JP2011080766A - 燃料油の分析方法。 - Google Patents
燃料油の分析方法。 Download PDFInfo
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- 239000000295 fuel oil Substances 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 28
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000002897 diene group Chemical group 0.000 claims abstract 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 32
- 238000011088 calibration curve Methods 0.000 claims description 27
- 238000004458 analytical method Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000002210 silicon-based material Substances 0.000 claims description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 abstract description 7
- 238000001228 spectrum Methods 0.000 abstract description 4
- 150000001993 dienes Chemical class 0.000 description 55
- 238000005259 measurement Methods 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003502 gasoline Substances 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 239000000446 fuel Substances 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003209 petroleum derivative Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- XRYKNRLGZZNWEE-UHFFFAOYSA-N 4-methyl-1,2,4-triazole-3,5-dione Chemical compound CN1C(=O)N=NC1=O XRYKNRLGZZNWEE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- -1 2-butanone Chemical class 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
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Abstract
【解決手段】燃料油の1H−NMRスペクトルを測定する工程と、上記1H−NMRスペクトルにおける、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計に基づいて、上記燃料油における共役ジエン構造の含有割合を求める工程と、を有する、燃料油の分析方法。
【選択図】なし
Description
測定試料として、UOP法326−82により求められたジエン価が下記表1のとおりであるガソリン(測定試料1)を準備した。直径5mmのNMR試料管に、測定試料1を39.4mgを入れ、次いで、マイクロピペットを用いてCDCl3(テトラメチルシラン0.03%含有、Aldrich社製)800μLと、メタノール(和光純薬工業(株)社製、特級)2μL(4.94×10−2mmol)を加えた。当該NMR試料管をテトラフルオロエチレン製のキャップで封止し、後述のNMR測定装置及び測定条件により、1H−NMRスペクトルを測定した。得られた1H−NMRスペクトルから、メタノールのメチル基の水素原子由来のピークβ(ケミカルシフト:3.4〜3.5ppm)の積分値Bに対する、テトラメチルシランを基準としてケミカルシフト6.1〜6.6ppmに観測される全ピークαの積分値の合計Aの比A/Bを求めた。
NMR測定装置は、Varian社製NMR System500を用いた。
NMR測定は、絶対値モードで以下の条件で行った。
待ち時間(Relaxation Delay):2秒間
積算回数(Number of Scans):32回
検出感度(Receiver Gain):24
測定試料として下記表1に示す各測定試料を用いた以外は、実施例1と同様にして、メタノールのメチル基の水素原子由来のピークβの積分値Bに対する、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計Aの比A/Bを求めた。
測定試料1に代えて、共役ジエン構造を含有するガソリン(測定試料12)38.4mgを用いた以外は、実施例1と同様にして、メタノールのメチル基の水素原子由来のピークβの積分値Bに対する、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計Aの比A/Bを求めた。得られた比A/Bと、上記実施例1〜11で得られた検量線とから、ジエン価を算出したところ、1.9であり、測定試料12についてUOP法326−82によりジエン価を測定した結果(1.7g/100g)と良い一致を示した。
比較例1〜11では、実施例1〜11における比A/Bの代わりに、メタノールのメチル基の水素原子由来のピークβの積分値Bに対する、テトラメチルシランを基準として4.5〜6.0ppmに観測される全ピークα’’の積分値の合計A’’の比A’’/Bをそれぞれ求めた。次いで、比較例1〜11で得られた比A’’/Bを測定試料100mgあたりに換算した値(比A’’/Bを測定試料の使用量(mg)で除して100を乗じた値)を横軸にとり、UOP法326−82により求められたジエン価(g/100g)を縦軸にとり、検量線を作成した。得られた検量線は、下記式(4)に示すとおりであった。図5は、比較例1〜11で得られた検量線を示す図である。なお、図5中、Rは相関係数を示す。
Claims (4)
- 燃料油の1H−NMRスペクトルを測定する工程と、
前記1H−NMRスペクトルにおける、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計Aに基づいて、前記燃料油における共役ジエン構造の含有割合を求める工程と、を有する、燃料油の分析方法。 - 燃料油と標準物質とを含有する試料の1H−NMRスペクトルを測定する工程と、
前記1H−NMRスペクトルにおける、前記標準物質由来のピークβの積分値Bに対する、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計Aの比A/Bに基づいて、前記燃料油における共役ジエン構造の含有割合を求める工程と、を有する、燃料油の分析方法。 - 共役ジエン構造の含有割合が互いに異なる複数の燃料油について、それぞれ標準物質とともに1H−NMRスペクトルを測定して、前記標準物質由来のピークβ’の積分値B’に対する、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークα’の積分値の合計A’の比A’/B’を求める工程と、
前記複数の燃料油について求めたそれぞれの前記比A’/B’と前記含有割合との関係に基づいて、検量線を得る工程と、
燃料油と標準物質とを含有する試料の1H−NMRスペクトルを測定する工程と、
前記試料の1H−NMRスペクトルにおける、前記標準物質由来のピークβの積分値Bに対する、テトラメチルシランを基準として6.1〜6.6ppmに観測される全ピークαの積分値の合計Aの比A/Bと、前記検量線とに基づいて、前記試料に含まれる前記燃料油における共役ジエン構造の含有割合を求める工程と、を有する、燃料油の分析方法。 - 前記標準物質が含酸素化合物又は含珪素化合物である、請求項2又は3に記載の燃料油の分析方法。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2013087077A1 (en) * | 2011-12-12 | 2013-06-20 | Nanonord A/S | A method of determining catalytic fines in an oil |
EP3185006A1 (de) * | 2015-12-21 | 2017-06-28 | Robert Bosch Gmbh | Verwendung eines nmr-messgeräts zur untersuchung von kraftstoff, öl und/oder hydraulikflüssigkeit |
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JP2006104224A (ja) * | 2004-09-30 | 2006-04-20 | Japan Energy Corp | 無鉛ガソリン組成物およびその製造方法 |
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JP2006104224A (ja) * | 2004-09-30 | 2006-04-20 | Japan Energy Corp | 無鉛ガソリン組成物およびその製造方法 |
Non-Patent Citations (2)
Title |
---|
JPN6013029114; J. Burri, R. Crockett, R. Hany, D. Rentsch: '"Gasoline composition determined by 1H NMR spectroscopy"' Fuel Vol.83, No.2, 200401, p.187-193 * |
JPN6013029115; A. Silva, R. San Gil, D. Azevedo, C. Kaiser: '"NMR Analysis of Dienes in Model FCC Gasolines"' Annals of Magnetic Resonance Vol. 4, Issue 3, 2005, p.93-99 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013087077A1 (en) * | 2011-12-12 | 2013-06-20 | Nanonord A/S | A method of determining catalytic fines in an oil |
US9714909B2 (en) | 2011-12-12 | 2017-07-25 | Nanonord A/S | Method of determining catalytic fines in an oil |
EP3185006A1 (de) * | 2015-12-21 | 2017-06-28 | Robert Bosch Gmbh | Verwendung eines nmr-messgeräts zur untersuchung von kraftstoff, öl und/oder hydraulikflüssigkeit |
US10309914B2 (en) | 2015-12-21 | 2019-06-04 | Robert Bosch Gmbh | Use of a measuring appliance for examining fuel, oil and/or hydraulic fluid |
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