CN114751833B - Dehydroabietylamine chiral ionic liquid and preparation method and application thereof - Google Patents
Dehydroabietylamine chiral ionic liquid and preparation method and application thereof Download PDFInfo
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 41
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000005557 chiral recognition Methods 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims description 16
- DIWVBIXQCNRCFE-MRVPVSSYSA-N (2r)-2-methoxy-2-phenylacetic acid Chemical compound CO[C@@H](C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-MRVPVSSYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000000007 visual effect Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 5
- 101710134784 Agnoprotein Proteins 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NNZGNZHUGJAKKT-UHFFFAOYSA-M 3-bromopropyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCBr NNZGNZHUGJAKKT-UHFFFAOYSA-M 0.000 description 1
- ZQKJDSWJSPZYNR-UHFFFAOYSA-M 4-bromobutyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCBr ZQKJDSWJSPZYNR-UHFFFAOYSA-M 0.000 description 1
- KNKBZYUINRTEOG-UHFFFAOYSA-M 6-bromohexyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCCBr KNKBZYUINRTEOG-UHFFFAOYSA-M 0.000 description 1
- 241000284708 Sarcophaga alpha Species 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000003579 shift reagent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- FCGQIZKUTMUWDC-UHFFFAOYSA-M trimethyl(propyl)azanium;bromide Chemical compound [Br-].CCC[N+](C)(C)C FCGQIZKUTMUWDC-UHFFFAOYSA-M 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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Abstract
The invention belongs to the field of ionic liquid preparation, and in particular relates to dehydroabietylamine chiral ionic liquid, and a preparation method and application thereof, wherein the structure of the dehydroabietylamine chiral ionic liquid is shown as a general formula (I):in the general formula (I), n=3 to 6;is NO 3 ‑ 、BF 4 ‑ 、NTf 2 ‑ Or PF (physical pattern) 6 ‑ One of them. The preparation method of dehydroabietylamine chiral ionic liquid provided by the invention has the advantages of simple salification, no need of complex organic synthesis reaction, simple operation, low cost and easiness in obtaining, and high quaternary ammonium salt content in the product. The dehydroabietylamine chiral ionic liquid has chiral recognition capability on R, S-alpha-methoxy phenylacetic acid.
Description
Technical Field
The invention belongs to the field of ionic liquid preparation, and particularly relates to dehydroabietylamine chiral ionic liquid as well as a preparation method and application thereof.
Background
Ionic liquids are salts composed of organic cations and organic anions or inorganic anions that are in a liquid state at or near room temperature. The ionic liquid has excellent physical and chemical properties, such as low vapor pressure, low volatility, good conductivity, strong polarity, wide electrochemical window and high thermal stability, has better solubility and catalytic performance on a large number of inorganic and organic substances, has a modifiable/modulatable anion-cation structure and can be recycled, so the ionic liquid is considered to be a novel green solvent for replacing common volatile organic solvents, and is widely applied in the chemical industry field.
With the continuous development of ionic liquid design and synthesis technology, some students begin to research the design and introduction of chiral centers in ionic liquids in recent years so as to expand the research field and application range of the ionic liquids. The chiral ionic liquid combines the advantages and characteristics of the ionic liquid and chiral substances, and can be applied to the fields of chiral recognition, asymmetric synthesis, enantiomer resolution, stereoselective polymerization, gas chromatography, NMR shift reagent, liquid crystal and the like. Therefore, the development of chiral ionic liquid has important practical significance in the chiral synthesis field.
At present, a few reports on the aspects of synthesis and application research of chiral ionic liquid exist, but the following problems still exist for the preparation method of dehydroabietylamine chiral ionic liquid: (1) the reaction steps are more, and the process is more complex; (2) the content of quaternary ammonium salt in the product is not high; and (3) the raw materials are not easy to obtain and the price is high.
Disclosure of Invention
The invention aims to solve the technical problems and provides dehydroabietylamine chiral ionic liquid and a preparation method thereof.
The technical scheme of the invention is as follows:
the dehydroabietylamine chiral ionic liquid has a structure shown in a general formula (I):
in the general formula (I), n=3 to 6;is NO 3 - 、BF 4 - 、NTf 2 - Or PF (physical pattern) 6 - One of them.
The method for preparing the dehydroabietylamine chiral ionic liquid comprises the following steps: with side chains of halogenated hydrocarbonsThe quaternary ammonium salt is bonded to the amino of dehydroabietylamine to synthesize chiral ionic liquid A containing secondary amine groups, and the chiral ionic liquid A is respectively combined with AgNO 3 、AgBF 4 、LiNTf 2 Or KPF 6 Performing ion exchange to obtain dehydroabietylamine chiral ionic liquid shown in a general formula (I);
wherein the structural formula of the quaternary ammonium salt with the halogenated hydrocarbon side chain is shown in a general formula (II):
in the general formula (ii), n=3 to 6;
the structural formula of the chiral ionic liquid A is shown as a general formula (III):
in the general formula (iii), n=3 to 6.
The synthetic route is as follows:
further, the method comprises the following steps:
(1) Dissolving dehydroabietylamine and a compound shown in a general formula (II) in acetonitrile, heating to 60-80 ℃ and stirring, dropwise adding ethyl acetate after the reaction is finished, cooling to room temperature for crystallization, and filtering to obtain white crystals; anhydrous Na 2 CO 3 Dispersing in acetonitrile to obtain Na 2 CO 3 Acetonitrile solution, adding the white crystal into the Na in batches under the stirring condition of 50-70 DEG C 2 CO 3 In acetonitrile solution, after reacting for 20-30 h, cooling to room temperature, filtering, taking filtrate, decompressing and drying to obtain white solid, namely the chiral ionic liquid A;
(2) Respectively mixing the chiral ionic liquid A with AgNO 3 、AgBF 4 、LiNTf 2 Or KPF 6 And (3) performing ion exchange to obtain dehydroabietylamine chiral ionic liquid shown in the general formula (I).
Preferably, in the step (2), the chiral ionic liquidBody A and AgNO 3 、AgBF 4 、LiNTf 2 Or KPF 6 The molar ratio of (2) is 1:1.
The application of the dehydroabietylamine chiral ionic liquid in visual chiral recognition of R, S-alpha-methoxyphenylacetic acid comprises the following steps: adding R-alpha-methoxyphenylacetic acid or S-alpha-methoxyphenylacetic acid into dehydroabietylamine chiral ionic liquid shown as a general formula (I) to obtain a mixed solution, heating to 90 ℃, preserving heat for 1h, and then cooling to normal temperature, wherein the mixed solution can be observed after 24 h: the mixed solution of S-alpha-methoxyphenylacetic acid was added to form a gel, and the mixed solution of R-alpha-methoxyphenylacetic acid was added to form a gel.
Further, in the mixed solution, the molar ratio of the R-alpha-methoxyphenylacetic acid or the S-alpha-methoxyphenylacetic acid to the dehydroabietylamine chiral ionic liquid is 1:1.
Further, the concentration of the R-alpha-methoxyphenylacetic acid or the S-alpha-methoxyphenylacetic acid is 0.2mg/mL to 0.7mg/mL.
The beneficial effects of the invention are as follows:
compared with the prior art, the preparation method of the dehydroabietylamine chiral ionic liquid provided by the invention has the advantages of simple salification, no need of complex organic synthesis reaction, simple operation, low cost and easiness in obtaining, and high quaternary ammonium salt content in the product. The dehydroabietylamine chiral ionic liquid has chiral recognition capability on R, S-alpha-methoxy phenylacetic acid.
Drawings
FIG. 1 is a nuclear magnetic resonance C-spectrum of 1.4N-propyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 2 is a nuclear magnetic resonance H-spectrum of 1.4N-propyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 3 is a nuclear magnetic resonance C-spectrum of 1.5N-butyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 4 is a nuclear magnetic resonance H-spectrum of 1.5N-butyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 5 is a nuclear magnetic resonance C-spectrum of 1.6N-hexyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 6 is a nuclear magnetic resonance H-spectrum of 1.6N-hexyltrimethylammonium bromide dehydroabietylamine of the present invention;
FIG. 7 shows a mixed solution containing R-. Alpha. -methoxyphenylacetic acid ((a) and a mixed solution containing S-. Alpha. -methoxyphenylacetic acid (b) of example 6.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
EXAMPLE 1.4 Synthesis of N-propyltrimethylammonium bromide dehydroabietylamine
Dehydroabietylamine (10.00 g,0.035 mol) and 3-bromopropyl trimethylammonium bromide (7.56 g,0.029 mol) were dissolved in 100ml acetonitrile, heated to 70℃and reacted with stirring for 48 hours; after the reaction is finished, 100ml of ethyl acetate is dripped, cooled to room temperature for crystallization, and 10.16g of white crystals are obtained by filtration; 2.07g of anhydrous NaCO 3 Dispersing in 50ml acetonitrile to obtain Na 2 CO 3 Acetonitrile solution, the white crystal is added into the Na in portions under the stirring condition of 60 DEG C 2 CO 3 In acetonitrile solution, the mixture is cooled to room temperature after 24 hours of reaction, and the filtrate is filtered and dried under reduced pressure to obtain white solid (8.59 g, yield63.51%), the structural formula of which is shown in formula a.
The results of nuclear magnetic resonance are shown in fig. 1-2 and analyzed as follows:
1 HNMR(500MHz,Methanol-d 4 )δ7.13(d,J＝8.2Hz,1H,H-11),6.93(dd,J＝8.1,2.1Hz,1H,H-12),6.84(d,J ＝2.0Hz,1H,H-14),3.46–3.39(m,2H,H-23),3.13(s,9H,H-24),2.89–2.83(m,2H,H-7),2.77(p,J＝6.9Hz,1H,H-15),2.68(td,J＝6.8,3.3Hz,2H,H-21),2.57(d,J＝11.9Hz,1H,H-18α),2.37–2.27(m,2H,H-18β,H-1α), 2.01–1.92(m,2H,H-22),1.87–1.61(m,4H,H-1β,5,6),1.59–1.30(m,4H,H-2,3),1.22–1.15(m,9H,H-16,1 7,20),0.96(s,3H,H-19). 13 CNMR(126MHz,Methanol-d 4 )δ147.32(C-9),145.31(C-13),134.46(C-8),12 6.26(C-14),123.81(C-11),123.35(C-12),65.16(C-23),61.18(C-24),52.29(C-21),47.14(C-18),45.48(C-5),38.43(C-1),37.16(C-10),36.76(C-4),35.91(C-3),33.45(C-15),29.78(C-7),24.37(C-20),23.16(C-1 6),23.14(C-17),22.86(C-22),18.57(C-6),18.51(C-2),18.35(C-19).
EXAMPLE 2 Synthesis of 1.5N-butyltrimethylammonium bromide dehydroabietylamine
Dehydroabietylamine (10.00 g,0.035 mol) and 4-bromobutyl trimethyl ammonium bromide (7.97 g,0.029 mol) were dissolved in 100ml acetonitrile, heated to 70℃and reacted with stirring for 48 hours. After the completion of the reaction, 100ml of ethyl acetate was added dropwise thereto and cooled to room temperature for crystallization, and 8.97g of white crystals were obtained by filtration. 1.78g of anhydrous NaCO 3 Dispersing in 50ml acetonitrile to obtain Na 2 CO 3 Acetonitrile solution, the white crystal is added into the Na in portions under the stirring condition of 60 DEG C 2 CO 3 In acetonitrile solution, the mixture is cooled to room temperature after 24 hours of reaction, and the filtrate is filtered and dried under reduced pressure to obtain white solid (7.56 g, yield53.83%), the structural formula of which is shown in formula b.
The results of nuclear magnetic resonance are shown in fig. 3-4 and analyzed as follows:
1 HNMR(500MHz,Methanol-d 4 )δ7.15(d,J＝8.3Hz,1H,H-11),6.95(dd,J＝8.2,2.0Hz,1H,H-12),6.87(d,J ＝2.0Hz,1H,H-14),3.52–3.45(m,2H,H-24),3.22–3.09(m,12H,H-21,25,18α),3.00–2.90(m,3H,H-7,18β) ,2.78(hept,J＝6.9Hz,1H,H-15),2.37(dtd,J＝13.1,3.4,1.3Hz,1H,H-1α),1.97–1.72(m,7H,H-5,6,22,23),1.69(dtd,J＝12.9,3.5,1.3Hz,1H,H-1β),1.51–1.38(m,4H,H-2,3),1.23(s,3H,H-20),1.19(d,J＝6.9Hz,6H,H- 16,17),1.14(s,3H,H-19). 13 CNMR(126MHz,Methanol-d 4 )δ146.54(C-9),145.69(C-13),134.07(C-8),1 26.30(C-14),123.66(C-11),123.55(C-12),65.42(C-24),59.65(C-25),52.41(C-21),48.40(C-18),46.54(C-5),37.77(C-1),37.26(C-10),36.06(C-4),35.49(C-3),33.44(C-15),29.25(C-7),24.14(C-20),23.12(C- 16),23.10(C-17),22.09(C-22),20.06(C-6),18.76(C-2),17.93(C-19),17.01(C-23).
EXAMPLE 3 Synthesis of 1.6N-hexyltrimethylammonium bromide dehydroabietylamine
Dehydroabietylamine (10.00 g,0.035 mol) and 6-bromohexyl trimethyl ammonium bromide (8.78 g,0.029 mol) were dissolved in 100ml acetonitrile, heated to 70℃and reacted with stirring for 48 hours. After completion of the reaction, 100ml of ethyl acetate was added dropwise thereto and cooled to room temperature for crystallization, and 8.41g of white crystals were obtained by filtration. 1.59g of anhydrous Na 2 CO 3 Dispersing in 50ml acetonitrile to obtain Na 2 CO 3 Acetonitrile solution, the white crystal is added into the Na in portions under the stirring condition of 60 DEG C 2 CO 3 In acetonitrile solution, the mixture is cooled to room temperature after 24 hours of reaction, and the filtrate is filtered and dried under reduced pressure to obtain white solid (7.16 g, yield48.56%), the structural formula of which is shown in formula c.
The results of nuclear magnetic resonance are shown in fig. 5-6 and analyzed as follows:
1 HNMR(500MHz,Methanol-d 4 )δ7.13(d,J＝8.2Hz,1H,H-11),6.93(dd,J＝8.2,2.0Hz,1H,H-12),6.84(d, J＝2.0Hz,1H,H-14),3.39–3.32(m,2H,H-26),3.14(s,9H,H-27),2.92–2.73(m,3H,H-7,15),2.65–2.53(m,3H,H-21,18α),2.41(d,J＝12.0Hz,1H,18β),2.30(dt,J＝12.8,3.4Hz,1H,H-1α),1.89–1.29(m,16H,H- 1β,2,3,5,6,22,23,24,25),1.25–1.14(m,9H,h-16,17,20),0.97(s,3H,H-19). 13 CNMR(126MHz,Methan ol-d 4 )δ147.21(C-9),145.33(C-13),134.38(C-8),126.28(C-14),123.82(C-11),123.39(C-12),66.39(C -26),61.25(C-27),52.20(C-21),50.40(C-18),45.89(C-5),38.34(C-1),37.22(C-10),36.56(C-4),35.87(C-3),33.44(C-15),29.76(C-7),28.37(C-25),26.48(C-24),25.77(C-23),24.42(C-20),23.17(C-16,17), 22.46(C-22),18.64(C-6),18.48(C-2),18.25(C-19).
EXAMPLE 4 ion exchange
Dehydroabietylamine (5 mmol) of 1.4N-propyltrimethylammonium bromide of example 1 was reacted with equimolar LiNTf 2 Or KPF 6 Dissolved in water (30 mL),dichloromethane (30 mL) was then added to the above solution, stirred at room temperature for 3 hours, and then left to stand, the dichloromethane phase was separated, washed 3 times with water, and the organic phase was concentrated and dried to give an anion of NTf 2 - Or PF (physical pattern) 6 - DAA-CILs of (C).
EXAMPLE 5 ion exchange
1.4N-propyltrimethylammonium bromide dehydroabietylamine (5 mmol) of example 1 was dissolved in 50% methanol solution, and an equimolar amount of AgNO was added under a dark condition 3 Or AgBF 4 Stirring at room temperature for 24 hr, filtering out precipitate under dark condition, concentrating and drying the filtrate to obtain anion NO 3 - Or BF 4 - DAA-CILs of (C).
Example 6 method for visual chiral identification of R, S-alpha-methoxyphenylacetic acid
Adding R-alpha-methoxyphenylacetic acid or S-alpha-methoxyphenylacetic acid to the anion of example 4 is PF 6 - In DAA-CILs of (1), a mixed solution (wherein the molar ratio of R-alpha-methoxyphenylacetic acid or S-alpha-methoxyphenylacetic acid to dehydroabietylamine chiral ionic liquid is 1:1, and the concentration of R-alpha-methoxyphenylacetic acid or S-alpha-methoxyphenylacetic acid is 0.5 mg/mL) is obtained, then the mixed solution is heated to 90 ℃ for heat preservation for 1 hour and then cooled to normal temperature, and after 24 hours, the mixed solution can be observed: the mixed solution of S-alpha-methoxyphenylacetic acid was added to form a gel, and the mixed solution of R-alpha-methoxyphenylacetic acid was added to form a gel. The difference of the two product states shows that the dehydroabietylamine chiral ionic liquid has chiral recognition capability on R, S-alpha-methoxy phenylacetic acid.
The foregoing description is directed to the preferred embodiments of the present invention, but the embodiments are not intended to limit the scope of the invention, and all equivalent changes or modifications made under the technical spirit of the present invention should be construed to fall within the scope of the present invention.
Claims (3)
1. The application of the dehydroabietylamine chiral ionic liquid in visual chiral recognition of R, S-alpha-methoxyphenylacetic acid is characterized in that the structure of the dehydroabietylamine chiral ionic liquid is shown as a general formula (I):
in the general formula (I), n=3 to 6;is NO 3 - 、BF 4 - 、NTf 2 - Or PF (physical pattern) 6 - Is characterized by comprising the following steps: adding R-alpha-methoxyphenylacetic acid or S-alpha-methoxyphenylacetic acid into dehydroabietylamine chiral ionic liquid shown as a general formula (I) to obtain a mixed solution, heating to 90 ℃, preserving heat for 1h, cooling to normal temperature, and observing after 24 h: the mixed solution of S-alpha-methoxyphenylacetic acid was added to form a gel, and the mixed solution of R-alpha-methoxyphenylacetic acid was added to form a gel.
2. The use according to claim 1, wherein the molar ratio of R- α -methoxyphenylacetic acid or S- α -methoxyphenylacetic acid to dehydroabietylamine chiral ionic liquid in the mixed solution is 1:1.
3. The use according to claim 1, wherein the concentration of R- α -methoxyphenylacetic acid or S- α -methoxyphenylacetic acid is from 0.2mg/mL to 0.7mg/mL.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3941814A (en) * | 1973-07-28 | 1976-03-02 | Dynamit Nobel Aktiengesellschaft | Process for obtaining D(-)-and L(+)-α-azidophenylacetic acid |
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