CA2195019A1 - Use of benzaldehydes to mark hydrocarbons - Google Patents
Use of benzaldehydes to mark hydrocarbonsInfo
- Publication number
- CA2195019A1 CA2195019A1 CA002195019A CA2195019A CA2195019A1 CA 2195019 A1 CA2195019 A1 CA 2195019A1 CA 002195019 A CA002195019 A CA 002195019A CA 2195019 A CA2195019 A CA 2195019A CA 2195019 A1 CA2195019 A1 CA 2195019A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- hydrogen
- radical
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 9
- 150000003935 benzaldehydes Chemical class 0.000 title claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003550 marker Substances 0.000 claims abstract description 4
- 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 21
- -1 1,4-butylene Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- UNQLRWBLUDHEDR-UHFFFAOYSA-N morpholin-4-yl-piperidin-1-yl-pyrrolidin-1-yl-lambda3-chlorane Chemical group N1(CCCC1)Cl(N1CCOCC1)N1CCCCC1 UNQLRWBLUDHEDR-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical compound [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-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
- 239000002480 mineral oil Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-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
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101150049479 CCNC gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KLHYPYAETJWSBK-UHFFFAOYSA-J Cl[Zn](Cl)(Cl)Cl Chemical compound Cl[Zn](Cl)(Cl)Cl KLHYPYAETJWSBK-UHFFFAOYSA-J 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-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
- 229930194542 Keto Natural products 0.000 description 1
- 101100087528 Mus musculus Rhoj gene Proteins 0.000 description 1
- 101100208721 Mus musculus Usp5 gene Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000005505 Ziziphus oenoplia Nutrition 0.000 description 1
- 244000104547 Ziziphus oenoplia Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004035 chlorins Chemical class 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 238000001514 detection method Methods 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
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 101150014588 ethA gene Proteins 0.000 description 1
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 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
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
-
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Abstract
The invention relates to the use of benzaldehydes of the formula (I), in which ring A can be benzo-anellated and R1, R2 and R3 are hydrogen, hydroxy, C1-C15 alkyl, C1-C15 alkoxy, cyano, nitro or a radical of the formula NR4R5 or COOR6, in which R4 is hydrogen or possibly substituted C1-C15 alkyl, R5 is possibly substituted C1-C15 alkyl or a radical of the formula L-NX1X2, in which L is C2-C8 alkylene and X1 and X2 are mutually independently C1-C6 alkyl or, together with the nitrogen atom bonding them, a heterocyclic radical, and R6 is hydrogen, possibly substituted C1-C15 alkyl or a radical of the formula L-NX1X2, in which L, X1 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
~ 2~ 9501 9 Use o~ b~ hydes for marking LydL~L~o~s ~he preDent invention rel-t ~ to the u-e of b~n7~ 'yd-~ o~ t~e 5 form~l~ I
C ~ (I) 15 in which the ring A may be ~_,zo~u,Ld, and ~l, RZ and R3 are each, i , ly o~ o~e anor~er~ hydrogen, hydroxyl, Cl-Cl~- lkyl, C1-C1~-alkoxy~ cyano, nitro or a r~dic~l Or thu formula ~R~R5 or cooR5 where R~ is hydrogen or C1-C15-alkyl wlth or without interruption by ~rom 1 to 4 oxygen atoml in ether function and with a without sub~titution by phenyl~
RS is C1-Cls-~lkyl with or without iut~L~u~Llon ~y rrom 1 to 4 oxygen atomL in ether f unction and with or without sub~titution by phenyl, or i8 a radical o~ the for~ula L-~X~XZ where L iB Cz-C~-alXylene and Xl and X2 are si~gly, ~ L ~1 tly o~ each other, C1-C5-alkyl or togethQr, together with the nitrogen atom joining them together, n 5- or C ~i Laturnted heterocyclic r~dical with or without an oxygen atom in the ring, and 3~
~5 i~ hydrogen, Cl-Cls-~kyl with or without lnterru~tion by ~rom 1 to 4 oxyqen atoms ln ether runction or a radical o~ the for~la L-N~lX2 where L, xl nd x2 are ~ach as de~in-d nbove, 4~
ns markcrs for L~d~o~ to a method for detecting these ben-2aldehyd-~ in hyll ~J~ c~ ~nd to hydrochrbon5 _ ~nq the ~ rrr~ }~r.~l 7.1r~ ,3 4~ US-A-5 145 573, VS-A-5 lB2 372 and EP-A-499 845 disclose azo dyes which are used as markers for minQral oil~ ~5-A-4 OC9 CC8 describes a method for mar~ang mineral oils ~ith disa20 dyes by OESRr1T SE I TE~ 2 ~ 21 9~0~ 9 V~ ~ hi 1; ~ nrj the dye added to the mineral oil by adding to the ~
rarked ~ineral oil an ad~LL~L which binds oth~r colored ingredien~s of ~he ~iner~l oil.
5 D~ 3 608 il5 and ~-A-3 724 757 describe benzopyran derivatives and their us- in r~cr~rr7;~g syster~.
Exs~ple 1 of D~-3-608 215 ~-- hQ~ the renction of 2,3-dimethyl-~L~ yllU~ tr~chlorozlncnt~ with 4-di~ethylr '-~b-nr~l~7~hyde 10 in ~ethanol to for the colored salt o~ tho formula ~ CE Ch ~ ~7(C~3)- ZnCl3~
W0-h-11 466~1994 d ~ hr.~ th~ use of substitut-d nnilines for marking ~in-rnl oils.
ZO
It is an object of thQ present invention to provide novel marker$
for l~ L~hv~ Tha novel markers rhould be readily ~h~t~;nnh30 ~nd ~oluble ln h~dL~r1LL~ ~bey should also be si~ple to de-tect; sp~ A3ly, even very Lmall nmounts of markc~r should bo 25 vi-ih;l17~h~e through a strong color renction.
We have ~ound that this object is nchleved by the above-defined h~n7~ld~hydes of the formula I.
30 Any ~lkyl or alkylene rpp~. ing in the nbo~~rLioned formula I
may be straig~t-chain or branch-d.
X1 and x2 co~bined with the nitrogen ato~ ~oini~g them togather into a 5- or C ~d s~Lu~L~d heterocyclic radical with or ~5 ~ithout an oxygen atom in the ring can be for cxn~ple pyrrol~di-nyl, p;r~ ;nyl or morpholinyl.
Rl, R2, R3, R4, R5, R6, X1 and X2 are each ior e~a~ple methyl, ethyl, propyl, isapropyl, b~tyl, isobutyl, ~ec-butyl, pentyl, ~0 isopen~yl, neopantyl, tort-pentyl, bexyl or 2-~ethylpentyl.
Rl, R2, R3, R4, R5 and R6 may eaah al~o be for ex~mple heptyl, oc~yl, 2-athylhexyl, f~coctyl, nonyl, isononyl, decyl, i~odecyl, undecyl, dodecyl, tridecyl, 3,5,5,7 teL. ylnonyl, isotri-45 decyl, t~Lad__~l or ~_~L~de~yl ~the above do~ignation~ isooctyl,i~30nonyl, 1sodecyl a~d isotridecyl are tr~vial name~ derived fro~
the oxo proce~s alcohol- - cf UllDann~s Encrclopedia of -~~ ~ - - - 2 I-~q 5 a ~ 9 Industri l Chemistry, 5th ~dition, Oo~ Al, p~ J~ ~u ~Y~
~l~o Vol A lQ, p~ge~ 2B4 and 2~5) Rl, RZ and R3 m y each ~l50 be $or exnmple methoxy, ethoAy, 5 pzopoxy, ;'~I~ butoAy, isobutoxy, L~c-b~to~y, p~ntyloxy, i~opentyloxy, neopentyloAy, tert-p-n~yloxy, hexyloAy, 2-~ethyl-pentylo~y~ heptyloxy, octyloxy, 2-ethylhexyloxy, i~ooctyloxy, nonyloxy, iso~onyloxy, decyloxy, isodecyloxy, UndecyloXy, dodecyloxy, tridecyloxy, 3,5,5,7-t~t, LLylnonyloxy, isot i-10 decyloxy, tuL -' ~loxy or ~cntadc_yloxy R~ ~nd R5 may ~ach also be for example 2 ' ~_Lhyl, 2-ethoYy-ethyl, 2-~ v~vA~_Lh~l, 2-ir ~ ~VA~_Lhyl~ 2-L~LOA~-~U~ 2- or 3 LLvAy~v~l~ 2- or 3 ~t~_y ~L V~ 1 ~ 2 or 3 ~ ~PVAY~V~11~ 2-15 or 3-L~L~A~lv~l, 2- or ~ - ~L~Lyl~ Z- or 4-~LLvA~b~Lyl~ 2-or 4-~ ~v~L~Lyl, 2- or 4-~Lv~yL~Lyl, 3,6 ~ ~ptyl, 3,6-vi-oxaoctyl, 4,8-dioxnnonyl, 3,7-dioxaoctyl, 3,7 ';~ ~nyl, 4,7-di-oxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-~r~Yr~yl~
3,6,9-tr~ 1, 3,6,~,12-L~ L~ LLldecyl, ben~yl or 1- or 20 Z-phenyl-thyl ~ s for ex~mple (CH2)2, tcH2~3~ ~C~2)~, (cEz)s~ tCH2)C~ ~ch2) (C~2)8~ CH(C~)C~2 or CE( OE3~C~(CH3~
25 P _r~ according to the pr-~ent inv ntion is given to ~he u9e of b~n~ yd~s of the formula I where at least one of the radi-c~ls R~ to R3 i5 a radlc~l o~ the formula ~R4R5 Where R~ and R5 are each as de~ined above 30 Particular pre~erenc- for the marking o~ h~ L~ng is given to the ~e of ben~ ~hyde~ of the ~ormula Ia ~ 0 U: U~ (Ia), where Rl, R2, R~ and R5 are e~ch as deLined abo~e O partic~lar suitability are h~7Al~hyde5 of the ~ormula ~a where Rl and R~ nre 1rU_~ nt7y of e~ch other hydrogen, 45 hydroxyl, Cl-Cl5-~lkyl, Cl-Cl5-~lkoxy or a radical of the formula 21~ 9 S O ~ 51 CooR~ where R~ 1~ as de~lnea a~ove, ~- 5 L~ 15~ Y' and Rs i5 Cl-Cls-~lkyl.
P~rtlculrr pre~erenec for t~n m~rking o~ ~"5 i3 g~ven to 5 the use Or hr~ h~e~ of the form~lla Ia wh~re R4 and R5 ~re in-5 , ' tly Or each other Cl-Cl3-~lkyl and Rl and R2 are e~ch hydrogen Tne present inventio3 lso proTide~ a method of detect~ng ben-0 7~ das of form~la I in hy~ro~ , which ~ ~ r ~reat~ng the hydroc~bon w~th an ~_ al~lir or ~lroh~ medium g ~ protic ~cid, rt ieast one compound from the group o~
'~ conslstlns of ~ub~tltutad benzooyrylium 381t8 oS the formula II
- ~ ~ tII)~
where R7 is Cl-C8- ~Xyl, phcnyl, Cl-C5-alkoxy or haloge and R~ is r~thyl or R7 and R~ together are 1,4-butyleno and the ring ~ may be fused with a bonzene ring And may b- s~bstituted by C~-C~-alkyl, pyrrolidino, pi - A~, ~orpholino, chlorins or 25 bro~ine or in ring pc-it'on 7 ~~t~ lly also by hydroxyl, Cl ~~ rTy~ mono- or d~(C1-C5-alkyl~amlno which mly in turn be 8 bst~tut~d by chlorine or phenyl, and Xe is an option~ anion, and indoles Or the formula III
~ R9 ~III), where R9 and Rl~ are inA~ Ar~tly of each other hydrogen, hydrox-yl, a radical o~ the formula ~R4R5, ~here R~ and R5 are each as de~in~d abovo, Cl-C~-alkyl, phenyl, Cl-Cs-alkoxy or halogDn, nnd optionally a halide o~ th- m~tals zinc, alu~inu3 or tin P ~felenc~ ~ccording ~o thc present invention i8 g~ven to the ~se o~ indoles o~ the ~ormula III, s, '~lly 2-phenylindole ~5 _ ~ . 2~ 9Sa19 ~xamples o~ suitablo anions X3 are tetrachlorozinc~te, halide, sulfate, tetr fluorD~a~Q ~n~ phosph~te T_e ~r~n7~1 ~ohyde~ I, the benzopyrylium ~alt8 II ~nd also the ~n-5 doleL III are ~enerally known per se Marking for the purpo~e~ of the pre~ent invention is the ~ddition to h~d~v OlL~n~ of the ~ - l~hydes of the ~ormula I in ~uoh ~
C~ L~ On that, to the human eye, tb~ L~d~vcr~L~lL b~ve b~re-10 ly any or no vi~ble color, but the ~n~ e~ydes o~ the ~orml~laI A~e rnAdily and distinctly vi91hly detectable by the r~thods of Aotection ~ore p~ticuiarly ~ - ~~' her in ~he presen~ invention furth r provides hy~roe~r~n~ ¢o~prising 15 one or more of the 5 ~ hyd~s Or th- formula I
~IL~.G~Lo~s for th~ purpo~ea Or the present invention nre ~l~rhot~ or aromatic ~yd~ b~ which ure liguid undcr stan-dart condition~ ThQ~e are in ~rticular ml~eral oils, for exam-20 ple motor fuels, ~uch a~ gasolene, kQro~ene or diesel fuel, oroil~, ~uch a8 ~uQl oil or enginG oil ~he b~ A~hydes of the formula I are , Al ly ~uit~ble for marking mi~eral oils where 90~e ~orm of markinq is mandatory, for 25 ~ample for tax r~ason~ To keep the co~tg for t~is to a uinimu3, lt is de~ir~bl~ to keep th- a~ou~t of ~rrker uLed to a min~um To mark hydrocarbons, the b~ A~yd-~ of t e formul~ ~ are used either without a solvent or in thQ form of ~lut;~ Suit~ble 30 solvents Are organ~ c aolvents Pre~er~nce is given to u~ing ~ro-matic h~l~v -~ , 8uch a~ toluene, xyleDe, dodecylbenzono, di1sopropylnaphth~1ene or a mixtur~ o~ higher arom~tics ~vailable from Shell ~s 8hellsol0 AB ~o avoid tho rQculting 501ution h~ving ~ high visco~ity, the .~hc~L~LLon o~ hA-7-l~ohyde I
35 cho~-n for the olut;on gonQrally rrnge8 irom 5 to ~0 S by weight, based on t~o solution The ~olubility may bo improved by u~ing ~urther, co-solventi, for examplQ ~lcohols, 8uch aJ me~hanol, ethA~ol, propa~ol, ~Aprop~n-40 ol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol,2-6thyl~ex~301 or cy~lAhovAnAl~ glycol6, such as butylethyle~e ~lycol or methylprcpylene glycol, zmine8, such as triethylamine, dL1800ctylamine, dLcyclohexylamLne, aniline, ~-methyla~ ne, ~,~-dimethyla~iline, to~ 1ne or xylidine, ~ uoh 45 as 3-~2-methoxyethoxy)propylamine, o-cresol, m-cresol or p-cre501, ketone~, ~uch a~ diethyl keto~e or cy~1 ~h~v=n~n~
1 w tam~, such ~s y-butyrolactone, carbonates, ~uch a~ othylene ~C01~1T ~ T Tn~l R':/
C ~ (I) 15 in which the ring A may be ~_,zo~u,Ld, and ~l, RZ and R3 are each, i , ly o~ o~e anor~er~ hydrogen, hydroxyl, Cl-Cl~- lkyl, C1-C1~-alkoxy~ cyano, nitro or a r~dic~l Or thu formula ~R~R5 or cooR5 where R~ is hydrogen or C1-C15-alkyl wlth or without interruption by ~rom 1 to 4 oxygen atoml in ether function and with a without sub~titution by phenyl~
RS is C1-Cls-~lkyl with or without iut~L~u~Llon ~y rrom 1 to 4 oxygen atomL in ether f unction and with or without sub~titution by phenyl, or i8 a radical o~ the for~ula L-~X~XZ where L iB Cz-C~-alXylene and Xl and X2 are si~gly, ~ L ~1 tly o~ each other, C1-C5-alkyl or togethQr, together with the nitrogen atom joining them together, n 5- or C ~i Laturnted heterocyclic r~dical with or without an oxygen atom in the ring, and 3~
~5 i~ hydrogen, Cl-Cls-~kyl with or without lnterru~tion by ~rom 1 to 4 oxyqen atoms ln ether runction or a radical o~ the for~la L-N~lX2 where L, xl nd x2 are ~ach as de~in-d nbove, 4~
ns markcrs for L~d~o~ to a method for detecting these ben-2aldehyd-~ in hyll ~J~ c~ ~nd to hydrochrbon5 _ ~nq the ~ rrr~ }~r.~l 7.1r~ ,3 4~ US-A-5 145 573, VS-A-5 lB2 372 and EP-A-499 845 disclose azo dyes which are used as markers for minQral oil~ ~5-A-4 OC9 CC8 describes a method for mar~ang mineral oils ~ith disa20 dyes by OESRr1T SE I TE~ 2 ~ 21 9~0~ 9 V~ ~ hi 1; ~ nrj the dye added to the mineral oil by adding to the ~
rarked ~ineral oil an ad~LL~L which binds oth~r colored ingredien~s of ~he ~iner~l oil.
5 D~ 3 608 il5 and ~-A-3 724 757 describe benzopyran derivatives and their us- in r~cr~rr7;~g syster~.
Exs~ple 1 of D~-3-608 215 ~-- hQ~ the renction of 2,3-dimethyl-~L~ yllU~ tr~chlorozlncnt~ with 4-di~ethylr '-~b-nr~l~7~hyde 10 in ~ethanol to for the colored salt o~ tho formula ~ CE Ch ~ ~7(C~3)- ZnCl3~
W0-h-11 466~1994 d ~ hr.~ th~ use of substitut-d nnilines for marking ~in-rnl oils.
ZO
It is an object of thQ present invention to provide novel marker$
for l~ L~hv~ Tha novel markers rhould be readily ~h~t~;nnh30 ~nd ~oluble ln h~dL~r1LL~ ~bey should also be si~ple to de-tect; sp~ A3ly, even very Lmall nmounts of markc~r should bo 25 vi-ih;l17~h~e through a strong color renction.
We have ~ound that this object is nchleved by the above-defined h~n7~ld~hydes of the formula I.
30 Any ~lkyl or alkylene rpp~. ing in the nbo~~rLioned formula I
may be straig~t-chain or branch-d.
X1 and x2 co~bined with the nitrogen ato~ ~oini~g them togather into a 5- or C ~d s~Lu~L~d heterocyclic radical with or ~5 ~ithout an oxygen atom in the ring can be for cxn~ple pyrrol~di-nyl, p;r~ ;nyl or morpholinyl.
Rl, R2, R3, R4, R5, R6, X1 and X2 are each ior e~a~ple methyl, ethyl, propyl, isapropyl, b~tyl, isobutyl, ~ec-butyl, pentyl, ~0 isopen~yl, neopantyl, tort-pentyl, bexyl or 2-~ethylpentyl.
Rl, R2, R3, R4, R5 and R6 may eaah al~o be for ex~mple heptyl, oc~yl, 2-athylhexyl, f~coctyl, nonyl, isononyl, decyl, i~odecyl, undecyl, dodecyl, tridecyl, 3,5,5,7 teL. ylnonyl, isotri-45 decyl, t~Lad__~l or ~_~L~de~yl ~the above do~ignation~ isooctyl,i~30nonyl, 1sodecyl a~d isotridecyl are tr~vial name~ derived fro~
the oxo proce~s alcohol- - cf UllDann~s Encrclopedia of -~~ ~ - - - 2 I-~q 5 a ~ 9 Industri l Chemistry, 5th ~dition, Oo~ Al, p~ J~ ~u ~Y~
~l~o Vol A lQ, p~ge~ 2B4 and 2~5) Rl, RZ and R3 m y each ~l50 be $or exnmple methoxy, ethoAy, 5 pzopoxy, ;'~I~ butoAy, isobutoxy, L~c-b~to~y, p~ntyloxy, i~opentyloxy, neopentyloAy, tert-p-n~yloxy, hexyloAy, 2-~ethyl-pentylo~y~ heptyloxy, octyloxy, 2-ethylhexyloxy, i~ooctyloxy, nonyloxy, iso~onyloxy, decyloxy, isodecyloxy, UndecyloXy, dodecyloxy, tridecyloxy, 3,5,5,7-t~t, LLylnonyloxy, isot i-10 decyloxy, tuL -' ~loxy or ~cntadc_yloxy R~ ~nd R5 may ~ach also be for example 2 ' ~_Lhyl, 2-ethoYy-ethyl, 2-~ v~vA~_Lh~l, 2-ir ~ ~VA~_Lhyl~ 2-L~LOA~-~U~ 2- or 3 LLvAy~v~l~ 2- or 3 ~t~_y ~L V~ 1 ~ 2 or 3 ~ ~PVAY~V~11~ 2-15 or 3-L~L~A~lv~l, 2- or ~ - ~L~Lyl~ Z- or 4-~LLvA~b~Lyl~ 2-or 4-~ ~v~L~Lyl, 2- or 4-~Lv~yL~Lyl, 3,6 ~ ~ptyl, 3,6-vi-oxaoctyl, 4,8-dioxnnonyl, 3,7-dioxaoctyl, 3,7 ';~ ~nyl, 4,7-di-oxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-~r~Yr~yl~
3,6,9-tr~ 1, 3,6,~,12-L~ L~ LLldecyl, ben~yl or 1- or 20 Z-phenyl-thyl ~ s for ex~mple (CH2)2, tcH2~3~ ~C~2)~, (cEz)s~ tCH2)C~ ~ch2) (C~2)8~ CH(C~)C~2 or CE( OE3~C~(CH3~
25 P _r~ according to the pr-~ent inv ntion is given to ~he u9e of b~n~ yd~s of the formula I where at least one of the radi-c~ls R~ to R3 i5 a radlc~l o~ the formula ~R4R5 Where R~ and R5 are each as de~ined above 30 Particular pre~erenc- for the marking o~ h~ L~ng is given to the ~e of ben~ ~hyde~ of the ~ormula Ia ~ 0 U: U~ (Ia), where Rl, R2, R~ and R5 are e~ch as deLined abo~e O partic~lar suitability are h~7Al~hyde5 of the ~ormula ~a where Rl and R~ nre 1rU_~ nt7y of e~ch other hydrogen, 45 hydroxyl, Cl-Cl5-~lkyl, Cl-Cl5-~lkoxy or a radical of the formula 21~ 9 S O ~ 51 CooR~ where R~ 1~ as de~lnea a~ove, ~- 5 L~ 15~ Y' and Rs i5 Cl-Cls-~lkyl.
P~rtlculrr pre~erenec for t~n m~rking o~ ~"5 i3 g~ven to 5 the use Or hr~ h~e~ of the form~lla Ia wh~re R4 and R5 ~re in-5 , ' tly Or each other Cl-Cl3-~lkyl and Rl and R2 are e~ch hydrogen Tne present inventio3 lso proTide~ a method of detect~ng ben-0 7~ das of form~la I in hy~ro~ , which ~ ~ r ~reat~ng the hydroc~bon w~th an ~_ al~lir or ~lroh~ medium g ~ protic ~cid, rt ieast one compound from the group o~
'~ conslstlns of ~ub~tltutad benzooyrylium 381t8 oS the formula II
- ~ ~ tII)~
where R7 is Cl-C8- ~Xyl, phcnyl, Cl-C5-alkoxy or haloge and R~ is r~thyl or R7 and R~ together are 1,4-butyleno and the ring ~ may be fused with a bonzene ring And may b- s~bstituted by C~-C~-alkyl, pyrrolidino, pi - A~, ~orpholino, chlorins or 25 bro~ine or in ring pc-it'on 7 ~~t~ lly also by hydroxyl, Cl ~~ rTy~ mono- or d~(C1-C5-alkyl~amlno which mly in turn be 8 bst~tut~d by chlorine or phenyl, and Xe is an option~ anion, and indoles Or the formula III
~ R9 ~III), where R9 and Rl~ are inA~ Ar~tly of each other hydrogen, hydrox-yl, a radical o~ the formula ~R4R5, ~here R~ and R5 are each as de~in~d abovo, Cl-C~-alkyl, phenyl, Cl-Cs-alkoxy or halogDn, nnd optionally a halide o~ th- m~tals zinc, alu~inu3 or tin P ~felenc~ ~ccording ~o thc present invention i8 g~ven to the ~se o~ indoles o~ the ~ormula III, s, '~lly 2-phenylindole ~5 _ ~ . 2~ 9Sa19 ~xamples o~ suitablo anions X3 are tetrachlorozinc~te, halide, sulfate, tetr fluorD~a~Q ~n~ phosph~te T_e ~r~n7~1 ~ohyde~ I, the benzopyrylium ~alt8 II ~nd also the ~n-5 doleL III are ~enerally known per se Marking for the purpo~e~ of the pre~ent invention is the ~ddition to h~d~v OlL~n~ of the ~ - l~hydes of the ~ormula I in ~uoh ~
C~ L~ On that, to the human eye, tb~ L~d~vcr~L~lL b~ve b~re-10 ly any or no vi~ble color, but the ~n~ e~ydes o~ the ~orml~laI A~e rnAdily and distinctly vi91hly detectable by the r~thods of Aotection ~ore p~ticuiarly ~ - ~~' her in ~he presen~ invention furth r provides hy~roe~r~n~ ¢o~prising 15 one or more of the 5 ~ hyd~s Or th- formula I
~IL~.G~Lo~s for th~ purpo~ea Or the present invention nre ~l~rhot~ or aromatic ~yd~ b~ which ure liguid undcr stan-dart condition~ ThQ~e are in ~rticular ml~eral oils, for exam-20 ple motor fuels, ~uch a~ gasolene, kQro~ene or diesel fuel, oroil~, ~uch a8 ~uQl oil or enginG oil ~he b~ A~hydes of the formula I are , Al ly ~uit~ble for marking mi~eral oils where 90~e ~orm of markinq is mandatory, for 25 ~ample for tax r~ason~ To keep the co~tg for t~is to a uinimu3, lt is de~ir~bl~ to keep th- a~ou~t of ~rrker uLed to a min~um To mark hydrocarbons, the b~ A~yd-~ of t e formul~ ~ are used either without a solvent or in thQ form of ~lut;~ Suit~ble 30 solvents Are organ~ c aolvents Pre~er~nce is given to u~ing ~ro-matic h~l~v -~ , 8uch a~ toluene, xyleDe, dodecylbenzono, di1sopropylnaphth~1ene or a mixtur~ o~ higher arom~tics ~vailable from Shell ~s 8hellsol0 AB ~o avoid tho rQculting 501ution h~ving ~ high visco~ity, the .~hc~L~LLon o~ hA-7-l~ohyde I
35 cho~-n for the olut;on gonQrally rrnge8 irom 5 to ~0 S by weight, based on t~o solution The ~olubility may bo improved by u~ing ~urther, co-solventi, for examplQ ~lcohols, 8uch aJ me~hanol, ethA~ol, propa~ol, ~Aprop~n-40 ol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol,2-6thyl~ex~301 or cy~lAhovAnAl~ glycol6, such as butylethyle~e ~lycol or methylprcpylene glycol, zmine8, such as triethylamine, dL1800ctylamine, dLcyclohexylamLne, aniline, ~-methyla~ ne, ~,~-dimethyla~iline, to~ 1ne or xylidine, ~ uoh 45 as 3-~2-methoxyethoxy)propylamine, o-cresol, m-cresol or p-cre501, ketone~, ~uch a~ diethyl keto~e or cy~1 ~h~v=n~n~
1 w tam~, such ~s y-butyrolactone, carbonates, ~uch a~ othylene ~C01~1T ~ T Tn~l R':/
- 2~ ~501 9 : 6 c-rbonate or propyl-~e rA hnnn1~ pheno}s, LU -h a9 t~DUtylp~enol cr no~ ~nol, esters, such as methyl phthalate, ethyl ~hth~late, 2-ethylheXyl phth~l~te, ethyl acetate, butyi acet~te or cyclohexyl acetate, ~mid-s, ~uch as N,~-di~ethylfr~r-~;~~, ~,N-diethylo~ or N-methylpys~ ~, or mixtures thereof.
~h~ h~n7-l~hyd~s of the formul~ I to bQ u5Qd o~crr~in~ to the pre~ent ~nvantlon perm~t very simple detection o~ marked hydro-10 carbons, ~ven i~ th m~rker substancec are prc~ent only in a con-centration o~ ~bout 1~ ppm or les~.
~he presence in l~d~ h~ of the _ ~ o~ the formula I
u~e~ as m rkers i~ ~d.~ ly detected on treating the hydro-15 carbon with an a~ alrnhnlic or ~ nl;~ medium ~ ng apyryllum salt o~ th~ formula II and/or an indol- Or the ~ormula III, u protio aeid and optionally a h-lid- o~ the metals z~nc, ~ ~ or tin. In aqueou~-Alrnh~l~c media, the Weight ratlo of w~t r : Alcohol varies from 0.5 : 1 to 4 : 1, and is preferably lQ ~bout 1 : 1. The ~es~lt is a di~tinctly ~i~ible color change Or th- -_~D Alrnhr~ ph~se.
Suitable al cohols lnclud- for ex~mple ethanol, propanol, iso-propanol, l-meth~ 2-ol, ethylene glycol or 1,2- or Z~ 1,3-propylene glycol. Tho use o~ ethanol is ~ ~L~r~d.
Suitabl- protlc ~cids for the method oi the present invention in-clude in particular strong acids, i.e. protic acids who~e pX_ v~lue i~ e 3.5 Such acids include for examp}e i~rg-~r or 30 organlc ncid~, ~uch _s perchlor~c acld, hydroiodic acid, hydrochloric acid, hln ~ ' r acid, hydro~luoric acid, ~ulfuric ecld, nitria acid, ~ acid, ~ ~ ~ lf~n;r acid, toluene3ul~0nic acid, naphth-l r- 1 fr-i r acid~ ~n U1 ~rn ~ ~
ncid, oxalic acid, maleic aoid, chl~l~r- ~c acid, dichloroacetic 35 aeid or bromoacetla acid. In some cases it can be of advantage to ~uf~er these _cidL, for e~ample by ~dding acetic acid.
-~s ~ell as to o- or p-tolum~E lrOn;~ acid, ~L.~eL~ is given ~speclally to inorganic acids, with hydrochlorio acid and sul~u-4~ ric acid being particularly p ef~l~ ~d.
suit-ble halides o~ the metals zinc, Al--~ or tin include for ~ ~mple zinc chlorid , zinc bromide, aluminu~ chloride, aluminu~
bromide or t~n ~etr~hl ~r~ *~ 7inc ~hl ~r; ~ p rticularly pre-45 ~erred.
21 ~ 9 ~t is genorally s~ff;~ont to ex~ract rro~ about lo to ~o ~ or - - -tbe h~d~colL~ ~arked according to the present inventlon with f~om 1 to 50 ~1 o~ an aUu~u~~ A~Al;r or ~7~A~t~r so~ut~on o~
a pyryliu2 salt of the ~ormula II and~or of an indole oi the for-muia III, a prot~c acid, nrt~An~l7y in tho pre~ence of ~ ~etal halide, to obtain a color change It ic ~tso po~iblo to r~place th~ Jolution Or th- protic aeld by An ~ Ahnl~ solution of a 2etal halide ~lone, sincY the latter likewise has an acid roaction lC
Th~ ~oaca~LL~Oion o~ th~ protio acid ln tho -_ &7 ~AhAl; ~ or AhA~ olution is ~enorally from 5 to 50 ~ by weiqht, pre~er-~bly ~rom 10 to 30 ~ by w ight The ccnc~uLLOLlon of met~l halide ~s generally from O to 50 % by weight, pre~erably fro~ 5 to 20 1~ by w~ight, in each case ba3ed on the wQlght Or thQ solution .
On- considerabl- __ o~ the inventlon is that two different r~thods can be us-d ~or ~te~t; ng the L ~7~yde~ o_ the rOr-mula I Detect~on i~ ~Ic Gf~ vQry r-liable, even in the pres-ZO ence of pos~ible int~f~ce teg additives in diesel ~uel) The Examples which fol_ow illustrate the in~ention Gener~7 method 1 Co~mercial diesel _uel wac mix-d with 10 ppm each o~ benzaLde-hyde ~or this the aldehyde was prediccclved in toluena ~n 0 1 ~trength by wei~ht and this solution w~5 added to the diesel ~u~l .
In each of ~xamples 1 to 12 10 ml o~ the diesel fuel thus ~rked were admixcd with 2 ~1 of reagent solutlon and shaken for 5 min-utes Then 1 m~ of water was added ~nd the shaking was continued for a further 5 minute~ Tho aqueou~ phase showed the color ln~i-3~ catod below in T~ble ~o ~QagQ~t solution 1 5 ~i of 1 % Ltrength by weight indole i ethanol 40 5 21 Or ~ ~ ~ LL~L~d hydrochloric acid 5 g of zinc chloride 95 21 0~ acetic acid 4 i ~ 21 9~0~ 9 ... .... ~ ~ -Reagent ~olution 2 ~ ~
... . ~
S ~1 o~ 1 ~ trength ~y welght 2-methylindole in c~hannl 5 ml 0~ C~e~LL aLed hydrochloric ncid 5 g o~ zinc chloride 95 rl o~ acstic acid R~agant solution 3 lD S ~1 o~ 1 ~ strength by weight 2-phenylindole in ethanol 5 r~ of L~C~.~ ~d hydrochloric acid ~5 g Or zino chloride 95 ml o~ ace-~c acid 15 P rticularly advantageouc re~ults are o~taincd cn rir~t f~lteri~g the die-cl fuel through cillca gel.
3~
Table No. 1 ~ ' ~~-- ~ ' -~~ /-E~c. No. Aldehyde Roagont Color - 5 1 1 mz~g~:ntn ~3~
~?( C}~3 ) z 2 2 v$olet c:~O
N~ 3 ) z 3 :~ Yiolet ceo ~3 N~C~13)z 4 1 orange CEIO
~3~o3 ~ C2~;~ ) z 2 reddish viole~
C~O
~ - ~o~
~o b~
~(czEs~z .~
--~ r ~ =
21 9 5 (~1 9 I!:X. I~o.~ldehydo ~e~gent Color 6 3 ~gent~
C}~O
~3~~~
l~lr2~s~
0 ~ c}~o 1 orange 0E~
~_ 8 CEO 2 reddi~h violet g CEO 3 2D.~Lgent~
~OE
3~ o~
1 r-ddi~h violclt CHO
~C02CH3 N(CH3~2 Ex. ~o. Alduhyd- Ru~qent Color 11 2 blulsh ~iolet a~o ~COzC1~3 3 ) z lD 12 3 blui~h violet ~0 ,~COzC}i~
~S
N(C~3)2 81~il~r result~ are DbtAIned o~ u9ing marker~ ;"g the ~ ~hyde~ l~sted below 1~ T~ble ~o. 2.
T~le No. 2 Ex. ~o. Aldehyde 25 ~3 C~o ~3 N~C2~s)z CEIO
~lC82CCE15) z ~0 - -- ~ 2195019 Ex. 1~ ehyd~
1 5 CE~0 [~3 1 6 Cl~0 ~ ~3 2 CE!3-N-c2~l4c;
l B c}10 0~1 ~C~3)2 19 C~O
3s ~3~~~
( ( c~2c6El5 ~ 2 ~1 ,. OCEI3 W
N(C2E~s)2 _ .
-- s - 13 219$0f9 Ge~rnl mcShcd 2 Cor~rcial die~el fuel wa~ xed with 10 pp~ o~ each benz~lde-hyde. For this the ~ wa8 p~edi~ol~-d ln teluune ~n 5 0.~ ~ ~trength ~y weight And th~J solutlon WR~ ndded to th- die-~1 fuel.
In e~ch of Exnmples 21 to 30 10 ml of the m2rked die~cl fu-l wer-~ixed with 2 ml of re~gent solution 4 And refluxed ~or 5 ~n-10 ute~. Then 1 ml of 1~1 vtv water~eth~nol w~n ncded And the mi~-tur~ wan shaXen for 5 m~nut-3s. The aquecu~ ph~e shAowed the color ~n~r~tD~ ~elow {n Table No. 3.
~eagent Lolution 4 5 ml of the ~ zo~l~ylLul~ ~alt of the for~ula ~ Q~3 ZnCl 1 ~ ~trength in w~ter 25 ml o~ atLd hydrochloric acid - 22~ ml of acetic ~cld T~ble 3 EX. No.Aldehyde Q CDlor 21 C6~5 ~lue C~O
3~ [ ~
NtCEI3)z ,0 22 C~3 ~lu~
CEIO
~(C~S3 ) il - ~ ~ 219501 9 Ex. No. ~ldehyde Q Color 23 Cc~is blue CE~O
S ~ ~2CEI3 N~CEi~)2 10 24 ~ blue C~O
~ CO2CII3 N~CE~3~2 Z5 cH3 bluo C~IO
~' ~t C~5 ) 2 26 C~iO C~l~ blue o~
~3~
35 27 CEI0 ~ blue ~~~~~
O~
4~ .
; ~ ' 2i 9501 9 '' 15 Ex. ~o. ~ldehyde Q Color 28 C~3 red~ish violet C~O
0~
10 2~ c~3 reddi~h violet C~o ~ 1 OC~3 C~3 violet C~O
~ OC~
Similar results are obt ~ned on repl~cing the benzopyrylium salt o~ reagent col~tion 4 ~y that Or the formul~
1~0 Z~C13e g5
~h~ h~n7-l~hyd~s of the formul~ I to bQ u5Qd o~crr~in~ to the pre~ent ~nvantlon perm~t very simple detection o~ marked hydro-10 carbons, ~ven i~ th m~rker substancec are prc~ent only in a con-centration o~ ~bout 1~ ppm or les~.
~he presence in l~d~ h~ of the _ ~ o~ the formula I
u~e~ as m rkers i~ ~d.~ ly detected on treating the hydro-15 carbon with an a~ alrnhnlic or ~ nl;~ medium ~ ng apyryllum salt o~ th~ formula II and/or an indol- Or the ~ormula III, u protio aeid and optionally a h-lid- o~ the metals z~nc, ~ ~ or tin. In aqueou~-Alrnh~l~c media, the Weight ratlo of w~t r : Alcohol varies from 0.5 : 1 to 4 : 1, and is preferably lQ ~bout 1 : 1. The ~es~lt is a di~tinctly ~i~ible color change Or th- -_~D Alrnhr~ ph~se.
Suitable al cohols lnclud- for ex~mple ethanol, propanol, iso-propanol, l-meth~ 2-ol, ethylene glycol or 1,2- or Z~ 1,3-propylene glycol. Tho use o~ ethanol is ~ ~L~r~d.
Suitabl- protlc ~cids for the method oi the present invention in-clude in particular strong acids, i.e. protic acids who~e pX_ v~lue i~ e 3.5 Such acids include for examp}e i~rg-~r or 30 organlc ncid~, ~uch _s perchlor~c acld, hydroiodic acid, hydrochloric acid, hln ~ ' r acid, hydro~luoric acid, ~ulfuric ecld, nitria acid, ~ acid, ~ ~ ~ lf~n;r acid, toluene3ul~0nic acid, naphth-l r- 1 fr-i r acid~ ~n U1 ~rn ~ ~
ncid, oxalic acid, maleic aoid, chl~l~r- ~c acid, dichloroacetic 35 aeid or bromoacetla acid. In some cases it can be of advantage to ~uf~er these _cidL, for e~ample by ~dding acetic acid.
-~s ~ell as to o- or p-tolum~E lrOn;~ acid, ~L.~eL~ is given ~speclally to inorganic acids, with hydrochlorio acid and sul~u-4~ ric acid being particularly p ef~l~ ~d.
suit-ble halides o~ the metals zinc, Al--~ or tin include for ~ ~mple zinc chlorid , zinc bromide, aluminu~ chloride, aluminu~
bromide or t~n ~etr~hl ~r~ *~ 7inc ~hl ~r; ~ p rticularly pre-45 ~erred.
21 ~ 9 ~t is genorally s~ff;~ont to ex~ract rro~ about lo to ~o ~ or - - -tbe h~d~colL~ ~arked according to the present inventlon with f~om 1 to 50 ~1 o~ an aUu~u~~ A~Al;r or ~7~A~t~r so~ut~on o~
a pyryliu2 salt of the ~ormula II and~or of an indole oi the for-muia III, a prot~c acid, nrt~An~l7y in tho pre~ence of ~ ~etal halide, to obtain a color change It ic ~tso po~iblo to r~place th~ Jolution Or th- protic aeld by An ~ Ahnl~ solution of a 2etal halide ~lone, sincY the latter likewise has an acid roaction lC
Th~ ~oaca~LL~Oion o~ th~ protio acid ln tho -_ &7 ~AhAl; ~ or AhA~ olution is ~enorally from 5 to 50 ~ by weiqht, pre~er-~bly ~rom 10 to 30 ~ by w ight The ccnc~uLLOLlon of met~l halide ~s generally from O to 50 % by weight, pre~erably fro~ 5 to 20 1~ by w~ight, in each case ba3ed on the wQlght Or thQ solution .
On- considerabl- __ o~ the inventlon is that two different r~thods can be us-d ~or ~te~t; ng the L ~7~yde~ o_ the rOr-mula I Detect~on i~ ~Ic Gf~ vQry r-liable, even in the pres-ZO ence of pos~ible int~f~ce teg additives in diesel ~uel) The Examples which fol_ow illustrate the in~ention Gener~7 method 1 Co~mercial diesel _uel wac mix-d with 10 ppm each o~ benzaLde-hyde ~or this the aldehyde was prediccclved in toluena ~n 0 1 ~trength by wei~ht and this solution w~5 added to the diesel ~u~l .
In each of ~xamples 1 to 12 10 ml o~ the diesel fuel thus ~rked were admixcd with 2 ~1 of reagent solutlon and shaken for 5 min-utes Then 1 m~ of water was added ~nd the shaking was continued for a further 5 minute~ Tho aqueou~ phase showed the color ln~i-3~ catod below in T~ble ~o ~QagQ~t solution 1 5 ~i of 1 % Ltrength by weight indole i ethanol 40 5 21 Or ~ ~ ~ LL~L~d hydrochloric acid 5 g of zinc chloride 95 21 0~ acetic acid 4 i ~ 21 9~0~ 9 ... .... ~ ~ -Reagent ~olution 2 ~ ~
... . ~
S ~1 o~ 1 ~ trength ~y welght 2-methylindole in c~hannl 5 ml 0~ C~e~LL aLed hydrochloric ncid 5 g o~ zinc chloride 95 rl o~ acstic acid R~agant solution 3 lD S ~1 o~ 1 ~ strength by weight 2-phenylindole in ethanol 5 r~ of L~C~.~ ~d hydrochloric acid ~5 g Or zino chloride 95 ml o~ ace-~c acid 15 P rticularly advantageouc re~ults are o~taincd cn rir~t f~lteri~g the die-cl fuel through cillca gel.
3~
Table No. 1 ~ ' ~~-- ~ ' -~~ /-E~c. No. Aldehyde Roagont Color - 5 1 1 mz~g~:ntn ~3~
~?( C}~3 ) z 2 2 v$olet c:~O
N~ 3 ) z 3 :~ Yiolet ceo ~3 N~C~13)z 4 1 orange CEIO
~3~o3 ~ C2~;~ ) z 2 reddish viole~
C~O
~ - ~o~
~o b~
~(czEs~z .~
--~ r ~ =
21 9 5 (~1 9 I!:X. I~o.~ldehydo ~e~gent Color 6 3 ~gent~
C}~O
~3~~~
l~lr2~s~
0 ~ c}~o 1 orange 0E~
~_ 8 CEO 2 reddi~h violet g CEO 3 2D.~Lgent~
~OE
3~ o~
1 r-ddi~h violclt CHO
~C02CH3 N(CH3~2 Ex. ~o. Alduhyd- Ru~qent Color 11 2 blulsh ~iolet a~o ~COzC1~3 3 ) z lD 12 3 blui~h violet ~0 ,~COzC}i~
~S
N(C~3)2 81~il~r result~ are DbtAIned o~ u9ing marker~ ;"g the ~ ~hyde~ l~sted below 1~ T~ble ~o. 2.
T~le No. 2 Ex. ~o. Aldehyde 25 ~3 C~o ~3 N~C2~s)z CEIO
~lC82CCE15) z ~0 - -- ~ 2195019 Ex. 1~ ehyd~
1 5 CE~0 [~3 1 6 Cl~0 ~ ~3 2 CE!3-N-c2~l4c;
l B c}10 0~1 ~C~3)2 19 C~O
3s ~3~~~
( ( c~2c6El5 ~ 2 ~1 ,. OCEI3 W
N(C2E~s)2 _ .
-- s - 13 219$0f9 Ge~rnl mcShcd 2 Cor~rcial die~el fuel wa~ xed with 10 pp~ o~ each benz~lde-hyde. For this the ~ wa8 p~edi~ol~-d ln teluune ~n 5 0.~ ~ ~trength ~y weight And th~J solutlon WR~ ndded to th- die-~1 fuel.
In e~ch of Exnmples 21 to 30 10 ml of the m2rked die~cl fu-l wer-~ixed with 2 ml of re~gent solution 4 And refluxed ~or 5 ~n-10 ute~. Then 1 ml of 1~1 vtv water~eth~nol w~n ncded And the mi~-tur~ wan shaXen for 5 m~nut-3s. The aquecu~ ph~e shAowed the color ~n~r~tD~ ~elow {n Table No. 3.
~eagent Lolution 4 5 ml of the ~ zo~l~ylLul~ ~alt of the for~ula ~ Q~3 ZnCl 1 ~ ~trength in w~ter 25 ml o~ atLd hydrochloric acid - 22~ ml of acetic ~cld T~ble 3 EX. No.Aldehyde Q CDlor 21 C6~5 ~lue C~O
3~ [ ~
NtCEI3)z ,0 22 C~3 ~lu~
CEIO
~(C~S3 ) il - ~ ~ 219501 9 Ex. No. ~ldehyde Q Color 23 Cc~is blue CE~O
S ~ ~2CEI3 N~CEi~)2 10 24 ~ blue C~O
~ CO2CII3 N~CE~3~2 Z5 cH3 bluo C~IO
~' ~t C~5 ) 2 26 C~iO C~l~ blue o~
~3~
35 27 CEI0 ~ blue ~~~~~
O~
4~ .
; ~ ' 2i 9501 9 '' 15 Ex. ~o. ~ldehyde Q Color 28 C~3 red~ish violet C~O
0~
10 2~ c~3 reddi~h violet C~o ~ 1 OC~3 C~3 violet C~O
~ OC~
Similar results are obt ~ned on repl~cing the benzopyrylium salt o~ reagent col~tion 4 ~y that Or the formul~
1~0 Z~C13e g5
Claims (5)
1. The use of benzaldehydes of the formula I
in which the ring A may be benzofused, and R1, R2 and R3 are each, independently of one another, hydrogen, hydroxyl, C1-C15-alkyl, C1-C15-alkoxy,cyano, nitro or a radical of the formula NR4R5 or COOR6 where R4 is hydrogen or C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without substitution by phenyl, R5 is C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without situation by phenyl, or is a radical of the formula L-NX1X2 where L is C2-C8-alkylene and X1 and X2 are singly, independently of each other, C1-C6-alkyl or together, together with the nitrogen atom joining them together, a 5- or 6-membered saturated heterocyclic radical with or without an oxygen atom in the ring, and R6 is hydrogen, C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function or a radical of the formula L-NX1X2 where L, X1 and X2 are each as defined above, as markers for hydrocarbons.
in which the ring A may be benzofused, and R1, R2 and R3 are each, independently of one another, hydrogen, hydroxyl, C1-C15-alkyl, C1-C15-alkoxy,cyano, nitro or a radical of the formula NR4R5 or COOR6 where R4 is hydrogen or C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without substitution by phenyl, R5 is C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without situation by phenyl, or is a radical of the formula L-NX1X2 where L is C2-C8-alkylene and X1 and X2 are singly, independently of each other, C1-C6-alkyl or together, together with the nitrogen atom joining them together, a 5- or 6-membered saturated heterocyclic radical with or without an oxygen atom in the ring, and R6 is hydrogen, C1-C15-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function or a radical of the formula L-NX1X2 where L, X1 and X2 are each as defined above, as markers for hydrocarbons.
2. A use as claimed in claim 1 wherefor the benzaldehydes conform to the formula Ia where R1, R2, R4, and R5 are each as defined in claim 1.
3. A use as claimed in claim 1 or 2 wherefor R1 and R2 are independently of each other hydrogen, hydroxyl, C1-C15-alkyl, C1-C15-alkoxy or a radical of the formula COOR6 where R6 is as defined in claim 1, R4 is hydrogen or C1-C15-alkyl and R5 is C1-C15-alkyl.
4. A method of detaching benzaldehydes of formula I as set forth in claim 1 in hydrocarbons, which comprises treating the hydrocarbon with aqueous-alcoholic or alcoholic medium comprising a protic acid, at least one compound from the group of compounds consisting of substitute pyrylium salts of the formula II
where R7 is C1-C8-alkyl, phenyl, C1-C5-alkoxy or halogen and R8 is methyl or R7 and R8 together are 1,4-butylene and the ring B may be fused with a benzene ring and may be substituted by C1-C4-alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 optionally by hydroxyl, C1-C4-alkoxy, mono- or di(C1-C5-alkyl)amino which may in turn be substituted by chlorine or phenyl,and X.THETA. is an optional anion, and indoles of the formula III
, where R9 and R10 are independently of each other hydrogen, hydroxyl, a radical of the formula NR4R5, where R4 and R5 are each as defined in claim 1, C1-C8-alkyl, phenyl, C1-C5-alkoxy or halogen, and optionally a halide of the metals zinc,aluminum or tin.
where R7 is C1-C8-alkyl, phenyl, C1-C5-alkoxy or halogen and R8 is methyl or R7 and R8 together are 1,4-butylene and the ring B may be fused with a benzene ring and may be substituted by C1-C4-alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 optionally by hydroxyl, C1-C4-alkoxy, mono- or di(C1-C5-alkyl)amino which may in turn be substituted by chlorine or phenyl,and X.THETA. is an optional anion, and indoles of the formula III
, where R9 and R10 are independently of each other hydrogen, hydroxyl, a radical of the formula NR4R5, where R4 and R5 are each as defined in claim 1, C1-C8-alkyl, phenyl, C1-C5-alkoxy or halogen, and optionally a halide of the metals zinc,aluminum or tin.
5. A hydrocarbon with a marker comprising one or more benzaldehyde of the formula I as set forth in claim 1.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4424712A DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
DEP4424712.5 | 1994-07-13 |
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CA2195019A1 true CA2195019A1 (en) | 1996-02-01 |
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CA002195019A Abandoned CA2195019A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
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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) |
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DE19538121C1 (en) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Warp tensioner useful for loom esp. for tension sensitive yarns |
US7179912B2 (en) | 2000-09-01 | 2007-02-20 | Icos Corporation | Materials and methods to potentiate cancer treatment |
US20050103686A1 (en) * | 2002-04-26 | 2005-05-19 | Taylor Spencer E. | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
JP2006523681A (en) | 2003-03-24 | 2006-10-19 | ルイトポルド・ファーマシューティカルズ・インコーポレーテッド | Xanthone, thioxanthone and acridinone as DNA-PK inhibitors |
EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
US9594070B2 (en) * | 2013-11-05 | 2017-03-14 | Spectrum Tracer Services, Llc | Method using halogenated benzoic acid esters and aldehydes for hydraulic fracturing and for tracing petroleum production |
US10017684B2 (en) | 2016-04-20 | 2018-07-10 | Spectrum Tracer Services, Llc | Method and compositions for hydraulic fracturing and for tracing formation water |
WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
US20240219366A1 (en) | 2021-04-20 | 2024-07-04 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
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FR1450273A (en) * | 1965-10-18 | 1966-05-06 | Warner Lambert Pharmaceutical | Preparation usable for the detection of indole produced by microorganisms |
US3930108A (en) * | 1974-11-21 | 1975-12-30 | Moore Business Forms Inc | 9-(4-Aminophenyl polymethine)-9-xanthenol compounds and pressure sensitive system therewith |
US5079127A (en) * | 1982-04-06 | 1992-01-07 | Canon Kabushiki Kaisha | Optical recording medium and process for recording thereupon |
DE3608215A1 (en) * | 1986-03-12 | 1987-09-17 | Basf Ag | NEW BENZOPYRANS AND THEIR USE IN RECORDING SYSTEMS |
JPH0630626B2 (en) * | 1987-07-24 | 1994-04-27 | テルモ株式会社 | Indole productivity test reagent |
DE3724757A1 (en) * | 1987-07-25 | 1989-02-09 | Basf Ag | BENZOPYRAN DERIVATIVES |
GB8802237D0 (en) * | 1988-02-02 | 1988-03-02 | Shell Int Research | Detection of chemicals by immunoassay |
FR2650606B1 (en) * | 1989-08-07 | 1992-04-30 | Aussedat Rey | INFALSIFIABLE SECURITY PAPER AND AQUEOUS OR ORGANIC COMPOSITION USEFUL, IN PARTICULAR FOR MAKING PAPER INFALSIFIABLE |
DE4238994A1 (en) * | 1992-11-19 | 1994-05-26 | Basf Ag | Aniline as a marking agent for mineral oils |
-
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 SK SK51-97A patent/SK5197A3/en unknown
- 1995-07-03 CA CA002195019A patent/CA2195019A1/en not_active Abandoned
- 1995-07-03 BR BR9508401A patent/BR9508401A/en not_active Application Discontinuation
- 1995-07-03 HU HU9700062A patent/HUT76687A/en unknown
- 1995-07-03 WO PCT/EP1995/002558 patent/WO1996002613A1/en not_active Application Discontinuation
- 1995-07-03 KR KR1019970700194A patent/KR970704860A/en not_active Application Discontinuation
- 1995-07-03 CZ CZ9795A patent/CZ9597A3/en unknown
- 1995-07-03 EP EP95924960A patent/EP0770119A1/en not_active Withdrawn
- 1995-07-03 AU AU29263/95A patent/AU686838B2/en not_active Expired - Fee Related
- 1995-07-03 PL PL95318378A patent/PL318378A1/en unknown
- 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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KR970704860A (en) | 1997-09-06 |
BR9508401A (en) | 1998-05-19 |
AU2926395A (en) | 1996-02-16 |
CO4600746A1 (en) | 1998-05-08 |
NO970126L (en) | 1997-03-10 |
EP0770119A1 (en) | 1997-05-02 |
JPH10502693A (en) | 1998-03-10 |
BG101156A (en) | 1997-08-29 |
SK5197A3 (en) | 1997-08-06 |
FI970108A0 (en) | 1997-01-10 |
WO1996002613A1 (en) | 1996-02-01 |
MX9700365A (en) | 1997-04-30 |
TR199500823A2 (en) | 1996-06-21 |
NO970126D0 (en) | 1997-01-10 |
PL318378A1 (en) | 1997-06-09 |
DE4424712A1 (en) | 1996-01-18 |
IL114442A0 (en) | 1995-11-27 |
CZ9597A3 (en) | 1997-06-11 |
HUT76687A (en) | 1997-10-28 |
FI970108A (en) | 1997-03-12 |
AU686838B2 (en) | 1998-02-12 |
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