AU686838B2 - Use of benzaldehydes to mark hydrocarbons - Google Patents
Use of benzaldehydes to mark hydrocarbons Download PDFInfo
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- AU686838B2 AU686838B2 AU29263/95A AU2926395A AU686838B2 AU 686838 B2 AU686838 B2 AU 686838B2 AU 29263/95 A AU29263/95 A AU 29263/95A AU 2926395 A AU2926395 A AU 2926395A AU 686838 B2 AU686838 B2 AU 686838B2
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- Australia
- Prior art keywords
- der
- alkyl
- lip
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- 150000003935 benzaldehydes Chemical class 0.000 title claims description 26
- 229930195733 hydrocarbon Natural products 0.000 title claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 24
- -1 1,4-butylene Chemical group 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000003550 marker Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- UNQLRWBLUDHEDR-UHFFFAOYSA-N morpholin-4-yl-piperidin-1-yl-pyrrolidin-1-yl-lambda3-chlorane Chemical compound N1(CCCC1)Cl(N1CCOCC1)N1CCCCC1 UNQLRWBLUDHEDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 235000019987 cider Nutrition 0.000 claims 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 2
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 claims 1
- 101150076749 C10L gene Proteins 0.000 claims 1
- 101150031867 Faxc gene Proteins 0.000 claims 1
- 208000010038 Ischemic Optic Neuropathy Diseases 0.000 claims 1
- 206010030924 Optic ischaemic neuropathy Diseases 0.000 claims 1
- 235000010716 Vigna mungo Nutrition 0.000 claims 1
- 244000042295 Vigna mungo Species 0.000 claims 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 1
- 201000002761 non-arteritic anterior ischemic optic neuropathy Diseases 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002283 diesel fuel Substances 0.000 description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- SUSCOLVXUKHTET-UHFFFAOYSA-N 2,3-dimethylchromenylium Chemical compound C1=CC=C2[O+]=C(C)C(C)=CC2=C1 SUSCOLVXUKHTET-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101150054880 NASP gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 229940098895 maleic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-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
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 125000002958 pentadecyl 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])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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
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- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
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- 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
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- C10M171/007—Coloured or dyes-containing lubricant compositions
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- 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
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- G01N33/2835—Specific substances contained in the oils or fuels
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- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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Description
BASF Aktiengesellschaft 940050 o.z. 0050/45034 Use of benzaldehydes for marking hydrocarbons The present invention relates to the use of benzaldehydes of the formula I
RI
R2 (1) H I
R
3 in which the ring A may be benzofused, and
R
1
R
2 and R 3 are each, independently of one another, hydrogen, hydroxyl, Ci-C 1 s-alkyl, Cl-C]5-alkoxy, cyano, nitro or a radical of the formula NR 4
R
5 or COOR 6 where
R
4 is hydrogen or C 1
-C
15 -alkyl with or without interruption by from 1 to 4 oxygen atoms in eti.er function and with a without substitution by phenyl,
R
5 is C 1
-C
1 5 -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without substitution by phenyl, or is a radical of the formula L-NX1X 2 where L is C 2
-C
8 -alkylene and X 1 and X 2 are singly, independently of each other, Ci-C 6 -alkyl or together, together with the nitrogen atom joining them together, a 5- or 6-membered saturated heterocyclic radical with or without an oxygen atom in the ring, and
R
6 is hydrogen, C 1 -Cis-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function or a radical of the formula L-NX'X 2 where L, X 1 and X 2 are each as defined above, as markers for hydrocarbons, to a method for detecting these benzaldehydes in hydrocarbons, and to hydrocarbons comprising the abovementioned benzaldehydes.
US-A-5 145 573, US-A-5 182 372 and EP-A-499 845 disclose azo dyes which are used as markers for mineral oils. US-A-4 009 008 describes a method for marking mineral oils with disazo dyes by BASF Aktiengesellschaft 940050 O.Z. 0050/45034 2 visibilizing the dye added to the mineral oil by adding to the marked mineral oil an adsorbent which binds other colored ingredients of the mineral oil.
OE-A-3 608 215 and DE-A-3 724 757 describe benzopyran derivatives and their use in recording systems.
Example 1 of DE-3-608 215 describes the reaction of 2,3-dimethylbenzopyrylium trichlorozincate "ith 4-dimethylaminobenzaldehyde in methanol to form the colors salt of the formula
SCH
3 0 CH=CH- 2- N(CH 3 2 ZnCl 3 WO-A-11 466/1994 describes the use of substituted anilines for marking mineral oils.
T' is an object of the present invention to provide novel markers 1 ydrocarbons. The novel markers should be readily obtainable uble in hydrocarbons. They should also be simple to detect; specifically, even very small amounts of marker should be visibilizable through a strong color reaction.
We have found that this object is achieved by the above-defined benzaldehydes of the formula I.
Any alkyl or alkylene appearing in the abovementioned formula I may be straight-chain or branched.
X
1 and X 2 combined with the nitrogen atom joining them together into a 5- or 6-membered saturated heterocyclic radical with or without an oxygen atom in the ring can be for example pyrrolidinyl, piperidinyl or morpholinyl.
R
1
R
2
R
3
R
4
R
5
R
6
X
1 and X 2 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
R
1
R
2
R
3
R
4
R
5 and R 6 may each also be for example heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl or pentadecyl (the above designations isooctyl, isononyl, isodecyl and isotridecyl are trivial names derived from )i the oxo process alcohols cf. Ullmann's Encyclopedia of B21SF AktiongcsollSchaft 905 05/53 940050 O.Z. 0050/45034 3 industrial Chemistry, 5th Edition, Vol.. Al, pages 290 to 293, and also Vol. A 10, pages 284 and 285).
RI, R 2 and R 3 may each also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, nonyloxy, isononyloxy, decyloxy, isode~yloxy, undecyloxy, dodecyloxy, tridecyloxy, 3,5,5, 7-tetramethylnonyloxy, isotridecyloxy, tetradecyloxy or pentadecyloxy.
R
4 and RS may each also be for example 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2or 3-butoxypropy., 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4, 8-dioxanonyl, 3, 7-dioxaoctyl, 3, 7-dioxanonyl, 4' 7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6, 8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, benzyl or 1- or 2-phenylethyl.
L is for example (CH 2 2
(CH
2 3
(CH
2 4
(CH
2 5
(CH
2 6
(CH
2 7
(CH
2
CH(CH
3
)CH
2 or CH(CH 3
)CH(CH
3 Preference according to the present invention is given to the use of benzaldehydes of the formula I where at least one of the radicals RI to R 3 is a radical of the formula NR 4
R
5 where R 4 and R 5 are each as defined above.
Particular preterence for the marking of hydrocarbons is given to the use of benzaldehydes of the formula la 0 R1 R C N 351 (Ia), where RI, R 2
R
4 and R 5 are each as defined above.
of particular suitability are benzaldehydes of the formula Ia where R 1 and R 2 are independently of each other hydrogen, hydroxyl, Cl-C, 5 -alkyl, CI-C 1 5 -alkoxy or a radical of the formula BASF Aktiengesollschaft 940050 O.Z. 0050/4bO34 4
COOR
6 where R 6 is as defined above, R 4 is hydrogen or CI-C 1 i-alkyl and R 5 is C 1 -Ci 5 -alkyl.
Particular preference for the marking of hydrocarbons is given to the use of benzaldehydes of the formula la where R 4 and R 5 are independently of each other CI-C 13 -alkyl and R 1 and R 2 are each hydrogen.
The present invention also provides a method of detecting benzaldehydes of formula I in hydrocarbons, which comprises treating the hydrocarbon with an aqueous-alcoholic or alcoholic m-dium comprising a protic acid, at least one compound from the group of compounds consisting of substituted benzopyrylium salts of the formula II R7 B X e I
I),
C where R 7 is CI-C-alkyl, phenyl, Ci-Cs-alkoxy or halogen and RB is methyl or R 7 and R 8 together are 1,4-butylene and the ring B may be fused with a benzene ring and may be substituted by
C
1
-C
4 -alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 optionally also by hydroxyl,
C
1
-C
4 -alkoxy, mono- or di(Ci-C 5 -alkyl)amino which may in turn be substituted by chlorine or phenyl, and X O is an optional anion, and indoles of the formula III Rlo rtnf
(III),
S R 9
H
where R 9 and R 10 are independently of each other hydrogen, hydroxyl, a radical of the formula NR 4
R
5 where R 4 and R 5 are each as defined above, C 1 -Cs-alkyl, phenyl, Cl-C 5 -alkoxy or halogen, and optionally a halide of the metals zinc, aluminum or tin.
Preference according to the present invention is given to the use of indoles of the formula III, especially 2-phenylindole.
JASF Aktiengesellschaft 940050 O.Z. 0050/45034 Examples of suitable anions X' are tetrachlorozincate, halide, sulfate, tetrafluoroborate and phosphate.
The benzaldehydes I, the benzopyrylium salts 1. and also the inaoles III are generally known per se.
Marking for the purposes of the present invention is the addition to hydrocarbons of the benzaldehydes of the formula I in such a concentration that, to the human eye, the hydrocarbons have barely any or no visible color, but the benzLdehydes of the formula I are readily and distinctly visibly detectable by the methods of detection more particularly described herein.
The present invention further provides hydrocarbons comprising one or more of the benzaldehydes of the formula I.
Hydrocarbons for the purposes of the present invention are aliphatic or aromatic hydrocarbons which are liquid under standard conditions. These are in particular mineral oils, for example motor fuels, such as gasoline, kerosene or diesel fuel, or oils, such as fuel oil or engine oil.
The benzaldehydes of the formula I are especially suitable for marking mineral oils where some form of marking is mandatory, for example for tax reasons. To keep the costs for this to a minimum, it is desirable to keep the amount of marker used to a minimum.
To mark hydrocarbons, the benzaldehydes of the formula I are used either without a solvent or in the form of solutions. Suitable solvents are organic solvents. Preference is given to using aromatic hydrocarbons, such as toluene, Lene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics available from Shell as Shellsol® AB. To avoid the resulting solution having a high viscosity, the concentration of benzaldehyde I chosen for the solution generally ranges from 5 to 80 by weight, based on the solution.
The solubility may be improved by using further, co-solvents, for example alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butylethylene glycol or methylpropylene glycol, amines, such as triethylamine, diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N,N-dimethylaniline, toluidine or xylidine, alkanolamines, such as 3-(2-methoxyethoxy)propylamine, o-cresol, m-cresol or p-cresol, ketones, such as diethyl ketone or cyclohexanone, lactams, such as y-butycolactone, carbonates, such as ethylene BASF Aktiongesollschaft 940050 O.Z. 0050/415034 6 carbonate or propylene carbonate, phenols, such as t-butylphenol or nonylphenol, esters, such as methyl phthalate, ethyl phthalate, 2-ethylhexyl phthalate, ethyl acetate, butyl acetate or cyclohexyl acetate, amides, such as N,N-dimethylformamide, N,N-diethylacetamide or N-methylpyrrolidinone, or mixtures thereof.
The benzaldehydes of the formula I to be used according to the present invention permit very simple detection of marked hydrocarbons, even if the marker substances are present only in a concentration of about 10 ppm or less.
The presence in hydrocarbons of the compounds of the formula I used as markers is advantageously detected on treating the hydrocarbon with an aqueous-alcoholic or alcoholic medium comprising a pyrylium salt of the formula II and/or an indole of the formula III, a protic acid and optionally a halide of the metals zinc, aluminum or tin. In aqueous-alcoholic media, the weight ratio of water alcohol varies from 0.5 1 to 4 1, and is preferably about 1 1. The result is a distinctly visible color change of the aqueous-alcoholic phase.
Suitable alcohols include for example ethanol, propanol, isopropanol, 1-methoxypropan-2-ol, ethylene glycol or 1,2- or 1,3-propylene glycol. The use of ethanol is preferred.
Suitable protic acids for the method of the present invention include in particular strong acids, i.e. protic acids whose pKa value is 3.5. Such acids include for example inorganic or organic acids, such as perchloric acid, hydroiodic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, nitric acid, phosphoric acid, benzenesulfonic acid, toluenesulfonic acid, naphthalenesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid, chloroacetic acid, dichloroacetic acid or bromoacetic acid. In some cases it can be of advantage to buffer these acids, for example by adding acetic acid.
As well as to o- or p-toluenesulfonic acid, preference is given especially to inorganic acids, with hydrochloric acid and sulfuric acid being particularly preferred.
Suitable halides of the metals zinc, aluminum or tin include for example zinc chloride, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride. Zinc chloride is particularly preferred.
BASF Aktiengesellschaft 940050 O.z. 0050/45034 7 It is generally sufficient to extract from about 10 to 50 ml of the hydrocarbon marked according to the present invention with from 1 to 50 ml of an aqueous-alcoholic or alcoholic solution of a pyrylium salt of the formula II and/or of an indole of the formula III, a protic acid, optionally in the presence of a metal halide, to obtain a color change. It is also possible to replace the solution of the protic acid by an aqueous-alcoholic solution of a metal halide alone, since the latter likewise has an acid reaction.
The concentration of the protic acid in the aqueous-alcoholic or alcoholic solution is generally from 5 to 50 by weight, preferably from 10 to 30 by weight. The concentration of metal halide is generally from 0 to 50 by weight, preferably from 5 to 20 by weight, in each case based on the weight of the solution.
One considerable advantage of the invention is that two different methods can be used for detecting the benzaldehydes of the formula I. Detection is therefore very reliable, even in the presence of possible interference (eg. additives in diesel fuel).
The Examples which follow illustrate the invention.
General method 1: Commercial diesel fuel was mixed with 10 ppm each of benzaldehyde. For this the aldehyde was predissolved in toluene in 0.1 strength by weight and this solution was added to the diesel fuel.
In each of Examples 1 to 12 10 ml of the diesel fuel thus marked were admixed with 2 ml of reagent solution and shaken for 5 minutes. Then 1 ml of water was added and the shaking was continued for a further 5 minutes. The aqueous phase showed the color indicated below in Table No. 1.
Reagent solution 1 ml of 1 strength by weight indole in ethanol 5 ml of concentrated hydrochloric acid g of zinc chloride ml of acetic acid BASF Aktiengescllschaft 940050 O.Z. 0050/45034 8 Reagent solution 2 ml of 1 strength by weight 2-methylindole in ethanol ml of concentrated hydrochloric acid 5 g of zinc chloride ml of acetic acid Reagent solution 3 5 ml of 1 strength by weight 2-phenylindole in ethanol ml of concentrated hydrochloric acid g of zinc chloride ml of acetic acid Particularly advantageous results are obtained on first filtering the diesel fuel through silica gel.
I B~ASF Aktiengesellschaft 905 940050 o.Z. 0050/45034 Table No. 1 Ex. No.
1 Aldehyde
CHO
N (CH- 3 2 Reagent lColor 1 magent- I vioiet 2 et
CHO
N (CH 3 2 3 CH 3jviolet N(CH 2 4
CHO
S -OH
N(C
2
H
5 )2 orange 2 treddish violet
CHO
S -OH
N(C
2 H 5 2 FnASF Aktiengesellschaft 905 05/53 940050 O.Z. 0050/45034 Ex. No. Aldehyde Reagent Color 6 3 magenta CHOb
N(C
2
H
5 2 7 CHO 1 orange 8 CHO 2 reddish violet
OH
9 CHO 3 magenta
OH
1 ireddish violet
CHO
-CO
2
CH
3 N (CH 3 2 J3Asir Aktiongese1J4Wh'Ift 9L0 940050 O.Z. 00b0/4!)034 Ex. No. Aldehyde Reagent Color 112 bluish violet CH0 ~-C0 2
CH
3
N(CH
3 2 12 3 bluish violet
CHO
I- IC 2
CH
3
N(CH
3 2 Similar results are obtained on using markers comprising the benzaldehydes listed below in Table No. 2.
Table No. 2 113 Aldehyde
CHO
N(C
2 Hs )2 14
N(CH
2
C
6
H
5 )2 0ASF Aktion90061100b0ft 940050 94OOL~O 00!)0/00O34 Ex. No.
12 AldehydeI
CHO
16 [CHO 17 CH0 18 19
CH
3
-N-C
2
H
4
CII
CHO
OHR
N(CH
3 2
CHO
OH
N( (CH 2
C
6
H
5 2
CHO
OCR3
N(C
2
H
5 2 BASF Aktiengesollschaft 940050 o.z. 0050/45034 13 General method 2 Commercial diesel fuel was mixed with 10 ppm of each benzaldehyde. For this the benzaldehyde was predissolved in toluene in 0.1 strength by weight and this solution was added to the diesel fuel.
In each of Examples 21 to 30 10 ml of the marked diesel fuel were admixed with 2 ml of reagent solution 4 and refluxed for 5 minutes. Then 1 ml of 1:1 v/v water/ethanol was added and the mixture was shaken for a further 5 minutes. The aqueous phase showed the color indicated below in Table No. 3.
Reagent solution 4 ml of the benzopyrylium salt of the formula 1-1Q CH3 ZnCl 3 25 ml of 225 ml of 1 strength in water concentrated hydrochloric acid acetic acid Table 3 Ex. No. Aldehyde Q Color 21 C 6
H
5 blue
CHO
N(CH3)2 22 CH 3 blue
CHO
N(CH
3 2 B3ASF~ AktioflgasllaclhnfL 940050 94O~i0O.Z. 0050/450O34 0 Ex. No.
23 Aldehyde Q Coolor
I
C6H,, blue 24 26
CHO
C0 2
CR
3
N(CH
3 2
CHO
-C0 2
CH
3 N(CRH )2 CH0 0 H
N(C
2
R
5 )2
CHO
O ~H
CHO
H 1 blue CH3 Iblue
CH
3 iblue r27 H tblue
L-
nASP Aktiongesollf3chaft 94O00 O.Z. 0050/45034 I. Color Ex. No.
28 Aldehyde_ IQ color
'I
reddish violet reddish violet
OH
reddish violet 2
CHO
OCH3 reddish violet
CH
3 j violet
CHO
OCH
3
OCH
3 Simtilar results are obtained on replacing the benzopyryliumr salt at reagent solution 5 by that of the formula 0 ZnClae 0D
Claims (8)
1. The use of benzaldehydes of the formula I RI 0 R2 (I) H R3 in which the ring A may be benzofused, and R 1 R 2 and R 3 are each, independently of one another, hy- drogen, hydroxyl, C 1 -C 15 -alkyl, Ci-C 15 -alkoxy, cyano, nitro or a radical of the formula NR 4 R 5 or COOR 6 where R 4 is hydrogen or C-Cls-alkyl with or without inter- ruption by from 1 to 4 oxygen atoms in ether function and with or without substitution by phenyl, R 5 is C 1 -C 1 i-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without substitution by phenyl, or is a radical of the formula L-NXIX 2 where L is C 2 -Co-alkylene and X 1 and X 2 are singly, independently of each other, Ci-C 6 -alkyl or together, together with the nitrogen atom joining them together, a 5- or 6-membered saturated heterocyclic radical with or without an oxygen atom in the ring, and R 6 is hydrogen, Cl-C 15 -alkyl with or without interrup- tion by from 1 to 4 oxygen atoms in ether function or a radical of the formula L-NXIX 2 where L, X 1 and X 2 are each as defined above, as markers for hydrocarbons.
2. A use as claimed in claim 1 wherefor the benzaldehydes con- form to the fc.mula Ia 0 4 0.' [ASF Aktlongeoollschaft 940050 O.Z. 0050/45034 I R 2 (Ia) where R 1 R 2 R 4 and R 5 are each as defined in claim 1.
3. A use as claimed in claim 1 or 2 wherefor R 1 and R 2 are inde- pendently of each other hydrogen, hydroxyl, Ci-Cis-alkyl, C 1 -C 25 -alkoxy or a radical of the formula COOR 6 where R 6 is as defined in claim 1, R 4 is hydrogen or Cl-C 15 -alkyl and R 5 is C 1 -C 15 -alkyl.
4. A method of detecting benzaldehydes of formula I as set forth in claim 1 in hydrocarbons, which comprises treating the hy- drocarbon with an aqueous-alcoholic or alcoholic medium com- prising a protic acid, at least one compound from the group of compounds consisting of substituted pyrylium salts of the formula II R 7 B25 X (II), R 8 where R 7 is Ci-Cg-alkyl, phenyl, C 1 -Cs-alkoxy or halogen and R 8 is methyl or R 7 and R 8 together are 1,4-butylene and the ring B may be fused with a benzene ring and may be substi- tuted by C-C 4 -alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 optionally also by hydroxyl, C 1 -C 4 -alkoxy, mono- or di(Cl-C 5 -alkyl)amino which may in turn be substituted by chlorine or phenyl, and XO is an optional anion, and indoles of the formula III Rl0 (III), H 18 where R9 and Rio are independently of each other hydrogen, hydroxyl, a radical of the formula NR4R5, where R4 and R5 are each as defined in claim 1, C1-C 8 -alkyl, phenyl, Ci-Cs-alkoxy or halogen, and optionally a halide of the metals zinc, aluminum or tin. A hydrocarbon with a marker comprising one or more benzaldehydes of the formula I as set forth in claim 1.
6. The use of benzaldehydes substantially as herein described with reference to the examples. DATED this 28th day of October, 1997. BASF AKTIENGESELLSCHAFT WATERMARK PATENT TRADEMARK ATTORNEYS 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRALIA LCG:SI:JL VAX doc 17 AU2926395.WPC lASF Aktiengeosolechaft 940050 o.z. 0050/45034 I W V Use of benzaldehydes for marking hydrocarbons Abstract Benzaldehydes of the formula where the ring A may be benzofused, and R 1 R 2 and R 3 are each, independently of one another, hydrogen, hydroxyl, Ci-C 5 i-alkyl, Ci-C 15 -alkoxy, cyano, nitro or a radical of the formula NR 4 R 5 or COOR 6 where R 4 is hydrogen or C 1 -C 1 s-alkyl with or without substitution, R 5 is Ci-C 15 -alkyl with or without substitution, or is a radical of the formula L-NXIX 2 where L is C 2 -CO-alkylene and X I and X 2 are singly, independently of each other, Ci-C 6 -alkyl or together, together with the nitrogen atom joining them together, a heterocyclic radical, and R 6 is hydrogen, C 1 -Cjs-alkyl with or without substitution or a radical of the formula L-NX'X 2 where L, X 1 and X 2 are each as defined above, are useful as markers for hydrocarbons. INTIECRNAIIONAL SEARCI I rItPOW I Jl"'r A plisun REPOR PCT/EP 95/02558 A. (I.ASSIIICATION OF SUIIUT:C MAI'lt l IPC 6 C10L1/00 C10M171/00 GO1N31/22 G01N33/28 C10L1/18 C10L1/22 According to IntemaUonal Patent Cla-ssfication (IPO or to both national classificaton and I'PC
13. FIELDS SEARCIIED Minimum documentauon searched (classification system followed by classification symbols) IPC 6 C10L CO1M GO1N Documentation searched other than minimum documentation to the extent that such documents arc included in the fields searched Electronic data base consulted during the international search (name of data base and, where practical, search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category Citation of document, with indication, where appropnate, of the relevant passages Relevant to claim No. X DE,A,42 38 994 (BASF) 26 May 1994 1-3,5 cited in the application Y see claims 1,4-6 4 Y EP,A,0 304 613 (BASF) 1 March 1989 4 cited in the application see the whole document Y EP,A,O 236 973 (BASF) 16 September 1987 4 cited in the application see the whole document X FR,A,2 650 606 (AUSSEDAT-REY) 8 February 1991 see claims 1,2,11 SFurther documents are listed in the continuation of box C. [V Patent family members are listed in annex, SSpecial categones of cited documents: later document published after the internatonal filng date or pnonty date and not in conflict with the application but document defning the general state of the art 'hich is not cited to understand the pnnciple or theory underlying the considered to be of particular relevance invention earlier document but published on or after the international 'X document of partcular relevance; the claimed invention filin date cannot be considered novel or cannot be considered to document which may throw doubts on pnonty claim(s) or involve an ivenuve step when the document is taken alone which is cited to establish the publication date of another Y' document of partcular relevance; the claime invention ctation or other special reason (as specified) cannot be considered to involve an inventive step when the document referring to an oral disclosure, use, exhibition o: document is combined with one or more other such docu- other means ments, such combination being obvious to a person skalled document published pnor to the international filing date hut m the art. later than the pnonty date claimed document member of the same patent family Date of the actual completion of the internauonal search Date of mailing of the international search report 21 September 1995
27.09.95. Name and mailing address of the ISA Authonzed officer European Patent Office, P.B. 5818 Patentlaan 2 NL 2280 HV Rlaswilk Tel. (+31-70) 340-2040, Tx. 31 651 epo nl, De La Morinerie B Fax: (+31-70) 340.3l016 Form PCT/ISA/210 (tecond thett) (July 1992) page 1 of 2 INTICRNAE'IONAL S~CARCII I(ICPOWI' PCT/EP 95/02558 (:.((:onunLation) 1POCtM IjN'I*S CO;NSIDIAIthD0 II) KILLIiVAM Category Citation of documecnt, with indication, where appropriate, of thc relevant paSagC% Relevant to claim No. A US,A,5 079 128 (KAZUHARU KATAGIRI, ET AL.) 4 7 January 1992 see column 19 column A US,A,3 930 108 (ALSOP ET AL.) 30 December 4 1975 see the whole document A FR,A,1 450 273 (WARNER-LAM'BERT) 10 4 November 1966 see the whole document A EP,A,0 327 163 (SHELL) 9 August 1989 see page 3, line 19 page 4, line A DATABASE WPI 4 Week 8910 Derwent Publications Ltd., London, GB; AN 89-074228 JP,A,01 028 559 (TERUMO) ,31 January 1989 see abstract I I_ Form PCT/ISA)21O (coninuation of tecond sheet) (July 1992) page 2 of 2 INTERNAI'IONAL SEAIRCH IRPOIRITII' Iitm amol Appnor No Informntion on pawnt lamily incihcs PCT/EP 95/02558 PatLnt document I Publicatiorn Patent (unly Publication cited in search report date member(s) date DE-A-4238994 26-05-94 AU-B- 5464794 08-06-94 CN-A- 1092098 14-09-94 WO-A- 9411466 26-05-94 EP-A- 0669968 06-09-95 FI-A- 952423 18-05-95 NO-A- 951967 18-05-95 EP-A-304613 01-03-89 DE-A- 3724757 09-02-89 JP-A- 1061475 08-03-89 US-A- 4958021 18-09-90 EP-A-236973 16-09-87 OE-A- 3608215 17-09-87 JP-A- 62221682 29-09-87 US-A- 4841050 20-06-89 US-A- 4966983 30-10-90 FR-A-2650606 08-02-91 GB-A,B 2235157 27-02-91 IT-B- 1242789 18-05-94 US-A- 5123999 23-06-92 US-A-5079128 07-01-92 JP-B- 1025717 18-05-89 JP-C- 1543641 15-02-90 JP-A- 58173696 12-10-83 JP-B- 1026356 23-05-89 JP-C- 1543642 15-02-90 JP-A- 58181688 24-10-83 JP-B- 1026357 23-05-89 JP-C- 1543643 15-02-90 JP-A- 58181689 24-10-83 JP-B- 1026358 23-05-89 JP-C- 1543644 15-02-90 JP-A- 58181690 24-10-83 JP-B- 1026879 25-05-89 JP-C- 1739813 15-03-93 JP-A- 58219090 20-12-83 JP-B- 1025718 18-05-89 JP-C- 1543647 15-02-90 JP-A- 58219091 20-12-83 JP-B- 1025714 18-05-89 JP-C- 1543648 15-02-90 Form PCTIIS/210 (patent ranily annex) (July 1992) page 1 of 2 INTERNATUONAL SEIARLCH RI'(UI' ncr IAIApllisriN infor~uon PC/EP 95/02558 Patent document Publication Patent raml Pubication cited in search report daemmbrsT date US-A-5079128 JP-A- 58220792 22-12-83 JP-C- 1587905 19-11-90 JP-B- 2011140 13-03-90 JP-A- 58220143 21-12-83 JP-A- 59014150 25-01-84 US-A- 5320930 14-06-94 US-A- 5382497 17-01-95 US-A- 5079127 07-01-92 US-A- 5278026 11-01-94 US-A- 5246814 21-09-93 US-A-3930108 30-12-75 AU-A- 8657275 19-05-77 BE-A- 835764 16-03-76 DE-A- 2550486 26-05-76 FR-A,B 2291976 18-06-76 JP-A- 51074026 26-06-76 JP-A- 52092618 04-08-77 NL-A- 7513595 25-05-76 FR-A-1450273 10-11-66 NONE EP-A-327163 09-08-89 AT-T- 121192 15-04-95 AU-B- 2894689 03-08-89 OE-0- 68922123 18-05-95 RU-A- 66852 30-01-95 JP-A- 1227059 11-09-89 OA-A- 9230 30-06-92 PT-B- 89572 31-01-94 TR-A- 25397 01-03-93 US-A- 5429952 04-07-95 Form PCTJISA1210 (patent family annex) (July 1992) page 2 of 2 INTICRNMIONAIX4 P CT/EP 95/02558 IPK 6 C1OL1/00 ClOM171/0& GO1N31/22 G01N33/28 C1OL1/18 C1OL1/22 Nach der [nterniatonalcni flatic~awikation (111K) cider nach der nisuon- cn 1 si. l"lkah1nn urid der IPK B. RIICERCFIIP.R'rI GI3DllI'1 Recherchicrter Mindcstprufswtof i Klasifkationaay~tem und Klawxfikalionssymbole) IPK 6 ClOL Cl0ti G01N Recherchicrte aber nicht zumn Mindestprufstofr gehorende Vcroffcniiichunger sowcit dicsc unter die rechcrchiertcn Gebiete fallen Wlihrcnd der intemationalcn Recherce konvuloerte clcktronischc Datenbank (Name der Datenbank und cvti. verwendete Suchbegriffe) C. ALS WESENTLICH ANGESEHIrNE UNTERLAGEN Kategone' Bezeichnung der Veroffcritlichung, soweit erforderhch unter Angabe der in Iletracht kommcndcn Tcile Bar. Anspruch Nr. x OE,A,42 38 994 (BASF) 26.Mai 1994 1-3,5 in der Anmeldung erwdhnt Y siehe AnsprUche 1,4-6 4 Y EP,A,0 304 613 (BASF) 1.M~rz 1989 4 in der Anmeldung erwdhnt siehe das ganze Dokument Y EP,A,Q 236 973 (BASF) 16.September 1987 4 in der Anmeldung erwdhnt siehe das ganze Dokument xFR,A,2 650 606 (AUSSEDAT-REY) 8.Februar 1991 siehe AnsprUche 1,2,11 Weitere Verotfentl:chungen sind dcr Fortsctzung von Feld C zu rv Siehe Arihang Patentfanilic *Besondere Kategonen von angegebenen Verl~ffcntlichungen IT. Spater Verdffentlichung, die reach dem internationaleni Anieededatumn er~fentich chedenallgmemn Stnd er Tchrk deirurtoder dern Pnonti -im verbfcntlicht worden ist Und mit der A Veroffnihehng die rb dens aligetsm and dcer Thi k esnt Anmeldung nicht koi rt, iondemn nur zurnVerstalsdnia des der abernxch alabesoder bedulsa anzsche itErfindung zugrudebeL Icn Prirzips oder der ihr zugrunrdeliegenden dteres Dokument. das jedociS erst am oder nach demn intemnationvalen Theone angegeben itt Artmeld.,datumn verdffentcht worden ist Verboffendichung von besonderer Bcdeuttung; die beansprsichte Erfindung Verdffentchung, die getignet iii, cinen PriortAsanspruch zwetfelhaft er. kann allein aufgrunid dicser VWroffentchung nicht als neu cider auf scheinen zu lassen, cider durch die das Verolfentlichungsdaturn croci- erfindenscher Tdtigkait beruhend betrachtet werden anderen im Recherchenbencht gcnannten Vroffenhlichung becgt Weideil Veroffenhllehung von besonderer Bcdecung; die beanapruchte ErfindunE soil oder die aus; cinemn anderen besondercn Gnind angegeben iSt (Wme kann nicht ala auf erfinderiacher Tahigkerit beruhend bcirachtet atisgefiffhrt) werden, wern die Vcrdffentlichung nut ciner oder mebreren anderen '0 Verdffentlichung, die sich auif cine mhlndlichc Offenbaruing, Veratffenhlichungen dieser Kategoite in Verbindung gebracht wird und elne Elenuizung, elne Ausstellung cider andere Maflnahmen benecht diese Verbindung fur esnen Fachmann nahellegend ist P' Ve~iofetlchung, die vor dem niernatonalen Anineidedatumn, abcr nach Veroffenlichung, die Mitglied dcrsclbcn Patentfaxnilie ist dern teanspruchten Pniontatsdaturn veroffenhiicht worden it Datsun des Absehiusaca der intemnationalen Recherche Absendedatum des tiemratonalen Recherchenbenchts 27-09- 21.Septeniber 1995 Name und Postanschrift der Internationale Rech-"-" hdrdc Bevoilmrachtigter Bediensteter Euroipaisches Patentant, P.B. 581. iv intlaan 2 NL 2280 H-V Rilawilk Tel. (+31.70) 340-2040, Tx 31 651 epo nl,De L o nei, B Faxc (+31-70) 340-3016 D aM rnre Formblstl PCT.'ISA/210 (Blatt 2) (lull 1992) Seite 1 von 2 INTEIRNATriONALEII REICIERCIIENBIERICIIT Inten. ~nalct Aktterzcichcn PCT/EP 95/02558 Vortsctzung) AI.S WESENTLICI ANGESIMIHNL U Nr1MLAGI3N Kategone' Dezeichnung der Veroffendichung, soweit crforderlich unter Angabec der in Ilctracht kornenden Tole BMr. Anspruch Nr. A .S,A,5 079 128 (KAZUHARU KATAGIRI, ET AL.)4 7.Januar 1992 siehe Spalte 19 Spalte A iUS,A,3 930 108 (ALSOr* ET AL.) 30.Oezember 4 I1975 isiehe das ganze Dokument A FR,A,1 450 273 (WARNER-LAMBERT) 4 November 1966 biehe das ganze Dokument A EP,A,0 327 163 (SHELL) 9.August 1989 siehe Seite 3, Zeile 19 Seite 4, Zeile A iDATABASE WPI 4 Week 8910 Derwent Publications Ltd., London, GB; AN 89-074228 JP,A,01 028 559 (TERUMO) 31.Januar I1989 Isiehe Zusammenfassung Fonnblatt PCT'15AMO1 (Fort...g Von Blatt 2) (JUNi 1992) Seite 2 von 2 Angahcri zu Vcr~ffentlichunscii, die zur icdbrm PatcritlArilli ghoreni 1.1 terl OfA1CI Atenchen PCT/EP 95/02558 US-A-5079128 JP-A- 58220792 22-12-83 JP-C- 1587905 19-11-90 JP-B- 2011140 13-03-90 JP-A- 58220143 21-12-83 JP-A- 59014150 25-01-84 US-A- 5320930 14-06-94 US-A- 5382497 17-01-95 US-A- 5079127 07-01-92 US-A- 5278026 11-01-94 US-A- 5246814 21-09-93 US-A-3930108 30-12-75 AU-A- 8657275 19-05-77 BE-A- 835764 16-03-76 OE-A- 2550486 26-05-76 FR-A,B 2291976 18-06-76 JP-A- 51074026 26-06-76 52092618 04-08-77 IL-A- 7513595 25-05-76 FR-A-1450273 10-11-66 KEINE EP-A-327 163 09-08-89 AT-1 AU-B- DE-0- HU-A- ~JP-A- OA-A- PT-B- TR-A- US-A- 121192 2894689 68922123 66852 1227059 9230 89572 25397 5429952 15-04-95 03-08-89 18-05-95
30-01-95 11-09-89 30-06-92 3 1-0 1-94 0 1-03-93 04-07-95 Fcnnblatt PCT/ISA/21 0 (Anthang Patentfarrile)(JuII 1992) Seite 2 von 2 I NTERI~NAION ALI'R IC FC 1NfIIIIi Angabcn zu Vcrollcntlichurigv, dic zur xelhcn PaaltAinilit gdloren I PCT/EP 95/02558 1Im Recherchen bcricht Datum der Mitglicd(cr) Datum der angcftlhrtcs Patcntdakument Vcrofntlichung Patcntfphmalic Veroffendichung IE-A-4238994 26-05-94 AU-B- 5464794 08-06-94 CN-A- 1092098 14-09-94 WO-A- 9411466 26-05-94 EP-A- 0669968 06-09-95 Fl-A- 952423 18-05-95 NO-A- 951967 18-05-95 EP-A-304613 01-03-89 rE-A- 3724757 09-02-89 JP-A- 1061475 08-03-89 US-A- 4958021 18-09-90 EP-A-236973 16-09-87 DE-A- 3 F" 21l5 17-09-87 JP-A- 62221682 29-09-87 US-A- 4841050 20-06-89 US-A- 4966983 30-10-90 FR-A-2650606 08-02-91 GB-A,B 2235157 27-02-91 IT-B- 1242789 18-05-94 US-A- 5123999 23-06-92 US-A-5079128 07-01-92 JP-B- 1025717 18-05-89 LIP-C- 1543641 15-02-90 LIP-A- 58173696 12-10-83 LIP-B- 1026356 23-05-89 LIP-C- 1543642 15-02-90 LIP-A- 58181688 24-10-83 LIP-B- 1026357 23-05-89 LIP-C- 1543643 15-02-90 LIP-A- 58181689 24-10-83 LIP-B- 1026358 23-05-89 LIP-C- 1543644 15-02-90 JP-A- 58181690 24-10-83 LIP-B- 1026879 25-05-89 LIP-C- 1739813 15-03-93 LIP-A- 58219090 20-12-83 LIP-B- 1025718 18-05-89 LIP-C- 1543647 15-02-90 LIP-A- 58219091 20-12-83 LIP-B- 1025714 18-05-89 LIP-C- 1543648 15-02-90 Formblatt PCT/ISA21 0 (Anhang Patentfarnilit)(Jui 1993) Seite 1 von 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4424712A DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
| DE4424712 | 1994-07-13 | ||
| PCT/EP1995/002558 WO1996002613A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
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| AU2926395A AU2926395A (en) | 1996-02-16 |
| AU686838B2 true AU686838B2 (en) | 1998-02-12 |
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| DE19538121C1 (en) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Warp tensioner useful for loom esp. for tension sensitive yarns |
| US7179912B2 (en) | 2000-09-01 | 2007-02-20 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| AU2003227877A1 (en) * | 2002-04-26 | 2003-11-10 | Bp Oil International Limited | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
| EP1660473A2 (en) | 2003-03-24 | 2006-05-31 | Luitpold Pharmaceuticals, Inc. | Xanthones, thioxanthones and acridinones as dna-pk inhibitors |
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
| US9594070B2 (en) * | 2013-11-05 | 2017-03-14 | Spectrum Tracer Services, Llc | Method using halogenated benzoic acid esters and aldehydes for hydraulic fracturing and for tracing petroleum production |
| US10017684B2 (en) | 2016-04-20 | 2018-07-10 | Spectrum Tracer Services, Llc | Method and compositions for hydraulic fracturing and for tracing formation water |
| WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
| EP4327073A1 (en) | 2021-04-20 | 2024-02-28 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0304613A1 (en) * | 1987-07-25 | 1989-03-01 | BASF Aktiengesellschaft | Benzopyran derivatives |
| EP0327163A2 (en) * | 1988-02-02 | 1989-08-09 | Biocode, Inc. | Detection of chemicals by immunoassay |
| FR2650606A1 (en) * | 1989-08-07 | 1991-02-08 | Aussedat Rey | INFALSIFIABLE SAFETY PAPER AND USEFUL AQUEOUS OR ORGANIC COMPOSITION, IN PARTICULAR FOR MAKING INFALSIFIABLE PAPER |
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| FR1450273A (en) * | 1965-10-18 | 1966-05-06 | Warner Lambert Pharmaceutical | Preparation usable for the detection of indole produced by microorganisms |
| US3930108A (en) * | 1974-11-21 | 1975-12-30 | Moore Business Forms Inc | 9-(4-Aminophenyl polymethine)-9-xanthenol compounds and pressure sensitive system therewith |
| US5079127A (en) * | 1982-04-06 | 1992-01-07 | Canon Kabushiki Kaisha | Optical recording medium and process for recording thereupon |
| DE3608215A1 (en) * | 1986-03-12 | 1987-09-17 | Basf Ag | NEW BENZOPYRANS AND THEIR USE IN RECORDING SYSTEMS |
| JPH0630626B2 (en) * | 1987-07-24 | 1994-04-27 | テルモ株式会社 | Indole productivity test reagent |
| DE4238994A1 (en) * | 1992-11-19 | 1994-05-26 | Basf Ag | Aniline as a marking agent for mineral oils |
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1994
- 1994-07-13 DE DE4424712A patent/DE4424712A1/en not_active Withdrawn
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1995
- 1995-07-03 KR KR1019970700194A patent/KR970704860A/en not_active Application Discontinuation
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- 1995-07-03 WO PCT/EP1995/002558 patent/WO1996002613A1/en not_active Application Discontinuation
- 1995-07-03 AU AU29263/95A patent/AU686838B2/en not_active Expired - Fee Related
- 1995-07-03 JP JP8504633A patent/JPH10502693A/en active Pending
- 1995-07-03 HU HU9700062A patent/HUT76687A/en unknown
- 1995-07-03 MX MX9700365A patent/MX9700365A/en unknown
- 1995-07-03 EP EP95924960A patent/EP0770119A1/en not_active Withdrawn
- 1995-07-03 CA CA002195019A patent/CA2195019A1/en not_active Abandoned
- 1995-07-03 CZ CZ9795A patent/CZ9597A3/en unknown
- 1995-07-03 SK SK51-97A patent/SK5197A3/en unknown
- 1995-07-03 BR BR9508401A patent/BR9508401A/en not_active Application Discontinuation
- 1995-07-04 IL IL11444295A patent/IL114442A0/en unknown
- 1995-07-06 TR TR95/00823A patent/TR199500823A2/en unknown
- 1995-07-12 CO CO95030617A patent/CO4600746A1/en unknown
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1997
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- 1997-01-10 FI FI970108A patent/FI970108A/en unknown
- 1997-01-21 BG BG101156A patent/BG101156A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0304613A1 (en) * | 1987-07-25 | 1989-03-01 | BASF Aktiengesellschaft | Benzopyran derivatives |
| EP0327163A2 (en) * | 1988-02-02 | 1989-08-09 | Biocode, Inc. | Detection of chemicals by immunoassay |
| FR2650606A1 (en) * | 1989-08-07 | 1991-02-08 | Aussedat Rey | INFALSIFIABLE SAFETY PAPER AND USEFUL AQUEOUS OR ORGANIC COMPOSITION, IN PARTICULAR FOR MAKING INFALSIFIABLE PAPER |
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| TR199500823A2 (en) | 1996-06-21 |
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| BR9508401A (en) | 1998-05-19 |
| EP0770119A1 (en) | 1997-05-02 |
| SK5197A3 (en) | 1997-08-06 |
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