CN105092741A - Method for detecting 3-amino-2-caprolactam through high performance liquid chromatography - Google Patents
Method for detecting 3-amino-2-caprolactam through high performance liquid chromatography Download PDFInfo
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- GEBIBHFITVKXGW-UHFFFAOYSA-N 3-(1-aminobutyl)aziridin-2-one Chemical compound CCCC(N)C1NC1=O GEBIBHFITVKXGW-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 102
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- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims abstract description 17
- 235000019796 monopotassium phosphate Nutrition 0.000 claims abstract description 17
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
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- 238000002360 preparation method Methods 0.000 claims description 28
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- 238000011084 recovery Methods 0.000 abstract description 15
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract description 8
- 239000004472 Lysine Substances 0.000 abstract description 8
- 238000001514 detection method Methods 0.000 abstract description 8
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- 238000004458 analytical method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 antibody Proteins 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 108010039918 Polylysine Proteins 0.000 description 5
- 235000018102 proteins Nutrition 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007689 inspection Methods 0.000 description 4
- 229920000656 polylysine Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- PLXCIRQDSXGLTH-UHFFFAOYSA-N 3-(1-aminobutyl)aziridin-2-one hydrochloride Chemical compound Cl.NC(C1C(=O)N1)CCC PLXCIRQDSXGLTH-UHFFFAOYSA-N 0.000 description 1
- 208000001889 Acid-Base Imbalance Diseases 0.000 description 1
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
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- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
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- Investigating Or Analysing Biological Materials (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a method for detecting 3-amino-2-caprolactam by high performance liquid chromatography, which adopts the following chromatographic conditions: the chromatographic column is an ODS column; the mobile phase A is 0.01-0.09 mol/L potassium dihydrogen phosphate solution; the mobile phase B is a mixed aqueous solution of methanol and acetonitrile, and the volume ratio of the methanol to the acetonitrile to the water is 1-5: 1; the flow rate is 0.4-1.2 ml/min; the detection wavelength is 100-300 nm; the column temperature is 20-60 ℃; the sample injection amount is 5-20 mul. The method can accurately measure the content of the lysine degradation impurity 3-amino-2-caprolactam, and has good specificity. The method has the advantages of good quantitative limit repeatability, high recovery rate and good solution stability. When the column temperature, the detection wavelength and the flow rate are slightly changed, the difference between the measured recovery rate of the 3-amino-2-caprolactam and the recovery rate under the basic condition is very small, which shows that the invention has good durability.
Description
Technical field
The present invention relates to the detection method of amino acid injection, particularly relate to a kind of method that high performance liquid chromatography detects 3-amino-2-caprolactam.
Background technology
Amino acid (aminoacid) is the common name of the class organic compound containing amino and carboxyl, it is the basic composition unit of biological function macro-molecular protein, being the base substance forming Animal nutrition desired protein, is the organic compound containing basic amine group and acidic carboxypolymer.Amino acid injection (AminoAcidInjection), the sterile water solution formulated by 18 seed amino acids, the patient of organism metabolism needs can not be met, also for improving the nutrition condition of patients after surgery for amino acid such as protein insufficiency of intake, malabsorptions.Drip-feed, each 250 ~ 500ml, children 35 ~ 50ml/kg.Have and promote human body protein Metabolism of Normal, correct negative nitrogen balance, supplement protein, the effect of accelerating wound.Amino acid transfusion, when Power supply abundance, can enter histocyte, participates in the anabolism of protein, obtain positive nitrogen equilibrium, and generate the physiological activators such as enzyme, hormone, antibody, structural proteins, promote organization healing, recover normal physiological function.This product can cause the allergic reaction of rash sample, once occur to discontinue medication.Occasionally there are Nausea and vomiting, uncomfortable in chest, palpitaition, feel cold, generate heat or headache etc.Serious hepatic and kidney function obstacle, hepatic coma, serious azotemia, serious uremic patient and disorder of amino acid catabolism person's forbidding.Serious acidosis, congestion type heart failure person are cautious use of.Points for attention: strictly should control drip velocity; This strain hydrochloride, a large amount of input may cause acid-base imbalance; Widely apply or and when infusing with electrolyte, electrolyte and acid base equilibrium should be noted; With front must detailed inspection liquid, as find body have break, leak gas, variable color, mouldy, precipitation, the abnormal occurrence such as to go bad absolutely not should use; After this product is opened, can not store and re-use.
3-amino-2-caprolactam (3-Amino-2-azepanone), another name: DL-alpha-amido-epsilon-caprolactams, CAS:671-42-1, MDL:MFCD00064475, chemical formula is C
6h
12n
2o, molecular weight is 128.17, fusing point 77 DEG C, boiling point 168 ~ 172 DEG C.Lysine (lysine), another name the first limiting amino acids, chemical formula is C
6h
14n
2o
2, molecular weight is 146.19, is basic amino acid, is one of human body 8 kinds of essential amino acids, has L-type and D-type two kinds of isomerss.3-amino-2-caprolactam is the catabolite of lysine, by accurately detecting the content of 3-amino-2-caprolactam in amino acid injection, strictly can control the product quality of amino acid injection.But retrieval at present finds no the method adopting high performance liquid chromatography to detect 3-amino-2-caprolactam content.High performance liquid chromatography (HighPerformanceLiquidChromatography, HPLC) is also known as " high pressure liquid chromatography ", " high-speed liquid chromatography ", " high separation liquid chromatography ", " column chromatography in modern age " etc.High performance liquid chromatography is a chromatographic important branch, take liquid as mobile phase, adopt high pressure transfusion system, the mobile phase such as mixed solvent, damping fluid of the single solvent or different proportion with opposed polarity is pumped into the chromatographic column that Stationary liquid is housed, in post each composition separated after, enter detecting device to detect, thus realize the analysis to sample.The method has become separate analytical technique important in the ambits such as chemistry, medical science, industry, agronomy, commodity inspection and method inspection.
Application number be 201010513639.1 Chinese patent application disclose Amino Acid Compound Injection and preparation method thereof, detection method, this parenteral solution is made up of 18 seed amino acids, sodium bisulfite, xylitol and water, the invention also discloses the preparation method of Amino Acid Compound Injection (18AA) simultaneously, while guarantee product quality, there is feature that is energy-conservation, synergy; The present invention, by repeatedly verifying precision, detectability, quantitative limit and the range of linearity etc., determines the method for the easy fast and reliable of cleaning checking; And this invention is also according to chromatography of ions principle, detect the residual quantity of antioxidant sodium bisulfite in Amino Acid Compound Injection, and the sulfate ion that sodium bisulfite degraded produces, thus the antioxygen dosage dropped in Accurate Determining pulp furnish, and judge the stability of pulp furnish technique according to measurement result; The Amino Acid Compound Injection detection method that this invention provides is a kind of On-chip derivatization Contents of Amino Acids method, and speed is fast, is applicable to large scale inspection of producing.But this invention can not the content of organism such as 3-amino-2-caprolactam in on-line checkingi amino acid injection.
Application number is the detection method that the Chinese patent application of CN201110023106.X discloses a kind of polylysine, first this invention calculates typical curve with the diffusion circle diameter of standard solution and polylysine log concentration value, then the diffusion circle diameter of working sample solution generation, calculates the concentration of polylysine in unknown sample from typical curve.This invention can reach the object detecting fast epsilon-polylysine content in polylysine content and high-sensitivity detection food in fermentation liquor respectively by adjustment testing conditions.But this invention range of application is narrower.
Summary of the invention
The object of the invention is to the shortcoming overcoming prior art, provide a kind of high performance liquid chromatography to detect the method for 3-amino-2-caprolactam.
Object of the present invention is achieved through the following technical solutions: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, adopts following chromatographic condition:
Chromatographic column: ODS post;
Mobile phase A: potassium dihydrogen phosphate;
Mobile phase B: the aqueous solution of methyl alcohol, acetonitrile;
Flow velocity: 0.4 ~ 1.2ml/min;
Determined wavelength: 100 ~ 300nm;
Column temperature: 20 ~ 60 DEG C;
Sample size: 5 ~ 20 μ l.
Described determined wavelength is 200nm, and column temperature is 35 DEG C, and sample size is 10 μ l.
Described mobile phase A is the potassium dihydrogen phosphate of 0.01 ~ 0.09mol/L, and described Mobile phase B is the mixed aqueous solution of methyl alcohol, acetonitrile, and the volume ratio of methyl alcohol, acetonitrile and water is 1 ~ 5:1 ~ 5:1.
Described a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 5.44 ~ 48.99g, be diluted with water to 4000ml, with phosphorus acid for adjusting pH to 2 ~ 4, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 1 ~ 5:1 ~ 5:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 10 ~ 30mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph, carries out efficient liquid phase chromatographic analysis according to the condition described in any one of Claims 1 to 4.
The present invention has following beneficial effect:
(1) content of energy Accurate Determining 3-amino-2-caprolactam of the present invention, specificity is good;
(2) regression equation of 3-amino-2-caprolactam liquid chromatography peak area of the present invention and its concentration is linear correlation, and its linear fit is better, therefore easy to use;
(3) quantitative limit of the present invention is reproducible, and RSD (n=6) is 1.86%;
(4) the 3-amino-2-caprolactam recovery of the present invention is high, and average recovery rate reaches 99.42%;
(5) stability of solution of the present invention is good, and test solution 3-amino-2-caprolactam concentration after ambient temperatare puts 36h keeps stable, and RSD is 0.54%; 3-amino-2-caprolactam the recovery keeps stable, and RSD is 0.55%;
(6) durability of the present invention is good, and when trickle change occurs for column temperature, determined wavelength, flow velocity, the recovery determining 3-amino-2-caprolactam differs very little with measurement result under pacing items.
Accompanying drawing explanation
Fig. 1 is 3-amino-2-caprolactam simple linear regression analysis figure of the present invention;
Fig. 2 is reference substance solution liquid chromatogram of the present invention.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention will be further described, and protection scope of the present invention is not limited to the following stated.
Embodiment 1: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 5.44g, be diluted with water to the potassium dihydrogen phosphate that 4000ml obtains 0.01mol/L, with phosphorus acid for adjusting pH to 2, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 1:5:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 10mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph and analyzes.The chromatographic condition adopted is: chromatographic column: ODS post; Flow velocity: 0.4 ~ 1.2ml/min; Determined wavelength: 100nm; Column temperature: 20 DEG C; Sample size: 5 μ l.
Embodiment 2: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 16.33g, be diluted with water to the potassium dihydrogen phosphate that 4000ml obtains 0.03mol/L, with phosphorus acid for adjusting pH to 2.5, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 2:4:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 20mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph and analyzes.The chromatographic condition adopted is: chromatographic column: ODS post; Flow velocity: 0.4 ~ 1.2ml/min; Determined wavelength: 150nm; Column temperature: 30 DEG C; Sample size: 10 μ l.
Embodiment 3: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 27.22g, be diluted with water to the potassium dihydrogen phosphate that 4000ml obtains 0.05mol/L, with phosphorus acid for adjusting pH to 3, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 3:3:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 15mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph and analyzes.The chromatographic condition adopted is: chromatographic column: ODS post; Flow velocity: 0.4 ~ 1.2ml/min; Determined wavelength: 200nm; Column temperature: 40 DEG C; Sample size: 10 μ l.
Embodiment 4: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 38.11g, be diluted with water to the potassium dihydrogen phosphate that 4000ml obtains 0.07mol/L, with phosphorus acid for adjusting pH to 3.5, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 4:2:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 30mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph and analyzes.The chromatographic condition adopted is: chromatographic column: ODS post; Flow velocity: 0.4 ~ 1.2ml/min; Determined wavelength: 250nm; Column temperature: 50 DEG C; Sample size: 15 μ l.
Embodiment 5: a kind of high performance liquid chromatography detects the method for 3-amino-2-caprolactam, and it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 48.99g, be diluted with water to the potassium dihydrogen phosphate that 4000ml obtains 0.09mol/L, with phosphorus acid for adjusting pH to 4, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 5:1:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 25mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph and analyzes.The chromatographic condition adopted is: chromatographic column: ODS post; Flow velocity: 0.4 ~ 1.2ml/min; Determined wavelength: 300nm; Column temperature: 60 DEG C; Sample size: 20 μ l.
In each embodiment, 3-amino-2-caprolactam testing result is in table 1.
Table 1 each embodiment testing result table
| Title | Retention time (min) | Peak area (A) | Symmetrical factor |
| Embodiment 1 | 10.134 | 2988.644 | 0.93 |
| Embodiment 2 | 11.058 | 3001.352 | 0.95 |
| Embodiment 3 | 11.621 | 3019.682 | 0.98 |
| Embodiment 4 | 12.112 | 3088.533 | 0.96 |
| Embodiment 5 | 11.353 | 3067.221 | 0.92 |
Table 1 illustrates, under embodiment 3 condition, the symmetry of gained chromatographic peak is best, and therefore the chromatographic condition of embodiment 3 is more excellent.
Below by way of description of test beneficial effect of the present invention:
1, method specificity checking
(1) sample source
No. 1 liquid: blank negative solution, by prescription preparation not containing the solution of lysine;
No. 2 liquid: amino acid injection, Kelun Pharm Ind Co., Ltd., Sichuan's pilot sample.
(2) sample preparation
1. standard: measure No. 1, No. 2 each 1ml of solution respectively in 10ml volumetric flask, be diluted to scale by mobile phase A, obtain final product.
2. Oxidative demage: getting No. 1, No. 2 each 100ml of solution, to add 30% superoxol be after 0.1ml, respectively at 24h under 2h, room temperature under room temperature, 2h at 80 DEG C.
3. alkali destroys: get No. 1, No. 2 solution appropriate, adjusts pH to be after 12, room temperature 24h, 121 DEG C of sterilizing 2h respectively, then adjust pH to be 7.0 with concentrated hydrochloric acid with 5mol/L sodium hydroxide solution.
4. high temperature: get No. 1, No. 2 solution appropriate, in 121 DEG C of sterilizings 2h, 4h.
5. acid destroys: get No. 1, No. 2 solution appropriate, and adjust pH to be after 2 with concentrated hydrochloric acid, room temperature places 24h, 121 DEG C of sterilizings 2h, 4h respectively, then is 7.0 with 5mol/L sodium hydroxide solution tune pH.
6. illumination destroys: get No. 1, No. 2 solution appropriate, sterilizing 12min at 121 DEG C, places 10d in 4500lx lighting box, gets 0d, 10d sample determination.Point get above sample and carry out stratographic analysis by the chromatographic condition sample introduction 10 μ l drafted, the results are shown in Table 2.
Table 2 shakedown test findings table
Note: " n.a " expression does not detect.
(3) test findings shows: 1. need testing solution (amino acid injection) does not have 3-amino-2-caprolactam impurity to produce under non-degradation condition; 2. need testing solution (amino acid injection) is through sterilizing (at 121 DEG C 12min), and after illumination destroys 0d, 10d, 3-amino-2-caprolactam content is substantially constant, illustrates that lysine is to illumination-insensitive; 3. need testing solution (amino acid injection) all produces 3-amino-2-caprolactam under high temperature, acid destruction, alkali failure condition, and along with the rising 3-amino-2-caprolactam content of temperature in rising trend, and under three conditions, the 3-amino-2-caprolactam peak area produced under alkali failure condition is maximum; 4. under Oxidative demage condition, 3-amino-2-caprolactam does not have destruction, illustrates that lysine is more stable to oxygen; 5. lysine auxiliary material blank solution does not all disturb the detection of 3-amino-2-caprolactam under various failure condition.Therefore, the method specificity is better.
2, linear method checking
(1) take 3-amino-2-caprolactam hydrochloride reference substance 13.60mg and be placed in 25ml volumetric flask, be diluted to scale by water-soluble solution, reference substance storing solution must be mixed, precision measures this storing solution, the solution of variable concentrations is become by table 3 stepwise dilution, be numbered 1 ~ 12#, by drafting chromatographic condition, sample 10 μ l to analyze, 3-amino-2-caprolactam peak area and concentration linear relationship are shown in Fig. 1, the chromatogram of limit concentration 100% is shown in that (retention time is material corresponding to 11.460 places is 3-amino-2-caprolactam to Fig. 2, retention time is material corresponding to 29.085 places is 2-piperidones), test findings is in table 4.
Table 33-amino-2-caprolactam linear relationship investigates result table
Table 43-amino-2-caprolactam detectability, quantitative limit and range of linearity conclusive table
| Title | Numerical value |
| Detectability (μ g/ml) | 0.020 |
| Quantitative limit (μ g/ml) | 0.066 |
| The range of linearity (μ g/ml) | 0.066～410.80 |
| Regression equation | y＝76.1800x+72.5397 |
| Correlation coefficient r | 0.9998 |
| Minimum detectable activity (%) | 0.000002％ |
| Minimum quantitative amount (%) | 0.000007％ |
| Limit concentration (μ g/ml) | 50 |
| Sample introduction concentration (μ g/ml) | 5 |
| Standard limits (%) | 0.005％ |
Table 4 illustrates, is method detectability with baseline noise 3 ~ 5 times, the quantitative limit being method with more than 10 of baseline noise times, then 3-amino-2-caprolactam detectability concentration of the present invention is 0.02 μ g/ml, and quantitative limit concentration is 0.066 μ g/ml.The bound requirements must not crossing 0.005% by concentration calculates, and 0.13% of 3-amino-2-caprolactam limit concentration can be quantitative, and 0.04% of limit concentration can detect.
3, quantitative limit repeatability
Get quantitative limit concentration parallel sample introduction 6 pin to investigate, test findings is in table 5.
Table 5 quantitative limit replica test result table
Table 5 illustrates, this method quantitative limit is reproducible.
4, accuracy
By quantitative limit concentration, limit concentration (50 μ g/ml) 20%, 50%, 100%, 150%, 200% carry out recovery test.
(1) sample preparation
20%: the sample 5.0ml (n=3) getting amino acid injection is placed in 50ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 50.19 μ g/ml, be diluted to scale by mobile phase A, obtain final product;
50%: the sample 2.0ml (n=3) getting amino acid injection is placed in 20ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 50.19 μ g/ml, be diluted to scale by mobile phase A, obtain final product;
100%: the sample 1.0ml (n=3) getting amino acid injection is placed in 10ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 50.19 μ g/ml, be diluted to scale by mobile phase A, obtain final product;
150%: the sample 2.0ml (n=3) getting amino acid injection is placed in 20ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 3.0ml concentration is 50.19 μ g/ml respectively, be diluted to scale by mobile phase A, obtain final product;
200%: the sample 1.0ml (n=3) getting amino acid injection is placed in 10ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 2.0ml concentration is 50.19 μ g/ml respectively, be diluted to scale by mobile phase A, obtain final product.
Measure above-mentioned need testing solution 10 μ l and inject high performance liquid chromatograph, record chromatogram, calculate the recovery, test findings is in table 6 and table 7.Recovery computing formula is as follows:
Table 6 accuracy test scheme table
| Numbering | Concentration (μ g/ml) | Add volume (ml) | Reclaim addition (%) |
| 1～3# | 1.0038 | 1 | 20 |
| 4～6# | 2.5095 | 2 | 50 |
| 7～9# | 5.019 | 1 | 100 |
| 10～12# | 7.5285 | 2 | 150 |
| 13～15# | 10.038 | 1 | 200 |
Table 73-amino-2-caprolactam recovery test result table
Table 7 illustrates, the 3-amino-2-caprolactam recovery of the present invention is high, and average recovery rate reaches 99.42%.
5, Precision Experiment
1. replica test, the sample 1ml getting amino acid injection is placed in 10ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 49.08 μ g/ml, constant volume is diluted by mobile phase A, parallel preparation 6 parts of need testing solutions, according to drafting chromatographic condition analysis, it the results are shown in Table 8.
2. Intermediate precision test, in the different time, the sample 1ml being got amino acid injection by different operating personnel (A, B) puts in 10ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 49.08 μ g/ml, constant volume is diluted by mobile phase A, parallel preparation 6 parts of need testing solutions, according to drafting chromatographic condition analysis, it the results are shown in Table 8.
Table 83-amino-2-caprolactam Precision test result table
Table 8 illustrates, it is good that 3-amino-2-caprolactam content of the present invention measures precision, and RSD (n=12) is 0.37%.
6, stability of solution experiment
The sample 1ml getting amino acid injection is placed in 10ml volumetric flask, add the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 49.08 μ g/ml, constant volume is diluted by mobile phase A, put in ambient temperatare, respectively at 0h, 2h, 4h, 8h, 12h, 16h, 24h, 36h sample analysis, it the results are shown in Table 9.
Table 9 solution stability testing result table
Table 9 illustrates, test solution 3-amino-2-caprolactam concentration after ambient temperatare puts 36h keeps stable, and RSD is that 0.54%, the 3-amino-2-caprolactam recovery keeps stable, and RSD is 0.55%, shows that stability of solution is good.
7, durability experiment
The sample 1ml getting amino acid injection is placed in 10ml volumetric flask, adds the 3-amino-2-caprolactam contrast storing solution that 1.0ml concentration is 49.08 μ g/ml, with mobile phase A dilution, and constant volume.
The chromatographic condition drafted is:
Flow velocity: 0.32ml/min, 0.8ml/min, 0.5ml/min, 1.2ml/min;
Column temperature: 35 ± 5 DEG C;
Wavelength: 200nm ± 5nm;
Mobile phase: pH is 3.0 ± 2;
Chromatographic column 1:Shimadzu, InertsilODS-3,1A7140875;
Chromatographic column 2:CAPCELLPAKC18AQ, A6AD03206.
According to the chromatographic condition drafted, we do the fine setting of following chromatographic condition in pacing items, investigate the durability of this chromatographic condition, and the need testing solution got under replica test item is tested, and test findings is in table 10.
Table 10 method serviceability test result table
Table 10 illustrates, when there is trickle change in column temperature, determined wavelength, flow velocity, the recovery determining 3-amino-2-caprolactam with differ very little under pacing items, show that durability of the present invention is good.
In this test, the work gradient of high performance liquid chromatograph is as shown in table 11.
The work gradient table of this experimental liquid of table 11 chromatography
| Time (min) | A(％) | B(％) | Flow rate of mobile phase (ml/min) |
| 0 | 100 | 0 | 0.4 |
| 15.00 | 100 | 0 | 0.4 |
| 16.00 | 100 | 0 | 1.0 |
| 38.00 | 100 | 0 | 1.0 |
| 38.10 | 90 | 10 | 1.2 |
| 43.00 | 90 | 10 | 1.2 |
| 43.10 | 100 | 0 | 1.2 |
| 53.00 | 100 | 0 | 1.2 |
| 53.10 | 100 | 0 | 0.4 |
| 55.00 | 100 | 0 | 0.4 |
Claims (4)
1. high performance liquid chromatography detects a method for 3-amino-2-caprolactam, it is characterized in that, adopts following chromatographic condition:
Chromatographic column: ODS post;
Mobile phase A: potassium dihydrogen phosphate;
Mobile phase B: the mixed aqueous solution of methyl alcohol, acetonitrile;
Flow velocity: 0.4 ~ 1.2ml/min;
Determined wavelength: 100 ~ 300nm;
Column temperature: 20 ~ 60 DEG C;
Sample size: 5 ~ 20 μ l.
2. a kind of high performance liquid chromatography according to claim 1 detects the method for 3-amino-2-caprolactam, and it is characterized in that, described determined wavelength is 200nm, and column temperature is 35 DEG C, and sample size is 10 μ l.
3. a kind of high performance liquid chromatography according to claim 1 detects the method for 3-amino-2-caprolactam, it is characterized in that, described mobile phase A is the potassium dihydrogen phosphate of 0.01 ~ 0.09mol/L, described Mobile phase B is the mixed aqueous solution of methyl alcohol, acetonitrile, and the volume ratio of methyl alcohol, acetonitrile and water is 1 ~ 5:1 ~ 5:1.
4. a kind of high performance liquid chromatography according to claim 1 detects the method for 3-amino-2-caprolactam, and it is characterized in that, it comprises the following steps:
S1. mobile phase preparation:
(1) take potassium dihydrogen phosphate 5.44 ~ 48.99g, be diluted with water to 4000ml, with phosphorus acid for adjusting pH to 2 ~ 4, after suction filtration is ultrasonic, obtain mobile phase A;
(2) volume ratio of compounding methanol, acetonitrile and water is the solution of 1 ~ 5:1 ~ 5:1, shakes up and obtains Mobile phase B;
S2. reference substance solution preparation:
(1) taking 3-amino-2-caprolactam 10 ~ 30mg joins in 50ml volumetric flask, dissolves and be settled to volumetric flask scale mark by mobile phase A, obtains 3-amino-2-caprolactam reference substance storing solution after shaking up;
(2) measure 3-amino-2-caprolactam reference substance storing solution 1ml to join in 100ml volumetric flask, add mobile phase A and be settled to volumetric flask scale mark, after shaking up, obtain reference substance solution;
S3. need testing solution preparation: measure amino acid injection 1ml and join in 10ml volumetric flask, add water and be settled to volumetric flask scale mark, obtain need testing solution after shaking up;
S4. chromatogram detects: get need testing solution and reference substance solution, injects high performance liquid chromatograph, carries out efficient liquid phase chromatographic analysis according to the condition described in any one of Claims 1 to 4.
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