US3230058A - Additive for hydrocarbon fuels - Google Patents
Additive for hydrocarbon fuels Download PDFInfo
- Publication number
- US3230058A US3230058A US153727A US15372761A US3230058A US 3230058 A US3230058 A US 3230058A US 153727 A US153727 A US 153727A US 15372761 A US15372761 A US 15372761A US 3230058 A US3230058 A US 3230058A
- Authority
- US
- United States
- Prior art keywords
- fuel
- additive
- hydrocarbon
- fuels
- volume percent
- 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 117
- 229930195733 hydrocarbon Natural products 0.000 title claims description 41
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 38
- 239000000654 additive Substances 0.000 title claims description 37
- 230000000996 additive effect Effects 0.000 title claims description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- HNWNELAGDBSCDG-UHFFFAOYSA-O 2-hydroxyethyl-dimethyl-[3-(octadecanoylamino)propyl]azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCCCC(=O)NCCC[N+](C)(C)CCO HNWNELAGDBSCDG-UHFFFAOYSA-O 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- -1 deicers Substances 0.000 description 30
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 11
- 230000005611 electricity Effects 0.000 description 10
- 230000003068 static effect Effects 0.000 description 10
- 238000009825 accumulation Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000004880 explosion Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229910002651 NO3 Inorganic materials 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002816 fuel additive Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical compound CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- LZJIBRSVPKKOSI-UHFFFAOYSA-O ethanolammonium nitrate Chemical compound [NH3+]CCO.[O-][N+]([O-])=O LZJIBRSVPKKOSI-UHFFFAOYSA-O 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ZDAWZDFBPUUDAY-UHFFFAOYSA-N 2-Deoxy-D-ribitol Chemical compound OCCC(O)C(O)CO ZDAWZDFBPUUDAY-UHFFFAOYSA-N 0.000 description 1
- KCNRUFVEYNBDQY-UHFFFAOYSA-N 2-aminoethanol;carbonic acid Chemical compound [NH3+]CCO.[NH3+]CCO.[O-]C([O-])=O KCNRUFVEYNBDQY-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WBUUOQGFAPWFMC-UHFFFAOYSA-N 2-hydroxyethylazanium;iodide Chemical compound [I-].[NH3+]CCO WBUUOQGFAPWFMC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000010006 flight Effects 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 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
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000441 potassium aluminium silicate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011800 void material 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
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
-
- 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
Definitions
- This invention relates to an additive for hydrocarbon fuels.
- the invention relates to a hydrocarbon fuel inhibited against static electricity accumulation.
- the invention relates to a method of inhibiting ice formation and static electricity accumulation in volatile hydrocarbon fuels.
- An important property of a liquid hydrocarbon fuel which is frequently disturbed by the use of fuel additives is its ability to separate from water. Hydrocarbon fuels are frequently unavodably exposed to water or water vapor. Water is a very highly undesirable component in fuels, particularly when used in aircraft engines, for a host of reasons and, consequently, the fuel is passed through filters or water separators which dry the fuel when transferring the fuel from one point to another. The ability of the fuel to separate itself from water determines the efliciency of the water separation stage and is therefore an important fuel property. This property is disturbed when materials having surfactant properties are added to the fuel. Such additives tend to emulsify the water and to prevent its removal by the equipment utilized.
- Another object of the invention is to provide a novel method of operating a jet engine with a fuel supply system subject to subfreezing temperatures and static electricity accumulation.
- Yet another object of the invention is to provide an improved method of stabilizing a hydrocarbon fuel against ice formation and static electricity accumulation without adversely effecting water separability properties.
- a glycol ether is employed in conjunction with said nitrogenous compound.
- the additive of this invention comprises said nitrogenous compound, a glycol ether and a saturated acyclic polyhydroxy alcohol as hereinafter defined.
- a wide variety of monocarboxylic acids may supply R, such as, for example, caprylic acid, decenoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, oleic acid and other highly unsaturated fatty acids of 14 to 18 carbons obtained from vegetable and animal oil and fats such as soy'a bean oil, cotton seed oil, coconut oil, linseed oil, castor oil, dehydrated castor oil and the like, or from other sources such as tall oil.
- R such as, for example, caprylic acid, decenoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, oleic acid and other highly unsaturated fatty acids of 14 to 18 carbons obtained from vegetable and animal oil and fats such as soy'a bean oil, cotton seed oil, coconut oil, linseed oil, castor oil, dehydrated castor oil and the like, or from other sources such as tall oil.
- A-licyclic monocanboxylic acids which may be used include petroleum naphthenic acids of 7 to 14 carbon atoms having boiling points within the range of 215 to 310 C., as described in Ellis, Chemistry of Petroleum Derivatives (1934), pages 1062-1085, abietic acid, and the like.
- radicals represented by R in the aforesaid nitrogenous compound are normal and unbranched heptyl, octyl, octenyl, nonyl, nonenyl, decyl, decenyl, undecyl, undecenyl, tridecyl, tetradecyl, tetradecenyl, heptadecyl, heptadecenyl, octadecyl, octadecenyl, the residue of abietic acid and the like radicals.
- Illustrative examples of the radical represented by R and R are methyl, ethyl, propyl, isopropyl, hydroxyethyl, dihydroxyp-ropyl, trihydroxypropyl and the like radicals.
- Illustrative examples of R include hydroxymethy-l, hydroxyethyl, hydroxypropyl, dihydroxypropyl, and the like radicals.
- Illustrative examples of anions represented by Y are chloride, bromide, fluoride, iodide, sulfate, sulfonate, phosphate, hydroxide, borate, carbonate, hydrocarbonate, isocyanate, nitrate, nitrite, oxalate, acetate, hydrogen sulfate, thiocyanate, sulfite, bisulfi-te, silicate, sulfide, ethylsulfate, and other inorganic and organic ions.
- Representative nitrogenous compounds include:
- an additive comprising: (1) a blend of (A) a major proportion of a glycol ether having the formula R'(OCH 0H OH, where R is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, and tolyl groups, when R is hydrogen, x is 2 to 4, otherwise, x is 1 to 4, and (B) a minor amount of a saturated acyclic polyhydroxy alcohol having 3 to 5 carbon atoms per molecule, from 2 to 5 OH groups each attached to a different carbon and a ratio of hydroxy radicals to carbons in the range of 0.66:1 to 1: 1, said minor amount being sufficient to synergistically increase the antiicing properties of said blend when added to said hydrocarbon fuel; and (2) said hereinbefore-described nitrogenous compound, said nitrogenous compound being present in an amount suflicient to synergistically increase the electrical conduct
- glycol ethers which are employable in the additive of this invention include, among others, the following: methyl ether of ethylene glycol (methyl Cellosolve); ethyl ether of ethylene glycol (ethyl Cellosolve); butyl ether of ethylene glycol (butyl Cellosolve); methyl ether of diethylene glycol (methyl carbitol); ethyl ether of diethylene glycol (ethyl carbitod); butyl ether of dieth ylene glycol (butyl carbitol); methyl ether of triethylene glycol; ethyl ether of triethylene glycol; phenyl ether of ethylene glycol; tolyl ether of ethylene glycol; phenyl ether of triethylene glycol; tolyl ether of triethylene glycol; diethylene glycol; triethylene glycol; and tetraethylene glycol.
- a presently preferred group of glycol ethers suitable for use in the practice of the invention are those having the formula R(OCH CH OH wherein: R is selected from the group consisting of methyl, ethyl, propyl, and butyl groups, and x is an integer of fro-m 1 to 4.
- the most preferred glycol ethers are those of the above formula wherein R is methyl or ethyl and x is 1 or 2.
- saturated acyclic polyhydroxy alcohols include the following: 1,2-dihydroxypropane; 1,3- dihydroxypropane; glycerol; 1,2,3-trihydroxybutane; 1,2, 4 trihydroxybutane; 2 (hydroxymethyl)-1,3-dihydroxypropane; erythritol; pentaerythritol; l,2,3,4-tetrahydroxy pentane; 1,2,3,5 tetrahydroxypentane; l,2,4,5-tetrahydroxypentane; 2-(hydroxymethyl)-l,3,4-trihydroxybutane; and l,2,3,4,S-pentahydroxypentane.
- a presently preferred group of polyhydroxy alcohols are: glycerol; 1,2,3-trihydroxybutane; 1,2,4-trihydroxybutane; and erythritol.
- Glycerol is the presently most preferred polyhydroxy alcohol.
- the combination of the glycol ether and the saturated acyclic polyhydric alcohol is present in the hydrocarbon fuel in the range of 0.01 to 1.0 volume percent based on fuel, preferably 0.01 to 0.5, more preferably 0.05 to 0.2 volume percent.
- the ratio of the alcohol to the ether is such that there is present 0.4 to 49 volume percent alcohol and 99.6 to 51 volume percent ether, preferably 0.5 to 40 volume percent alcohol and 99.5 to 60 volume percent ether, even more preferably 0.7 to volume percent alcohol and 99.3 to 90 volume percent ether.
- a preferred combination useful as an additive to a hydrocarbon fuel is methyl Cellosolve, glycerol and stearamidopropyldimethyl(beta-hydroxyethyl)ammonium nitrate.
- the components of the additive may be added to the hydrocarbon fuel in broad ranges of concentration.
- the nitrogenous compound is persent in an amount win the range of 0.05 to 500 weight parts per million based on fuel, preferably 4 to 100 weight parts per million.
- the above components may be dispersed in the hydrocarbon fuel prior to injection into the storage tank, either individually or preblended as a compatible composition or added to the storage tank, so long as they are homogeneously dispersed or distributed throughout the hydrocarbon fuel.
- the additive is easily dispersed in the fuel in any conventional manner such as stirrer-equipped tanks, pipe line feed and the like.
- hydrocarbon fuels in which the additive of the invention may be employed include those boiling between about 75 and about 750 F., at one atmosphere pressure, particularly petroleum distillate fuels boiling in that range.
- Such fuels include gasolines, aviation turbojet fuels, kerosenes, diesel fuels and heating oils.
- Gasolines, as referred to herein, are mixtures of volatile hydrocarbons boiling between about 75 F. and about 450 F. as determined by ASTM D-86-56 and presently defined by ASTM Specification D-9 10-57-T and D-439-58T.
- Such gasolines frequently contain various beneficial additives such as antiknock agents, scavenging agents, antioxidants, dyes, anti-icing agents and solvent oils in total additive concentrates up to about 5 percent by weight.
- volatile hydrocarbons boiling in the range between about 100 F. and about 600 F. and are presently defined by US. Military Specifications MlL-J5624, MILF-25524 and MILF25558.
- Diesel fuels as referred to in connection with the invention in general, boil between about 250 F. and about 750 F. and are covered by ASTM Specification D-975-53T.
- Heating oils include both kerosenes and burning oils falling within Grades 1 and 2 of ASTM Specification D-396-48T.
- the additives of the invention are particularly useful in jet aviation fuels. They may, however, also be employed in solvent naphthas, transformer oils and other hydrocarbon oils boiling between about 75 F. and about 750 F.
- jet engine and jet engine fuel refer to and include turboprop, turbojet, ramjet and pulse jet engines and fuels designed to be used in said engines.
- the additive of this invention is particularly adaptable for operating a jet engine which encounters subfreezing temperatures, said engine being equipped with a fuel supply system subject to being obstructed by ice formation
- Aviation turbojet fuels comprise mixtures of a at subfreezing temperatures due to the presence of water in the fuel, said fuel supply system also being subject to static electricity accumulation due to the use of a hydrocarbon fuel of undesirable electrical conductivity characteristics.
- my invention resides in the step of passing a liquid hydrocarbon fuel through said fuel supply system to the combustion zone, said fuel containing the nitrogenous compound, glycol ether and polyhydroxyalcohol additive of this invention as hereinbefore described.
- the JP-4 fuel used in the following examples had the following physical properties:
- Example 8 Since the water separability data in Example I was Table 11 based on interfacial tension values, additional runs were made using an accepted device closely approaching the Run Nu PPM B 1 1 Interracm tension, actual conditions facing a fuel being used in a jet engine. dyHeS/cm- The data in Table IV was obtained using a Water Separorneter, Model 1104, Emcee Electronics, Inc., Clay- 28-3 mont, Delaware.
- the principle of the device is essentially that of full g8 g2 10 scale fuel handling equipment wherein jet fuel is pumped through a filter containing a fiberglass filter element which 1 See Example I coalesces the minute particles of water which may be dispersed in the fuel into larger droplets which are then data clearly demonstrate the operablhty of the capable of settling out and being removed from the fuel.
- glycol ether and the nitrogenous compound serve to substantially increase the probability that the Water may be removed from the hydrocarbon fuel by conventional filters and the like.
- An additive useful in a liquid hydrocarbon fuel said fuel having a boiling point in the range of about to about 750 F. and having a conductivity of l 10- to 1 l0 mho/cm., said additive consisting essentially of (1) from 20 to 2000 weight parts of a blend of (A) 99.6 to 51 volume percent of ethylene glycol monomethyl ether and (B) .4 to 49 volume percent of glycerol, and (2) one Weight part of stearamidopropyldirnethyl(betahydroxyethyl) ammonium nitrate.
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- 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)
- Liquid Carbonaceous Fuels (AREA)
Description
United States Patent O 3,230,058 ADDITIVE FOR HYDRGCARBON FUELS Harold C. Walters, Bartlesville, Okla, assignor to Phillips Petroleum Company, a corporation of Delaware No Drawing. Filed Nov. 20, 1961, Ser. No. 153,727 2 Claims. (Cl. 44-66).
This invention relates to an additive for hydrocarbon fuels. In one aspect the invention relates to a hydrocarbon fuel inhibited against static electricity accumulation. In another aspect the invention relates to a method of inhibiting ice formation and static electricity accumulation in volatile hydrocarbon fuels.
Continuing research in the utilization of hydrocarbon fuels as produced improvements in their performance, handling, safety aspects and, in some cases, has reduced the cost of operation. Many of these improvements have been in the form of additives wherein small quantitles of specific compositions are added to the fuel, such as bactericides, anticorrosion agents, deicers, heat stabilizers, storage stabilizers, combustion deposit modi fiers antiknock compounds, scavengers, etc.
Considerable attention has been focused in recent years upon the electrical conductivity properties of hydrocarbon fuels due to a number of explosions which have occurred during the handling of such fuels. Although most of these explosions have taken place while turbojet aircraft fuels were being transferred from one tank to another, there have been instances of explosions occurring while transporting gasolines, kerosenes, solvents and other hydrocarbon products boiling between about 75 and about 750 F. when the ambient temperatures were slightly above the flash points of the products. Turbojet fuels are particularly hazardous because their vapors form explosive mixtures with the air over a relatively wide temperature range.
It has been postulated that these explosions are due to tribo electric discharges. The mechanism involved in explosions of hydrocarbon fuels attributed to tribo electricity are not fully understood; however, it is believed that small concentrations of ionic contaminants play an important role. It has been postulated that ionizable particles in the fuels are attracted to surfaces, such as the sides of fuel tanks and pipe lines, where the movement of the fuel sweeps away some of the particles of opposite polarity thus tending to create an electrical charge on the fuel. Where such a potential reaches a sufliciently high level, electrical energy is discharged and may ignite hydrocarbon vapors present in admixture with air to cause an explosion. This is, of course, only one explanation of the phenomena and there may be other mechanisms involved.
It has been found that hydrocarbon fuels which are void of ionizable contaminants, such as residues, degradation or oxidation products, do not readily become charged. However, such an ultra clean fuel condition is difficult to achieve and maintain in the practical realm. However, it is known that polar materials may increase the conductivity of the fuel to a point where the charge may be safely conducted away. Thus, by adding ionizable materials to the fuel the ability of the fuel to dissipate static charges surpasses the ability to develop them. Such a fuel exhibits a relatively high conductivity and is less likely to cause difiiculty. It has been reported that a dangerous middle ground exists and that a fuel 3,230,058 Ce Patented Jan. 18, 1966 with an intermediate conductivity of IX i0 to 1X10- mho/cm. is capable of becoming dangerously charged. Consequently, a number antistatic additives have been developed which purport to increase the conductivity of fuel to l 10- or greater. Hydrocarbon fuels generally have electrical conductivity in the range of 1 1O- to 1 l() so that not all fuels are necessarily sulbject to turboelectric discharges. However, additives to fuels possessing dangerous conductivity have sometimes been known to degrade other properties of the fuel. Similarly, combinations of two or more additives may also produce unexpected and undesirable side effects. For example, an additive which successfully inhibits bacterial growth in fuel may cause metal corrosion problems and an anticorrosion agent may also adversely effect combustion deposits. In addition, although some additives do markedly increase the conductivity of hydrocarbons, it has been found that their usefulness generally is limited to a very narrow concentration range. If the concentration of such an additive in the fuel oil is inadvertently reduced, there may be a greater danger of explosion than if no additive were present at all.
An important property of a liquid hydrocarbon fuel which is frequently disturbed by the use of fuel additives is its ability to separate from water. Hydrocarbon fuels are frequently unavodably exposed to water or water vapor. Water is a very highly undesirable component in fuels, particularly when used in aircraft engines, for a host of reasons and, consequently, the fuel is passed through filters or water separators which dry the fuel when transferring the fuel from one point to another. The ability of the fuel to separate itself from water determines the efliciency of the water separation stage and is therefore an important fuel property. This property is disturbed when materials having surfactant properties are added to the fuel. Such additives tend to emulsify the water and to prevent its removal by the equipment utilized.
The formation of ice within the fuel system of a jet aircraft has been recognized as a problem for a long time. Flights at high altitudes for long durations often result in the fuel being chilled to temperatures approaching that of the air in which the aircraft are operating. All jet fuel contains small amounts of dissolved and/or entrained water. When the fuel is chilled, the water separates from the fuel and ice is formed. Ice formation in an aircraft fuel system at points of restricted flow such as filters, screens, valves, orifices, etc., is a serious matter because the engine fuel supply may be restricted and certain instruments may not respond correctly. A number of engine flame-outs have been attributed to ice formation in the fuel system.
An anti-icing additive is described in the copending application of James A. Shotton, Serial No. 90,953, filed February 23, 1961, which is a continuation in part of Serial No. 79 filed January 4, 1960. Both applications of James A. Shotton are now abandoned. The additive described therein includes a blend of a saturated acyclic polyhydric alcohol and a glycol ether.
It is an object of this invention to provide a novel additive for hydrocarbon fuels.
It is another object of the invention to provide a novel hydrocarbon fuel composition having improved antistatic properties.
Another object of the invention is to provide a novel method of operating a jet engine with a fuel supply system subject to subfreezing temperatures and static electricity accumulation.
Yet another object of the invention is to provide an improved method of stabilizing a hydrocarbon fuel against ice formation and static electricity accumulation without adversely effecting water separability properties.
These objects are broadly accomplished by a liquid hydrocarbon fuel containing a nitrogenous compound having the formula wherein R is a member of the group consisting of aliphatic and alicyclic hydrocarbon radicals containing at least 7 carbon atoms per molecule, preferably 10 to 20 carbon atoms; R is a member of the group consisting of alkyl and hydroxyal'kyl radicals containing from 1 to 3 carbon atoms, inclusive; R is a member of a group consisting of hydrogen and radicals having the same meaning as R R is a hydroxyalkyl radical containing from 1 to 3 carbon atoms, inclusive; and Y is an anion.
In one aspect, a glycol ether is employed in conjunction with said nitrogenous compound.
In a preferred embodiment, the additive of this invention comprises said nitrogenous compound, a glycol ether and a saturated acyclic polyhydroxy alcohol as hereinafter defined.
A wide variety of monocarboxylic acids may supply R, such as, for example, caprylic acid, decenoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, oleic acid and other highly unsaturated fatty acids of 14 to 18 carbons obtained from vegetable and animal oil and fats such as soy'a bean oil, cotton seed oil, coconut oil, linseed oil, castor oil, dehydrated castor oil and the like, or from other sources such as tall oil. A-licyclic monocanboxylic acids which may be used include petroleum naphthenic acids of 7 to 14 carbon atoms having boiling points within the range of 215 to 310 C., as described in Ellis, Chemistry of Petroleum Derivatives (1934), pages 1062-1085, abietic acid, and the like.
Illustrative examples of radicals represented by R in the aforesaid nitrogenous compound are normal and unbranched heptyl, octyl, octenyl, nonyl, nonenyl, decyl, decenyl, undecyl, undecenyl, tridecyl, tetradecyl, tetradecenyl, heptadecyl, heptadecenyl, octadecyl, octadecenyl, the residue of abietic acid and the like radicals. Illustrative examples of the radical represented by R and R are methyl, ethyl, propyl, isopropyl, hydroxyethyl, dihydroxyp-ropyl, trihydroxypropyl and the like radicals. Illustrative examples of R include hydroxymethy-l, hydroxyethyl, hydroxypropyl, dihydroxypropyl, and the like radicals. Illustrative examples of anions represented by Y are chloride, bromide, fluoride, iodide, sulfate, sulfonate, phosphate, hydroxide, borate, carbonate, hydrocarbonate, isocyanate, nitrate, nitrite, oxalate, acetate, hydrogen sulfate, thiocyanate, sulfite, bisulfi-te, silicate, sulfide, ethylsulfate, and other inorganic and organic ions.
Representative nitrogenous compounds include:
r 11 0 ONEXCH 3-III-CH2CH5OHIHC1" Gainma caprylamidopropyldimethyl beta-hydroxyethyl) ammonium chloride Gamma-stearamidopropyldimethyl (2,3-dihydr0xypropyl) ammonium hydroxide [01 1511 0 ONH (CH 3-N(CH2OH2OH) ]+C O Gamma-s tearamidopropyl-tris (beta-hydroxyethyl) ammonium carbonate Gamma-stearamidopropyldimethyl (beta-hydroxyethyl) ammonium nitrate Gammadauramidopropylmethyl-bis (beta-hydroxyethyl) d ammonium chloride an CH3 Gamma-abietamidopropyldimethyl (beta-hydroxyethyl) ammonium iodide The preferred nitrogenous compound is gamma-steam amid oprop yldimethyl (be ta-hydroxy) ammonium nitrate.
It has been found that a combination of the above-recited nitrogenous compound, a saturated acyclic polyhydroxy alcohol and a glycol ether provides a particularly effective combination for inhibiting the accumulation of static electricity and the formation of ice in the fuel. Moreover, and most important, the effect of this specific combination of compounds on the accumulation of static electricity in the fuel is an improvement over the effect one Would expect based upon the effect exhibited by each individual compound in the fuel. This synergistic effect is also exhibited with regard to water separability.
Therefore, in one aspect of the invention the accumulation of static electricity and ice formation is inhibited by the inclusion of an additive comprising: (1) a blend of (A) a major proportion of a glycol ether having the formula R'(OCH 0H OH, where R is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, and tolyl groups, when R is hydrogen, x is 2 to 4, otherwise, x is 1 to 4, and (B) a minor amount of a saturated acyclic polyhydroxy alcohol having 3 to 5 carbon atoms per molecule, from 2 to 5 OH groups each attached to a different carbon and a ratio of hydroxy radicals to carbons in the range of 0.66:1 to 1: 1, said minor amount being sufficient to synergistically increase the antiicing properties of said blend when added to said hydrocarbon fuel; and (2) said hereinbefore-described nitrogenous compound, said nitrogenous compound being present in an amount suflicient to synergistically increase the electrical conductivity of said additive When added to said hydrocarbon fuel to a value sufficient to prevent a substant-ial amount of static electricity accumulation.
Suitable examples of glycol ethers which are employable in the additive of this invention include, among others, the following: methyl ether of ethylene glycol (methyl Cellosolve); ethyl ether of ethylene glycol (ethyl Cellosolve); butyl ether of ethylene glycol (butyl Cellosolve); methyl ether of diethylene glycol (methyl carbitol); ethyl ether of diethylene glycol (ethyl carbitod); butyl ether of dieth ylene glycol (butyl carbitol); methyl ether of triethylene glycol; ethyl ether of triethylene glycol; phenyl ether of ethylene glycol; tolyl ether of ethylene glycol; phenyl ether of triethylene glycol; tolyl ether of triethylene glycol; diethylene glycol; triethylene glycol; and tetraethylene glycol.
A presently preferred group of glycol ethers suitable for use in the practice of the invention are those having the formula R(OCH CH OH wherein: R is selected from the group consisting of methyl, ethyl, propyl, and butyl groups, and x is an integer of fro-m 1 to 4. The most preferred glycol ethers are those of the above formula wherein R is methyl or ethyl and x is 1 or 2.
Suitable examples of saturated acyclic polyhydroxy alcohols include the following: 1,2-dihydroxypropane; 1,3- dihydroxypropane; glycerol; 1,2,3-trihydroxybutane; 1,2, 4 trihydroxybutane; 2 (hydroxymethyl)-1,3-dihydroxypropane; erythritol; pentaerythritol; l,2,3,4-tetrahydroxy pentane; 1,2,3,5 tetrahydroxypentane; l,2,4,5-tetrahydroxypentane; 2-(hydroxymethyl)-l,3,4-trihydroxybutane; and l,2,3,4,S-pentahydroxypentane.
A presently preferred group of polyhydroxy alcohols are: glycerol; 1,2,3-trihydroxybutane; 1,2,4-trihydroxybutane; and erythritol. Glycerol is the presently most preferred polyhydroxy alcohol.
In general, the combination of the glycol ether and the saturated acyclic polyhydric alcohol is present in the hydrocarbon fuel in the range of 0.01 to 1.0 volume percent based on fuel, preferably 0.01 to 0.5, more preferably 0.05 to 0.2 volume percent. In addition the ratio of the alcohol to the ether is such that there is present 0.4 to 49 volume percent alcohol and 99.6 to 51 volume percent ether, preferably 0.5 to 40 volume percent alcohol and 99.5 to 60 volume percent ether, even more preferably 0.7 to volume percent alcohol and 99.3 to 90 volume percent ether.
A preferred combination useful as an additive to a hydrocarbon fuel is methyl Cellosolve, glycerol and stearamidopropyldimethyl(beta-hydroxyethyl)ammonium nitrate.
The components of the additive may be added to the hydrocarbon fuel in broad ranges of concentration. Preferably, the nitrogenous compound is persent in an amount win the range of 0.05 to 500 weight parts per million based on fuel, preferably 4 to 100 weight parts per million.
The above components may be dispersed in the hydrocarbon fuel prior to injection into the storage tank, either individually or preblended as a compatible composition or added to the storage tank, so long as they are homogeneously dispersed or distributed throughout the hydrocarbon fuel. The additive is easily dispersed in the fuel in any conventional manner such as stirrer-equipped tanks, pipe line feed and the like.
Any suitable type of hydrocarbon fuel can be employed in the practice of the invention. The hydrocarbon fuels in which the additive of the invention may be employed include those boiling between about 75 and about 750 F., at one atmosphere pressure, particularly petroleum distillate fuels boiling in that range. Such fuels include gasolines, aviation turbojet fuels, kerosenes, diesel fuels and heating oils. Gasolines, as referred to herein, are mixtures of volatile hydrocarbons boiling between about 75 F. and about 450 F. as determined by ASTM D-86-56 and presently defined by ASTM Specification D-9 10-57-T and D-439-58T. Such gasolines frequently contain various beneficial additives such as antiknock agents, scavenging agents, antioxidants, dyes, anti-icing agents and solvent oils in total additive concentrates up to about 5 percent by weight. volatile hydrocarbons boiling in the range between about 100 F. and about 600 F. and are presently defined by US. Military Specifications MlL-J5624, MILF-25524 and MILF25558. Diesel fuels, as referred to in connection with the invention in general, boil between about 250 F. and about 750 F. and are covered by ASTM Specification D-975-53T. Heating oils, as the term is used herein, include both kerosenes and burning oils falling within Grades 1 and 2 of ASTM Specification D-396-48T. As pointed out hereinbefore, the additives of the invention are particularly useful in jet aviation fuels. They may, however, also be employed in solvent naphthas, transformer oils and other hydrocarbon oils boiling between about 75 F. and about 750 F.
Thus, while the invention has been described with reference to jet engine fuels, e.g. JP-3, JP-4 and JP-S, the invention is not so limited. As used herein, the terms jet engine and jet engine fuel refer to and include turboprop, turbojet, ramjet and pulse jet engines and fuels designed to be used in said engines.
The additive of this invention is particularly adaptable for operating a jet engine which encounters subfreezing temperatures, said engine being equipped with a fuel supply system subject to being obstructed by ice formation Aviation turbojet fuels comprise mixtures of a at subfreezing temperatures due to the presence of water in the fuel, said fuel supply system also being subject to static electricity accumulation due to the use of a hydrocarbon fuel of undesirable electrical conductivity characteristics. In such use my invention resides in the step of passing a liquid hydrocarbon fuel through said fuel supply system to the combustion zone, said fuel containing the nitrogenous compound, glycol ether and polyhydroxyalcohol additive of this invention as hereinbefore described.
The invention will now be illustrated by the following specific embodiments.
The JP-4 fuel used in the following examples had the following physical properties:
Reid vapor pressure 2. 9 A.P.I. 56. 4 Distillation F.) I.B.P. 125 60 326 5 169 340 40 2B0 Rec 99 5O 304 Res I Said fuel complied fully with all other specifications for a JP-4 jet fuel, including the freezing point specification maximum of 76 F. As is known to those skilled in the art, this freezing point specification is provided to insure that plugging of the fuel system will not occur due to freezing of the fuel itself at the low temperatures existing at the high altitudes at which jet aircraft operate.
EXAMPLE I Interfacial tension, dynes/cm.
Fuel additive Commercial antistatic agent O," 80 ppm. A +G" (80 ppm.) Commercial additive D, 80 ppm. A |-D (S0 p.p.m.)
1 0.10 volume percent based on fuel of a mixture of 90 parts by volume of methyl Cellosolve and 10 parts by volume of glycerol.
The data in the preceding Table I demonstrate the synergistic effect of the stearamidopropyldimethyl(beta-hydroxyethyl)ammonium nitrate and the preferred anti-icing agent which comprises methyl Cellosolve and glycerol. It is obvious that the components coact so as to produce an interfacial tension in the fuel which is substantially higher than that obtainable with the stearamidopropyldimethyl (beta-hydroxyethyl)ammonium nitrate by itself. This is most surprising since one would expect the interfacial tension of the fuel containing the combined additives to be decreased by an amount which is approximately the sum of the decrease due to the stearamidopropyldimethyl(betahydroxyethynammoniurn nitrate and the decrease due to the anti-icing agent when used individually. It is to be noted that no such coaction with the anti-icing agent exists with the two control additives.
EXAMPLE II Runs were made to determine the effect of the concentration of stearamidopropyldimethyl(beta-hydroxyethyl) ammonium nitrate on the interfacial tension values, determined as described in Example I.
8 EXAMPLE 1v Since the water separability data in Example I was Table 11 based on interfacial tension values, additional runs were made using an accepted device closely approaching the Run Nu PPM B 1 1 Interracm tension, actual conditions facing a fuel being used in a jet engine. dyHeS/cm- The data in Table IV was obtained using a Water Separorneter, Model 1104, Emcee Electronics, Inc., Clay- 28-3 mont, Delaware. 4 1 The principle of the device is essentially that of full g8 g2 10 scale fuel handling equipment wherein jet fuel is pumped through a filter containing a fiberglass filter element which 1 See Example I coalesces the minute particles of water which may be dispersed in the fuel into larger droplets which are then data clearly demonstrate the operablhty of the capable of settling out and being removed from the fuel. Composltlon Over a Wlde range- Two liters of JP-4 hydrocarbon jet fuel were emulsi- EXAMPLE 111 fited wilth mll. offiwater at 75 t? 85 F. and pumped t roug a erg ass ter at rates 0 30 40 50 70 90 The electrical conductivity of a hydrocarbon fuel JP-4, 1 1 containing different additives was determined 1n order to 331 g 23 ;223:12 r fi fiiif gg g 3 2 1 demonstrate the effectiveness of the preferred composi- 20 tered fual is measurd by a photocell pThus i effect of fion of the invention with regard to its ability to prevent the additive on the separability of water from the fuel is iififigiifgfgg gg ggg gg gg ig giggz i i i i fi determined. One instrument reading is made on a 0 100 11'1110/ cm Electrical conductivity was determined on apscale of g resulting a rgadmgs are average to yie a va ue nown as ater eparagg suclias desfcrs'liaeq l f p f i i g g 25 tion Index. Fuel compositions yielding high numerical ta t g E Ions S 5:??? 6 r0 eum t 5 g values are therefore superior to fuels yielding low numeri g g fg g g gg 1 in gfi z g g fi z i ical values from the standpoint of water separability. ber 12, 1957. Table IV Table I Run Fuel additive Water sepaia No. tion index .Run Fuel additives Specific con- N o. ductivlty, 1 None 100 mho/cm. 2 A1, anti-icing agent 2 100 35 3 B, stearamidopropyldimethyl (betahydroxy- 2 67. 2 Nmw 2 lxlo 4 Aethygalnonmni nitrate, 20 p.p.m. 2 99 5 A anti-ieing agent .III 2 1 10 511:1: oenlneremi 'ri tis ieiietiht'"(B 165515. 1: 6418 Commercial antistatic agent C 40 p.p.m-.-- 0.92 10- 6 A1 3" 40 p p m) 2 62 5 40 .m.+A 2.78X10'i3 I. B, 4 p.p.m.-l-A 4.73 10 40 3 Average of 4 13 16 ppm 3 OOX1O 1U Amount recommended by manufacturer. 16 1021mm) It is to be noted that synergism of the anti-icing agent a f and stearamidopropyldimethyl(beta hydroxyethyDam- .2 E555 fg f fiilg runs. monium nitrate with respect to Water separability is again demonstrated. One would expect an additive effect so ff .2 to 3 'fi g a that the value would be 67.2 instead of 99.5 as obtained. amoun s o e S eemml Opropy y It is to be noted that this is the case with C when added 'droxyethyl)ammon1um nitrate added to the hydrocarbon to A (Run N0 6) fuel is sufficient to increase the conductivity to the desired EXAMPLE V level. It is further seen that a combination of the stear- .amidodi ropyldimethyl(beta-hydroxyethyl)ammonium ni- The synergistic eifectof a mixture of methyl Cellosolve trate and the preferred anti-icing agent is also satisfactory. and steafainldopfopyldlmetllyl(beta y y y l In addition, the ombination of the stearamidodipropyldini m filtrate Was investigated as to specific conducmethyl(beta-hydroxyethyl)ammonium nitrate and the tivity and water separability. The following data were anti-icing agent display conductivities which are greater Obtained on JP-4 jet fuel in the same manner as hereinthan one would expect from the effect each gave indibefore described in Example III.
Table V Run Fuel additive Specific conductivity, Water separation index No. mho/cm.
1 None 6.94 10 (Av. 0i3runs). 100. 2 0.1 vol. percent methyl Cellosolve 1.s5 10- (Av. 0f 2runs). 100 (Av. of 2 runs). 3 20 stiegramidopropyldirrethyl (beta- 2.08X10-11 (Av. of 2runs) 67.2 (Av. of 4 runs). 4 0.1ol $enrhilfle3ljdb27fiib p.p.m. 4.77 10- (Av. of 2rur1s) 81.0 (Av. of 2runs).
il fifiefififihfifiud nitrate).
It will be noted that this specimen varies slightly in conductivity from another specimen of the same fuel used in Example III. This variance is believed due to lack of instrument sensitivity at this low level of con ductivity.
vidually. Thus, there is a synergistic effect for the antiicing agent and the stearamidodipropyldimethyl (beta-hydroxyethyl)ammonium nitrate with respect to conductivity as well as water separation,
fuel.
It will be seen from the above data that the addition of methyl Cellosolve by itself to the hydrocarbon fuel does not substantially improve the specific conductivity of the Although the addition of the nitrogenous cornpound does improve the anti-static properties of the fuel to Within an acceptable range, it is to be noted from Run No. 4 that the combination of methyl Cellosolve and the stearamidopropyldimethyl (beta-hydroxyethyl) ammonium nitrate more than doubles the specific conductivity of the run without the methyl Cellosolve.
It is also to be noted that the combination of the glycol ether and the nitrogenous compound serve to substantially increase the probability that the Water may be removed from the hydrocarbon fuel by conventional filters and the like.
While certain examples, structures, compositions and process steps have been described for purposes of illustration the invention is not limited to these. Variation and modification within the scope of the disclosure and the claims can readily be eifected by those skilled in the art.
I claim:
1. A liquid hydrocarbon fuel having a boiling point in the range of about 75 to about 750 F. and having a conductivity of 1x to 1 10 mho/cm. containing an additive consisting essentially of (1) from 0.01 to 1.0 volume percent based on fuel of a blend of (A) 99.6 to 51 volume percent of ethylene glycol monomethyl ether, and (B) 0.4 to 49 volume percent of glycerol and (2) 10 from 0.05 to 500 weight parts .per million parts of fuel of stearamidopropyldimethyl(beta-hydroxyethyl ammonium nitrate, said (2) being present in said fuel in an amount sufiicient to synergistically increase the electrical conduc tivity of said fuel to at least 1 l0 mho/ cm.
2. An additive useful in a liquid hydrocarbon fuel, said fuel having a boiling point in the range of about to about 750 F. and having a conductivity of l 10- to 1 l0 mho/cm., said additive consisting essentially of (1) from 20 to 2000 weight parts of a blend of (A) 99.6 to 51 volume percent of ethylene glycol monomethyl ether and (B) .4 to 49 volume percent of glycerol, and (2) one Weight part of stearamidopropyldirnethyl(betahydroxyethyl) ammonium nitrate.
References Cited by the Examiner UNITED STATES PATENTS 2,589,674 3/1952 Cook et al 252-8.8 X 2,626,876 1/1953 Carnes 2528,75 X 2,901,430 8/1959 Chiddix et al. 44-66 X 3,027,246 3/1962 Bartlett 44-66 3,032,971 5/1962 Shotton 4477 X 3,048,539 8/1962 Kocay et al 2528.8
DANIEL E. WYMAN, Primary Examiner.
Claims (1)
1. A LIQUID HYDROCARBON FUEL HAVING A BOILNG POINT IN THE RANGE OF ABOUT 75 TO ABOUT 750*F. AND HAVING A CONDUCTIVITY OF 1X10**-12 TO 1X10**-15MHO/CM. CONTAINING AN ADDITIVE CONSISTING ESSENTIALLY OF (1) FROM 0.01 TO 1.0 VOLUME PERCENT BASED ON FUEL OF A BLEND OF (A) 99.6 TO 51 VOLUME PERCENT OF EHTYLENE GLYCOL MONOMETHYL ETHER, AND (B) 0.4 TO 49 VOLUME PERCENT OF GLYCEROL AND (2) FROM 0.05 TO 500 WEIGHT PLARTS PER MILLION PARTS OF FUEL OF STEARAMIDOPROPYLDIMETHYL(BETA-HYDROXYETHYL) AMMONIUM NITRATE, SAID (2) BEING PRESENT IN SAID FUEL IN AN AMOUNT SUFFICIENT TO SYNERGISTICALLY INCREASE THE ELECTRICAL CONDUCTIVITY OF SAID FUEL TO AT LEAST 1X10**-11MHO/CM.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US153727A US3230058A (en) | 1961-11-20 | 1961-11-20 | Additive for hydrocarbon fuels |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US153727A US3230058A (en) | 1961-11-20 | 1961-11-20 | Additive for hydrocarbon fuels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3230058A true US3230058A (en) | 1966-01-18 |
Family
ID=22548478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US153727A Expired - Lifetime US3230058A (en) | 1961-11-20 | 1961-11-20 | Additive for hydrocarbon fuels |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3230058A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4624633A (en) * | 1985-01-09 | 1986-11-25 | Mtc-Choice, Inc. | High percentage glycol fuel and burner |
| WO2002074729A2 (en) * | 2001-03-20 | 2002-09-26 | Cognis Ibéria S.L. | Quaternary surfactants |
| WO2009108310A1 (en) * | 2008-02-25 | 2009-09-03 | Exxonmobil Research And Engineering Company | Method for determining the filterability of jet fuel containing additive(s) and conditions for the delivery of acceptable water content fuel |
| US20190330549A1 (en) * | 2016-10-21 | 2019-10-31 | Total Marketing Services | Combination of fuel additives |
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| US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
| US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
| US2901430A (en) * | 1953-11-06 | 1959-08-25 | Gen Aniline & Film Corp | Corrosion inhibition |
| US3027246A (en) * | 1958-11-03 | 1962-03-27 | Du Pont | Liquid hydrocarbon distillate fuels containing hydrocarbon-soluble betaines as antistatic agents |
| US3032971A (en) * | 1961-10-20 | 1962-05-08 | Phillips Petroleum Co | Mixtures of acyclic polyhydroxy alcohols and glycol ethers as anti-icing additives for hydrocarbon fuels |
| US3048539A (en) * | 1959-06-29 | 1962-08-07 | American Cyanamid Co | Antistatic textile lubricant finishes |
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|---|---|---|---|---|
| US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
| US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
| US2901430A (en) * | 1953-11-06 | 1959-08-25 | Gen Aniline & Film Corp | Corrosion inhibition |
| US3027246A (en) * | 1958-11-03 | 1962-03-27 | Du Pont | Liquid hydrocarbon distillate fuels containing hydrocarbon-soluble betaines as antistatic agents |
| US3048539A (en) * | 1959-06-29 | 1962-08-07 | American Cyanamid Co | Antistatic textile lubricant finishes |
| US3032971A (en) * | 1961-10-20 | 1962-05-08 | Phillips Petroleum Co | Mixtures of acyclic polyhydroxy alcohols and glycol ethers as anti-icing additives for hydrocarbon fuels |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4624633A (en) * | 1985-01-09 | 1986-11-25 | Mtc-Choice, Inc. | High percentage glycol fuel and burner |
| WO2002074729A2 (en) * | 2001-03-20 | 2002-09-26 | Cognis Ibéria S.L. | Quaternary surfactants |
| WO2002074729A3 (en) * | 2001-03-20 | 2003-10-02 | Cognis Iberia Sl | Quaternary surfactants |
| US20040102355A1 (en) * | 2001-03-20 | 2004-05-27 | Joaquin Bigorra Llosas | Quaternary surfactants |
| WO2009108310A1 (en) * | 2008-02-25 | 2009-09-03 | Exxonmobil Research And Engineering Company | Method for determining the filterability of jet fuel containing additive(s) and conditions for the delivery of acceptable water content fuel |
| US20090289013A1 (en) * | 2008-02-25 | 2009-11-26 | Exxonmobil Research And Engineering Company | Method for determining the filterability of jet fuel containing additive(s) and conditions for the delivery of acceptable water content fuel |
| US8017020B2 (en) | 2008-02-25 | 2011-09-13 | Exxonmobil Research And Engineering Company | Method for determining the filterability of jet fuel containing additive(s) and conditions for the delivery of acceptable water content fuel |
| US20190330549A1 (en) * | 2016-10-21 | 2019-10-31 | Total Marketing Services | Combination of fuel additives |
| US10767126B2 (en) * | 2016-10-21 | 2020-09-08 | Total Marketing Services | Combination of fuel additives |
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