CN106841409A - A kind of detection method of Pyromellitic Acid hydrogenation reaction - Google Patents
A kind of detection method of Pyromellitic Acid hydrogenation reaction Download PDFInfo
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- CN106841409A CN106841409A CN201510885722.4A CN201510885722A CN106841409A CN 106841409 A CN106841409 A CN 106841409A CN 201510885722 A CN201510885722 A CN 201510885722A CN 106841409 A CN106841409 A CN 106841409A
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- pyromellitic acid
- hydrogenation reaction
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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
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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
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
Abstract
The present invention relates to a kind of detection method of Pyromellitic Acid hydrogenation reaction, the method comprises the following steps：(1) chromatographic condition：Organic acid post；Flow velocity：0.5mL/min；Column temperature：45℃；Sample size：5μL；Mobile phase：The sulfuric acid solution of 0.005M；Detection time：20min；Sample preparation：1. the preparation of standard liquid：Pyromellitic Acid is taken, with flowing phased soln and being diluted in 10mL volumetric flasks, is filtered, it is to be measured；1,2,4,5- cyclohexanetetracarboxylic acids are taken, with flowing phased soln and being diluted in 10mL volumetric flasks, is filtered, it is to be measured；2. prepared by test sample：Testing sample is taken, with flowing phased soln and being diluted in 10mL volumetric flasks, is filtered, it is to be measured；(3) sample detection：Preheater apparatus, the μ L of sample introduction 5 record spectrogram.First examination criteria solution, confirms each component retention time.Each component is distinguished according to retention time, each component content is calculated with area normalization method.By the raw material in invention detection hydrogenation reaction solution, product and impurity, reappearance, sensitivity and the degree of accuracy can meet the requirements.
Description
Technical field
The invention belongs to analysis field, and in particular to a kind of detection method of Pyromellitic Acid hydrogenation reaction.
Background technology
With 1,2,4,5- cyclohexanetetracarboxylic acid dianhydrides are the polyimides of Material synthesis, with good heat resistance, excellent
The good transparency, low-k, high glass transition temperature, low hydroscopicity and the adhesiveness good with metal,
It has broad application prospects in the field such as microelectronics and photoelectron, space flight and aviation.For example：For various electronics
The base material of the liquid crystal display of equipment；The base material of display of organic electroluminescence；The interlayer of solar panel is exhausted
Velum；Semiconductor equipment；Diaphragm；Liquid crystal aligning membrane material etc..
Knowable to prior art, the preparation of 1,2,4,5- cyclohexanetetracarboxylic acid dianhydride is mainly by following reaction：
1st, Pyromellitic Acid Hydrogenation must hydrogenate Pyromellitic Acid；
2nd, hydrogenation Pyromellitic Acid dehydration synthesis 1,2,4,5- cyclohexanetetracarboxylic acid dianhydrides.
1, in the synthesis of 2,4,5- cyclohexanetetracarboxylic acid dianhydrides, the content of Pyromellitic Acid and impurity can be directly influenced
The quality of product, therefore, need to set up effective analysis method in hydrogenation reaction detect Pyromellitic Acid,
The content of hydrogenation Pyromellitic Acid and impurity.
Chinese patent 200980128364 carries out esterification treatment with diazomethane to solution, then is divided with gas-chromatography
Analysis sample, diazomethane is that gas and belonging to when toxic articles are operated is difficult to control in the method, dangerous larger；
Japan Patent 2009191253A surveys gas phase to detect using the methanol solution esterification cyclohexanetetracarboxylic acid of hydrogen chloride
Its purity, but it does not refer to specific implementation method；Chinese patent 2012800215854 is also mentioned by esterification two
Detection reaction solution, specific method is not specified equally.Reaction solution and product purity are detected by the method being esterified,
Not only take time and effort, and easily chromatographic column is damaged with acid catalyzed esterification reaction solution.Therefore, develop a kind of straight
Effective method is connect to analyze the hydrogenation reaction of Pyromellitic Acid be problem urgently to be resolved hurrily.
The content of the invention
The present invention provides a kind of detection method of Pyromellitic Acid hydrogenation reaction, with overcome current detection method it is poorly efficient,
Cumbersome problem.
The object of the present invention is achieved like this：(1) chromatographic condition：Chromatographic column：Organic acid post；Flow velocity：
0.5mL/min；Column temperature：45℃；Sample size：5μL；Mobile phase：The sulfuric acid solution of 0.005M；(2) survey
It is prepared by test agent：Testing sample 10mg is taken, with flowing phased soln and being diluted to 10mL, is filtered；(3) sample
Product examine is surveyed：Preheater apparatus, the μ L of sample introduction 5 record spectrogram.Each component is distinguished according to retention time, is returned with area
One changes method calculates each component content.
The positive effect of the present invention there are provided a kind of simple and effective analysis method, improve analysis efficiency.
Brief description of the drawings
The high-efficient liquid phase chromatogram of Fig. 1 Pyromellitic Acid standard liquids；
The high-efficient liquid phase chromatogram of Fig. 2 1,2,4,5- cyclohexanetetracarboxylic acid standard liquids；
The high-efficient liquid phase chromatogram of Fig. 3 Pyromellitic Acids and 1,2,4,5- cyclohexanetetracarboxylic acid mixed solutions；
The high-efficient liquid phase chromatogram of Fig. 4 hydrogenation reaction solutions 1；
The high-efficient liquid phase chromatogram of Fig. 5 hydrogenation reaction solutions 2.
Specific embodiment
1st, mobile phase and related solution are prepared
1.1 mobile phases are prepared：The 0.49g concentrated sulfuric acids are taken, 1000mL is diluted to ultra-pure water, and adjust molten with ultra-pure water
The pH=3 of liquid, filtering, filtrate is with ultrasonoscope ultrasound 10min.
It is prepared by 1.2 test fluids：
1.2.1 Pyromellitic Acid standard liquid is prepared：10mg Pyromellitic Acids are taken, phased soln and is diluted to flowing
10mL, filtering marks sample 1；
1.2.21,2,4,5- cyclohexanetetracarboxylic acid standard liquid is prepared：Take 10mg1,2,4,5- cyclohexanetetracarboxylic acids, with flowing
Phased soln is simultaneously diluted to 10mL, filtering, marks sample 2；
1.2.3 the preparation of Pyromellitic Acid and 1,2,4,5- cyclohexanetetracarboxylic acid mixed solutions：Take 2mg Pyromellitic Acids
And 8mg1,2,4,5- cyclohexanetetracarboxylic acids, with flowing phased soln and being diluted to 10mL, filter, mark sample 3；
1.2.4 the preparation of the solution of hydrogenation reaction solution 1：10mg hydrogenation reaction solutions are taken, phased soln and is diluted with flowing
To 10mL, filtering, mark sample 4；
1.2.5 the preparation of the solution of hydrogenation reaction solution 2：10mg hydrogenation reaction solutions are taken, phased soln and is diluted with flowing
To 10mL, filtering, mark sample 5.
2nd, sample detection
Agilent1100 high performance liquid chromatographs are opened, the mobile phase of preparation is put into respective channel, by above-mentioned chromatogram
5 samples prepared are positioned over corresponding position to be measured by condition setting instrument parameter, and set sequential parameter,
Detection, records spectrogram.According to Pyromellitic Acid, 1,2,4,5- cyclohexanetetracarboxylic acids and impurity guarantor in the chromatography column
Stay time difference to confirm the corresponding material in each peak in chromatogram, and each component is calculated with area normalization method and contain
Amount.
3rd, testing result
As shown in Figure 1：Pyromellitic Acid (sample 1) retention time is 11.867min, and 8.352min is impurity
Peak；Fig. 2 understands：The retention time of 1,2,4,5- cyclohexanetetracarboxylic acid (sample 2) is 13.474min, 8.449min
It is impurity peaks.To ensure that the condition can isolate Pyromellitic Acid and 1, the absworption peak of 2,4,5- cyclohexanetetracarboxylic acids,
Its mixed liquor is tested, Fig. 3 is seen:12.213min is Pyromellitic Acid, and 13.889min is 1,2,4,5- hexamethylenes
Tetracarboxylic acid.Because instrument error and mobile phase are prepared, each component retention time has deviation.
Sample 4
According to result above；Fig. 4 understands that retention time 12.337min is Pyromellitic Acid, and peak area is 10017.4,
Retention time 14.062min is that 1,2,4,5- cyclohexanetetracarboxylic acid peak areas are 3706.2, impurity peaks retention time
8.879min, peak area is 3529.2.
Pyromellitic Acid content=10017.4 ÷ (10017.4+3706.2+3529.2) × 100%=58.062%
1,2,4,5- cyclohexanetetracarboxylic acids content=3706.2 ÷ (10017.4+3706.2+3529.2) × 100%=21.482%
Impurity content=3529.2 ÷ (10017.4+3706.2+3529.2) × 100%=20.456%
Sample 5
According to result above；Figure understands that retention time 14.032min is 1,2,4,5- cyclohexanetetracarboxylic acids, and peak area is
12414.5, have no the absworption peak of Pyromellitic Acid.Impurity peaks retention time 8.829min, peak area is 2977.1.
1,2,4,5- cyclohexanetetracarboxylic acids content=12414.5 ÷ (12414.5+2977.1) × 100%=80.658%
Impurity content=2977.1 ÷ (12414.5+2977.1) × 100%=19.342%.
By the raw material in invention detection hydrogenation reaction solution, product and impurity, reappearance, sensitivity and the degree of accuracy are equal
Can meet the requirements.
Claims (4)
1. a kind of detection method of Pyromellitic Acid hydrogenation reaction, it is characterised in that：Methods described comprises the following steps：
(1) chromatographic condition：Chromatographic column：Organic acid post；Flow velocity：0.5mL/min；Column temperature：45℃；Sample size：
5μL；Mobile phase：The sulfuric acid solution of 0.005M；Detection time：20min；
(2) sample preparation：1. the preparation of standard liquid：5~10mg of Pyromellitic Acid is taken, with flowing phased soln and dilute
Release in 10mL volumetric flasks, filtering is to be measured；1,2,4,5- 5~10mg of cyclohexanetetracarboxylic acid are taken, mobile phase is used
Dissolve and be diluted in 10mL volumetric flasks, filtering is to be measured；2. prepared by test sample：5~10mg of testing sample is taken,
With flowing phased soln and being diluted in 10mL volumetric flasks, filter, it is to be measured；
(3) sample detection：Preheater apparatus, the μ L of sample introduction 5 record spectrogram；First, Pyromellitic Acid is detected respectively
With 1,2,4,5- cyclohexanetetracarboxylic acid standard liquids determine its retention time respectively；Secondly, testing sample is detected
Liquid；Each component is distinguished according to retention time, each component content is calculated with area normalization method.
2. the detection method of Pyromellitic Acid hydrogenation reaction according to claim 1, it is characterised in that：Used
Organic acid post is HPX-87H organic acid posts, 300mm × 7.8mm, 9 μm.
3. the detection method of Pyromellitic Acid hydrogenation reaction according to claim 1, it is characterised in that：The stream
The pH=2-3 of dynamic phase sulfuric acid solution.
4. the detection method of Pyromellitic Acid hydrogenation reaction according to claim 1, it is characterised in that：Used
Detector is Composition distribution.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103969392A (en) * | 2014-05-21 | 2014-08-06 | 常熟市联邦化工有限公司 | High performance liquid chromatographic analysis method for pyromellitic dianhydride |
| CN104535706A (en) * | 2015-01-04 | 2015-04-22 | 南京化工职业技术学院 | Liquid chromatographic analysis method for industrial pyromellitic acid |
-
2015
- 2015-12-04 CN CN201510885722.4A patent/CN106841409A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103969392A (en) * | 2014-05-21 | 2014-08-06 | 常熟市联邦化工有限公司 | High performance liquid chromatographic analysis method for pyromellitic dianhydride |
| CN104535706A (en) * | 2015-01-04 | 2015-04-22 | 南京化工职业技术学院 | Liquid chromatographic analysis method for industrial pyromellitic acid |
Non-Patent Citations (3)
| Title |
|---|
| K. TANAKA，ET AL: "ION EXCLUSION CHROMATOGRAPHY: LIQUID CHROMATOGRAPHY", 《CHROMATOGRAPHY:LIQUID》 * |
| 杨海燕等: "离子排斥色谱法同时测定生物质液体燃料发酵液中的有机酸、糖、醇", 《化学分析计量》 * |
| 马瑞等: "高效液相色谱法同时测定生物质乳酸发酵液中有机酸及糖类化合物", 《色谱》 * |
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Application publication date: 20170613 |