CS256487B1 - Method of by-products and phenol in diane parallel quantitative determination - Google Patents
Method of by-products and phenol in diane parallel quantitative determination Download PDFInfo
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- CS256487B1 CS256487B1 CS86528A CS52886A CS256487B1 CS 256487 B1 CS256487 B1 CS 256487B1 CS 86528 A CS86528 A CS 86528A CS 52886 A CS52886 A CS 52886A CS 256487 B1 CS256487 B1 CS 256487B1
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- phenol
- products
- quantitative determination
- diane
- analysis
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000006227 byproduct Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 10
- RWYFURDDADFSHT-RBBHPAOJSA-N diane Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1=C(Cl)C2=CC(=O)[C@@H]3CC3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RWYFURDDADFSHT-RBBHPAOJSA-N 0.000 title description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004817 gas chromatography Methods 0.000 claims description 5
- 230000005526 G1 to G0 transition Effects 0.000 claims description 4
- 239000010695 polyglycol Substances 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 229920002545 silicone oil Polymers 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims 1
- 238000004458 analytical method Methods 0.000 abstract description 7
- CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 abstract description 2
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 abstract description 2
- 229920000515 polycarbonate Polymers 0.000 abstract description 2
- 239000004417 polycarbonate Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 2
- 238000003556 assay Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 238000001303 quality assessment method Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- MLCQXUZZAXKTSG-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 MLCQXUZZAXKTSG-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- -1 p-hydroxyphenyl Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Řešení se týká metody pro souběžné kvantitativní stanovení vedlejších produktů a fenolu v dianu kapilární plynovou chromátografií s dávkováním přímo na kolonu. Analýza nevyžaduje přípravu derivátů ani nezávislé provedení stanovení^ fenolu a je provedena s vysokou separační účinností. K analýze se s výhodou použije kolona z velmi čistého kysličníku křemičitého, smočená fenylmethylsilikonovým olejem. Délka analýzy je 25 minut. Metoda je vhodná k hodnocení kvality dianu pro epoxydové pryskyřice i polykarbonáty.The solution relates to a method for concurrent quantitative determination of by-products and phenol in capillary gas dian by chromatography directly on column. The analysis does not require the preparation of derivatives nor independent performance of the assay phenol and is made with high separation efficiency. The analysis is preferably carried out very pure silica column wetted with phenylmethylsilicone oil. Analysis time is 25 minutes. The method is suitable for dian quality assessment for epoxy resins and polycarbonates.
Description
Vynález ee týká kvantitativního stanovení vedlejších produktů a fenolu v dianu metodou plynové chromatografie.The invention relates to the quantitative determination of by-products and phenol in diene by a gas chromatography method.
2,2-bis-(4-hydroxyfenyl)-propan zvaný dian nebo Bisfenol A se používá především k výrobě nátěrových hmot a pryskyřic na bázi polykarbonátů. Vyrábí se kysele katalyzovanou kondenzaci fenolu a acetonu. Kromě požadovaného produktu, p,pdianu, vznikají některá vedlejší látky, zejména 4-»methyl4-(p-hydroxyfenyl)-pentanon-2, 2,2-(2-hydroxyfenyl)-propan zvaný οτθ-dian, 2-(4-hydroxyfenyl)-2-(2-hydroxyfenyl)-propan zvaný o.pÁdian, 4-(4-hydroxyfenyl)-2,2,4-trimethylchroman zvaný kodimer, l,l,3-trimethyl-3-(4-hydroxyfenyl)-indanol-5,2,2-bis- (4-hydroxyphenyl) -propane called dian or Bisphenol A is mainly used for the production of paints and resins based on polycarbonates. Acid catalyzed condensation of phenol and acetone is produced. In addition to the desired product, β, β-dian, some by-products are formed, in particular 4-methyl-4- (p-hydroxyphenyl) -pentanone-2,2,2- (2-hydroxyphenyl) -propane called οτθ-dian, 2- (4- hydroxyphenyl) -2- (2-hydroxyphenyl) -propane called oadian, 4- (4-hydroxyphenyl) -2,2,4-trimethylchroman called codimer, 1,1,3-trimethyl-3- (4-hydroxyphenyl) -indanol-5,
2,4-bis-(4-hydroxykumyl)-fenol zvaný BPX, případně další látky, např. p-izopropenylfenol, 2-hydroxy-2,4,4-trimethylfiavan, 4-methyl-2,4-bis-(4-hydroxyfenyl)-penten-l a 6,6-dihydroxy3,3,3* 3-tetramethyl-1,1-spirobilndan, 2 hlediska dalšího zpracováni je obsah vedlejších produktů a zbytkového fenolu nežádoucí, proto se analyticky sleduje.2,4-bis- (4-hydroxycoumyl) -phenol called BPX, optionally other substances such as p-isopropenylphenol, 2-hydroxy-2,4,4-trimethylphavanate, 4-methyl-2,4-bis- (4 In terms of further processing, the content of by-products and residual phenol is undesirable and is therefore monitored analytically.
Původně byly vedlejší produkty v dianu analyzovány semikvantitativně papírovou nebo tenkovrstvou chromatografií, později byly publikovány metody využívající plynové nebo kapalinové chromatografie. Fenyl byl stanovován plynovou chromatograf ii bu3 separátní metodou, nebo spolu s dihydroxyderiváty. Přímému stanovení plynovou chromatografií bylo možno z vedlejších produktů podrobit pouze dihydroxyderiváty, proto se později přistoupilo k derivatizaci dianu. Vzorky byly převáděny na acatáty nebo trlmethylsilylethery některým ze silylačnich činidel, např. N,O-bis-(trimethylsilyl)-trifluoreacetamidem, derivó/ty byly po odpařeni v injektorů separoványInitially, by-products in the diane were analyzed semi-quantitatively by paper or thin-layer chromatography, later methods using gas or liquid chromatography were published. Phenyl was determined by gas chromatography either by a separate method or together with dihydroxy derivatives. Only dihydroxy derivatives could be subjected to the direct gas chromatographic determination, so the dianne was later derivatized. The samples were converted to acatates or trlmethylsilyl ethers by some of the silylating agents, eg N, O-bis- (trimethylsilyl) -trifluoroeacetamide, the derivatives were separated after evaporation in injectors separated
256 487 na náplňové koloně a detekovány plamenoionizačním detektorem· Tímto způsobem bylo možno stanovit všechny vedlejší produkty, ale nikoliv fenol·256 487 on packed column and detected by flame ionisation detector · In this way all by-products but not phenol could be determined ·
Nyní byl nalezen způeob souběžného kvantitativního stanoveni vedlejšioh produktů a fenolu v dianu metodou plynové chromatografie, který je předmětem tohoto vynálezu a jehož podstata spočívá v tom, žs se roztok dianu v etanolu dávkuje na začátek skleněné nebo křemenné kapilární kolony, smočené stacionární fází typu silikonového oleje nebo polyglykolu při teplotě 40 ÚC až teploty varu rozpouštědla metodou přímého dávkování na kolonu·We have now found a method for the simultaneous quantitative determination of byproducts and phenol in diane by the gas chromatography method of the present invention, which is to dispense a solution of diane in ethanol at the beginning of a glass or silica capillary column wetted with a stationary phase of silicone oil type. or polyglycol at a temperature of 40 U C to solvent boiling point by direct dispensing onto the column ·
Roztok dianu bez předchozí derivatizace se vnáší injekční stříkačkou na začátek kapilární kolony a chromatografuje ae při programované teplotě kolony, detekuje plamenoionizačním detektorem a složky se stanoví po korekci odezev detektoru kalibračními faktory, zjištěnými analýzou směsi známého složeni. Pro smočeni kapilární kolony se použije stacionární fáze typu silikonového oleje nebo polyglykolu, které jsou vázány na vnitřní povrch kolony fyzikálně nebo chemicky, případně jsou zesilovány chemickou vazbou·The dianne solution without prior derivatization is injected into the top of the capillary column via a syringe and chromatographed at programmed column temperature, detected by a flame ionization detector, and the components determined after correcting the detector responses by calibration factors determined by analysis of a mixture of known composition. For wetting of the capillary column, a stationary phase of silicone oil or polyglycol type is used, which are bound physically or chemically to the inner surface of the column or they are reinforced by chemical bonding ·
Způsob souběžného stanoveni vedlejších produktů a fenolu v dianu podle vynálezu představuje úsporu eilylačniho činidla, používaného k derivatizacl dianu a času, který příprava derivátů dianu vyžaduje· Úsporu představuje rovněž čas, nutný pro prováděni separátního stanoveni fenolu· Další výhodou 0O8tupu podle vynálezu je skutečnost, že se pracuje na kapilární koloně, která vykazuje vysokou účinnost a etanovavané látky jeou dobře eeparovatelné,The simultaneous determination of byproducts and phenol in the diane according to the invention represents the saving of the eilylating agent used for the derivatization of dian and the time required for the preparation of the diane derivatives. working on a capillary column, which shows high efficiency and ethanated substances are well eeparable,
Způeob analýzy dle vynálezu ilustruje níže uvedený přiklad:The analysis example according to the invention is illustrated by the following example:
Přiklad 1Example 1
Roztok dianu v etanolu ee dávkuje injekční stříkačkou typu Hamilton na začátek křemenná kapilární kolony udržovaná na teplotě 40 až 78 °C· Použije se kapilární kolona z velmi čistéhoDiane solution in ethanol ee is dosed with a Hamilton syringe to the top of the silica capillary column maintained at 40-78 ° C. · Use a very pure capillary column.
- 3 256 487 kysličníku křemičitého o délce 25 m a vnitřním průměru 0,32 mm pokrytá stacionární fázi, např, fenylmethylsilikonovým olejem. Kolona je umístěna v termostatu plynového chromatografu, vybaveného dávkovacim zařízením,např, plameno ionizačním detektorem a vyhodnocovacím zařízením. Termostat chromatografu se rychle ohřeje na počáteční pracovní teplotu 210 °C a pak jeho teplota stoupá 6 minut rychlostí 5 °C/min a dále rychlostí 10 °C/min do 300 °C, Nosný plyn helium protéká rychlosti 3 ml/min. Analýza je během 25 minut ukončena. Odezvy jednotlivých složek se korigují faktory., které byly získány vyhodnocením analýzy roztoku kalibrační směsi navážené z čistých standardů, Z korigovaných hodnot odezev se vypočte složeni analyzovaného dianu metodou vnitřní normalizace·- 3 256 487 silicon dioxide with a length of 25 m and an internal diameter of 0,32 mm covered with a stationary phase, eg phenylmethylsilicone oil. The column is placed in a gas chromatograph thermostat equipped with a metering device, eg a flame ionization detector and an evaluation device. The thermostat of the chromatograph is rapidly heated to an initial operating temperature of 210 ° C and then rises for 6 minutes at a rate of 5 ° C / min and at a rate of 10 ° C / min to 300 ° C. The helium carrier gas flows at 3 ml / min. The analysis is complete within 25 minutes. The responses of the individual components are corrected by the factors obtained by evaluating the analysis of the calibration mixture solution weighed from pure standards. From the corrected response values, the composition of the analyzed Diana is calculated by the internal normalization method.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS86528A CS256487B1 (en) | 1986-01-24 | 1986-01-24 | Method of by-products and phenol in diane parallel quantitative determination |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS86528A CS256487B1 (en) | 1986-01-24 | 1986-01-24 | Method of by-products and phenol in diane parallel quantitative determination |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS52886A1 CS52886A1 (en) | 1987-09-17 |
| CS256487B1 true CS256487B1 (en) | 1988-04-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS86528A CS256487B1 (en) | 1986-01-24 | 1986-01-24 | Method of by-products and phenol in diane parallel quantitative determination |
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| Country | Link |
|---|---|
| CS (1) | CS256487B1 (en) |
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1986
- 1986-01-24 CS CS86528A patent/CS256487B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS52886A1 (en) | 1987-09-17 |
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