WO1996000271A1 - Verwendung von carbonylverbindungen zum markieren von kohlenwasserstoffen - Google Patents
Verwendung von carbonylverbindungen zum markieren von kohlenwasserstoffen Download PDFInfo
- Publication number
- WO1996000271A1 WO1996000271A1 PCT/EP1995/002330 EP9502330W WO9600271A1 WO 1996000271 A1 WO1996000271 A1 WO 1996000271A1 EP 9502330 W EP9502330 W EP 9502330W WO 9600271 A1 WO9600271 A1 WO 9600271A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrocarbons
- carbonyl compounds
- alkyl
- formula
- hydrogen
- Prior art date
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 43
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 43
- 150000001728 carbonyl compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000003550 marker Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002372 labelling Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 239000002283 diesel fuel Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000001273 butane Substances 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003502 gasoline Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003915 liquefied petroleum gas Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- 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
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-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
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 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
- 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
- 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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 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
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy Chemical group 0.000 description 1
- 239000002480 mineral oil Substances 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
- 239000010705 motor oil Substances 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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
- 238000011896 sensitive detection Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1857—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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Definitions
- the present invention relates to the use of carbonyl compounds for labeling hydrocarbons, hydrocarbons containing carbonyl compounds as labeling agents, and to a method for detecting carbonyl compounds in hydrocarbons.
- hydrocarbons e.g. Products from the refining of petroleum
- heating oil is usually marked, since it is taxed much less than that which is identical in composition to diesel oil.
- Suitable marking agents for hydrocarbons should in particular
- the object of the present invention was to provide new marking agents for liquid or liquefiable by compression hydrocarbons. Such markers should be readily available and have the property profile mentioned above. 2
- R 1 is hydrogen, -C 4 alkyl, -C 4 alkoxy or a radical of the formula
- X is a direct bond
- oxygen or imino and Z 1 and Z 2 are each independently hydrogen, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -alkoxy or halogen,
- R 2 is hydrogen, -CC 4 alkyl or a radical of the formula
- R 3 is hydrogen, hydroxy, -CC 4 alkyl or -CC 4 alkoxy and
- L 1 and L 2 each independently represent hydrogen, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen and
- the ring A can be benzo-fused, advantageously for labeling hydrocarbons.
- R 1 , R 2 , R 3 , L 1 , L 2 , Z 1 and Z 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
- R 1 , R 3 , L 1 , L 2 , Z 1 and Z 2 are, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy.
- L 1 , L 2 , Z 1 and Z 2 are, for example, fluorine, chlorine or bromine.
- Labeling in the sense of the invention means an addition of the carbonyl compounds of the formula I and / or II to hydrocarbons, the hydrocarbons thereby not being visible to the human eye, but the carbonyl compounds of the formula I and / or II being changed by the here Detection methods described in more detail are easily and clearly visible.
- Hydrocarbons in the sense of the invention are generally understood to mean products such as are obtained in the refining of petroleum. These are e.g. Propane, butane, pentane, hexane, heptane, octane, isooctane, benzene, toluene, xylene, ethylbenzene, tetralin, decalin or dimethylnaphthalene.
- these are mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils, such as heating oil or motor oil.
- this also includes products such as those used for processing certain types of plants, e.g. Rape or sunflowers. Such products are also known under the term "bio-diesel”.
- the hydrocarbons are generally in the liquid state under normal conditions or are in the gaseous state and are e.g. by compression, liquefiable, e.g. Liquefied petroleum gas, such as propane or butane.
- Carbonyl compounds of the formula I are preferably used, in which R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or a radical of the formula
- Z 1 and Z 2 each have the meaning given above, and R 2 is C ⁇ -C-alkyl, as a marking agent.
- the carbonyl compounds of the formula I and / or II 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
- alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol
- glycols such as butylethylene glycol or methylpropylene glycol
- amines such as triethylamine, diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N, N-dimethylaniline, toluidine or xylidine
- alkanolamines such as 3- (2-methoxyethoxy) propylamine, o-cresol, m-cresol, p-cresol, ketones , such as diethyl ketone or cyclohexanone, lactones such as ⁇ -buty
- the hydrocarbons preferably have a content of 5 to 1000 ppm, in particular 10 to 1000 ppm, of marking agent. Particularly noteworthy is a content of 10 to 500 ppm, in particular 50 to 100 ppm.
- the hydrocarbons can also contain other labeling or denaturing agents known per se, such as furfural or C.I. Solvent Red 198 included.
- carbonyl compounds of the above formulas I and / or II can advantageously be detected in hydrocarbons if the hydrocarbons are treated with an aqueous-alcoholic or aqueous-acetone solution of an iron (III) salt.
- Suitable iron (III) salts are e.g. Iron (I ⁇ I) halides, such as iron (III) chloride or iron (III) bromide, iron (III) sulfate, iron (III) nitrate or iron (III) acetate.
- Iron (I ⁇ I) halides such as iron (III) chloride or iron (III) bromide, iron (III) sulfate, iron (III) nitrate or iron (III) acetate.
- ferric chloride is preferred.
- the iron (III) salts are used in an aqueous-alcoholic or aqueous-acetone solution.
- the use of an aqueous-alcoholic solution is preferred.
- Suitable alcohols for the preparation of the aqueous-alcoholic solution are e.g. Methanol, ethanol, propanol or isopropanol.
- Methanol e.g. Methanol, ethanol, propanol or isopropanol.
- methanol or ethanol is preferred, the use of methanol being particularly noteworthy.
- suitable reagent solutions generally have a content of 0.05 to 0.5% by weight, preferably 0.1 to 0.3% by weight, iron (III) salts, 10 up to 90% by weight, preferably 40 to 70% by weight, of an alcohol or acetone and 10 to 90% by weight, preferably 30 to 60% by weight, Water, the total of the components of course giving 100 wt .-%.
- the detection is usually carried out by vigorously shaking about 20 ml of labeled hydrocarbon with about 2 ml of reagent solution for about 15 to 20 seconds.
- the phase is allowed to separate.
- the lower aqueous phase has a red or violet-brown color. The color depends on the type of marking agent.
- the content of the marking agent can be determined by methods known per se, e.g. by means of spectroscopic methods.
- the detection is usually carried out in such a way that in a suitable container, e.g. a test tube, 1 to 2 ml of reagent solution and then drains the liquefied hydrocarbon from a gas bottle containing the liquefied hydrocarbon for about 15 to 30 seconds and collects it in the container.
- a suitable container e.g. a test tube
- the hydrocarbon escape from the lying bottle, since in this case it will generally still emerge in the liquid state.
- the liquefied hydrocarbon is allowed to evaporate.
- the reagent solution In the presence of the carbonyl compounds of the formula I and / or II, the reagent solution then has a red or violet-brown color.
- Example 1 was carried out with unmarked liquid gas.
- the reagent was yellow in color.
- Example 2 The test described in Example 1 was repeated. The reagent was clearly purple in color.
- Example 5 20 ml of diesel oil marked with 50 ppm acetylacetone were placed in a separatory funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was shaken vigorously for 20 seconds. They were then allowed to sit down. The phases separated after 5 minutes. The lower aqueous phase was clearly red in color.
- Example 5 20 ml of diesel oil marked with 50 ppm acetylacetone were placed in a separatory funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was shaken vigorously for 20 seconds. They were then allowed to sit down. The phases separated after 5 minutes. The lower aqueous phase was clearly red in color. Example 5
- Example 4 1 ml of the labeled diesel oil from Example 4 was diluted with 9 ml of unlabeled diesel oil. The procedure described in Example 4 was repeated with this mixture. The lower aqueous phase was slightly red in color.
- Example 4 The procedure described in Example 4 was carried out with 20 ml of unlabeled diesel oil. The lower aqueous phase remained yellow.
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- Food Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (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)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paper (AREA)
- Fats And Perfumes (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR9508104A BR9508104A (pt) | 1994-06-24 | 1995-06-16 | Uso de composto de carbonila hidrocarboneto e processo para detectar composto de carbonila |
| MX9700119A MX9700119A (es) | 1994-06-24 | 1995-06-16 | Uso de compuestos de carbonilo como marcadores para hidrocarburos. |
| AU27928/95A AU2792895A (en) | 1994-06-24 | 1995-06-16 | Use of carbonyl compounds for marking hydrocarbons |
| JP8502759A JPH10502111A (ja) | 1994-06-24 | 1995-06-16 | 炭化水素の標識のためのカルボニル化合物の使用 |
| PL95317941A PL317941A1 (en) | 1994-06-24 | 1995-06-16 | Application od carbonyl compounds for labelling hydrocarbons |
| EP95923333A EP0766724A1 (de) | 1994-06-24 | 1995-06-16 | Verwendung von carbonylverbindungen zum markieren von kohlenwasserstoffen |
| NO965554A NO965554L (no) | 1994-06-24 | 1996-12-23 | Anvendelse av karbonylforbindelser for markering av hydrokarboner |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI941320A IT1269947B (it) | 1994-06-24 | 1994-06-24 | Composizione marcante-denaturante particolarmente adatta per marcare e denaturare combustibili |
| ITMI94A001320 | 1994-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996000271A1 true WO1996000271A1 (de) | 1996-01-04 |
Family
ID=11369163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/002330 WO1996000271A1 (de) | 1994-06-24 | 1995-06-16 | Verwendung von carbonylverbindungen zum markieren von kohlenwasserstoffen |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0766724A1 (no) |
| JP (1) | JPH10502111A (no) |
| AU (1) | AU2792895A (no) |
| BR (1) | BR9508104A (no) |
| CA (1) | CA2193886A1 (no) |
| CO (1) | CO4410389A1 (no) |
| CZ (1) | CZ379296A3 (no) |
| HU (1) | HUT76753A (no) |
| IL (1) | IL114195A0 (no) |
| IT (1) | IT1269947B (no) |
| MX (1) | MX9700119A (no) |
| NO (1) | NO965554L (no) |
| PL (1) | PL317941A1 (no) |
| WO (1) | WO1996000271A1 (no) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1010978A1 (fr) * | 1998-12-16 | 2000-06-21 | Total Raffinage Distribution S.A. | Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2971254B1 (fr) * | 2011-02-08 | 2014-05-30 | Total Raffinage Marketing | Compositions liquides pour marquer les carburants et combustibles hydrocarbones liquides, carburants et combustibles les contenant et procede de detection des marqueurs |
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB287192A (en) * | 1926-10-25 | 1928-03-22 | British Dyestuffs Corp Ltd | Improvements in and relating to fuels for internal combustion engines |
| GB473653A (en) * | 1936-04-15 | 1937-10-15 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of carbon compounds of high molecularweight |
| US2205408A (en) * | 1938-08-09 | 1940-06-25 | Gen Aniline & Film Corp | Fluorescent hydrocarbon oil |
| US3508875A (en) * | 1967-10-03 | 1970-04-28 | Union Oil Co | Method for tracing the flow of water in subterranean formations |
| DE2111370A1 (de) * | 1970-03-11 | 1971-09-23 | Acna | Verfahren zum Farben von aus der Erdoeldestillation stammenden Kohlenwasserstoffen und Farbstoffloesungen zur Durchfuehrung des Verfahrens |
| EP0310319A2 (en) * | 1987-09-28 | 1989-04-05 | Acna Chimica Organica S.P.A. | Use of alkyl (C1-C4)-phenyl-ketone for marking oil products and organic solvents |
| EP0327163A2 (en) * | 1988-02-02 | 1989-08-09 | Biocode, Inc. | Detection of chemicals by immunoassay |
| FR2650606A1 (fr) * | 1989-08-07 | 1991-02-08 | Aussedat Rey | Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable |
| WO1993016149A1 (de) * | 1992-02-14 | 1993-08-19 | Basf Italia S.P.A. | Metallsalze als markierungsmittel für brennbitumen |
| EP0565715A1 (en) * | 1990-04-26 | 1993-10-20 | Yoshibi, Co., Ltd. | Liquefied gas fuel for generating highly luminous colored flame |
-
1994
- 1994-06-24 IT ITMI941320A patent/IT1269947B/it active IP Right Grant
-
1995
- 1995-06-16 WO PCT/EP1995/002330 patent/WO1996000271A1/de not_active Application Discontinuation
- 1995-06-16 CA CA002193886A patent/CA2193886A1/en not_active Abandoned
- 1995-06-16 EP EP95923333A patent/EP0766724A1/de not_active Withdrawn
- 1995-06-16 IL IL11419595A patent/IL114195A0/xx unknown
- 1995-06-16 JP JP8502759A patent/JPH10502111A/ja active Pending
- 1995-06-16 PL PL95317941A patent/PL317941A1/xx unknown
- 1995-06-16 BR BR9508104A patent/BR9508104A/pt not_active Application Discontinuation
- 1995-06-16 CZ CZ963792A patent/CZ379296A3/cs unknown
- 1995-06-16 HU HU9603550A patent/HUT76753A/hu unknown
- 1995-06-16 AU AU27928/95A patent/AU2792895A/en not_active Abandoned
- 1995-06-16 MX MX9700119A patent/MX9700119A/es unknown
- 1995-06-22 CO CO95027629A patent/CO4410389A1/es unknown
-
1996
- 1996-12-23 NO NO965554A patent/NO965554L/no unknown
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB287192A (en) * | 1926-10-25 | 1928-03-22 | British Dyestuffs Corp Ltd | Improvements in and relating to fuels for internal combustion engines |
| GB473653A (en) * | 1936-04-15 | 1937-10-15 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of carbon compounds of high molecularweight |
| US2205408A (en) * | 1938-08-09 | 1940-06-25 | Gen Aniline & Film Corp | Fluorescent hydrocarbon oil |
| US3508875A (en) * | 1967-10-03 | 1970-04-28 | Union Oil Co | Method for tracing the flow of water in subterranean formations |
| DE2111370A1 (de) * | 1970-03-11 | 1971-09-23 | Acna | Verfahren zum Farben von aus der Erdoeldestillation stammenden Kohlenwasserstoffen und Farbstoffloesungen zur Durchfuehrung des Verfahrens |
| EP0310319A2 (en) * | 1987-09-28 | 1989-04-05 | Acna Chimica Organica S.P.A. | Use of alkyl (C1-C4)-phenyl-ketone for marking oil products and organic solvents |
| EP0327163A2 (en) * | 1988-02-02 | 1989-08-09 | Biocode, Inc. | Detection of chemicals by immunoassay |
| FR2650606A1 (fr) * | 1989-08-07 | 1991-02-08 | Aussedat Rey | Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable |
| EP0565715A1 (en) * | 1990-04-26 | 1993-10-20 | Yoshibi, Co., Ltd. | Liquefied gas fuel for generating highly luminous colored flame |
| WO1993016149A1 (de) * | 1992-02-14 | 1993-08-19 | Basf Italia S.P.A. | Metallsalze als markierungsmittel für brennbitumen |
Non-Patent Citations (1)
| Title |
|---|
| WINDHOLZ ET AL.: "THE MERCK INDEX", MERCK & CO., RAHWAY,N.J.,U.S.A. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1010978A1 (fr) * | 1998-12-16 | 2000-06-21 | Total Raffinage Distribution S.A. | Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures |
| FR2787577A1 (fr) * | 1998-12-16 | 2000-06-23 | Total Raffinage Distribution | Indicateur colore pour la mesure de la repartition des familles d'hydrocarbures contenues dans un melange, son procede d'obtention et ses utilisations |
| US6451615B1 (en) | 1998-12-16 | 2002-09-17 | Total Raffinage Distribution S. A. | Colored indicator to measure the distribution of the hydrocarbon families contained in a mixture, the procedure for obtaining it, and its uses |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10502111A (ja) | 1998-02-24 |
| EP0766724A1 (de) | 1997-04-09 |
| HU9603550D0 (en) | 1997-02-28 |
| BR9508104A (pt) | 1997-08-12 |
| CZ379296A3 (en) | 1997-06-11 |
| PL317941A1 (en) | 1997-05-12 |
| CA2193886A1 (en) | 1996-01-04 |
| ITMI941320A1 (it) | 1995-12-24 |
| HUT76753A (en) | 1997-11-28 |
| CO4410389A1 (es) | 1997-01-09 |
| NO965554L (no) | 1997-02-18 |
| IL114195A0 (en) | 1995-10-31 |
| ITMI941320A0 (it) | 1994-06-24 |
| AU2792895A (en) | 1996-01-19 |
| IT1269947B (it) | 1997-04-16 |
| MX9700119A (es) | 1997-04-30 |
| NO965554D0 (no) | 1996-12-23 |
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