CN114432729B - Composite embedding agent and preparation method and application thereof - Google Patents
Composite embedding agent and preparation method and application thereof Download PDFInfo
- Publication number
- CN114432729B CN114432729B CN202011198158.6A CN202011198158A CN114432729B CN 114432729 B CN114432729 B CN 114432729B CN 202011198158 A CN202011198158 A CN 202011198158A CN 114432729 B CN114432729 B CN 114432729B
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- biodiesel
- acid methyl
- methyl ester
- dihydric alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 27
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 27
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 13
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 8
- 238000004321 preservation Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 45
- 239000003225 biodiesel Substances 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229940043237 diethanolamine Drugs 0.000 claims description 11
- -1 unsaturated fatty acid methyl ester Chemical class 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- 239000008162 cooking oil Substances 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 20
- 239000004202 carbamide Substances 0.000 abstract description 20
- 238000010899 nucleation Methods 0.000 abstract description 4
- 230000006911 nucleation Effects 0.000 abstract description 4
- 238000001556 precipitation Methods 0.000 abstract description 3
- 150000002009 diols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 13
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 7
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 7
- 229940073769 methyl oleate Drugs 0.000 description 7
- 238000000926 separation method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 230000008014 freezing Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VJQGGZWPOMJLTP-UHFFFAOYSA-N octadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCC(O)O VJQGGZWPOMJLTP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a compoundThe preparation method comprises heating long-chain diol to melt, adding diethanolamine and K under heat preservation, and adding 2 CO 3 And dehydrating agent, carrying out ultrasonic treatment, and filtering to obtain the composite embedding agent. The composite embedding agent prepared by the invention has the functions of nucleation and embedding, is suitable for precipitation of saturated fatty acid methyl ester, and has less consumption compared with urea.
Description
Technical Field
The invention belongs to the technical field of biodiesel, and particularly relates to a composite embedding medium for saturated fatty acid methyl ester, and a preparation method and application thereof.
Background
The biodiesel is a typical 'green renewable energy source' which is produced by using animal and vegetable oil, swill-cooked dirty oil and the like as raw materials to produce renewable environment-friendly fuel, has performance close to that of diesel oil, can replace petroleum diesel oil as fuel for an engine. Biodiesel is generally a mixed fatty acid methyl ester containing both saturated fatty acid methyl esters and unsaturated fatty acid methyl esters, and typically requires separation of saturated fatty acid methyl esters.
The common separation methods at present include a freeze-pressing method, a solvent freeze-separation method, a urea inclusion method and the like. The freezing and squeezing method is to directly freeze the crude fatty acid ester into paste and then squeeze the paste to obtain the unsaturated fatty acid ester, and the method has the disadvantages of difficult realization of continuous production, low production efficiency, high energy consumption and large labor amount. The solvent freezing separation method is to directly freeze a mixed solution of crude fatty acid ester and an organic solvent into paste, and then obtain unsaturated fatty acid ester through centrifugal separation. The principle of the urea inclusion method is that in the crystallization process, straight chain fatty acid (ester) in the system is easy to form urea inclusion compound with urea molecules, while unsaturated fatty acid (ester) is difficult to be included by urea due to the influence of double bonds, carbon chains are bent, has a certain spatial configuration, and the molecular volume is increased, so that the unsaturated fatty acid (ester) cannot be crystallized and separated out and is remained in a solvent. The urea inclusion method has the defects of large urea consumption, low product yield, difficult urea recovery and the like.
CN101747185A discloses a method for separating saturated fatty acid methyl ester from biodiesel, comprising: adding a solvent into the biodiesel, cooling while stirring, filtering to obtain a filter cake and a filtrate, and recovering the solvent from the filtrate to obtain the low-freezing biodiesel; washing the filter cake with a solvent, and recovering the solvent from the filter cake to obtain high-purity saturated fatty acid methyl ester; the ethanol content in the solvent is 60-99wt%, and the balance is acetone and/or butanone. The method has the advantages of large energy consumption in freezing and solvent recovery, high organic solvent concentration, strong volatility and high requirements on equipment, production environment and operation.
CN111777513A discloses a preparation method of high-purity methyl oleate, and relates to the technical field of methyl oleate purification. Adding urea and methyl oleate raw materials into a low-carbon alcohol solution, heating and dissolving the raw materials into a uniform solution, cooling and freezing the uniform solution, and separating out urea inclusion compounds of low-carbon chain methyl esters and saturated carbon chain methyl esters; filtering to remove the urea inclusion, and distilling and concentrating the filtrate to obtain a concentrate of methyl oleate and methyl linoleate; dissolving the concentrate into decalin, adding maleic anhydride and iodine, heating to react until methyl linoleate generates C 22 Adding sodium hydroxide solution into the tricarboxylic acid methyl ester; distilling the reaction solution obtained in S3 to remove the solvent decalin, filtering to remove C 22 Sodium tricarboxylate to obtain high-purity methyl oleate. The invention removes saturated fatty acid methyl ester in methyl oleate by a urea inclusion method, and then removes polyunsaturated fatty acid methyl ester by a reaction method, thereby obtaining high-purity methyl oleate. However, the method adopts urea and low-carbon alcohol solvent during purification, and the urea is large in dosage and difficult to recycle.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a composite embedding medium and a preparation method and application thereof. The composite embedding agent prepared by the invention has the functions of nucleation and embedding, is suitable for precipitation of saturated fatty acid methyl ester, and has less consumption compared with urea.
The preparation method of the composite embedding agent provided by the invention comprises the following stepsThe method comprises the following steps: heating long-chain dihydric alcohol to melt, adding diethanolamine and K under the condition of keeping the temperature 2 CO 3 And dehydrating agent, carrying out ultrasonic treatment, and filtering to obtain the composite embedding agent.
In the invention, the molecular general formula of the long-chain dihydric alcohol is C n H n+2 O 2 Wherein n is 10 to 18, preferably a dodecanediol.
In the invention, the heating temperature is 75-120 ℃, preferably 80-100 ℃.
In the invention, the mass ratio of the long-chain dihydric alcohol to the diethanolamine is 1.2-1.
In the present invention, said K 2 CO 3 The dosage is 1 to 10 percent of the mass of the long-chain dihydric alcohol, and the optimal dosage is 1 to 5 percent.
In the invention, the dehydrating agent is conventionally used in the field, such as water-absorbing silica gel and the like, and the dosage of the dehydrating agent is 5-20% of the mass of the long-chain dihydric alcohol, preferably 5-10%.
In the present invention, the power of the ultrasonic treatment is 50 to 300W, preferably 100 to 300W. In the present invention, the temperature of the ultrasonic treatment is 80 to 120 ℃, preferably 80 to 100 ℃.
In the invention, the stirring speed of ultrasonic treatment is 100-500 rpm, preferably 100-200 rpm; the treatment time is 1 to 5 hours, preferably 1 to 3 hours.
In the invention, the filtration can adopt the conventional filter pressing, centrifugation and other modes.
The composite embedding medium is prepared by the method. The prepared composite embedding agent is obtained by N alkylation reaction of long-chain dihydric alcohol and hydrogen on amino of diethanol amine.
The invention also provides a method for separating saturated fatty acid methyl ester from biodiesel, which is realized by adopting the composite embedding agent prepared by the invention, and the method comprises the steps of heating and mixing the composite embedding agent and the biodiesel, preserving heat for a certain time, and then cooling to 10-20 ℃ for heat preservation and crystallization.
In the method, the biodiesel mainly contains saturated fatty acid methyl ester and unsaturated fatty acid methyl ester, wherein the content of the saturated fatty acid methyl ester is higher than 25 percent, and the saturated fatty acid methyl ester can be at least one of illegal cooking oil biodiesel, palm oil biodiesel and the like.
In the method of the invention, the mass percentage of the composite embedding medium and the saturated fatty acid methyl ester in the biodiesel is 5-30%, preferably 5-20%.
In the method, the heating temperature is 40-80 ℃, the stirring speed is 100-300 rpm, and the heat preservation time is 20-120 min.
In the method, the temperature is preferably reduced to 10-20 ℃ at the speed of 0.1-5 ℃/min, and the heat preservation and crystallization time is 1-5 h.
Compared with the prior art, the invention has the following beneficial effects:
(1) Aiming at the problem of large urea consumption in the urea inclusion method, the invention adopts long-chain dihydric alcohol, diethanol amine and K 2 CO 3 The composite embedding agent is prepared by combining the ultrasonic effect, has the functions of nucleation and embedding, is suitable for precipitation of saturated fatty acid methyl ester, and has less consumption compared with urea.
(2) The composite embedding agent prepared by the invention contains more than two free hydroxyl groups in molecules, so that a three-dimensional nanofiber network with a supermolecular structure can be formed through intermolecular hydrogen bond action at a temperature above the melting point of saturated fatty acid methyl ester, the specific surface area of the embedding agent is increased, a phenomenon similar to gelation is generated, a large number of uniformly distributed crystal nuclei are formed, and crystallization and nucleation of saturated fatty acid methyl ester are promoted.
(3) The composite embedding medium prepared by the invention is particularly suitable for cooling crystallization of raw materials with high content of saturated fatty acid methyl ester, does not need additional solvent and solvent separation process, and has the advantages of easily obtained raw materials and good crystallization effect.
Detailed Description
The method and effects of the present invention will be further described in detail with reference to specific examples. The embodiments are implemented on the premise of the technical scheme of the invention, and detailed implementation modes and specific operation processes are given, but the protection scope of the invention is not limited by the following embodiments.
The experimental procedures in the following examples are, unless otherwise specified, those conventional in the art. The test materials used in the following examples were purchased from biochemical stores, unless otherwise specified.
The content of fatty acid methyl ester is analyzed by gas phase. Gas phase analysis conditions: an Agilent GC-2010 gas chromatograph is provided with a FID detector; the chromatographic column is SP-2560 type capillary column, 100m × 0.25mm × 0.20 μm. The temperature of a sample inlet is 280 ℃; the sample volume is 1 mu L; split-flow sample injection, wherein the split-flow ratio is 200; the initial column temperature is 180 ℃, the temperature is raised to 290 ℃ at the heating rate of 8 ℃/min, and the temperature is kept for 5min; the detector temperature was 280 ℃.
Example 1
Melting the dodecanediol at 85 ℃, adding diethanolamine according to the mass ratio of 1 2 CO 3 And 10% of water-absorbing silica gel by mass, treating for 2h at the ultrasonic power of 300W, the temperature of 100 ℃ and the stirring speed of 300rpm, and filtering to obtain the composite embedding agent.
Example 2
Melting the dodecanediol at 80 ℃, adding diethanolamine according to the mass ratio of 1 to 1.1 under the heat preservation state, and then adding K accounting for 1 percent of the mass of the dodecanediol 2 CO 3 And 5% of water-absorbing silica gel by mass, treating for 1h at the ultrasonic power of 200W, the temperature of 100 ℃ and the stirring speed of 300rpm, and filtering to obtain the composite embedding agent.
Example 3
Melting the dodecanediol at 120 ℃, adding diethanolamine according to the mass ratio of 1.2 to 1.2 under the heat preservation state, and then adding K accounting for 5% of the mass of the dodecanediol 2 CO 3 And 8% of water-absorbing silica gel by mass, treating for 2h at the ultrasonic power of 100W, the temperature of 120 ℃ and the stirring speed of 300rpm, and filtering to obtain the composite embedding agent.
Example 4
The difference from example 1 is that: replacing the dodecanediol with the decadiol, and melting the decadiol at 75 ℃ in an out-of-range manner to prepare the composite embedding agent.
Example 5
The difference from example 1 is that: replacing the dodecanediol with the octadecane diol, and melting the octadecane diol at the temperature of 98 ℃ to prepare the composite embedding medium.
Comparative example 1
The same as example 1, except that: and replacing the dodecanediol with ethylene glycol to prepare the composite embedding medium.
Comparative example 2
The difference from example 1 is that: replacing the dodecane diol with dodecane diacid to prepare the composite embedding agent.
Comparative example 3
The same as example 1, except that: without addition of K 2 CO 3 And preparing the composite embedding agent.
Comparative example 4
The same as example 1, except that: and (4) not adding diethanol amine to prepare the composite embedding agent.
Comparative example 5
The difference from example 1 is that: diethanolamine was replaced with triethanolamine. And preparing the composite embedding agent.
Comparative example 6
The same as example 1, except that: the composite embedding medium is prepared without ultrasonic treatment.
Test example
The composite embedding agents prepared in examples and comparative examples were used for separating saturated fatty acid methyl ester in biodiesel, and palm oil biodiesel was used, wherein the content of saturated fatty acid methyl ester was 30% and the content of unsaturated fatty acid methyl ester was 65%.
Firstly, mixing the composite embedding agent and the biodiesel, heating at 50 ℃, stirring at a speed of 200rpm, preserving heat for 30min, then cooling to 15 ℃ at a speed of 2 ℃/min, and preserving heat for crystallization for 2h. The filtrate was filtered, and the contents of saturated fatty acid methyl ester and unsaturated fatty acid methyl ester in the filtrate were measured, and the results are shown in table 1.
TABLE 1
As can be seen from the effects of Table 1, the composite embedding agent prepared by the method of the invention has the advantages of less dosage and prominent effect compared with urea.
Claims (21)
1. The preparation method of the composite embedding agent is characterized by comprising the following steps: heating long-chain dihydric alcohol to melt, adding diethanolamine and K under the condition of keeping the temperature 2 CO 3 And dehydrating agent, carrying out ultrasonic treatment, and filtering to obtain the composite embedding agent; the molecular general formula of the long-chain dihydric alcohol is C n H n+2 O 2 Wherein n is 10 to 18.
2. The method of claim 1, wherein: the long-chain dihydric alcohol is dodecane dihydric alcohol.
3. The method of claim 1, wherein: the heating and melting temperature is 75-120 ℃.
4. The method of claim 3, wherein: the heating and melting temperature is 80-100 ℃.
5. The method according to claim 1 or 2, characterized in that: the mass ratio of the long-chain dihydric alcohol to the diethanol amine is 1.2-1.
6. The method of claim 1, wherein: said K 2 CO 3 The dosage is 1 to 10 percent of the mass of the long-chain dihydric alcohol.
7. The method of claim 6, wherein: said K 2 CO 3 The dosage is 1 to 5 percent of the mass of the long-chain dihydric alcohol.
8. The method of claim 1, wherein: the dehydrating agent is water-absorbing silica gel, and the using amount of the dehydrating agent is 5-20% of the mass of the long-chain dihydric alcohol.
9. The method of claim 8, wherein: the dosage of the dehydrating agent is 5 to 10 percent of the mass of the long-chain dihydric alcohol.
10. The method of claim 1, wherein: the power of ultrasonic treatment is 50-300W, and the temperature of ultrasonic treatment is 80-120 ℃.
11. The method of claim 10, wherein: the power of the ultrasonic treatment is 100-300W, and the temperature of the ultrasonic treatment is 80-100 ℃.
12. The method according to claim 1 or 10 or 11, characterized in that: the stirring speed of ultrasonic treatment is 100-500 rpm, and the treatment time is 1-5 h.
13. The method of claim 12, wherein: the stirring speed of the ultrasonic treatment is 100-200 rpm; the treatment time is 1-3 h.
14. A composite embedding medium, characterized in that it is prepared by the process according to any one of claims 1 to 13.
15. A method for separating saturated fatty acid methyl ester from biodiesel, which is characterized in that the method is realized by adopting the composite embedding agent prepared by the method of any one of the claims 1 to 13, and the composite embedding agent and the biodiesel are heated and mixed, kept warm for a certain time, and then cooled to 10 ℃ to 20 ℃ for crystallization.
16. The method of claim 15, wherein: the biodiesel mainly contains saturated fatty acid methyl ester and unsaturated fatty acid methyl ester, wherein the content of the saturated fatty acid methyl ester is higher than 25%.
17. The method according to claim 15 or 16, characterized in that: the biodiesel is at least one of illegal cooking oil biodiesel and palm oil biodiesel.
18. The method of claim 15, wherein: the mass percentage of the composite embedding medium and the saturated fatty acid methyl ester in the biodiesel is 5-30%.
19. The method of claim 18, wherein: the mass percentage of the composite embedding medium and the saturated fatty acid methyl ester in the biodiesel is 5-20%.
20. The method of claim 15, wherein: the temperature of the heating and mixing is 40-80 ℃, the stirring speed is 100-300 rpm, and the heat preservation time is 20-120 min.
21. The method of claim 15, wherein: cooling to 10-20 ℃ at the speed of 0.1-5 ℃/min, and keeping the temperature for crystallization for 1-5 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011198158.6A CN114432729B (en) | 2020-10-30 | 2020-10-30 | Composite embedding agent and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011198158.6A CN114432729B (en) | 2020-10-30 | 2020-10-30 | Composite embedding agent and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114432729A CN114432729A (en) | 2022-05-06 |
| CN114432729B true CN114432729B (en) | 2023-03-14 |
Family
ID=81358126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011198158.6A Active CN114432729B (en) | 2020-10-30 | 2020-10-30 | Composite embedding agent and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114432729B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB738080A (en) * | 1952-05-21 | 1955-10-05 | British Cellophane Ltd | Improvements in or relating to the manufacture of regenerated cellulose films |
| US9458401B2 (en) * | 2012-03-07 | 2016-10-04 | Basf Se | Use of substituted ureas or urethanes for improvement of the use properties of mineral and synthetic nonaqueous industrial fluids |
| JP5822781B2 (en) * | 2012-04-27 | 2015-11-24 | 株式会社Adeka | Low temperature fluidity improver for fatty acid methyl ester, biodiesel fuel composition containing the low temperature fluidity improver, and method for producing the low temperature fluidity improver |
| CN102702009A (en) * | 2012-06-11 | 2012-10-03 | 科凯精细化工（上海）有限公司 | Method for synthesizing diethanol amide |
| CN102796237B (en) * | 2012-08-31 | 2014-01-29 | 合肥安科精细化工有限公司 | Dihydroxyl cationic hydrophilic chain extender and application thereof in synthesis of cationic aqueous polyurethane dispersoid |
| US9834734B2 (en) * | 2014-05-23 | 2017-12-05 | Taminco Bvba | Acid gas removal process by absorbent solution comprising amine compounds |
| EP3623527A1 (en) * | 2015-07-10 | 2020-03-18 | The Procter & Gamble Company | Fabric care composition comprising metathesized unsaturated polyol esters |
| JP6811560B2 (en) * | 2016-07-25 | 2021-01-13 | 株式会社シャネル化粧品技術開発研究所 | A multi-phase emulsion in which a water-in-oil emulsion is dispersed in an outer phase having both continuous structures and a method for producing the same. |
-
2020
- 2020-10-30 CN CN202011198158.6A patent/CN114432729B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN114432729A (en) | 2022-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106928285B (en) | Method for preparing levoglucosenone by catalytic pyrolysis of biomass | |
| CN113648834B (en) | Ceramic membrane and preparation method and application thereof | |
| CN114432729B (en) | Composite embedding agent and preparation method and application thereof | |
| WO2016192239A1 (en) | Environmentally-friendly extraction and purification method of natural cinnamic aldehyde | |
| CN112745969B (en) | Method for preparing fatty acid type diesel oil antiwear agent by low-temperature freezing | |
| CN107286270A (en) | A kind of method that utilization enzymatic isolation method prepares liquaemin | |
| CN114621097B (en) | Method for preparing 2, 4-difluoroaniline by catalytic hydrogenation of 2, 4-difluoronitrobenzene | |
| CN107754827B (en) | Supported solid base catalyst and preparation method and application thereof | |
| CN113666837B (en) | Preparation method of 1, 4-dimethyl pentylamine hydrochloride | |
| CN108707071A (en) | A kind of method that propionic aldehyde oxidation prepares propionic acid | |
| CN112322350B (en) | Method for preparing high enthalpy value phase-change wax from Fischer-Tropsch synthesis product | |
| CN114181778A (en) | Preparation method of ruminant trans-fatty acid | |
| CN114853593A (en) | Method for extracting high-purity nervonic acid from acer truncatum buge oil | |
| CN102924396B (en) | Method for crystal transformation from alpha-HMX to beta-HMX | |
| CN107384491B (en) | A kind of preparation method of high-efficiency diesel pour inhibitor | |
| CN111349037B (en) | Monoacid type aviation fuel antiwear agent and preparation method thereof | |
| CN112745987B (en) | Saturated fatty acid crystallization aid and preparation method thereof | |
| CN1634845A (en) | Process for producing ibuprofen microcrystal | |
| CN114806616B (en) | Method for pretreating biomass raw material by using freeze-thawing auxiliary eutectic solvent to improve pyrolysis oil quality and application | |
| CN102504958B (en) | Method for separating unsaturated fatty acids from silkworm chrysalis oil based on composition complexation of reversible reaction | |
| CN104788307A (en) | Method for purifying sorbic acid | |
| CN105779161A (en) | Preparation method of paraffin remover | |
| CN103772224B (en) | Preparation method of D-threonine | |
| CN115385780B (en) | Secondary cannabidiol crystal polymorph and preparation method and application thereof | |
| CN109289930A (en) | A method of efficiently separating and purify 1- methyl naphthalene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20231122 Address after: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Patentee after: CHINA PETROLEUM & CHEMICAL Corp. Patentee after: Sinopec (Dalian) Petrochemical Research Institute Co.,Ltd. Address before: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Patentee before: CHINA PETROLEUM & CHEMICAL Corp. Patentee before: DALIAN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC Corp. |