CN109908765A - A kind of microporous polymer membranes of tool certainly and preparation method thereof that L-TARTARIC ACID is modified - Google Patents
A kind of microporous polymer membranes of tool certainly and preparation method thereof that L-TARTARIC ACID is modified Download PDFInfo
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Abstract
The present invention relates to a kind of modifications of L-TARTARIC ACID from tool microporous polymer membranes and preparation method thereof, and n,N-Dimethylformamide is moved into dry three-necked flask first, 5,5 ', 6 are taken again, 6 '-tetrahydroxys -3,3,3 ', 3 '-tetramethyl -1, the double indanes and 3,4 of 1 '-spiral, 5,6- tetrafluoro phthalic nitrile moves into three-necked flask, and stirring adds Anhydrous potassium carbonate and L-TARTARIC ACID to after dissolving；Non-homogeneous mixture is vacuumized, and is passed through nitrogen and is protected, heating stirring；After being cooled to room temperature, deionized water is added into flask, then filters, obtain yellow mercury oxide, carries out multiple rinse with water and methanol respectively；Finally obtained product is dried in vacuo；After product is dissolved with tetrahydrofuran, it is poured into the quartzy culture dish that diameter is 6cm and is film-made at room temperature；L-TARTARIC ACID is introduced in Inventive polymers film, makes film that there are Chiral properties, to make it have chiral recognition.
Description
Technical field
The present invention relates to polymeric membrane fields, and in particular to a kind of modification of L-TARTARIC ACID is from tool microporous polymer membranes and its system
Preparation Method.
Background technique
Chirality is one of essential attribute of nature, is widely present in chipal compounds, such as organism in nature
Base substance such as amino acid, carbohydrate etc., therefore region of chemistry attaches great importance to the research and development of chiral material.So far, chiral resolution skill
Art mainly has film Split Method, chemical resolution method, Enzymatic Resolution, Chromatographic resolution method, induction crystallisation, Extraction resolution method etc..Although
High performance liquid chromatography is very advantageous in terms of resolving chiral compound, and mobile phase range is wide, effective plate number is high etc. is adjusted,
Become one of main means of extensive resolving chiral compound at present；However, current most of method for splitting is all
The place for having it to limit to: the such as spent cost of crystallization fractionation is relatively high, to consume expensive resolution reagent and can only be directed to
Specific split system；The irreversible decline of catalytic efficiency is then faced with using Enzymatic Resolution chipal compounds；Chromatography rule tool
Have the shortcomings that discontinuous and stationary phase material is expensive.Compared to the above, film Split Method has low energy consumption, high carrying capacity and Ke Lian
The advantages such as continuous operation, make it can be used for extensive resolving chiral compound.
Currently, the poromerics of high-specific surface area separating-purifying, heterogeneous catalysis and in terms of application
Prospect is very wide, thus has received widespread attention.Reported chiral film substantially can be divided into other than liquid chiral film
Two classes, one kind are based on the chiral film selectively spread, and another kind of is then the chiral film based on selective absorption.The former infiltration
Rate is usually inversely proportional with chiral recognition, to block its further industrial application；And the latter needs precision system standby
Porous material and valuableness chiral recognition agent, preparation process is complicated, and is difficult to avoid that in process of osmosis non-selective
The generation of infiltration.Therefore, preparing a kind of with suitable size and highly selective chiral film will break through the pass of chiral film research
Key.
Summary of the invention
The purpose of the present invention is to provide a kind of modifications of L-TARTARIC ACID from tool microporous polymer membranes and preparation method thereof, by 5,
5 ', 6,6 '-tetrahydroxys -3,3,3 ', the double indanes of 3 '-tetramethyls -1,1 '-spiral are used as with 3,4,5,6- tetrafluoro phthalic nitrile to be polymerize
Monomer, L-TARTARIC ACID is as chiral building block, to prepare the tool microporous polymer membranes certainly with chiral selectivity.For ammonia
Base acid enantiomer because from tool microporous polymer membranes it is different from the interaction of L-type amino acid to D type, amino acid enantiomer it
Between different permeability can cause the separation of chiral isomer.Tyrosine enantiomer, tryptophan mapping have further been investigated in experiment
Body, phenylalanine enantiomer are modified by L-TARTARIC ACID from permeability behavior when having microporous polymer membranes, and not with L-TARTARIC ACID
Modification is compared from tool microporous polymer membranes.Due to having microporous polymer membranes certainly to D/L- tryptophan (phenylalanine, phenylpropyl alcohol
Propylhomoserin) adsorption capacity it is different, therefore D-Tyrosine (tryptophan, phenylalanine) and l-tyrosine (tryptophan, phenylalanine)
Achieve the purpose that separation in the migration rate difference from tool microporous polymer membranes both ends.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of modification of L-TARTARIC ACID from tool microporous polymer membranes, constituent includes n,N-Dimethylformamide, 5,5 ', 6,
6 '-tetrahydroxys -3,3,3 ', the double indane of 3 '-tetramethyls -1,1 '-spiral, 3,4,5,6- tetrafluoro phthalic nitrile, Anhydrous potassium carbonate and
L-TARTARIC ACID.
The preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification, comprising the following steps:
(1) n,N-Dimethylformamide is measured, is moved into dry three-necked flask, 5,5 ', 6,6 '-tetrahydroxys -3,3 of addition, 3 ',
3 '-tetramethyl -1, the double indanes and 3 of 1 '-spiral, 4,5,6- tetrafluoro phthalic nitriles after stirring and dissolving, add Anhydrous potassium carbonate
It is mixed into non-homogeneous mixture as dressing agent with L-TARTARIC ACID, and a dry magneton is added；
(2) three-necked flask is fixed on iron stand, loads onto condenser pipe, thermometer, nitrogen bag and glass valve in bottleneck group；
(3) non-homogeneous mixture in three-necked flask is vacuumized, and is passed through nitrogen and is protected, stirred in a heated condition,
Obtain glutinous shape object；
(4) glutinous shape object is cooled to room temperature, deionized water is added, suction filtration obtains yellow mercury oxide；
(5) precipitating is subjected to a small amount of multiple rinse with water and methanol respectively, then obtained product is dried in vacuo, is obtained
To crude product；
(6) it weighs a certain amount of crude product and tetrahydrofuran dissolution is added, pour into culture dish at room temperature and be allowed to form a film.
Step (1) the n,N-Dimethylformamide additional amount be 15mL, described 5,5 ', 6,6 '-tetrahydroxys -3,3,3 ',
The additional amount of 3 '-tetramethyl -1, the double indanes of 1 '-spiral is 0.8895g, the additional amount of described 3,4,5,6- tetrafluoro phthalic nitriles
For 0.5299g, the Anhydrous potassium carbonate additional amount is 3g, and the additional amount of the L-TARTARIC ACID is 0.0039g.
It is heated to be described in step (3) and is heated under the conditions of 70 DEG C；The mixing time is for 24 hours.
The additional amount of step (4) described deionized water is 50mL.
Step (5) the vacuum drying condition are as follows: be dried in vacuo 12h at 120 DEG C.
Final concentration of 0.06g/mL of step (6) the described crude product in tetrahydrofuran.
The present invention has the advantages that
(1) the tool microporous polymer membranes certainly of L-TARTARIC ACID modification improve amino from tool microporous polymer membranes compared to unmodified
The penetrating concentration of acid, compared with phenylalanine and Tryptophan enantiomer, separating degree of the tyrosine enantiomer in organic polymer film
Highest, chiral resolution effect are best.
(2) compared with the chiral film based on selective absorption, preparation process of the present invention is simple, and can avoid non-selective
The generation of infiltration.
Detailed description of the invention
Fig. 1 is from tool microporous polymer membranes.
Fig. 2 is L-TARTARIC ACID modification tool microporous polymer membranes certainly.
Fig. 3 is L-TARTARIC ACID modification from having microporous polymer membranes (A) with unmodified from the infrared of tool microporous polymer membranes (B)
Spectrogram.
Fig. 4 is that L-TARTARIC ACID modification is compared from tool microporous polymer membranes and the infrared spectrogram from tool microporous polymer membranes
Figure.
Fig. 5 is D-Tyrosine and l-tyrosine solution standard working curve figure.
Fig. 6 is D-trp and L-Trp solution standard working curve figure.
Fig. 7 is D-phenylalanine and L-phenylalanine solution standard working curve figure.
Specific embodiment
Embodiment 1
Measure 15mL DMF(N, dinethylformamide) the dry three-necked flask of immigration, precise 0.8895g TTSBI(5,
5 ', 6,6 '-tetrahydroxys -3,3,3 ', the double indanes of 3 '-tetramethyls -1,1 '-spiral), 0.5229g TFTPN (3,4,5,6- tetrafluoro
Phthalic nitrile) it moves into three-necked flask, stirring adds 3g Anhydrous potassium carbonate and 0.0039g L- winestone is added to after dissolving
Acid is used as dressing agent, and a dry magneton is added.Three-necked flask is fixed on iron stand, by condenser pipe, thermometer, nitrogen
Airbag, glass valve are assembled in three-necked flask.Non-homogeneous mixture is vacuumized, and is passed through nitrogen and is protected, in 70 DEG C of items
Heating stirring is for 24 hours under part.After being cooled to room temperature, glutinous shape object is poured into 50mL deionized water, suction filtration obtains yellow mercury oxide, uses respectively
Water and methanol carry out a small amount of multiple rinse.Then obtained product is dried in vacuo 12h at 120 DEG C.
It weighs 0.09g crude product 1.5mL tetrahydrofuran to dissolve, being poured into the culture dish that diameter is 6cm at room temperature makes
Film forming, as shown in Figure 1.
Comparative example 1
Measure 15mL DMF(N, dinethylformamide) the dry three-necked flask of immigration, precise 0.8895g TTSBI(5,
5 ', 6,6 '-tetrahydroxys -3,3,3 ', the double indanes of 3 '-tetramethyls -1,1 '-spiral), 0.5229g TFTPN (3,4,5,6- tetrafluoro
Phthalic nitrile) it moves into three-necked flask, stirring adds 3g Anhydrous potassium carbonate and a dry magneton to after dissolving.By three
Mouth flask is fixed on iron stand, and condenser pipe, thermometer, nitrogen bag, glass valve are assembled in three-necked flask.It will be heterogeneous mixed
It closes object to vacuumize, and is passed through nitrogen and is protected, heating stirring is for 24 hours under the conditions of 70 DEG C.After being cooled to room temperature, glutinous shape object is fallen
Enter 50mL deionized water, suction filtration obtains yellow mercury oxide, carries out a small amount of multiple rinse with water and methanol respectively.Then it will obtain
Product is dried in vacuo 12 h at 120 DEG C.
It weighs 0.09g crude product 1.5mL tetrahydrofuran to dissolve, is poured into the culture dish that diameter is 6cm at room temperature and trains
Feeding ware is allowed to form a film, as shown in Figure 2.
The product that embodiment 1 and comparative example 1 obtain is subjected to infrared detection respectively, as a result sees Fig. 3 A, Fig. 3 B and Fig. 4；Its
Middle Fig. 3 A is L-TARTARIC ACID modification tool microporous polymer membranes certainly；Fig. 3 B is from tool microporous polymer membranes；As seen from the figure, L-TARTARIC ACID
The infrared spectrum of the tool microporous polymer membranes certainly of modification and certainly tool microporous polymer membranes is about the same in addition to peak intensity is weak, because of L- wine
The chemical formula of stone acid is C4H6O6, therefore can only change the strong of peak in the infrared spectroscopy of the microporous polymer membranes of tool certainly of L-TARTARIC ACID decorations
It is weak.In 3430cm-1There is OH stretching absorbance peak and in 1607cm-1Benzene occur replaces skeletal vibration absorption peak to be remarkably reinforced,
1450cm-1There is benzene and replaces skeletal vibration absorption peak, in 1265cm-1Occur alcohols, curved (in the face) absorption peak of phenols OH and
1012cm-1Appearance aryl oxide=C-O-C stretches (symmetrical) absorption peak and obviously weakens.It can be seen that, L-TARTARIC ACID is modified in summary
From tool microporous polymer membranes.
Fractionation behavior of 2 L-TARTARIC ACID of the embodiment modification from tool microporous polymer membranes to each amino acid enantiomer
One, the normal concentration working curve measurement of each amino acid enantiomer
(1) the normal concentration working curve of tyrosine
Concentration is 7.5 × 10-5 mol/L、5×10-5 mol/L、2.5×10-5 mol/L、1×10-5 mol/L、7.5×10-6
mol/L、5×10-6 mol/L、2.5×10-6 mol/L、1×10-6Corresponding to the D-Tyrosine and l-tyrosine solution of mol/L
Absorbance standard working curve it is as shown in table 1.
1 D-Tyrosine of table and l-tyrosine solution standard working curve equation
(2) the normal concentration working curve of tryptophan
Concentration is 7.5 × 10-5 mol/L、5×10-5 mol/L、2.5×10-5 mol/L、1×10-5 mol/L、7.5×10-6
mol/L、5×10-6 mol/L、2.5×10-6 mol/L、1×10-6Corresponding to the D-trp and L-Trp solution of mol/L
Absorbance standard working curve it is as shown in table 2.
2 D-trp of table and L-Trp solution standard working curve equation
(3) the normal concentration working curve of phenylalanine
Concentration is 7.5 × 10-5 mol/L、5×10-5 mol/L、2.5×10-5 mol/L、1×10-5 mol/L、7.5×10-6
mol/L、5×10-6 mol/L、2.5×10-6 mol/L、1×10-6The D-phenylalanine of mol/L and L-phenylalanine solution institute
The standard working curve of corresponding absorbance is as shown in table 3.
3 D-phenylalanine of table and L-phenylalanine solution standard working curve equation
Two, fractionation behavior of the L-TARTARIC ACID modification from tool microporous polymer membranes to tyrosine enantiomer
After the D-Tyrosine (l-tyrosine) of 0.0102g to be dissolved in the sodium dihydrogen phosphate that 50mL concentration is 0.05mol/L,
Obtain the tyrosine solution that 50mL concentration is 1mmol/L.L-TARTARIC ACID modification is attached to H-type electrolysis from tool microporous polymer membranes
Pond when separation, the tyrosine solution prepared is added in one end of H-type electrolytic cell, is added in the other end of H-type electrolytic cell
50mL concentration is the sodium dihydrogen phosphate of 0.05mol/L, is put into clean magneton, is sirred and separated.H-type is surveyed every a hour
Absorbance (wavelength setting: tyrosine 280nm) in electrolytic cell equipped with sodium dihydrogen phosphate one end, and according to tyrosine mapping
The standard curve (table 1) of body is converted to concentration, and the testing time is 8 h.The experimental results showed that the osmotic concentration of D-Tyrosine compared with
Height, the penetrating concentration of l-tyrosine is lower than detection limit, i.e., concentration is less than 10-6Mol/L(is as shown in figure 5, surveyed concentration is less than in figure
10-6Mol/L is with 10-6Mol/L is indicated).It follows that the osmotic effect of D-Tyrosine is better than l-tyrosine.
Three, fractionation behavior of the L-TARTARIC ACID modification from tool microporous polymer membranes tryptophan enantiomer
After 0.0090g D-trp (L-Trp) to be dissolved in the sodium dihydrogen phosphate that 50mL concentration is 0.05mol/L,
Obtain the tryptophan solution that 50mL concentration is 1mmol/L.L-TARTARIC ACID modification is attached to H-type electrolysis from tool microporous polymer membranes
Pond when separation, the tryptophan solution prepared is added in one end of H-type electrolytic cell, is added in the other end of H-type electrolytic cell
50mL concentration is the sodium dihydrogen phosphate of 0.05mol/L, is put into clean magneton, is sirred and separated.H-type is surveyed every a hour
Absorbance (wavelength setting: tryptophan 277nm) in electrolytic cell equipped with sodium dihydrogen phosphate one end, and according to tryptophan mapping
The standard curve (table 2) of body is converted to concentration, and the testing time is 8 h.The experimental results showed that the osmotic concentration of L-Trp compared with
Height, the penetrating concentration of D-trp is lower than detection limit, i.e., concentration is less than 10-6Mol/L(is as shown in fig. 6, surveyed concentration is less than in figure
10-6Mol/L is with 10-6Mol/L is indicated).It follows that the osmotic effect of L-Trp is better than D-trp.
Four, fractionation behavior of the L-TARTARIC ACID modification from tool microporous polymer membranes to phenylalanine enantiomer
0.0082g D-phenylalanine (L-phenylalanine) is dissolved in the sodium dihydrogen phosphate that 50mL concentration is 0.05mol/L
Afterwards, the Phe solution that 50mL concentration is 1mmol/L is obtained.L-TARTARIC ACID modification is attached to H-type from tool microporous polymer membranes
Electrolytic cell when separation, the Phe solution prepared is added in one end of H-type electrolytic cell, in the other end of H-type electrolytic cell
The sodium dihydrogen phosphate that 50mL concentration is 0.05mol/L is added, is put into clean magneton, is sirred and separated.Every a hour
The absorbance (wavelength setting: phenylalanine 257nm) in H-type electrolytic cell equipped with sodium dihydrogen phosphate one end is surveyed, and according to benzene
The standard curve (table 3) of Alanine enantiomers is converted to concentration, testing time 8h.The experimental results showed that L-phenylalanine
Osmotic concentration is higher, and the penetrating concentration of D-phenylalanine is lower (as shown in fig. 7, surveyed concentration is less than 10 in figure-6Mol/L with
10-6Mol/L is indicated).It follows that the osmotic effect of L-phenylalanine is better than D-phenylalanine.
Unmodified separating behavior of the tool microporous polymer membranes to amino acid certainly of comparative example 2
Three kinds of tyrosine, tryptophan, phenylalanine amino acid enantiomers are probed into respectively in the unmodified microporous polymer membranes of tool certainly
Permeability behavior.The experimental results showed that tryptophan, phenylalanine, tyrosine enantiomer are unmodified from tool microporous polymer membranes
In osmotic concentration below detect limit, i.e., concentration is less than 10-6mol/L。
In the present invention, amino acid enantiomer is obviously high from the penetrating concentration in tool microporous polymer membranes in L-TARTARIC ACID modification
In unmodified from tool microporous polymer membranes.Wherein, the osmotic effect of D-Tyrosine is better than l-tyrosine, the infiltration of L-Trp
Saturating effect is better than D-phenylalanine better than the osmotic effect of D-trp, L-phenylalanine.All in all, 1%L- tartaric acid is modified
Tyrosine enantiomer, followed by phenylalanine and tryptophan can be preferably split from tool microporous polymer membranes.
After needing first to be cleaned up with deionized water before each use of the instruments such as required beaker, culture dish
With ethyl alcohol rinse, can be used just now after then being dried by drying box.And it needs to make before measuring solution absorbance to be measured
The working curve of D/L- tryptophan (phenylalanine, tyrosine) enantiomer, converts concentration for absorbance by by working curve
Transmitance figure is made, just can guarantee accuracy in this way.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (7)
1. a kind of tool microporous polymer membranes certainly of L-TARTARIC ACID modification, which is characterized in that constituent includes N, N- dimethyl methyl
Amide, 5,5 ' 6,6 '-tetrahydroxys -3,3,3 ', the double indane of 3 '-tetramethyls -1,1 '-spiral, 3,4,5,6- tetrafluoro phthalic nitrile,
Anhydrous potassium carbonate and L-TARTARIC ACID.
2. a kind of preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification as described in claim 1, feature exist
In, comprising the following steps:
(1) n,N-Dimethylformamide is measured, is moved into dry three-necked flask, 5,5 ', 6,6 '-tetrahydroxys -3,3 of addition, 3 ',
3 '-tetramethyl -1, the double indanes and 3 of 1 '-spiral, 4,5,6- tetrafluoro phthalic nitriles after stirring and dissolving, add Anhydrous potassium carbonate
It is mixed into non-homogeneous mixture as dressing agent with L-TARTARIC ACID, and a dry magneton is added；
(2) three-necked flask is fixed on iron stand, loads onto condenser pipe, thermometer, nitrogen bag and glass valve in bottleneck group；
(3) non-homogeneous mixture in three-necked flask is vacuumized, and is passed through nitrogen and is protected, stirred in a heated condition,
Obtain glutinous shape object；
(4) glutinous shape object is cooled to room temperature, deionized water is added, suction filtration obtains yellow mercury oxide；
(5) precipitating is subjected to a small amount of multiple rinse with water and methanol respectively, then obtained product is dried in vacuo, is obtained
To crude product；
(6) it weighs a certain amount of crude product and tetrahydrofuran dissolution is added, pour into culture dish at room temperature and be allowed to form a film.
3. the preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification according to claim 2, which is characterized in that
Step (1) the n,N-Dimethylformamide additional amount is 15mL, described 5,5 ', 6,6 '-tetrahydroxys -3,3,3 ', 3 '-tetramethyls
The additional amount of the double indanes of 1,1 '-spiral of base-is 0.8895g, and the additional amount of described 3,4,5,6- tetrafluoro phthalic nitriles is
0.5299g, the Anhydrous potassium carbonate additional amount are 3g, and the additional amount of the L-TARTARIC ACID is 0.0039g.
4. the preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification according to claim 2, which is characterized in that
It is heated to be described in step (3) and is heated under the conditions of 70 DEG C；The mixing time is for 24 hours.
5. the preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification according to claim 2, which is characterized in that
The additional amount of step (4) described deionized water is 50mL.
6. the preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification according to claim 2, which is characterized in that
Step (5) the vacuum drying condition are as follows: be dried in vacuo 12h at 120 DEG C.
7. the preparation method from tool microporous polymer membranes of L-TARTARIC ACID modification according to claim 2, which is characterized in that
Final concentration of 0.06g/mL of step (6) the described crude product in tetrahydrofuran.
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| CN1772356A (en) * | 2005-11-02 | 2006-05-17 | 华东理工大学 | Composite fiber membrane with chiral molecular imprint and its prepn and application |
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| CN106018517A (en) * | 2016-05-16 | 2016-10-12 | 常州大学 | Preparation of tartaric acid-graphene quantum dot composite film modified electrode and application in tryptophan enantiomer recognition |
| CN106279672A (en) * | 2015-05-28 | 2017-01-04 | 中国科学院苏州纳米技术与纳米仿生研究所 | From tool micro-porous copolymers, its preparation method and application |
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2019
- 2019-03-14 CN CN201910197388.1A patent/CN109908765B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1772356A (en) * | 2005-11-02 | 2006-05-17 | 华东理工大学 | Composite fiber membrane with chiral molecular imprint and its prepn and application |
| CN103087316B (en) * | 2013-01-29 | 2014-07-30 | 西南科技大学 | Preparation method of soluble heat-resistant polymer based on benzpyrole skeleton |
| CN104841288A (en) * | 2015-04-30 | 2015-08-19 | 天津工业大学 | Composite microgel membrane for CO2/N2 gas separation and preparation method thereof |
| CN106279672A (en) * | 2015-05-28 | 2017-01-04 | 中国科学院苏州纳米技术与纳米仿生研究所 | From tool micro-porous copolymers, its preparation method and application |
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