HUT76687A - Use of benzaldehydes to mark hydrocarbons - Google Patents
Use of benzaldehydes to mark hydrocarbons Download PDFInfo
- Publication number
- HUT76687A HUT76687A HU9700062A HU9700062A HUT76687A HU T76687 A HUT76687 A HU T76687A HU 9700062 A HU9700062 A HU 9700062A HU 9700062 A HU9700062 A HU 9700062A HU T76687 A HUT76687 A HU T76687A
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- benzaldehydes
- group
- hydroxy
- Prior art date
Links
- 150000003935 benzaldehydes Chemical class 0.000 title claims description 26
- 229930195733 hydrocarbon Natural products 0.000 title claims description 23
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 23
- -1 piperidino, morpholino Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002372 labelling Methods 0.000 claims description 7
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 6
- 239000000700 radioactive tracer Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 239000000243 solution Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002283 diesel fuel Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 5
- QOZQSTNLPIFIAO-UHFFFAOYSA-N 2-hydroxy-4-morpholin-4-ylbenzaldehyde Chemical compound C1=C(C=O)C(O)=CC(N2CCOCC2)=C1 QOZQSTNLPIFIAO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LWJPZHBPQCIYLV-UHFFFAOYSA-N [5-(dimethylamino)-2-formylphenyl] acetate Chemical compound CN(C)c1ccc(C=O)c(OC(C)=O)c1 LWJPZHBPQCIYLV-UHFFFAOYSA-N 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- MCPLVIGCWWTHFH-UHFFFAOYSA-L methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 244000172533 Viola sororia Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical group CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- DNRTTXXWWAKULZ-UHFFFAOYSA-N 3-(4-formyl-n-methylanilino)propanenitrile Chemical compound N#CCCN(C)C1=CC=C(C=O)C=C1 DNRTTXXWWAKULZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SKIKINWJMLIFFY-UHFFFAOYSA-N 4-(dibenzylamino)-2-hydroxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 SKIKINWJMLIFFY-UHFFFAOYSA-N 0.000 description 1
- SEMIDUTZXZKVAS-UHFFFAOYSA-N 4-(dibenzylamino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SEMIDUTZXZKVAS-UHFFFAOYSA-N 0.000 description 1
- FJBDMJZBYSCLLJ-UHFFFAOYSA-N 4-(diethylamino)-2-methoxybenzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(OC)=C1 FJBDMJZBYSCLLJ-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- KURCTZNCAHYQOV-UHFFFAOYSA-N 4-(dimethylamino)-2-hydroxybenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(O)=C1 KURCTZNCAHYQOV-UHFFFAOYSA-N 0.000 description 1
- ILJVPSVCFVQUAD-UHFFFAOYSA-N 4-piperidin-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCCCC1 ILJVPSVCFVQUAD-UHFFFAOYSA-N 0.000 description 1
- DATXHLPRESKQJK-UHFFFAOYSA-N 4-pyrrolidin-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCCC1 DATXHLPRESKQJK-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
- 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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BRZVVEDHPJOUHQ-UHFFFAOYSA-N OC(C1[ClH][ClH][ClH]C=CC=C1)=O Chemical compound OC(C1[ClH][ClH][ClH]C=CC=C1)=O BRZVVEDHPJOUHQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral 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
- XVQUOJBERHHONY-UHFFFAOYSA-N isometheptene Chemical group CNC(C)CCC=C(C)C XVQUOJBERHHONY-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 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
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
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- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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Description
A találmány tárgyát az (I) általános képletű benzaldehideknek a szénhidrogének megjelölésére való alkalmazása, eljárás a szénhidrogénekben ezeknek a benzaldehideknek a kimutatására, valamint a fenti benzaldehideket jelzőanyagként tartalmazó szénhidrogének képezik.The present invention relates to the use of benzaldehydes of the formula I for the labeling of hydrocarbons, to a method for the detection of these benzaldehydes in the hydrocarbons, and to the hydrocarbons containing the above benzaldehydes as tracers.
Az (I) általános képletben az A gyűrű egy benzolgyűrűvel lehet anellált,Ring A can be annealed with a benzene ring,
R , R és R jelentése egymástól függetlenül hidrogénatom, hidroxi-, ciano-, nitro-, 1-15 szénatomos alkil-, 1-15 szénatomos alkoxicsoport vagy egy -NR4R5 vagy -COOR6 általános képletű csoport, a képletekbenR, R and R are each independently hydrogen, hydroxy, cyano, nitro, (C 1 -C 15) alkyl, (C 1 -C 15) alkoxy, or -NR 4 R 5 or -COOR 6 in which:
R4 jelentése hidrogénatom vagy adott esetben fenilcsoporttal szubsztituált olyan 1-15 szénatomos alkilcsoport, amelyben a szénlánc folytonosságát 1-4 egymással nem szomszédos oxigénatom szakíthatja meg,R 4 is hydrogen or (C 1 -C 15) alkyl optionally substituted by phenyl, wherein the carbon chain continuity can be interrupted by 1 to 4 non-adjacent oxygen atoms,
R5 jelentése adott esetben fenilcsoporttal szubsztituált olyan 1-15 szénatomos alkilcsoport, amelyben a szénlánc folytonosságát 1-4 egymással nem szomszédos oxigénatom szakíthatja R5 is an optionally substituted phenyl group is a C1-15 alkyl, in which the continuity of the carbon chain is interrupted by 1 to 4 non-adjacent oxygen
2 , meg, vagy egy -L-NX X általános kepletű csoport, a képletben L jelentése 2-8 szénatomos alkiléncsoport és X1 és X2 jelentése egymástól függetlenül 1-6 szenatomos alkilcsoport, vagy X és X a közöttük levő nitrogénatommal együtt egy olyan 5 vagy 6 tagú telített heterociklusos csoportot képez, amely a gyűrűben heteroatomként még egy oxigénatomot is tartalmazhat, és2, meg, or a group of the formula -L-NX X wherein L is a C 2 -C 8 alkylene group and X 1 and X 2 are independently C 1 -C 6 alkyl or X and X together with the nitrogen atom between them are Forms a 5 or 6 membered saturated heterocyclic group which may even contain one oxygen atom as a heteroatom in the ring, and
R jelentése hidrogénatom, olyan 1-15 szénatomos alkilcsoport, amelyben a szénlánc folytonosságát 1-4 egymással nem szomszédos oxigénatom szakíthatja meg, vagy egy -L-NxX2 általános • · képletű csoport, a képletben L, X1 és X2 jelentése a fentiekben megadott.R is hydrogen, a C 1 -C 15 alkyl group in which the chain continuity may be interrupted by 1 to 4 non-adjacent oxygen atoms, or a group -L-NxX 2 wherein L, X 1 and X 2 are as defined above. specified.
Az US-A-5 145 573, US-A-5 182 372 valamint az EP-A-499 845 számú szabadalmi iratból olyan azoszínezékeket ismerünk, amelyek az ásványolajokban jelzőanyagokként szolgálnak. Továbbá olyan eljárást ismertet az US-A-4 009 008 számú szabadalmi irat az ásványolajoknak biszazoszínezékekkel való megjelölésére, amelynél az ásványolajhoz hozzáadott színezéket láthatóvá teszik, és amelynél a jelzett ásványolajhoz egy olyan adszorbeáló szert adnak, ami az ásványolajnak a többi színes alkotórészét megköti.US-A-5 145 573, US-A-5 182 372 and EP-A-499 845 disclose azo dyes which serve as tracers in mineral oils. Further, US-A-4 009 008 discloses a process for labeling mineral oils with bisazos dyes, wherein the colorant added to the mineral oil is visualized and wherein the mineral oil is adsorbed to the mineral oil to provide the other colored mineral constituents.
A DE-A-3 608 215 és a DE-A-3 724 757 számú szabadalmi irat benzo-pirán-származékokat valamint a megjelölési rendszerekben való felhasználásukat ismerteti.DE-A-3 608 215 and DE-A-3 724 757 describe benzopyran derivatives and their use in labeling systems.
A DE-A-3 608 215 számú szabadalmi irat 1. példája írja le metanolos közegben a 2,3-dimetil-benzo-pirilium-[ trikloro-cinkát(II)]-nak a 4-(dimetil-amino)-benzaldehiddel való reakcióját, az (A) képletű színezék képzésére.Example 1 of DE-A-3 608 215 describes the reaction of 2,3-dimethylbenzopyrilium trichlorocinate (II) with 4- (dimethylamino) benzaldehyde in methanol. reaction to form the dye of formula (A).
A szubsztituált anilineknek az ásványolajok megjelölésére való felhasználását a WO-A-11 466/1994 számú nyilvánosságra hozatali irat ismerteti.The use of substituted anilines for the labeling of mineral oils is described in WO-A-11466/1994.
A találmány célja az volt, hogy új jelzőanyagokat találjunk a szénhidrogének megjelölésére. Az új jelzőanyagoknak könnyen hozzáférhetőknek, a szénhidrogénekben jól oldhatóknak és egyszerű módon kimutathatóknak kell lenniük. Ennek során már nagyon kis mennyiségű jelzőanyagot erős színreakcióval láthatóvá kell tudnunk tenni.The object of the present invention was to find new tracers for the labeling of hydrocarbons. The new tracers should be readily available, highly soluble in hydrocarbons and easily detectable. In doing so, we need to be able to visualize very small amounts of tracer with a strong color reaction.
Azt találtuk, hogy a fentiekben definiált (I) általános kép• ·We have found that the above general image (I) • ·
letű benzaldehid-származékok előnyös jelzőanyagok a szénhidrogének megjelölésére.Benzaldehyde derivatives are preferred markers for hydrocarbon labeling.
Az (I) általános képletű vegyületek fenti definíciójában szereplő valamennyi alkil- és alkiléncsoport egyenes vagy elágazó szénláncú is lehet.All alkyl and alkylene groups in the above definition of compounds of formula (I) may be linear or branched.
22
Ha X és X a közöttük levő nitrogenatommal együtt egy olyan 5 vagy 6 tagú telített heterociklusos csoportot képez, amely a gyűrűben heteroatomként még egy oxigénatomot is tartalmazhat, úgy ez a heterociklusos csoport például 1-pirrolidinil-, piperidino- vagy morfolinocsoportot jelenthet.When X and X together with the nitrogen atom between them form a 5 or 6 membered saturated heterocyclic group which may even contain one oxygen atom as a heteroatom in the ring, this heterocyclic group may be, for example, 1-pyrrolidinyl, piperidino or morpholino.
R1, R“, R3, R4, R5, R6, X1 és X2 jelenthet például metil-, etil-, propil-, izopropil-, butil-, izobutil-, szek-butil-, pentil-, izopentil-, neopentil-, terc-pentil-, hexil- vagy 2-metil-pentilcsoportot.R 1 , R 4 , R 3 , R 4 , R 5 , R 6 , X 1 and X 2 may be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, , isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
R1, R2, R3, R4, R5 és R6 jelenthet továbbá például heptil-, oktil-, 2-etil-hexil-, izooktil-, nonil-, izononil-, decil-, izodecil-, undecil-, dodecil-, trídecil-, 3,5,5,7-tetrametil-nonil-, izotridecil-, tetradecil- vagy pentadecilcsoportot (a fentiek közül az izooktil-, izononil-, izodecil- és az izotridecilcsoport triviális elnevezések, amelyek az oxoszintézissel kapott alkoholok nevéből származnak — lásd ehhez az Ullmann' sR 1 , R 2 , R 3 , R 4 , R 5 and R 6 may also be, for example, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isonyl, decyl, isodecyl, undecyl, , dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl, tetradecyl or pentadecyl (the above being the trivial names of the isooctyl, isononyl, isodecyl and isotridecyl groups obtained by oxosynthesis). derived from the names of alcohols - see Ullmann's
Encyclopedia of Industrial Chemistry, 5. kiadás, Al köteténekEncyclopedia of Industrial Chemistry, 5th edition, Vol
290-293. valamint A10 kötetének 284. és 285. oldalát).290-293. and pages 284 and 285 of Volume A10).
R1, R2 és R3 jelenthet továbbá például metoxi-, etoxi-, propoxi-, izopropoxi-, butoxi-, izobutoxi-, szek-butoxi-, pentil-oxi-, izopentil-oxi-, neopentil-oxi-, terc-pentil-oxi-, hexil-oxi-, 2-metil-pentil-oxi-, heptil-oxi-, oktil-oxi-, 2·· ··· ·R 1 , R 2 and R 3 may also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tertiary pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, 2 ·· ··· ·
-etil-hexil-oxi-, izooktil-oxi-, nonil-oxi-, izononil-oxi-, decil-oxi-, izodecil-oxi-, undecil-oxi-, dodecil-oxi-, tridecil—oxi—, 3, 5,5,7-tetrametil-nonil-oxi-, izotridecil-oxi-, tetradecil-oxi- vagy pentadecil-oxicsoportot.-ethylhexyloxy, isooctyloxy, nonyloxy, isonyloxy, decyloxy, isodecyloxy, undecyloxy, dodecyloxy, tridecyloxy, 3, 5,5,7-tetramethylnonyloxy, isotridecyloxy, tetradecyloxy or pentadecyloxy.
R4 és R5 jelenthet továbbá például 2-metoxi-etil-, 2-etoxi-etil-, 2-propoxi-etil-, 2-izopropoxi-etil-, 2-butoxi-etil-, 2és 3-metoxi-propil-, 2- és 3-etoxi-propil-, 2- és 3-propoxi-propil-, 2- és 3-butoxi-propil-, 2- és 4-metoxi-butil-, 2- ésR 4 and R 5 may also be, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2 and 3-methoxypropyl; , 2- and 3-ethoxypropyl, 2- and 3-propoxypropyl, 2- and 3-butoxypropyl, 2- and 4-methoxybutyl, 2- and
4-etoxi-butil-, 2- és 4-propoxi-butí1-, 2- és 4-butoxi-butil-,4-ethoxybutyl, 2- and 4-propoxybutyl, 2- and 4-butoxybutyl,
3, 6-dioxa-heptil-, 3,6-, 3,7- és 4,7-dioxa-oktil-, 4,8-, 3,7- és3,6-dioxa-heptyl, 3,6-, 3,7- and 4,7-dioxaoctyl, 4,8-, 3,7- and
4,7-dioxa-nonil-, 4,8-dioxa-decil-, 3,6,8-trioxa-decil-, 3,6,9-trioxa-undecil-, 3,6,9, 12-tetraoxa-tridecil-, benzil- vagy 1és 2-fenil-etilcsoportot.4,7-dioxanonyl, 4,8-dioxa-decyl, 3,6,8-trioxa-decyl, 3,6,9-trioxa-undecyl, 3,6,9,12-tetraoxa tridecyl, benzyl or 1 and 2-phenylethyl.
L jelenthet például etilén-, trimetilén-, tetrametilén-, pentametilén-, hexametilén-, heptametilén-, oktametiléncsoportot vagy -CH (CH3) -CH2- és -CH (CH3) -CH (CH3) - képletű csoportot.L can be, for example, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene or -CH (CH 3 ) -CH 2 - and -CH (CH 3 ) -CH (CH 3 ) -.
A találmány szerinti módon előnyösen olyan (I) általános képletű benzaldehid-származékokat alkalmazunk, amelyek képletében R1-R3 csoportok közül legalább az egyik egy -NR4R5 általános képletű csoportot jelent, a képletben R4 és R5 a fentiekben megadott jelentésűek.Preferably, benzaldehyde derivatives of formula (I) wherein at least one of R 1 -R 3 is a group -NR 4 R 5 , wherein R 4 and R 5 are as defined above, are preferably used in the process of the invention. .
Különösen előnyösen használjuk a szénhidrogének megjelölésére az (la) általános képletű benzaldehideket, a képletben R1, R2, R es R jelentese a fentiekben megadott.Particular preference is given to the use of benzaldehydes of formula (Ia) for the hydrocarbons, wherein R 1 , R 2 , R and R are as defined above.
Különösen alkalmasak azok az (la) általános képletű benzaldehidek, amelyek képleteben R es R jelentése egymástól függetlenül hidrogénatom, hidroxi-, 1-15 szénatomos alkil-, 1-15 szén6 atomos alkoxicsoport vagy egy -COOR6 általános képletű csoport, a képletben R6 a fentiekben megadott jelentésű, R4 jelentése hidrogénatom vagy 1-15 szénatomos alkilcsoport és R5 jelentése 1-15 szénatomos alkilcsoport.Particularly suitable are benzaldehydes of formula Ia wherein R and R are independently hydrogen, hydroxy, C 1 -C 15 alkyl, C 1 -C 15 alkoxy, or a -COOR 6 group in which R 6 R 4 is hydrogen or C 1 -C 15 alkyl and R 5 is C 1 -C 15 alkyl as defined above.
Különösen előnyösen használjuk a szénhidrogének megjelölésére azokat az (la) általános képletű benzaldehideket, amelyek képletében R4 és R5 jelentése egymástól függetlenül 1-13 szénatomos alkilcsoport, valamint R es R jelentése hidrogénatom.Particularly preferred hydrocarbons are those benzaldehydes of formula (Ia) wherein R 4 and R 5 are independently C 1 -C 13 alkyl and R and R are hydrogen.
A találmány tárgyát képezi továbbá a szénhidrogénekben az (I) általános képletű benzaldehidek jelenlétének a kimutatására szolgáló eljárás is, amelynél a szénhidrogént egy olyan vizes-alkoholos vagy alkoholos közeggel kezeljük, amely egy protonsavat, a (II) általános képletű szubsztituált benzo-piriliumsók — a képletben R7 jelentése 1-8 szénatomos alkil-, fenil-, 1-5 szénatomos alkoxicsoport vagy halogénatom, R jelentése metilcsoportThe present invention also relates to a method for detecting the presence of benzaldehydes of formula I in hydrocarbons by treating the hydrocarbon with an aqueous-alcoholic or alcoholic medium which is a protonic acid, the substituted benzopyrilium salts of formula II - a. wherein R 7 is C 1 -C 8 alkyl, phenyl, C 1 -C 5 alkoxy, or halogen, R is methyl
8 vagy R és R együtt egy tetrametiléncsoportot képez, és a B gyűrű egy benzolgyűrűvel lehet anellált, és a vegyületet adott esetben 1-4 szénatomos alkil-, 1-pirrolidinil-, piperidino-, morfolinocsoport, klór- vagy brómatom vagy a gyűrű 7-es helyzetében adott esetben még hidroxi-, 1-4 szénatomos alkoxi-, az alkilrészben 1-5 szénatomos mono- vagy dialkil-aminocsoport is szubsztituálhatja, amely maga is klóratommal vagy fenilcsoporttal lehet szubsztituált, és X tetszőleges aniont jelent — és/vagy a (III) általános képletű i.ndolok — a képletben R9 és R10 egymástól függetlenül hidrogén-, halogénatomot, egy -NR4R5 általános képletű csoportot, a képletben R4 és R5 a fentiekben megadott jelentésűek, hidroxi-, 1-8 szénatomos alkil-, fenil- vagy • ·Or R and R together form a tetramethylene group, and ring B can be annealed with a benzene ring, and the compound is optionally C 1 -C 4 alkyl, 1-pyrrolidinyl, piperidino, morpholino, chloro or bromo, or is optionally further substituted by hydroxy, (C1-C4) alkoxy, (C1-C5) mono- or dialkylamino in the alkyl moiety, which itself may be substituted by chlorine or phenyl, and X represents any anion, and / or Indoles of formula III: wherein R 9 and R 10 are independently hydrogen, halo, a group -NR 4 R 5 , wherein R 4 and R 5 are as defined above, hydroxy, 1-8. alkyl, phenyl, or • ·
1-5 szénatomos alkoxicsoportot jelent — közül legalább egy vegyületet és adott esetben egy cink-, alumínium- vagy ón-halogenidet tartalmaz.It represents at least one compound and optionally one zinc, aluminum or tin halide.
A találmány szerinti eljáráshoz előnyösen a (III) általános képletű indolokat, főleg a 2-fenil-indolt alkalmazzuk.The indoles of the formula (III), in particular 2-phenylindole, are preferably used in the process of the invention.
Az alkalmas X anion jelenthet például halogenid, szulfát,Suitable anions X include, for example, halide, sulfate,
A találmány szerinti értelemben vett megjelölés alatt azt értjük, hogy az (I) általános képletű benzaldehideket olyan koncentrációban adjuk a szénhidrogénekhez, hogy a szénhidrogének az emberi szem számára egyáltalán nem vagy csak alig láthatóan színeződjenek el, míg az (I) általános képletű benzaldehidek az alábbiakban részletezett módszerek segítségével könnyen és jól láthatóan detektálhatóak legyenek.In the context of the present invention, it is understood that benzaldehydes of formula (I) are added to the hydrocarbons in such a concentration that the color of the hydrocarbons is not or only slightly visible to the human eye, while the benzaldehydes of formula (I) they can be easily and visibly detected by detailed methods.
A találmány tárgyát képezik végül az egy vagy több (I) általános képletű benzaldehidet jelzőanyagként tartalmazó szénhidrogének is.Finally, the present invention also relates to hydrocarbons containing one or more benzaldehyde (I) as a tracer.
A találmány szerinti értelemben szénhidrogének alatt azokat az alifás vagy aromás szénhidrogéneket értjük, amelyek normális körülmények között folyékony halmazállapotúak. Ezek főleg az ásványolajok, például az üzemanyagok, így a benzin, kerozin vagy a dízelolaj, vagy az olajok, így a fűtőolaj vagy a motorolajok.In the context of the present invention, hydrocarbons are aliphatic or aromatic hydrocarbons which are normally liquid. These are mainly mineral oils such as fuels such as gasoline, kerosene or diesel oil, or oils such as fuel oil or motor oils.
Az (I) általános képletű benzaldehidek különösen az olyan • · · ásványolajok megjelölésére alkalmasak, amelyeknél például adózási okokból követelmény a megjelölés. Ahhoz, hogy a megjelölés költségeit alacsony szinten tarthassuk, arra kell törekednünk, hogy a megjelöléshez a jelzőanyagot a lehető legkisebb mennyiségben alkalmazzuk.The benzaldehydes of the formula I are particularly suitable for the designation of mineral oils which, for example, are required for tax purposes. In order to keep the cost of marking low, we need to try to use as little markup as possible on the mark.
A szénhidrogének megjelölésére az (I) általános képletű benzaldehideket vagy magukban, vagy oldatuk formájában alkalmazzuk.The hydrocarbons are designated by the benzaldehydes of formula (I) either alone or in solution.
Erre a célra oldószerként szerepelhetnek a szerves oldószerek, előnyösen az aromás szénhidrogének, így a toluol, xilol, dodecil-benzol, diizopropil-naftalin vagy a nagyobb móltömegű aromás vegyületek elegye, ami a kereskedelemben Shellsol AB néven kapható (a Shell cég terméke). Ahhoz, hogy a kapott oldat nagy viszkozitását elkerülhessük, az (I) általános képletű benzaldehideknek az oldatra vonatkoztatott koncentrációját általábanSuitable solvents for this purpose are organic solvents, preferably aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a higher molecular weight aromatic compound commercially available as Shellsol AB (a product of Shell). In order to avoid the high viscosity of the resulting solution, the concentration of benzaldehydes of formula I in the solution is generally
5-80 tömegszázalékosnak választjuk meg.5-80% by weight.
Az oldhatóság javításához még további koszolvenseket is alkalmazhatunk, például alkoholokat, így metanolt, etanolt, propanolt, izopropanolt, butanolt, izobutanolt, pentanolt, hexanolt, heptanolt, oktanolt, 2-etil-hexanolt vagy ciklohexanolt, glikolokat, így butil-etilénglikolt vagy metil-propilénglikolt, aminokat, így trietil-amint, diizooktil-amint, diciklohexil-amint, anilint, N-metil-anilint, N,N-dimetil-anilint, toluidint vagy xilidint, alkanol-aminokat, így 3-(2-metoxi-etoxi)-propil-amint, krezolokat, így az ο-, m- vagy p-krezolt, ketonokat, így dietil-ketont vagy ciklohexanont, laktonokat, így γ-butirolaktont, karbonátokat, így etilén- vagy propilén-karbonátot, fenolokat, így terc-butil- vagy nonil-fenolt, észtereket, így dimetil-, die9Other co-solvents may also be used to improve solubility such as alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol, glycols such as butyl ethylene glycol or methyl propylene glycol, amines such as triethylamine, diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N, N-dimethylaniline, toluidine or xylidine, alkanolamines such as 3- (2-methoxyethoxy) ) -propylamine, cresols such as ο-, m- or p-cresol, ketones such as diethyl ketone or cyclohexanone, lactones such as γ-butyrolactone, carbonates such as ethylene or propylene carbonate, phenols such as tertiary butyl or nonylphenol, esters such as dimethyl, die
til-, di(2-etil-hexil)-ftalátot, etil-, butil- vagy ciklohexil-acetátot, savamidokat, így N,N-dimetil-formamidot, N,N-dietil-acetamidot vagy N-metil-pirrolidinont vagy ezek elegyeit.ethyl, di (2-ethylhexyl) phthalate, ethyl, butyl or cyclohexyl acetate, acid amides such as N, N-dimethylformamide, N, N-diethylacetamide or N-methylpyrrolidinone or mixtures.
A találmány szerinti módon alkalmazni kívánt (I) általános képletű benzaldehidekkel nagyon egyszerűen ki tudjuk mutatni a jelzett szénhidrogéneket, még akkor is, ha bennük a jelzőanyag koncentrációja körülbelül 10 ppm vagy ennél is kisebb.The benzaldehydes of formula (I) to be used in the process of the present invention are very easy to detect labeled hydrocarbons, even if they have a tracer concentration of about 10 ppm or less.
A szénhidrogénekben a jelzőanyagként használt (I) általános képletű vegyületek jelenlétét előnyösen úgy mutatjuk ki, hogy a szénhidrogént egy olyan vizes-alkoholos vagy alkoholos közeggel kezeljük, amely egy (II) általános képletű piriliumsót és/vagy egy (III) általános képletű indolt, egy protonsavat és adott esetben egy cink-, alumínium- vagy ón-halogenidet tartalmaz. A vizes-alkoholos közeg alkalmazása esetén a víz:alkohol tömegarány értéke 0,5:1-től 4:1-ig terjed, előnyösen azonban körülbelül 1:1. Ez a vizes-alkoholos fázis jól látható színváltozását okozza.Preferably, the presence of the compounds of formula (I) used as tracers in the hydrocarbons is achieved by treating the hydrocarbon with an aqueous-alcoholic or alcoholic medium which comprises a pyrilium salt of formula (II) and / or an indole of formula (III) proton acid and optionally a zinc, aluminum or tin halide. When used in an aqueous-alcoholic medium, the weight ratio of water to alcohol is 0.5: 1 to 4: 1, but preferably about 1: 1. This causes a clear color change in the aqueous-alcoholic phase.
Erre a célra alkalmas alkohol például az etanol, propanol, izopropanol, l-metoxi-propán-2-ol, etilénglikol, propilénglikol vagy az 1,3-propándiol. Előnyös az etanol alkalmazása.Examples of suitable alcohols are ethanol, propanol, isopropanol, 1-methoxypropan-2-ol, ethylene glycol, propylene glycol or 1,3-propanediol. Ethanol is preferred.
A találmány szerinti eljáráshoz alkalmas protonsavak főleg az úgynevezett erős savak, azaz az olyan protonsavak, amelyeknél pKa < 3,5. Ilyen savakként szerepelhetnek például a szervetlen és a szerves savak, így a perklórsav, hidrogén-jodid, sósavgáz, hidogén-bromid, hidrogén-fluorid, kénsav, salétromsav, foszforsav, benzolszulfonsav, toluolszulfonsav, naftalinszulfonsav, metánszulf onsav, oxálsav, maleinsav, klór-ecetsav, dl klór-ecetsav • · · · vagy a bróm-ecetsav. Néhány esetben előnyös lehet ezeket a savakat például ecetsav hozzáadásával lepufferolni.Suitable for the invention are mainly the so-called strong protonic acid, such as a proton, wherein pK a <3.5. Examples of such acids include inorganic and organic acids such as perchloric acid, hydrogen iodide, hydrochloric acid gas, hydrobromic acid, hydrogen fluoride, sulfuric acid, nitric acid, phosphoric acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, methanesulfonic acid, acetic acid, dl chloroacetic acid or · bromoacetic acid. In some cases, it may be advantageous to buffer these acids by, for example, adding acetic acid.
Az o- vagy p-toluolszulfonsav mellett különösen a szervetlen savak az előnyösek, és ezek közül is főleg a sósav vagy a kénsav .In addition to o- or p-toluenesulfonic acid, inorganic acids are particularly preferred, and in particular hydrochloric or sulfuric acid.
Az alkalmas cink-, alumínium- és ón-halogenidek közé tartozik például a cink(II)-klorid, cink(II)-bromid, alumínium(III)-klorid, alumínium(III)-bromid vagy az ón-tetraklorid. Különösen előnyös a cink(II)-klorid.Suitable zinc, aluminum and tin halides include, for example, zinc (II) chloride, zinc (II) bromide, aluminum (III) chloride, aluminum (III) bromide or tin tetrachloride. Zinc (II) chloride is particularly preferred.
Az oldathoz adott esetben egy fém-halogenidet is adva, egy (II) általános képletű benzo-piriliumsó és/vagy egy (III) általános képletű indol és egy protonsav vizes-alkoholos vagy alkoholos oldatának 1-50 milliliterét általában elegendő a találmány szerinti módon megjelölt szénhidrogénnek körülbelül 10-50 milliliterével kirázni ahhoz, hogy színváltozást kapjunk. Úgy is eljárhatunk azonban, hogy a protonsav oldata helyett csak a fém-halogenid vizes-alkoholos oldatát használjuk, mivel ez szintén savas kémhatású.The addition of a metal halide optionally to the solution, from 1 to 50 milliliters of an aqueous alcoholic or alcoholic solution of a benzopyrilium salt of the formula II and / or an indole of the formula III and a protonic acid, is generally sufficient according to the invention. shake with about 10 to 50 milliliters of hydrocarbon to obtain a color change. However, it is also possible to use only an aqueous alcoholic solution of the metal halide instead of the protonic acid solution since it is also acidic.
A protonsav koncentrációja a vizes-alkoholos vagy alkoholos oldatban általában 5-50, előnyösen 10-30 tömegszázalék. A fém-halogenid koncentrációja általában 0-50, előnyösen 5-20 tömegszázalék, mindig az oldat tömegére vonatkoztatva.The concentration of protonic acid in the aqueous-alcoholic or alcoholic solution is generally 5 to 50, preferably 10 to 30% by weight. The concentration of metal halide is generally from 0 to 50%, preferably from 5 to 20% by weight, always based on the weight of the solution.
A találmány szerinti eljárásnak az a nagy előnye van, hogy két különböző módszert tud használni az (I) általános képletű benzaldehidek kimutatására. Ezért a kimutatást nagyon megbízhatóan lehet végrehajtani, még az esetleges zavaró tényezők (például adalékok a dízelolajban) ellenére is.The inventive method has the great advantage of being able to use two different methods for the detection of benzaldehydes of formula (I). Therefore, the detection can be carried out with high reliability, even though there may be confounding factors (such as additives in diesel).
• »· ·· ·· ··♦· ··» ···· * » ·«> · · k · k «·* «· «» · * · ·• »· · · · · · · · · · · · · · · · · · · · · · · · · · · · ·
Példák a találmány szerinti eljárás alkalmazására:Examples of the method of the invention:
1. általános előirat:General rule 1:
A kereskedelemben szokásosan kapható dízelolajhoz a benzaldehidet mindig 10 ppm koncentrációban adjuk hozzá. Ebből a célból elkészítjük a benzaldehidnek 0,1 tömegszázalékos toluolos oldatát, és ezt az oldatot adjuk a dízelolajhoz.Benzaldehyde is always added to commercially available diesel at a concentration of 10 ppm. For this purpose, a 0.1 wt% solution of benzaldehyde in toluene is prepared and this solution is added to the diesel oil.
Az alábbi 1-12. példában az így jelzett dízelolajból mindig milliliterhez adunk 2 ml reagensoldatot, és ezt a reakcióelegyet 5 percig rázzuk. Ezután a reakcióelegyhez adunk 1 ml vizet, és a reakcióelegyet még 5 percig rázzuk. A vizes fázis az alábbi1-12 below. In Example 1, 2 ml of reagent solution are always added to milliliters of the so-called diesel oil and the reaction mixture is shaken for 5 minutes. Water (1 ml) was added and the reaction mixture was shaken for a further 5 minutes. The aqueous phase is as follows
1. táblázatban megadott színt mutatja.Shows the color specified in Table 1.
1. reagensoldat összetétele:Composition of reagent solution 1:
indol 1 tömegszázalékos etanolos oldata 5 ml tömény sósav 5 ml cink(II)-klorid 5 g ecetsav 95 ml1% solution of indole in ethanol by weight 5 ml concentrated hydrochloric acid 5 ml zinc (II) chloride 5 g acetic acid 95 ml
2. reagensoldat összetétele:Composition of reagent solution 2:
2-metil-indol 1 tömegszázalékos etanolos oldata 5 ml tömény sósav 5 ml cink(II)-klorid 5 g ecetsav 95 ml1% (w / w) solution of 2-methylindole in ethanol 5 ml concentrated hydrochloric acid 5 ml zinc (II) chloride 5 g acetic acid 95 ml
3. reagensoldat összetétele:Composition of reagent solution 3:
2-fenil-indol 1 tömegszázalékos etanolos oldata 5 ml tömény sósav 5 ml cink(II)-klorid 5 g ecetsav 95 ml1% (w / w) solution of 2-phenylindole in ethanol 5 ml concentrated hydrochloric acid 5 ml zinc (II) chloride 5 g acetic acid 95 ml
A találmány szerinti eljárást különösen előnyösen úgy hajt» « »·♦ ·It is particularly advantageous to carry out the process according to the invention.
,...,...·..... ... .. ·
juk végre, hogy a dízelolajat a vizsgálat előtt Kieselgel tölteten át megszűrjük.finally, filter the diesel oil through a Kieselgel filler before testing.
1. táblázatTable 1
A találmány szerinti eljárást hasonlóan kedvező módon hajthatjuk végre, ha az eljárásban jelzőanyagként az alábbi 2. táblázatban felsorolt benzaldehideket alkalmazzuk.The process of the present invention may be similarly advantageously carried out using the benzaldehydes listed in Table 2 below as tracers.
«•e -»* *» »*·«• e -» * * »» * ·
2. táblázatTable 2
. általános előirat. general prescription
A kereskedelemben szokásosan kapható dízelolajhoz a benzaldehidet mindig 10 ppm koncentrációban adjuk hozzá. Ebből a célból elkészítjük a benzaldehidnek 0,1 tömegszázalékos toluolos oldatát, és ezt az oldatot adjuk a dízelolajhoz.Benzaldehyde is always added to commercially available diesel at a concentration of 10 ppm. For this purpose, a 0.1 wt% solution of benzaldehyde in toluene is prepared and this solution is added to the diesel oil.
Az alábbi 21-30. példában az így jelzett dízelolajból mindig milliliterhez adunk 2 ml 4. reagensoldatot, és ezt a reakcióelegyet 5 percig visszafolyató hűtő alatt forraljuk. Ezután a reakcióelegyhez adunk a víznek és etanolnak 1:1 térfogatarányú elegyéből 1 ml-t, és a reakcióelegyet 5 percig rázzuk. A vizes fázis az alábbi 3. táblázatban megadott színt mutatja.21 to 30 below. In Example 1, 2 ml of reagent solution 4 are always added to milliliters of the so-called diesel oil and the reaction mixture is refluxed for 5 minutes. Then, 1 ml of a 1: 1 mixture of water and ethanol (v / v) was added to the reaction mixture and the reaction mixture was shaken for 5 minutes. The aqueous phase shows the color shown in Table 3 below.
4. reagensoldat összetétele:Composition of reagent solution 4:
(Ha) általános képletű benzo-piriliumsó tömegszázalékos vizes oldata 5 ml tömény sósav 25 ml ecetsavAqueous solution of benzopyrilium salt of formula Ha in 5% by weight of concentrated hydrochloric acid 25 ml of acetic acid
225 ml • · • a · ·225 ml • · • a · ·
3. táblázatTable 3
A találmány szerinti eljárást hasonlóan kedvező módon hajthatjuk végre, ha a 4. reagensoldatban a (Ila) általános képletű benzo-piriliumsót (IV) képletű vegyülettel helyettesítjük.The process of the present invention can be similarly advantageously carried out by replacing the benzopyrilium salt of formula IIa in reagent solution 4 with a compound of formula IV.
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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 |
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