CN101220018A - Method for separating single tocopherol from mixed tocopherol - Google Patents
Method for separating single tocopherol from mixed tocopherol Download PDFInfo
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- CN101220018A CN101220018A CNA2008100594841A CN200810059484A CN101220018A CN 101220018 A CN101220018 A CN 101220018A CN A2008100594841 A CNA2008100594841 A CN A2008100594841A CN 200810059484 A CN200810059484 A CN 200810059484A CN 101220018 A CN101220018 A CN 101220018A
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Abstract
The invention relates to a method for separating single tocopherol from mixed tocopherol, which takes the mixed tocopherol with a content of 50 percent to 100 percent as a raw material and adopts a four-area simulated moving bed chromatography system to separate a d-alpha-tocopherol, a d-beta-tocopherol, a d-gamma-tocopherol and a d-delta tocopherol with the purity and yield all more than 98 percent. As the simulated moving bed chromatography separation is a continuous process, the method has the advantages of high degree of production automation, simple technique, high production efficiency, continuous production and stable product quality. As an adsorbent and a solvent have low consumption, the whole separating device does not relate to chemical reactions.
Description
Technical field
The present invention relates to chemical separation technology, especially relate to a kind of from mixed tocopherol the method for separating single tocopherol.
Background technology
Natural VE (formal name used at school tocopherol) is a kind of mixture, four kinds of tocopherol homologues of mainly being derived by tocol (Tocol) and coming are formed, comprise: d-α-, d-β-, d-γ-and d-Delta-Tocopherol, they all have saturated C16 side chain, only exist difference on the number of methyl on the phenyl ring and position.Though their structure is extremely similar, biological activity is inequality, wherein: d-alpha-tocopherol (activity is 100)＞d-5,8-dimethyl tocol (activity is 10～50)＞d-Gamma-Tocopherol (activity is 10)＞d-Delta-Tocopherol (activity is 1).
Natural VE is used as a kind of antioxidant and accessory substance is widely used in medicine, makeup and the foodstuffs industry, and it all is better than synthesising complex E on biological activity, nutritional-physiological effect and safety in utilization.But the content of mixed tocopherol only is 0.04%-0.1% in the vegetables oil, directly extracts tocopherol as raw material and does not still have industrial application value.And the by product that produces in edible vegetable oil (salad oil) refining process---the content of tocopherol generally is higher than 2.5% in the deodorization distillate, and therefore therefrom extracting tocopherol has more using value.
Natural VE is a raw material with the soybean oil overhead product generally, through chemical processes such as pre-treatment, fractionation by adsorption, methylol hydrogenation transition, molecular distillation or chromatographic refinings, purifies and is re-dubbed various different size natural VEs.As CN 1401644, CN 1401645, and CN 1603321 routes such as adopting process such as grade are as follows:
Most of document about natural VE, as US 2486539, US 2486542, and EP 0159018, and US 4239691, EP 0178400, the spy open clear 60-237085 etc. all adopt reaction transition with β-, γ-and Delta-Tocopherol change into tocopherol owing to produced chemical reaction in process of production, reduced the specific rotatory power of vitamin-E product, partial destruction original physiologically active of vitamin-E and natural attribute, can only be referred to as " half-natural " vitamin-E.Recently report also that Gamma-Tocopherol has anti-inflammatory action.Therefore, direct separation and purification tocopherol homologues has Research Significance and economic benefit from mixed tocopherol.
US 3402183, and US 2005/131240 adopts ion exchange resin to separate mixed tocopherol, obtained highly purified α-, γ-and Delta-Tocopherol, because the tocopherol textural difference is very little, need to consume a large amount of resin and solvent, separation costs is too high, can't realize industrialization; US 4480108, and US 4602098, US 4607111 grades adopt d-α-, d-β-, d-γ-different with the complexity of d-Delta-Tocopherol esterification, on ion exchange resin, separated tocopherol homologues.
Simulated moving bed chromatography (Simulated moving bed chromatography, SMBC) isolation technique is a kind of novel modern chemistry isolation technique that grows up the sixties in 20th century, in the preparative chromatography technology, be applicable to and carry out the continuity large-scale industrial production, it is to be operating unit with the chromatogram, some root chromatogram columns are joined end to end with rotary valve, all be provided with into before and after every root chromatogram column, outlet, utilize rotary valve to switch termly successively along the moving phase direction, thereby change the position of sample inlet and products export, simulate with this that adverse current moves between stationary phase and the moving phase, finally realize the continuous separation of two kinds of compositions.Recently, the SMBC device in also useful 8 districts and 16 districts separates multi-component material, but along with the increase of distinguishing number, the influence of the complicacy of system and polycomponent competitive adsorption also increases, and is unfavorable for the stably manufactured of SMBC, and therefore, most of SMBC still adopts 4 districts.Fig. 1 is 4 common district SMBC synoptic diagram.
It is strong that SMBC has separating power, and device structure is little, is convenient to automatic control, and be particularly conducive to that to separate thermo-sensitivity high and be difficult to advantage such as separation mixture, compares with common preparative chromatography, also has advantages such as serialization, sorbent material and moving phase consumption are few.The SMBC adsorption separation technology has not only overcome the shortcoming of the periodical operation of ADSORPTION IN A FIXED BED isolation technique existence, also overcome the excessive shortcoming of adsorbent attrition that the moving-bed adsorption separation technology exists, realized the production process serialization, the product purity and the rate of recovery can reach comparatively ideal level simultaneously.SMBC technology range of application spreads all over fields such as oil, carbohydrate, fermentation organic acid and amino acid.Especially since the nineties, the SMBC technology begins to be applied to separating of fine chemistry industry and medicine especially chiral drug.But SMBC separation and purification tocopherol homologues does not appear in the newspapers as yet.
Summary of the invention
The object of the present invention is to provide a kind of from mixed tocopherol the method for separating single tocopherol.Be to be raw material with mixed tocopherol (mixed tocopherol content 50%～100%), adopt simulated moving bed chromatography isolate highly purified d-α-, d-β-, d-γ-and d-Delta-Tocopherol.
The technical solution adopted for the present invention to solve the technical problems is:
With content is that 50%～100% mixed tocopherol is a raw material, adopt simulated moving bed chromatography isolate highly purified d-α-, d-β-, d-γ-and d-Delta-Tocopherol.
The present invention specifically may further comprise the steps:
(1) mixed tocopherol is dissolved in moving phase, concentration is 1mg/mL～300mg/mL;
(2) from simulated moving bed chromatography system, isolate the tocopherol monomer successively;
(3) steam and to desolventize, obtain purity and yield all be higher than 98% d-α-, d-β-, d-γ-and d-Delta-Tocopherol.
The total pillar number of described simulated moving bed chromatography is 4～32, and every district pillar number is 1～8.
The optimum total pillar number of described simulated moving bed chromatography is 8～16, and the optimum pillar number in every district is 2～4.
Described moving phase is normal hexane, sherwood oil, methyl alcohol, ethanol, Virahol, acetone, ethyl acetate or its mixed solvent system.
Described stationary phase is gac, silica gel, activated alumina.
The service temperature of described simulated moving bed chromatography system is 10～60 ℃.
The optimum service temperature of the service temperature of described simulated moving bed chromatography system is 20～50 ℃.
The beneficial effect that the present invention has is:
Comprise five components in the mixed tocopherol: non-tocopherol impurity, d-alpha-tocopherol, d-5,8-dimethyl tocol, d-Gamma-Tocopherol and d-Delta-Tocopherol.Earlier the absorbed component of the strongest (or the most weak) is separated with other component, then remaining component is carried out the SMBC separation second time, separate, promptly carry out 4 SMBC and separate, obtained 5 pure components up to carrying out-1 SMBC of n (total number of components).Steaming desolventizes, obtain purity and yield all be higher than 98% d-α-, d-β-, d-γ-and d-Delta-Tocopherol.Because it is successive processes that simulated moving bed chromatography is separated, so the production automation degree height of present method, technology is simple, and the production efficiency height is produced continuously constant product quality.Sorbent material and solvent consumption are low, and whole sepn process does not relate to chemical reaction.
Embodiment
The method of separating single tocopherol is from mixed tocopherol:
1. adopt simulated moving bed chromatography (being called for short SMBC) system, this system comprises sampling pump, wash-out liquid pump, extracts pump, puies forward surplus pump, rotary valve and chromatographic column, as shown in Figure 1.There are 4 districts in the SMBC system, every district 1～8 root chromatogram column (among the figure being 3), feeding liquid is from injecting between 2 districts and 3 districts, and weak absorbed component (raffinate) is collected between 3 districts and 4 districts, strong absorbed component (extracting solution) is collected between 1 district and 2 districts, and elutriant is from injecting between 4 districts and 1 district.Among the figure 1,2,3 ..., j-1, j represent the chromatographic column numbering.At regular intervals, sample introduction liquid and elutriant inlet, extracting solution and raffinate outlet switch to next root chromatogram column outlet (being clockwise direction shown in the figure) along the moving phase flow direction simultaneously.
2. chromatographic column filler and moving phase are selected
Stationary phase is gac, silica gel, activated alumina, High Pressure Wet dress post; Moving phase is normal hexane, sherwood oil, methyl alcohol, ethanol, Virahol, acetone, ethyl acetate or its mixed solvent system.
3. separating step
Contain in the mixed tocopherol d-α-, d-β-, d-γ-, d-Delta-Tocopherol and impurity.Tocopherol homologues is dissolved in moving phase, and concentration is 1mg/mL～300mg/mL; The total pillar number of simulated moving bed chromatography is 4～32, and every district pillar number is 1～8 (optimum total pillar number is 8～16, and the optimum pillar number in every district is 2～4); The service temperature of system is 10～60 ℃ (optimum service temperature is 20～50 ℃).
Embodiment 1:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with silica gel for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be normal hexane/ethanolic soln (99.5/0.5, v/v), 30 ℃ of temperature.The mixed tocopherol purity that charging is used is 97.5%, wherein contains alpha-tocopherol 22.8%, 5,8-dimethyl tocol 2.8%, Gamma-Tocopherol 34.7% and Delta-Tocopherol 37.2%, and mixed tocopherol is made into the 30.58mg/ml feedstock solution with moving phase.
A, operational condition
Sample introduction flow velocity: U
F=1ml/min
Eluent flow rate: U
D=2.8ml/min
Raffinate flow velocity: U
R=2.0ml/min
Extracting solution flow velocity: U
E=1.8ml/min
1 district's flow velocity: U
E=6.4ml/min
Switching time: t
s=757s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Delta-Tocopherol purity and yield are respectively 98.9% and 98.4% in the extracting solution, and every liter of stationary phase per hour can be produced Delta-Tocopherol 2.72g, and every production 1g Delta-Tocopherol consumes 0.25 liter of moving phase.
Embodiment 2:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with powder activated carbon for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be normal hexane/methanol solution (99.5/0.5, v/v), 30 ℃ of temperature.The mixed tocopherol purity that charging is used is 97.5%, wherein contains alpha-tocopherol 22.8%, 5,8-dimethyl tocol 2.8%, Gamma-Tocopherol 34.7% and Delta-Tocopherol 37.2%, and mixed tocopherol is made into the 30.58mg/ml feedstock solution with moving phase.
A, operational condition
Sample introduction flow velocity: U
F=1ml/min
Eluent flow rate: U
D=2.6ml/min
Raffinate flow velocity: U
R=1.8ml/min
Extracting solution flow velocity: U
E=2.0ml/min
1 district's flow velocity: U
E=6.7ml/min
Switching time: t
s=720s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Delta-Tocopherol purity and yield are respectively 99.3% and 98.9% in the extracting solution, and every liter of stationary phase per hour can be produced Delta-Tocopherol 2.73g, and every production 1g Delta-Tocopherol consumes 0.23 liter of moving phase.
Embodiment 3:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with activated alumina for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be n-hexane/acetone solution (99/1, v/v), 30 ℃ of temperature.The mixed tocopherol purity that charging is used is 97.5%, wherein contains alpha-tocopherol 22.8%, 5,8-dimethyl tocol 2.8%, Gamma-Tocopherol 34.7% and Delta-Tocopherol 37.2%, and mixed tocopherol is made into the 30.58mg/ml feedstock solution with moving phase.
A, operational condition
Sample introduction flow velocity: U
F=1ml/min
Eluent flow rate: U
D=3.1ml/min
Raffinate flow velocity: U
R=2.2ml/min
Extracting solution flow velocity: U
E=1.9ml/min
1 district's flow velocity: U
E=6.9ml/min
Switching time: t
s=708s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Delta-Tocopherol purity and yield are respectively 99.5% and 99.5% in the extracting solution, and every liter of stationary phase per hour can be produced Delta-Tocopherol 2.75g, and every production 1g Delta-Tocopherol consumes 0.27 liter of moving phase.
Embodiment 4:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with activated alumina for ID2 * 5cm), 4 in every district, High Pressure Wet dress post to assemble 16 root chromatogram columns.Moving phase be petrol ether/ethyl acetate solution (99/1, v/v), 40 ℃ of temperature.The mixed tocopherol purity that charging is used is 97.5%, wherein contains alpha-tocopherol 22.8%, 5,8-dimethyl tocol 2.8%, Gamma-Tocopherol 34.7% and Delta-Tocopherol 37.2%, and mixed tocopherol is made into the 30.58mg/ml feedstock solution with moving phase.
A, operational condition
Sample introduction flow velocity: U
F=1ml/min
Eluent flow rate: U
D=2.8ml/min
Raffinate flow velocity: U
R=2.0ml/min
Extracting solution flow velocity: U
E=1.8ml/min
1 district's flow velocity: U
E=6.4ml/min
Switching time: t
s=378s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Delta-Tocopherol purity and yield are respectively 99.2% and 99.4% in the extracting solution, and every liter of stationary phase per hour can be produced Delta-Tocopherol 2.73g, and every production 1g Delta-Tocopherol consumes 0.24 liter of moving phase.
Embodiment 5:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with silica gel for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be normal hexane/aqueous isopropanol (99/1, v/v), 30 ℃ of temperature.Delta-Tocopherol is separated fully as extracting solution in the example 1～4, also contain the charging of alpha-tocopherol, 5,8-dimethyl tocol, Gamma-Tocopherol and small amount of impurities in the remaining raffinate as this experiment, mixed tocopherol content is 96.0%, wherein alpha-tocopherol 36.3%, 5,8-dimethyl tocol 4.5%, Gamma-Tocopherol 55.2% and impurity 2.5%.Mixed tocopherol concentration is 19.28mg/ml in the feedstock solution.
A, operational condition
Sample introduction flow velocity: U
F=1ml/min
Eluent flow rate: U
D=2.8ml/min
Raffinate flow velocity: U
R=2.0ml/min
Extracting solution flow velocity: U
E=1.8ml/min
1 district's flow velocity: U
E=6.4ml/min
Switching time: t
s=535s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Gamma-Tocopherol purity and yield are respectively 99.5% and 99.0% in the extracting solution, and it is 2.54g that every liter of stationary phase per hour can be produced Gamma-Tocopherol, and every production 1g Gamma-Tocopherol consumes 0.26 liter of moving phase.
Embodiment 6:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with silica gel for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be normal hexane/aqueous isopropanol (99/1, v/v), 30 ℃ of temperature.Gamma-Tocopherol is separated fully as extracting solution in the example 5, also contain the charging of alpha-tocopherol, 5,8-dimethyl tocol and small amount of impurities in the remaining raffinate as this experiment, mixed tocopherol content is 91.0%, wherein alpha-tocopherol 81.0%, 5,8-dimethyl tocol 10.0% and impurity 9%.Mixed tocopherol concentration is 14.20mg/ml in the feedstock solution.
A, operational condition
Sample introduction flow velocity: U
F=0.2ml/min
Eluent flow rate: U
D=2.6ml/min
Raffinate flow velocity: U
R=1.4ml/min
Extracting solution flow velocity: U
E=1.4ml/min
1 district's flow velocity: U
E=6.5ml/min
Switching time: t
s=720s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.5,8-dimethyl tocol purity and yield are respectively 98.5% and 98.0% in the extracting solution, and it is 0.07g that every liter of stationary phase per hour can be produced 5,8-dimethyl tocol, and every production 1g 5,8-dimethyl tocol consumes 9.20 liters of moving phases.
Embodiment 7:
Simulated moving bed system CSEP
_916 (Nore, Germany), (chromatographic column is filled with silica gel for ID2 * 10cm), 2 in every district, High Pressure Wet dress post to assemble 8 root chromatogram columns.Moving phase be normal hexane/aqueous isopropanol (99/1, v/v), 30 ℃ of temperature.5,8-dimethyl tocol is separated fully as extracting solution in the example 6, also contains the charging as this experiment of alpha-tocopherol and impurity in the remaining raffinate, wherein alpha-tocopherol 90.0%, impurity 10.0%.Mixed tocopherol concentration is 10.50mg/ml in the feedstock solution.
A, operational condition
Sample introduction flow velocity: U
F=0.5ml/min
Eluent flow rate: U
D=2.8ml/min
Raffinate flow velocity: U
R=1.5ml/min
Extracting solution flow velocity: U
E=1.8ml/min
1 district's flow velocity: U
E=6.6ml/min
Switching time: t
s=720s
B, check analysis
Analyze raffinate and extracting solution composition with silicagel column.Alpha-tocopherol purity and yield are respectively 98.0% and 98.0% in the extracting solution, and it is 1.12g that every liter of stationary phase per hour can be produced alpha-tocopherol, and every production and 1g alpha-tocopherol consume 0.62 liter of moving phase.
Claims (8)
1. the method for a separating single tocopherol from mixed tocopherol is characterized in that: with content is that 50%～100% mixed tocopherol is a raw material, adopt simulated moving bed chromatography isolate highly purified d-α-, d-β-, d-γ-and d-Delta-Tocopherol.
2. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that may further comprise the steps:
(1) mixed tocopherol is dissolved in moving phase, concentration is 1mg/mL～300mg/mL;
(2) from simulated moving bed chromatography system, isolate the tocopherol monomer successively;
(3) steam and to desolventize, obtain purity and yield all be higher than 98% d-α-, d-β-, d-γ-and d-Delta-Tocopherol.
3. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: the total pillar number of described simulated moving bed chromatography is 4～32, every district pillar number is 1～8.
4. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: the optimum total pillar number of described simulated moving bed chromatography is 8～16, and the optimum pillar number in every district is 2～4.
5. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: described moving phase is normal hexane, sherwood oil, methyl alcohol, ethanol, Virahol, acetone, ethyl acetate or its mixed solvent system.
6. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: described stationary phase is gac, silica gel, activated alumina.
7. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: the service temperature of described simulated moving bed chromatography system is 10～60 ℃.
8. according to claim 1 a kind of from mixed tocopherol the method for separating single tocopherol, it is characterized in that: the optimum service temperature of the service temperature of described simulated moving bed chromatography system is 20～50 ℃.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101721838B (en) * | 2009-12-14 | 2011-08-24 | 浙江大学 | Method for separating vitamin E polyethylene glycol succinate monoester from vitamin E polyethylene glycol succinate diester |
| CN105777700A (en) * | 2014-12-23 | 2016-07-20 | 中粮集团有限公司 | Separation method of tocopherol homologous compounds |
| CN108101877A (en) * | 2016-11-24 | 2018-06-01 | 中粮集团有限公司 | A kind of method of continuous chromatography separation tocopherol monomer |
| CN108675980A (en) * | 2018-07-20 | 2018-10-19 | 江南大学 | It a kind of method of the separating and purifying high-purity tocopherol monomer from mixed tocopherol and is prepared using its product and gives birth to red method |
| CN109704938A (en) * | 2018-12-19 | 2019-05-03 | 江南大学 | A kind of method that tocopherol monomer prepares paraquinones |
-
2008
- 2008-01-24 CN CNA2008100594841A patent/CN101220018A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101721838B (en) * | 2009-12-14 | 2011-08-24 | 浙江大学 | Method for separating vitamin E polyethylene glycol succinate monoester from vitamin E polyethylene glycol succinate diester |
| CN105777700A (en) * | 2014-12-23 | 2016-07-20 | 中粮集团有限公司 | Separation method of tocopherol homologous compounds |
| CN105777700B (en) * | 2014-12-23 | 2018-07-10 | 中粮集团有限公司 | A kind of method for detaching tocopherol homologous compound |
| CN108101877A (en) * | 2016-11-24 | 2018-06-01 | 中粮集团有限公司 | A kind of method of continuous chromatography separation tocopherol monomer |
| CN108675980A (en) * | 2018-07-20 | 2018-10-19 | 江南大学 | It a kind of method of the separating and purifying high-purity tocopherol monomer from mixed tocopherol and is prepared using its product and gives birth to red method |
| CN109704938A (en) * | 2018-12-19 | 2019-05-03 | 江南大学 | A kind of method that tocopherol monomer prepares paraquinones |
| CN109704938B (en) * | 2018-12-19 | 2022-02-22 | 江南大学 | Method for preparing p-quinone from tocopherol monomer |
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Open date: 20080716 |