CN111855864A - Gas chromatographic analysis method of dimethyl cyclopropyl ether and neopentyl glycol - Google Patents
Gas chromatographic analysis method of dimethyl cyclopropyl ether and neopentyl glycol Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 62
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 title claims abstract description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 49
- -1 dimethyl cyclopropyl Chemical group 0.000 title claims abstract description 41
- 238000004587 chromatography analysis Methods 0.000 title claims abstract description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000004817 gas chromatography Methods 0.000 claims abstract description 26
- 238000004458 analytical method Methods 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 238000005070 sampling Methods 0.000 claims abstract description 13
- 238000010813 internal standard method Methods 0.000 claims abstract description 10
- 230000014759 maintenance of location Effects 0.000 claims abstract description 10
- 230000000630 rising effect Effects 0.000 claims abstract description 10
- 239000000523 sample Substances 0.000 claims description 95
- 239000007789 gas Substances 0.000 claims description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000012086 standard solution Substances 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 26
- 239000012224 working solution Substances 0.000 claims description 18
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical compound CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 claims description 16
- 238000001514 detection method Methods 0.000 claims description 15
- 239000012488 sample solution Substances 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012159 carrier gas Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000010453 quartz Substances 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005303 weighing Methods 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000004445 quantitative analysis Methods 0.000 abstract description 3
- QTCNKIZNNWURDV-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO.OCC(C)(C)CO QTCNKIZNNWURDV-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 14
- 229960001680 ibuprofen Drugs 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 8
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- CAZPRAORHCOIHC-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CCl CAZPRAORHCOIHC-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000010606 normalization Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003908 quality control method Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- RVGLUKRYMXEQAH-UHFFFAOYSA-N 3,3-dimethyloxetane Chemical compound CC1(C)COC1 RVGLUKRYMXEQAH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FMPSBYPOYORZPK-UHFFFAOYSA-N 1-(2,3-dimethylcyclopropyl)oxy-2,3-dimethylcyclopropane Chemical compound CC1C(C)C1OC1C(C)C1C FMPSBYPOYORZPK-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- NUFBGJAEANEZKW-UHFFFAOYSA-N cyclopropyloxycyclopropane Chemical compound C1CC1OC1CC1 NUFBGJAEANEZKW-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QFTKWLWBDDNQLD-UHFFFAOYSA-N methyl 3,3,3-trihydroxypropanoate Chemical compound OC(CC(=O)OC)(O)O QFTKWLWBDDNQLD-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012421 spiking Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
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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
-
- 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
- G01N30/06—Preparation
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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
- G01N30/60—Construction of the column
-
- 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
- G01N30/68—Flame ionisation 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
- G01N2030/045—Standards internal
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The invention relates to a gas chromatography analysis method of dimethylcyclopropane (2, 2-dimethyl-1, 3-epoxypropane) and neopentyl glycol (2, 2-dimethyl-1, 3-propanediol), which comprises the preparation of analysis samples, the analysis conditions of gas chromatography and qualitative and quantitative methods; the chromatographic analysis conditions were: sampling amount is 1 muL; the gas chromatography conditions are that the temperature is kept for 4 minutes at 60 ℃, then the temperature is kept for 10 minutes from rising to 250 ℃ per minute at 15 ℃, a TG-1701ms chromatographic column with the specification of 30m multiplied by 0.25mm multiplied by 0.25 mu m and a hydrogen flame detector are adopted; the retention time of the dimethyl cyclopropyl ether is 2.278min, and the retention time of the neopentyl glycol is 8.983 min; the quantitative method used was internal standard method, the internal standard was ethylene glycol, and the residence time of the internal standard was 6.650 min. The method can realize effective separation of various impurities, and has the advantages of simplicity, rapidness, stability, good chromatographic peak shape, high accuracy, good reproducibility and the like.
Description
Technical Field
The invention belongs to the technical field of preparation of cyclopropyl ether, and particularly relates to a gas chromatographic analysis method of dimethyl cyclopropyl ether and a gas chromatographic analysis method of neopentyl glycol.
Background
The production process of neopentyl glycol (2, 2-dimethyl-1, 3-propanediol) can be divided into two routes according to the difference of the production process: the isobutyraldehyde route and the halohydrin route. In the isobutyraldehyde route, isobutyraldehyde and formaldehyde are used as raw materials, a condensation reaction is carried out to generate chemical intermediate trihydroxy methyl propionate, and neopentyl glycol is generated through reduction. The production method can be divided into a sodium formate method and a condensation catalytic hydrogenation method according to different reduction modes of converting methyl trihydroxypropionate into neopentyl glycol. The halogenated alcohol route uses waste liquid containing 2, 2-dimethyl-3-chloropropanol generated in the production of ibuprofen and other processes as a starting material, and neopentyl glycol is generated through two steps of epoxidation reaction and hydrolysis reaction, and the development of the process depends on the production mode and scale of medicaments such as ibuprofen to a great extent.
The process route of the halohydrin is that isobutylbenzene is used as an initial raw material, an intermediate is not separated, and the isobutylbenzene is subjected to molecular rearrangement, hydrolysis and esterification under the catalysis of chloroketone and ketal until the ibuprofen finished product is separated. Neopentyl glycol is needed as a raw material when ketal is prepared, ibuprofen ester is generated after rearrangement of ketal, 2-dimethyl-3-chloropropanol waste liquid is generated while ibuprofen is generated by hydrolysis of ibuprofen ester, and the amount of the waste liquid is determined according to the production scale of ibuprofen.
The obtained 2, 2-dimethyl-3-chloropropanol waste liquid has complex components, and the purity required by production is difficult to obtain by a method for directly hydrolyzing to generate neopentyl glycol. The 2, 2-dimethyl-3-chloropropanol can be epoxidized to generate low-boiling point dimethyl cyclopropyl ether (2, 2-dimethyl-1, 3-propylene oxide) and distilled by adopting a rectification method, and the generated dimethyl cyclopropyl ether is subjected to hydrolysis reaction to generate neopentyl glycol. This process is achieved in two steps, namely an epoxidation reaction and a hydrolysis reaction.
The epoxidation reaction equation of 2, 2-dimethyl-3-chloropropanol is as follows:
the dimethyl cyclopropyl ether molecule contains a four-membered ring and has a dimethyl structure, and no hydrogen atom exists at a beta position, so that the dimethyl cyclopropyl ether has high chemical stability and thermal stability, and can be hydrolyzed under the catalytic action of protonic acid to generate neopentyl glycol. The hydrolysis equation of the dimethyl cyclopropane is as follows:
the method is very practical in ibuprofen production, can achieve the purpose of recovering and reusing neopentyl glycol to reduce the production cost of ibuprofen products, and simultaneously greatly reduces environmental pollution. The recovered neopentyl glycol can be used directly in the ketal reaction in the ibuprofen production process described above.
At present, most of documents use a gas chromatography area normalization method, conditions of a chromatographic column are unclear, product impurities in actual production are complex, a sample contains a large amount of moisture (20% -80%), the component of water under common gas conditions cannot produce peaks in the chromatogram, and response factor differences among the components in the gas chromatography are large, so that the content of the dimethyl cyclopropyl ether and the neopentyl glycol cannot be accurately measured by simply using the area normalization method, and the influence on the production process is large.
Disclosure of Invention
The invention aims to provide a gas chromatographic analysis method of dimethyl cyclopropyl ether and a gas chromatographic analysis method of neopentyl glycol, which can solve the technical problems that the existing gas chromatographic area normalization method is used, the chromatographic column condition is not clear, the difference of response factors among components in gas chromatography is large, the corresponding components cannot peak in the chromatogram, and the contents of the dimethyl cyclopropyl ether and the neopentyl glycol cannot be accurately measured simply by using the area normalization method.
In order to achieve the purpose, the invention provides a gas chromatographic analysis method of dimethyl cyclopropane and a gas chromatographic analysis method of neopentyl glycol, wherein a gas chromatograph is used in the method, a TG-1701ms chromatographic column is selected, and a polar column in the chromatographic column can obtain better peak effect, has wider linear range, is suitable for analyzing dimethyl cyclopropane and neopentyl glycol samples with different unknown concentrations, and can well analyze impurities such as dimer, trimer and the like; meanwhile, the internal standard method is particularly adopted for quantitative analysis in consideration of impurities which can not generate peaks under the gas chromatography condition in the sample. Wherein the dimethylcyclopropane ether is 2, 2-dimethyl-1, 3-epoxypropane, and the neopentyl glycol is 2, 2-dimethyl-1, 3-propanediol.
In order to achieve the above object, the present invention provides a method for gas chromatography analysis of dimethylcyclopropane, comprising the steps of:
preparing an internal standard solution, dissolving an internal standard substance in methanol to form the internal standard solution, wherein the internal standard substance comprises any one of ethylene glycol, propylene glycol, 1,3, 5-trimethylbenzene or toluene, and the mass-volume concentration of the internal standard substance in the internal standard solution is 250-350 g/L; and
preparing a sample solution to be detected, dissolving a sample in the internal standard solution, and dissolving 0.1g-2g of the sample in each milliliter of the internal standard solution, wherein the sample contains dimethyl cyclopropyl ether;
setting chromatographic detection conditions, namely providing a gas chromatograph, wherein the chromatographic detection conditions of the gas chromatograph comprise one or more of the following conditions:
a) temperature rising procedure: the initial temperature is kept at 50-70 ℃ for 2-6 min, and the temperature is increased to 230-270 ℃ at 5-25 ℃/min and kept for 8-13 min;
b) flow rate of carrier gas: 0.5mL/min-1.5 mL/min;
c) sample introduction volume: 0.2-2 μ L;
d) sample inlet temperature: 230-270 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 40: 1-60: 1;
g) detector temperature: 230-270 ℃;
h) hydrogen flow rate: 30mL/min-50 mL/min;
i) air flow rate: 350mL/min-450 mL/min;
j) flow rate of the mixture: 30mL/min-40 mL/min; and
and drawing a standard curve by using a gas chromatography internal standard method, taking a plurality of samples with different masses, respectively obtaining a standard working solution concentration gradient according to the step S2 of preparing the sample to be detected, injecting the standard working solution concentration gradient into the gas chromatograph of the step S3 of setting the chromatographic detection condition for analysis, and drawing the standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample.
Further, the chromatographic detection conditions of the gas chromatograph in the step S2 of preparing the sample solution to be detected are as follows:
a) temperature rising procedure: the initial temperature is 60 deg.C for 4min, and the temperature is increased to 250 deg.C at 15 deg.C/min for 10min
b) Flow rate of carrier gas: 1.0 mL/min;
c) sample introduction volume: 0.2-2 μ L;
d) sample inlet temperature: 250 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 50: 1;
g) detector temperature: 280 ℃;
h) hydrogen flow rate: 40 mL/min;
i) air flow rate: 400 mL/min;
j) flow rate of the mixture: 35 mL/min.
Further, the gas chromatograph in the step of configuring the sample solution to be detected is configured with a hydrogen flame monitor; the chromatographic column in the gas chromatograph comprises a quartz capillary chromatographic column, and the specification of the quartz capillary chromatographic column is as follows: TG-1701ms 30 m.times.0.25 mm.times.0.25. mu.m.
Further, the step of drawing a standard curve by the gas chromatography internal standard method specifically comprises the following steps:
preparing a concentration gradient of a standard working solution, accurately weighing 0.01g, 0.04g, 0.08g, 0.1g and 0.2g of the sample respectively, placing the sample in a 10mL volumetric flask, adding 1mL of an internal standard solution, and performing constant volume shaking uniformly by using methanol;
drawing a standard curve, namely injecting the concentration gradient of the standard working solution into a gas chromatograph for analysis; and (4) determining by retention time, and drawing a standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample.
Further, the regression coefficient of the standard curve in the step of drawing the standard curve is greater than 0.9.
In order to achieve the above object, the present invention provides the method for gas chromatography of neopentyl glycol, which is different from the above-described method for gas chromatography of dimethyl cyclopropyl ether only in that neopentyl glycol is contained in the sample instead of dimethyl cyclopropyl ether in the step of preparing a sample solution to be tested.
The invention has the beneficial effects that the novel gas chromatographic analysis method for the dimethyl cyclopropyl ether and the gas chromatographic analysis method for the neopentyl glycol are provided, the technical blank in the corresponding field is filled, the advantages of simplicity, rapidness, stability, good chromatographic peak shape, high accuracy, good reproducibility and the like are achieved, and the method has important practical significance in the fields of quality analysis, quality control and the like of the dimethyl cyclopropyl ether and the neopentyl glycol.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below.
FIG. 1 is a flow chart of the gas chromatographic analysis method of the dimethyl cyclopropyl ether provided by the invention;
FIG. 2 is an analysis spectrum of the standard sample of the dimethyl cyclopropane ether and the neopentyl glycol in example 1 of the present invention;
FIG. 3 is an analysis spectrum in example 2 of the present invention.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to make and use the present invention, and is provided in the accompanying drawings for describing and enabling those skilled in the art how the present invention may be embodied and executed. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein, but rather should be construed as limited to the embodiments set forth herein.
In order to achieve the above object, as shown in fig. 1, the method for analyzing dimethyl cyclopropyl ether by gas chromatography provided by the present invention comprises steps S1-S4. The sequence of steps S1-S3 can be adjusted reasonably according to actual situations, and the application is not limited strictly.
S1, preparing an internal standard solution, dissolving an internal standard substance in methanol to form the internal standard solution, wherein the internal standard substance comprises any one of ethylene glycol, propylene glycol, 1,3, 5-trimethylbenzene or toluene, and the mass-volume concentration of the internal standard substance in the internal standard solution is 250-350 g/L; the internal standard substance is preferably ethylene glycol, 30.00g (accurate to 0.0001g) of ethylene glycol is accurately weighed and placed in a 100mL volumetric flask, the volume is determined by methanol, shaking is carried out uniformly, and in order to ensure the use of multiple batches of internal standard liquid, the weighing error of the ethylene glycol is less than 0.5%.
S2, preparing a sample solution to be detected, dissolving a sample in the internal standard solution, and dissolving 0.1g-2g of the sample in each milliliter of the internal standard solution, wherein the sample contains the dimethyl cyclopropyl ether. Specifically, the method can be applied to hydrolysis lab scale experimental research and can also be used for hydrolysis sample analysis in industrial production. Regarding the experimental sample of the small test, 0.1g-2g (accurate to 0.0001g) of hydrolysis reaction sample (as example 1 below) is put into a 10mL volumetric flask, 1mL of internal standard solution is added, and the volume is determined by methanol and shaken up; in the production, the homogeneous effect of a sample is not ideal, the solubility of the dimethyl cyclopropane in water is about 2%, impurities are more in the production reaction, the sample must be completely dissolved for accurate analysis, the representativeness of the sample is ensured, and when the sampling amount is less than 5g, the analysis data error is large, the data is unstable, so that the sampling amount of the sample is preferably more than or equal to 5 g. The relationship between the sample size and the analytical data is shown in Table 1.
TABLE 1 correlation of sample size and analytical results
| Sample numbering | Sample size g | Content of dimethyl cyclopropyl ether% | Neopentyl glycol content% |
| 1 | 0.5225 | 1.5024 | 10.0665 |
| 2 | 1.0252 | 1.6288 | 10.3258 |
| 3 | 5.2361 | 1.8025 | 11.1911 |
| 4 | 6.3115 | 1.8111 | 11.1185 |
| 5 | 10.3360 | 1.8025 | 11.1624 |
| 6 | 15.2211 | 1.8058 | 11.1745 |
Therefore, 5.0g-20.0g (accurate to 0.01g) of sample is sampled, added with methanol to a volume of 100mL volumetric flask and shaken to be constant volume, then 1mL of sample is taken by a pipette and put in a 10mL volumetric flask, added with 1mL of internal standard solution and shaken to be constant volume by methanol, filtered by a filter membrane and then injected for analysis.
S3, setting chromatographic detection conditions, providing a gas chromatograph, wherein the chromatographic detection conditions of the gas chromatograph comprise one or more of the following conditions:
a) temperature rising procedure: the initial temperature is kept at 50-70 ℃ for 2-6 min, and the temperature is increased to 230-270 ℃ at 5-25 ℃/min and kept for 8-13 min;
b) flow rate of carrier gas: 0.5mL/min-1.5 mL/min;
c) sample introduction volume: 0.2-2 μ L;
d) sample inlet temperature: 230-270 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 40: 1-60: 1;
g) detector temperature: 230-270 ℃;
h) hydrogen flow rate: 30mL/min-50 mL/min;
i) air flow rate: 350mL/min-450 mL/min;
j) flow rate of the mixture: 30mL/min-40 mL/min.
Wherein, the chromatographic detection conditions of the gas chromatograph are preferably as follows:
a) temperature rising procedure: the initial temperature is 60 deg.C for 4min, and the temperature is increased to 250 deg.C at 15 deg.C/min for 10min
b) Flow rate of carrier gas: 1.0 mL/min;
c) sample introduction volume: 0.2-2 μ L;
d) sample inlet temperature: 250 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 50: 1;
g) detector temperature: 280 ℃;
h) hydrogen flow rate: 40 mL/min;
i) air flow rate: 400 mL/min;
j) flow rate of the mixture: 35 mL/min.
The gas chromatograph is provided with a hydrogen flame monitor; the chromatographic column in the gas chromatograph comprises a quartz capillary chromatographic column, and the specification of the quartz capillary chromatographic column is as follows: TG-1701ms 30 m.times.0.25 mm.times.0.25. mu.m.
S4, drawing a standard curve by a gas chromatography internal standard method, taking a plurality of samples with different masses, respectively obtaining a concentration gradient of a standard working solution according to the step S2 of preparing a sample to be detected, injecting the concentration gradient of the standard working solution into the gas chromatography of the step S3 of setting chromatographic detection conditions for analysis, and drawing the standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample.
In this embodiment, the step S4 of drawing a standard curve by using the gas chromatography internal standard method specifically includes a step of configuring a standard working solution concentration gradient and a step of drawing a standard curve.
In the step of preparing the concentration gradient of the standard working solution, 0.01g, 0.04g, 0.08g, 0.1g and 0.2g of the sample are accurately weighed respectively and placed in a 10mL volumetric flask, 1mL of internal standard solution is added, and methanol is used for constant volume and shaking up.
In the step of drawing the standard curve, injecting the concentration gradient of the standard working solution into a gas chromatograph for analysis; the retention time is characterized by the fact that the time of the dimethyl cyclopropane ether is 2.278min, and the retention time of the neopentyl glycol is 8.893 min. The internal standard substance ethylene glycol peak time is 6.650min, and a standard curve is drawn according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample. The obtained standard curve y of the dimethyl cyclopropyl ether is 8.8396x-0.0027, and the regression coefficient is 0.9996; neopentyl glycol standard curve y 9.3496x-0.0107, regression coefficient 0.9996.
In this embodiment, the regression coefficient of the standard curve in the step S42 of drawing the standard curve is greater than 0.9.
In order to achieve the above object, the present invention provides the method for gas chromatography of neopentyl glycol, which is different from the above-described method for gas chromatography of dimethyl cyclopropyl ether only in that neopentyl glycol is contained in the sample instead of dimethyl cyclopropyl ether in the step of preparing a sample solution to be tested. The gas chromatographic analysis method of neopentyl glycol can refer to the flow chart shown in figure 1. The relationship between the sample size and the analytical data is shown in Table 1.
The invention has the beneficial effects that the novel gas chromatographic analysis method for the dimethyl cyclopropyl ether and the gas chromatographic analysis method for the neopentyl glycol are provided, the technical blank in the corresponding field is filled, the advantages of simplicity, rapidness, stability, good chromatographic peak shape, high accuracy, good reproducibility and the like are achieved, and the method has important practical significance in the fields of quality analysis, quality control and the like of the dimethyl cyclopropyl ether and the neopentyl glycol.
The present invention will be described in further detail with reference to examples.
Example 1
1.1 reagents and instruments
Methanol: analyzing and purifying;
ethylene glycol: analyzing and purifying;
dimethylpropaneether standards: the self-made purity is 99.2%;
neopentyl glycol standards: the purity of Shanghai medicine is 99.5%;
analytical balance: 0.0001 g;
organic phase microporous filter membrane: 0.22 μm;
gas chromatograph: 7980A, Agilent, with hydrogen flame detector, with G4513A autosampler;
capillary chromatographic column: TG-1701ms 30 m.times.0.25 mm.times.0.25 μm, Sammerfoil.
1.2 chromatographic methods
a) Temperature rising procedure: the initial temperature is 60 deg.C for 4min, and the temperature is increased to 250 deg.C at 15 deg.C/min for 10min
b) Flow rate of carrier gas: 1.0 mL/min;
c) sample introduction volume: 1.0 μ L;
d) sample inlet temperature: 250 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 100: 1;
g) detector temperature: 280 ℃;
h) hydrogen flow rate: 40 mL/min;
i) air flow rate: 400 mL/min;
j) flow rate of the mixture: 35 mL/min.
1.3 drawing a standard curve
The standard working solutions were separately collected and subjected to chromatographic analysis under the chromatographic conditions of 1.2.
And drawing a standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured at each concentration in the concentration gradient and the weight of the standard sample, wherein the correlation coefficient is required to be greater than 0.9, and preferably greater than 0.999. The obtained standard curve y of the dimethyl cyclopropyl ether is 8.8396x-0.0027, and the regression coefficient is 0.9996; neopentyl glycol standard curve y 9.3496x-0.0107, regression coefficient 0.9996.
1.4 measurement and calculation of samples
Taking a sample in the acidification process stage, wherein the sample contains the dimethyl cyclopropyl ether, the neopentyl glycol and impurities thereof, accurately weighing the sample, adding 1mL of internal standard solution with the mass of 1.0011g and 10mL, adding methanol to a constant volume, shaking up uniformly, filtering by using a 0.22 mu m filter membrane, and then carrying out sample injection analysis.
As shown in FIG. 2, the chromatogram is an analysis spectrum of the dimethylcyclopropane ether and the neopentyl glycol, and the ordinate of the chromatogram is a response signal of a detector and the abscissa of the chromatogram is time. The response signal of the detector is represented by current values A, mA, uA, nA and pA, and the current value is pA in the application. The time unit of the abscissa is min. Wherein the retention time of the dimethyl cyclopropyl ether is 2.278min, the retention time of the neopentyl glycol is 8.893min, the retention time of the internal standard substance is 6.658min, and the content of the dimethyl cyclopropyl ether is 1.08364% and the content of the neopentyl glycol is 8.30368% are obtained according to a standard curve.
1.5 method repeatability
Precisely measuring the sample solution, injecting into a gas chromatograph for detection, continuously detecting for 5 times, and calculating the Relative Standard Deviation (RSD) of the content, wherein the results are shown in Table 2.
TABLE 2 relative standard deviations of the dimethylcyclopropane and neopentyl glycol
| Sample numbering | Content of dimethyl cyclopropyl ether% | Neopentyl glycol content% |
| 1 | 1.7758 | 8.3090 |
| 2 | 1.9125 | 8.2998 |
| 3 | 1.8891 | 8.3121 |
| 4 | 1.0654 | 8.3077 |
| 5 | 1.1254 | 8.2898 |
| Average value% | 1.08364 | 8.30368 |
| RSD％ | 1.233584 | 0.10823 |
1.6 accuracy test
Different amounts of 3-chloro-2, 2-dimethyl-1-propanol standard were added to sample 1, and the standard recovery was calculated under the same chromatographic conditions, and the data are shown in Table 3.
TABLE 3 spiking recovery of Dimethylcyclopropyl Ether, neopentyl glycol experiment
Example 2
Reagents and instruments, chromatographic conditions, etc. were operated as in example 1.
In example 2, the sampling position is the raw material of the crude product of the produced dimethylcyclopropane ether, 0.1g of the sample is taken, and the sample injection analysis is configured according to the conditions in example 1.
In this example, the chromatogram is analyzed as shown in fig. 3, and the ordinate of the chromatogram in fig. 3 is the response signal of the detector, and the abscissa is time. The response signal of the detector is represented by current values A, mA, uA, nA and pA, and the current value is pA in the application. The unit of time on the abscissa is min. The content of the dimethyl cyclopropyl ether was 85.11% calculated according to the method.
With reference to examples 1 and 2, it can be seen that the gas chromatography analysis method of the present invention can analyze the contents of components in samples each containing dimethylcyclopropane and neopentyl glycol, and can also analyze the contents of components in samples containing only dimethylcyclopropane or only neopentyl glycol.
The invention has the beneficial effects that the novel gas chromatographic analysis method for the dimethyl cyclopropyl ether and the gas chromatographic analysis method for the neopentyl glycol are provided, the technical blank in the corresponding field is filled, the advantages of simplicity, rapidness, stability, good chromatographic peak shape, high accuracy, good reproducibility and the like are achieved, and the method has important practical significance in the fields of quality analysis, quality control and the like of the dimethyl cyclopropyl ether and the neopentyl glycol.
The gas chromatographic analysis method of the dimethylcyclopropane ether, the gas chromatographic analysis method of the neopentyl glycol and the preparation method thereof provided by the invention are described in detail above. It should be understood that the exemplary embodiments described herein should be considered merely illustrative for facilitating understanding of the method of the present invention and its core ideas, and not restrictive. The description of features or aspects in each exemplary embodiment should generally be considered to apply to similar features or aspects in other exemplary embodiments. While the present invention has been described with reference to exemplary embodiments, various changes and modifications may be suggested to one skilled in the art. It is intended that the present invention cover the modifications and variations of this invention provided they come within the spirit and scope of the appended claims and their equivalents and improvements made thereto.
Claims (10)
1. A gas chromatographic analysis method of dimethyl cyclopropyl ether is characterized by comprising the following steps:
preparing an internal standard solution, dissolving an internal standard substance in methanol to form the internal standard solution, wherein the internal standard substance comprises any one of ethylene glycol, propylene glycol, 1,3, 5-trimethylbenzene or toluene, and the mass-volume concentration of the internal standard substance in the internal standard solution is 250-350 g/L;
preparing a sample solution to be detected, dissolving a sample in the internal standard solution, and dissolving 0.1g-2g of the sample in each milliliter of the internal standard solution, wherein the sample contains dimethyl cyclopropyl ether;
setting chromatographic detection conditions, namely providing a gas chromatograph, wherein the chromatographic detection conditions of the gas chromatograph comprise one or more of the following conditions:
a) temperature rising procedure: the initial temperature is kept at 50-70 ℃ for 2-6 min, and the temperature is increased to 230-270 ℃ at 5-25 ℃/min and kept for 8-13 min;
b) flow rate of carrier gas: 0.5mL/min-1.5 mL/min;
c) sample introduction volume: 0.2 muL-2 muL;
d) sample inlet temperature: 230-270 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 40: 1-60: 1;
g) detector temperature: 230-270 ℃;
h) hydrogen flow rate: 30mL/min-50 mL/min;
i) air flow rate: 350mL/min-450 mL/min;
j) flow rate of the mixture: 30mL/min-40 mL/min; and
and drawing a standard curve by using a gas chromatography internal standard method, taking a plurality of samples with different masses, respectively obtaining a standard working solution concentration gradient according to the step of preparing the sample to be detected, injecting the standard working solution concentration gradient into the gas chromatograph with the step of setting chromatographic detection conditions for analysis, and drawing the standard curve according to the corresponding relation between the peak area ratio of the sample to be detected and the internal standard substance in each concentration in the concentration gradient and the weight of the standard sample.
2. The method for gas chromatography of dimethyl cyclopropyl ether according to claim 1, wherein the gas chromatograph in the step of preparing the sample solution to be tested has the following chromatographic test conditions:
a) temperature rising procedure: the initial temperature is 60 deg.C for 4min, and the temperature is increased to 250 deg.C at 15 deg.C/min for 10min
b) Flow rate of carrier gas: 1.0 mL/min;
c) sample introduction volume: 0.2-2 muL;
d) sample inlet temperature: 250 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 50: 1;
g) detector temperature: 280 ℃;
h) hydrogen flow rate: 40 mL/min;
i) air flow rate: 400 mL/min;
j) flow rate of the mixture: 35 mL/min.
3. The method for gas chromatography of dimethyl cyclopropyl ether according to claim 1, wherein said gas chromatograph in said step of placing a sample solution to be tested S2 is equipped with a hydrogen flame monitor; the chromatographic column in the gas chromatograph comprises a quartz capillary chromatographic column, and the specification of the quartz capillary chromatographic column is as follows: TG-1701ms 30m × 0.25mm × 0.25 μm.
4. The method for the gas chromatographic analysis of dimethyl cyclopropane according to claim 1, wherein the step of drawing a standard curve by the gas chromatographic internal standard method specifically comprises the steps of:
preparing a concentration gradient of a standard working solution, accurately weighing 0.01g, 0.04g, 0.08g, 0.1g and 0.2g of the sample respectively, placing the sample in a 10mL volumetric flask, adding 1mL of an internal standard solution, and performing constant volume shaking uniformly by using methanol; and
drawing a standard curve, namely injecting the concentration gradient of the standard working solution into a gas chromatograph for analysis; and (4) performing qualitative determination by using retention time, and drawing a standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample.
5. The method for the gas chromatographic analysis of dimethyl cyclopropane according to claim 4, wherein the regression coefficient of the standard curve in the step of drawing the standard curve is more than 0.9.
6. A gas chromatographic analysis method of neopentyl glycol, characterized by comprising the steps of:
preparing an internal standard solution, dissolving an internal standard substance in methanol to form the internal standard solution, wherein the internal standard substance comprises any one of ethylene glycol, propylene glycol, 1,3, 5-trimethylbenzene or toluene, and the mass-volume concentration of the internal standard substance in the internal standard solution is 250-350 g/L;
preparing a sample solution to be detected, dissolving a sample in the internal standard solution, and dissolving 0.1g-2g of the sample in each milliliter of the internal standard solution, wherein the sample contains neopentyl glycol;
setting chromatographic detection conditions, namely providing a gas chromatograph, wherein the chromatographic detection conditions of the gas chromatograph comprise one or more of the following conditions:
a) temperature rising procedure: the initial temperature is kept at 50-70 ℃ for 2-6 min, and the temperature is increased to 230-270 ℃ at 5-25 ℃/min and kept for 8-13 min;
b) flow rate of carrier gas: 0.5mL/min-1.5 mL/min;
c) sample introduction volume: 0.2 muL-2 muL;
d) sample inlet temperature: 230-270 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 40: 1-60: 1;
g) detector temperature: 230-270 ℃;
h) hydrogen flow rate: 30mL/min-50 mL/min;
i) air flow rate: 350mL/min-450 mL/min;
j) flow rate of the mixture: 30mL/min-40 mL/min; and
and drawing a standard curve by using a gas chromatography internal standard method, taking a plurality of samples with different masses, respectively obtaining a standard working solution concentration gradient according to the step of preparing the sample to be detected, injecting the standard working solution concentration gradient into the gas chromatograph with the step of setting chromatographic detection conditions for analysis, and drawing the standard curve according to the corresponding relation between the peak area ratio of the sample to be detected and the internal standard substance in each concentration in the concentration gradient and the weight of the standard sample.
7. The method for gas chromatography of neopentyl glycol according to claim 6, wherein the chromatographic conditions of the gas chromatograph in the step of preparing the sample solution to be tested are:
a) temperature rising procedure: the initial temperature is 60 deg.C for 4min, and the temperature is increased to 250 deg.C at 15 deg.C/min for 10min
b) Flow rate of carrier gas: 1.0 mL/min;
c) sample introduction volume: 0.2-2 muL;
d) sample inlet temperature: 250 ℃;
e) sample introduction mode: shunting and sampling;
f) the split ratio is as follows: 50: 1;
g) detector temperature: 280 ℃;
h) hydrogen flow rate: 40 mL/min;
i) air flow rate: 400 mL/min;
j) flow rate of the mixture: 35 mL/min.
8. The method for gas chromatography of neopentyl glycol according to claim 6, wherein said gas chromatograph in said step of arranging a sample solution to be tested is arranged with a hydrogen flame monitor; the chromatographic column in the gas chromatograph comprises a quartz capillary chromatographic column, and the specification of the quartz capillary chromatographic column is as follows: TG-1701ms 30m × 0.25mm × 0.25 μm.
9. The method for the gas chromatographic analysis of neopentyl glycol according to claim 6, characterized in that said step of standard curve drawing by means of internal standard methods of gas chromatography comprises in particular the steps of:
preparing a concentration gradient of a standard working solution, accurately weighing 0.01g, 0.04g, 0.08g, 0.1g and 0.2g of the sample respectively, placing the sample in a 10mL volumetric flask, adding 1mL of an internal standard solution, and performing constant volume shaking uniformly by using methanol;
drawing a standard curve, namely injecting the concentration gradient of the standard working solution into a gas chromatograph for analysis; and (4) performing qualitative determination by using retention time, and drawing a standard curve according to the corresponding relation between the peak area ratio of the sample and the internal standard substance measured by each concentration in the concentration gradient and the weight of the standard sample.
10. The method for gas chromatographic analysis of neopentyl glycol according to claim 9, wherein the step of plotting a standard curve has a regression coefficient of greater than 0.9.
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