CA1047252A - Alkyldiaminoamids of fatty acids as gasoline additives - Google Patents
Alkyldiaminoamids of fatty acids as gasoline additivesInfo
- Publication number
- CA1047252A CA1047252A CA230,969A CA230969A CA1047252A CA 1047252 A CA1047252 A CA 1047252A CA 230969 A CA230969 A CA 230969A CA 1047252 A CA1047252 A CA 1047252A
- Authority
- CA
- Canada
- Prior art keywords
- additive
- carbon atoms
- hydrocarbon radical
- aliphatic hydrocarbon
- propylenediamine
- 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.)
- Expired
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract description 6
- 229930195729 fatty acid Natural products 0.000 title abstract description 6
- 239000000194 fatty acid Substances 0.000 title abstract description 6
- 150000004665 fatty acids Chemical class 0.000 title abstract description 6
- 239000003254 gasoline additive Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000000654 additive Substances 0.000 claims abstract description 19
- 239000000446 fuel Substances 0.000 claims abstract description 16
- 230000000996 additive effect Effects 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 230000009977 dual effect Effects 0.000 claims abstract 4
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 16
- 239000003760 tallow Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 2
- CZQGGQJIGAFLDY-UHFFFAOYSA-N 1-n-(3-tridecoxypropyl)propane-1,2-diamine Chemical compound CCCCCCCCCCCCCOCCCNCC(C)N CZQGGQJIGAFLDY-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000002485 combustion reaction Methods 0.000 abstract description 4
- 238000010348 incorporation Methods 0.000 abstract description 3
- 239000002966 varnish Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 description 17
- 239000000306 component Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 5
- -1 amine phos-phates Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000002816 fuel additive Substances 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ICMQNHVICKPRES-UHFFFAOYSA-N 1-N-nonylpropane-1,2-diamine Chemical compound C(CCCCCCCC)NCC(C)N ICMQNHVICKPRES-UHFFFAOYSA-N 0.000 description 1
- KSUXXXRPJJIXML-UHFFFAOYSA-N 1-N-octadeca-1,3-dienylpropane-1,2-diamine Chemical compound C(=CC=CCCCCCCCCCCCCCC)NCC(C)N KSUXXXRPJJIXML-UHFFFAOYSA-N 0.000 description 1
- SARRTAZBYHWERH-UHFFFAOYSA-N 1-n-docosylpropane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNCC(C)N SARRTAZBYHWERH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RHXXPAYNTFAQBW-UHFFFAOYSA-N C(=CCCCCCCCCCCCCCCCCCC)NCC(C)N Chemical compound C(=CCCCCCCCCCCCCCCCCCC)NCC(C)N RHXXPAYNTFAQBW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical class NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US522709A US3923474A (en) | 1974-11-11 | 1974-11-11 | Alkyldiaminoamids of fatty acids as gasoline additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047252A true CA1047252A (en) | 1979-01-30 |
Family
ID=24082001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,969A Expired CA1047252A (en) | 1974-11-11 | 1975-07-08 | Alkyldiaminoamids of fatty acids as gasoline additives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3923474A (nl) |
| JP (1) | JPS5516196B2 (nl) |
| BE (1) | BE835025A (nl) |
| CA (1) | CA1047252A (nl) |
| DE (1) | DE2549691A1 (nl) |
| FR (1) | FR2290489A1 (nl) |
| GB (1) | GB1483866A (nl) |
| IT (1) | IT1048323B (nl) |
| NL (1) | NL7508814A (nl) |
| NO (1) | NO141519C (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828038A1 (de) * | 1978-06-26 | 1980-01-10 | Basf Ag | Kraftstoffe fuer ottomotoren |
| US4394278A (en) * | 1981-05-26 | 1983-07-19 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
| US4857073A (en) * | 1987-08-27 | 1989-08-15 | Wynn Oil Company | Diesel fuel additive |
| US20050249564A1 (en) * | 2004-05-05 | 2005-11-10 | One World Technologies Limited | Auxiliary handle for a portable power tool |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3035907A (en) * | 1956-06-14 | 1962-05-22 | Gulf Research Development Co | Hydrocarbon composition containing an itaconic acid-amine reaction product |
| US3468639A (en) * | 1965-08-06 | 1969-09-23 | Chevron Res | Gasolines containing deposit-reducing monoamides of polyamines characterized by improved water tolerance |
| US3655351A (en) * | 1969-05-29 | 1972-04-11 | Cities Service Oil Co | Gasoline composition |
| US3681038A (en) * | 1970-03-09 | 1972-08-01 | Universal Oil Prod Co | Middle distillate |
| US3765850A (en) * | 1970-09-30 | 1973-10-16 | Cities Service Oil Co | Hydrocarbon fuel compositions |
-
1974
- 1974-11-11 US US522709A patent/US3923474A/en not_active Expired - Lifetime
-
1975
- 1975-07-08 CA CA230,969A patent/CA1047252A/en not_active Expired
- 1975-07-23 NL NL7508814A patent/NL7508814A/nl not_active Application Discontinuation
- 1975-10-23 IT IT51902/75A patent/IT1048323B/it active
- 1975-10-28 NO NO753608A patent/NO141519C/no unknown
- 1975-10-30 BE BE1006983A patent/BE835025A/xx not_active IP Right Cessation
- 1975-10-30 FR FR7533207A patent/FR2290489A1/fr active Granted
- 1975-11-03 DE DE19752549691 patent/DE2549691A1/de not_active Withdrawn
- 1975-11-10 JP JP13500975A patent/JPS5516196B2/ja not_active Expired
- 1975-11-11 GB GB46556/75A patent/GB1483866A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5170204A (nl) | 1976-06-17 |
| NO141519B (no) | 1979-12-17 |
| NL7508814A (nl) | 1976-05-13 |
| DE2549691A1 (de) | 1976-05-13 |
| IT1048323B (it) | 1980-11-20 |
| FR2290489B1 (nl) | 1979-08-03 |
| NO141519C (no) | 1980-03-26 |
| JPS5516196B2 (nl) | 1980-04-30 |
| US3923474A (en) | 1975-12-02 |
| NO753608L (nl) | 1976-05-12 |
| GB1483866A (en) | 1977-08-24 |
| BE835025A (fr) | 1976-04-30 |
| FR2290489A1 (fr) | 1976-06-04 |
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