CN101650304A - Method for determining content of sodium p-toluenesulfinate in reduction process of p-toluenesulfonyl chloride - Google Patents
Method for determining content of sodium p-toluenesulfinate in reduction process of p-toluenesulfonyl chloride Download PDFInfo
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- CN101650304A CN101650304A CN200910100908A CN200910100908A CN101650304A CN 101650304 A CN101650304 A CN 101650304A CN 200910100908 A CN200910100908 A CN 200910100908A CN 200910100908 A CN200910100908 A CN 200910100908A CN 101650304 A CN101650304 A CN 101650304A
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- spts
- sodium
- toluenesulfinate
- wavelength
- acid sodium
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- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 21
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000011946 reduction process Methods 0.000 title abstract 2
- 238000001514 detection method Methods 0.000 claims abstract description 6
- 239000012086 standard solution Substances 0.000 abstract description 13
- 239000000243 solution Substances 0.000 abstract description 6
- 238000002211 ultraviolet spectrum Methods 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 2
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 abstract 3
- -1 paratoluenesulfonic acid sodium salt Chemical class 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 14
- CUYTYLVEYFUAAX-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sodium Chemical compound [Na].CC1=CC=C(S(O)(=O)=O)C=C1 CUYTYLVEYFUAAX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 4
- 238000013459 approach Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VLUWLNIMIAFOSY-UHFFFAOYSA-N 2-methylbenzenesulfinic acid Chemical compound CC1=CC=CC=C1S(O)=O VLUWLNIMIAFOSY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
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- Investigating Or Analysing Materials By Optical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention relates to a method for determining the content of sodium p-toluenesulfinate in a reduction process of p-toluenesulfonyl chloride. A wavelength of 282 nm, which does not absorb sodium 4-toluenesulfonate and absorbs a great amount of sodium p-toluenesulfinate, is obtained by respectively scanning ultraviolet-spectrum full wavelengths of standard solutions of the sodium 4-toluenesulfonate and the sodium p-toluenesulfinate, not only can favorably determine the content of the sodium p-toluenesulfinate, but also can satisfy the needs on detection sensitivity. Under the wavelength, the method not only can differentiate the sodium 4-toluenesulfonate from the sodium p-toluenesulfinate which are contained in the solution, but also can simultaneously achieve the quantitative determination of the sodium p-toluenesulfinate.
Description
Technical field
The present invention relates to a kind of quantivative approach of SPTS, relate in particular to a kind of in the paratoluensulfonyl chloride reducing process, by the uv-spectrophotometric method SPTS and the paratoluenesulfonic acid sodium salt that are contained are distinguished, and SPTS is carried out quantitative methods.
Background technology
SPTS is the product that paratoluensulfonyl chloride obtains through reduction, reduces in sodium sulfite aqueous solution and obtains through paratoluensulfonyl chloride.Because this step reaction in aqueous solution is to be accompanied by the paratoluensulfonyl chloride hydrolysis to generate accessory substance---paratoluenesulfonic acid sodium salt, how to monitor hydrolysis reaction in process of production and is very important.But because two kinds of materials are very approaching on the liquid chromatography appearance time, can not obtain the content of SPTS simply by instrumental analysis, so can't find suitable liquid phase chromatogram condition to be applicable to separating of SPTS and paratoluenesulfonic acid sodium salt.Traditional method is by SPTS and methylating reagent, as: dimethyl suflfate, the reaction back generates first sulfone toluene, calculates the content of SPTS indirectly by analyzing first sulfone content of toluene.This analytical approach because the conversion ratio of methylation reaction can not reach 100%, thereby is brought very big error to testing result.If can't analyze accurately, also just be difficult to improve or optimize the technology of paratoluensulfonyl chloride reduction reaction to SPTS.At present, go back the neither one method and can solve the method for measuring SPTS in paratoluenesulfonic acid sodium salt and the SPTS potpourri.
Summary of the invention
The purpose of this invention is to provide a kind of method of measuring SPTS content in the paratoluensulfonyl chloride reducing process.Seek the difference of toluenesulfinic acid sodium and two kinds of compound absorbing wavelength of paratoluenesulfonic acid sodium salt by the uv-spectrophotometric method, and then the SPTS and the paratoluenesulfonic acid sodium salt that are contained distinguished, and further SPTS is carried out quantitatively.
Paratoluenesulfonic acid sodium salt and SPTS standard items are made into certain density solution respectively, obtain the spectrogram of two different materials then respectively through the ultraviolet spectrum full wavelength scanner.In two different ultraviolet spectrum curves, find out the maximum disparity of the absorption peak of paratoluenesulfonic acid sodium salt or SPTS respectively, or find out paratoluenesulfonic acid sodium salt and be absorbed as zero and SPTS has the strong wavelength that absorbs.The ultraviolet spectral analysis of paratoluenesulfonic acid sodium salt and SPTS finds that their ultraviolet absorption curve is very similar, two only poor 2nm of material maximum absorption band wavelength, paratoluenesulfonic acid sodium salt 260nm and SPTS 262nm, therefore can't analyze these two materials at the maximum absorption band place, be absorbed as zero wavelength 282nm place at paratoluenesulfonic acid sodium salt and find that SPTS has a bigger absorption value, be approximately 75% of maximum absorption peak.SPTS being made into different concentration determination transmittance T% then under this wavelength, is that horizontal ordinate is an ordinate with the different transmittance T% that record by the SPTS of variable concentrations, draws the working curve of SPTS.
The method of SPTS content is measured SPTS in the mensuration paratoluensulfonyl chloride reducing process of the present invention under wavelength 282nm.
The wavelength bandwidth of described detection method is set at 2nm, and the temperature during mensuration is 20 ± 2 ℃.
The beneficial effect that the present invention realizes:
The present invention carries out the ultraviolet spectrum full wavelength scanner respectively by paratoluenesulfonic acid sodium salt and SPTS standard solution, obtain a paratoluenesulfonic acid sodium salt and be absorbed as wavelength---282nm zero and that the SPTS absorption is bigger, this wavelength can be measured the p-toluenesulfonic acid sodium content preferably, can also satisfy the needs to detection sensitivity.Under wavelength, the SPTS and the paratoluenesulfonic acid sodium salt that are contained in the solution can not only be distinguished, and can realize the SPTS detection by quantitative simultaneously.
Description of drawings
Fig. 1 be SPTS and paratoluenesulfonic acid sodium salt ultraviolet full wavelength scanner curve ratio, be paratoluenesulfonic acid sodium salt wherein at the wavelength 260nm place higher curve of absorption peak, lower is SPTS, corresponding number in the figure is followed successively by 11 and 12;
Fig. 2 is the ultraviolet full wavelength scanner curve of SPTS under the variable concentrations, wherein the pairing from high to low SPTS concentration of the absorption peak in the 250-300nm wavelength coverage is respectively: 0.002mol/L, 0.0015mol/L, 0.00125mol/L, 0.001mol/L and 0.0005mol/L, and corresponding number in the figure is followed successively by 21,22,23,24 and 25;
Fig. 3 is the uv-spectrogram full wavelength scanner curve of paratoluenesulfonic acid sodium salt under the variable concentrations, wherein be respectively at the pairing from high to low p-toluenesulfonic acid na concn of the absorption peak at 260nm wavelength place: 0.01mol/L, 0.005mol/L, 0.001mol/L and 0.0005mol/L, corresponding number in the figure is followed successively by 31,32,33 and 34;
Fig. 4 is a SPTS working curve under the 282nm for wavelength.
Embodiment
Below describe technical scheme of the present invention in detail.Only for the explanation concrete grammar, its scale of this method is not subjected to the restriction of embodiment to the embodiment of the invention.
Embodiment 1
The preparation of paratoluenesulfonic acid sodium salt and SPTS standard solution
The preparation of p-toluenesulfonic acid sodium standard solution
Accurately take by weighing 0.3884g (0.002mol) paratoluenesulfonic acid sodium salt,, be made into the p-toluenesulfonic acid sodium standard solution of 0.02mol/l with careful the immigration in the 100ml volumetric flask behind an amount of dissolved in distilled water.Get above-mentioned 0.02mol/l p-toluenesulfonic acid sodium standard solution 50ml more respectively, 25ml, 10ml in 5ml to the 100ml volumetric flask, is made into the p-toluenesulfonic acid sodium standard solution of 0.01mol/, 0.005mol/l, 0.002mol/l, 0.001mol/l.
The preparation of SPTS standard solution
Accurately take by weighing the SPTS after 0.1782g (0.001mol) makes with extra care,, be made into the SPTS standard solution of 0.01mol/l with moving in the 100ml volumetric flask behind an amount of dissolved in distilled water.
Determining of SPTS solution absorbing wavelength
Get 0.01mol/l among the embodiment 1 respectively, 0.005mol/l, 0.002mol/l, 0.001mol/l the p-toluenesulfonic acid sodium standard solution and the SPTS standard solution of 0.01mol/l, with distilled water is blank sample, carry out the ultraviolet full wavelength scanner with UV2500 type ultraviolet spectrophotometer under 200-400nm, the gained collection of illustrative plates as shown in Figure 1.As seen from the figure, the maximum absorption wavelength difference of paratoluenesulfonic acid sodium salt and two kinds of materials of SPTS is little, so maximum absorption wavelength can not be used to analyze the content of these two kinds of materials.As Fig. 2, shown in 3, paratoluenesulfonic acid sodium salt does not have absorption at 282nm wavelength place, and SPTS still has absorption more by force, is SPTS optimum determining wavelength so select 282nm.
The drafting of SPTS solution typical curve
Ultraviolet spectrophotometric determination condition is: wavelength is fixed as λ=282nm; Bandwidth=2nm; Integral time=10s; 20 ± 2 ℃ of temperature during mensuration; Used glass apparatus is all through overcorrect.
Accurately draw embodiment 1 SPTS solution standard solution 20ml, 15ml, 12.5ml, 10ml and 5ml are in the 100ml volumetric flask, with distilled water diluting to scale, getting concentration is 0.002mol/l, 0.0015mol/l, 0.00125mol/l, 0.001mol/l and the standard solution of 0.0005mol/l, under UV2500 type ultraviolet spectrophotometer 282nm wavelength, use the 1cm cuvette, make reference liquid with distilled water, read absorbance drawing standard curve (see figure 4), regression equation is y=0.01688+392.83612 * X, corresponding coefficient R=0.99865, the experimental data degree of accuracy is better.
The precision test is got same sample and is carried out 5 replicate determinations, the results are shown in Table 1.
The test of table 1 precision
Can find out that from table 1 relative standard deviation＜0.76% shows that the precision of this detection method under wavelength 282nm is fine.
Recovery test is measured 3 times altogether according to standard curve determination 0.0005,0.0010 and 0.0015 3 s' the recovery, the results are shown in Table 2.
Table 2 recovery test
As can be seen from Table 2, the average recovery rate of three groups of data approaches 100%, shows that the accuracy of this experiment is very high.
Claims (3)
1. a method of measuring SPTS content in the paratoluensulfonyl chloride reducing process is characterized in that in wavelength 282nm place detection SPTS.
2. the method for SPTS content in the mensuration paratoluensulfonyl chloride reducing process according to claim 1, the bandwidth settings that it is characterized in that detecting wavelength is 2nm.
3. the method for SPTS content in the mensuration paratoluensulfonyl chloride reducing process according to claim 1 is characterized in that detected temperatures is 20 ± 2 ℃.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910100908A CN101650304A (en) | 2009-08-06 | 2009-08-06 | Method for determining content of sodium p-toluenesulfinate in reduction process of p-toluenesulfonyl chloride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910100908A CN101650304A (en) | 2009-08-06 | 2009-08-06 | Method for determining content of sodium p-toluenesulfinate in reduction process of p-toluenesulfonyl chloride |
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| CN101650304A true CN101650304A (en) | 2010-02-17 |
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| CN200910100908A Pending CN101650304A (en) | 2009-08-06 | 2009-08-06 | Method for determining content of sodium p-toluenesulfinate in reduction process of p-toluenesulfonyl chloride |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105699308A (en) * | 2014-11-26 | 2016-06-22 | 天津市科密欧化学试剂有限公司 | Ion pair reagent quality control method |
| CN114295571A (en) * | 2021-12-29 | 2022-04-08 | 天和药业股份有限公司 | Rapid tracking detection method for aminomethylbenzoic acid hydrogenation reaction process |
-
2009
- 2009-08-06 CN CN200910100908A patent/CN101650304A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105699308A (en) * | 2014-11-26 | 2016-06-22 | 天津市科密欧化学试剂有限公司 | Ion pair reagent quality control method |
| CN114295571A (en) * | 2021-12-29 | 2022-04-08 | 天和药业股份有限公司 | Rapid tracking detection method for aminomethylbenzoic acid hydrogenation reaction process |
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Open date: 20100217 |