CA2068173A1 - Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques - Google Patents

Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques

Info

Publication number: CA2068173A1
Authority: CA; Canada
Prior art keywords: group; marker; alkylated; carbon atoms; ethyl
Prior art date: 1991-05-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002068173A

Other languages

English (en)

Inventor

Kerry C. Brinkman

M. Dayle Enderson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ChampionX LLC

Original Assignee

Nalco Chemical Co

Priority date (The priority date 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 date listed.)

1991-05-03

Filing date

1992-05-07

Publication date

1993-11-08

1992-05-07 Application filed by Nalco Chemical Co filed Critical Nalco Chemical Co

1992-05-07 Priority to CA002068173A priority Critical patent/CA2068173A1/fr

1993-11-08 Publication of CA2068173A1 publication Critical patent/CA2068173A1/fr

Status Abandoned legal-status Critical Current

Links

239000007788 liquid Substances 0.000 title claims abstract description 77
229930195733 hydrocarbon Natural products 0.000 title claims abstract description 59
150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 55
239000000126 substance Substances 0.000 title description 13
239000003550 marker Substances 0.000 claims abstract description 68
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 52
239000000203 mixture Substances 0.000 claims abstract description 48
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
150000001875 compounds Chemical class 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 38
238000004458 analytical method Methods 0.000 claims abstract description 15
229910052717 sulfur Chemical group 0.000 claims abstract description 7
-1 n-octyl Chemical group 0.000 claims description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 19
230000005526 G1 to G0 transition Effects 0.000 claims description 16
150000002334 glycols Chemical class 0.000 claims description 16
229920000151 polyglycol Polymers 0.000 claims description 16
239000010695 polyglycol Substances 0.000 claims description 16
239000003921 oil Substances 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 10
230000005264 electron capture Effects 0.000 claims description 9
239000000446 fuel Substances 0.000 claims description 9
229920001296 polysiloxane Polymers 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
150000002009 diols Chemical class 0.000 claims description 8
239000003502 gasoline Substances 0.000 claims description 8
230000014759 maintenance of location Effects 0.000 claims description 8
229920005862 polyol Polymers 0.000 claims description 8
150000003077 polyols Chemical class 0.000 claims description 8
239000012159 carrier gas Substances 0.000 claims description 7
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
229920000768 polyamine Polymers 0.000 claims description 7
238000000926 separation method Methods 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000002826 coolant Substances 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
229920000642 polymer Polymers 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
229920001577 copolymer Polymers 0.000 claims description 3
239000010779 crude oil Substances 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000010724 circulating oil Substances 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
239000002283 diesel fuel Substances 0.000 claims description 2
239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000010720 hydraulic oil Substances 0.000 claims description 2
239000010687 lubricating oil Substances 0.000 claims description 2
229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
229910052760 oxygen Inorganic materials 0.000 claims 5
239000001301 oxygen Substances 0.000 claims 5
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 3
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 claims 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
125000003136 n-heptyl 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])* 0.000 claims 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
235000013870 dimethyl polysiloxane Nutrition 0.000 claims 1
229920001223 polyethylene glycol Polymers 0.000 claims 1
239000000654 additive Substances 0.000 abstract description 8
125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
125000004434 sulfur atom Chemical group 0.000 abstract description 2
208000018909 Neonatal adrenoleukodystrophy Diseases 0.000 abstract 1
238000002360 preparation method Methods 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000004817 gas chromatography Methods 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000003573 thiols Chemical class 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000001211 electron capture detection Methods 0.000 description 5
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
238000001514 detection method Methods 0.000 description 4
230000002708 enhancing effect Effects 0.000 description 4
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
GQFMWBPVMLWCNA-UHFFFAOYSA-N n,n-dibutyl-3,5-dinitrobenzamide Chemical compound CCCCN(CCCC)C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 GQFMWBPVMLWCNA-UHFFFAOYSA-N 0.000 description 4
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
101150039033 Eci2 gene Proteins 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000007613 environmental effect Effects 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
IBQREHJPMPCXQA-UHFFFAOYSA-N ethyl 3,5-dinitrobenzoate Chemical class CCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 IBQREHJPMPCXQA-UHFFFAOYSA-N 0.000 description 3
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
UJDGGCAEVIIQFE-UHFFFAOYSA-N 1-butyl-6-methyl-3,5-dinitrocyclohexa-2,4-diene-1-carboxylic acid Chemical compound CCCCC1(C(O)=O)C=C([N+]([O-])=O)C=C([N+]([O-])=O)C1C UJDGGCAEVIIQFE-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 2
CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 2
BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 description 2
PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000003673 groundwater Substances 0.000 description 2
QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
KZVBOYCZXPUDGJ-UHFFFAOYSA-N hexyl 3,5-dinitrobenzoate Chemical class CCCCCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 KZVBOYCZXPUDGJ-UHFFFAOYSA-N 0.000 description 2
239000010705 motor oil Substances 0.000 description 2
PABDTGWENZPKAZ-UHFFFAOYSA-N n-(2-ethylhexyl)-3,5-dinitrobenzamide Chemical compound CCCCC(CC)CNC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 PABDTGWENZPKAZ-UHFFFAOYSA-N 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
KVRKVNNGYVWNGH-UHFFFAOYSA-N pentyl 3,5-dinitrobenzoate Chemical class CCCCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 KVRKVNNGYVWNGH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
VATQKFJMBFFMBW-UHFFFAOYSA-N (2-anilinophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1NC1=CC=CC=C1 VATQKFJMBFFMBW-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
BAYAKMPRFGNNFW-UHFFFAOYSA-N 2,4-dimethylpentan-3-ol Chemical compound CC(C)C(O)C(C)C BAYAKMPRFGNNFW-UHFFFAOYSA-N 0.000 description 1
ZIAGHYXKBYYTSW-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethyl 3,5-dinitrobenzoate Chemical compound CCCCCCOCCOCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 ZIAGHYXKBYYTSW-UHFFFAOYSA-N 0.000 description 1
MPRFLYOPKSBFJK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 3,5-dinitrobenzoate Chemical compound COCCOCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPRFLYOPKSBFJK-UHFFFAOYSA-N 0.000 description 1
YLOOKDSVDNUIAF-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethyl 3,5-dinitrobenzoate Chemical compound C(CC)OCCOCCOC(C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])=O YLOOKDSVDNUIAF-UHFFFAOYSA-N 0.000 description 1
QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
GPEWXIVENNPUPI-UHFFFAOYSA-N 2-butoxyethyl 3,5-dinitrobenzoate Chemical compound CCCCOCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 GPEWXIVENNPUPI-UHFFFAOYSA-N 0.000 description 1
LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
LAHZCLZYPLIJOK-UHFFFAOYSA-N 2-methoxyethyl 3,5-dinitrobenzoate Chemical compound COCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 LAHZCLZYPLIJOK-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
QVQDALFNSIKMBH-UHFFFAOYSA-N 2-pentoxyethanol Chemical compound CCCCCOCCO QVQDALFNSIKMBH-UHFFFAOYSA-N 0.000 description 1
XFLJBLMTWBZIPA-UHFFFAOYSA-N 2-propoxyethyl 3,5-dinitrobenzoate Chemical compound C(CC)OCCOC(C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])=O XFLJBLMTWBZIPA-UHFFFAOYSA-N 0.000 description 1
IOHYQARQACZNRM-UHFFFAOYSA-N 3,5-dinitro-2-octylbenzoic acid Chemical compound CCCCCCCCC1=C(C(O)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IOHYQARQACZNRM-UHFFFAOYSA-N 0.000 description 1
DPNAKLBFHSINGT-UHFFFAOYSA-N 3,5-dinitro-n,n-dipentylbenzamide Chemical compound CCCCCN(CCCCC)C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 DPNAKLBFHSINGT-UHFFFAOYSA-N 0.000 description 1
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XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
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SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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239000003112 inhibitor Substances 0.000 description 1
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238000004949 mass spectrometry Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
POGCCFLNFPIIGW-UHFFFAOYSA-N methyl 3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 POGCCFLNFPIIGW-UHFFFAOYSA-N 0.000 description 1
GCPHONFLNJHULD-UHFFFAOYSA-N n,n-bis(2-ethylhexyl)-3,5-dinitrobenzamide Chemical compound CCCCC(CC)CN(CC(CC)CCCC)C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 GCPHONFLNJHULD-UHFFFAOYSA-N 0.000 description 1
OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000010742 number 1 fuel oil Substances 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
UUJMMZMVYHKYGJ-UHFFFAOYSA-N octyl 3,5-dinitrobenzoate Chemical class CCCCCCCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UUJMMZMVYHKYGJ-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229940100684 pentylamine Drugs 0.000 description 1
239000006187 pill Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000013849 propane Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000275 quality assurance Methods 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

CA002068173A 1991-05-03 1992-05-07 Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques Abandoned CA2068173A1 (fr)

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CA002068173A CA2068173A1 (fr)	1991-05-03	1992-05-07	Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques

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US69557691A	1991-05-03	1991-05-03
CA002068173A CA2068173A1 (fr)	1991-05-03	1992-05-07	Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques

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WO2019164763A1 (fr) *	2018-02-22	2019-08-29	Exxonmobil Research And Engineering Company	Huiles de base d'huile lubrifiante à base de monoester de benzoate à faible viscosité et faible volatilité et leurs procédés d'utilisation
CN111279189A (zh) *	2017-08-23	2020-06-12	联合色彩制造股份有限公司	含有氮化合物的标记物组合物及其制造和使用方法

1992
- 1992-05-07 CA CA002068173A patent/CA2068173A1/fr not_active Abandoned

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111279189A (zh) *	2017-08-23	2020-06-12	联合色彩制造股份有限公司	含有氮化合物的标记物组合物及其制造和使用方法
WO2019164763A1 (fr) *	2018-02-22	2019-08-29	Exxonmobil Research And Engineering Company	Huiles de base d'huile lubrifiante à base de monoester de benzoate à faible viscosité et faible volatilité et leurs procédés d'utilisation

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Date	Code	Title	Description
1999-05-07	FZDE	Discontinued

CA2068173A1 - Procede pour l'identification des hydrocarbures liquides a l'aide de marqueurs chimiques - Google Patents

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ID=25675124

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