WO1996002613A1 - Werwendung von benzaldehyden zum markieren von kohlenwasserstoffen - Google Patents
Werwendung von benzaldehyden zum markieren von kohlenwasserstoffen Download PDFInfo
- Publication number
- WO1996002613A1 WO1996002613A1 PCT/EP1995/002558 EP9502558W WO9602613A1 WO 1996002613 A1 WO1996002613 A1 WO 1996002613A1 EP 9502558 W EP9502558 W EP 9502558W WO 9602613 A1 WO9602613 A1 WO 9602613A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- alkyl
- benzaldehydes
- radical
- hydrogen
- Prior art date
Links
- 150000003935 benzaldehydes Chemical class 0.000 title claims abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 28
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 239000003550 marker Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- -1 1,4-butylene Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 150000002475 indoles Chemical class 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 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
- 125000004663 dialkyl amino group Chemical group 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
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 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
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 5
- 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
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-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
- 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
- 238000002372 labelling Methods 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
- 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 244000172533 Viola sororia Species 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
- 230000002349 favourable effect Effects 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 239000000203 mixture Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 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
- 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
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
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- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 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
- 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
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- 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
- 239000000446 fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 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 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 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 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 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
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- 150000002576 ketones Chemical class 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 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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- 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
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- 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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- 235000005985 organic acids Nutrition 0.000 description 1
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- 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
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
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- 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
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C10L1/2235—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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- C10L1/2286—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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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
- C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
Definitions
- the present invention relates to the use of benzaldehyde of the formula I.
- ring A can be fused to benzo
- R 1 , R 2 and R 3 each independently represent hydrogen, hydroxyl, C_-C_ 5- alkyl, Ci-Cis-alkoxy, cyano, nitro or a radical of the formula NR 4 R 5 or COOR 6 , in which
- R 4 is hydrogen or Ci-Cis-alkyl, which is by 1 to
- oxygen atoms can be interrupted in ether function and is optionally substituted by phenyl
- R 5 for C 1 -C 5 alkyl which can be interrupted by 1 to 4 oxygen atoms in ether function and is optionally substituted by phenyl, or a radical of the formula L-NX i X 2 , in which L has the meaning of C 2 -C ⁇ - Alkylene and X 1 and X 2 independently of one another each have the meaning of Ci-C ⁇ -alkyl or, together with the nitrogen atom connecting them, the meaning of a 5- or 6-membered saturated heterocyclic radical which also has an oxygen atom in the ring may contain, own, and
- R 6 for hydrogen, C_-Ci 5 alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function, or for a radical of the formula L-NX X X 2 , where L, X 1 and X 2 each have the above meaning, as a marking agent for hydrocarbons, a method for the detection of these benzaldehydes in hydrocarbons and hydrocarbons, containing the above-mentioned benzaldehydes.
- Azo dyes which serve as marking agents for mineral oils are already known from US Pat. No. 5,145,573, US Pat. No. 5,182,372 and EP-A-499 845.
- US Pat. No. 4,009,008 describes a method for marking mineral oils using disazo dyes, in which the dye added to the mineral oil is made visible by adding an adsorbent to the marked mineral oil that binds other colored components of the mineral oil .
- DE-A-3 608 215 and DE-A-3 724 757 describe benzopyran derivatives and their use in recording systems.
- Example 1 of DE-A-3 608 215 is the reaction of 2,3-dimethylbenzopyrylium trichlorozincate with 4-dimethylaminobenzaldehyde in methanol to form the color salt of the formula
- WO-A-11 466/1994 describes the use of substituted anilines for marking mineral oils.
- the object of the present invention was to provide new means for marking hydrocarbons.
- the new agents should be easily accessible and readily soluble in hydrocarbons.
- should 'they can be detected in a simple manner. Even very small amounts of marking material should be made visible by a strong color reaction.
- All alkyl and alkylene radicals occurring in the above-mentioned formula I can be either straight-chain or branched. If X 1 and X 2 together with the nitrogen atom connecting them represent a 5- or 6-membered saturated heterocyclic radical which may also contain an oxygen atom in the ring, then pyrrolidinyl, piperidinyl or morpholinyl can be considered .
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , ⁇ i and X 2 are, 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 are, for example, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, ündecyl, dodecyl, tridecyl, 3,5,5 , 7-tetramethylnonyl, isotride ⁇ cyl, tetradecyl or pentadecyl (the above terms isoctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the alcohols obtained after oxosynthesis - see also Üllmann's Encyclopedia of Industrial Chemistry, 5th Edition , Vol. AI, pages 290 to 293, and vol. A 10, pages 284 and 285).
- R 1 , R 2 and R 3 are furthermore, 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, isodecyloxy, undecyloxy, dodecyloxy, tridecyloxy, 3,5, 5,7-tetramethylnonyloxy, isotridecyloxy, tetradecyloxy or pentadecyloxy.
- R 4 and R 5 are furthermore, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3- Propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxy-butyl, 2- or 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,
- L are, for example, (CH 2 ) 2 , (CH 2 ) 3 , (CH 2 ) 4 , (CH 2 ) 5 , (CH 2 ) 6 , (CH 2 ) 7 , (CH 2 ) 8 , CH (CH 3 ) CH 2 or CH (CH 3 ) CH (CH 3 ).
- benzaldehydes of the formula I in which at least one of the radicals R 1 to R 3 is a radical of the formula NRR 5 , in which R 4 and R 5 each have the abovementioned meaning.
- Benzaldehydes of the formula la are particularly preferred
- R 1 , R 2 , R 4 and R 5 each have the abovementioned meaning, used for marking hydrocarbons.
- Benzaldehydes of the formula Ia in which R 4 and R 5 independently of one another are each C 1 -C 3 -alkyl, and R 1 and R 2 are each hydrogen, are particularly preferably used for marking hydrocarbons.
- the invention also relates to a method for detecting the presence of benzaldehydes of the formula I in hydrocarbons, the hydrocarbon being treated with an aqueous-alcoholic or alcoholic medium which is a protonic acid, at least one compound from the group of Compounds consisting of substituted benzopyrylium salts of formula II
- R 7 is Ci-C ⁇ -alkyl, phenyl, Ci-Cs-alkoxy or halogen and R ⁇ for methyl or R 7 and R 8 together represent 1,4-butylene and the ring B can be fused by a benzene ring and if appropriate by C ⁇ -C 4 alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 possibly also by hydroxy, C. -C ⁇ alkoxy, Ci-Cs-mono- or dialkylamino, which in turn can be substituted by chlorine or phenyl, is substituted and ® means any anion, and indoles of the formula III
- R 9 and R 10 independently of one another each represent hydrogen, hydroxy, a radical of the formula NR 4 R 5 , in which R 4 and R 5 each have the abovementioned meaning, Ci-C ⁇ -alkyl, phenyl, Ci-Cs-alkoxy or Halogen stand,
- indoles of the formula III preference is given to using indoles of the formula III, in particular 2-phenylindole.
- Suitable anions X® are tetrachlorozincate, halide, sulfate, tetrafluoroborate or phosphate.
- the benzaldehydes I, the benzopyrylium salts II and the indoles III are generally known per se.
- Labeling in the sense of the invention means an addition of the benzaldehydes of the formula I to hydrocarbons in such a concentration that the hydrocarbons are either not colored at all or only slightly visible to the human eye, but the benzaldehydes of the formula I can be easily and clearly detected by the detection methods described in more detail here.
- the present invention further provides hydrocarbons containing one or more of the benzaldehydes of the formula I.
- Hydrocarbons in the sense of the invention are understood to mean aliphatic or aromatic hydrocarbons which are present in the liquid state under normal conditions.
- These are in particular mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils, such as heating oil or engine oil.
- the benzaldehydes of the formula I are particularly suitable for marking mineral oils for which labeling is required, for example for tax reasons. To reduce the cost of To keep this low, the aim is to use the smallest possible amount of marking agent for the marking.
- the benzaldehydes of the formula I are used either in bulk or in the form of solutions.
- Organic solvents are suitable as solvents.
- Aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics, which is commercially available under the name Shellsol® AB (Shell), are preferably used.
- Shellsol® AB Shellsol® AB
- a concentration of benzaldehydes I of 5 to 80% by weight, based on the solution, is generally chosen.
- Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol
- glycols such as butyl ethylene glycol or methyl propylene 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 3-
- aqueous alcoholic or alcoholic medium which is a pyrylium salt of the formula II and / or an indole of the formula III, a protonic acid and optionally a halide of the metals zinc, aluminum or tin.
- aqueous-alcoholic media the weight ratio water: alcohol is 0.5: 1 to 4: 1, preferably about 1: 1.
- Suitable alcohols are, for example, ethanol, propanol, isopropanol, l-methoxypropan-2-ol, ethylene glycol or 1,2- or 1,3-propylene glycol. The use of ethanol is preferred.
- Suitable protonic acids for the processes according to the invention are in particular so-called strong acids, i.e. Protonic acids whose pKa is ⁇ .3.5.
- strong acids i.e. Protonic acids whose pKa is ⁇ .3.5.
- examples of such acids are 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 , Dichloroacetic acid or bromoacetic acid. In some cases it may be advantageous to use these acids e.g. by adding acetic acid.
- Suitable halides of the metals zinc, aluminum or tin are e.g. Zinc chloride, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride. Zinc chloride is particularly noteworthy.
- the concentration of the protonic acid in the aqueous-alcoholic or alcoholic solution is usually 5 to 50% by weight, preferably 10 to 30% by weight.
- the concentration of metal halide is generally 0 to 50% by weight, preferably 5 to 20% by weight, in each case based on the weight of the solution.
- a great advantage of the invention is that two different methods for the detection of the benzaldehydes of the formula I can be used.
- the detection can therefore also be carried out very reliably in the event of possible interference (for example additives in diesel fuel).
- possible interference for example additives in diesel fuel.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX9700365A MX9700365A (es) | 1994-07-13 | 1995-07-03 | Uso de benzaldehidos para asignar hidrocarburos. |
| BR9508401A BR9508401A (pt) | 1994-07-13 | 1995-07-03 | Uso de benzaldeídos processo de detecção de benzaldeídos e hidrocarboneto com um marcador |
| AU29263/95A AU686838B2 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| JP8504633A JPH10502693A (ja) | 1994-07-13 | 1995-07-03 | 炭化水素をマーキングするためのベンズアルデヒドの使用 |
| EP95924960A EP0770119A1 (de) | 1994-07-13 | 1995-07-03 | Werwendung von benzaldehyden zum markieren von kohlenwasserstoffen |
| SK51-97A SK5197A3 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde derivative to mark hydrocarbons, proofing method for the benzaldehyde derivative presence in hydrocarbons and hydrocarbons containing the benzaldehyde derivative |
| KR1019970700194A KR970704860A (ko) | 1994-07-13 | 1995-07-03 | 탄화 수소 표지용 벤즈알데히드의 용도 |
| FI970108A FI970108A (fi) | 1994-07-13 | 1997-01-10 | Bentsaldehydien käyttö hiilivetyjen merkitsemiseen |
| NO970126A NO970126L (no) | 1994-07-13 | 1997-01-10 | Anvendelse av benzaldhyder for markering av hydrokarboner |
| BG101156A BG101156A (en) | 1994-07-13 | 1997-01-21 | Use of benzaldehydes to mark hydrocarbons |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4424712A DE4424712A1 (de) | 1994-07-13 | 1994-07-13 | Verwendung von Benzaldehyden zum Markieren von Kohlenwasserstoffen |
| DEP4424712.5 | 1994-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996002613A1 true WO1996002613A1 (de) | 1996-02-01 |
Family
ID=6523046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/002558 WO1996002613A1 (de) | 1994-07-13 | 1995-07-03 | Werwendung von benzaldehyden zum markieren von kohlenwasserstoffen |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0770119A1 (xx) |
| JP (1) | JPH10502693A (xx) |
| KR (1) | KR970704860A (xx) |
| AU (1) | AU686838B2 (xx) |
| BG (1) | BG101156A (xx) |
| BR (1) | BR9508401A (xx) |
| CA (1) | CA2195019A1 (xx) |
| CO (1) | CO4600746A1 (xx) |
| CZ (1) | CZ9597A3 (xx) |
| DE (1) | DE4424712A1 (xx) |
| FI (1) | FI970108A (xx) |
| HU (1) | HUT76687A (xx) |
| IL (1) | IL114442A0 (xx) |
| MX (1) | MX9700365A (xx) |
| NO (1) | NO970126L (xx) |
| PL (1) | PL318378A1 (xx) |
| SK (1) | SK5197A3 (xx) |
| TR (1) | TR199500823A2 (xx) |
| WO (1) | WO1996002613A1 (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
| WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
| WO2022223384A1 (en) | 2021-04-20 | 2022-10-27 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19538121C1 (de) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Ungesteuerte Spanneinheit für die Webkette einer Webmaschine |
| 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 |
| 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 |
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| JPS6428559A (en) * | 1987-07-24 | 1989-01-31 | Terumo Corp | Reagent for inspection of indole production capacity |
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| DE4238994A1 (de) * | 1992-11-19 | 1994-05-26 | Basf Ag | Aniline als Markierungsmittel für Mineralöle |
-
1994
- 1994-07-13 DE DE4424712A patent/DE4424712A1/de not_active Withdrawn
-
1995
- 1995-07-03 KR KR1019970700194A patent/KR970704860A/ko not_active Application Discontinuation
- 1995-07-03 PL PL95318378A patent/PL318378A1/xx unknown
- 1995-07-03 WO PCT/EP1995/002558 patent/WO1996002613A1/de 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/ja active Pending
- 1995-07-03 HU HU9700062A patent/HUT76687A/hu unknown
- 1995-07-03 MX MX9700365A patent/MX9700365A/es unknown
- 1995-07-03 EP EP95924960A patent/EP0770119A1/de not_active Withdrawn
- 1995-07-03 CA CA002195019A patent/CA2195019A1/en not_active Abandoned
- 1995-07-03 CZ CZ9795A patent/CZ9597A3/cs unknown
- 1995-07-03 SK SK51-97A patent/SK5197A3/sk unknown
- 1995-07-03 BR BR9508401A patent/BR9508401A/pt not_active Application Discontinuation
- 1995-07-04 IL IL11444295A patent/IL114442A0/xx unknown
- 1995-07-06 TR TR95/00823A patent/TR199500823A2/xx unknown
- 1995-07-12 CO CO95030617A patent/CO4600746A1/es unknown
-
1997
- 1997-01-10 NO NO970126A patent/NO970126L/no unknown
- 1997-01-10 FI FI970108A patent/FI970108A/fi unknown
- 1997-01-21 BG BG101156A patent/BG101156A/xx unknown
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| FR1450273A (fr) * | 1965-10-18 | 1966-05-06 | Warner Lambert Pharmaceutical | Préparation utilisable pour la recherche de l'indole produit par les microorganismes |
| US3930108A (en) * | 1974-11-21 | 1975-12-30 | Moore Business Forms Inc | 9-(4-Aminophenyl polymethine)-9-xanthenol compounds and pressure sensitive system therewith |
| US5079128A (en) * | 1982-04-06 | 1992-01-07 | Canon Kabushiki Kaisha | Optical recording medium and process for recording thereupon |
| EP0236973A2 (de) * | 1986-03-12 | 1987-09-16 | BASF Aktiengesellschaft | Neue Benzypyrane und deren Verwendung in Aufzeichnungssystemen |
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| EP0327163A2 (en) * | 1988-02-02 | 1989-08-09 | Biocode, Inc. | Detection of chemicals by immunoassay |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
| WO2014083186A2 (en) * | 2012-11-30 | 2014-06-05 | Inter-Euro Technology Limited | Improved fuel markers |
| WO2014083186A3 (en) * | 2012-11-30 | 2014-09-12 | Inter-Euro Technology Limited | Improved fuel markers |
| WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
| WO2022223384A1 (en) | 2021-04-20 | 2022-10-27 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2926395A (en) | 1996-02-16 |
| CA2195019A1 (en) | 1996-02-01 |
| TR199500823A2 (tr) | 1996-06-21 |
| NO970126D0 (no) | 1997-01-10 |
| CO4600746A1 (es) | 1998-05-08 |
| FI970108A0 (fi) | 1997-01-10 |
| MX9700365A (es) | 1997-04-30 |
| IL114442A0 (en) | 1995-11-27 |
| AU686838B2 (en) | 1998-02-12 |
| PL318378A1 (en) | 1997-06-09 |
| CZ9597A3 (en) | 1997-06-11 |
| BG101156A (en) | 1997-08-29 |
| JPH10502693A (ja) | 1998-03-10 |
| KR970704860A (ko) | 1997-09-06 |
| FI970108A (fi) | 1997-03-12 |
| DE4424712A1 (de) | 1996-01-18 |
| HUT76687A (en) | 1997-10-28 |
| NO970126L (no) | 1997-03-10 |
| BR9508401A (pt) | 1998-05-19 |
| EP0770119A1 (de) | 1997-05-02 |
| SK5197A3 (en) | 1997-08-06 |
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