CN110763780A - High performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone - Google Patents

High performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone Download PDF

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CN110763780A
CN110763780A CN201911078740.6A CN201911078740A CN110763780A CN 110763780 A CN110763780 A CN 110763780A CN 201911078740 A CN201911078740 A CN 201911078740A CN 110763780 A CN110763780 A CN 110763780A
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methylthiophenyl
benzyl
methyl
butanone
dimethylamino
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富玉
王贝
高俊海
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Spectrum Buddhist Nun Tests Group PLC
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Spectrum Buddhist Nun Tests Group PLC
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/62—Detectors specially adapted therefor
    • G01N30/64—Electrical detectors
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N2030/042—Standards
    • G01N2030/047—Standards external

Abstract

The invention belongs to the technical field of analytical chemistry, and relates to a high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone. Separating by octadecyl bonding phase chromatographic column, gradient eluting with acetonitrile and water, and detecting by diode array detector. The method is simple and convenient, can quickly determine the content of the 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and the 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone, and has higher accuracy, stability and separation degree.

Description

High performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone
Technical Field
The invention belongs to the technical field of analytical chemistry, and relates to a high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, in particular to a high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, which has high accuracy, stability and separation degree and is used for chromatographic column separation of an octadecyl bonding phase and detection of a diode array detector.
Background
2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 2-benzyl-2-dimethyllamino-4' -mor pholinothyropenone, CAS 119313-12-1, molecular formula C23H30N2O2The compound has a relative molecular weight of 366.5, is a light yellow powder crystal, is dissolved in organic solvents such as toluene, acetone and the like, has a melting point of 110-115 ℃ and a boiling point of 528.8 ℃, is used for initiating the photopolymerization of free radicals, can be compounded with a proper coinitiator and is used in UV curing ink and coating.
2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, CAS 71868-10-5, formula C15H21O2NS has a relative molecular weight of 279.4, is easily soluble in organic solvents, has a melting point of 74-76 ℃ and a boiling point of 410.5 ℃, and has strong ultraviolet light absorption capacity.
At present, the detection standard for simultaneously detecting 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone is not available at home and abroad. Therefore, a method for detecting the content of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone, which is simple to operate, high in sensitivity and accurate in quantification, is urgently needed to be established.
Disclosure of Invention
The invention aims to provide a high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, which has high accuracy, stability and separation degree of octadecyl bonding phase chromatographic column separation and diode array detector detection.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows: injecting the standard solution into a high performance liquid chromatograph, collecting a chromatogram under the condition of setting an instrument, and quantifying by an external standard method; separating with octadecyl bonded phase chromatographic column, eluting with acetonitrile (A) and water (B) at 40 deg.C in gradient with a procedure of 30% A for 0-7 min; 7-11min, 30-95% A; 11-13min, 95% A; 13-13.1min, 95-30% A; 13.1-18min, 30% A. The flow rate of the column is 1.0mL/min, the sample injection volume is 5 muL, and the diode array detector detects the double-wavelength of 350nm and 299 nm.
Optimally, 350nm is the detection wavelength of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone), and 299nm is the detection wavelength of 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone.
Has the advantages that: the method adopts chromatographic column separation of octadecyl bonding phase and diode array detector detection, and can rapidly determine the content of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone. Compared with the prior art (comparison documents: CN 102818874B, 2014.07.16), the method has the characteristic of high efficiency by optimizing the analysis conditions of the instrument, two targets can peak within 15min, and the method has good separation degree, higher accuracy, stability and separation degree, and is simple and convenient.
Drawings
FIG. 12 is a high performance liquid chromatogram of a benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone standard solution;
FIG. 22 is a high performance liquid chromatogram of a standard solution of methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone
Detailed Description
The present invention is further illustrated by the following examples, but is not limited thereto in any way, and any variations or modifications based on the teachings of the present invention are within the scope of the present invention.
Example one
The high performance liquid chromatograph is used with diode array detector.
Accurately weighing a proper amount of standard substances (2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone, CAS: 119313-12-1; 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, CAS: 71868-10-5), dissolving acetonitrile, fixing the volume, and preparing into a standard solution with the concentration of 5.0 mu g/mL. The chromatographic conditions employed were: inertsustain C18A chromatographic column; column temperature of 40 ℃; gradient elution with acetonitrile (A) and water (B) with procedure of 0-7min, 30% A; 7-11min, 30-95% A; 11-13min, 95% A; 13-13.1min, 95-30% A; 13.1-18min, 30% A;flow rate of 1.0 mL/min; 5 microliter sample injection volume; and detecting by a diode array detector, wherein the detection wavelength is 350nm (2-benzyl-2-dimethylamino-1- (4-morpholinyl phenyl) butanone) and 299nm (2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone). And injecting the standard solution into a high performance liquid chromatograph, and recording the chromatogram. 8.156min and 12.523min are respectively the peaks of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone, the retention time is appropriate, the separation degree is high, and the peak shape symmetry is good.

Claims (3)

1. A high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-acetone is characterized in that gradient elution is carried out by chromatographic column separation of octadecyl bonding phase, column temperature is 40 ℃, acetonitrile and water are used as mobile phase, column flow is 1.0mL/min, sample injection volume is 5 mu L, detection is carried out by diode array detector, detection is carried out by 350nm and 299nm dual-wavelength, spectrogram is collected, and quantification is carried out by external standard method.
2. The high performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-propanone according to claim 1, wherein the gradient elution is performed for 0-7min at 30% A; 7-11min, 30-95% A; 11-13min, 95% A; 13-13.1min, 95-30% A; 13.1-18min, 30% A.
3. The HPLC detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-propanone according to claim 1, wherein 350nm is the detection wavelength of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone), and 299nm is the detection wavelength of 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-propanone.
CN201911078740.6A 2019-11-02 2019-11-02 High performance liquid chromatography detection method of 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone and 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone Pending CN110763780A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2447715A1 (en) * 2010-11-01 2012-05-02 Agilent Technologies, Inc. Method for forming polymeric porous layer open tubular columns by photopolymerisation with visible light
CN102818874A (en) * 2012-08-31 2012-12-12 国家烟草质量监督检验中心 Detection method of determining 16 types of photoinitiators in paper printing and packaging material
CN107894487A (en) * 2017-12-29 2018-04-10 国家烟草质量监督检验中心 The detection method of light trigger in a kind of printed apcksging material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2447715A1 (en) * 2010-11-01 2012-05-02 Agilent Technologies, Inc. Method for forming polymeric porous layer open tubular columns by photopolymerisation with visible light
CN102818874A (en) * 2012-08-31 2012-12-12 国家烟草质量监督检验中心 Detection method of determining 16 types of photoinitiators in paper printing and packaging material
CN107894487A (en) * 2017-12-29 2018-04-10 国家烟草质量监督检验中心 The detection method of light trigger in a kind of printed apcksging material

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
T. JUNG等: "Multi-analyte methods for the detection of photoinitiators and amine synergists in food contact materials and foodstuffs – Part I: HPLC-DAD screening of materials", 《FOOD ADDITIVES & CONTAMINANTS: PART A》 *

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Application publication date: 20200207