CN104502520A - Method for determining content of p-toluenesulfonic acid in butyl acrylate reaction kettle - Google Patents
Method for determining content of p-toluenesulfonic acid in butyl acrylate reaction kettle Download PDFInfo
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- CN104502520A CN104502520A CN201410722769.4A CN201410722769A CN104502520A CN 104502520 A CN104502520 A CN 104502520A CN 201410722769 A CN201410722769 A CN 201410722769A CN 104502520 A CN104502520 A CN 104502520A
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- CN
- China
- Prior art keywords
- toluenesulfonic acid
- acrylic acid
- butyl acrylate
- content
- sodium hydroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 title claims abstract description 80
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 105
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 32
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012086 standard solution Substances 0.000 claims abstract description 6
- 238000010812 external standard method Methods 0.000 claims abstract description 3
- 238000003556 assay Methods 0.000 claims description 20
- 238000004448 titration Methods 0.000 claims description 7
- 230000001186 cumulative effect Effects 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000005070 sampling Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses a method for determining content of p-toluenesulfonic acid in a butyl acrylate reaction kettle. The method for determining the content of p-toluenesulfonic acid in the butyl acrylate reaction kettle comprises the following steps: adding absolute alcohol and a phenolphthalein indicator into a triangular flask, titrating to be reddish with a sodium hydroxide solution, accurately weighing a certain quantity of samples into the triangular flask, titrating to be reddish with a sodium hydroxide standard solution, and recording volume consumed at the moment; correcting acrylic acid by virtue of an external standard method by adopting an automatic sampling gas chromatograph, accurately determining mass percentage of acrylic acid in the samples, and carrying out reverse calculation to obtain volume of sodium hydroxide consumed by acrylic acid according to an acrylic acid calculation formula; subtracting to obtain volume of sodium hydroxide consumed by p-toluenesulfonic acid, and obtaining mass percentage of p-toluenesulfonic acid according to a p-toluenesulfonic acid calculation formula. The method disclosed by the invention has the advantages that the content of p-toluenesulfonic acid in the butyl acrylate reaction kettle can be accurately determined, and a great effect on stably controlling the content of a reaction kettle catalyst is realized.
Description
Technical field
The present invention relates to the technical field of the assay method in a kind of Chemical Manufacture, particularly relate to the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor.
Background technology
P-toluenesulfonic acid is an organic acid of not having an oxidisability, white needles or powder crystallization, easy deliquescence, water soluble, alcohol and other polar solvents, as the widespread use in the production of acrylate of a kind of catalyzer, add from reactor, again use again through extraction and recovery again afterwards.
The assay method that p-toluenesulfonic acid is general is titrimetry: namely carry out titration with standard solution of sodium hydroxide, and with phenolphthalein indicator, record consumes NaOH volume number and calculates content.The method be based upon do not have other acidic materials or other amount of acidic substances lower time, the result of mensuration is just comparatively accurate.
Generally, acidic materials in butyl acrylate reactor have acrylic acid and p-toluenesulfonic acid, the addition of p-toluenesulfonic acid is about 1%, 1% ~ 10% is reached in the acrylic acid content change of the different phase reactor of reaction, in order to stability contorting reaction rate, need to carry out tracking and measuring to catalyzer.But acrylic acid content is so high, the result only drawn by titration is inaccurate, impacts production control.
For this reason, we constantly seek a kind of assay method for p-toluenesulfonic acid content in reactor, to reach the object that stability contorting is produced.
Summary of the invention
The object of the invention is the shortcoming in order to overcome above-mentioned prior art, the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor is provided, the middle control material of the assay method precise certain mass of p-toluenesulfonic acid content in this butyl acrylate reactor, the cumulative volume consuming sodium hydroxide solution is obtained by titration, with the content of Propylene By Gas Chromatography acid, using formula inverse show that acrylic acid consumes the volume of sodium hydroxide solution, thus indirectly obtain the volume that p-toluenesulfonic acid consumes NaOH, its content is determined according to the computing formula of p-toluenesulfonic acid.
The technical solution adopted for the present invention to solve the technical problems is: the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor, this assay method is: in triangular flask, add anhydrous alcohol and phenolphthalein indicator, blush is titrated to sodium hydroxide solution, the sample of precise certain mass is in triangular flask, be titrated to blush with standard solution of sodium hydroxide, record the volume number now consumed; Adopt auto injection gas chromatograph, correct acrylic acid through external standard method, acrylic acid mass percent in Accurate Determining sample, go out according to acrylic acid computing formula inverse the NaOH volume number that acrylic acid consumes; Subtract each other the NaOH volume number showing that p-toluenesulfonic acid consumes, draw its mass percent according to p-toluenesulfonic acid computing formula.
Further, be cumulative volume by the NaOH volume number of titration gained, contain acrylic acid and p-toluenesulfonic acid.
Further, acrylic acid measurement result uses auto injection gas chromatograph, draws after external standard corrects.
Further, the NaOH volume number that acrylic acid consumes draws according to formula reverse operation.
Further, the NaOH volume number of p-toluenesulfonic acid consumption indirectly draws by subtracting each other.
This method of testing is in conjunction with gas chromatograph for determination acrylic acid, and in butyl acrylate is produced, generally all need the acrylic acid detecting one of raw material, this assay method has very large practicality.This assay method can also be used in the mensuration of catalyst content in acetate reactor, and also can offer help for the situation the method thinking containing multiple acidic materials, therefore it has applicability more widely.
In sum, in butyl acrylate reactor of the present invention, the assay method of p-toluenesulfonic acid content obtains by titration the cumulative volume consuming sodium hydroxide solution, with the content of Propylene By Gas Chromatography acid, using formula inverse show that acrylic acid consumes the volume of sodium hydroxide solution, thus indirectly obtain the volume that p-toluenesulfonic acid consumes NaOH, determine its content according to the computing formula of p-toluenesulfonic acid.
Embodiment
Embodiment 1
The assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor described by the present embodiment 1, being specially of this assay method: add 50ml anhydrous alcohol and 2-3 drips 0.1g/L phenolphthalein in 250ml triangular flask, blush is titrated to 0.1mol/L standard solution of sodium hydroxide, disregard reading, add sample quality m=2-3g(and claim accurate example weight) in triangular flask, blush is titrated to C=0.1mol/L standard solution of sodium hydroxide, colour-fastly in 30s namely arrive terminal, record consumes NaOH volume number V.
Draw 1ml sample in chromatogram bottle, then be placed into automatic sampler, transfer acrylic acid detection method, determine rear operation, method for the treatment of reads acrylic acid mass percent X1 after running, and goes out the NaOH volume number V1 of acrylic acid consumption according to acrylic acid computing formula inverse.
Draw from V-V1 and draw its mass percent X2 according to p-toluenesulfonic acid computing formula by the NaOH volume number V2 that p-toluenesulfonic acid consumes.
described acrylic acid computing formula is: X1=(V1 × C × 0.07206 × 100)/m; In formula, 0.07206 represents suitable for 1.00mL Standard Volumetric Solutions for Sodium Hydroxide ［ C(NaOH)=1.000mol/L ］ gram acrylic acid quality represented.
Described p-toluenesulfonic acid computing formula is: X2=(V2 × C × 0.1902 × 100)/m; In formula, 0.1902 represents suitable for 1.00mL Standard Volumetric Solutions for Sodium Hydroxide ［ C(NaOH)=1.000mol/L ］ a gram quality for the p-toluenesulfonic acid represented.
Described acrylic acid detection method condition is: injector temperature 250 DEG C, split ratio 5:1; Chromatographic column J & W 125-3212:250 DEG C: 15m × 530 μm × 1 μm, flow velocity 5ml/min; Initial 50 DEG C of post case keeps 5min, is raised to 200 DEG C keeps 25min with the heating rate of 18 DEG C/min; Detector temperature 250 DEG C, hydrogen flowing quantity 30ml/min, air mass flow 300ml/min; Sample size is 1 μ L.
The above is only preferred embodiment of the present invention, not does any pro forma restriction to technical scheme of the present invention.Every above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all still belong in the scope of technical scheme of the present invention.
Claims (5)
1. the assay method of p-toluenesulfonic acid content in a butyl acrylate reactor, it is characterized in that, this assay method is: in triangular flask, add anhydrous alcohol and phenolphthalein indicator, blush is titrated to sodium hydroxide solution, the sample of precise certain mass is in triangular flask, be titrated to blush with standard solution of sodium hydroxide, record the volume number now consumed; Adopt auto injection gas chromatograph, correct acrylic acid through external standard method, acrylic acid mass percent in Accurate Determining sample, go out according to acrylic acid computing formula inverse the NaOH volume number that acrylic acid consumes; Subtract each other the NaOH volume number showing that p-toluenesulfonic acid consumes, draw its mass percent according to p-toluenesulfonic acid computing formula.
2. the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor according to claim 1, is characterized in that, be cumulative volume, contain acrylic acid and p-toluenesulfonic acid by the NaOH volume number of titration gained.
3. the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor according to claim 1, it is characterized in that, acrylic acid measurement result uses auto injection gas chromatograph, draws after external standard corrects.
4. the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor according to claim 1 or 3, it is characterized in that, the NaOH volume number that acrylic acid consumes draws according to formula reverse operation.
5. the assay method of p-toluenesulfonic acid content in a kind of butyl acrylate reactor according to claim 1 or 2, it is characterized in that, the NaOH volume number of p-toluenesulfonic acid consumption indirectly draws by subtracting each other.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410722769.4A CN104502520B (en) | 2014-12-03 | 2014-12-03 | The assay method of p-methyl benzenesulfonic acid content in a kind of butyl acrylate reactor |
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| CN201410722769.4A CN104502520B (en) | 2014-12-03 | 2014-12-03 | The assay method of p-methyl benzenesulfonic acid content in a kind of butyl acrylate reactor |
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| CN104502520A true CN104502520A (en) | 2015-04-08 |
| CN104502520B CN104502520B (en) | 2016-06-22 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106248845A (en) * | 2015-06-10 | 2016-12-21 | 中国石油天然气股份有限公司 | Method for measuring content of unsaturated aldehyde in liquid phase mixture |
| CN106248807A (en) * | 2015-06-10 | 2016-12-21 | 中国石油天然气股份有限公司 | Method for analyzing acetic acid content in propylene oxidation reaction liquid-phase product |
| CN107561169A (en) * | 2016-07-01 | 2018-01-09 | 彤程化学（中国）有限公司 | The resolution and quantitative analysis method of p-methyl benzenesulfonic acid triethanolamine salt in phenolic resin |
| CN110596303A (en) * | 2018-06-13 | 2019-12-20 | 中冶建筑研究总院有限公司 | Method for detecting content of sulfydryl |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106248845B (en) * | 2015-06-10 | 2018-05-04 | 中国石油天然气股份有限公司 | Method for measuring content of unsaturated aldehyde in liquid phase mixture |
| CN106248807B (en) * | 2015-06-10 | 2019-03-12 | 中国石油天然气股份有限公司 | Method for analyzing acetic acid content in propylene oxidation reaction liquid-phase product |
| CN107561169A (en) * | 2016-07-01 | 2018-01-09 | 彤程化学（中国）有限公司 | The resolution and quantitative analysis method of p-methyl benzenesulfonic acid triethanolamine salt in phenolic resin |
| CN110596303A (en) * | 2018-06-13 | 2019-12-20 | 中冶建筑研究总院有限公司 | Method for detecting content of sulfydryl |
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| CN104502520B (en) | 2016-06-22 |
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