US2697656A - Surface-active agents and oil compositions containing them - Google Patents
Surface-active agents and oil compositions containing them Download PDFInfo
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- US2697656A US2697656A US262996A US26299651A US2697656A US 2697656 A US2697656 A US 2697656A US 262996 A US262996 A US 262996A US 26299651 A US26299651 A US 26299651A US 2697656 A US2697656 A US 2697656A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- oil
- parts
- fuel oil
- alkylbenzyl
- 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
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- 239000000203 mixture Substances 0.000 title description 33
- 239000004094 surface-active agent Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000295 fuel oil Substances 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 239000000446 fuel Substances 0.000 description 25
- 239000004215 Carbon black (E152) Substances 0.000 description 23
- 229930195733 hydrocarbon Natural products 0.000 description 23
- 150000002430 hydrocarbons Chemical class 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- -1 hydroxyethyl groups Chemical group 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- 150000001555 benzenes Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000004471 Glycine Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000003209 petroleum derivative Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000006177 alkyl benzyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 150000002333 glycines Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QDXWVKAXCDGNKV-UHFFFAOYSA-N n-methyl-n-(2-phenylethyl)dodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCC1=CC=CC=C1 QDXWVKAXCDGNKV-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ISXDOPCKEDRLAY-UHFFFAOYSA-N 1-chlorotridecylbenzene Chemical compound CCCCCCCCCCCCC(Cl)C1=CC=CC=C1 ISXDOPCKEDRLAY-UHFFFAOYSA-N 0.000 description 1
- PQAHWOUEBKVMQH-UHFFFAOYSA-N 1-dodecyl-2-methylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1C PQAHWOUEBKVMQH-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FOUZISDNESEYLX-UHFFFAOYSA-N N-hydroxyethyl glycine Natural products OCCNCC(O)=O FOUZISDNESEYLX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- MKHSHEXPJPOVJV-UHFFFAOYSA-L calcium;2-iodoacetate Chemical compound [Ca+2].[O-]C(=O)CI.[O-]C(=O)CI MKHSHEXPJPOVJV-UHFFFAOYSA-L 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003747 fuel oil additive Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- SUYHVQFAQPEJLE-UHFFFAOYSA-L magnesium;2-chloroacetate Chemical compound [Mg+2].[O-]C(=O)CCl.[O-]C(=O)CCl SUYHVQFAQPEJLE-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940078490 n,n-dimethylglycine Drugs 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- LIXVMPBOGDCSRM-UHFFFAOYSA-N nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1 LIXVMPBOGDCSRM-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- CKTDIEJGPJZFOA-UHFFFAOYSA-M potassium;2-bromopropanoate Chemical compound [K+].CC(Br)C([O-])=O CKTDIEJGPJZFOA-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- XSRQGXVWFDYHQT-UHFFFAOYSA-N propan-2-yl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC(C)C XSRQGXVWFDYHQT-UHFFFAOYSA-N 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
Definitions
- This invention relates to new and useful oil-soluble surface-active agents and compositions containing them. More particularly, this invention relates to oil-soluble surface-active agents of an ionic nature which contain both an ionic carboxyl group and a cationic quaternary ammonium group within the same molecule and to improved hydrocarbon oil compositions containing them.
- new and useful oil-soluble ampholytic surface-active agents having both cationic and anionic characteristics may be prepared by reacting a di-(alkylarylrnethylene)-alkanolamine, a di-(alkylarylmethylene)- alkylamine, an alkylarylmethylene dialkanolamine or an alkylarylmethylene dialkylamine with an alkali metal or alkaline earth salt or an alkyl ester of a monohalogenated aliphatic carboxylic acid.
- the novel products thus obtained may be illustrated by the following structural formula:
- R1, R2 and R3 are long-chain alkylarylmethylene groups having from 9 to 18 carbon atoms in each long-chain alkyl substituent, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms and R4 is an alkylene group of from 1 to 7 carbon atoms.
- the above compounds are generally useful as surfaceactive agents. They are oil-soluble and are useful in hydrocarbon oil compositions such as lubricating oils and fuel oils as dispersing agents and rust inhibitors. their unusual amphoIytic or ,amphoteric nature, these compounds combine some of the beneficial aspects of both r cationic and anionic surface-active agents.
- the compounds as illustrated in the above structural formula contain at least one alkylaryl group, each of which is connected by a methylene linkage to the nitrogen.
- suitable aryl groups include benzene, naphthalene, anthracene, toluene, xylene, mesitylene, etc. with benzene and toluene being preferred for their availability and the high degree of effectiveness characteristic of the compounds containing them.
- the alkyl substituents on the aryl nucleus may be straight-chain or branched-chain in, nature and may vary from 9 to 18 carbon atoms in length.
- propylene polymers containing from 9 to 18, and more specifically from 12 to 15, carbon atoms per mole cule are preferred because of their ready availability and their chemical stability derived, apparently, from the characteristically moderate chain-branching of the propylene polymers in general.
- the N-alkyl or N-hydroxyalkyl portion may be'con- Due to veniently derived from any primary alkyl or hydroxy.
- alkylene group R4 in the structural formula is determined by the particular monohalogenated aliphatic carboxylic acid salt or ester employed in the preparation of the compounds according to the invention.
- Suitable halogenated acid salts or esters include sodium monochloroacetate, potassium monobromopropionate, sodium a-bromo n-butyrate, potassium a-bromo valerate, calcium iodoacetate, magnesium chloroacetate, methyl monochloroacetate, isopropyl monobromo-n-butyrate, etc.
- sodium monochloroacetate and methyl chloroacetate are presently preferred.
- N,N-di-(alkylbenzyl) and N-alkylbenzyl glycines constituting the preferred embodiment of the invention may be illustrated by the formula:
- R is a long-chain alkyl group of from 9 to 18 carbon atoms
- R is a member of the group consisting of hydrogen and methyl
- x is an integer of from 1 to 3
- R" is a member selected from the class consisting of methyl, ethyl and hydroxyethyl groups.
- Suitable alkylbenzenes, alkyltoluenes, or alkylxylenes such as nonylbenzene, dodecylbenzene, dodecyltoluene, etc. may be chloromethylated by suitable means, as, for example, by reacting them with formaldehyde or para-formaldehyde and hydrogen chloride in the presence of a catalyst such as an anhydrous mixture of zinc chloride and acetic acid.
- the resulting alkylbenzyl chloride is a very stable and highly reactive intermediate which may be condensed with any of the aforementioned primary and secondary amines to produce the N,N di-(alkylbenzyl)- and N-alkylbenzyl tertiary amines used in the preparation of the compounds of this invention. It reacts much more cleanly with the primary and secondary amines than would the corresponding long-chain alkyl halides and the N,N-di-(alkylbenzyl)-.' and N-alkylbenzyl glycines derived from the resulting tertiary amines are remarkably free of undesirable by-products of side reactions.
- the condensation of the alkylbenzyl chloride with the primary or secondary amine or amine salt to form the corresponding tertiary amines as referred to above may be carried out according to any suitable method known .to the art.
- the alkylbenzyl chloride and amine be condensed with the aid of a mild neutralization agent, such as sodium bicarbonate, while warming the reaction mixture slightly, usually in the temperature range of from to 200 F.
- N,N-di-(alkylbenzyl)-N-alkanolor alkyl tertiary amines or N-alkylbenzyl-N,N-dialkanolor dialkyl tertiary amines resulting from the foregoing preparations may then be reacted with a suitable salt or ester of a monohalogenated aliphatic carboxylic acid of the type described above, such as, sodium monochloroacetate .or methyl chloroacetate, to form the oil-soluble ampholytic surface-active agents of this invention.
- a suitable salt or ester of a monohalogenated aliphatic carboxylic acid of the type described above such as, sodium monochloroacetate .or methyl chloroacetate
- reaction may be carried out in the presence of an inorganic iodide, such as potassium iodide, which acts as a promoter and the mixture may be warmed sli htly to a temperature in the ran e of from 100 to 200 F.
- an inorganic iodide such as potassium iodide
- Example 2 Preparation of N,N-di-(ddecylbenzyl)- N-Z-hydroxyethyl glycine
- An isopropanol solution of 52 parts of N,N-di-(dodecylbenzyl)-ethanolamine prepared in Example 1 was refluxed with 13 parts of sodium chloroacetate and 3 parts of potassium iodide for 12 hours. The mixture was then filtered to remove inorganic salts and the solution washed with water and extracted with mixed hexanes. The mixed hexane solution was then evaporated under reduced pressure to give the N,N-di-(dodecylbenzyl)-N-2- hydroxyethyl glycine in the form of a viscous, yellow liquid.
- Example 3 Preparation of N-nonylbenzyl-dz'ethanolamine
- the alcoholic portion was alkalized to pH 10.0 with per cent sodium hydroxide solution and the product extracted with 200 parts of mixed hexanes.
- Example 4 Preparati0n of N-nonylbenzyl-N,N-di-(2- hydroxyethyl) -glycz'ne
- a solution of 16 parts of sodium bicarbonate in 150 parts of water was added portionwise and the mixture was again refluxed for 3 hours. The pH was adjusted to 9.5 with caustic and the solution was refluxed two hours, cooled, diluted with 200 parts of methanol'and then extracted with mixed hexanes.
- Example 5 Preparation of N-dodecylbenzyl-N,N- dimethylamine ture was refluxed two hours, filtered and acidified to pH 2.0 w th concentrated hydrochloric acid. The solution was extracted with two part portions of mixed hexanes and then alkalized to pH 8.5 with caustic solution. The product was taken up in mixed hexanes, washed with water, concentrated by evaporation of most of the solvent and then distilled collecting the fraction boiling at 266 to 293 F. at 2 mm. There was obtained 34 parts of N-dodecy1benzyl-N,N-dimethylamine as a colorless liquid.
- Example 6 Preparati0n 0f N-dodecylbenzyl-N,N- dimethylglycine
- the mixture was stirred and refluxed for six hours, filtered and made alkaline with caustic.
- the alcoholic solution was washed first with two 100-part portions of mixed hexanes and then with two 100-part portions of water.
- the present invention is also concerned with the preparation of improved hydrocarbon fuels and, more particularly, with hydrocarbon fuels having improved properties as burner, diesel and jet fuels.
- Burner, diesel and jet fuel systems ordinarily contain certain amounts of water due to vapor condensation.
- the presence of this water tends to accelerate the formation of filter plugging gum and sludge in such fuels, particularly those containing cracking stocks, and also cause rusting of exposed ferrous metal surfaces which ust in turn eventually loosens and clogs the filters and mes.
- the hydrocarbon fuel base stocks suitable for use in the improved fuel oil compositions of the present invention may be described broadly as petroleum distillates b i ing in the ran e of from about 350 F. to about 750 F. Such distillates are ordinarily characterized by an APT ravity of at least 20 degrees and usuallv at least 25 de rees.
- the base stocks may be either straightrun distillates or cracked distillates.
- the present invention finds its greatest utility in hydrocarbon fuels of the preceding tvoes which contain substantial amounts of cracked distillates. Without the additives of this invention, such fuels form ap reciable amounts of filter plugging sludge and gum which render them unsuitable for use in operations where interrupted service is desired, as is the case with most present-day operations.
- the filter is compared with a standard series of 11 filters prepared in a similar manner from fuels of known filter-plugging tendency.
- the standard filters are numbered 0 to 10, the higher numbers being identified with the higher deposits.
- IFD Interface Filter Deposit Rating
- Table I which follows, shows the IFD values of a number of fuel oil compositions according to the present invention as compared with a standard diesel, burner or jet fuel.
- the base fuel employed in each case was a mixture of equal parts of straight run distillate from a waxy base crude boiling in the range of from 384 F. to 675 F. and a Thermofor catalytic cracked fraction boiling in the range of from 376 F. to 566 F.
- the fuel oil compositions of the present invention were also tested for their rust-inhibiting properties.
- the tests were carried out in accordance with the procedure outlined in ASTM method D665-47T. Steel spindles were immerged in an agitated distilled water and fuel oil mixture containing 0.001% by weight of additive and in an agitated sea water and fuel oil mixture containing 0.005% by weight of additive.
- the base stock fuel was tested in a similar fashion. The results of these tests are as From the above tests it will be readily observed that the improved fuel oil compositions of this invention p'ossess remarkable rust-inhibiting properties as compared to ordinary diesel, jet or burner fuels.
- the fuel oil compositions according to the present invention may also contain other fuel oil additives in addition to the oil-soluble ampholytic surface-active agents of this invention.
- additives include: lecithin; oil-soluble alkylaryl polyglycol ethers such as didodecylphenyl-dodecaethylene glycol ether; oil-soluble sulfonates such as the lead salts of petroleum sulfonic acids containing from about 20 to 30 carbon atoms per molecule; oil-soluble naphthenates such as the alkali metal and lead salts of petroleum naphthenic acids; alaali metal and lead salts of alkylphenyl disulfides.
- Oil-soluble surface active compounds having the formula:
- R1, R and R are long-chain alkylbenzyl groups having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms.
- Oil-soluble surface active N,N-di-(alkylbenzyl)-N- alkanol glycines having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkanol substituent on the nitrogen containing from 1 to 7 carbon atoms.
- Oil-soluble surface active N,N-di-(alkylbenzyl)-N- alkyl glycines having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkyl substituent on the nitrogen containing from 1 to 7 carbon atoms.
- a process which comprises heating at a temperature between about and 200 F. 2 molar proportions of an alkylbenzyl chloride having from 9 to 18 carbon atoms in the alkyl portion thereof with 1 molar proportion of ethanolamine in the presence of sodium bicarbonate, heating at a temperature between about 100 and 200 F. the N,N-di-(alkylbenzyl)-ethanolamine thus obtained with sodium monochloroacetate in the presence of potassium iodide to give an oil-soluble, surface-active N,N-di-(alkylbenzyl)-N-2-hydroxyethyl glycine having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms.
- R1, R2 and R3 are long-chain alkylbenzyl groups having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms.
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufiicient to inhibit line and filter clogging and corrosion of an N,N-di-(alkylbenzyl)-N- alkanol glycine having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkanol substituent on the nitrogen containing from 1 to 7 carbon atoms.
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufficient to inhibit line and filter clogging and corrosion of an N-alkylbenz yl-N,N-dialka- 1101 glycine having a long-chain alkyl substituent on the benzene containing from 9 to 18 carbon atoms and alkanol substituents on the nitrogen containing from 1 to 7 carbon atoms each.
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufiicient to inhibit line and filter clogging and corrosion of an N,N-di-(alky1benzyl)- N-alkyl glycine having a long-chain alkyl substituent on each benzene nucleus and containing from 9 to 18 carbon atoms and an alkyl substituent on the nitrogen containing from 1 to 7 carbon atoms.
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N,N-di-(dodecylbenzyl)-N-methyl glycine, said fuel oil containing a substantial proportion of cracked petroleum distillate.
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N,N di (dodecylbenzyl)-N-2-hydroxyethyl glycine,
- a hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N-dodecylbenzyl-N,N-di-Z-hydroxyethyl glycine, said fuel oil containing a substantial proportion of cracked petroleum distillate.
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Description
United States Patent SURFACE-ACTIVE AGENTS AND OIL COMPOSI- TIONS CONTAINING THEM Richard D. Stayner and Robert A. Stayner, Berkeley,
No Drawing. Application December 22, 1951, Serial No. 262,996
Claims. (Cl. 52--0.5)
This invention relates to new and useful oil-soluble surface-active agents and compositions containing them. More particularly, this invention relates to oil-soluble surface-active agents of an ionic nature which contain both an ionic carboxyl group and a cationic quaternary ammonium group within the same molecule and to improved hydrocarbon oil compositions containing them.
In accordance with the present invention, it has been discovered that new and useful oil-soluble ampholytic surface-active agents having both cationic and anionic characteristics may be prepared by reacting a di-(alkylarylrnethylene)-alkanolamine, a di-(alkylarylmethylene)- alkylamine, an alkylarylmethylene dialkanolamine or an alkylarylmethylene dialkylamine with an alkali metal or alkaline earth salt or an alkyl ester of a monohalogenated aliphatic carboxylic acid. The novel products thus obtained may be illustrated by the following structural formula:
wherein at least one but not more than two of the groups R1, R2 and R3 are long-chain alkylarylmethylene groups having from 9 to 18 carbon atoms in each long-chain alkyl substituent, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms and R4 is an alkylene group of from 1 to 7 carbon atoms.
The above compounds are generally useful as surfaceactive agents. They are oil-soluble and are useful in hydrocarbon oil compositions such as lubricating oils and fuel oils as dispersing agents and rust inhibitors. their unusual amphoIytic or ,amphoteric nature, these compounds combine some of the beneficial aspects of both r cationic and anionic surface-active agents.
According to the invention, the compounds as illustrated in the above structural formula contain at least one alkylaryl group, each of which is connected by a methylene linkage to the nitrogen. Examples of suitable aryl groups include benzene, naphthalene, anthracene, toluene, xylene, mesitylene, etc. with benzene and toluene being preferred for their availability and the high degree of effectiveness characteristic of the compounds containing them. The alkyl substituents on the aryl nucleus may be straight-chain or branched-chain in, nature and may vary from 9 to 18 carbon atoms in length. For present purposes propylene polymers containing from 9 to 18, and more specifically from 12 to 15, carbon atoms per mole cule are preferred because of their ready availability and their chemical stability derived, apparently, from the characteristically moderate chain-branching of the propylene polymers in general.
In the above structural formula illustrating the invention, the N-alkyl or N-hydroxyalkyl portion may be'con- Due to veniently derived from any primary alkyl or hydroxy.
.89 amine, butanolam ne, d meth ylarmne hydrochloride, d1-
2,697,656 Patented Dec. 21, 1954 ice isopropylamine hydrochloride, etc. Methylamine, dimethylamine, dimethylamine hydrochloride, ethylamine, ethanolamine and di-ethanolamine are presently preferred.
The nature of the alkylene group R4 in the structural formula is determined by the particular monohalogenated aliphatic carboxylic acid salt or ester employed in the preparation of the compounds according to the invention. Suitable halogenated acid salts or esters include sodium monochloroacetate, potassium monobromopropionate, sodium a-bromo n-butyrate, potassium a-bromo valerate, calcium iodoacetate, magnesium chloroacetate, methyl monochloroacetate, isopropyl monobromo-n-butyrate, etc. For their effectiveness and ready availability sodium monochloroacetate and methyl chloroacetate are presently preferred.
The N,N-di-(alkylbenzyl) and N-alkylbenzyl glycines constituting the preferred embodiment of the invention may be illustrated by the formula:
wherein R is a long-chain alkyl group of from 9 to 18 carbon atoms, R is a member of the group consisting of hydrogen and methyl, x is an integer of from 1 to 3 and R" is a member selected from the class consisting of methyl, ethyl and hydroxyethyl groups.
An important advantage of the present invention lies in the process whereby the above preferred group of compounds may be prepared. Suitable alkylbenzenes, alkyltoluenes, or alkylxylenes such as nonylbenzene, dodecylbenzene, dodecyltoluene, etc. may be chloromethylated by suitable means, as, for example, by reacting them with formaldehyde or para-formaldehyde and hydrogen chloride in the presence of a catalyst such as an anhydrous mixture of zinc chloride and acetic acid. The resulting alkylbenzyl chloride is a very stable and highly reactive intermediate which may be condensed with any of the aforementioned primary and secondary amines to produce the N,N di-(alkylbenzyl)- and N-alkylbenzyl tertiary amines used in the preparation of the compounds of this invention. It reacts much more cleanly with the primary and secondary amines than would the corresponding long-chain alkyl halides and the N,N-di-(alkylbenzyl)-.' and N-alkylbenzyl glycines derived from the resulting tertiary amines are remarkably free of undesirable by-products of side reactions.
The condensation of the alkylbenzyl chloride with the primary or secondary amine or amine salt to form the corresponding tertiary amines as referred to above may be carried out according to any suitable method known .to the art. For present purposes it is preferred that the alkylbenzyl chloride and amine be condensed with the aid of a mild neutralization agent, such as sodium bicarbonate, while warming the reaction mixture slightly, usually in the temperature range of from to 200 F.
The N,N-di-(alkylbenzyl)-N-alkanolor alkyl tertiary amines or N-alkylbenzyl-N,N-dialkanolor dialkyl tertiary amines resulting from the foregoing preparations may then be reacted with a suitable salt or ester of a monohalogenated aliphatic carboxylic acid of the type described above, such as, sodium monochloroacetate .or methyl chloroacetate, to form the oil-soluble ampholytic surface-active agents of this invention. If desired, the
reaction may be carried out in the presence of an inorganic iodide, such as potassium iodide, which acts as a promoter and the mixture may be warmed sli htly to a temperature in the ran e of from 100 to 200 F.
For convenience of handling, solvents for the above reaction mixtures may be employed. Suitable solvents Example I.Preparation of N,N-di-(dodecylbenzyl)- ethanolamine 140 parts of dodecylbenzyl chloride was added dropwise to a mixture of 15% parts of ethanolamine and 42 parts of sodium bicarbonate in an isopropanol-water solution. The addition was carried out over a period of one hour at a temperature of from 120 to 125 F. Following the addition, the stirred mixture was refluxed for two hours, filtered to remove inorganic salts and then diluted with mixed hexanes. The diluted solution was next washed with water, dried over anhydrous calcium sulfate and concentrated under reduced pressure to give 143 parts of N,N-di-(dodecylbenzyl)-ethanolamine in the form of yellow oil.
Example 2.Preparation of N,N-di-(ddecylbenzyl)- N-Z-hydroxyethyl glycine An isopropanol solution of 52 parts of N,N-di-(dodecylbenzyl)-ethanolamine prepared in Example 1 was refluxed with 13 parts of sodium chloroacetate and 3 parts of potassium iodide for 12 hours. The mixture was then filtered to remove inorganic salts and the solution washed with water and extracted with mixed hexanes. The mixed hexane solution was then evaporated under reduced pressure to give the N,N-di-(dodecylbenzyl)-N-2- hydroxyethyl glycine in the form of a viscous, yellow liquid.
Example 3.Preparation of N-nonylbenzyl-dz'ethanolamine The alcoholic portion was alkalized to pH 10.0 with per cent sodium hydroxide solution and the product extracted with 200 parts of mixed hexanes. The hexane solution was then washed with water and concentrated under reduced pressure to give 46 parts of N-nonylbenzyldiethanolamine as a viscous, yellow liquid. Analysis: per cent N (calc.)=4.37; per cent N (found)=4.11.
Example 4.--Preparati0n of N-nonylbenzyl-N,N-di-(2- hydroxyethyl) -glycz'ne A mixture of 41 parts of N-nonylbenzyl-diethanolamine (prepared in Example 3), 23 parts of methyl chloroacetate, 5 parts of potassium iodide and 100 parts of ethyl alcohol was stirred and refluxed for hours. A solution of 16 parts of sodium bicarbonate in 150 parts of water was added portionwise and the mixture was again refluxed for 3 hours. The pH was adjusted to 9.5 with caustic and the solution was refluxed two hours, cooled, diluted with 200 parts of methanol'and then extracted with mixed hexanes. The alcoholic portion was washed with water and the product concentrated under reduced pressure to give 24 parts of N-nonylbenzyl-N,N- di-(Lhydroxyethyl)-glycine as a yellow-colored, viscous liouid. Analvsis: per cent N (calc.)=3.70; per cent N (found)=3.68.
Example 5.Preparation of N-dodecylbenzyl-N,N- dimethylamine ture was refluxed two hours, filtered and acidified to pH 2.0 w th concentrated hydrochloric acid. The solution was extracted with two part portions of mixed hexanes and then alkalized to pH 8.5 with caustic solution. The product was taken up in mixed hexanes, washed with water, concentrated by evaporation of most of the solvent and then distilled collecting the fraction boiling at 266 to 293 F. at 2 mm. There was obtained 34 parts of N-dodecy1benzyl-N,N-dimethylamine as a colorless liquid.
Example 6.Preparati0n 0f N-dodecylbenzyl-N,N- dimethylglycine A stirred mixture of 4.7 parts of chloroacetic acid, 2.8 parts of potassium hydroxide and 100 parts of ethanol was warmed slowly to F. until the solution became clear, and then 3.1 parts of potassium iodide and 12.5 parts of N-dodecylbenzyl-N,N-dimethylamine (prepared in Example 5) were added. The mixture was stirred and refluxed for six hours, filtered and made alkaline with caustic. The alcoholic solution was washed first with two 100-part portions of mixed hexanes and then with two 100-part portions of water. The product was dissolved in 50 parts of benzene and then concentrated under reduced pressure to give 12 parts of N-dodecylbenzyl- N,N-dirnethylglycine as a colorless grease. Analysis: per cent N (ca1c.)=3.75; (found)=3.50.
The proportions given in the foregoing examples are on a weight basis unless otherwise specified.
' As mentioned above, the present invention is also concerned with the preparation of improved hydrocarbon fuels and, more particularly, with hydrocarbon fuels having improved properties as burner, diesel and jet fuels.
In the production of burner fuels, diesel and jet fuels, it is desirable, economically, to employ considerable quantities of cracked refinery stocks. Such stocks are becoming more and more available due to the everincreasing use of thermal and catalytic cracking processes in petroleum refinery operations. When employed in burner fuels and diesel and jet fuels, these stocks have the disadvantage of forming particles of sludge or gum which tend to deposit and cause plugging of filters, screens and lines. The necessity for frequent interruptions of burner and diesel engine service to replace or unplug clogged filters and screens constitutes a serious problem.
Burner, diesel and jet fuel systems ordinarily contain certain amounts of water due to vapor condensation. The presence of this water tends to accelerate the formation of filter plugging gum and sludge in such fuels, particularly those containing cracking stocks, and also cause rusting of exposed ferrous metal surfaces which ust in turn eventually loosens and clogs the filters and mes.
As part of the present inventionit has been discovered that by the addition of a small amount of an oil-soluble ampholytic surface-active agent of the type described above to normally liquid hydrocarbon fuels, anv tendency of the fuel to form filter clogging particles of sludge or gum is substantially overcome. Such hydrocarbon fuel compositions, in addition, have the effect of inhibiting rusting of ferrous metal surfaces with which they come in contact, thus substantially eliminating rust particles that may also lead to clogging of fuel oil systems.
The hydrocarbon fuel base stocks suitable for use in the improved fuel oil compositions of the present invention may be described broadly as petroleum distillates b i ing in the ran e of from about 350 F. to about 750 F. Such distillates are ordinarily characterized by an APT ravity of at least 20 degrees and usuallv at least 25 de rees. The base stocks may be either straightrun distillates or cracked distillates. The present invention finds its greatest utility in hydrocarbon fuels of the preceding tvoes which contain substantial amounts of cracked distillates. Without the additives of this invention, such fuels form ap reciable amounts of filter plugging sludge and gum which render them unsuitable for use in operations where interrupted service is desired, as is the case with most present-day operations.
Very small amounts of the additives, in the order of 1% by weight or less, have been found to be entirely effective for a prevention of line and filter clogging and also the inhibition of rusting when Water is present in the system. Amounts in the range of from 0.001 to 0.20% by weight of the total fuel are particularly suitable and proportions in the range of from 0.005 to 0.015% by weight are most preferred in the more specific embodiments of the invention.
s .-In order to facilitate'evaluation of the improved fuel oil compositions of the present'invention and avoid an enormous outlay of time and material, a rapid test method for determining filter plugging characteristics was developed. The results of this test method have been found to correlate well with actual field tests, using regular fuel oil burners and diesel and jet engines. The test is carried out by mixing 500 milliliters of a fuel composition containing 0.01% by weight of additive with 500 milliliters of water containing 102 parts per million hardness calculated as calcium and magnesium carbonates, two-thirds being calcium carbonate. The fuel oil composition and water are shaken in a separatory funnel for 30 seconds, at the end of which they are allowed to. stand for minutes. At this point a phase separation occurs and an upper oil layer and a-lower water layer are obtained, usually separated by an opaque cutf attheir interface. This interface cuff is then filtered through a fritted glass crucible with the aid of a vacuum. Only as much oil and water are filtered as are necessary to assure complete extraction of the cuff, usually about milliliters. However, in cases of severe emulsions the entire content of the separatory funnel may have to be filtered. The resultant discoloration of the crucible mat by the particles of gum and sludge deposited is used as a comparative measure of the hydrocarbon fuels tendency to plug filters and screens.
In the comparison, the filter is compared with a standard series of 11 filters prepared in a similar manner from fuels of known filter-plugging tendency. The standard filters are numbered 0 to 10, the higher numbers being identified with the higher deposits. For convenience, the rating given a particular test sample is termed its Interface Filter Deposit Rating (IFD) and denotes the number of the filter in the standard series with which it compares in amount of filter deposit.
Table I, which follows, shows the IFD values of a number of fuel oil compositions according to the present invention as compared with a standard diesel, burner or jet fuel. The base fuel employed in each case was a mixture of equal parts of straight run distillate from a waxy base crude boiling in the range of from 384 F. to 675 F. and a Thermofor catalytic cracked fraction boiling in the range of from 376 F. to 566 F.
The data in Table I above clearly shows the marked superiority of the improved hydrocarbon fuel compositions according to the present invention over a conventional diesel, jet or burner fuel. Run 1 shows that no filter deposit is obtained from fuel oil compositions containing a representative agent, whereas the fuel oil base stock itself gives an extremely high filter deposit.
The fuel oil compositions of the present invention were also tested for their rust-inhibiting properties. The tests were carried out in accordance with the procedure outlined in ASTM method D665-47T. Steel spindles were immerged in an agitated distilled water and fuel oil mixture containing 0.001% by weight of additive and in an agitated sea water and fuel oil mixture containing 0.005% by weight of additive. The base stock fuel was tested in a similar fashion. The results of these tests are as From the above tests it will be readily observed that the improved fuel oil compositions of this invention p'ossess remarkable rust-inhibiting properties as compared to ordinary diesel, jet or burner fuels.
The fuel oil compositions according to the present invention may also contain other fuel oil additives in addition to the oil-soluble ampholytic surface-active agents of this invention. Such additives include: lecithin; oil-soluble alkylaryl polyglycol ethers such as didodecylphenyl-dodecaethylene glycol ether; oil-soluble sulfonates such as the lead salts of petroleum sulfonic acids containing from about 20 to 30 carbon atoms per molecule; oil-soluble naphthenates such as the alkali metal and lead salts of petroleum naphthenic acids; alaali metal and lead salts of alkylphenyl disulfides.
We claim:
1. Oil-soluble surface active compounds having the formula:
wherein at least one but not more than two of the groups R1, R and R are long-chain alkylbenzyl groups having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms.
2. Oil-soluble surface active N,N-di-(alkylbenzyl)-N- alkanol glycines having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkanol substituent on the nitrogen containing from 1 to 7 carbon atoms.
3. Oil-soluble surface active N,N-di-(alkylbenzyl)-N- alkyl glycines having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkyl substituent on the nitrogen containing from 1 to 7 carbon atoms.
4. Oil-soluble surface active N-alkylbenzyl-N,N-dialkanol glycines having a long-chain alkyl substituent on the benzene nucleus containing from 9 to 18 carbon atoms and alkanol substituents on the nitrogen containing from 1 to 7 carbon atoms each.
5. N,N-di-(dodecylbenzyl)-N-methyl glycine.
6. N-dodecylbenzyl-N,N-di-Z-hydroxyethyl glycine.
7. N,N-di-(dodecylbenzyl)-N-2-hydroxyethyl glycine.
8. A process which comprises heating at a temperature between about and 200 F. 2 molar proportions of an alkylbenzyl chloride having from 9 to 18 carbon atoms in the alkyl portion thereof with 1 molar proportion of ethanolamine in the presence of sodium bicarbonate, heating at a temperature between about 100 and 200 F. the N,N-di-(alkylbenzyl)-ethanolamine thus obtained with sodium monochloroacetate in the presence of potassium iodide to give an oil-soluble, surface-active N,N-di-(alkylbenzyl)-N-2-hydroxyethyl glycine having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms.
9. A hydrocarbon oil composition containing a small amount suflicient to inhibit line and filter clogging and corrosion of a compound having the following formula:
wherein at least one but not more than two of the groups R1, R2 and R3 are long-chain alkylbenzyl groups having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms, the remainder being members of the class consisting of short-chain alkyl and hydroxyalkyl groups containing from 1 to 7 carbon atoms.
10. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufiicient to inhibit line and filter clogging and corrosion of an N,N-di-(alkylbenzyl)-N- alkanol glycine having a long-chain alkyl substituent on each benzene nucleus containing from 9 to 18 carbon atoms and an alkanol substituent on the nitrogen containing from 1 to 7 carbon atoms.
11. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufficient to inhibit line and filter clogging and corrosion of an N-alkylbenz yl-N,N-dialka- 1101 glycine having a long-chain alkyl substituent on the benzene containing from 9 to 18 carbon atoms and alkanol substituents on the nitrogen containing from 1 to 7 carbon atoms each.
12. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil and a small amount sufiicient to inhibit line and filter clogging and corrosion of an N,N-di-(alky1benzyl)- N-alkyl glycine having a long-chain alkyl substituent on each benzene nucleus and containing from 9 to 18 carbon atoms and an alkyl substituent on the nitrogen containing from 1 to 7 carbon atoms.
13. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N,N-di-(dodecylbenzyl)-N-methyl glycine, said fuel oil containing a substantial proportion of cracked petroleum distillate.
14. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N,N di (dodecylbenzyl)-N-2-hydroxyethyl glycine,
' 8 said 'fuel oil containing a substantial proportion of cracked petroleum distillate.
15. A hydrocarbon fuel oil composition comprising a major proportion of a normally liquid hydrocarbon fuel oil boiling in the range of from about 350 F. to about 750 F. and a small amount not exceeding 1% by weight of N-dodecylbenzyl-N,N-di-Z-hydroxyethyl glycine, said fuel oil containing a substantial proportion of cracked petroleum distillate.
Claims (1)
1. OIL-SOLUBLE SURFACE ACTIVE COMPOUNDS HAVING THE FORMULA:
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US2777872A (en) * | 1953-11-02 | 1957-01-15 | Du Pont | Unsaturated organic compounds |
US2886423A (en) * | 1956-07-09 | 1959-05-12 | American Cyanamid Co | Hydrocarbon fuels containing betaine antifreeze compositions |
US3027246A (en) * | 1958-11-03 | 1962-03-27 | Du Pont | Liquid hydrocarbon distillate fuels containing hydrocarbon-soluble betaines as antistatic agents |
US3092474A (en) * | 1960-04-25 | 1963-06-04 | Standard Oil Co | Fuel oil composition |
US3198613A (en) * | 1962-08-20 | 1965-08-03 | Standard Oil Co | Fuel oil composition |
US3231581A (en) * | 1966-01-25 | Imidazglinium derivatives | ||
US3231580A (en) * | 1961-06-30 | 1966-01-25 | Hans S Mannheimer | Substituted imidazolines |
US3230700A (en) * | 1958-10-27 | 1966-01-25 | Phillips Petroleum Co | Rocket propulsion method using hydrocarbon fuels containing aminoalkyl acrylate polymers |
DE2452662A1 (en) * | 1973-11-07 | 1975-05-22 | Lubrizol Corp | LIQUID FUEL AND FUEL MIXTURES BASED ON HYDROCARBONS |
US4314060A (en) * | 1979-07-16 | 1982-02-02 | The Procter & Gamble Company | Oxaalkanoate anti-ulcer compounds |
US4834892A (en) * | 1985-10-03 | 1989-05-30 | Elf France | Additives for lubricating oils, their process of preparation and lubricating compositions containing them |
US5135668A (en) * | 1990-02-09 | 1992-08-04 | Scandinavian Oilfield Chemicals A/S | Process for inhibiting corrosion in oil production fluids |
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US3231581A (en) * | 1966-01-25 | Imidazglinium derivatives | ||
US2777872A (en) * | 1953-11-02 | 1957-01-15 | Du Pont | Unsaturated organic compounds |
US2886423A (en) * | 1956-07-09 | 1959-05-12 | American Cyanamid Co | Hydrocarbon fuels containing betaine antifreeze compositions |
US3230700A (en) * | 1958-10-27 | 1966-01-25 | Phillips Petroleum Co | Rocket propulsion method using hydrocarbon fuels containing aminoalkyl acrylate polymers |
US3027246A (en) * | 1958-11-03 | 1962-03-27 | Du Pont | Liquid hydrocarbon distillate fuels containing hydrocarbon-soluble betaines as antistatic agents |
US3092474A (en) * | 1960-04-25 | 1963-06-04 | Standard Oil Co | Fuel oil composition |
US3231580A (en) * | 1961-06-30 | 1966-01-25 | Hans S Mannheimer | Substituted imidazolines |
US3198613A (en) * | 1962-08-20 | 1965-08-03 | Standard Oil Co | Fuel oil composition |
DE2452662A1 (en) * | 1973-11-07 | 1975-05-22 | Lubrizol Corp | LIQUID FUEL AND FUEL MIXTURES BASED ON HYDROCARBONS |
US4071327A (en) * | 1973-11-07 | 1978-01-31 | The Lubrizol Corporation | Salts of Mannich bases and derivatives thereof |
US4314060A (en) * | 1979-07-16 | 1982-02-02 | The Procter & Gamble Company | Oxaalkanoate anti-ulcer compounds |
US4834892A (en) * | 1985-10-03 | 1989-05-30 | Elf France | Additives for lubricating oils, their process of preparation and lubricating compositions containing them |
US5135668A (en) * | 1990-02-09 | 1992-08-04 | Scandinavian Oilfield Chemicals A/S | Process for inhibiting corrosion in oil production fluids |
EP0536950A1 (en) * | 1991-10-10 | 1993-04-14 | The British Petroleum Company P.L.C. | Method for inhibiting hydrate formation |
US5331105A (en) * | 1991-10-10 | 1994-07-19 | The British Petroleum Company P.L.C. | Method for inhibiting hydrate formation |
US20080060608A1 (en) * | 2006-09-07 | 2008-03-13 | Angela Priscilla Breakspear | Method and use for the prevention of fuel injector deposits |
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