US3250600A - Fuels containing n-tertiary-alkyl alkanesulfonamides - Google Patents
Fuels containing n-tertiary-alkyl alkanesulfonamides Download PDFInfo
- Publication number
- US3250600A US3250600A US175267A US17526762A US3250600A US 3250600 A US3250600 A US 3250600A US 175267 A US175267 A US 175267A US 17526762 A US17526762 A US 17526762A US 3250600 A US3250600 A US 3250600A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- tertiary
- alkanesulfonamides
- carbon atoms
- fuel
- 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 - Lifetime
Links
- 239000000446 fuel Substances 0.000 title claims description 26
- 239000003502 gasoline Substances 0.000 claims description 12
- 239000000295 fuel oil Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 description 25
- 150000003456 sulfonamides Chemical class 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000003209 petroleum derivative Substances 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019271 petrolatum Nutrition 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 4
- -1 hydrocarbon sulfonyl chloride Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000004264 Petrolatum Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-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
- 239000000428 dust Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 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
- 125000001802 myricyl 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])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
- 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
- 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
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000779 smoke Substances 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
- 239000010959 steel Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
Definitions
- This invention is directed to an improved petroleum distillate fuel containing an N-tertiary-alkyl alkanesulfonamide.
- the fuel shows significant anti-icing and anticorrosion properties as well as excellent carburetor detergency.
- carburetor icing The operation of an internal combustion engine under cool, humid atmospheric conditions is usually accompanied by engine stalling.
- This effect referred to as carburetor icing, is attributed to the formation of ice particles in the carburetor, especially on the throttle plate and surrounding throttle body walls. Ice formation at the edge of the throttle plate reduces air flow to the engine, thereby causing stalling, or the air bleeds or venturi may ice and stall the engine from excessively rich mixtures.
- the sulfonamides utilized according to the present invention are derived from tertiary-alkyl amines, and possess significant properties to produce an improved fuel composition.
- the N-tertiary-alkyl hydrocarbon sulfonamides are more stable to oxidation and thereby do not form oxidized products which in turn cause gummy deposits in gasoline.
- the N-tertiary-alkyl alkanesulfonamides are clear liquids.
- the N-normal alkyl alkanesulfonamides are heterogeneous pastes that tend to separate into difierent phases on standing. This undesirable property causes great inconvenience at the refinery where the sulfonamides are blended with the gasoline.
- N-tertiary-alkyl alkanesulfonamides can be pumped directly, while the N-normal- 3,250,000 Patented May 10, 1966 alkyl alkanesulfonamides must be heated to form a homogeneous mixture before pumping and blending.
- the present invention is directed to an improved distillate fuel containing a minor pro ortion of an N-tertiary-alkyl alkanesulfonamide having the structure RSO NHR wherein R is a saturated alkyl radical having 12 to 30 carbon atoms and may contain chlorine, or a mixture of such alkyl radicals, and R is a tertiaryalkyl group having 8 to 22 carbon atoms, or a mixture of such alkyl groups.
- RSO NHR wherein R is a saturated alkyl radical having 12 to 30 carbon atoms and may contain chlorine, or a mixture of such alkyl radicals, and R is a tertiaryalkyl group having 8 to 22 carbon atoms, or a mixture of such alkyl groups.
- R may be octyl, dodecyl, myristyl, cetyl, stearyl, eicosyl, myricyl or mixtures of alkyl groups having 12 to 14, 14 to 16, or 16 to 20 carbon atoms, hydrocarbon groups derived from White Oil, paraffin wax or petrolatum or mixtures of such hydrocarbon groups.
- R is derived from a tertiary-alkyl monoamine and has the structure where the tertiary carbon atom is bonded to the nitrogen atom, and may be tertiary-octyl, tertiary-nonyl or a mixture of tertiary alkyl groups having 1214 carbon atoms or 18-21 carbon atoms.
- N-tertiary-octyl stearylsulfonamide N-tertiary-eicosyl dodecylsulfonamide, N-tertiary-dodecyl White Oil-sulfonamide, and N-tertiary-C alkyl eicosyl-sulfonamide.
- a preferred embodiment of the present invention is a distillate fuel containing a sulfonamide of the heretoforedefined structure RSO NHR wherein the sum of carbon atoms of R and R is 25 to 35.
- Representative preferred compounds are N-tertiary-octyl White Oil-sulfonamide, N-tertiary-nonyl White Oil-sulfonamide, N-tertiary-C alkyl White Oil-sulfonamide, and N-tertiary-dodecyl paraflin waX-sulfonamide.
- additives are significantly eifective in reducing the stalling tendencies and prevention of corrosion in hydrocarbon distillate fuels boiling in the gasoline and fuel oil range, such as kerosene, gas oils, cracked gas oils, compression-ignition and internal combustion fuels, and the conventional burner and furnace oils.
- the amount of sulfonamides to be added to the fuel ranges from 0.0005 to 0.03 weight percent, depending upon the size of the hydrocarbon molecule in the fuel and the particular benefit desired. In motor gasolines, usually about 0.001 to 0.01 percent is used. In heavier fractions such as kerosenes, diesel fuels or household burner fuels, somewhat higher concentrations may be required. Below 0.0005 percent, the effect of the sulfo-namide on the mineral oil decreases. Above 0.03 percent, the effect levels off and does not increase. The use of higher concentrations is thus not economically advantageous.
- the sulfonamides utilized according to the present invention may be prepared by any known methods for the preparation of sulfonamides. They are conveniently prepared by starting with the aliphatic hydrocarbon desired and reacting with gaseous sulfur dioxide'and chlorine in the presence of actinic light to obtain the hydrocarbon sulfonyl chloride, as described in US. Patents 2,046,090 and 2,202,791. The hydrocarbon sulfonyl chloride thus obtained may be further reacted with the desired amine by conventional techniques, as set forth in US. 2,334,186.
- the hydrocarbon sulfonyl chloride used for the preparation of the sulfonamides of the present invention is derived from the sul-fochlorination of a commercially available petroleum hydrocarbon, such as No. 40 White Oil, which is highly acid-washed parafiinic petrodistilled, C. 284
- the anti-icing properties of the sulfonamides of the present invention were demonstrated in a 6-cylinder Chrysler engine iwhose carburetor operated in an atmosphere of 40 F. and 95% relative humidity. Fuel additive combinations were rated by the number of minutes of open throttle operation at 1800 rpm. under a load necessary to cause stalling while idling. With the .use of commercial, winter-grade gasoline without anti-icing protection, stalling occurs within 0.5 to 1.25 minutes, whereas a rating of 4 minutes and more may be obtained with the use of the sulfonamide additive of the invention.
- the base fuel used in this test had the following inspection data: ASTM D86 distillation 10%118 F., 20% 135 F., 50%252 F., and 90%339 F.; Reid vapor pressure 13.2 p.s.i.
- the carburetor detergency properties of the sulfonamides of the present invention may be demonstrated using a Lausen test engine equipped with a Tillotsen carburetor modified by inserting removable leaflets around the throttle plate. Throughout the test, a portion of the exhaust gases of a second single cylinder engine running at a constant 2500 r.p.m. is introduced into the test carburetor. The test engine was cycled one minute at open throttle under dynamometer load and then for two minutes at idle of 1100:100 r.p.m. for a period of two hours. At the conclusion of the test, the leaflets were removed and rated on the scale: 0 representing bright and shiny to 10 representing very heavy black deposits. The gasoline used was commercially available and had the following inspection data:
- alkanesulfonamides of the present invention are markedly more effective as anti-rust agents than the arylsulfonamides described in US. Patent 2,197,851.
- a widely accepted test for anti-rust properties in distillate fuels is the dynamic rust test as described in the U.S. Military qualifying test, MIL-I-25017, wherein a carefully polished steel specimen is subjected to the corrosive action of an agitated mixture of 300 ml. of depolarized isooctane and 30 ml. of synthetic sea water at F. for a period of 20 hours.
- the sulfonamide additives of the present invention are unexpectedly superior in anti-rust and corrosion prevention as well as in their remarkable detergent properties and anti-icing characteristics.
- Another desirable feature of the sulfonamides is their economical attractiveness, being prepared from commercially, readily available materials, low in cost.
- the sulfonamides of the invention may promote the action of, or have their functions improved by, other surface-active materials such as carboxylic acids, amides, amines, heterocyclic compounds, salts of petroleum sulfonates, alkyl phosphate Salts, ylene-oxide condensates and other such surfaceactive substances.
- other surface-active materials such as carboxylic acids, amides, amines, heterocyclic compounds, salts of petroleum sulfonates, alkyl phosphate Salts, ylene-oxide condensates and other such surfaceactive substances.
- An improved distillate fuel selected from the group consisting of gasoline and fuel oils containing from 0.0005 to 0.03 weight percent of an N-tert.-alkyl alkanesulfonamide having the structure RSO NHR wherein R 15 is selected from the group consist-ing of an alkyl of from 12 to 30 carbon atoms and a chloro-alkyl of from 12 to 30 carbon atoms, and wherein R is a tertiary alkyl having from 8 to 22 carbon atoms and said tertiary-alkyl is bonded to the nitrogen atom by the tertiary carbon atom.
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE608553D BE608553A (US08063081-20111122-C00044.png) | 1960-10-10 | ||
| FR874809A FR1309322A (fr) | 1960-10-10 | 1961-10-02 | Composition combustible à base de produits de distillation du pétrole |
| US175267A US3250600A (en) | 1960-10-10 | 1962-02-23 | Fuels containing n-tertiary-alkyl alkanesulfonamides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61371A US3238257A (en) | 1960-10-10 | 1960-10-10 | N-tertiary-alkyl alkanesulfonamides |
| US175267A US3250600A (en) | 1960-10-10 | 1962-02-23 | Fuels containing n-tertiary-alkyl alkanesulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3250600A true US3250600A (en) | 1966-05-10 |
Family
ID=26740992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US175267A Expired - Lifetime US3250600A (en) | 1960-10-10 | 1962-02-23 | Fuels containing n-tertiary-alkyl alkanesulfonamides |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3250600A (US08063081-20111122-C00044.png) |
| BE (1) | BE608553A (US08063081-20111122-C00044.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647378A (en) * | 1969-07-09 | 1972-03-07 | Armour Ind Chem Co | Carburetor anti-icing composition |
| US4066419A (en) * | 1975-12-19 | 1978-01-03 | Shell Oil Company | Gasoline compositions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2197851A (en) * | 1938-08-12 | 1940-04-23 | Du Pont | Motor fuel |
| US2236168A (en) * | 1940-02-27 | 1941-03-25 | Du Pont | Lubricant |
| US2582733A (en) * | 1949-11-05 | 1952-01-15 | Standard Oil Dev Co | Metal protecting compositions |
| US2906613A (en) * | 1956-06-21 | 1959-09-29 | Sun Oil Co | Suppression of fuel icing |
-
0
- BE BE608553D patent/BE608553A/xx unknown
-
1962
- 1962-02-23 US US175267A patent/US3250600A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2197851A (en) * | 1938-08-12 | 1940-04-23 | Du Pont | Motor fuel |
| US2236168A (en) * | 1940-02-27 | 1941-03-25 | Du Pont | Lubricant |
| US2582733A (en) * | 1949-11-05 | 1952-01-15 | Standard Oil Dev Co | Metal protecting compositions |
| US2906613A (en) * | 1956-06-21 | 1959-09-29 | Sun Oil Co | Suppression of fuel icing |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647378A (en) * | 1969-07-09 | 1972-03-07 | Armour Ind Chem Co | Carburetor anti-icing composition |
| US4066419A (en) * | 1975-12-19 | 1978-01-03 | Shell Oil Company | Gasoline compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE608553A (US08063081-20111122-C00044.png) |
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