CA1076802A - Additif et melange polyvalents de carburant - Google Patents

Additif et melange polyvalents de carburant

Info

Publication number: CA1076802A
Authority: CA; Canada
Prior art keywords: phenol; amine; additive; hydrogen; composition
Prior art date: 1974-12-24
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.): Expired

Application number

CA242,178A

Other languages

English (en)

Other versions

CA242178S (en

Inventor

Warren H. Machleder

Joseph M. Bollinger

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas 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.)

1974-12-24

Filing date

1975-12-19

Publication date

1980-05-06

1975-12-19 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1977-07-05 Priority claimed from US05/813,028 external-priority patent/US4134846A/en

1980-05-06 Application granted granted Critical

1980-05-06 Publication of CA1076802A publication Critical patent/CA1076802A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 135
239000002816 fuel additive Substances 0.000 title claims abstract description 10
150000001412 amines Chemical class 0.000 claims abstract description 84
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 78
229920002367 Polyisobutene Polymers 0.000 claims abstract description 59
239000003502 gasoline Substances 0.000 claims abstract description 50
239000000446 fuel Substances 0.000 claims abstract description 47
239000003599 detergent Substances 0.000 claims abstract description 21
239000007795 chemical reaction product Substances 0.000 claims abstract description 20
239000000654 additive Substances 0.000 claims description 64
-1 glycidyl ether compound Chemical class 0.000 claims description 54
230000000996 additive effect Effects 0.000 claims description 49
229930195733 hydrocarbon Natural products 0.000 claims description 32
239000004215 Carbon black (E152) Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
150000002430 hydrocarbons Chemical class 0.000 claims description 26
229920001281 polyalkylene Polymers 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
239000010687 lubricating oil Substances 0.000 claims description 18
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
239000005977 Ethylene Substances 0.000 claims description 8
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 7
IRTOOLQOINXNHY-UHFFFAOYSA-N 1-(2-aminoethylamino)ethanol Chemical compound CC(O)NCCN IRTOOLQOINXNHY-UHFFFAOYSA-N 0.000 claims description 6
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 6
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000003916 ethylene diamine group Chemical group 0.000 claims description 5
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 5
150000004996 alkyl benzenes Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
150000002431 hydrogen Chemical group 0.000 claims 6
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 claims 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 2
NAHHNSMHYCLMON-UHFFFAOYSA-N 2-pyridin-3-ylethanamine Chemical compound NCCC1=CC=CN=C1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 abstract description 61
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 21
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract description 20
238000002485 combustion reaction Methods 0.000 abstract description 20
230000006698 induction Effects 0.000 abstract description 19
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 18
230000005764 inhibitory process Effects 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 7
238000005576 amination reaction Methods 0.000 abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 34
238000012360 testing method Methods 0.000 description 32
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 27
239000000306 component Substances 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
238000006467 substitution reaction Methods 0.000 description 17
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 15
238000007792 addition Methods 0.000 description 14
239000003112 inhibitor Substances 0.000 description 14
239000011572 manganese Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
229960005419 nitrogen Drugs 0.000 description 12
229920000768 polyamine Polymers 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
239000000376 reactant Substances 0.000 description 10
239000008096 xylene Substances 0.000 description 10
150000004985 diamines Chemical class 0.000 description 9
238000000034 method Methods 0.000 description 8
150000002989 phenols Chemical class 0.000 description 8
238000010998 test method Methods 0.000 description 8
201000006747 infectious mononucleosis Diseases 0.000 description 7
239000012071 phase Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
239000000295 fuel oil Substances 0.000 description 6
239000003254 gasoline additive Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
239000003377 acid catalyst Substances 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012266 salt solution Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
239000011324 bead Substances 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000003749 cleanliness Effects 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000005484 gravity Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000010705 motor oil Substances 0.000 description 2
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229920001083 polybutene Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
ZBZYEEDUIBFZGY-UHFFFAOYSA-N 1-[3-aminopropyl(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CCCN)CC(O)CC ZBZYEEDUIBFZGY-UHFFFAOYSA-N 0.000 description 1
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XFBCIULBTBLLOK-UHFFFAOYSA-N 1-n,1-n-dimethylbutane-1,3-diamine Chemical compound CC(N)CCN(C)C XFBCIULBTBLLOK-UHFFFAOYSA-N 0.000 description 1
ZLNYAYUHRGEPKE-UHFFFAOYSA-N 1-n,1-n-dimethylhexane-1,3-diamine Chemical compound CCCC(N)CCN(C)C ZLNYAYUHRGEPKE-UHFFFAOYSA-N 0.000 description 1
RRQHLOZQFPWDCA-UHFFFAOYSA-N 1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CC(N)CN(C)C RRQHLOZQFPWDCA-UHFFFAOYSA-N 0.000 description 1
FPZUBOBWFBWTOA-UHFFFAOYSA-N 1-n-(2-aminobutyl)-1-n-(2-aminohexyl)hexane-1,2-diamine Chemical compound CCCCC(N)CN(CC(N)CC)CC(N)CCCC FPZUBOBWFBWTOA-UHFFFAOYSA-N 0.000 description 1
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HVZDOGDLNGQLST-UHFFFAOYSA-N 2,4-diaminobutan-2-ol Chemical compound CC(N)(O)CCN HVZDOGDLNGQLST-UHFFFAOYSA-N 0.000 description 1
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125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
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ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical class CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
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WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
YNDUPGQMECPWKD-UHFFFAOYSA-N [O-][N+](=O)S[N+]([O-])=O Chemical compound [O-][N+](=O)S[N+]([O-])=O YNDUPGQMECPWKD-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
239000006079 antiknock agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
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238000003556 assay Methods 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
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239000002283 diesel fuel Substances 0.000 description 1
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AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000013538 functional additive Substances 0.000 description 1
238000004868 gas analysis Methods 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000003879 lubricant additive Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
VHCPBLNDTKVHTI-UHFFFAOYSA-N n',n'-bis(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCN(CCN)CCN VHCPBLNDTKVHTI-UHFFFAOYSA-N 0.000 description 1
KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
WLCAJRWUALFWOA-UHFFFAOYSA-N n',n'-dihexylpropane-1,3-diamine Chemical compound CCCCCCN(CCCN)CCCCCC WLCAJRWUALFWOA-UHFFFAOYSA-N 0.000 description 1
AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 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
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Liquid Carbonaceous Fuels (AREA)
Lubricants (AREA)

CA242,178A 1974-12-24 1975-12-19 Additif et melange polyvalents de carburant Expired CA1076802A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US53607274A	1974-12-24	1974-12-24
US05/813,028 US4134846A (en)	1976-03-29	1977-07-05	Multipurpose hydrocarbon fuel and lubricating oil additive mixture

Publications (1)

Publication Number	Publication Date
CA1076802A true CA1076802A (fr)	1980-05-06

Family

ID=27065027

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA242,178A Expired CA1076802A (fr)	1974-12-24	1975-12-19	Additif et melange polyvalents de carburant

Country Status (1)

Country	Link
CA (1)	CA1076802A (fr)

1975
- 1975-12-19 CA CA242,178A patent/CA1076802A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-05-06	MKEX	Expiry

Publication	Publication Date	Title
US4134846A (en)	1979-01-16	Multipurpose hydrocarbon fuel and lubricating oil additive mixture
US3443918A (en)	1969-05-13	Gasoline composition
US4247301A (en)	1981-01-27	Deposit control and dispersant additives
US3898056A (en)	1975-08-05	Hydrocarbylamine additives for distillate fuels
US3960515A (en)	1976-06-01	Hydrocarbyl amine additives for distillate fuels
US4881945A (en)	1989-11-21	Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates
CA1264054A (fr)	1989-12-27	Succinimides modifies par le glycidol
US4659336A (en)	1987-04-21	Motor fuel composition
EP0613938A1 (fr)	1994-09-07	Compositions de combustible hydrocarbore incorporant des dispersants contenant de l'azote
WO2001072930A2 (fr)	2001-10-04	Composition d'additif de carburant destinee a ameliorer la distribution de charge modifiant le coefficient de frottement
US4259086A (en)	1981-03-31	Multipurpose hydrocarbon fuel and lubricating oil additive
US4581040A (en)	1986-04-08	Polyoxyisopropylenediamine-acid anhydride-polyamine reaction product and motor fuel composition containing same
US4975096A (en)	1990-12-04	Long chain aliphatic hydrocarbyl amine additives having an oxyalkylene hydroxy connecting group
US4048081A (en)	1977-09-13	Multipurpose fuel additive
EP0590770B1 (fr)	1999-02-24	Une méthode de préparation d'une composition d'amidoalcanolamine pour combustibles
US4322220A (en)	1982-03-30	Multipurpose hydrocarbon fuel and lubricating oil additive
EP0574203A1 (fr)	1993-12-15	Additifs pour carburant
CA2082436C (fr)	1999-05-18	Carbamates, preparation de ceux-ci, et carburants et lubrifiants contenant des carbamates
EP0151621A1 (fr)	1985-08-21	Additifs quaternaires regulateurs de depots.
AU624576B2 (en)	1992-06-18	Fuel compositions and lubricating oil compositions containing substantially straight chain alkylphenyl poly(oxypropylene) aminocarbamates
US4147641A (en)	1979-04-03	Multipurpose hydrocarbon fuel and lubricating oil additive mixture
EP0827999A1 (fr)	1998-03-11	Détergents pour combustibles hydrocarbures
EP0162890B1 (fr)	1989-08-23	Additifs de regulation de depot - polyamines de polyether hydroxy
CA1076802A (fr)	1980-05-06	Additif et melange polyvalents de carburant
EP0149486A2 (fr)	1985-07-24	Détergents et composition de carburant les contenant