CN1544413A - Methyl eicosapentaenoic acid preparing and purifying method from pavlova viridis - Google Patents
Methyl eicosapentaenoic acid preparing and purifying method from pavlova viridis Download PDFInfo
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- CN1544413A CN1544413A CNA2003101063993A CN200310106399A CN1544413A CN 1544413 A CN1544413 A CN 1544413A CN A2003101063993 A CNA2003101063993 A CN A2003101063993A CN 200310106399 A CN200310106399 A CN 200310106399A CN 1544413 A CN1544413 A CN 1544413A
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- China
- Prior art keywords
- acetone
- eicosapentaenoic acid
- normal hexane
- methyl
- pavlova viridis
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- 235000020673 eicosapentaenoic acid Nutrition 0.000 title claims description 30
- -1 Methyl eicosapentaenoic acid Chemical compound 0.000 title claims description 24
- 229960005135 eicosapentaenoic acid Drugs 0.000 title claims description 23
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims description 21
- 241000386616 Pavlova viridis Species 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 10
- 239000007788 liquid Substances 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 239000000741 silica gel Substances 0.000 claims description 19
- 229910002027 silica gel Inorganic materials 0.000 claims description 19
- 229960001866 silicon dioxide Drugs 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 16
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 241000195493 Cryptophyta Species 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 5
- 239000012154 double-distilled water Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 230000010355 oscillation Effects 0.000 claims description 4
- 238000012856 packing Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004202 carbamide Substances 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000012065 filter cake Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 abstract 1
- 238000001291 vacuum drying Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 3
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- 241000143060 Americamysis bahia Species 0.000 description 1
- 241000206751 Chrysophyceae Species 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a process for preparing Trifluralin - a herbicide with high content by using 3,5- binitro-4-chlorobenzotrifluoride and ortho-dipropyl amine as raw material, and alkali as catalyst, through the steps of diluting 3,5-binitro-4-chlorobenzotrifluoride with water solution of alkali in a reactor, agitating, charging in turn water solutions of urea, thiocarbamide and surface active agent, dropping slowly alkali liquid and ortho-dipropyl amine while controlling reaction temperature, maintaining reaction temperature, agitating inverse flow 1-2h, quit heating and continuing agitating, cooling down to room temperature, stewing and filtering, and vacuum drying the filter cake.
Description
Technical field
The present invention relates to Ba Fuzao and timnodonic acid, specifically, relate to prepare the method for methyl eicosapentaenoic acid from crust husband algae.
Background technology
Pavlova viridis (Pavlova viridis) is a kind of yellowish green small chrysophyceae.Frond ovalize or circle, acellular wall.The about 4-6 μ of this frustule diameter m can move, and is that a kind of comfort zone is wide, and illumination requires the low little algae of single-cell sea.The good bait of the Chang Zuowei shrimps young and economic shellfish.The pavlova viridis that studies show that in recent years is rich in timnodonic acid polyunsaturated fatty acids such as (Eicosapentaenoic acid call EPA in the following text), and its EPA content accounts for the 12-15% (changing according to the culture condition difference) of total fat.
Polyunsaturated fatty acids such as EPA are present in the alga cells glycolipid, and obtain methyl eicosapentaenoic acid generally at first needs to extract total ester from crust husband algae, and saponification makes it into free acid, carries out esterification then, and separation, purifying obtain methyl eicosapentaenoic acid at last.Separation, purifying mainly contain low-temperature freezing, urea adduct method, molecular distillation method, supercritical CO
2Extraction process etc.But yield and the purity of these methods or EPA are lower, and perhaps cost is too high.
Summary of the invention
The purpose of this invention is to provide the method that a kind of step is simple, cost is low, purity is high, yield is high from pavlova viridis preparation and purifying methyl eicosapentaenoic acid.
Technical scheme of the present invention is as follows:
A kind of method from pavlova viridis preparation and purifying methyl eicosapentaenoic acid, it comprises the following steps:
Step 1. in the container of packing into, adds 20N～30N milliliter 5% chloracetyl-methyl alcohol (promptly 1: 20 v/v) with pavlova viridis freeze-dried algae powder N gram, and is airtight behind the inflated with nitrogen, reacts 0.5～2 hour down in 80-100 ℃, is cooled to room temperature,
Step 2. adds the double distilled water and the normal hexane of equal volume respectively in the reaction mixture of step 1 gained, oscillation extraction, draw supernatant liquid after, add the normal hexane re-extract of equivalent again, no longer turn to be yellow to supernatant liquor,
Behind step 3. combining extraction liquid, use the siccative drying, the elimination siccative boils off normal hexane under nitrogen protection, obtains fatty acid methyl ester 0.046N～0.07N gram,
Step 4. is carried out chromatography with the fatty acid methyl ester that step 3 obtains with being coated with silver-colored silicagel column, with acetone-hexane solution gradient elution, collects elutriant respectively, and merging contains methyl eicosapentaenoic acid purity and is higher than 95% elutriant,
In the above-mentioned preparation and the step 4 of purification process, acetone-hexane solution gradient elution can be respectively is acetone-hexane solution of 0.5%, 1%, 5%, 10% and 15% wash-out successively with the acetone concentration expressed in percentage by volume.
In the above-mentioned preparation and the step 4 of purification process, being coated with the silver-colored silica gel of being coated with of silver-colored silicagel column can be prepared as follows:
A certain amount of silica gel for chromatography is added in the two volumes dehydrated alcohol, mix into suspension.Silver Nitrate is dissolved in an amount of 70% ethanol, and it is even to add above-mentioned chromatographic silica gel thorough mixing.The weight ratio of Silver Nitrate and silica gel is 1: 10.Boil off ethanol then, the silver-colored silica gel of being coated with of gained is placed baking oven,, after the cooling, preserve in the dark place in 120 ℃ of high-temperature activations (more than 12 hours).
Method steps from pavlova viridis preparation and purifying methyl eicosapentaenoic acid of the present invention is simple, consumes and lacks, and cost is low, the yield height, and yield can reach 65～72% of theoretical value, the purity height, purity can reach more than 95%.
Description of drawings
Fig. 1 is coated with silver-colored silica gel column chromatography-gradient concentration elutriant among the embodiment 2, the gas chromatogram of 15% acetone-normal hexane first pipe elutriant, and wherein the retention time and the peak area at a peak are as follows:
Peak?RetTime?Type?Width Area Height Area
# [min] [min] [pA*s] [pA] ％
----|-------|----|-------|----------|----------|--------|
1 14.148?PB 0.0681 4.08046 7.91750e-1?0.42113
2 15.930?PP 0.0667 7.70089 1.64221 0.79478
3 18.151?PB 0.0636 923.32898?187.03178 95.29351
4 18.589?PB 0.0624 3.55124 6.86098e-1?0.36651
5 19.541?BB 0.0718 10.97733 1.88797 1.13293
6 21.027?BB 0.0713 14.81180 2.86513 1.52867
7 21.685?PV 0.0640 2.02365 3.86956e-1?0.20885
8 22.399?PV 0.0702 2.45727 4.26771e-1?0.25361
Totals： 968.93161?195.71867
Fig. 2 is coated with silver-colored silica gel column chromatography-gradient concentration elutriant among the embodiment 2, the gas chromatogram of 15% acetone-normal hexane second pipe elutriant, and wherein the retention time and the peak area at a peak are as follows:
Peak?RetTime?Type Width Area Height Area
# [min] [min] [pA*s] [pA] ％
----|-------|----|-------|----------|----------|--------|
1 14.155?PB 0.0659 2.07125 3.90620e-1?0.38716
2 15.945?BB 0.0682 4.44554 9.56831e-1?0.83097
3 18.143?PB 0.0714 517.56049?105.23692 96.74304
4 19.557?BP 0.0857 6.76244 1.01491 1.26404
5 21.044?PB 0.0622 1.90134 3.80979e-1?0.35540
6 22.405?BB 0.0742 2.24367 3.67851e-1?0.41939
Totals： 534.98472?108.34811
Results?obtained?with?enhanced?integrator！
Fig. 3 is coated with silver-colored silica gel column chromatography-gradient concentration elutriant among the embodiment 2, the gas chromatogram of 15% acetone-normal hexane the 3rd pipe elutriant, and wherein the retention time and the peak area at a peak are as follows:
Peak RetTime?Type Width Area Height Area
# [min] [min] [pA*s] [pA] ％
----|-------|----|-------|----------|----------|--------|
1 15.952 BP 0.0648 2.47534 5.27118e-1?0.86594
2 18.134 BB 0.0774 278.85254 55.68338 97.54986
3 19.563 BB 0.0858 4.52853 6.54070e-1?1.58420
Totals： 285.85641 56.86457
Results?obtained?with?enhanced?integrator！
Fig. 4 is coated with silver-colored silica gel column chromatography-gradient concentration elutriant among the embodiment 2, the gas chromatogram of 15% acetone-normal hexane the 4th and the 5th pipe elutriant, and wherein the retention time and the peak area at a peak are as follows:
Peak?RetTime?Type Width Area Height Area
# [min] [min] [pA*s] [pA] ％
----|-------|----|-------|----------|----------|--------|
1 18.129?PB 0.0772 136.59071 27.39506 97.74114
2 19.570?BP 0.1351 3.15670 2.83150e-1?2.25886
Totals： 139.74741 27.67821
Results?obtained?with?enhanced?integrator！
Embodiment
Embodiment 1. algae culture and results
The little algae pavlova viridis of single-cell sea is cultivated through this laboratory rejuvenation available from Chinese Academy of Sciences marine laboratory, Qingdao, is stored in 21-27 ℃.Culture condition is as follows: 6000-9000lux, 12:12L/D, aerated culture.Exponential growth results in latter stage were collected frond in the centrifugal 8-15 of 4000-8000g minute, and distilled water wash is to remove salt and other impurity, lyophilize, cryogenic freezing preservation.
Embodiment 2. is coated with the preparation of silver-colored silicagel column:
A certain amount of silica gel for chromatography is added in the two volumes dehydrated alcohol, mix into suspension.Silver Nitrate is dissolved in an amount of 70% ethanol, and it is even to add above-mentioned chromatographic silica gel thorough mixing.The weight ratio of Silver Nitrate and silica gel is 1: 10.Boil off ethanol then, the silver-colored silica gel of being coated with of gained is placed baking oven,, after the cooling, preserve in the dark place in 120 ℃ of high-temperature activations (more than the 12h).
Embodiment 3. is from pavlova viridis preparation and purifying methyl eicosapentaenoic acid
From pavlova viridis preparation and purifying methyl eicosapentaenoic acid, it comprises the following steps:
Step 1. is pavlova viridis freeze-dried algae powder 1.0 gram, in the screw-cap test tube of packing into, adds 20 milliliters of 5% chloracetyl-methyl alcohol (promptly 1: 20v/v) airtight behind the inflated with nitrogen, reacted 2 hours in 80 ℃ times, be cooled to room temperature,
Step 2. adds the double distilled water and the normal hexane of equal volume respectively in the reaction mixture of step 1 gained, oscillation extraction, draw supernatant liquid after, add the normal hexane re-extract of equivalent again, no longer turn to be yellow to supernatant liquor,
Behind step 3. combining extraction liquid, use the siccative drying, the elimination siccative boils off normal hexane under nitrogen protection, obtains fatty acid methyl ester 0.046 gram,
Step 4. is carried out chromatography with the fatty acid methyl ester that step 3 obtains with being coated with silver-colored silicagel column, be 0.5% with acetone concentration respectively, 1%, 5%, each 25ml of the acetone-hexane solution of 10%, 15% (v/v) is by concentration wash-out successively from low to high, and flow rate control is at 1.3～2.0ml/min, every 5ml collects a pipe, collects the effluent liquid of each different concns gradient respectively and does the GC analysis.Find when the acetone concentration of acetone-normal hexane elutriant is lower than 10%, some saturated and low fatty acid methyl ester and other impurity of degree of unsaturation can be eluted substantially fully, EPA begins wash-out and comes out in last when pipe of 10% acetone-normal hexane, when the elutriant acetone concentration reaches 15% (v/v), obtaining purity successively is 95.29%, 96.74%, the EPA methyl esters (seeing gas chromatogram, Fig. 1-4) of 97.55%, 97.74% (the 4th and the 5th pipe elutriant of merging).The elutriant that merges 15% acetone-normal hexane can obtain purity greater than 95% EPA methyl esters, and yield is about 60%.
Embodiment 4. is from pavlova viridis preparation and purifying methyl eicosapentaenoic acid
From pavlova viridis preparation and purifying methyl eicosapentaenoic acid, it comprises the following steps:
Step 1. is pavlova viridis freeze-dried algae powder 1.0 gram, in the screw-cap test tube of packing into, adds 30 milliliters of 5% chloracetyl-methyl alcohol (promptly 1: 20v/v) airtight behind the inflated with nitrogen, reacted 0.5 hour in 100 ℃ times, be cooled to room temperature,
Step 2. adds the double distilled water and the normal hexane of equal volume respectively in the reaction mixture of step 1 gained, oscillation extraction, draw supernatant liquid after, add the normal hexane re-extract of equivalent again, no longer turn to be yellow to supernatant liquor,
Behind step 3. combining extraction liquid, use the siccative drying, the elimination siccative boils off normal hexane under nitrogen protection, obtains fatty acid methyl ester 0.07 gram,
Step 4. is carried out chromatography with the fatty acid methyl ester that step 3 obtains with being coated with silver-colored silicagel column, with acetone-hexane solution gradient elution, collects elutriant with embodiment respectively, and merging contains methyl eicosapentaenoic acid purity and is higher than 95% elutriant,
Claims (2)
1. the method from pavlova viridis preparation and purifying methyl eicosapentaenoic acid is characterized in that it comprises the following steps:
Step 1. in the container of packing into, adds pavlova viridis freeze-dried algae powder N gram 20N～30N ml volumes percentage concentration and is chloracetyl-methyl alcohol of 5%, and is airtight behind the inflated with nitrogen, reacts 0.5～2 hour down in 80-100 ℃, is cooled to room temperature,
Step 2. adds the double distilled water and the normal hexane of equal volume respectively in the reaction mixture of step 1 gained, oscillation extraction, draw supernatant liquid after, add the normal hexane re-extract of equivalent again, no longer turn to be yellow to supernatant liquor,
Behind step 3. combining extraction liquid, use the siccative drying, the elimination siccative boils off normal hexane under nitrogen protection, obtain fatty acid methyl ester,
Step 4. is carried out chromatography with the fatty acid methyl ester that step 3 obtains with being coated with silver-colored silicagel column, with acetone-hexane solution gradient elution, collects elutriant respectively, and merging contains methyl eicosapentaenoic acid purity and is higher than 95% elutriant,
Step 5. boils off acetone and normal hexane under nitrogen protection, promptly get methyl eicosapentaenoic acid, and purity is higher than 95%.
2. preparation according to claim 1 and purification process, it is characterized in that: in step 4, acetone-hexane solution gradient elution can be respectively is acetone-hexane solution of 0.5%, 1%, 5%, 10% and 15% wash-out successively with the acetone concentration expressed in percentage by volume.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200310106399.3A CN1233616C (en) | 2003-11-24 | 2003-11-24 | Methyl eicosapentaenoic acid preparing and purifying method from pavlova viridis |
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| CN200310106399.3A CN1233616C (en) | 2003-11-24 | 2003-11-24 | Methyl eicosapentaenoic acid preparing and purifying method from pavlova viridis |
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| CN1233616C CN1233616C (en) | 2005-12-28 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102517156A (en) * | 2011-12-31 | 2012-06-27 | 中国海洋大学 | High-efficiency quick preparation method of microalgae fatty acid methyl ester |
| US8591825B2 (en) | 2011-05-18 | 2013-11-26 | Industrial Technology Research Institute | Extraction apparatus |
| CN104195148A (en) * | 2014-09-16 | 2014-12-10 | 合肥工业大学 | Green pavlova viridis delta-5 desaturase gene for EPA (Eicosapentaenoic Acid) synthesis and preparation method of green pavlova viridis delta-5 desaturase gene |
-
2003
- 2003-11-24 CN CN200310106399.3A patent/CN1233616C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8591825B2 (en) | 2011-05-18 | 2013-11-26 | Industrial Technology Research Institute | Extraction apparatus |
| CN102517156A (en) * | 2011-12-31 | 2012-06-27 | 中国海洋大学 | High-efficiency quick preparation method of microalgae fatty acid methyl ester |
| CN104195148A (en) * | 2014-09-16 | 2014-12-10 | 合肥工业大学 | Green pavlova viridis delta-5 desaturase gene for EPA (Eicosapentaenoic Acid) synthesis and preparation method of green pavlova viridis delta-5 desaturase gene |
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| Publication number | Publication date |
|---|---|
| CN1233616C (en) | 2005-12-28 |
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