-225 ℃, and the temperature of a bottom material in the oleic acid tower is 240-250 ℃. The rectifying device is a device conventional in the art and sequentially comprises an evaporation tower, a rectifying tower and an oleic acid tower. Wherein, the oleic acid tower contains two outlets of the middle part and the top part.
In one embodiment of the invention, in step (2), the acid is selected from hydrochloric acid.
In one embodiment of the present invention, in step (5), the mixed solvent containing water further comprises diethyl ether or acetone; the water content of the aqueous mixed solvent is 1-5wt%. The adsorption function of the adsorbent is utilized to play a role of removing impurities once more; meanwhile, according to the cooling process, through stage cooling, impurities form crystal precipitation on the surface of the adsorbent, the adsorbent is separated, and the impurities are removed again.
In one embodiment of the present invention, in step (5), the step-wise cooling process: the temperature of the first stage is reduced to 0 ℃ to-10 ℃, the temperature of the second stage is reduced to-20 ℃ to-15 ℃, and the temperature of the third stage is reduced to-30 ℃ to-20 ℃.
Compared with the prior art, the technical scheme of the invention has the following advantages:
(1) According to the invention, the porous adsorbent is added, so that the adsorption performance is improved by utilizing the porosity, impurities are removed in advance before rectification, and the content of oleic acid impurities can be reduced. Meanwhile, the purity of the oleic acid is further improved by combining a method of repeated rectification.
(2) The method is simple, the device is conventional rectification equipment in the field, and the equipment requirement is low; the organic solvents are used less, and besides two organic solvents of ethanol and acetone, the other organic solvents are used very little, so that the cost is reduced and the possibility of environmental pollution is reduced.
(3) The invention reduces the temperature step by step in the final stage, increases the probability for improving the purity again, and ensures the purity by step through gradual temperature reduction.
Drawings
In order that the invention may be more readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings, in which:
FIG. 1 is a schematic diagram of the apparatus of the rectification system of the present invention.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and specific examples, which are not intended to be limiting, so that those skilled in the art will better understand the invention and practice it.
Example 1
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 600 ℃ for 10 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 40min, the temperature in the third stage is reduced to-25 ℃ and the solid phase is obtained after night crystallization, and the purity of the vegetable oleic acid is 88% and the color of the vegetable oleic acid is light.
Example 2
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 10 wt%) fatty acid methyl ester in vegetable oil and fat is placed in potassium hydroxide solution, the pH value of the mixed solution is 11, heating is carried out to make saponification reaction, heating temperature is 95 deg.C, heating time is 2 hr so as to obtain reaction mixture, and the obtained reaction mixture is freeze-dried so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 25wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 600 ℃ for 4 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 200MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material of the rectifying tower is 240 ℃; the temperature of a top discharge hole in the oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 240 ℃, and fractions of the oleic acid discharge hole are collected.
(4) Repeating the step (3) for two times, and finally collecting the fraction which is the medium-grade oleic acid.
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-3 ℃ for 20min, the temperature in the second stage is reduced to-15 ℃ for 30min, the temperature in the third stage is reduced to-30 ℃ for overnight crystallization, filtering, and taking a solid phase to obtain the vegetable oleic acid with the purity of 86% and light color.
Example 3
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 900 ℃ for 3 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 40min, the temperature in the third stage is reduced to-25 ℃ and the solid phase is obtained after night crystallization, and the purity of the vegetable oleic acid is 87% and the light color is obtained after filtering.
Example 4
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 2 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 800 ℃ for 12 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 200MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 45min, the temperature in the third stage is reduced to-30 ℃ for overnight crystallization, filtering, and obtaining the vegetable oleic acid with the purity of 89% and the light color.
Example 5
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 3 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 2 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 65 ℃, adding 2g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring until a gel state is formed, and calcining in an atmosphere containing ethylene at 900 ℃; and (5) obtaining the porous adsorbent after 5 hours.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for three times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-10 ℃ for 35min, the temperature in the second stage is reduced to-18 ℃ for 30min, the temperature in the third stage is reduced to-25 ℃ and the solid phase is obtained after night crystallization, and the purity of the vegetable oleic acid is 88% and the light color is obtained after filtering.
Example 6
The embodiment provides a method for preparing vegetable oleic acid through multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 900 ℃ for 5 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 40min, the temperature in the third stage is reduced to-25 ℃ and the solid phase is obtained after night crystallization, and the purity of the vegetable oleic acid is 85% and the color of the vegetable oleic acid is light.
Comparative example 1 (in comparison to example 1, except that no adsorbent was used)
The comparative example provides a method for preparing vegetable oleic acid by multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding hydrochloric acid for neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 40min, the temperature in the third stage is reduced to-25 ℃ and the temperature is crystallized overnight, filtering, and taking a solid phase to obtain the vegetable oleic acid, wherein the purity is 80% and the color is slightly deep.
Comparative example 2 (in comparison with example 1, the difference is that the rectification is once)
The comparative example provides a method for preparing vegetable oleic acid by multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 600 ℃ for 10 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole of the middle oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole of the oleic acid tower is 220 ℃, the temperature of a bottom material of the oleic acid tower is 250 ℃, fractions of the oleic acid discharge hole are collected, and the collected fractions are medium oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, cooling step by step, wherein the temperature in the first stage is reduced to-5 ℃ for 20min, the temperature in the second stage is reduced to-18 ℃ for 40min, the temperature in the third stage is reduced to-25 ℃ and the solid phase is filtered, so that the vegetable oleic acid with the purity of 75% and the light color is obtained.
Comparative example 3 (in contrast to example 1), the difference being that the temperature reduction in step (5) is not staged
The comparative example provides a method for preparing vegetable oleic acid by multiple times of rectification, which comprises the following steps:
(1) In ethanol water solution (water content is 5 wt%) fatty acid methyl ester in vegetable oil and fat is placed in sodium hydroxide solution, pH value of the mixed solution is 10, heating is carried out to make saponification reaction, heating temperature is 90 deg.C, heating time is 1 hr so as to obtain reaction mixture, and freeze-drying the obtained reaction mixture so as to obtain oleate.
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding 20wt% of porous adsorbent, adding hydrochloric acid to perform neutralization reaction, and filtering to obtain filtrate, wherein the filtrate is primary oleic acid;
wherein, the preparation method of the porous adsorbent comprises the following steps: dispersing 2g of gelatin into deionized water at 85 ℃, adding 3g of graphene oxide, mixing to obtain gelatin-graphene oxide, stirring to form a gel state, and calcining in a methane-containing gas atmosphere at 600 ℃ for 10 hours to obtain the porous adsorbent.
(3) And (3) rectifying the primary oleic acid in the step (2), wherein the rectifying conditions are as follows: the rectification pressure is 100MPa, the temperature of a top discharge hole of a rectifying tower in a rectification system is 200 ℃, and the temperature of a bottom material is 245 ℃; the temperature of a top discharge hole in an oleic acid tower is 160 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220 ℃, the temperature of a bottom material in the oleic acid tower is 250 ℃, and fractions of the oleic acid discharge hole are collected;
(4) Repeating the step (3) for two times, wherein the finally collected fraction is medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a mixed solvent of water and acetone (the volume ratio of water to acetone is 20:80) containing a porous adsorbent, reducing the temperature to-25 ℃, crystallizing overnight, filtering, and taking a solid phase to obtain the vegetable oleic acid with the purity of 79% and a light color.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations and modifications of the present invention will be apparent to those of ordinary skill in the art in light of the foregoing description. It is not necessary here nor is it exhaustive of all embodiments. And obvious variations or modifications thereof are contemplated as falling within the scope of the present invention.
Claims (9)
1. The method for preparing the vegetable oleic acid by multiple times of rectification is characterized by comprising the following steps of:
(1) In a solvent, performing saponification reaction on fatty acid methyl ester in vegetable oil under alkaline conditions to obtain a mixture, and performing freeze drying on the obtained mixture to obtain oleate;
(2) Recrystallizing the oleate obtained in the step (1) to obtain purified oleate, redissolving the oleate in a solvent, adding a porous adsorbent, adding acid to perform a neutralization reaction, and filtering to obtain a filtrate, wherein the filtrate is primary oleic acid;
(3) Rectifying the primary oleic acid in the step (2);
(4) Repeating the step (3) for at least two times to obtain medium-grade oleic acid;
(5) Adding the medium-grade oleic acid into a water-containing mixed solvent containing a porous adsorbent, and crystallizing by cooling step by step to obtain the vegetable oleic acid.
2. The method according to claim 1, wherein in step (1), the saponification reaction conditions are: the heating temperature is 90-95 ℃ and the saponification reaction time is 1-2 hours.
3. The method according to claim 1, wherein in the step (1), the alkaline condition agent is sodium hydroxide and/or potassium hydroxide, and the pH value of the alkaline condition is 10-11.
4. The method of claim 1, wherein in step (2), the porous adsorbent is prepared by: dispersing gelatin into a solvent at 65-85 ℃, adding graphene oxide, mixing to obtain gelatin-graphene oxide, stirring until a gel state is formed, and calcining in an atmosphere containing organic gas to obtain the porous adsorbent.
5. The method according to claim 4, wherein the mass ratio of gelatin to graphene oxide is 1:1-2.
6. The method of claim 4, wherein the calcining conditions: the temperature is 600-900 ℃; the time is 3h-12h.
7. The method of claim 1, wherein in step (2), the porous adsorbent is used in an amount of 20wt% to 30wt%.
8. The method according to claim 1, wherein in the step (3), the rectification pressure is 100MPa to 200MPa, the temperature of the top outlet of the rectification column in the rectification system is 195 ℃ to 200 ℃, and the temperature of the bottom material is 240 ℃ to 245 ℃; the temperature of a top discharge hole in the oleic acid tower is 160-165 ℃, the temperature of a middle oleic acid discharge hole in the oleic acid tower is 220-225 ℃, and the temperature of a bottom material in the oleic acid tower is 240-250 ℃.
9. The method according to claim 1, wherein in step (5), diethyl ether or acetone is further included in the aqueous mixed solvent; the water content of the aqueous mixed solvent is 1-5wt%.
The method of claim 1, wherein in step (5), the step-down process is: the temperature of the first stage is reduced to 0 ℃ to-10 ℃, the temperature of the second stage is reduced to-20 ℃ to-15 ℃, and the temperature of the third stage is reduced to-30 ℃ to-20 ℃.
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| CN101838590A (en) * | 2010-05-25 | 2010-09-22 | 九江力山环保科技有限公司 | Production process of rectified light-colored oleic acid |
| CN110002951A (en) * | 2019-03-26 | 2019-07-12 | 大连大平油脂化学有限公司 | A kind of oleic acid preparation method |
| CN112552166A (en) * | 2020-12-10 | 2021-03-26 | 浙江中控技术股份有限公司 | Oleic acid crystallization process control method and device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101838590A (en) * | 2010-05-25 | 2010-09-22 | 九江力山环保科技有限公司 | Production process of rectified light-colored oleic acid |
| CN110002951A (en) * | 2019-03-26 | 2019-07-12 | 大连大平油脂化学有限公司 | A kind of oleic acid preparation method |
| CN112552166A (en) * | 2020-12-10 | 2021-03-26 | 浙江中控技术股份有限公司 | Oleic acid crystallization process control method and device |
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