JP6240187B2 - トリチル化アルキルアリールエーテル - Google Patents
トリチル化アルキルアリールエーテル Download PDFInfo
- Publication number
- JP6240187B2 JP6240187B2 JP2015520614A JP2015520614A JP6240187B2 JP 6240187 B2 JP6240187 B2 JP 6240187B2 JP 2015520614 A JP2015520614 A JP 2015520614A JP 2015520614 A JP2015520614 A JP 2015520614A JP 6240187 B2 JP6240187 B2 JP 6240187B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- branched
- hydrocarbyl group
- aromatic
- group
- 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
- 150000001346 alkyl aryl ethers Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000446 fuel Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000003208 petroleum Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000002372 labelling Methods 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 25
- 239000003550 marker Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004404 heteroalkyl group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003209 petroleum derivative Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000004949 mass spectrometry Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000003225 biodiesel Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- -1 preferably Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis 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
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- MKSXLRWJVRQIKH-UHFFFAOYSA-N 2-butan-2-yl-4-tritylphenol Chemical compound C1=C(O)C(C(C)CC)=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MKSXLRWJVRQIKH-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical group COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002270 exclusion chromatography 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
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000008096 xylene Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
- 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
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
-
- 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
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Description
2−(sec−ブチル)−4−トリチルフェノール:250mLの1つ口フラスコにマグネチックスターラおよび窒素ブランケットを備えた還流冷却器を装着した。フラスコにトリチルアルコールを6.52グラム(0.025モル)、o−sec−ブチルフェノールを3.77グラム(0.025モル)、および氷酢酸を50mL投入した。混合液を窒素下で、室温にて撹拌したところ、透明で黄色い溶液を得た。ついで濃硫酸(5mL)を一度に添加した。溶液は、すぐに暗赤褐色になった。溶液を室温にて、2日間撹拌し、その間に、固体が分離した。反応混合物をろ過し、固体をフィルター上で数回水で洗浄した。真空オーブンにて、65℃で3時間乾燥後、生成物の収率は7.34グラム(収率75%)であった。MP=135〜136℃である。ゲル浸透クロマトグラフィ(GPC)分析により、純度>99%を示した。その構造を赤外線(IR)、1H−および13C−核磁気共鳴(NMR)分析によって確認した。
((3−(sec−ブチル)−4−(デシルオキシ)フェニル)メタントリチル)トリベンゼン(DecTsBuPh):500mLの3つ口フラスコにマグネチックスターラ、窒素ブランケットを用いた還流冷却器、温度調節器、およびサーモカップルを備えたマントルヒーターを装着した。フラスコにTritosBuPhOHを39.32グラム(0.1モル)、85%の水酸化カリウムペレット6.64グラム(0.1モル)を250mLのジメチルスルホキシドと共に投入した。混合液を110℃まで加熱しながら、窒素下で、撹拌した。全ての水酸化カリウムが溶解した時、その暗色の反応混合物を50℃まで冷却した。そしてブロモデカン(20.7mL、22.12グラム、0.1モル)を一部添加した。約60℃の発熱が観察された。60℃で加熱を8時間維持して、反応混合物を約2グラムの水酸化カリウムペレットおよび約15グラムの塩化ナトリウムを含む約1200mLの水に注いだ。トルエン(約300mL)を加え、混合液を室温で約1時間撹拌した。混合液を分液漏斗に移し、層を分離した。水層を1×100mLのトルエンで洗浄し、洗浄液を元のトルエン層に合わせた。トルエン溶液を無水硫酸マグネシウムで乾燥させた。ろ過後、トルエンを回転蒸発により除去し、49.48グラムの生成物を赤色の油として得た。収率は93%であった。その構造を赤外線(IR)、1H−13C−核磁気共鳴(NMR)、およびガスクロマトグラフ質量分析(GC/MS)により確認した。
GC/MSパラメータ:
−カラム:AgilentDB35m、15.0m×0.25mm×0.25μ
−流量:1.5mL/分 水素キャリアガス
−オーブン:イニシャル:100℃
−ランプ1:20℃/分280℃まで;保持:10分
−ランプ2:20℃/分340℃まで;保持:6分
−注入口温度:280℃
−インサート:スプリットレス;ベント:15分、シングルテーパー、グラスウール、不活性処理済、5062−3587
−注入量:3μL;粘度:5秒、プランジャー:fast
−Mass Transfer Line温度:280℃
−MS Quad:200℃;MS Source:250℃
−Solvent Delay:18.5分
Claims (9)
- 式(Ph3C)mAr(R1)j(OR2)nを有する化合物であって、式中、Phは、フェニル基を示し、Arは、C 6 −C 12 ヒドロカルビル芳香族環であり、R1は、独立して、直鎖、分岐もしくは環式配置の炭素原子を有する非置換飽和C2−C18ヒドロカルビル基または、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非置換非芳香族C 4 −C 18 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非置換非芳香族C4−C18ヒドロカルビル基であり、R2は、独立して、直鎖、分岐もしくは環式配置の炭素原子を有する非置換非芳香族C4−C18ヒドロカルビル基または、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非置換非芳香族C 4 −C 18 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非置換非芳香族C4−C18ヒドロカルビル基であり、
mは、1または2であり、jは、1から4の整数であり、および、nは1から3の整数である、前記化合物。 - jは、1から3の整数であり、およびnは、1または2である請求項1記載の化合物。
- R1は、直鎖、分岐もしくは環式配置の炭素原子を有する非置換飽和C2−C12ヒドロカルビル基または、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非置換非芳香族C 4 −C 12 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非置換非芳香族C4−C12ヒドロカルビル基である請求項2記載の化合物。
- Arは、ベンゼン環であり、jは、1または2であり、nは1であり、R1は、直鎖、分岐もしくは環式配置の炭素原子を有する非置換飽和C2−C8ヒドロカルビル基であり、R2は、直鎖、分岐もしくは環式配置の炭素原子を有する非置換非芳香族C4−C18ヒドロカルビル基であり、およびmは、1である請求項3記載の化合物。
- 石油炭化水素に、または生物由来液体燃料に、式(Ph3C)mAr(R1)j(OR2)nを有し、式中、Phは、フェニル基を示し、Arは、6から20の炭素原子を有する芳香族環であり、R1およびR2は、独立して、置換基として1以上のOH基を有していてもよくかつ直鎖、分岐もしくは環式配置の炭素原子を有する非芳香族C1−C18ヒドロカルビル基または、置換基としてOH基もしくはC1−C18アルコキシ基を有していてもよく、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非芳香族C 4 −C 18 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非芳香族C4−C18ヒドロカルビル基であり、mは、1または2であり、jは、1から4の整数であり、および、nは1から3の整数である少なくとも一種の化合物を添加することを含み、式(Ph3C)mAr(R1)j(OR2)nを有する各化合物が、0.01ppmから20ppmの値で存在する石油炭化水素または生物由来液体燃料の標識方法。
- Arは、C6−C12ヒドロカルビル芳香族環であり、jは、1から3の整数であり、およびnは、1または2である請求項5記載の方法。
- R1は、置換基として1以上のOH基を有していてもよくかつ直鎖、分岐もしくは環式配置の炭素原子を有する非芳香族C2−C12ヒドロカルビル基または、置換基としてOH基もしくはC1−C18アルコキシ基を有していてもよく、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非芳香族C 4 −C 12 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非芳香族C4−C12ヒドロカルビル基である請求項6記載の方法。
- R2は、置換基として1以上のOH基を有していてもよくかつ直鎖、分岐もしくは環式配置の炭素原子を有する非芳香族C4−C18ヒドロカルビル基または、置換基としてOH基もしくはC1−C18アルコキシ基を有していてもよく、直鎖、分岐もしくは環式配置の炭素原子を有しかつ、それぞれが、対応する非芳香族C 4 −C 18 ヒドロカルビル基の2つの炭素原子間の結合中に挿入されている1〜6個の酸素もしくは硫黄原子を含有する、酸素もしくは硫黄含有非芳香族C4−C18ヒドロカルビル基である請求項7記載の方法。
- Arは、ベンゼン環であり、jは、1または2であり、nは、1であり、R1は、置換基として1以上のOH基を有していてもよくかつ直鎖、分岐もしくは環式配置の炭素原子を有する非芳香族C2−C8ヒドロカルビル基であり、R2は、置換基として1以上のOH基を有していてもよくかつ直鎖、分岐もしくは環式配置の炭素原子を有する非芳香族C4−C18ヒドロカルビル基でありおよび、mは1である請求項8記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261668535P | 2012-07-06 | 2012-07-06 | |
US61/668,535 | 2012-07-06 | ||
PCT/US2013/048881 WO2014008164A1 (en) | 2012-07-06 | 2013-07-01 | Tritylated alkyl aryl ethers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015522035A JP2015522035A (ja) | 2015-08-03 |
JP2015522035A5 JP2015522035A5 (ja) | 2017-11-02 |
JP6240187B2 true JP6240187B2 (ja) | 2017-11-29 |
Family
ID=48790659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015520614A Active JP6240187B2 (ja) | 2012-07-06 | 2013-07-01 | トリチル化アルキルアリールエーテル |
Country Status (22)
Country | Link |
---|---|
US (1) | US9422493B2 (ja) |
EP (1) | EP2850161B1 (ja) |
JP (1) | JP6240187B2 (ja) |
KR (1) | KR102096325B1 (ja) |
CN (1) | CN104603245B (ja) |
BR (1) | BR112014032300B1 (ja) |
CY (1) | CY1118424T1 (ja) |
DK (1) | DK2850161T3 (ja) |
ES (1) | ES2601507T3 (ja) |
HR (1) | HRP20161540T1 (ja) |
HU (1) | HUE030639T2 (ja) |
IL (1) | IL236319A (ja) |
IN (1) | IN2014DN10067A (ja) |
LT (1) | LT2850161T (ja) |
MY (1) | MY185165A (ja) |
PL (1) | PL2850161T3 (ja) |
PT (1) | PT2850161T (ja) |
RS (1) | RS55422B1 (ja) |
SI (1) | SI2850161T1 (ja) |
SM (1) | SMT201700100B (ja) |
TW (1) | TWI516468B (ja) |
WO (1) | WO2014008164A1 (ja) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI516469B (zh) | 2013-04-05 | 2016-01-11 | 陶氏全球科技責任有限公司 | 烷基三苯甲基苯基醚 |
CN106536683B (zh) | 2014-05-09 | 2018-09-21 | 罗门哈斯公司 | 用作燃料和油标记物的四芳基甲烷醚 |
WO2015171305A1 (en) | 2014-05-09 | 2015-11-12 | Rohm And Haas Company | Tetrarylmethane ethers as fuel markers |
FR3049614B1 (fr) | 2016-03-30 | 2020-02-07 | Etablissements Steiner | Utilisation de derives de triarylbenzene comme traceurs de marquage de carburants et combustibles liquides, carburants et combustibles liquides contenant de tels derives et procedes correspondants |
US10414899B2 (en) * | 2016-11-30 | 2019-09-17 | Dow Global Technologies Llc | Markers for aqueous compositions |
WO2019195014A1 (en) | 2018-04-05 | 2019-10-10 | Dow Global Technologies Llc | Diaryl ethers as fuel markers |
WO2019195016A1 (en) | 2018-04-05 | 2019-10-10 | Dow Global Technologies Llc | Substituted dibenzofurans as fuel markers |
EP3775109B1 (en) | 2018-04-05 | 2024-03-13 | Dow Global Technologies, LLC | Xanthenes as fuel markers |
CR20220246A (es) | 2019-12-03 | 2022-08-19 | Sicpa Holding Sa | Método para la determinación de la autenticidad y adulteración de hidrocarburos de petróleo marcados |
GEP20237577B (en) | 2019-12-03 | 2023-12-25 | Sicpa Holding Sa | Method of marking petroleum hydrocarbon |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5182046A (en) | 1990-12-05 | 1993-01-26 | Morton International, Inc. | Sodium borohydride composition and improved method of producing compacted sodium borohydride |
AU640314B2 (en) | 1991-05-03 | 1993-08-19 | Nalco Chemical Company | Identification of liquid hydrocarbons using chemical markers |
DE69332902T2 (de) * | 1992-01-29 | 2004-02-05 | Isotag Technology, Inc., North Miami Beach | Verfahren zur identifizierung von chemikalien durch nicht-radioaktive isotope |
DE4320456A1 (de) * | 1993-06-21 | 1994-12-22 | Basf Ag | Verwendung von Aminotriarylmethanen zum Markieren von Kohlenwasserstoffen sowie neue Aminotriarylmethane |
FR2734564B1 (fr) * | 1995-05-24 | 1997-07-04 | Rhone Poulenc Chimie | Procede d'hydroxyalkylation d'un ether aromatique |
EP1191084A2 (en) * | 2000-09-26 | 2002-03-27 | Rohm And Haas Company | Colorless petroleum marker dyes |
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 |
JP2010527893A (ja) | 2007-05-18 | 2010-08-19 | エナフューエル インコーポレイテッド | 水素化ホウ素およびグリセロールからの水素の製造 |
GB201015949D0 (en) * | 2010-09-22 | 2010-11-03 | Medical Res Council Technology | Compounds |
EP2441745B1 (en) * | 2010-10-14 | 2015-08-26 | Dow Global Technologies LLC | Biphenyl benzyl ether marker compounds for liquid hydrocarbons and other fuels and oils |
ES2671578T3 (es) | 2011-05-09 | 2018-06-07 | Dow Global Technologies Llc | Compuestos de orto-fenilfenol útiles como marcadores de hidrocarburos |
WO2012154646A1 (en) | 2011-05-09 | 2012-11-15 | Angus Chemical Company | Ortho- phenylphenol compounds as markers for hydrocarbons and other fuels and oils |
ES2624311T3 (es) | 2011-06-24 | 2017-07-13 | Dow Global Technologies Llc | Éteres tritilados y métodos para marcar combustibles líquidos |
CN104024151A (zh) | 2012-02-03 | 2014-09-03 | 罗门哈斯公司 | 碱金属硼氢化物或碱土金属硼氢化物的研磨 |
TWI518061B (zh) * | 2012-05-04 | 2016-01-21 | 陶氏全球科技責任有限公司 | 三苯甲基化醚 |
TWI516469B (zh) * | 2013-04-05 | 2016-01-11 | 陶氏全球科技責任有限公司 | 烷基三苯甲基苯基醚 |
-
2013
- 2013-06-17 TW TW102121314A patent/TWI516468B/zh active
- 2013-07-01 US US14/590,130 patent/US9422493B2/en active Active
- 2013-07-01 CN CN201380033323.4A patent/CN104603245B/zh active Active
- 2013-07-01 PT PT137370946T patent/PT2850161T/pt unknown
- 2013-07-01 LT LTEP13737094.6T patent/LT2850161T/lt unknown
- 2013-07-01 RS RS20161011A patent/RS55422B1/sr unknown
- 2013-07-01 SI SI201330359A patent/SI2850161T1/sl unknown
- 2013-07-01 WO PCT/US2013/048881 patent/WO2014008164A1/en active Application Filing
- 2013-07-01 JP JP2015520614A patent/JP6240187B2/ja active Active
- 2013-07-01 EP EP13737094.6A patent/EP2850161B1/en active Active
- 2013-07-01 HU HUE13737094A patent/HUE030639T2/en unknown
- 2013-07-01 BR BR112014032300-3A patent/BR112014032300B1/pt active IP Right Grant
- 2013-07-01 KR KR1020157001106A patent/KR102096325B1/ko active IP Right Grant
- 2013-07-01 ES ES13737094.6T patent/ES2601507T3/es active Active
- 2013-07-01 PL PL13737094T patent/PL2850161T3/pl unknown
- 2013-07-01 IN IN10067DEN2014 patent/IN2014DN10067A/en unknown
- 2013-07-01 DK DK13737094.6T patent/DK2850161T3/da active
- 2013-07-01 MY MYPI2014003578A patent/MY185165A/en unknown
-
2014
- 2014-12-17 IL IL236319A patent/IL236319A/en active IP Right Grant
-
2016
- 2016-11-10 CY CY20161101162T patent/CY1118424T1/el unknown
- 2016-11-21 HR HRP20161540TT patent/HRP20161540T1/hr unknown
-
2017
- 2017-02-14 SM SM201700100T patent/SMT201700100B/it unknown
Also Published As
Publication number | Publication date |
---|---|
HRP20161540T1 (hr) | 2017-02-10 |
CN104603245A (zh) | 2015-05-06 |
SI2850161T1 (sl) | 2017-02-28 |
DK2850161T3 (da) | 2016-12-19 |
PL2850161T3 (pl) | 2017-03-31 |
RS55422B1 (sr) | 2017-04-28 |
TWI516468B (zh) | 2016-01-11 |
MY185165A (en) | 2021-04-30 |
US20160194571A1 (en) | 2016-07-07 |
CN104603245B (zh) | 2016-09-28 |
BR112014032300A2 (pt) | 2017-06-27 |
ES2601507T3 (es) | 2017-02-15 |
PT2850161T (pt) | 2016-12-02 |
HUE030639T2 (en) | 2017-06-28 |
WO2014008164A1 (en) | 2014-01-09 |
JP2015522035A (ja) | 2015-08-03 |
IL236319A0 (en) | 2015-02-26 |
EP2850161B1 (en) | 2016-08-24 |
EP2850161A1 (en) | 2015-03-25 |
US9422493B2 (en) | 2016-08-23 |
KR20150036088A (ko) | 2015-04-07 |
CY1118424T1 (el) | 2017-06-28 |
IN2014DN10067A (ja) | 2015-08-21 |
LT2850161T (lt) | 2017-01-10 |
KR102096325B1 (ko) | 2020-04-02 |
IL236319A (en) | 2017-02-28 |
SMT201700100B (it) | 2017-03-08 |
TW201406713A (zh) | 2014-02-16 |
BR112014032300B1 (pt) | 2021-12-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6240187B2 (ja) | トリチル化アルキルアリールエーテル | |
KR101307907B1 (ko) | 액체 탄화수소, 타 연료 및 오일용 비페닐 벤질 에테르 마커 화합물 | |
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 | |
KR101215085B1 (ko) | 액체 탄화수소, 타 연료 및 오일용 마커 화합물 | |
KR101947437B1 (ko) | 트리틸화된 에테르 | |
JP6333359B2 (ja) | アルキルトリチルフェニルエーテル類 | |
WO2012154646A1 (en) | Ortho- phenylphenol compounds as markers for hydrocarbons and other fuels and oils | |
JP6220381B2 (ja) | トリチル化エーテル | |
KR20150093672A (ko) | Thpe 에테르 | |
US9335316B2 (en) | Bisphenol A compounds useful as markers for liquid hydrocarbons and other fuels and oils | |
KR101197304B1 (ko) | 액체 탄화수소, 타 연료 및 오일의 마킹방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20150807 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160616 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170216 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170302 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170602 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20170602 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170619 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170919 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20170919 |
|
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: 20171010 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20171102 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6240187 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |