JPH10502693A - Use of benzaldehyde to mark hydrocarbons - Google Patents
Use of benzaldehyde to mark hydrocarbonsInfo
- Publication number
- JPH10502693A JPH10502693A JP8504633A JP50463396A JPH10502693A JP H10502693 A JPH10502693 A JP H10502693A JP 8504633 A JP8504633 A JP 8504633A JP 50463396 A JP50463396 A JP 50463396A JP H10502693 A JPH10502693 A JP H10502693A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- benzaldehyde
- hydrogen
- 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.)
- Pending
Links
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 25
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 23
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 239000003550 marker Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003935 benzaldehydes Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 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
- -1 1,4-butylene Chemical group 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000001875 compounds Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 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
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- UNQLRWBLUDHEDR-UHFFFAOYSA-N morpholin-4-yl-piperidin-1-yl-pyrrolidin-1-yl-lambda3-chlorane Chemical compound N1(CCCC1)Cl(N1CCOCC1)N1CCCCC1 UNQLRWBLUDHEDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 abstract description 2
- 101710088194 Dehydrogenase Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002283 diesel fuel Substances 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 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
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- BXKKSMQQZTWOII-UHFFFAOYSA-L zinc;acetic acid;dichloride Chemical compound [Cl-].[Cl-].[Zn+2].CC(O)=O BXKKSMQQZTWOII-UHFFFAOYSA-L 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance 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
- 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 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 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
- 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
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 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
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KLHYPYAETJWSBK-UHFFFAOYSA-J Cl[Zn](Cl)(Cl)Cl Chemical class Cl[Zn](Cl)(Cl)Cl KLHYPYAETJWSBK-UHFFFAOYSA-J 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- 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
- 229930188620 butyrolactone Natural products 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 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
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
- 238000002372 labelling Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-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
- 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
- 235000006408 oxalic acid Nutrition 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
- 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
- 125000004193 piperazinyl group Chemical group 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
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
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- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
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- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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- C10M171/007—Coloured or dyes-containing lubricant compositions
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
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Abstract
(57)【要約】 炭化水素用マーキング剤として式 [式中環Aはベンゾ環付加されていてもよく、かつR1、R2およびR3は水素、ヒドロキシ、C1〜C15アルキル、C1〜C15アルコキシ、シアノ、ニトロまたは式NR4R5またはCOOR6の基を表わし、ここでR4は水素または場合により置換されたC1〜C15アルキルを表わし、R5は場合により置換されたC1〜C15アルキルまたは式L−NX1X2(LはC2〜C8アルキレンの意味を有し、X1およびX2は互いに独立にその都度C1〜C6アルキルの意味を有するかまたはそれの結合している窒素原子と一緒に複素環基の意味を有する)の基を表わし、かつR6は水素、場合により置換されたC1〜C15アルキルを表わすかまたは式L−NX1X2(L、X1およびX2はその都度上記の意味を有する)の基を表わす]のベンズアルデヒドの使用、炭化水素中のこれらベンズアルデヒドを検出する方法ならびに上記ベンズアルデヒドを含有する炭化水素。 (57) [Summary] Formula as a marking agent for hydrocarbons [Wherein ring A may be benzo ring-added and R 1 , R 2 and R 3 are hydrogen, hydroxy, C 1 -C 15 alkyl, C 1 -C 15 alkoxy, cyano, nitro or formula NR 4 R 5 or COOR 6 , wherein R 4 represents hydrogen or optionally substituted C 1 -C 15 alkyl, and R 5 is optionally substituted C 1 -C 15 alkyl or formula L-NX 1 X 2 (L has the meaning of C 2 -C 8 alkylene, X 1 and X 2 independently of one another each have the meaning of C 1 -C 6 alkyl or together with the nitrogen atom to which it is attached Has the meaning of a heterocyclic group, and R 6 represents hydrogen, optionally substituted C 1 -C 15 alkyl or of the formula L-NX 1 X 2 (L, X 1 and X 2 In each case has the above meaning). The use of dehydrogenase, methods and hydrocarbons containing the benzaldehyde detecting these benzaldehydes in hydrocarbons.
Description
【発明の詳細な説明】 炭化水素をマーキングするためのベンズアルデヒドの使用 本発明は、炭化水素のマーキング剤としての式I [式中 環Aはベンゾ環付加されていてもよく、 R1、R2およびR3は互いに独立にそれぞれ水素、ヒドロキシ、C1〜C15アルキ ル、C1〜C15アルコキシ、シアノ、ニトロまたは式NR4R5またはCOOR6を 表わし、ここで R4は水素または、エーテル官能性酸素原子1〜4個により中断されていて もよくかつ場合によりフェニルによって置換されているC1〜C15アルキルを表 わし、 R5はエーテル官能性酸素原子1〜4個により中断されていてもよくかつ場 合によりフェニルにより置換されているC1〜C15アルキル、または式L−NX1 X2(LはC2〜C8アルキレンの意味を有し、X1およびX2は互いに独立にその 都度C1 〜C6アルキルの意味を有するかまたはそれの結合している窒素原子と一緒に、 環中になお酸素原子を含有することのできる5員または6員の飽和複素環基の意 味を有し、かつ R6は水素、エーテル官能性酸素原子1〜4個により中断されていてもよい C1〜C15アルキルを表わすか、または式L−NX1X2(L、X1およびX2はそ れぞれ上記の意味を有する)の基を表わす]のベンズアルデヒドの使用、炭化水 素中のこれらベンズアルデヒドを検出する方法、ならびに上記ベンズアルデヒド を含有する炭化水素に関する。 米国特許(US−A)5145573号、米国特許(US−A)518237 2号ならびにヨーロッパ特許(EP−A)499845号から、鉱油のマーキン グ剤として使用されるアゾ染料は既に公知である。さらに米国特許(US−A) 4009008号には、ジスアゾ染料を用いて鉱油をマーキングする方法が記載 され、該方法においては鉱油に添加された染料を、鉱油の他の有色成分を結合す る吸着剤をマーキングされた鉱油に添加することにより目に見えるようにする。 ドイツ国特許(DE−A)3608215号およびドイツ国特許(DE−A) 3724757号には、ベンゾピラン誘導体ならびに表示系におけるその使用が 記載されている。 ドイツ国特許(DE−A)3608215号の例1 には、メタノール中での、式 の色素塩の生成下に、2,3−ジメチルベンゾピリリウム−トリクロロ亜鉛酸塩 と4−ジメチルアミノベンズアルデヒドとの反応が記載されている。 PCT特許(WO−A11466/1994号)には、鉱油をマーキングする ために置換アニリンの使用が記載されている。 本発明の課題は、炭化水素の新規マーキング剤を提供することである。新規マ ーキング剤は容易に入手できかつ炭化水素に良溶性であるべきである。さらに、 該マーキング剤は簡単に検出することができるべきである。その際、なお極めて 少量のマーキング剤でさえ、強い呈色反応により目に見えるようにすることがで きるべきである。 それにより、冒頭に詳細に表示した式Iのベンズアルデヒドは炭化水素のマー キング剤として適当であることが見出された。 上記の式I中に現れるすべてのアルキル基およびアルキレン基は、直鎖であっ ても分枝鎖であってもよい。 X1およびX2がそれの結合している窒素原子と一緒に、環中になお1個の酸素 原子を含有することのでき る5員または6員の飽和複素環基を表わす場合、これにはたとえばピロリジニル 、ピペラジニルまたはモルホリニルを挙げることができる。 基R1、R2、R3、R4、R5、R6、X1およびX2は、たとえばメチル、エチル 、プロピル、イソプロピル、ブチル、イソブチル、sec−ブチル、ペンチル、 イソペンチル、ネオペンチル、tert−ペンチル、ヘキシルまたは2−メチル ペンチルである。 さらに、基R1、R2、R3、R4、R5およびR6はたとえばヘプチル、オクチル 、2−エチルヘキシル、イソオクチル、ノニル、イソノニル、デシル、イソデシ ル、ウンデシル、ドデシル、トリデシル、3,5,5,7−テトラメチルノニル 、イソトリデシル、テトラデシルまたはペンタデシルである(上記の名称イソオ クチル、イソノニル、イソデシルおよびイソトリデシルは慣用名称であり、オキ ソ合成により得られるアルコールから由来する−これについてはUllmnn′ s Encyclopedia of Industrial Chemist ry、5版、A1巻、290〜293ページ、ならびにA1O巻、284および 285ページ参照)。 さらに、基R1、R2およびR3は、たとえばメトキシ、エトキシ、プロポキシ 、イソプロポキシ、ブトキシ、イソブトキシ、sec−ブトキシ、ペンチルオキ シ、イソペンチルオキシ、ネオペンチルオキシ、te rt−ペンチルオキシ、ヘキシルオキシ、2−メチルペンチルオキシ、ヘプチル オキシ、オクチルオキシ、2−エチルヘキシルオキシ、イソオクチルオキシ、ノ ニルオキシ、イソノニルオキシ、デシルオキシ、イソデシルオキシ、ウンデシル オキシ、ドデシルオキシ、トリデシルオキシ、3,5,5,7−テトラメチルノ ニルオキシ、イソトリデシルオキシ、テトラデシルオキシまたはペンタデシルオ キシである。 さらに、基R4およびR5はたとえば2−メトキシエチル、2−エトキシエチル 、2−プロポキシエチル、2−イソプロポキシエチル、2−ブトキシエチル、2 −または3−メトキシプロピル、2−または3−エトキシプロピル、2−または 3−プロポキシプロピル、2−または3−ブトキシプロピル、2−または4−メ トキシブチル、2−または4−エトキシブチル、2−または4−プロポキシブチ ル、2−または4−ブトキシブチル、3,6−ジオキサヘプチル、3,6−ジオ キサオクチル、4,8−ジオキサノニル、3,7−ジオキサオクチル、3,7− ジオキサノニル、4,7−ジオキサオクチル、4,7−ジオキサノニル、4,8 −ジオキサデシル、3,6,8−トリオキサデシル、3,6,9−トリオキサウ ンデシル、3,6,9,12−テトラオキサトリデシル、ベンジルまたは1−ま たは2−フェニルエチルである。 基Lは、たとえば(CH2)2、(CH2)3、(CH2 )4、(CH2)5、(CH2)6、(CH2)7、(CH2)8、(CH(CH3)C H2またはCH(CH3)CH(CH3)である. 本発明により好ましくは、基R1〜R3の少なくとも1つが式NR4R5(式中R4 およびR5はそれぞれ上記の意味を有する)の基を表す式Iのベンズアルデヒド が使用される。 殊に好ましくは、炭化水素のマーキングのために、式Ia [式中R1、R2、R4およびR5は上記の意味を有する]のベンズアルデヒドがに 使用される。 殊に適当なのは、R1およびR2が互いに独立にその都度水素、ヒドロキシ、C1 〜C15アルキル、C1〜C15アルコキシまたは式COOR6(R6は上記の意味を 有する)の基を表わし、R4は水素またはC1〜C15アルキルを表わしかつR5は C1〜C15アルキルを表わす式Iaのベンズアルデヒドである。 殊に好ましくは、炭化水素をマーキングするために、R4およびR5が互いに独 立にその都度C1〜C13アルキルを表わし、ならびにR1およびR2がその都度水 素を表わす式Iaのベンズアルデヒドが使用される。 さらに、本発明の対象は炭化水素中の式Iのベンズアルデヒドの存在を検出す る方法であり、その際炭化水素を、プロトン酸、式II [式中R7はC1〜C8アルキル、フェニル、C1〜C5アルコキシまたはハロゲン を表わし、R8はメチルを表わすかまたはR7およびR8は一緒に1,4−ブチレ ンを表わし、環Bはベンゾール環により環付加されていてもよくかつ場合により C1〜C4アルキル、ピロリジノ、ピペリジノ、モルホリノ、塩素または臭素によ り置換されているかまたは環7位が場合によりヒドロキシ、C1〜C4アルコキシ 、C1〜C5モノ−またはジアルキルアミノ(その都度再び塩素またはフェニルに より置換されていてもよい)により置換されていて、X-は任意のアニオンを表 わす]の置換ベンゾピリリウム塩、および式III [式中R9およびR10は互いに独立にその都度水素、ヒドロキシ、式NR4R5( R4およびR5はその都度上記の意味を有する)の基、C1〜C8アルキル、フェニ ル、C1〜C5アルコキシまたはハロゲンを表わす]の インドールからなる化合物群からの少なくとも1つの化合物および場合により金 属亜鉛、アルミニウムまたはスズのハロゲン化物を含有する水−アルコール媒体 またはアルコール媒体で処理する。 好ましくは、本発明により式IIIのインドール、殊に2−フェニルインドー ルが使用される。 適当なアニオンX-の例は、テトラクロロ亜鉛酸塩、ハロゲン化物、硫酸塩、 テトラフルオロホウ酸塩またはリン酸塩である。 ベンズアルデヒドI、ベンゾピリリウム塩IIならびにインドールIIIは通 例自体公知である。 本発明による意味でのマーキングとは、式Iのベンズアルデヒドを炭化水素に 特定の濃度で添加し、これにより炭化水素は人間の目に全く見えないかまたは殆 ど見えない程度に着色されているが、その際式Iのベンズアルデヒドはここに詳 述した検出方法により容易かつ明瞭に見えて検出可能であるようにすることであ る。 本発明の他の対象は、式Iのベンズアルデヒド1種または数種を含有する炭化 水素である。本発明による意味での炭化水素は、標準状態で液状の凝集状態で存 在する脂肪族または芳香族炭化水素を表わす。これは、殊に鉱油、たとえばベン ジン、ケロシンまたはディーゼル油のような燃料、または燃料油またはモーター 油のような油である。 式Iのベンズアルデヒドは、殊にたとえば税制上の理由から表示が要求される 鉱油をマーキングするために適当である。その際表示の費用を少なくするために 、マーキングのためにできるだけ少量のマーキング剤を適用するように努める。 炭化水素をマーキングするためには式Iのベンズアルデヒドが塊状または溶液 の形で適用される。溶剤としては、有機溶剤が適当である。とくに、トルオール 、キシロール、ドデシルベンゾール、ジイソプロピルナフタリンのような芳香族 炭化水素またはShell る高級芳香族炭化水素の混合物が適用される。生じる溶液の高い粘度を避けるた めに、一般に溶液に対して、5〜80重量%のベンズアルデヒドの濃度が選択さ れる。 溶解度を改善するために、補助溶剤、たとえばメタノール、エタノール、プロ パノール、イソプロパノール、ブタノール、イソブタノール、ペンタノール、ヘ キサノール、ヘプタノール、オクタノール、2−エチルヘキサノールまたはシク ロヘキサノールのようなアルコール、ブチルエチレングリコールまたはメチルプ ロピレングリコールのようなグリコール、トリエチルアミン、ジイソオクチルア ミン、ジシクロヘキシルアミン、アニリン、N−メチルアニリン、N,N−ジメ チルアニリン、トルイジンまたはキシリジンのような アミン、3−(2−メトキシエトキシ)プロピルアミン、o−クレゾール、m− クレゾールまたはp−クレゾールのようなアルカノールアミン、ジエチルケトン またはシクロヘキサノンのようなケトン、ブチロラクトンのようなラクタム、エ チレンカルボネートまたはプロピレンカルボネートのようなカルボネート、t− ブチルフェノールまたはノニルフェノールのようなフェノール、フタル酸メチル エステル、フタル酸−(2−エチルヘキシル)エステル、酢酸エチルエステル、 酢酸ブチルエステルまたは酢酸シクロヘキシルエステルまたは酢酸シクロヘキシ ルエステルのようなエステル、N,N−ジメチルホルムアミド、N,N−ジエチ ルアセトアミドまたはN−メチルピロリジノンのようなアミド、またはその混合 物を使用することもできる。 本発明により適用すべきベンズアルデヒドを用いて、マーキング物質が僅かに 約10ppmまたはそれ以下の濃度で存在する場合でも、マーキングされた炭化 水素を検出するのは非常に簡単に成功する。 炭化水素中にマーキング物質として存在する式Iの化合物の存在の検出は、炭 化水素を、式IIのピリリウム塩および・または式IIIのインドール、プロト ン酸および場合により金属亜鉛、アルミニウムまたはスズのハロゲン化物を合有 する水−アルコール媒体またはアルコール媒体で処理するときに有利に成功する 。水−アルコール媒体を使用する場合、水:アルコールの重量比は0.5:1〜 4:1、とくに約1:1である。水−アルコール相の明らかに目に見える色の変 化が生じる。 適当なアルコールは、たとえばエタノール、プロパノール、イソプロパノール 、1−メトキシプロパン−2−オール、エチレングリコールまたは1,2−また は1,3−プロピレングリコールである。エタノールの使用が好ましい。 本発明による方法に適当なプロトン酸は、殊にいわゆる強酸、つまりpKa値 が≦3.5であるプロトン酸である。このような酸としては、たとえば無機酸ま たは有機酸、たとえば過塩素酸、ヨウ化水素酸、塩化水素酸、臭化水素酸、フッ 化水素酸、硫酸、硝酸、リン酸、ベンゾールスルホン酸、トルオールスルホン酸 、ナフタリンスルホン酸、メタンスルホン酸、シュウ酸、マレイン酸、クロル酢 酸、ジクロル酢酸またはブロム酢酸が挙げられる。多くの場合、これらの酸をた とえば酢酸の添加により緩衝するのが有利である。 o−またはp−トルオールスルホン酸のほかに、殊に無機酸が挙げられその際 塩酸または硫酸がとくに重要である。 金属亜鉛、アルミニウムまたはスズの適当なハロゲン化物は、たとえば塩化亜 鉛、臭化亜鉛、塩化アルミニウム、臭化アルミニウムまたは四塩化スズである。 塩化亜鉛がとくに挙げられる。 通例、色の変化を得るためには、本発明によりマーキングされた炭化水素約1 0〜50mlの量を、式IIのピリリウム塩および/または式IIIのインドー ル、プロトン酸の水−アルコール溶液またはアルコール溶液約1〜50mlで、 場合により金属ハロゲン化物を添加して、振出すれば十分である。プロトン酸の 溶液の代わりに、金属ハロゲン化物単独の水−アルコール溶液を利用することも 可能である。それというのも該溶液は同様に酸性に反応するからである。 その際、水−アルコール溶液またはアルコール溶液中のプロトン酸の濃度は、 通例5〜50重量%、とくに10〜30重量%である。金属ハロゲン化物の濃度 は一般に、その都度溶液の重量に対して、0〜50重量%、とくに5〜20重量 %である。 本発明の1つの大きな利点は、式Iのベンズアルデヒドの検出のために2つの 異なる方法を利用することができることである。従って、検出は妨害の影響(た とえばディーゼル燃料中の添加物)の可能な際にも非常に確実に実施することが できる。 次の例により本発明を詳細に説明する。 一般的指定1: 市販のディーゼル燃料に、ベンズアルデヒドその都度10ppmを加えた。こ のために、予めアルデヒドをトルオールに0.1重量%に溶解し、この溶液をデ ィーゼル燃料に加えた。 次の例に1〜12において、こうしてマーキングしたディーゼル燃料その都度 10mlに試薬溶液2mlを加え、5分振盪した。引き続き、水1mlを添加し 、さらに5分振盪した。水相は次の表1に記載した色を示した。 試薬溶液1 エタノール中インドール1重量% 5ml 濃塩酸 5ml 塩化亜鉛 5g 酢酸 95ml 試薬溶液2 エタノール中2−メチルインドール1重量%5ml 濃塩酸 5ml 塩化亜鉛 5g 酢酸 95ml 試薬溶液3 エタノール中2−フェニルインドール1重量% 5ml 塩化亜鉛 5g 酢酸 95ml ディーゼル燃料を差し当たりシリカゲルに通して濾過すると、とくに有利な結果 が得られる。 マーキング剤として次の表に記載したベンズアルデヒドを使用する場合に、類 似の有利な結果が得られる。 一般的指定2 市販のディーゼル燃料に、その都度ベンズアルデヒド10ppmを加えた。そ のために、トルオールに予めベンズアルデヒドを0.1重量%に溶解し、この溶 液をディーゼル燃料に加えた。 例21〜30においては、その都度マーキングしたディーゼル燃料に試薬溶液 4 2mlを加え、還流下に5分加熱した。引き続き、水/エタノール(1:1 v/v)1mlを添加し、5分振盪した。水相は次の表3に記載した色を示した 。 試薬溶液4 式 水中1重量% 濃塩酸 25ml 酢酸 225ml 試薬溶液4中に含有されているベンゾピリリウム塩を式 の物質に代える場合、類似に有利な結果が得られる。DETAILED DESCRIPTION OF THE INVENTION Use of benzaldehyde to mark hydrocarbons The present invention relates to a compound of formula I as a hydrocarbon marking agent [In the formula Ring A may have a benzo ring added, R1, RTwoAnd RThreeAre independently of each other hydrogen, hydroxy, C1~ CFifteenArchi Le, C1~ CFifteenAlkoxy, cyano, nitro or formula NRFourRFiveOr COOR6To Express, where RFourIs interrupted by 1 to 4 hydrogen or ether functional oxygen atoms Optionally and optionally substituted by phenyl1~ CFifteenTable showing alkyl eagle, I, RFiveMay be interrupted by 1-4 ether-functional oxygen atoms and C optionally substituted by phenyl1~ CFifteenAlkyl, or formula L-NX1 XTwo(L is CTwo~ C8Having the meaning of alkylene, X1And XTwoAre independent of each other C each time1 ~ C6Together with the nitrogen atom having or to which the meaning of alkyl is attached, A 5- or 6-membered saturated heterocyclic group which can still contain an oxygen atom in the ring Has a taste, and R6May be interrupted by 1 to 4 hydrogen, ether functional oxygen atoms C1~ CFifteenRepresents alkyl or has the formula L-NX1XTwo(L, X1And XTwoHaso Each of which has the above-mentioned meaning)] Method for detecting these benzaldehydes in nitrogen, and the above benzaldehyde For hydrocarbons containing United States Patent (US-A) 5145573, United States Patent (US-A) 518237 No. 2, as well as European Patent (EP-A) 499 845, the mineral oil Markin Azo dyes to be used as a coloring agent are already known. US Patent (US-A) 4009008 describes a method for marking mineral oil using disazo dyes Wherein the dye added to the mineral oil is combined with other colored components of the mineral oil. Sorbent is added to the marked mineral oil to make it visible. German patent (DE-A) 3608215 and German patent (DE-A) No. 3,724,575 describes benzopyran derivatives and their use in display systems. Are listed. Example 1 of German Patent (DE-A) 3608215 Has the formula in methanol 2,3-dimethylbenzopyrylium-trichlorozincate And 4-dimethylaminobenzaldehyde. PCT Patent (WO-A11466 / 1994) Marks Mineral Oil Thus, the use of substituted anilines has been described. It is an object of the present invention to provide new marking agents for hydrocarbons. New machine The working agent should be readily available and highly soluble in hydrocarbons. further, The marking agent should be easily detectable. At that time, still extremely Even a small amount of marking agent can be made visible by a strong color reaction. Should be able to. Thereby, the benzaldehyde of the formula I, detailed at the outset, is a hydrocarbon mer It has been found suitable as a King agent. All alkyl and alkylene groups appearing in Formula I above are straight-chain. Or a branched chain. X1And XTwoIs, together with the nitrogen atom to which it is attached, one more oxygen in the ring Can contain atoms When it represents a 5- or 6-membered saturated heterocyclic group, this includes, for example, pyrrolidinyl , Piperazinyl or morpholinyl. Group R1, RTwo, RThree, RFour, RFive, R6, X1And XTwoIs, for example, methyl, ethyl , Propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, Isopentyl, neopentyl, tert-pentyl, hexyl or 2-methyl Pentyl. Further, the group R1, RTwo, RThree, RFour, RFiveAnd R6Is for example heptyl, octyl , 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl , Undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl , Isotridecyl, tetradecyl or pentadecyl (the above name is Cutyl, isononyl, isodecyl and isotridecyl are common names and Derived from alcohols obtained by Sosynthesis-see Ullmnn ' s Encyclopedia of Industrial Chemist ry, 5th edition, volume A1, pages 290 to 293, and volume A10, 284 and See page 285). Further, the group R1, RTwoAnd RThreeIs, for example, methoxy, ethoxy, propoxy , Isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy Si, isopentyloxy, neopentyloxy, te rt-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyl Oxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, Nyloxy, isononyloxy, decyloxy, isodecyloxy, undecyl Oxy, dodecyloxy, tridecyloxy, 3,5,5,7-tetramethylno Nyloxy, isotridecyloxy, tetradecyloxy or pentadecylo Kishi. Further, the group RFourAnd RFiveIs, for example, 2-methoxyethyl, 2-ethoxyethyl , 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2 -Or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4- Toxyl butyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybuty , 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-di Xaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7- Dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8 -Dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxau Undecyl, 3,6,9,12-tetraoxatridecyl, benzyl or 1- Or 2-phenylethyl. The group L is, for example, (CHTwo)Two, (CHTwo)Three, (CHTwo )Four, (CHTwo)Five, (CHTwo)6, (CHTwo)7, (CHTwo)8, (CH (CHThree) C HTwoOr CH (CHThree) CH (CHThree). Preferably according to the invention, the group R1~ RThreeAt least one of the formulas NRFourRFive(Where RFour And RFiveWherein each has the meaning given above), a benzaldehyde of the formula I Is used. Particularly preferably, for marking hydrocarbons, the compounds of the formula Ia [Where R1, RTwo, RFourAnd RFiveHas the above meaning.] used. Particularly suitable is R1And RTwoAre each independently of the other hydrogen, hydroxy, C1 ~ CFifteenAlkyl, C1~ CFifteenAlkoxy or formula COOR6(R6Means the above Having a group represented byFourIs hydrogen or C1~ CFifteenRepresents alkyl and RFiveIs C1~ CFifteenBenzaldehyde of formula Ia representing alkyl. Particularly preferably, for marking hydrocarbons, RFourAnd RFiveAre mutually German C every time1~ C13Alkyl, and R1And RTwoBut water each time Benzaldehyde of the formula Ia is used. Furthermore, the subject of the present invention detects the presence of a benzaldehyde of the formula I in a hydrocarbon. Wherein the hydrocarbon is converted to a protonic acid, of the formula II [Where R7Is C1~ C8Alkyl, phenyl, C1~ CFiveAlkoxy or halogen And R8Represents methyl or R7And R8Are together, 1,4-butyl Wherein ring B may be cycloadded by a benzol ring and optionally C1~ CFourWith alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine Is optionally substituted at the 7-position of the ring;1~ CFourAlkoxy , C1~ CFiveMono- or dialkylamino (in each case again chlorine or phenyl) X may be further substituted-Represents any anion Substituted benzopyrylium salts of formula III [Where R9And RTenAre each independently of the other hydrogen, hydroxy, formula NRFourRFive( RFourAnd RFiveHas in each case the abovementioned meaning), C1~ C8Alkyl, phenyl Le, C1~ CFiveRepresents alkoxy or halogen] At least one compound from the group of compounds consisting of indole and optionally gold Water-alcohol medium containing halides of the genus zinc, aluminum or tin Alternatively, treat with an alcoholic medium. Preferably, according to the invention, indole of formula III, in particular 2-phenylindole Is used. A suitable anion X-Examples of tetrachlorozinc salts, halides, sulfates, Tetrafluoroborate or phosphate. Benzaldehyde I, benzopyrylium salt II and indole III are not The examples themselves are known. Marking in the sense of the present invention means converting a benzaldehyde of the formula I into a hydrocarbon. At certain concentrations, whereby hydrocarbons are completely invisible or almost invisible to the human eye. It is colored so that it cannot be seen, the benzaldehyde of the formula I being described here in detail. To be easily and clearly visible and detectable by the detection method described. You. Another object of the invention is a carbonized compound containing one or several benzaldehydes of the formula I Hydrogen. Hydrocarbons in the sense according to the present invention are present in a liquid, aggregated state under standard conditions. Represents an existing aliphatic or aromatic hydrocarbon. This is especially true for mineral oils such as Ben Fuel such as gin, kerosene or diesel oil, or fuel oil or motor It is oil like oil. The benzaldehydes of the formula I are required to be labeled, in particular for tax reasons, for example. Suitable for marking mineral oil. In order to reduce the cost of labeling Try to apply as little marking agent as possible for marking. For marking hydrocarbons, the benzaldehydes of the formula I may be in bulk or in solution. Applied in the form of As the solvent, an organic solvent is suitable. In particular, , Aromatics such as xylol, dodecylbenzol, diisopropylnaphthalene Hydrocarbon or Shell A mixture of higher aromatic hydrocarbons is applied. To avoid the resulting high viscosity of the solution In general, a concentration of 5 to 80% by weight of benzaldehyde, based on the solution, is selected. It is. To improve solubility, cosolvents such as methanol, ethanol, Pananol, isopropanol, butanol, isobutanol, pentanol, Xanol, heptanol, octanol, 2-ethylhexanol or cycle Alcohols such as rohexanol, butyl ethylene glycol or methyl Glycols such as propylene glycol, triethylamine, diisooctylua Min, dicyclohexylamine, aniline, N-methylaniline, N, N-dimethyl Such as tilaniline, toluidine or xylidine Amine, 3- (2-methoxyethoxy) propylamine, o-cresol, m- Alkanolamines such as cresol or p-cresol, diethyl ketone Or ketones such as cyclohexanone, lactams such as butyrolactone, Carbonates such as tylene carbonate or propylene carbonate, t- Phenol, such as butylphenol or nonylphenol, methyl phthalate Ester, phthalic acid- (2-ethylhexyl) ester, ethyl acetate, Butyl acetate or cyclohexyl acetate or cyclohexyl acetate Esters, such as N, N-dimethylformamide, N, N-diethyl Amides such as lucaceamide or N-methylpyrrolidinone, or a mixture thereof Things can also be used. With the benzaldehyde to be applied according to the invention, the marking substance is slightly reduced Even when present at concentrations of about 10 ppm or less, the marked carbonized Detecting hydrogen is very straightforward. Detection of the presence of a compound of Formula I present as a marking material in hydrocarbons Hydrogen hydride is converted to a pyrylium salt of formula II and / or an indole, proto Acidic acid and optionally metal halides of zinc, aluminum or tin Advantageously successful when treated with water-alcohol or alcoholic media . When using a water-alcohol medium, the weight ratio of water: alcohol is 0.5: 1 to 1: 1. 4: 1, especially about 1: 1. Clearly visible color change of the water-alcohol phase Transformation occurs. Suitable alcohols are, for example, ethanol, propanol, isopropanol , 1-methoxypropan-2-ol, ethylene glycol or 1,2- or Is 1,3-propylene glycol. The use of ethanol is preferred. Protic acids suitable for the process according to the invention are, in particular, the so-called strong acids, ie pKa values. Is a protic acid with ≦ 3.5. Such acids include, for example, inorganic acids. Or organic acids such as perchloric acid, hydroiodic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, Hydrofluoric acid, sulfuric acid, nitric acid, phosphoric acid, benzolsulfonic acid, toluenesulfonic acid , Naphthalenesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid, chloro vinegar Acids, dichloroacetic acid or bromoacetic acid. Often, these acids It is advantageous to buffer, for example, by adding acetic acid. In addition to o- or p-toluenesulfonic acid, mention may in particular be made of inorganic acids. Hydrochloric acid or sulfuric acid is particularly important. Suitable halides of metallic zinc, aluminum or tin are, for example, Lead, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride. Zinc chloride is particularly mentioned. As a rule, in order to obtain a color change, about one hydrocarbon marked according to the invention is used. 0 to 50 ml of the pyrylium salt of the formula II and / or the indole of the formula III About 1 to 50 ml of a water-alcohol or alcoholic solution of a protonic acid, It is sufficient to add a metal halide, if necessary, and shake. Protic acid Instead of a solution, a water-alcohol solution of a metal halide alone may be used. It is possible. This is because the solution likewise reacts acidicly. At that time, the concentration of the protonic acid in the water-alcohol solution or the alcohol solution is: It is usually from 5 to 50% by weight, in particular from 10 to 30% by weight. Metal halide concentration Is generally from 0 to 50% by weight, in particular from 5 to 20% by weight, based in each case on the weight of the solution. %. One great advantage of the present invention is that for the detection of benzaldehyde of formula I, two Different methods can be used. Therefore, the detection was Is very reliable when possible. it can. The following example illustrates the invention in detail. General designation 1: To commercial diesel fuel, 10 ppm of benzaldehyde were added in each case. This For this purpose, the aldehyde was previously dissolved in toluene at 0.1% by weight, and the solution was dehydrated. Added to diesel fuel. Diesel fuel thus marked in the following examples 1 to 12 in each case 2 ml of the reagent solution was added to 10 ml, and the mixture was shaken for 5 minutes. Then add 1 ml of water And shaken for another 5 minutes. The aqueous phase had the colors described in Table 1 below. Reagent solution 1 5% indole 1% by weight in ethanol 5 ml concentrated hydrochloric acid 5 g of zinc chloride Acetic acid 95ml Reagent solution 2 2-methylindole 1% by weight in ethanol 5ml 5 ml concentrated hydrochloric acid 5 g of zinc chloride Acetic acid 95ml Reagent solution 3 1% by weight of 2-phenylindole in ethanol 5ml 5 g of zinc chloride Acetic acid 95ml Particularly advantageous results when diesel fuel is first filtered through silica gel Is obtained. When using benzaldehyde described in the following table as a marking agent, Similar advantageous results are obtained. General designation 2 In each case 10 ppm of benzaldehyde were added to commercial diesel fuel. So For example, benzaldehyde was previously dissolved in toluene at 0.1% by weight, The liquid was added to the diesel fuel. In Examples 21 to 30, reagent solutions were added to the respectively marked diesel fuel. 42 ml was added and the mixture was heated under reflux for 5 minutes. Subsequently, water / ethanol (1: 1) (v / v) 1 ml was added and shaken for 5 minutes. The aqueous phase had the colors described in Table 3 below. . Reagent solution 4 formula 1% by weight in water 25 ml concentrated hydrochloric acid Acetic acid 225ml The benzopyrylium salt contained in the reagent solution 4 is represented by the formula A similar advantageous result is obtained when the substance is replaced by
───────────────────────────────────────────────────── フロントページの続き (72)発明者 カーリン ハイドルン ベック ドイツ連邦共和国 D−67067 ルートヴ ィッヒスハーフェン ダッケンハイマー シュトラーセ 3 (72)発明者 ウード マイアー ドイツ連邦共和国 D−67227 フランケ ンタール マックス−シュレフォークト− シュトラーセ 27────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Carlin Heidlön Beck Germany D-67067 Ludv Ligshafen duckenheimer Strasse 3 (72) Inventor Oud Meier Germany D-67227 Franke Nartal Max-Schleuffolk- Strasse 27
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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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Publication number | Priority date | Publication date | Assignee | Title |
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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
Also Published As
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KR970704860A (en) | 1997-09-06 |
CA2195019A1 (en) | 1996-02-01 |
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 |
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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