JP5913589B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP5913589B2 JP5913589B2 JP2014519015A JP2014519015A JP5913589B2 JP 5913589 B2 JP5913589 B2 JP 5913589B2 JP 2014519015 A JP2014519015 A JP 2014519015A JP 2014519015 A JP2014519015 A JP 2014519015A JP 5913589 B2 JP5913589 B2 JP 5913589B2
- Authority
- JP
- Japan
- Prior art keywords
- ppm
- alkyl
- fuels
- fuel
- formula
- 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.)
- Active
Links
- 239000000446 fuel Substances 0.000 title claims description 29
- 239000007788 liquid Substances 0.000 title claims description 22
- 229930195733 hydrocarbon Natural products 0.000 title claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 18
- 239000003921 oil Substances 0.000 title description 8
- 150000002170 ethers Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 238000002372 labelling Methods 0.000 claims description 14
- 239000003208 petroleum Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003209 petroleum derivative Substances 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000003225 biodiesel Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000010183 spectrum analysis Methods 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000000203 mixture Substances 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
- 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
- 238000001514 detection method 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
- 239000000314 lubricant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance 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
- 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
- 125000004122 cyclic group Chemical group 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
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/22—Fuels; Explosives
-
- 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
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/007—Coloured or dyes-containing lubricant compositions
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/0415—Light distillates, e.g. LPG, naphtha
- C10L2200/0423—Gasoline
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
- C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
-
- 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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/16—Tracers which serve to track or identify the fuel component or fuel composition
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
- G01N33/28—Oils, i.e. hydrocarbon liquids
- G01N33/2835—Specific substances contained in the oils or fuels
- G01N33/2882—Markers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
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。
検出は、FID(水素炎イオン化検出器)を用いて行われた。
Claims (9)
- 各々の式(I)の化合物が0.01ppm〜20ppmの濃度で存在する、請求項1に記載の方法。
- −OR基が、式(I)中のベンゼン環の2,2’−位置にある、請求項2に記載の方法。
- Rが、C2−C18アルキルまたはC3−C18アルケニルを表す、請求項3に記載の方法。
- 各々の式(I)の化合物が、0.01ppm〜10ppmの濃度で存在する、請求項4に記載の方法。
- Rが、C3−C16アルキルまたはC3−C16アルケニルを表す、請求項5に記載の方法。
- 質量スペクトル分析により式(I)の化合物を検出することをさらに含む、請求項に6記載の方法。
- Rが、C4−C16アルキルを表す、請求項7に記載の方法。
- 前記石油炭化水素または生物由来液体燃料が、石油炭化水素、バイオディーゼル燃料またはエタノール燃料である、請求項8に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161502974P | 2011-06-30 | 2011-06-30 | |
US61/502,974 | 2011-06-30 | ||
PCT/US2012/044616 WO2013003573A1 (en) | 2011-06-30 | 2012-06-28 | Biphenol ether compounds as markers for liquid hydrocarbons and other fuels and oils |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014523467A JP2014523467A (ja) | 2014-09-11 |
JP5913589B2 true JP5913589B2 (ja) | 2016-04-27 |
Family
ID=46516835
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014519015A Active JP5913589B2 (ja) | 2011-06-30 | 2012-06-28 | 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 |
Country Status (9)
Country | Link |
---|---|
US (1) | US9222928B2 (ja) |
EP (1) | EP2726585B1 (ja) |
JP (1) | JP5913589B2 (ja) |
KR (1) | KR20140051229A (ja) |
CN (1) | CN103620009B (ja) |
BR (1) | BR112013032885B1 (ja) |
ES (1) | ES2694823T3 (ja) |
MY (1) | MY169067A (ja) |
WO (1) | WO2013003573A1 (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5913588B2 (ja) * | 2011-06-30 | 2016-04-27 | ダウ グローバル テクノロジーズ エルエルシー | ビフェノールエーテル化合物 |
TWI494424B (zh) * | 2012-11-20 | 2015-08-01 | Dow Global Technologies Llc | 可蒸餾燃料標記物 |
TWI591338B (zh) * | 2013-05-02 | 2017-07-11 | 羅門哈斯公司 | 偵測燃料標記物之分析方法 |
TWI591339B (zh) * | 2013-05-02 | 2017-07-11 | 羅門哈斯公司 | 偵測燃料標記物之分析方法 |
EP3140271B1 (en) | 2014-05-09 | 2020-06-24 | Rohm and Haas Company | Tetrarylmethane ethers for use as fuel and oil markers |
CN106536685B (zh) * | 2014-05-09 | 2018-08-17 | 罗门哈斯公司 | 作为燃料标记物的四芳基甲烷醚 |
US9631152B2 (en) * | 2015-03-20 | 2017-04-25 | Authentix, Inc. | Fuel markers and methods of producing and using same |
GB201517474D0 (en) * | 2015-10-02 | 2015-11-18 | Johnson Matthey Plc | Identification of products |
KR101622920B1 (ko) * | 2015-11-20 | 2016-05-20 | 한국석유관리원 | 석유 제품의 식별 방법 및 석유 제품 식별용 조성물 |
PL3775110T3 (pl) | 2018-04-05 | 2023-05-22 | Dow Global Technologies, Llc | Podstawione dibenzofurany jako markery paliwowe |
ES2978190T3 (es) | 2018-04-05 | 2024-09-06 | Dow Global Technologies Llc | Xantenos como marcadores de combustible |
MX2020009853A (es) | 2018-04-05 | 2020-10-15 | Dow Global Technologies Llc | Eteres de diarilo como marcadores de combustible. |
GB201913663D0 (en) * | 2019-09-23 | 2019-11-06 | Johnson Matthey Plc | Tracers and method of marking liquids |
HUE065102T2 (hu) | 2019-12-03 | 2024-05-28 | Sicpa Holding Sa | Módszer a jelölt kõolaj-szénhidrogének eredetiségének és hamisításának meghatározására |
PE20221571A1 (es) | 2019-12-03 | 2022-10-06 | Sicpa Holding Sa | Metodo de marcaje de un hidrocarburo de petroleo |
GB202006913D0 (en) | 2020-05-11 | 2020-06-24 | Johnson Matthey Plc | Tracers and method of marking liquids |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU640314B2 (en) | 1991-05-03 | 1993-08-19 | Nalco Chemical Company | Identification of liquid hydrocarbons using chemical markers |
RU2095807C1 (ru) * | 1992-01-29 | 1997-11-10 | II Давид Кинг Андерсон | Способ маркировки жидкой среды при ее транспортировке и транспортируемая жидкая среда |
DE4238994A1 (de) * | 1992-11-19 | 1994-05-26 | Basf Ag | Aniline als Markierungsmittel für Mineralöle |
GB2354070A (en) * | 1999-09-07 | 2001-03-14 | Duncan William John Mccallien | Markers for identifying liquids |
KR100528322B1 (ko) | 2001-09-28 | 2005-11-15 | 삼성에스디아이 주식회사 | 청색 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
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。 |
US20050019939A1 (en) * | 2003-07-25 | 2005-01-27 | Dale Spall | Combination marker for liquids and method identification thereof |
US7858373B2 (en) * | 2006-02-03 | 2010-12-28 | Rohm And Haas Company | Chemical markers |
TWI444467B (zh) * | 2010-05-27 | 2014-07-11 | Angus Chemical | 用於液體碳氫化合物及其他燃料與油之標記物化合物 |
ES2549031T3 (es) * | 2010-10-14 | 2015-10-22 | Dow Global Technologies Llc | Compuestos marcadores de bifenil bencil éter para hidrocarburos líquidos y otros combustibles y aceites |
ES2909143T3 (es) * | 2010-11-03 | 2022-05-05 | Corbion Biotech Inc | Microbios de Chlorella o Prototheca modificados genéticamente y aceite producido a partir de estos |
WO2012154668A1 (en) | 2011-05-09 | 2012-11-15 | Angus Chemical Company | Ortho - phenylphenol compounds useful as hydrocarbon markers |
KR101914078B1 (ko) | 2011-05-09 | 2018-11-01 | 다우 글로벌 테크놀로지스 엘엘씨 | 탄화수소, 타 연료 및 오일용 마커로서의 오르토-페닐페놀 화합물 |
JP5913588B2 (ja) | 2011-06-30 | 2016-04-27 | ダウ グローバル テクノロジーズ エルエルシー | ビフェノールエーテル化合物 |
-
2012
- 2012-06-28 WO PCT/US2012/044616 patent/WO2013003573A1/en active Application Filing
- 2012-06-28 JP JP2014519015A patent/JP5913589B2/ja active Active
- 2012-06-28 EP EP12735987.5A patent/EP2726585B1/en active Active
- 2012-06-28 MY MYPI2013004296A patent/MY169067A/en unknown
- 2012-06-28 BR BR112013032885A patent/BR112013032885B1/pt active IP Right Grant
- 2012-06-28 CN CN201280028970.1A patent/CN103620009B/zh active Active
- 2012-06-28 ES ES12735987.5T patent/ES2694823T3/es active Active
- 2012-06-28 US US14/129,467 patent/US9222928B2/en active Active
- 2012-06-28 KR KR1020147000805A patent/KR20140051229A/ko active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
WO2013003573A1 (en) | 2013-01-03 |
CN103620009A (zh) | 2014-03-05 |
KR20140051229A (ko) | 2014-04-30 |
BR112013032885B1 (pt) | 2020-04-22 |
EP2726585A1 (en) | 2014-05-07 |
EP2726585B1 (en) | 2018-08-29 |
JP2014523467A (ja) | 2014-09-11 |
US9222928B2 (en) | 2015-12-29 |
BR112013032885A2 (pt) | 2017-01-24 |
MY169067A (en) | 2019-02-12 |
ES2694823T3 (es) | 2018-12-27 |
US20140134746A1 (en) | 2014-05-15 |
CN103620009B (zh) | 2015-07-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5913589B2 (ja) | 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 | |
JP5913583B2 (ja) | トリチル化エーテル | |
KR101215085B1 (ko) | 액체 탄화수소, 타 연료 및 오일용 마커 화합물 | |
KR101307907B1 (ko) | 액체 탄화수소, 타 연료 및 오일용 비페닐 벤질 에테르 마커 화합물 | |
JP6240187B2 (ja) | トリチル化アルキルアリールエーテル | |
WO2012154646A1 (en) | Ortho- phenylphenol compounds as markers for hydrocarbons and other fuels and oils | |
EP2844630B1 (en) | Tritylated ethers | |
JP5913588B2 (ja) | ビフェノールエーテル化合物 | |
US9335316B2 (en) | Bisphenol A compounds useful as markers for liquid hydrocarbons and other fuels and oils | |
US9005315B2 (en) | Bisphenol A compounds as markers for liquid hydrocarbons and other fuels and oils | |
TWI437089B (zh) | 標記液體碳氫化合物及其他燃料與油之方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20141209 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20141209 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150615 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20151119 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20151124 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160216 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160314 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160401 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5913589 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |