JP2014522835A - ビフェノールエーテル化合物 - Google Patents
ビフェノールエーテル化合物 Download PDFInfo
- Publication number
- JP2014522835A JP2014522835A JP2014518995A JP2014518995A JP2014522835A JP 2014522835 A JP2014522835 A JP 2014522835A JP 2014518995 A JP2014518995 A JP 2014518995A JP 2014518995 A JP2014518995 A JP 2014518995A JP 2014522835 A JP2014522835 A JP 2014522835A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- ppm
- cycloalkyl
- fuel
- compound
- 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.)
- Granted
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 9
- -1 ether compound Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000446 fuel Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- 238000002372 labelling Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 239000003209 petroleum derivative Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003225 biodiesel Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 0 *OCc1cccc(-c2cc(CO*)ccc2)c1 Chemical compound *OCc1cccc(-c2cc(CO*)ccc2)c1 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- PVSNHUGUKICKON-UHFFFAOYSA-N 1-dodecoxy-2-(2-dodecoxyphenyl)benzene Chemical group CCCCCCCCCCCCOC1=CC=CC=C1C1=CC=CC=C1OCCCCCCCCCCCC PVSNHUGUKICKON-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
2,2’−ビス(ドデシルオキシ)−1,1’−ビフェニル:100mL三口フラスコに、磁気撹拌機、窒素ブランケットを備えた還流冷却器、ならびに温度コントローラーおよび熱電対を備えた加熱マントルを備え付けた。このフラスコに、3.74グラム(0.02モル)の2,2’−ビフェノール、2.8グラム(0.04モル、85重量%)の水酸化カリウム、および25mLのジメチルスルホキシドを装入した。この混合物は、100℃に加熱しつつ、窒素下で撹拌された。約2時間半後、水酸化カリウムが溶解し、この混合物は約70℃まで冷却された。臭化ドデシル(9.60mL;d 1.038;9.97グラム;0.04モル)が一度に添加された。約86℃までの発熱が観察された。発熱が鎮まった後、この反応混合物は、70℃で撹拌された。約5時間後、この反応混合物は、約400mLの水の中に注入された。分離した白色の固体を濾過により回収し、フィルタの上で数回の水で洗浄した。この固体は最初に風乾され、その後50℃の真空オーブン中で約2時間乾燥された。生成物の収量は、9.49グラム(91%)、融点は33〜35℃であった。構造は、IR、1Hおよび13C−NMR、ならびにGC/MS分析により確認された。
FID(水素炎イオン化検出器)を使用した。
Claims (10)
- −OR基が、式(I)中のベンゼン環の2,2’−位置にある、請求項1に記載の化合物。
- Rが、C3−C5またはC9−C18アルキル、C5−C18シクロアルキルまたはC4−C18アルケニルを表す、請求項2に記載の化合物。
- Rが、C10−C18アルキル、C5−C18シクロアルキルまたはC4−C18アルケニルを表す、請求項3に記載の化合物。
- Rが、C10−C18アルキルまたはC5−C18アルケニルを表す、請求項4に記載の化合物。
- Rが、C10−C18アルキルを表す、請求項5に記載の化合物。
- Rが、C10−C16アルキルを表す、請求項6に記載の化合物。
- Rが、C3−C18アルキルまたはC5−C18シクロアルキルを表す、請求項1に記載の化合物
- Rが、C3−C16アルキルまたはC5−C12シクロアルキルを表す、請求項8に記載の化合物。
- Rが、C3−C16アルキルを表す、請求項9に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161502973P | 2011-06-30 | 2011-06-30 | |
US61/502,973 | 2011-06-30 | ||
PCT/US2012/044551 WO2013003538A1 (en) | 2011-06-30 | 2012-06-28 | Biphenol ether compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014522835A true JP2014522835A (ja) | 2014-09-08 |
JP5913588B2 JP5913588B2 (ja) | 2016-04-27 |
Family
ID=46514794
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014518995A Active JP5913588B2 (ja) | 2011-06-30 | 2012-06-28 | ビフェノールエーテル化合物 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20140142346A1 (ja) |
EP (1) | EP2709976B1 (ja) |
JP (1) | JP5913588B2 (ja) |
KR (1) | KR101947441B1 (ja) |
CN (1) | CN103619793B (ja) |
BR (1) | BR112013032866A2 (ja) |
ES (1) | ES2536910T3 (ja) |
MY (1) | MY170063A (ja) |
WO (1) | WO2013003538A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2726585B1 (en) | 2011-06-30 | 2018-08-29 | Dow Global Technologies LLC | Biphenol ether compounds as markers for liquid hydrocarbons and other fuels and oils |
GB2541910B (en) * | 2015-09-03 | 2021-10-27 | Thermographic Measurements Ltd | Thermochromic composition |
CN107057007A (zh) * | 2016-12-29 | 2017-08-18 | 沈阳化工大学 | 一种双酚醚化合物改性酚醛发泡材料及其制备方法 |
GB201913663D0 (en) * | 2019-09-23 | 2019-11-06 | Johnson Matthey Plc | Tracers and method of marking liquids |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS6322893A (ja) * | 1985-08-02 | 1988-01-30 | Chisso Corp | 液晶組成物 |
US20050019939A1 (en) * | 2003-07-25 | 2005-01-27 | Dale Spall | Combination marker for liquids and method identification thereof |
US20050042195A1 (en) * | 2001-12-07 | 2005-02-24 | Sumitomo Chemical Company, Limited | New polymer and polymer light-emitting device using the same |
JP2007009120A (ja) * | 2005-07-01 | 2007-01-18 | Fujifilm Holdings Corp | 液晶組成物、液晶素子、及びシロキサンポリマー架橋体 |
JP2007118197A (ja) * | 2005-10-25 | 2007-05-17 | Pilot Ink Co Ltd | 可逆熱変色性マイクロカプセル顔料 |
JP2009507782A (ja) * | 2005-08-22 | 2009-02-26 | シム、ヒョン・ホ | 2重結合エステル基を有する蛍光標識物質、これを標識及び検出する方法 |
JP2009528417A (ja) * | 2006-03-01 | 2009-08-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 液体用の標識剤としてのリレンの使用 |
JP2014523467A (ja) * | 2011-06-30 | 2014-09-11 | アンガス ケミカル カンパニー | 液体炭化水素およびその他の燃料および油のための標識としてのビフェノールエーテル化合物 |
Family Cites Families (8)
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US2227805A (en) * | 1941-01-07 | Allyi-type ethers of dihydroxy | ||
US4008266A (en) * | 1973-10-18 | 1977-02-15 | Monsanto Company | Coupling of aromatic compounds in the presence of molecular oxygen, a mercuric oxyanion compound, and a group VIII metal or group VIII metal oxyanion compound |
CA2102780C (en) * | 1991-05-10 | 2007-01-09 | Alfred P. Spada | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
ATE238545T1 (de) * | 1992-01-29 | 2003-05-15 | Isotag Technology Inc | Verfahren zur identifizierung von chemikalien durch nicht-radioaktive isotope |
US6811575B2 (en) | 2001-12-20 | 2004-11-02 | Rohm And Haas Company | Method for marking hydrocarbons with anthraquinones |
JP3806119B2 (ja) | 2003-05-23 | 2006-08-09 | ローム アンド ハース カンパニー | 置換アントラキノンを用いた炭化水素のマーキング方法 |
JP3806118B2 (ja) * | 2003-06-13 | 2006-08-09 | ローム アンド ハース カンパニー | 置換アントラキノンでの炭化水素のマーキング方法。 |
US7858373B2 (en) | 2006-02-03 | 2010-12-28 | Rohm And Haas Company | Chemical markers |
-
2012
- 2012-06-28 KR KR1020147000803A patent/KR101947441B1/ko active IP Right Grant
- 2012-06-28 US US14/129,388 patent/US20140142346A1/en not_active Abandoned
- 2012-06-28 WO PCT/US2012/044551 patent/WO2013003538A1/en active Application Filing
- 2012-06-28 JP JP2014518995A patent/JP5913588B2/ja active Active
- 2012-06-28 BR BR112013032866A patent/BR112013032866A2/pt not_active Application Discontinuation
- 2012-06-28 EP EP12735710.1A patent/EP2709976B1/en not_active Not-in-force
- 2012-06-28 CN CN201280028931.1A patent/CN103619793B/zh not_active Expired - Fee Related
- 2012-06-28 MY MYPI2013004295A patent/MY170063A/en unknown
- 2012-06-28 ES ES12735710.1T patent/ES2536910T3/es active Active
Patent Citations (8)
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JPS6322893A (ja) * | 1985-08-02 | 1988-01-30 | Chisso Corp | 液晶組成物 |
US20050042195A1 (en) * | 2001-12-07 | 2005-02-24 | Sumitomo Chemical Company, Limited | New polymer and polymer light-emitting device using the same |
US20050019939A1 (en) * | 2003-07-25 | 2005-01-27 | Dale Spall | Combination marker for liquids and method identification thereof |
JP2007009120A (ja) * | 2005-07-01 | 2007-01-18 | Fujifilm Holdings Corp | 液晶組成物、液晶素子、及びシロキサンポリマー架橋体 |
JP2009507782A (ja) * | 2005-08-22 | 2009-02-26 | シム、ヒョン・ホ | 2重結合エステル基を有する蛍光標識物質、これを標識及び検出する方法 |
JP2007118197A (ja) * | 2005-10-25 | 2007-05-17 | Pilot Ink Co Ltd | 可逆熱変色性マイクロカプセル顔料 |
JP2009528417A (ja) * | 2006-03-01 | 2009-08-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 液体用の標識剤としてのリレンの使用 |
JP2014523467A (ja) * | 2011-06-30 | 2014-09-11 | アンガス ケミカル カンパニー | 液体炭化水素およびその他の燃料および油のための標識としてのビフェノールエーテル化合物 |
Non-Patent Citations (8)
Title |
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ALEXAKIS, ALEXANDRE; POLET, DAMIEN; ROSSET, STEPHANE; MARCH, SEBASTIEN: "Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition", JOURNAL OF ORGANIC CHEMISTRY, vol. 69(17), JPN6015045572, 2004, pages 5660 - 5667, ISSN: 0003194560 * |
ANGELOVSKI, GORAN; EILBRACHT, PETER: "Synthesis of hydroquinone-, biphenol-, and binaphthol-containing aza macroheterocycles via regiosele", TETRAHEDRON, vol. 59(41), JPN6015045574, 2003, pages 8265 - 8274, ISSN: 0003194561 * |
DHANALEKSHMI, SAVITHRI; BALASUBRAMANIAN, KALPATTU KUPPUSAMY; VENKATACHALAM, CHITTOOR SIVARAMAKRISHNA: "Anodic oxidation of aryl propargyl and aryl allyl ethers at a platinum electrode", TETRAHEDRON, vol. 50(21), JPN6015045578, 1994, pages 6387 - 400, ISSN: 0003194563 * |
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MORI, TADASHI; INOUE, YOSHIHISA; GRIMME, STEFAN: "Experimental and theoretical study of the CD spectra and conformational properties of axially chiral", JOURNAL OF PHYSICAL CHEMISTRY A, vol. 111(20), JPN6015045568, 2007, pages 4222 - 4234, ISSN: 0003194558 * |
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Also Published As
Publication number | Publication date |
---|---|
ES2536910T3 (es) | 2015-05-29 |
EP2709976B1 (en) | 2015-03-25 |
KR101947441B1 (ko) | 2019-02-13 |
EP2709976A1 (en) | 2014-03-26 |
MY170063A (en) | 2019-07-02 |
CN103619793B (zh) | 2016-04-06 |
US20140142346A1 (en) | 2014-05-22 |
BR112013032866A2 (pt) | 2017-01-24 |
WO2013003538A1 (en) | 2013-01-03 |
CN103619793A (zh) | 2014-03-05 |
KR20140041722A (ko) | 2014-04-04 |
JP5913588B2 (ja) | 2016-04-27 |
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