CN101876640B - Method for measuring content of phenolic hydroxyl groups in polyphenyl ether by titrimetry - Google Patents
Method for measuring content of phenolic hydroxyl groups in polyphenyl ether by titrimetry Download PDFInfo
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- CN101876640B CN101876640B CN 200910237643 CN200910237643A CN101876640B CN 101876640 B CN101876640 B CN 101876640B CN 200910237643 CN200910237643 CN 200910237643 CN 200910237643 A CN200910237643 A CN 200910237643A CN 101876640 B CN101876640 B CN 101876640B
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- phenolic hydroxyl
- polyphenylene oxide
- hydroxyl groups
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- detection method
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 40
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000004448 titration Methods 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 15
- 229920013636 polyphenyl ether polymer Polymers 0.000 title abstract 4
- 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 20
- 239000008367 deionised water Substances 0.000 claims abstract description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 48
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 48
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 31
- 238000003756 stirring Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 229910021641 deionized water Inorganic materials 0.000 claims description 18
- 238000001514 detection method Methods 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical group CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 4
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000001816 cooling Methods 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 abstract 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 abstract 1
- 238000012423 maintenance Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(CC)(c1cc(C)c(*)c(C)c1)Oc1c(C)cc(C(CC)(CC)Oc2c(C)cccc2C)cc1C Chemical compound CCC(CC)(c1cc(C)c(*)c(C)c1)Oc1c(C)cc(C(CC)(CC)Oc2c(C)cccc2C)cc1C 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 aromatic radical acyl chlorides Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Polyethers (AREA)
Abstract
The invention provides a method for measuring content of phenolic hydroxyl groups in polyphenyl ether by titrimetry. The method comprises the following steps: dissolving polyphenyl ether to be measured in an organic solvent, adding a reagent, and heating at 0-60 DEG C for 10-30 minutes; and cooling to room temperature, adding de-ionized water, dropwisely adding several drops of phenolphthalein indicator solution, titrating by using a standard potassium hydroxide water solution until pink stays fadeless for 30 seconds, and calculating the content of phenolic hydroxyl groups in polyphenyl ether according to the blank experiment. The method has the advantages of simple experimental apparatus and high measuring accuracy.
Description
Technical field
The present invention relates to a kind of detection method, specifically, relate to the detection method of content of phenolic hydroxyl groups in a kind of titration measuring polyphenylene oxide.
Background technology
The content of phenolic hydroxyl group is one of important indicator that characterizes its performance in the polyphenylene oxide, and its content of phenolic hydroxyl groups is different and different with polyphenylene oxide molecular weight and chemical composition.
Because the water insoluble and alcohols of polyphenylene oxide be difficult to directly adopt conventional acid base titration to carry out titration, and the titration process operating process is loaded down with trivial details.
Content of phenolic hydroxyl groups carries out accurate method for measuring in a kind of energy of needs research polyphenylene ether.
Summary of the invention
The purpose of this invention is to provide the detection method of content of phenolic hydroxyl groups in a kind of titration measuring polyphenylene oxide, this method is simple to operate, the measuring accuracy height.
In order to realize the object of the invention, the detection method of content of phenolic hydroxyl groups in a kind of titration measuring polyphenylene oxide of the present invention, this method may further comprise the steps:
1) at first the polyphenylene oxide resin sample is dissolved in the organic solvent, adds reaction reagent then, in 0～60 ℃ of heating 10～300min; Add deionized water behind the cool to room temperature, splash into instructions phenolphthalein solution number droplet under the stirring, utilize the aqueous solution of potassium hydroxide (KOH) to carry out titration, keeping 30s colour-fast to pink is terminal point;
2) carry out blank test according to step 1);
3) calculate the content of phenolic hydroxyl group in the polyphenylene oxide then according to following formula:
In the formula:
W phenolic hydroxyl group value, mgKOH/g;
The consumption of KOH standard titration solution during the titration of V sample, mL;
V
0The consumption of KOH standard titration solution during blank titration, mL;
The concentration of c KOH standard titration solution, mol/L;
56.10KOH molecular weight, g/mol;
The quality of m polyphenylene oxide sample, g.
Wherein, the number-average molecular weight of described polyphenylene oxide is 200～40,000, is preferably 200～20,000.
Described heating condition is with 50～60 ℃, and heat time heating time, 10～30min was good.
Described organic solvent such as chloroform, methylene chloride, dimethylbenzene, chlorobenzene or toluene etc., but is not limited to above-mentioned solvent for not dissolving each other with water and the organic solvent of solubilized polyphenylene oxide.
Described reaction reagent is alkyl or aromatic radical acyl chlorides, as pivaloyl chloride, chlorobenzoyl chloride, 3, and 4-dichlorobenzoyl chloride, positive caproyl chloride or 4-methoxy benzoyl chloride etc., but be not limited to above-mentioned acyl chlorides kind.
Described titration process carries out under stirring.
The quality amount ratio of described polyphenylene oxide sample and described organic solvent is 1: 100～2: 1.
The amount ratio of described polyphenylene oxide sample and described reaction reagent is 1: 2～300: 1.
The amount ratio of described polyphenylene oxide sample and described deionized water is 1: 500～1: 1.
The 4-methoxy benzoyl chloride is a reaction reagent, and the detection method of content of phenolic hydroxyl groups is to carry out according to following reaction in the titration measuring polyphenylene oxide of the present invention:
The detection method of content of phenolic hydroxyl groups in the titration measuring polyphenylene oxide of the present invention utilizes the potassium hydroxide aqueous solution of standard that the HCl that produces is carried out titration, and used experimental apparatus is simple, and is easy and simple to handle, the measuring accuracy height.
Embodiment
Following examples are used to illustrate the present invention, but are not used for limiting the scope of the invention.
Below be reagent and instrument related among the embodiment:
Reagent:
Pivaloyl chloride, chlorobenzoyl chloride, 3,4-dichlorobenzoyl chloride, positive caproyl chloride or 4-methoxy benzoyl chloride--analyze pure
Chloroform, methylene chloride, toluene, dimethylbenzene or chlorobenzene--analyze pure
Instructions phenolphthalein solution--1g phenolphthalein is dissolved in the 100ml absolute ethyl alcohol.
The potassium hydroxide titrand--with reference to the method for GB/T 601,561.1mgKOH is dissolved in the 20mL deionized water, is diluted with water to 1000mL.
Instrument:
Electronic analytical balance--degree of accuracy 0.1mg
Triangular flask--250mL
Transfer pipet--10mL
Graduated cylinder--50mL
Embodiment 1
For the polyphenylene oxide sample of number-average molecular weight about 12400, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 5.0000g in the 250mL triangular flask with electronic analytical balance, add the 50mL chloroform, stirring and dissolving.
2) add 4-methoxy benzoyl chloride 0.05g, reflux 30min (55 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 10ml deionized water, stir 10min, add 10mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 7.8,8.6 and 5.2mgKOH/g, and its mean value is 7.2mgKOH/g.
Embodiment 2
For the polyphenylene oxide sample of number-average molecular weight about 5200, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 5.0000g in the 250mL triangular flask with electronic analytical balance, add the 50mL chloroform, stirring and dissolving.
2) add 4-methoxy benzoyl chloride 0.05g, reflux 30min (50 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 10ml deionized water, stir 10min, add 10mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 15.4,14.6 and 18.2mgKOH/g, and its mean value is 16.1mgKOH/g.
Embodiment 3
For the polyphenylene oxide sample of number-average molecular weight about 1200, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 5.0000g in the 250mL triangular flask with electronic analytical balance, add the 50mL chloroform, stirring and dissolving.
2) add 4-methoxy benzoyl chloride 0.05g, reflux 30min (60 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 10ml deionized water, stir 10min, add 10mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 29.6,27.5 and 32.1mgKOH/g, and its mean value is 29.7mgKOH/g.
Embodiment 4
For the polyphenylene oxide sample of number-average molecular weight about 18000, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 5.0000g in the 250mL triangular flask with electronic analytical balance, add 100mL dimethylbenzene, stirring and dissolving.
2) add chlorobenzoyl chloride 0.02g, reflux 35min (55 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 20ml deionized water, stir 10min, add 30mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 3.8,3.6 and 3.7mgKOH/g, and its mean value is 3.6mgKOH/g.
Embodiment 5
For the polyphenylene oxide sample of number-average molecular weight about 400, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 1.0000g in the 250mL triangular flask with electronic analytical balance, add the 100mL methylene chloride, stirring and dissolving.
2) add pivaloyl chloride 0.01g, reflux 40min (60 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 10ml deionized water, stir 10min, add 10mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 141.2,142.0 and 141.5mgKOH/g, and its mean value is 141.6mgKOH/g.
Embodiment 6
For the polyphenylene oxide sample of number-average molecular weight about 800, the step that the employing titrimetry is measured its content of phenolic hydroxyl groups is as follows:
1) accurately takes by weighing polyphenylene oxide sample 5.0000g in the 250mL triangular flask with electronic analytical balance, add the 2mL chlorobenzene, stirring and dissolving.
2) add 3,4-dichlorobenzoyl chloride 0.1g, reflux 40min (60 ℃ of temperature), cool to room temperature then.
3) in triangular flask, add the 50ml deionized water, stir 10min, add 50mL deionized water rinsing condenser pipe inwall from the condenser pipe top, remove condenser pipe then.
4) in triangular flask, add 4 of instructions phenolphthalein solutions, under stirring, use the titration of standard K OH aqueous solution, to system pinkiness and the colour-fast terminal point that is of maintenance 30s.
5) repeat preceding four operations that go on foot 2 times.
6) under the situation that does not add the polyphenylene oxide sample, carry out blank test.
7) carry out data processing according to formula-1, the phenolic hydroxyl group value in the calculation sample, three measured values are respectively 71.2,71.6 and 70.8mgKOH/g, and its mean value is 71.2mgKOH/g.
Though above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (12)
1. the detection method of content of phenolic hydroxyl groups in the titration measuring polyphenylene oxide is characterized in that this method may further comprise the steps:
1) at first the polyphenylene oxide resin sample is dissolved in the organic solvent, adds reaction reagent then, described reaction reagent is pivaloyl chloride, chlorobenzoyl chloride, 3, and 4-dichlorobenzoyl chloride, positive caproyl chloride or 4-methoxy benzoyl chloride are in 0～60 ℃ of heating 10～300min; Add deionized water behind the cool to room temperature, splash into instructions phenolphthalein solution number droplet under the stirring, utilize the aqueous solution of potassium hydroxide to carry out titration, keeping 30s colour-fast to pink is terminal point;
2) under the situation that does not add polyphenylene oxide resin, carry out blank test according to step 1);
3) calculate the content of phenolic hydroxyl group in the polyphenylene oxide then according to following formula:
In the formula:
W phenolic hydroxyl group value, _ mgKOH/g;
The consumption of KOH standard titration solution during the titration of V sample, mL;
V
0The consumption of KOH standard titration solution during blank titration, mL;
The concentration of c KOH standard titration solution, mol/L;
56.10 the molecular weight of KOH, g/mol;
The quality of m polyphenylene oxide sample, g.
2. the detection method of content of phenolic hydroxyl groups according to claim 1 is characterized in that, the number-average molecular weight of described polyphenylene oxide is 200～40,000.
3. the detection method of content of phenolic hydroxyl groups according to claim 1 and 2 is characterized in that, described organic solvent is not for dissolving each other with water and the organic solvent of solubilized polyphenylene oxide.
4. the detection method of content of phenolic hydroxyl groups according to claim 3 is characterized in that, described organic solvent is chloroform, methylene chloride, toluene, dimethylbenzene or chlorobenzene.
5. according to the detection method of claim 1,2 or 4 described content of phenolic hydroxyl groups, it is characterized in that described titration process carries out under stirring.
6. the detection method of content of phenolic hydroxyl groups according to claim 3 is characterized in that, described titration process carries out under stirring.
7. according to the detection method of claim 1,2 or 4 described content of phenolic hydroxyl groups, it is characterized in that the mass ratio of described polyphenylene oxide sample and described organic solvent is 1: 100～2: 1.
8. the detection method of content of phenolic hydroxyl groups according to claim 3 is characterized in that, the mass ratio of described polyphenylene oxide sample and described organic solvent is 1: 100～2: 1.
9. according to the detection method of claim 1,2 or 4 described content of phenolic hydroxyl groups, it is characterized in that the mass ratio of described polyphenylene oxide sample and described reaction reagent is 1: 2～300: 1.
10. the detection method of content of phenolic hydroxyl groups according to claim 3 is characterized in that, the mass ratio of described polyphenylene oxide sample and described reaction reagent is 1: 2～300: 1.
11. the detection method according to claim 1,2 or 4 described content of phenolic hydroxyl groups is characterized in that, the mass ratio of described polyphenylene oxide sample and described deionized water is 1: 500～1: 1.
12. the detection method of content of phenolic hydroxyl groups according to claim 3 is characterized in that, the mass ratio of described polyphenylene oxide sample and described deionized water is 1: 500～1: 1.
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| CN102108121A (en) * | 2010-11-05 | 2011-06-29 | 蓝星（北京）特种纤维技术研发中心有限公司 | Nitrogen-containing polyphenyl ether and preparation method thereof |
| CN103592412A (en) * | 2013-11-01 | 2014-02-19 | 惠州市长润发涂料有限公司 | Hydroxyl value detection method |
| CN104007113B (en) * | 2014-06-18 | 2016-06-08 | 泸州品创科技有限公司 | The detection method of grain unstrained spirits acidity |
| CN116223718A (en) * | 2022-12-12 | 2023-06-06 | 中国科学院大连化学物理研究所 | A kind of assay method of polyphenylene ether hydroxyl content |
Citations (2)
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| US4600741A (en) * | 1984-09-27 | 1986-07-15 | General Electric Company | Polyphenylene ether-polyamide blends |
| CN101423658A (en) * | 2008-11-27 | 2009-05-06 | 中国蓝星（集团）股份有限公司 | Polyphenylene oxide resin composition and method for inhibiting discoloration of polyphenylene oxide resin |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600741A (en) * | 1984-09-27 | 1986-07-15 | General Electric Company | Polyphenylene ether-polyamide blends |
| CN101423658A (en) * | 2008-11-27 | 2009-05-06 | 中国蓝星（集团）股份有限公司 | Polyphenylene oxide resin composition and method for inhibiting discoloration of polyphenylene oxide resin |
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| 李胜方 等.聚苯醚的改性及研究进展.《精细石油化工进展》.2002,第3卷(第12期),全文. * |
| 汪传清 等.磺化聚苯醚的制备与表征.《高分子学报》.1995,(第4期),全文. * |
| 王瑞斌.NaOH间接滴定法快速测定高领土中全硫.《中国非金属矿工业导刊》.2009,(第3期),全文. * |
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Granted publication date: 20111123 Termination date: 20181113 |