WO1996002613A1 - Use of benzaldehydes to mark hydrocarbons - Google Patents
Use of benzaldehydes to mark hydrocarbons 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
- 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
- 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
- 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
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006184 cosolvent 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
- 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
- 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
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- 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
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- 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
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- 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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Abstract
The invention relates to the use of benzaldehydes of the formula (I), in which ring A can be benzo-anellated and R?1, R2 and R3¿ are hydrogen, hydroxy, C¿1?-C15 alkyl, C1-C15 alkoxy, cyano, nitro or a radical of the formula NR?4R5¿ or COOR6, in which R4 is hydrogen or possibly substituted C¿1?-C15 alkyl, R?5¿ is possibly substituted C¿1?-C15 alkyl or a radical of the formula L-NX?1X2¿, in which L is C¿2?-C8 alkylene and X?1 and X2¿ are mutually independently C¿1?-C6 alkyl or, together with the nitrogen atom bonding them, a heterocyclic radical, and R?6¿ is hydrogen, possibly substituted C¿1?-C15 alkyl or a radical of the formula L-NX?1X2¿, in which L, X?1 and X2¿ have the above meanings, as marking agents for hydrocarbons, a process for detecting these benzaldehydes in hydrocarbons and hydrocarbons containing the above benzaldehydes.
Description
Verwendung von Benzaldehyden zum Markieren von Kohlenwasser¬ stoffenUse of benzaldehydes for marking hydrocarbons
Beschreibungdescription
Die vorliegende Erfindung betrifft die Verwendung von Benz¬ aldehyden der Formel IThe present invention relates to the use of benzaldehyde of the formula I.
in derin the
der Ring A benzoanelliert sein kann,ring A can be fused to benzo
R1, R2 und R3 unabhängig voneinander jeweils Wasserstoff, Hydroxy, C_-C_5-Alkyl, Ci-Cis-Alkoxy, Cyano, Nitro oder einen Rest der Formel NR4R5 oder COOR6 bedeuten, worinR 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
R4 für Wasserstoff oder Ci-Cis-Alkyl, das durch 1 bisR 4 is hydrogen or Ci-Cis-alkyl, which is by 1 to
4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch Phenyl substituiert ist,4 oxygen atoms can be interrupted in ether function and is optionally substituted by phenyl,
R5 für Cι-C_5-Alkyl, das durch 1 bis 4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch Phenyl substituiert ist, oder einen Rest der Formel L-NXiX2, worin L die Bedeutung von C2-Cβ-Alkylen und X1 und X2 unabhängig voneinander jeweils die Bedeutung von Ci-Cβ-Älkyl oder zusammen mit dem sie verbindenden Stick¬ stoffatom die Bedeutung eines 5- oder 6-gliedrigen ge¬ sättigten heterocyclischen Rests, der noch ein Sauer¬ stoffatom im Ring enthalten kann, besitzen, undR 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 -Cβ- Alkylene and X 1 and X 2 independently of one another each have the meaning of Ci-Cβ-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
R6 für Wasserstoff, C_-Ci5-Alkyl, das durch 1 bis 4 Sauer- stoffatome in Etherfunktion unterbrochen sein kann, oder für einen Rest der Formel L-NXXX2, worin L, X1 und X2 je¬ weils die obengenannte Bedeutung besitzen, stehen,
als Markierungsmittel für Kohlenwasserstoffe, ein Verfahren zum Nachweis dieser Benzaldehyde in Kohlenwasserstoffen sowie Kohlen¬ wasserstoffe, enthaltend die obengenannten Benzaldehyde.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.
Aus der US-A-5 145 573, US-A-5 182 372 sowie der EP-A-499 845 sind bereits Azofarbstoffe bekannt, die als Markierungsmittel für Mineralöle dienen. In der US-A-4 009 008 wird weiterhin ein Ver¬ fahren zum Markieren von Mineralölen mittels Disazofarbstoffen beschrieben, bei dem man den dem Mineralöl zugesetzten Farbstoff sichtbar macht, indem man ein Adsorptionsmittel dem markierten Mineralöl zusetzt, das andere farbige Bestandteile des Mineralöls bindet .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 .
In der DE-A-3 608 215 und der DE-A-3 724 757 sind Benzopyranderi- vate sowie deren Verwendung in AufZeichnungssystemen beschrieben.DE-A-3 608 215 and DE-A-3 724 757 describe benzopyran derivatives and their use in recording systems.
Im Beispiel 1 der DE-A-3 608 215 ist die Umsetzung von 2,3-Di- methylbenzopyrylium-trichlorozinkat mit 4-Dimethylaminobenzal- dehyd in Methanol unter Bildung des Farbsalzes der FormelExample 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
beschrieben.described.
In der WO-A-11 466/1994 ist die Verwendung von substituierten Anilinen zum Markieren von Mineralölen beschrieben.WO-A-11 466/1994 describes the use of substituted anilines for marking mineral oils.
Aufgabe der vorliegenden Erfindung war es, neue Mittel zum Mar¬ kieren von Kohlenwasserstoffen bereitzustellen. Die neuen Mittel sollten leicht zugänglich und gut in Kohlenwasserstoffen löslich sein. Außerdem' sollten sie in einfacher Weise nachgewiesen werden können. Dabei sollten selbst noch sehr kleine Mengen an Markier¬ stoff durch eine starke Farbreaktion sichtbar gemacht werden können.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. In addition, 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.
Demgemäß wurde gefunden, daß sich die eingangs näher bezeichneten Benzaldehyde der Formel I vorteilhaft als Markierungsmittel für Kohlenwasserstoffe eignen.Accordingly, it has been found that the benzaldehydes of the formula I described at the outset are advantageously suitable as marking agents for hydrocarbons.
Alle in der obengenannten Formel I auftretenden Alkyl- und Alkylenreste können sowohl geradkettig als auch verzweigt sein.
Wenn X1 und X2 zusammen mit dem sie verbindenden Stickstoffatom einen 5- oder 6-gliedrigen gesättigten heterocyclischen Rest, der noch ein Sauerstoffatom im Ring enthalten kann, bedeuten, so kön¬ nen dafür z.B. Pyrrolidinyl, Piperidinyl oder Morpholinyl in Be- tracht kommen.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 .
Reste R1, R2, R3, R4, R5, R6, χi und X2 sind z.B. Methyl, Ethyl, Propyl, Isopropyl, Butyl, Isobutyl, sec-Butyl, Pentyl, Isopen- tyl, Neopentyl, tert-Pentyl, Hexyl oder 2-Methylpentyl.R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , χi and X 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert -Pentyl, hexyl or 2-methylpentyl.
Reste R1, R2, R3, R4, R5 und R6 sind weiterhin z.B. Heptyl, Octyl, 2-Ethylhexyl, Isooctyl, Nonyl, Isononyl, Decyl, Isodecyl, ündecyl, Dodecyl, Tridecyl, 3,5,5,7-Tetramethylnonyl, Isotride¬ cyl, Tetradecyl oder Pentadecyl (die obigen Bezeichnungen Iso- octyl, Isononyl, Isodecyl und Isotridecyl sind Trivialbezeichnun¬ gen und stammen von den nach der Oxosynthese erhaltenen Alkoholen - vgl. dazu Üllmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. AI, Seiten 290 bis 293, sowie Vol. A 10, Seiten 284 und 285) .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).
Reste R1, R2 und R3 sind weiterhin z.B. Methoxy, Ethoxy, Propoxy, Isopropoxy, Butoxy, Isobutoxy, sec-Butoxy, Pentyloxy, Isopentyl- oxy, Neopentyloxy, tert-Pentyloxy, Hexyloxy, 2-Methylpentyloxy, Heptyloxy, Octyloxy, 2-Ethylhexyloxy, Isooctyloxy, Nonyloxy, Iso- nonyloxy, Decyloxy, Isodecyloxy, Undecyloxy, Dodecyloxy, Tride- cyloxy, 3,5, 5,7-Tetramethylnonyloxy, Isotridecyloxy, Tetradecyl- oxy oder Pentadecyloxy.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.
Reste R4 und R5 sind weiterhin z.B. 2-Methoxyethyl, 2-Ethoxyethyl, 2-Propoxyethyl, 2-Isopropoxyethyl, 2-Butoxyethyl, 2- oder 3-Meth- oxypropyl, 2- oder 3-Ethoxypropyl, 2- oder 3-Propoxypropyl, 2- oder 3-Butoxypropyl, 2- oder 4-Methoxybutyl, 2- oder 4-Ethoxy- butyl, 2- oder 4-Propoxybutyl, 2- oder 4-Butoxybutyl, 3,6-Dioxa- heptyl, 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-Tetraoxatri- decyl, Benzyl oder 1- oder 2-Phenylethyl.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, 6,9-trioxaundecyl, 3, 6, 9,12-tetraoxatridecyl, benzyl or 1- or 2-phenylethyl.
Reste L sind z.B. (CH2)2, (CH2)3, (CH2)4, (CH2)5, (CH2)6, (CH2)7, (CH2)8, CH(CH3)CH2 oder CH(CH3)CH(CH3) .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 ).
Erfindungsgemäß bevorzugt werden Benzaldehyde der Formel I verwendet, bei denen mindestens einer der Reste R1 bis R3 einen Rest der Formel NRR5 bedeutet, worin R4 und R5 jeweils die oben- genannte Bedeutung besitzen.
Besonders bevorzugt werden Benzaldehyde der Formel laAccording to the invention, preference is given to using 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
in der R1, R2, R4 und R5 jeweils die obengenannte Bedeutung besit¬ zen, zum Markieren von Kohlenwasserstoffen verwendet.in which R 1 , R 2 , R 4 and R 5 each have the abovementioned meaning, used for marking hydrocarbons.
Besonders geeignet sind Benzaldehyde der Formel la, in der R1 und R2 unabhängig voneinander jeweils Wasserstoff, Hydroxy,Benzaldehydes of the formula Ia in which R 1 and R 2 are each independently of one another hydrogen, hydroxy,
Cl-Cis-Alkyl, Ci-Cis-Alkoxy oder einen Rest der Formel COOR6, worin R6 die obengenannte Bedeutung besitzt, R4 Wasserstoff oder Ci-Cis-Alkyl und R5 Cι-C_5-Alkyl bedeuten.Cl-Cis-alkyl, Ci-Cis-alkoxy or a radical of the formula COOR 6 , in which R 6 has the abovementioned meaning, R 4 is hydrogen or Ci-Cis-alkyl and R 5 is C 1 -C 5 -alkyl.
Besonders bevorzugt werden Benzaldehyde der Formel la, in der R4 und R5 unabhängig voneinander jeweils Cχ-Cι3-Alkyl, sowie R1 und R2 jeweils Wasserstoff bedeuten, zum Markieren von Kohlenwasserstof¬ fen verwendet.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.
Gegenstand der Erfindung ist außerdem ein Verfahren zum Nachweis der Anwesenheit von Benzaldehyden der Formel I in Kohlenwasser¬ stoffen, wobei man den Kohlenwasserstoff mit einem wäßrig-alkoho¬ lischen oder alkoholischen Medium behandelt, das eine Proton¬ säure, mindestens eine Verbindung aus der Gruppe der Verbindun- gen, bestehend aus substituierten Benzopyryliumsalzen der For¬ mel IIThe 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
in der R7 für Ci-Cβ-Alkyl, Phenyl, Ci-Cs-Alkoxy oder Halogen und Rβ für Methyl oder R7 und R8 zusammen für 1,4-Butylen stehen und der Ring B durch einen Benzolring anelliert sein kann und gegebenen¬ falls durch Cι-C4-Alkyl, Pyrrolidino, Piperidino, Morpholino, Chlor oder Brom oder in Ringposition 7 gegebenenfalls auch durch Hydroxy, C.-C^-Alkoxy, Ci-Cs-Mono- oder Dialkylamino, das jeweils wiederum durch Chlor oder Phenyl substituiert sein kann, substi- tuiert ist und ® ein beliebiges Anion bedeutet, und Indolen der Formel III
in which R 7 is Ci-Cβ-alkyl, phenyl, Ci-Cs-alkoxy or halogen and R β 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 Cι-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
in der R9 und R10 unabhängig voneinander jeweils für Wasserstoff, Hydroxy, einen Rest der Formel NR4R5, worin R4 und R5 jeweils die obengenannte Bedeutung besitzen, Ci-Cβ-Alkyl, Phenyl, Ci-Cs-Alkoxy oder Halogen stehen,in which 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-Cβ-alkyl, phenyl, Ci-Cs-alkoxy or Halogen stand,
und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder Zinn enthält.and optionally containing a halide of the metals zinc, aluminum or tin.
Bevorzugt werden erfindungsgemäß Indole der Formel III, ins¬ besondere 2-Phenylindol, verwendet.According to the invention, preference is given to using indoles of the formula III, in particular 2-phenylindole.
Beispiele für geeignete Anionen X® sind Tetrachlorozinkat, Halo- genid, Sulfat, Tetrafluoroborat oder Phosphat.Examples of suitable anions X® are tetrachlorozincate, halide, sulfate, tetrafluoroborate or phosphate.
Die Benzaldehyde I, die Benzopyryliumsalze II sowie die In¬ dole III sind in der Regel an sich bekannt.The benzaldehydes I, the benzopyrylium salts II and the indoles III are generally known per se.
Unter Markierung im erfindungsgemäßen Sinn ist ein Zusatz der Benzaldehyde der Formel I in solcher Konzentration zu Kohlenwas¬ serstoffen zu verstehen, daß die Kohlenwasserstoffe dadurch für das menschliche Auge entweder überhaupt nicht oder nur wenig sichtbar angefärbt sind, wobei jedoch die Benzaldehyde der For- mel I durch die hier näher beschriebenen Nachweismethoden leicht und deutlich sichtbar detektierbar sind.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.
Ein weiterer Gegenstand der vorliegenden Erfindung sind Kohlen¬ wasserstoffe, enthaltend einen oder mehrere der Benzaldehyde der Formel I.The present invention further provides hydrocarbons containing one or more of the benzaldehydes of the formula I.
Unter Kohlenwasserstoffen im erfindungsgemäßen Sinn sind alipha- tische oder aromatische Kohlenwasserstoffe zu verstehen, die unter Normalbedingungen in flüssigem Aggregatzustand vorliegen. Dies sind insbesondere Mineralöle, beispielsweise Treibstoffe, wie Benzin, Kerosin oder Dieselöl, oder Öle, wie Heizöl oder Mo¬ torenöl.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.
Die Benzaldehyde der Formel I eignen sich insbesondere zum Mar- kieren von Mineralölen, bei denen eine Kennzeichnung gefordert wird, z.B. aus steuerlichen Gründen. Um die Kosten der Kennzeich-
nung gering zu halten, strebt man dabei an, für die Markierung möglichst geringe Mengen an Markierungsmittel anzuwenden.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.
Zum Markieren von Kohlenwasserstoffen werden die Benzaldehyde der Formel I entweder in Substanz oder in Form von Lösungen ange¬ wandt. Als Lösungsmittel eignen sich organische Lösungsmittel. Vorzugsweise kommen aromatische Kohlenwasserstoffe, wie Toluol, Xylol, Dodecylbenzol, Diisopropylnaphthalin oder ein Gemisch hö¬ herer Aromaten, das unter dem Namen Shellsol® AB (Fa. Shell) han- delsüblich ist, zur Anwendung. Um eine hohe Viskosität der resul¬ tierenden Lösungen zu vermeiden, wählt man im allgemeinen eine Konzentration an Benzaldehyden I von 5 bis 80 Gew.-%, bezogen auf die Lösung.To mark hydrocarbons, 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. In order to avoid a high viscosity of the resulting solutions, a concentration of benzaldehydes I of 5 to 80% by weight, based on the solution, is generally chosen.
Zur Verbesserung der Löslichkeit können auch noch weitere Cosol- ventien, z.B. Alkohole, wie Methanol, Ethanol, Propanol, Iso- propanol, Butanol, Isobutanol, Pentanol, Hexanol, Heptanol, Octanol, 2-Ethylhexanol oder Cyclohexanol, Glykole, wie Butyl- ethylenglykol oder Methylpropylenglykol, Amine, wie Triethylamin, Diisooctylamin, Dicyclohexylamin, Anilin, N-Methylanilin, N,N-Di- methylanilin, Toluidin oder Xylidin, Alkanolamine, wie 3-(2-Meth- oxyethoxy)propylamin, o-Kresol, m-Kresol oder p-Kresol, Ketone, wie Diethylketon oder Cyclohexanon, Lactame, wie γ-Butyrolacton, Carbonate, wie Ethylencarbonat oder Propylencarbonat, Phenole, wie t-Butylphenol oder Nonylphenol, Ester, wie Phthalsäuremethyl- ester, Phthalsäureethylester, Phthalsäure- (2-ethylhexyl)ester, Essigsäureethylester, Essigsäurebutylester oder Essigsäurecyclo- hexylester, Amide, wie N,N-Dimethylformamid, N,N-Diethylacetamid oder N-Methylpyrrolidinon, oder deren Mischungen verwendet wer- den.To improve solubility, other cosolvents, e.g. 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 γ-butyrolactone, carbonates, such as ethylene 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 amyl acetate, cyclohexyl acetate , such as N, N-dimethylformamide, N, N-diethylacetamide or N-methylpyrrolidinone, or mixtures thereof.
Mittels den erfindungsgemäß anzuwendenden Benzaldehyden der For¬ mel I gelingt es sehr einfach, markierte Kohlenwasserstoffe nach¬ zuweisen, selbst wenn die Markierungssubstanzen nur in einer Kon- zentration von ungefähr 10 ppm oder darunter vorliegen.Using the benzaldehydes of formula I to be used according to the invention, it is very easy to detect labeled hydrocarbons, even if the labeling substances are only present in a concentration of approximately 10 ppm or less.
Der Nachweis der Anwesenheit der als Markierungsstoffe angewand¬ ten Verbindungen der Formel I in Kohlenwasserstoffen gelingt vor¬ teilhaft, wenn man den Kohlenwasserstoff mit einem wäßrig-alkoho- lischen oder alkoholischem Medium behandelt, das ein Pyryliumsalz der Formel II und/oder ein Indol der Formel III, eine Protonsäure und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder Zinn enthält. Bei der Verwendung von wäßrig-alkoholischen Medien beträgt das Gewichtsverhältnis Wasser : Alkohol 0,5 : 1 bis 4 : 1, vorzugsweise ca. 1:1. Es resultiert eine deutlich sicht¬ bare Farbänderung der wäßrig-alkoholischen Phase.
Geeignete Alkohole sind z.B. Ethanol, Propanol, Isopropanol, l-Methoxypropan-2-ol, Ethylenglykol oder 1,2- oder 1,3-Propylen- glykol. Die Verwendung von Ethanol ist bevorzugt.The presence of the compounds of the formula I used as markers in hydrocarbons can be advantageously achieved if the hydrocarbon is treated with an 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. When using aqueous-alcoholic media, the weight ratio water: alcohol is 0.5: 1 to 4: 1, preferably about 1: 1. The result is a clearly visible change in color of the aqueous-alcoholic phase. 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.
Geeignete Protonsäuren für die erfindungsgemäßen Verfahren sind insbesondere sogenannte starke Säuren, d.h. Protonsäuren deren pKa-Wert <.3,5 ist. Als solche Säuren kommen beispielsweise anor¬ ganische oder organische Säuren, wie Perchlorsäure, Iodwasser- stoffsäure, Chlorwasserstoffsäure, Bromwasserstoffsäure, Fluß- säure, Schwefelsäure, Salpetersäure, Phosphorsäure, Benzolsulfon- säure, Toluolsulfonsäure, Naphthalinsulfonsäure, Methansulfon- säure, Oxalsäure, Maleinsäure, Chloressigsäure, Dichloressigsäure oder Bromessigsäure in Betracht. In manchen Fällen kann es von Vorteil sein, diese Säuren, z.B. durch Zugabe von Essigsäure, ab- zupuffern.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. 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.
Neben o- oder p-Toluolsulfonsäure sind besonders anorganische Säuren hervorzuheben, wobei Salzsäure oder Schwefelsäure beson¬ dere Bedeutung zukommt.In addition to o- or p-toluenesulfonic acid, particular emphasis should be given to inorganic acids, hydrochloric acid or sulfuric acid being of particular importance.
Geeignete Halogenide der Metalle Zink, Aluminium oder Zinn sind z.B. Zinkchlorid, Zinkbromid, Aluminiumchlorid, Aluminiumbromid oder Zinntetrachlorid. Besonders hervorzuheben ist Zinkchlorid.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.
Es genügt in der Regel, eine Menge von ungefähr 10 bis 50 ml des erfindungsgemäß markierten Kohlenwasserstoffs mit 1 bis 50 ml einer wäßrig-alkoholischen oder alkoholischen Lösung eines Pyry- liumsalzes der Formel II und/oder eines Indols der Formel III, einer Protonsäure, gegebenenfalls unter Zusatz des Metallhaloge- nids, auszuschütteln, um eine Farbänderung zu erhalten. Es ist auch möglich, anstelle der Lösung der Protonsäure eine wäßrig-al¬ koholische Lösung des Metallhalogenids alleine zu benutzen, da diese ebenfalls sauer reagiert.It is usually sufficient to add about 10 to 50 ml of the hydrocarbon labeled according to the invention with 1 to 50 ml of an aqueous-alcoholic or alcoholic solution of a pyramid salt of the formula II and / or an indole of the formula III, a protonic acid, if appropriate with the addition of the metal halide, to obtain a color change. It is also possible to use an aqueous alcoholic solution of the metal halide alone instead of the solution of the protonic acid, since this also reacts acidically.
Die Konzentration der Protonsäure in der wäßrig-alkoholischen oder alkoholischen Lösung beträgt dabei in der Regel 5 bis 50 Gew.-%, vorzugsweise 10 bis 30 Gew.-%. Die Konzentration an Metallhalogenid liegt im allgemeinen bei 0 bis 50 Gew.-%, vor¬ zugsweise bei 5 bis 20 Gew.-%, jeweils bezogen auf das Gewicht der Lösung.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.
Ein großer Vorteil der Erfindung besteht darin, daß zwei ver¬ schiedene Methoden zum Nachweis der Benzaldehyde der Formel I be¬ nutzt werden können. Der Nachweis kann daher auch bei möglichen Störeinflüssen (z.B. Zusätze in Dieselkraftstoff) sehr zuverläs¬ sig durchgeführt werden.
Die folgenden Beispiele sollen die Erfindung näher erläutern.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). The following examples are intended to explain the invention in more detail.
Allgemeine Vorschrift 1:General rule 1:
Handelsüblicher Dieselkraftstoff wurde mit jeweils 10 ppm eines Benzaldehyds versetzt. Hierzu wurde der Aldehyd 0,1 gew.-%ig in Toluol vorgelöst und diese Lösung zum Dieselkraftstoff gegeben.Commercial diesel fuel was mixed with 10 ppm each of a benzaldehyde. For this purpose, the 0.1% by weight aldehyde was predissolved in toluene and this solution was added to the diesel fuel.
In den folgenden Beispielen 1 bis 12 wurden jeweils 10 ml so mar- kierten Dieselkraftstoffes mit 2 ml Reagenzlösung versetzt und 5 Minuten geschüttelt. Anschließend wurde 1 ml Wasser zugegeben und weitere 5 Minuten geschüttelt. Die wässrige Phase zeigte die in der folgenden Tabelle Nr. 1 angegebenen Farbe.In Examples 1 to 12 below, 10 ml of diesel fuel marked in this way were mixed with 2 ml of reagent solution and shaken for 5 minutes. Then 1 ml of water was added and shaken for a further 5 minutes. The aqueous phase showed the color given in the following Table No. 1.
Reagenzlösung 1Reagent solution 1
5 ml 1 gew.-%ig Indol in Ethanol 5 ml Salzsäure konz. 5 g Zinkchlorid 95 ml Essigsäure5 ml 1 wt .-% indole in ethanol 5 ml hydrochloric acid conc. 5 g zinc chloride 95 ml acetic acid
Reagenzlösung 2Reagent solution 2
5 ml 1 gew.-%ig 2-Methylindol in Ethanol 5 ml Salzsäure konz. 5 g Zinkchlorid 95 ml Essigsäure5 ml 1 wt .-% 2-methyl indole in ethanol 5 ml hydrochloric acid conc. 5 g zinc chloride 95 ml acetic acid
Reagenzlösung 3Reagent solution 3
5 ml 1 gew.-%ig 2-Phenylindol in Ethanol 5 ml Salzsäure konz. 5 g Zinkchlorid 95 ml Essigsäure5 ml 1 wt .-% 2-phenylindole in ethanol 5 ml hydrochloric acid conc. 5 g zinc chloride 95 ml acetic acid
Besonders vorteilhafte Ergebnisse werden erhalten, wenn der Die¬ selkraftstoff zuerst über Kieselgel filtriert wird.
Tabelle Nr . 1Particularly advantageous results are obtained when the diesel fuel is first filtered through silica gel. Table number 1
Bsp. Nr, Aldehyd Reagenz Farbe magentaExample No., aldehyde reagent color magenta
N(CH3)2 N (CH 3 ) 2
violettviolet
N(CH3)2 N (CH 3 ) 2
violettviolet
N(CH3)2 N (CH 3 ) 2
orangeorange
N(C2HS)2 N (C 2 H S ) 2
rot-violettred-violet
N(C2H5)2
Bsp. Nr Aldehyd Reagenz Farbe magentaN (C 2 H 5 ) 2 Example No. Aldehyde reagent color magenta
N(C2H5)2 N (C 2 H 5 ) 2
CHO orangeCHO orange
rot-violettred-violet
magentamagenta
10 rot-violett10 red-violet
N(CH3)2
Bsp. Nr. Aldehyd Reagenz FarbeN (CH 3 ) 2 Ex. No. Aldehyde reagent color
11 2 blau-violett11 2 blue-violet
12 3 blau-violett12 3 blue-violet
Ähnlich günstige Ergebnisse werden erzielt, wenn man die in der folgenden Tabelle Nr. 2 aufgeführten Benzaldehyde als Markie¬ rungsmittel anwendet.Similar favorable results are achieved if the benzaldehydes listed in the following Table No. 2 are used as markers.
Tabelle Nr. 2Table No. 2
Bsp. Nr. AldehydEx. No. aldehyde
1313
1414
Handelsüblicher Dieselkraftstoff wurde mit jeweils 10 ppm Benzal¬ dehyd versetzt. Hierzu wurde der Benzaldehyd 0,1 gew.-%ig in Toluol vorgelöst und diese Lösung zum Dieselkraftstoff gegeben.Commercial diesel fuel was mixed with 10 ppm each of benzaldehyde. For this purpose, the benzaldehyde was pre-dissolved 0.1% by weight in toluene and this solution was added to the diesel fuel.
In den Beispielen 21 bis 30 wurden jeweils 10 ml des markierten Dieselkraftstoffes mit 2 ml Reagenzlösung 4 versetzt und 5 Minu¬ ten unter Rückfluß erhitzt. Anschließend wurde 1 ml Wasser/Etha- nol (1:1 v/v) zugegeben und 5 Minuten geschüttelt. Die wässrige Phase zeigte die in der folgenden Tabelle Nr. 3 angegebene Farbe.In Examples 21 to 30, 10 ml of the marked diesel fuel were mixed with 2 ml of reagent solution 4 and heated under reflux for 5 minutes. Then 1 ml of water / ethanol (1: 1 v / v) was added and shaken for 5 minutes. The aqueous phase showed the color given in the following Table No. 3.
Reagenzlösung 4Reagent solution 4
5 ml Benzopyryliumsalz der Formel5 ml of benzopyrylium salt of the formula
1 gew.-%ig in Wasser 25 ml Salzsäure konz. 225 ml Essigsäure1 wt .-% in water 25 ml hydrochloric acid conc. 225 ml acetic acid
Tabelle 3Table 3
Bsp. Nr. Aldehyd Q FarbeExample No.Aldehyde Q color
21 C6H5 blau21 C 6 H 5 blue
N(CH3)2 N (CH 3 ) 2
22 CH3 blau22 CH 3 blue
28 CH3 rot-violett28 CH 3 red-violet
29 CH3 rot-violett29 CH 3 red-violet
30 CH3 violett30 CH 3 purple
CHOCHO
OCH3 OCH 3
Ähnlich günstige Ergebnisse werden erzielt, wenn man das in Reagenzlösung 4 enthaltene Benzopyryliumsalz durch das der FormelSimilar favorable results are achieved if the benzopyrylium salt contained in reagent solution 4 is compared to that of the formula
ersetzt.
replaced.
Claims
1. Verwendung von Benzaldehyden der Formel I1. Use of benzaldehydes of the formula I
R-R-
in derin the
der Ring A benzoanelliert sein kann undthe ring A can be fused to benzo and
R1, R2 und R3 unabhängig voneinander jeweils Wasserstoff, Hydroxy, Cι-C_5-Alkyl, Cχ-Ci5-Alkoxy, Cyano, Nitro oder einen Rest der Formel NR4R5 oder COOR6 bedeuten, worinR 1 , R 2 and R 3 independently of one another are each hydrogen, hydroxy, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, cyano, nitro or a radical of the formula NR 4 R 5 or COOR 6 , in which
R4 für Wasserstoff oder Cχ-Ci5-Alkyl, das durch 1 bisR 4 for hydrogen or Cχ-Ci 5 alkyl, which by 1 to
4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch Phenyl substituiert ist,4 oxygen atoms can be interrupted in ether function and is optionally substituted by phenyl,
R5 für Ci-Cis-Alkyl, das durch 1 bis 4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebe¬ nenfalls durch Phenyl substituiert ist, oder einen Rest der Formel L-NXi-X2, worin L die Bedeutung vonR 5 is Ci-Cis-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 is the meaning of
C2-C8 _Alkylen und X1 und X2 unabhängig voneinander jeweils die Bedeutung von Ci-Cβ-Alkyl oder zusammen mit dem sie verbindenden Stickstoffatom die Bedeutung eines 5- oder 6-gliedrigen gesättigten heterocycli- sehen Rests, der noch ein Sauerstoffatom im Ring ent¬ halten kann, besitzen, undC 2 -C 8 _ alkylene and X 1 and X 2 independently of one another each have the meaning of Ci-Cβ-alkyl or together with the nitrogen atom connecting them the meaning of a 5- or 6-membered saturated heterocyclic radical which still has an oxygen atom ent can contain, and
R6 für Wasserstoff, C_-C_s-Alkyl, das durch 1 bisR 6 for hydrogen, C_-C_s-alkyl, which is represented by 1 to
4 Sauerstoffatome in Etherfunktion unterbrochen sein kann, oder für einen Rest der Formel L-NXLX2, worin4 oxygen atoms can be interrupted in ether function, or for a radical of the formula L-NX L X 2 , wherein
L, X1 und X2 jeweils die obengenannte Bedeutung be¬ sitzen, stehen,L, X 1 and X 2 each have the above-mentioned meaning,
als Markierungsmittel für Kohlenwasserstoffe. as a marking agent for hydrocarbons.
2. Verwendung von Benzaldehyden nach Anspruch 1, dadurch gekenn¬ zeichnet, daß die Benzaldehyde der Formel la2. Use of benzaldehydes according to claim 1, characterized gekenn¬ characterized in that the benzaldehydes of the formula la
entsprechen, in der R1, R2, R4 und R5 jeweils die in An¬ spruch 1 genannte Bedeutung besitzen.correspond in which R 1 , R 2 , R 4 and R 5 each have the meaning given in claim 1.
3. Verwendung von Benzaldehyden nach den Ansprüchen 1 oder 2, dadurch gekennzeichnet, daß R1 und R2 unabhängig voneinander jeweils Wasserstoff, Hydroxy, C_-C_5-Alkyl, Ci-Cis-Alkoxy oder einen Rest der Formel COOR6, worin R6 die in Anspruch 1 ge¬ nannte Bedeutung besitzt, R4 Wasserstoff oder Ci-Cis-Alkyl und R5 Ci-Cis-Alkyl bedeuten.3. Use of benzaldehydes according to claims 1 or 2, characterized in that R 1 and R 2 independently of one another are each hydrogen, hydroxyl, C_-C_ 5- alkyl, Ci-Cis-alkoxy or a radical of the formula COOR 6 , wherein R 6 has the meaning given in claim 1, R 4 is hydrogen or Ci-Cis-alkyl and R 5 Ci-Cis-alkyl.
4. Verfahren zum Nachweis der Anwesenheit von Benzaldehyden der Formel I gemäß Anspruch 1 in Kohlenwasserstoffen, dadurch ge¬ kennzeichnet, daß man den Kohlenwasserstoff mit einem wäßrig- alkoholischen oder alkoholischen Medium behandelt, das eine Protonsäure, mindestens eine Verbindung aus der Gruppe der Verbindungen, bestehend aus substituierten Pyryliumsalzen der Formel II4. A method for the detection of the presence of benzaldehydes of the formula I as claimed in claim 1 in hydrocarbons, characterized in that the hydrocarbon is treated with an aqueous-alcoholic or alcoholic medium which is a protonic acid, at least one compound from the group of the compounds, consisting of substituted pyrylium salts of formula II
in der R7 für C_-C_-Alkyl, Phenyl, Ci-Cs-Alkoxy oder Halogen und R8 für Methyl oder R7 und R8 zusammen für 1,4-Butylen ste¬ hen und der Ring B durch einen Benzolring anelliert sein kann und gegebenenfalls durch Ci-C^-Alkyl, Pyrrolidino, Piperidino, Morpholino, Chlor oder Brom oder in Ringposition 7 gegebenen- falls auch durch Hydroxy, Cχ-C<j-Alkoxy, Ci-Cs-Mono- oderin which R 7 is C_-C_-alkyl, phenyl, Ci-Cs-alkoxy or halogen and R 8 for methyl or R 7 and R 8 together represent 1,4-butylene and ring B is fused by a benzene ring can and optionally by Ci-C ^ alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 if necessary also by hydroxy, Cχ-C <j-alkoxy, Ci-Cs-mono- or
Dialkylamino, das jeweils wiederum durch Chlor oder Phenyl substituiert sein kann, substituiert ist und X® ein beliebi¬ ges Anion bedeutet, und Indolen der Formel III 
Dialkylamino, which in turn can be substituted by chlorine or phenyl, is substituted and X® is any anion, and indoles of the formula III
in der R9 und R10 unabhängig voneinander jeweils für Wasser¬ stoff Hydroxy, einen Rest der Formel NR4R5, worin R4 und R5 jeweils die in Anspruch 1 genannte Bedeutung besitzen, Ci-Ca-Alkyl, Phenyl, Ci-Cs-Alkoxy oder Halogen stehen,in which R 9 and R 10 independently of one another each represent hydrogen, a radical of the formula NR 4 R 5 , in which R 4 and R 5 each have the meaning given in Claim 1, Ci-Ca-alkyl, phenyl, Ci Are Cs-alkoxy or halogen,
und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder Zinn enthält.and optionally containing a halide of the metals zinc, aluminum or tin.
Kohlenwasserstoffe, enthaltend als Markierungsmittel einen oder mehrere Benzaldehyde der Formel I gemäß Anspruch 1. Hydrocarbons containing one or more benzaldehydes of the formula I as claimed in claim 1 as the marking agent.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| AU29263/95A AU686838B2 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| KR1019970700194A KR970704860A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde for hydrocarbon labeling |
| JP8504633A JPH10502693A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde to mark hydrocarbons |
| MX9700365A MX9700365A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons. |
| BR9508401A BR9508401A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes benzaldehyde and hydrocarbon detection process with a marker |
| EP95924960A EP0770119A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| NO970126A NO970126L (en) | 1994-07-13 | 1997-01-10 | Use of benzal hydrocarbons for marking hydrocarbons |
| FI970108A FI970108A (en) | 1994-07-13 | 1997-01-10 | Use of benzaldehydes for the labeling of hydrocarbons |
| 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 |
|---|---|---|---|
| DEP4424712.5 | 1994-07-13 | ||
| DE4424712A DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996002613A1 true WO1996002613A1 (en) | 1996-02-01 |
Family
ID=6523046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/002558 WO1996002613A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0770119A1 (en) |
| JP (1) | JPH10502693A (en) |
| KR (1) | KR970704860A (en) |
| AU (1) | AU686838B2 (en) |
| BG (1) | BG101156A (en) |
| BR (1) | BR9508401A (en) |
| CA (1) | CA2195019A1 (en) |
| CO (1) | CO4600746A1 (en) |
| CZ (1) | CZ9597A3 (en) |
| DE (1) | DE4424712A1 (en) |
| FI (1) | FI970108A (en) |
| HU (1) | HUT76687A (en) |
| IL (1) | IL114442A0 (en) |
| MX (1) | MX9700365A (en) |
| NO (1) | NO970126L (en) |
| PL (1) | PL318378A1 (en) |
| SK (1) | SK5197A3 (en) |
| TR (1) | TR199500823A2 (en) |
| WO (1) | WO1996002613A1 (en) |
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 (en) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Warp tensioner useful for loom esp. for tension sensitive yarns |
| AU2001288432A1 (en) | 2000-09-01 | 2002-03-22 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| US20050103686A1 (en) * | 2002-04-26 | 2005-05-19 | Taylor Spencer E. | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
| CA2523178C (en) | 2003-03-24 | 2012-10-23 | Luitpold Pharmaceuticals, Inc. | Materials and methods to potentiate cancer treatment |
| 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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-
1994
- 1994-07-13 DE DE4424712A patent/DE4424712A1/en not_active Withdrawn
-
1995
- 1995-07-03 MX MX9700365A patent/MX9700365A/en unknown
- 1995-07-03 CA CA002195019A patent/CA2195019A1/en not_active Abandoned
- 1995-07-03 EP EP95924960A patent/EP0770119A1/en not_active Withdrawn
- 1995-07-03 KR KR1019970700194A patent/KR970704860A/en not_active Application Discontinuation
- 1995-07-03 BR BR9508401A patent/BR9508401A/en not_active Application Discontinuation
- 1995-07-03 SK SK51-97A patent/SK5197A3/en unknown
- 1995-07-03 HU HU9700062A patent/HUT76687A/en unknown
- 1995-07-03 PL PL95318378A patent/PL318378A1/en unknown
- 1995-07-03 CZ CZ9795A patent/CZ9597A3/en unknown
- 1995-07-03 AU AU29263/95A patent/AU686838B2/en not_active Expired - Fee Related
- 1995-07-03 WO PCT/EP1995/002558 patent/WO1996002613A1/en not_active Application Discontinuation
- 1995-07-03 JP JP8504633A patent/JPH10502693A/en active Pending
- 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
-
1997
- 1997-01-10 NO NO970126A patent/NO970126L/en unknown
- 1997-01-10 FI FI970108A patent/FI970108A/en unknown
- 1997-01-21 BG BG101156A patent/BG101156A/en unknown
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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 |
| US5079128A (en) * | 1982-04-06 | 1992-01-07 | Canon Kabushiki Kaisha | Optical recording medium and process for recording thereupon |
| EP0236973A2 (en) * | 1986-03-12 | 1987-09-16 | BASF Aktiengesellschaft | Benzopyranes and their use in a recording system |
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| 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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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 |
|---|---|
| CZ9597A3 (en) | 1997-06-11 |
| MX9700365A (en) | 1997-04-30 |
| FI970108A (en) | 1997-03-12 |
| HUT76687A (en) | 1997-10-28 |
| NO970126D0 (en) | 1997-01-10 |
| NO970126L (en) | 1997-03-10 |
| CO4600746A1 (en) | 1998-05-08 |
| PL318378A1 (en) | 1997-06-09 |
| EP0770119A1 (en) | 1997-05-02 |
| SK5197A3 (en) | 1997-08-06 |
| FI970108A0 (en) | 1997-01-10 |
| JPH10502693A (en) | 1998-03-10 |
| CA2195019A1 (en) | 1996-02-01 |
| TR199500823A2 (en) | 1996-06-21 |
| IL114442A0 (en) | 1995-11-27 |
| DE4424712A1 (en) | 1996-01-18 |
| BG101156A (en) | 1997-08-29 |
| AU2926395A (en) | 1996-02-16 |
| AU686838B2 (en) | 1998-02-12 |
| KR970704860A (en) | 1997-09-06 |
| BR9508401A (en) | 1998-05-19 |
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