CA1096879A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1096879A
Authority: CA; Canada
Prior art keywords: compounds; poly; oxyalkylene; fuel; deposit
Prior art date: 1976-06-21
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

CA280,934A

Other languages

English (en)

Inventor

Robert A. Lewis

Lewis R. Honnen

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.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology 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.)

1976-06-21

Filing date

1977-06-20

Publication date

1981-03-03

1976-10-07 Priority claimed from US05/730,405 external-priority patent/US4044927A/en

1977-06-20 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1981-03-03 Application granted granted Critical

1981-03-03 Publication of CA1096879A publication Critical patent/CA1096879A/fr

Status Expired legal-status Critical Current

Links

239000000654 additive Substances 0.000 title claims abstract description 28
150000004657 carbamic acid derivatives Chemical class 0.000 claims abstract description 11
238000002485 combustion reaction Methods 0.000 claims abstract description 10
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 13
-1 poly(oxyalkylene) Polymers 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
125000005702 oxyalkylene group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims 5
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 abstract description 2
230000003749 cleanliness Effects 0.000 abstract description 2
229940012017 ethylenediamine Drugs 0.000 abstract 1
239000000446 fuel Substances 0.000 description 32
239000000463 material Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
238000012360 testing method Methods 0.000 description 14
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 13
229920000570 polyether Polymers 0.000 description 13
239000004721 Polyphenylene oxide Substances 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000000996 additive effect Effects 0.000 description 12
150000001412 amines Chemical class 0.000 description 9
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000003599 detergent Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
239000002199 base oil Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
238000011160 research Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000010998 test method Methods 0.000 description 3
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003403 chloroformylation reaction Methods 0.000 description 2
238000013461 design Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000002816 fuel additive Substances 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
ISBSSBGEYIBVTO-TYKWNDPBSA-N (20R,22R)-20,22-dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC2 ISBSSBGEYIBVTO-TYKWNDPBSA-N 0.000 description 1
LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
KAVDAMFOTJIBCK-XSHPSBQMSA-N 5-[(e)-2-bromoethenyl]-1-[(1s,3r,4s)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]pyrimidine-2,4-dione Chemical compound C1[C@@H](O)[C@H](CO)C[C@@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 KAVDAMFOTJIBCK-XSHPSBQMSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000725101 Clea Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000982822 Ficus obtusifolia Species 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000005529 alkyleneoxy group Chemical group 0.000 description 1
239000006079 antiknock agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
210000000941 bile Anatomy 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
239000006080 lead scavenger Substances 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001117 oleyl 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])=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
239000003960 organic solvent Substances 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010926 purge Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Solid Fuels And Fuel-Associated Substances (AREA)

CA280,934A 1976-06-21 1977-06-20 Traduction non-disponible Expired CA1096879A (fr)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US69824376A	1976-06-21	1976-06-21
US698,243		1976-06-21
US70092276A	1976-06-29	1976-06-29
US700,922		1976-06-29
US05/730,405 US4044927A (en)	1976-10-07	1976-10-07	Ladle with axis of rotation through discharge spout
US80144477A	1977-05-27	1977-05-27
US801,444		1977-05-27
US730,405		1985-05-02

Publications (1)

Publication Number	Publication Date
CA1096879A true CA1096879A (fr)	1981-03-03

Family

ID=27505469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA280,934A Expired CA1096879A (fr)	1976-06-21	1977-06-20	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1096879A (fr)

1977
- 1977-06-20 CA CA280,934A patent/CA1096879A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-03-03	MKEX	Expiry

Publication	Publication Date	Title
US4236020A (en)	1980-11-25	Carbamate deposit control additives
US4160648A (en)	1979-07-10	Fuel compositions containing deposit control additives
US4191537A (en)	1980-03-04	Fuel compositions of poly(oxyalkylene) aminocarbamate
US3898056A (en)	1975-08-05	Hydrocarbylamine additives for distillate fuels
US4247301A (en)	1981-01-27	Deposit control and dispersant additives
CA1123851A (fr)	1982-05-18	Additifs anticambouis, et carburants qui les renferment
US4604103A (en)	1986-08-05	Deposit control additives--polyether polyamine ethanes
EP1080166B1 (fr)	2011-01-05	Compositions de carburant contenant des amines polyoxyalkylene substituees par hydrocarbyle
US4270930A (en)	1981-06-02	Clean combustion chamber fuel composition
CA1254388A (fr)	1989-05-23	Produit de reaction de l'anhydride maleique, d'un polyether et d'une polyamine; son utilistion comme additif dans les carburants
EP0240743B1 (fr)	1990-05-23	Combustible
US4527996A (en)	1985-07-09	Deposit control additives - hydroxy polyether polyamines
US20220145199A1 (en)	2022-05-12	Fuel additives for mitigating injector nozzle fouling and reducing particulate emissions
US4526587A (en)	1985-07-02	Deposit control additives-methylol polyether amino ethanes
US4024083A (en)	1977-05-17	Substituted phenoxy propanol diamines and amino alcohol detergent additives for fuels and mineral oils
EP0152455B1 (fr)	1989-06-14	Carburant diesel et procede pour reguler le depot dans le moteur a allumage par compression
US4695291A (en)	1987-09-22	Poly(oxyalkylene) aminoether carbamates as deposit control additives
EP0590770B1 (fr)	1999-02-24	Une méthode de préparation d'une composition d'amidoalcanolamine pour combustibles
EP0162890B1 (fr)	1989-08-23	Additifs de regulation de depot - polyamines de polyether hydroxy
CA1087843A (fr)	1980-10-21	Combustibles contenant des formamides dialkyles
CA2095715A1 (fr)	1993-12-11	Additif pour carburants, methode de preparation et composition de carburant
CA1138201A (fr)	1982-12-28	Essence a teneur de detergent
CA2049954C (fr)	2003-04-01	Composition d'additif pour combustible
GB1581868A (en)	1980-12-31	Deposit control additives
US4521610A (en)	1985-06-04	Poly(oxyalkylene) aminoether carbamates as deposit control additives