ZA200110522B - Aromatic esters for marking or tagging organic products. - Google Patents
Aromatic esters for marking or tagging organic products. Download PDFInfo
- Publication number
- ZA200110522B ZA200110522B ZA200110522A ZA200110522A ZA200110522B ZA 200110522 B ZA200110522 B ZA 200110522B ZA 200110522 A ZA200110522 A ZA 200110522A ZA 200110522 A ZA200110522 A ZA 200110522A ZA 200110522 B ZA200110522 B ZA 200110522B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- carbon atoms
- straight
- branched chain
- hydrogen atom
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title description 8
- 239000003550 marker Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000003209 petroleum derivative Substances 0.000 claims description 26
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 239000000010 aprotic solvent Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000012141 concentrate Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000003849 aromatic solvent Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 5
- 125000000686 lactone group Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical group CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 18
- 239000000446 fuel Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- -1 di-ester compounds Chemical class 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- CPBJMKMKNCRKQB-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 CPBJMKMKNCRKQB-UHFFFAOYSA-N 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 150000002596 lactones Chemical group 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002283 diesel fuel Substances 0.000 description 6
- 235000014666 liquid concentrate Nutrition 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 150000001450 anions Chemical group 0.000 description 5
- 239000003502 gasoline Substances 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HQHBAGKIEAOSNM-UHFFFAOYSA-N naphtholphthalein Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=CC=C(C4=CC=CC=C43)O)=CC=C(O)C2=C1 HQHBAGKIEAOSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007705 chemical test Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000010742 number 1 fuel oil Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Natural products CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 125000003639 thymyl group Chemical group C1(=CC(C)=CC=C1C(C)C)* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- 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
- Y10T436/13—Tracers or tags
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)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Furan Compounds (AREA)
- Lubricants (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/343,467 US6482651B1 (en) | 1999-06-30 | 1999-06-30 | Aromatic esters for marking or tagging petroleum products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200110522B true ZA200110522B (en) | 2002-12-23 |
Family
ID=23346241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200110522A ZA200110522B (en) | 1999-06-30 | 2001-12-21 | Aromatic esters for marking or tagging organic products. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6482651B1 (ko) |
| EP (1) | EP1189871B1 (ko) |
| JP (2) | JP5239110B2 (ko) |
| KR (5) | KR20050055772A (ko) |
| CN (1) | CN1264803C (ko) |
| AR (2) | AR035552A1 (ko) |
| AT (1) | ATE317841T1 (ko) |
| AU (1) | AU769443B2 (ko) |
| BR (1) | BR0011913A (ko) |
| CA (1) | CA2377300C (ko) |
| DE (1) | DE60026027T2 (ko) |
| EA (1) | EA004426B1 (ko) |
| ES (1) | ES2254193T3 (ko) |
| HK (1) | HK1047741B (ko) |
| MX (1) | MXPA01013387A (ko) |
| TR (1) | TR200200635T2 (ko) |
| UA (1) | UA74785C2 (ko) |
| WO (1) | WO2001000561A1 (ko) |
| ZA (1) | ZA200110522B (ko) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6482651B1 (en) * | 1999-06-30 | 2002-11-19 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging petroleum products |
| WO2002003672A1 (en) | 2000-06-29 | 2002-01-10 | Lin Ching Yi | Phone appliance with display screen and methods of using the same |
| US7208451B2 (en) * | 2003-01-29 | 2007-04-24 | Authentic Inc. | IMS detection of chemical markers in petroleum products |
| US20040214341A1 (en) * | 2003-04-25 | 2004-10-28 | Fedorova Galina V. | Analytical method for the detection and quantitation of fuel additives |
| US20050019939A1 (en) * | 2003-07-25 | 2005-01-27 | Dale Spall | Combination marker for liquids and method identification thereof |
| US7061382B2 (en) * | 2003-12-12 | 2006-06-13 | Francis M. Claessens | Apparatus for electronically verifying the authenticity of contents within a container |
| JP4489082B2 (ja) * | 2003-12-12 | 2010-06-23 | クレセンス、フランシス・エム | 製品に対する税が支払われているか否かを電子的に判定するための装置 |
| AU2006283384C1 (en) | 2005-08-24 | 2013-01-10 | Johnson Matthey Plc | Tagging system |
| KR20060018801A (ko) * | 2005-09-02 | 2006-03-02 | 심현호 | 이중결합 에스테르기를 갖는 락톤계 표지물질, 이를 표지및 검출하는 방법 |
| KR100846568B1 (ko) * | 2005-09-02 | 2008-07-15 | 심현호 | 이중결합 에스테르기를 갖는 락톤계 표지물질, 이를 표지및 검출하는 방법 |
| KR101385354B1 (ko) * | 2006-12-07 | 2014-04-14 | 유나이티드 컬러 매뉴팩쳐링, 인코퍼레이티드 | 유기 제품을 마킹하거나 태깅하기 위한 방향족 에스테르의혼합물, 이를 포함하는 마커 조성물, 및 이를 제조하는방법 |
| WO2011032857A2 (de) * | 2009-09-15 | 2011-03-24 | Basf Se | Verwendung von derivaten aromatischer verbindungen als markierstoffe für flüssigkeiten |
| TWI437089B (zh) | 2010-05-27 | 2014-05-11 | Angus Chemical | 標記液體碳氫化合物及其他燃料與油之方法 |
| US9995681B2 (en) * | 2010-09-28 | 2018-06-12 | Authentix, Inc. | Determining the quantity of a taggant in a liquid sample |
| JP5913583B2 (ja) * | 2011-06-24 | 2016-04-27 | ダウ グローバル テクノロジーズ エルエルシー | トリチル化エーテル |
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
| TWI477597B (zh) * | 2012-12-06 | 2015-03-21 | Angus Chemical | Ｔｈｐｅ醚類 |
| 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 |
| WO2015013456A1 (en) * | 2013-07-24 | 2015-01-29 | Indicator Systems International, Inc. | Indicator compounds, polymerizable derivatives thereof and infection indicating medical devices comprising the same |
| RU2630689C2 (ru) * | 2016-03-01 | 2017-09-12 | Савенкова Елена Борисовна | Маркирующая метка для бензинов |
| CN109923412B (zh) | 2016-08-24 | 2021-06-29 | 联合色彩制造股份有限公司 | 标记物组合物及其制造和使用方法 |
| SG11202001569SA (en) | 2017-08-23 | 2020-03-30 | United Color Mfg Inc | Marker compositions with nitrogen compounds, and methods for making and using same |
| JP2021038932A (ja) * | 2019-08-30 | 2021-03-11 | Ｅｎｅｏｓ株式会社 | 潤滑油の判別方法及び潤滑油組成物 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US998726A (en) * | 1908-12-21 | 1911-07-25 | Knoll And Company | Phenolphthalein diisovalerate. |
| GB357179A (en) | 1930-06-17 | 1931-09-17 | Patent Fuels & Color Corp | Improvements in the art of colouring gasoline or other petroleum distillates |
| GB361310A (en) | 1930-06-18 | 1931-11-18 | Howard Ferguson | Improvements in and relating to motor fuels or like combustible liquids |
| US2046365A (en) | 1932-02-24 | 1936-07-07 | Wilmot And Cassidy Inc | Process of testing petroleum hydrocarbons |
| US1997670A (en) | 1932-06-21 | 1935-04-16 | George L Armour | Method of and means for identifying brands of liquid hydrocarbons |
| US2063575A (en) | 1934-03-31 | 1936-12-08 | Standard Oil Co | Dispersing of phenolphthalein in mineral lubricating oils |
| US2522939A (en) | 1949-04-22 | 1950-09-19 | Monsanto Chemicals | Process for the production of phenolphthalein |
| US2522940A (en) | 1949-04-25 | 1950-09-19 | Monsanto Chemicals | Process for the production of phenolphthalein |
| US3468640A (en) | 1964-09-22 | 1969-09-23 | Chevron Res | Gasoline compositions |
| US3488727A (en) | 1968-03-15 | 1970-01-06 | Squibb & Sons Inc | 7alpha-hydroxy-16,17-acetals and ketals of the pregnene series |
| US3764273A (en) | 1971-06-14 | 1973-10-09 | Morton Norwich Products Inc | Novel marker for water immiscible organic liquids and method of marking same |
| US3883568A (en) | 1971-06-14 | 1975-05-13 | Morton Norwich Products Inc | 2-(2{40 ethylhexyl)-quinizarin |
| US3822294A (en) * | 1972-01-07 | 1974-07-02 | Polaroid Corp | 3-acetoxy-3-(3'-carbomethoxy-4'-acetoxy-1'-naphthyl)naphthalide-1,8 and a method for its preparation |
| US3868534A (en) * | 1972-11-29 | 1975-02-25 | Bell Canada Northern Electric | Electrochemiluminescent device having a mixed solvent |
| JPS5136222A (ko) * | 1974-09-21 | 1976-03-27 | Hiroshi Nakada | |
| US4288402A (en) | 1979-04-25 | 1981-09-08 | Virginia Chemicals Inc. | Acid field test kit for refrigeration oils containing a leak detector |
| US4209302A (en) | 1979-05-10 | 1980-06-24 | Morton-Norwich Products, Inc. | Marker for petroleum fuels |
| DE2925580C2 (de) * | 1979-06-25 | 1984-09-13 | Vdo Adolf Schindling Ag, 6000 Frankfurt | Einrichtung zum Regeln der Fahrgeschwindigkeit eines Kraftfahrzeuges |
| US4514503A (en) | 1982-09-01 | 1985-04-30 | Morton Norwich Products | Reagent and process for detecting furfural in petroleum products |
| US4735631A (en) | 1983-12-16 | 1988-04-05 | Morton Thiokol, Inc. | Colored petroleum markers |
| US4764474A (en) | 1983-12-16 | 1988-08-16 | Morton Thiokol, Inc. | Method for detecting a tagging compound |
| US4683241A (en) * | 1984-05-21 | 1987-07-28 | G. D. Searle & Co. | Phenolic ester derivatives as elastase inhibitors |
| DE3540627A1 (de) * | 1984-11-15 | 1986-05-22 | Ricoh Co., Ltd., Tokio/Tokyo | Waermeempfindliches zweifarben-aufzeichnungsmaterial |
| DE3627461A1 (de) | 1986-08-13 | 1988-02-25 | Basf Ag | Farbstoffmischungen |
| US4787916A (en) | 1986-10-31 | 1988-11-29 | Exxon Research And Engineering Company | Method and fuel composition for reducing octane requirement increase |
| US4764290A (en) | 1987-02-02 | 1988-08-16 | National Identification Laboratories, Inc. | Identification marking of oils |
| US4966883A (en) * | 1988-08-17 | 1990-10-30 | James River Graphics, Inc. | Composition for use in thermally sensitive coatings and a thermally sensitive recording material |
| US5066580A (en) | 1988-08-31 | 1991-11-19 | Becton Dickinson And Company | Xanthene dyes that emit to the red of fluorescein |
| US4882057A (en) * | 1988-11-03 | 1989-11-21 | W. R. Grace & Co.-Conn. | Composition and process for separating fluid mixtures |
| US4918020A (en) | 1989-03-21 | 1990-04-17 | Atlantic Richfield Company | Analyzing marker dyes in liquid hydrocarbon fuels |
| DE4001662A1 (de) | 1990-01-22 | 1991-07-25 | Basf Ag | Markierte mineraloele sowie verfahren zum markieren von mineraloelen mittels basischer farbstoffe |
| US5250081A (en) | 1990-12-27 | 1993-10-05 | Exxon Research & Engineering Company | Smoke reducing additive for two-cycle engine lubricant-fuel mixture comprising the Hofmann decomposition products of a quaternary ammonium hydroxide |
| DE4105603A1 (de) | 1991-02-22 | 1992-08-27 | Basf Ag | Oelloesliche phenylazoanilinfarbstoffe |
| US5156653A (en) | 1991-04-18 | 1992-10-20 | Morton International, Inc. | Silent markers for petroleum, method of tagging, and method of detection |
| US5176977A (en) * | 1991-07-01 | 1993-01-05 | Eastman Kodak Company | Nonpolymeric amorphous developer compositions and developing processes |
| US5205840A (en) | 1991-09-30 | 1993-04-27 | Morton International, Inc. | Markers for petroleum, method of tagging, and method of detection |
| EP0543057A1 (en) | 1991-11-20 | 1993-05-26 | Quaker Chemical Corporation | Method for determining the oil content in oil-in-water emulsions |
| US5252106A (en) | 1992-07-29 | 1993-10-12 | Morton International, Inc. | Base extractable petroleum markers |
| US5304493A (en) | 1993-01-22 | 1994-04-19 | Atlantic Richfield Company | Method for detecting a marker dye in aged petroleum distillate fuels |
| DE4308634A1 (de) | 1993-03-18 | 1994-09-22 | Basf Ag | Anthrachinon als Markierungsmittel für Mineralöle |
| DE4334678A1 (de) | 1993-10-12 | 1995-04-13 | Basf Ag | Verfahren zum Nachweis von markierten Mineralölen sowie neue Azofarbstoffe |
| US5498808A (en) | 1995-01-20 | 1996-03-12 | United Color Manufacturing, Inc. | Fluorescent petroleum markers |
| DE69609062T2 (de) * | 1995-04-13 | 2001-03-08 | United Color Mfg Inc | Verfahren zum nachweis von base reagierenden petroleumskraftstoffsmarkierungsmittel |
| RU2159269C2 (ru) * | 1995-04-13 | 2000-11-20 | Юнайтед Колор Мэньюфекчюринг, Инк. | Композиция, включающая нефтепродукт и маркер, способ и раствор для маркирования нефтепродукта и способ идентификации нефтепродукта |
| US5558808A (en) | 1995-06-07 | 1996-09-24 | United Color Manufacturing, Inc. | Colored transmission fluid |
| US5676708A (en) | 1996-02-20 | 1997-10-14 | United Color, Inc. | Non-mutagenic dye |
| US5939468A (en) * | 1996-07-26 | 1999-08-17 | Videojet Systems International, Inc. | Blush resistant invisible fluorescent jet ink |
| US5858930A (en) | 1997-05-30 | 1999-01-12 | United Color Manufacturing, Inc. | Liquid Benz-iso-Quinoline derivatives |
| US5984983A (en) * | 1998-12-04 | 1999-11-16 | Morton International, Inc. | Use of carbonyl compounds as markers |
| US6482651B1 (en) * | 1999-06-30 | 2002-11-19 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging petroleum products |
| US6638977B1 (en) * | 1999-11-19 | 2003-10-28 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists |
| EP1191084A2 (en) * | 2000-09-26 | 2002-03-27 | Rohm And Haas Company | Colorless petroleum marker dyes |
-
1999
- 1999-06-30 US US09/343,467 patent/US6482651B1/en not_active Expired - Lifetime
-
2000
- 2000-06-30 KR KR1020057006768A patent/KR20050055772A/ko not_active Application Discontinuation
- 2000-06-30 EP EP00943336A patent/EP1189871B1/en not_active Expired - Lifetime
- 2000-06-30 KR KR1020027011183A patent/KR100991585B1/ko active IP Right Grant
- 2000-06-30 EA EA200200098A patent/EA004426B1/ru not_active IP Right Cessation
- 2000-06-30 KR KR1020017008772A patent/KR100361255B1/ko active IP Right Grant
- 2000-06-30 DE DE60026027T patent/DE60026027T2/de not_active Expired - Lifetime
- 2000-06-30 MX MXPA01013387A patent/MXPA01013387A/es active IP Right Grant
- 2000-06-30 KR KR10-2004-7018616A patent/KR20050007404A/ko not_active Application Discontinuation
- 2000-06-30 UA UA2001129046A patent/UA74785C2/uk unknown
- 2000-06-30 ES ES00943336T patent/ES2254193T3/es not_active Expired - Lifetime
- 2000-06-30 AT AT00943336T patent/ATE317841T1/de not_active IP Right Cessation
- 2000-06-30 WO PCT/US2000/018062 patent/WO2001000561A1/en active IP Right Grant
- 2000-06-30 BR BR0011913-0A patent/BR0011913A/pt not_active Application Discontinuation
- 2000-06-30 CN CNB008098301A patent/CN1264803C/zh not_active Expired - Fee Related
- 2000-06-30 JP JP2001506975A patent/JP5239110B2/ja not_active Expired - Lifetime
- 2000-06-30 KR KR1020087022791A patent/KR20080089526A/ko not_active Application Discontinuation
- 2000-06-30 AU AU57821/00A patent/AU769443B2/en not_active Expired
- 2000-06-30 CA CA2377300A patent/CA2377300C/en not_active Expired - Fee Related
- 2000-06-30 AR ARP000103343A patent/AR035552A1/es active IP Right Grant
- 2000-06-30 TR TR2002/00635T patent/TR200200635T2/xx unknown
-
2001
- 2001-12-21 ZA ZA200110522A patent/ZA200110522B/en unknown
-
2002
- 2002-11-06 US US10/288,483 patent/US7163827B2/en not_active Expired - Fee Related
- 2002-12-31 HK HK02109456.6A patent/HK1047741B/zh not_active IP Right Cessation
-
2010
- 2010-06-30 AR ARP100102337A patent/AR080061A2/es active IP Right Grant
-
2011
- 2011-01-13 JP JP2011004846A patent/JP5549604B2/ja not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2377300C (en) | Aromatic esters for marking or tagging organic products | |
| EP0804521B1 (en) | Use of fluorescent markers for petroleum products | |
| RU2159269C2 (ru) | Композиция, включающая нефтепродукт и маркер, способ и раствор для маркирования нефтепродукта и способ идентификации нефтепродукта | |
| RU2187538C2 (ru) | Способ идентификации нефтепродукта с использованием маркера и проявляющего реагента | |
| US7825159B2 (en) | Mixtures of aromatic esters for marking or tagging organic products, marker compositions comprising the same and manufacturing methods thereof | |
| AU2012201141B2 (en) | Aromatic esters for marking or tagging petroleum products | |
| AU2008201455A1 (en) | Aromatic esters for marking or tagging petroleum products | |
| AU2004201762A1 (en) | Aromatic esters for marking or tagging petroleum products | |
| CN104140406B (zh) | 用于标示或标记有机产品的芳香酯混合物、包含其的标示物组合物和其制造方法 | |
| AU710997B2 (en) | Novel petroleum fuel markers | |
| MXPA97005483A (en) | Developers of petroleo fluorescen |