MXPA98000903A - Liquid polifunctional additives for improved lubrication of combusti - Google Patents
Liquid polifunctional additives for improved lubrication of combustiInfo
- Publication number
- MXPA98000903A MXPA98000903A MXPA/A/1998/000903A MX9800903A MXPA98000903A MX PA98000903 A MXPA98000903 A MX PA98000903A MX 9800903 A MX9800903 A MX 9800903A MX PA98000903 A MXPA98000903 A MX PA98000903A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- formula
- hydrogen
- compound
- phenyl
- Prior art date
Links
- 239000000654 additive Substances 0.000 title description 18
- 239000007788 liquid Substances 0.000 title description 5
- 238000005461 lubrication Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 239000000446 fuel Substances 0.000 claims abstract description 82
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims abstract description 65
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 42
- 239000011593 sulfur Substances 0.000 claims abstract description 42
- 239000003921 oil Substances 0.000 claims abstract description 37
- 235000019198 oils Nutrition 0.000 claims abstract description 37
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 34
- 235000019486 Sunflower oil Nutrition 0.000 claims abstract description 30
- 239000002600 sunflower oil Substances 0.000 claims abstract description 30
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-Butanediol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 14
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N Triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 240000007170 Cocos nucifera Species 0.000 claims abstract description 12
- 235000013162 Cocos nucifera Nutrition 0.000 claims abstract description 12
- 238000007792 addition Methods 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 238000005260 corrosion Methods 0.000 claims abstract description 4
- 230000001105 regulatory Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- -1 3- (3 ', 5' -di methyl-4-methyl-4 '-hydroxyphenyl) -propionate Chemical compound 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 76
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 150000002402 hexoses Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 239000002283 diesel fuel Substances 0.000 claims description 13
- 235000019197 fats Nutrition 0.000 claims description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 13
- 239000003240 coconut oil Substances 0.000 claims description 12
- 235000019864 coconut oil Nutrition 0.000 claims description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (-)-propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 9
- 229960004063 Propylene glycol Drugs 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 235000013772 propylene glycol Nutrition 0.000 claims description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 8
- YODZTKMDCQEPHD-UHFFFAOYSA-N Thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 235000011293 Brassica napus Nutrition 0.000 claims description 6
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 5
- 235000005822 corn Nutrition 0.000 claims description 5
- 235000005824 corn Nutrition 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000004006 olive oil Substances 0.000 claims description 5
- 235000008390 olive oil Nutrition 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 235000019483 Peanut oil Nutrition 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000000312 peanut oil Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 235000005713 safflower oil Nutrition 0.000 claims description 3
- 239000003813 safflower oil Substances 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 239000000047 product Substances 0.000 description 57
- 150000003254 radicals Chemical class 0.000 description 43
- 238000000034 method Methods 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 28
- 235000011187 glycerol Nutrition 0.000 description 21
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical group CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000003925 fat Substances 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 229960001735 pentaerythritol Drugs 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- VSGNNIFQASZAOI-UHFFFAOYSA-L Calcium acetate Chemical group [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 230000000111 anti-oxidant Effects 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000001639 calcium acetate Substances 0.000 description 6
- 235000011092 calcium acetate Nutrition 0.000 description 6
- 229960005147 calcium acetate Drugs 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 240000008100 Brassica rapa Species 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-Dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N CC(CCCCC(O)O)(C)C Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- 229940017219 METHYL PROPIONATE Drugs 0.000 description 4
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N N,N'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229940093476 ethylene glycol Drugs 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N nonane-1,9-diol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004707 phenolate Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- HMFKFHLTUCJZJO-UHFFFAOYSA-N 2-{2-[3,4-bis(2-hydroxyethoxy)oxolan-2-yl]-2-(2-hydroxyethoxy)ethoxy}ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCC(OCCO)C1OCC(OCCO)C1OCCO HMFKFHLTUCJZJO-UHFFFAOYSA-N 0.000 description 2
- 241001136782 Alca Species 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M Caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M Rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical class OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 2
- NWGKJDSIEKMTRX-HSACVWGTSA-N [(2R)-2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (E)-octadec-9-enoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-HSACVWGTSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000010771 distillate fuel oil Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical group 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- DVOOWDFPPNOBFV-UHFFFAOYSA-N (3E)-penta-1,3-diene Chemical group C=C[CH]C=C DVOOWDFPPNOBFV-UHFFFAOYSA-N 0.000 description 1
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N 1,3-Diaminopropane Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- STEYNUVPFMIUOY-UHFFFAOYSA-N 1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 description 1
- KPWQXRCOAIRWLP-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(O)C(N)=C1 KPWQXRCOAIRWLP-UHFFFAOYSA-N 0.000 description 1
- BBRHQNMMUUMVDE-UHFFFAOYSA-N 1-N,2-N-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1 BBRHQNMMUUMVDE-UHFFFAOYSA-N 0.000 description 1
- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-N,4-N-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 1
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-N,4-N-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical class OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-L thiophosphate(2-) Chemical compound OP([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-L 0.000 description 1
- 150000003918 triazines Chemical class 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
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
- SMVBWTKCDCPTQG-UHFFFAOYSA-N tris[2-(7-methyloctyl)phenoxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CCCCCCC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)CCCCCCC(C)C)OC1=CC=CC=C1CCCCCCC(C)C SMVBWTKCDCPTQG-UHFFFAOYSA-N 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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
Abstract
The present invention relates to: The lubricity (anti-wear properties) of fuels is improved, for example, hydrocarbon oils, oxygenated fuels or mixtures thereof, particularly diesel or aviation fuels, which have a reduced sulfur content and / or aromatics, to comply with the regulatory requirements, by the addition of at least one product, which can be obtained by the reaction of components a), b) and c), wherein component a) is a compound of formula I or a mixture of compounds of the formula I, the component b) is a compound of the formula II or a mixture of compounds of the formula II, and the component c) is a compound of the formula III or a mixture of compounds of the formula III: in which the general symbols are as defined in claim 1, the compound of formula I is, for example, pentaerythritol tiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol , d ietanolamine or glycerol, the compound of formula II is, for example, sunflower oil or coconut fat, and the compound of formula III is, for example, 3- (3 ', 5'-di-tert. -butyl-4'-hydroxyphenyl) -propianat or methyl. The aforementioned products also improve the inhibition of corrosion
Description
LIQUID POLYFUNTIONAL ADDITIVES FOR IMPROVED LUBRICATION OF FUEL
The present invention relates to anti-wear fuel compositions, which comprise a fuel, preferably a diesel fuel and other fuels having lower sulfur and / or aromatic contents, a liquid polyfunctional additive, and the use of this liquid polyfunctional additive. as an antiwear agent and an agent that improves lubricity for a motor fuel system. The Government of the United States of America has ordered a reduction in the sulfur and aromatics content of commercial diesel fuels. Regulatory agencies in other countries have already introduced such a requirement or consider doing so. This regulatory regime causes a problem because the fuel industry recognizes that fuels that comply with this regulation will exhibit reduced lubricity. The refining processes necessary to produce these fuels require a more severe hydrotreatment, which removes the polar species from the fuel and reduces its lubricity. Lubricity is a measure of the ability of the fuel to flow through the engine without causing excessive wear. Even marginal changes in lubricity can be significant in increasing wear on fuel pumps, valves and injector nozzles over an extended period of use.
Patent WO 96/16143 discloses that specific phosphorus esters improve the lubricity (anti-wear properties) of hydrocarbon fuels, oxygenated fuels or mixtures thereof, particularly diesel or aviation fuels, which have a reduced sulfur content and / or aromatics.
EP-A-0 565 487, which is related to the U.S. patent. 5,478,875, discloses antioxidants as stabilizers for polymers and lubricants.
Surprisingly, it has been found that these antioxidants also have lubricity against wear, which improves and has corrosion inhibiting properties in fuels having better sulfur and / or aromatic contents.
Accordingly, the present invention relates to a fuel composition against wear, which comprises: a) a fuel and ß) at least one product, which can be obtained by reaction of components a), b) and c) wherein component a) is a compound of formula I or a mixture of compounds of formula I, component b) is a compound of formula II or a mixture of compounds of formula II and component c) is a compound of formula III or a mixture of compounds of formula III,
X (Y) a
(I) (ni) (ID
wherein, in the compound of formula I, the radicals Y, independently of each other, are OH
(HOCH2CH2) N- or -HNR; L and the radicals R1 are hydrogen,
I rent
C3-C6 alkenyl, C7-C9 phenylalkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A] _, these radicals A ^, independently of each other, are C? -C? alkyl? , halogen, hydroxyl, methoxy or ethoxy, where
R 2 is hydrogen, C 1 -C 6 alkyl, 0 *, OH, NO, -CH 2 CN, C 1 -C 12 alkoxy C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl, C 7 -C 9 phenylalkyl, or C 7 -C 9 phenylalkyl, which is mono- di- or tri-substituted on the phenyl ring by C ^ C ^ alkyl or R2 is also acyl C ^ -Cg, or HOCH CH2-, it is already the number 1, 2, 3, 4 or 6, where,
If Y is OH and a is 1, X is alkyl ^ -045, C3-C18 alkenyl, -CH2CH2T? (CH2CH20) bR
or in which Ro has the
above definitions and \ Ti is oxygen, sulfur or .N-R5, / R4 is C ^ ^ alkyl, b is an integer varying from 0 to 10 and R5 is hydrogen, C ^ -Cl-Ci alkyl, or phenyl or
If Y is OH and a is 2, X is -CH2CH2T2 (CH2CH20) bCH2CH2-, where b has the above definitions, Rß -CH2CH2- N
O O -CH2-CH = CH-CH2- f-CH2CH2-NH-C-C-H-CH? CH2 or wherein
\? 7 T2 is oxygen, sulfur t NN - RR55 0o - - SS - CC - SS-- and R5 has the / 1 R «
above definitions, Rβ is hydrogen, C?-C18 alkyl, or phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 'independently of each other, are hydrogen, alkyl cl ~ 18 '° phenyl, or R7 and R8 together with the C atom to which they are attached, form a cycloalkyl ring C? ~ C12, or
if a is 3, X is C3-C10 alkanethyl, or N (CH2CH2-) 3, or
if Y is OH and a is 4, CH? - I 1 X is C4-C10-C3-alkyotetrayl, (-CH2-CH-CH2) 20, -CH2-CH-CH2-0-CH-CH2-,
, 0l1Je
Rg is C ^ -C4 alkyl,
if Y is OH and a is 6,
X is -CH
or C C-C alca alca alkanohexayl, ° /
if Y is HNRi and a is 1, X is alkyl ^ -CIQ, C3-C18 alkenyl, C5-C12 cycloalkyl, C7-C9 phenylalkyl, phenyl,
R2 is as defined before or
X is
or X together with R1 is a group of the formula -CH CH2CH CH2CH2- or -CH2CH2OCH2CH2-, wherein R10 is hydrogen or methyl and e is 2 or 3, or,
if Y is -HNR and a is 2, X is -CfH2f-, CH2CH2-, where
f is an integer that varies from 2 to 10 and g is an integer that varies from 1 to 6, and
in the compound of the formula II, the radicals Z are hydrogen or a group of the formula: O - (ChHhO C-Rn
k is an integer ranging from 0 to 6, where h is 2 or 3, i is an integer ranging from 0 to 12 and Rn is alkyl ^^ 30, C8-C30 alkenyl, C4-C2 cycloalkyl, phenyl or C7-C9 phenylalkyl, with the proviso that the O
II compound of formula II has a group - (C ^ H ^ O ^ -C-RI,;
in the compound of formula III, R12 is C2-C18 alkyl, C5-C2 cycloalkyl, phenyl or C7-C9 phenylalkyl,
wherein R ^ 5 is as defined above, m is an integer ranging from 0 to 3, R16 is alkyl Cj ^ -Cg, and n is an integer ranging from 1 to 6, where
if n is 1, R-L7 is hydrogen, C1-C45 alkyl, C5-C cycloalkyl? , C 2 -C 8 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol,
wherein R2 has the above definitions or furthermore R17 is CH2CH2- T -R 19 where T3 is oxygen, sulfur or N-R 22, /
Ri 9 is where R12 and R15
are as defined above, or R? g is also hydrogen, C C24 alkyl, phenyl, C5-C1 cycloalkyl or O -CH2-C-0-R25 'where p is an integer ranging from 2 to 4, q is a whole which varies from 2 to 20, R22 is alkyl ^ -C ^, phenyl or phenyl which is substituted by 1 to 3 radicals A] _, where the radicals A] _, independently of each other, are C1-C12 alkyl, halogen, hydroxyl, methoxy or ethoxy, or R22 is also C5-C8 cycloalkyl, R23 and R24 'independently of one another, are hydrogen or methyl, with the proviso that R23 and R24 are not simultaneously methyl-iote; R 4 is hydrogen or C 4 -C 24 alkyl, or
if n is 2, R-L7 is a divalent radical of a hexose, a radical
divalen
_CrH2r-, was defined before, -CH2CH2-T4-CH2CH2-, -CH2-CH = CH-CH2-, -CH2-C = C-CH2-,
wherein R18 and R20 'independently of each other, are hydrogen or C ^ -C ^ alkyl, or together are the radial -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10,
T is sulfur, where R7 and R8 have the above definitions and R26 is hydrogen, C alquilo-Cg alkyl / phenyl or phenyl which is substituted by 1 to 3 radicals A] _, where the radicals A ^ are as defined above in Formula I, or R2g is also C5-Cg cycloalkyl, or where R2 has the
previous definitions, or
if n is 3,
R ± -j is a trivalent radical of a hexose, a radical CH2CH -trivalent of a hexitol, I -CH2CH2-N-CH2CH2- '
-CH2 CH2-CH-CH3 I or -CH2-C-R27 5 CH, -CH-CHo-N-CH2-CH-CH3 where 3 2 2! -CH, R27 is hydrogen, CH2OH, C -C ^ alkyl, C? -C? Alkylamido, or
where Q, R ^ 2 and R ^ g have the above definitions, or
if n is 4,
R17 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol,
to the
if n is 5,
R17 is a pentavalent radical of a hexose or a pentavalent radical of a hexitol or
if n is 6, R17 is a hexavalent radical of a hexitol or
The alkyl, having no more than 45 carbon atoms, is a branched or unbranched radial, such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, secondary butyl, isobutyl, tertiary butyl, 2-ethylbutyl , n-pentyl, isopentyl, 1-methylpentyl, 1-3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n -octyl, 2-ethylhexyl, 1, 1,3-trimethylhexyl, 1,1,2,2-tetra ethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1, 1,2,2, 5, 5- hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, icosyl, docosyl or pentacosyl. One of the preferred meanings of lf R 4 and R 16 is, for example, C 1 -C 4 alkyl, of R 2 is methyl, of R 1L is C1-C alkyl, of R12 and R15 is C1-C4 alkyl, in particular tertiary butyl, and of R17 is C1-C4 alkyl. The cycloalkyl, which has no more than 12 carbon atoms, is, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl or cyclododecyl. One of the preferred meanings of Rlf R11 (R12 and R15 is C5-C7 cycloalkyl) Cyclohexyl is particularly preferred Alkenyl having no more than 30 carbon atoms is, for example, vinyl, propenyl, isopropenyl, 2-butenyl , 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodecenyl, oleyl, n-octadec -2-enyl or n-octadec-4-enyl If Rl 'R2 and x are C3-C6 alkenyl, then the carbon atom with which they bind to the nitrogen is advantageously saturated.Phenylalkyl, which has 7 to 9 carbon atoms. carbon is, for example, benzyl, α-methylbenzyl, α, α-dimethylbenzyl or phenylethyl, benzyl is preferred, Examples of phenyl, which is substituted by 1 to 3 radicals Ai are o-, m- or p- methylphenyl, 2,3-di-ethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 2-methyl -4-tert-butylphenyl, 2-ethylphenyl, 2,6-dimethylphenyl, 2,6 -diethyl-4-methylphenyl, 2,6-diisopropylphenyl, 4-tert-butylphenyl, p-nonylphenyl, o-m- or p-chlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2, 6-dichlorophenyl, 3,4-dichlorophenyl, 2,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, o-m- or p-hydroxyphenyl, o-, m- or p-methoxyphenyl, or- p-ethoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,5-diethoxyphenyl, o, m- or p-methoxycarbonyl, 2-chloro-6-methylphenyl, 3-chloro-2-methylphenyl, 3-chloro -4-methylphenyl, 4-chloro-2-methylphenyl, 5-chloro-2-methylphenyl, 2,6-dichloro-3-methylphenyl, 2-hydroxy-4-methylphenol, 3-hydroxy-4-methylphenyl, 2-methoxy -5-methylphenyl, 4-methoxy-2-methylphenyl, 3-chloro-4-methoxyphenyl, 3-chloro-6-ethoxyphenyl, 3-chloro-4,6-dimethoxyphenyl and 4-chloro-2,5-dimethoxyphenyl. Preferred is phenyl which is substituted by 1 or 2, in particular 1, radicals A_, where A ^ is, in particular, alkyl. The alkyl having 1 to 18 carbon atoms is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, tetradecyloxy, hexadecyloxy or octadecyloxy. One of the preferred meanings of R 2 is C 2 -C 2 alkoxy - Heptoxy and octoxy are particularly preferred. Cycloalkoxy having 5 to 12 carbon atoms is, for example, cyclopentoxy, cyclohexoxi, cycloheptoxy, cyclooctoxy, cyclodecyloxy or cyclododecyloxy. One of the preferred meanings of R2 is C5-C8-cialkoalkoxy. Cyclopentoxy and cyclohexoxi are particularly preferred. Examples of C7-C9 phenylalkyl, which is mono-, di- or tri-substituted on the phenyl ring by C -C4 alkyl, are methylbenzyl, dimethylbenzyl, trimethylbenzyl or tere. -butylbenzyl.
Acyl having 1 to 8 carbon atoms is, for example, formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, benzoyl, acryloyl or crotonyl, C alca ~ C8 alkanoyl, C3-C8 alkenoyl, or benzoyl, in particular, acetyl is preferred. The alkanetriyl having from 3 to 10 carbon atoms is, for example, | -CH2-CH-C -H 2-,. -CH.2-CHt2 - CH-CH, -.
-CH2-CH2-CH-CH2-CH2-, -CH2-CH2-CH-CH2-CH2-CH2- 0 -CH2-CH "CH2-CH-CH2-CH2-CH2-" Glyceryl is preferred.
The alkylethalyl having from 4 to 10 carbon-CH2 atoms is, for example. \ CH2-C-CH2- f _ ^ H2.¿H.H-CH2-, ~ CH2-CH2 - ¿HH - CHH - CCHH2 - C CHH22 --- CH2 - CH2 - CH - CH - CH2 -CH2-, _CH2-CH2-CH-CH2-? PHH-Cr.Ht-2-Cr.HH2- or > - GC: HH2 - C? HH2 - CGH - C? H - I2 - ^ CHL, 2-.CH? -. CHM --.C
Pentaerythrityl is preferred. The alkanohexyl having 6 to 10 carbon atoms 0 is, for example, -CH2-c? -CH-c? -H-CH2-,
-CH 2 -H-CH-CH 2 -H-CH-CH 2 - or -CH 2 -CH-CH-CH 2 -CH 2 -CH-CH-CH 2 -.
If R17, with n = 1 to 6 is an n-valent radical of a hexose, then this radical is derived, for example, from allose, altrose, glucose, mannose, gulose, iodine, galactose or talose, i.e. to obtain the corresponding compounds of formula III, one, two, three, four, five or six -OH groups must be replaced by the ester group El,
in which R? , R15 s and Q have the above definitions. For example, R- with n = 5, can be a group
Yes? is an n-valent radial of a hexitol, then the corresponding compounds of the formula III are obtained by replacing the -OH groups with the ester group E-1, mentioned above. R17, as a hexavalent radial of a hexitol, can be, for example.
This group is derived from D-sorbitol.
The alkylamido having 1 to 18 carbon atoms is, for example, CH3-CO-NH-, CH3CH2-CO-NH-, C6H13-CO-NH- or C18H37-CO-NH-.
means that the phenyl ring can be ortho-, meta- or para-substituted. The three components a), b) and c) can react with each other to give the products of the present invention in any desired sequence. Preferably, component a) is reacted first with component b), and component c) is then added. The reaction is advantageously carried out in the presence of a catalyst. Suitable catalysts are Lewis acids or bases. Examples of suitable basic catalysts are metal hydrides, metal alkylides, metal arylides, metal hydroxides, metal alcoholates, metal phenolates, metal amides or metal carboxylates. Examples of preferred metal hydrides are lithium hydride, sodium hydride or potassium hydride. Examples of preferred metal alkylides are butyl lithium or methyl lithium. An example of a preferred metal arylide is phenyllithium.
Examples of preferred metal hydroxides are lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide or aluminum hydroxide. Examples of preferred metal alcoholates are sodium methanolate, sodium ethanolate, potassium methanolate, ethanoia or potassium, sodium isopropylate or potassium tert-butylate. Examples of preferred metal phenolates are sodium phenolate or potassium phenolate. Examples of preferred metal amides are sodium amide or lithium amide. An example of a preferred metal carboxylate is calcium acetate. Examples of suitable Lewis acid catalysts
the radicals R30, R31, R32, R33, R34, R35, R36, R37, R38 and
R39 are, independently of each other, for example, alkyl or phenyl. Alkyl C] _-C] _g is preferred. A particularly preferred Lewis acid catalyst is dibutyl tin oxide.
The catalyst is added to components a), b) and c), for example, in an amount of 0.05 to 10 per thousand by weight, preferably in an amount of 0.1 to 5 per thousand by weight. An addition of 1 to 2 per thousand by weight of the dibutyltin oxide is particularly preferred. The components a), b) and e) can react in a solvent, for example xylene, or without a solvent. The reaction is preferably carried out without solvent. The reaction temperature is, for example, between 130 and 250SC. The reaction is preferably carried out at a temperature in the range of 130 to 1902C. A preferred process for the preparation of the component (ß) products comprises reacting components a), b) and c) in a molar quantitative ratio of 0.1: 1: 0.1 to 15: 1: 30 and is manifested in the EP-patent. A-0
565 487, which is related to the U.S. patent. 5,478,875. If components a), b) and c) are not commercially available, they can be prepared by known processes or analogously. Possible preparation processes for the compounds of formula III can be found, for example, in the following publications: patents GB-A-996, 502, U.S. 3,330,859, U.S. 3,944,594, U.S. 4,593,057, EP-A-154 518 or U.S. 3,960,928.
Of interest are compositions comprising as component (ß) products where, in the compound of formula III, s is number 1 or 2. Of specific interest are compositions comprising as component (ß) products in which , in the compound of the formula I, the radicals Y, independently of each other, are OH, (HOCH2CH2) 2N- or -HNR; L and Ri is hydrogen, C ^ -C ^ alkyl »- C5-C7 cycloalkyl,
1 C3-C6 alkenyl, benzyl or phenyl, in
where R2 is hydrogen, C1-C4 alkyl, OH, CH2CN, Cg-C12 alkoxy, C5-C8 cycloalkoxy, allyl, benzyl, acetyl or HCOCH2CH2- and a is number 1, 2, 3, 4 or 6, where
if Y is OH and a is 1, X is alkyl ^^ 30, C3-C18 alkenyl, -CH2CH2T1 (CH2CH0) ^ 4
or it is how it was defined before, and
T e R 4 is C 1 -C 10 alkyl, b is an integer ranging from 0 to 10, and R 5 is hydrogen, alkyl, -CO 3, or phenyl.
if Y is OH and a is 2,
X is -CH2CH2T2 (CH2CH20) bCH CH2-, wherein b has the above definitions,
O O - CH2CH2-NH -C -C - NH-CH2CH2 - or
R7 T is oxygen, sulfur, N-R-S-C-S- and R5 is as defined above. / 5 ° R'8 Rg is hydrogen, alkyl CI-C ^ Q, O phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 'independently from each other, they are hydrogen, alkyl c ~ c10 ° phenyl, or R7 and R8 together with the carbon atom to which they are attached, form a C5-C7 cycloalkyl ring, or if Y is -HNRi is already 1,
X is C 3 -C 8 alkyl, C 5 -C 7 cycloalkyl, benzyl, phenyl in which R 2 is as
ant or X was defined together with ^ is a group of the formula -CH2CH2CH CH2CH2 or CH2CH2? CH CH2-, where R ^ O is hydrogen or methyl and e is 2 or 3 and
in the compound of formula II,
the radicals Z are hydrogen or a group of the formula O - (ChH2hO) --C-R1, and k is an integer ranging from 0 to 4, where h is 2 or 3, i is an integer ranging from 0 to 6 and Rll is C1-C20 alkyl, C1-C20 alkenyl, C5-C7 cycloalkyl, phenyl or benzyl, with the proviso that the compound of formula II comprises a group - (ChHghO CR ^;
in the compound of the formula III R 1 is C 1 C alkyl, C 5 -C 7 cycloalkyl, phenyl or benzyl, s is 1 or 2,
where R ^ has the above definitions, m is an integer ranging from 0 to 3, R16 is alkyl C ± -C and n is an integer ranging from 1 to 6, where,
if n is 1, R17 is hydrogen, alkyl? -30, C5-C7 cycloalkyl, C2-C18 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol.
where R2 has the above definitions, or equally
R17 is C in which
T3 is ox R 9 is 12 and R15 are
as defined above, or R19 is likewise hydrogen, alkyl, O-c18-phenyl, C5-C7-cycloalkyl, or where p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is alkyl-C-Q, phenyl or C5-C8 cycloalkyl, R23 and R24 are not simultaneously methyl; R25 is hydrogen or C ^ -C-alkyl, or
if n is 2, R17 is a divalent radical of a hexose, a radical
where p and q have the above definitions,
-CH2CH2-T4-CH2CH2-, -CH2-CH = CH-CH2-, -CH2-C == C-CH2
wherein R18 and R20 'independently of each other, are hydrogen or C ^ -Cg alkyl, or together they are a radical -CH2CH2CH CH2CH2-, r is an integer ranging from 2 to 10,
N-Rj, or -s-c-s-t T4 is sulfur, / ', wherein R7 and R8 have the above definitions and R26 is hydrogen, CI-C ± Q alkyl, C5-Cg cycloalkyl, or
where R2 has the above definitions.
Preferred are compositions comprising as component (ß) products in which, in the compound of formula I, the radicals Y, independently of each other, are OH, (OH-CH2CH2) 2N- or -HNRi and
Rl is hydrogen, C-C4 alkyl, or where
R2 is hydrogen, C -C4 alkyl, OH, allyl, benzyl, acetyl or HOCH2CH2- and a is a number of 1,2,3,4 or 6, where
if Y is OH and a is 1, X is C -C 8 alkyl, C 3 -C 8 alkenyl,
-CH2CH2T, (CH2CH2O) bR4
wherein R2 is as defined above, and is oxygen, R4 is C1-C4 alkyl, and b is an integer ranging from 0 to 10, or
if Y is OH and a is 2, X is -CH2CH2T2 (CH2CH20) bCH2CH2-, where b has the above definitions or equally X is
where R5 is hydrogen, b is the number 0 or 1 and c is an integer that varies from 2 to 8, or
if a is 3
X is -CH? -CH-CH2- or N (CH2CH2-) 3,
if Y is OH and a is 4, CH2 'CH2- -CH2-C-CH2- (-CH2-CH-CH2) or -CH2-CH-CH2-0-CH-CH2-X is -V. , n2- > - -'- 'i > 2, v- \ _t '2"" CH2-if Y is OH is already 6 -CH2 CH2 X is ii -CH2-C-CH-0-CH2-C-CH2- -CH, -C 1H-C'H -CiH-CJlH-CH, - I -CH2 CH2-if Y is -HNRi is already 1,
X is C 1 -C 6 alkyl, C 3 -C 8 alkenyl,. C5-C7 cycloalkyl, or where R2 has the above definitions,
if Y is -HNRi and a is 2, X is CfH2f-, in which f is an integer that varies from 2 to 10 and
in the compound of formula II,
Or the radicals Z are hydrogen or a group of the formula. ^ U J] - (° H2h °) fC-R11 and k is l, 2 Ó 3, h is 2 or 3, i is an integer that varies from 0 to 4 and Rll is C? -C20 alkyl, or C8-C20 alkenyl, with the proviso that the compound of formula II comprises an O group p ChH2hO) tCR;
in the compound of formula III,
l2 is C alquilo-Cg alkyl or C5-C7 cycloalkyl, s is 1 -o 2, Q is -CmH2m- or -CH2-CH- > R 16 m is an integer ranging from 0 to 3, Rlg is C 1 -C 4 alkyl, and n is an integer ranging from 1 to 6, where,
if n is 1, R 7 is hydrogen, C 1 -C 8 alkyl, C 5 -C 7 cycloalkyl, C 2 -C 8 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol -CH 2,
wherein R2 has the above definitions, or likewise R17 is -f- (CH2) p04- (CH2) pOR19 in? to which R? g is hydrogen, C? -C 8 alkyl, or C5-C7 cycloalkyl, wherein p? is an integer that varies from 2 to 4, q is an integer that varies from 2 to 10, or
if n is 2, Rl7 is a divalent radical of a hexose, a radical -CH, divalent of a hexitol, -CH2-C-CH2OH -CrH2r- "(CH2) pO-" (CH2) CH2OH in which p and q have the definitions previous
CHCH-T4-CH2CH2-, c - wherein r is a tr.tero ranging from 2 to 10, 4 is sulfur or NR 10 26 / R2g is hydrogen, C? -C? 0 alkyl, or C5? C8 cycloalkyl, or
if n is 3, Rl7 is a trivalent radical of a hexose or a radical
Trivalent of a hexitol CHCH2- -CH2CH2-N-CH2CH2-CH2-CH-CH, CH3-CH-CH2-N-CH2-CH-CH,
if n is 4, Rl is a tetravalent radial of a hexose, a radical
Preference is also given to compositions comprising as component (ß) products in which, in the compound of formula I, the radicals Y, independently of one another, are hydroxyl or -NH2 is already an integer ranging from 1 to 4, where,
R is hydrogen, methyl or HOCH2CH -, or
if Y is OH and a is 2,
X is -CH2CH2T2 (CH2CH2O) bCH2CH2-, where -I »2 is oxygen, sulfur or N_R / 5 '
R5 is hydrogen, b is the number 0 or 1 and c is the number 2, 3 or 4 or
if Y is OH and a is 3, X is -C? 2 - ^? - H2- if Y is OH and a is 4,
in the compound of the formula II, OR the radicals Z are hydrogen or a group of the formula II -C-? rk is the number 1 and Rn is C -C20 alkyl, or C8-C2Q alkenyl, with the condition O that the The compound of the formula II comprises a group ¡-CR r ry in the compound of the formula III, Ri2 is tertiary butyl, R15 is C1-C4 alkyl, and is bonded in the ortho position with respect to the OH group, s is number 1, Q is -CItlH2m- and binds in the para position with respect to the OH group, where m is the number 2, n is 1 and Rl is C -C4 alkyl.
Examples of preferred compounds of formula I are pentaerythritol tiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine, glycerol. Particular preference is given to glycerol or tiodiethylene glycol. Preferred compounds of formula II are vegetable oils, which occur naturally, fats and waxes, animal oils and fats, as well as artificial polyol derivatives. Preferred vegetable oils, fats and waxes are, for example, sunflower oil, coconut fat, turnip oil, soybean oil, corn germ oil, safflower oil, olive oil, peanut oil, seed oil. of cotton, sesame oil, castor oil, tallow oil, pumpkin seed oil or flaxseed oil. Preferred animal oils and fats are, for example, butter fat, lard, fish oil, sperm oil, "cow paw" oil or whale oils. Examples of preferred artificial polyol derivatives are those of Radiamuls (glycerol tri C8 C? 0) or sorbitan derivatives. Sorbitan derivatives are commercially available, for example, under the names Span®20, Span®40, Span®60, Span®65, Span®80, Span®85, Tween 20®, Tween 40®, Tween 60®, Tween 65®, Tween 80® or Tween 85®,
Sunflower oil, coconut oil or turnip oil are particularly preferred. Of particular interest are compositions comprising as component (ß) products in which, in the compound of formula III, Ri2 is C1-C4 alkyl, or cyclohexyl, R5 is C1-C4 alkyl, or cyclohexyl and is attached to the ortho position in relation to the OH group, s is the number 1, Q is -CmH2ltl-, and joins in the para position in relation to the OH group, where m is an integer that varies from 0 to 3 and n is an integer that varies from 1 to 4, where,
if n is 1,
R17 is hydrogen, C? -C? 0 alkyl, cyclohexyl, alkenyl
CH2OH if n is 2,
R17 is 0 -CH2CH2-T4-CH2CH2- wherein p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, r is an integer ranging from 2 to 6,
-4 is sulfur or "? | -% c and Y2g is hydrogen or C1-C4 alkyl, or
if n is 3,
I
CH2CH2- CH2-CH-CH3 Rl7 is I -CH2CH2-N-CH2CH2- ~ CH3-CH-CH2-N-CH2-CH-CH3
if n is 4,
Of particular interest are compositions comprising as component (ß) products in which, in the compound of formula III,
Rl2 is tertiary butyl, Rl5 is C1-C4 alkyl, and is bonded in the ortho position with respect to the OH group, s is number 1, is -CmH2? ,, -, and binds in the para position relative to the group OH, where m is the number 2 and n is an integer, 1, 2, or, where,
if n is 1, R is C -C4 alkyl, or
if n is 2, R17 is - (CH2) p0 - where
p is number 2, q is number 2 and T4 is sulfur or
if n is 4
Other preferred compounds of formula III are
Particularly preferred compounds of formula III are methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, 3- (3'-tere. -butyl-4'-hydroxy) Methyl 5'-methylphenyl) -propionate. Particular preference is also given to compositions comprising, as component (ß), products which can be obtained by reacting components a), b) and e), component a) being a compound of formula I, in particular pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine, glycerol,
or a mixture thereof, component b) is a compound of formula II, in particular sunflower oil, coconut oil, turnip seed oil, corn germ oil, safflower oil, olive oil, oil of peanut or Radiamul or a mixture thereof, and component c) is a compound of formula III, in particular methyl 3- (3 ', 5'-diterc.-butyl-4 * -hydroxyphenyl) propionate or 3- (3'-tere. Methyl-4'-hydroxy-5'-methylphenyl) propionate. The present invention also relates to compositions comprising, as the component (ß), products that can be obtained by the reaction of components a), b) and c) in a quantitative molar ratio of 0.1: 1.0: 0.1 to 15: 1:30 A quantitative molar ratio of 1: 1: 1 to 10: 1: 20 is preferred. A quantitative molar ratio of 4: 1: 5 to 10: 1: 20 is particularly preferred. A quantitative molar ratio of 5: 1: 10 is especially preferred.
Of special interest are the compositions comprising, as the component (ß), products in which the amount by weight of the active group E-2
in the component (ß) it is from 30 to 80% by weight, preferably from 35 to 80% by weight, in particular from 50 to 80% by weight.
As already mentioned, the present products of the component (ß) have properties against wear and that inhibit corrosion in fuels. Particular mention is made of its outstanding improvement of lubricity (property against wear) of fuels with lower sulfur and / or aromatic contents. Therefore, the present invention also relates to the use of the component (ß) products as an anti-wear agent for a motor fuel system. As a rule, the component (ß) products are added to the fuel in amounts from 0.0001 to 10.0%, preferably from 0.001 to 0.2%, in particular from 0.005 to 0.1%, based on the weight of component (a). Component products (ß) can be mixed with liquid carriers, compatible with the fuels of the final product, to form concentrates for subsequent addition to fuel-based materials or formulated fuels. Such concentrates can facilitate the mixing, composition, emptying or transfer (in volume or in line) of the component products (ß). Typically, the carriers are organic solvents for the component (ß) products, such as hydrocarbons, such as, for example, xylene or toluene, ethers, alcohols or mixtures thereof, or they may be portions of materials a, fuel base or formulated fuels that are intended as the final products. The addition of the concentrates to the base materials of the formulated fuels, to form the fuels of the final product can be in batches, for example of single containers of concentrates, sold at retail or other products, or they can be added by dosage in the refineries or fuel distribution sites. Other modes of addition will be evident. The amount of the products of the component (ß) in the concentrate may vary, depending on the desired properties of the concentrate, such as the viscosity. Generally, about 10 to 90% by weight of the products of the component (ß) in the carrier medium is suitable, more usually around 20 to 50% by weight. The fuels of the final product can be hydrocarbon fuels, oxygenates or mixtures of the two. The hydrocarbon fractions that can be used for the fuel compositions include the distillate fuels having a boiling point in the range of kerosene and diesel (165 to 565ac). Typical middle distillate fuels of this class include diesel fuels for road and other diesel fuels, with boiling ranges ranging from 200 to 370ac, and jet fuel, kerosene, gas oil, and cycle oils. Such middle distillate fuels may comprise straight-run distillate oils, thermally decomposed distillate fuel oils, or mixtures of straight-run distillate fuel oils, naphthas, and the like with distilled thermal decomposition oils. These fuels are normally derived from petroleum, but they can be derived, at least in part, from other sources, such as shales, tar sands, coal, lignite, biomass and similar sources. The fuels may contain a proportion of oxygenated mixture components, such as alcohols or ethers, which include methyl ether and tertiary butyl ether (MTBE). The fuels may also fully comprise oxygenated products, such as methanol and / or ethanol. The fuels can also be those that have been subjected to conventional treatment processes, such as treatment with an acid or a base, hydrogenation, solvent refining or clay treatment. Of particular interest are the compositions comprising as component (a) a diesel fuel. The fuels can be used, for example, in the operation of a jet engine, a vehicle engine, a gas turbine engine or a diesel engine. In a preferred embodiment of this invention, the fuel is one which is suitable for use in a diesel engine.
The composition of these diesel fuels varies widely with the nature of the crude oil, the refining process, the components with which the untreated fuel is mixed, and the climate in which the fuel is sold. As noted above, this invention finds particular application in diesel fuels having a reduced content of sulfur and / or aromatics, which are now produced in order to comply with the requirements of the regulations. These fuels typically have sulfur contents below 500 ppm (0.05%) and / or an aromatic content less than 35% by weight. Of particular interest are, therefore, compositions comprising as component (a) a fuel, which contains less than 0.10%, preferably less than 0.05%, in particular less than 0.01% by weight of sulfur. The composition of the fuel and thus its inherent lubricity may vary according to the severity of the local regimen of regulations. The invention also finds application in aviation fuels, such as those commonly used in gas turbine engines. Such fuels have a narrow composition to that of diesel fuels that have a low aromatic and sulfur content. The addition of the products of the component (ß) of this invention to these fuels can reduce engine wear.
The invention may also find application in lead-free or reformulated automotive fuels, as is now commonly used in piston engines in aircraft and engine vehicles. The addition of the component (ß) products to these fuels can improve the performance of the engine and make it possible for the fuel to be replaced by unleaded fuel in uses such as in piston-engine aircraft, where fuel is currently used. unleaded. Therefore, the invention also relates to a process for the reduction of wear in a motor fuel system, which comprises adding a product of the component (ß) to the fuel. In addition to the component (ß) products, the compositions, according to the invention, may also contain conventional additives, which are added to improve the basic properties of the fuel even more, as discussed in the Lubricant and Fuel Auditives manual, published by Kline & Company, Inc., International Business Consultant, Fairfield, NJ, E.U.A., pages 309-320 (1990); they include: antioxidants, metal passivators, rust inhibitors, agents that improve the viscosity index, people that decrease the pour point, dispersants, detergents, high pressure additives, antifriction additives, antiwear additives, de-emulsifying agents, agents that reduce the point of darkness, anti-sedimentation waxy additives, anti-static additives, anti-foaming agents, anti-fog additives, biocides, odor-hiding agents, dyes, cetane-improving agents, antifreezes, anti-tapping additives, agents that improve conductivity, PFI / IVD cleaning additives and other lubricity additives. Examples of such conventional additives are the following:
l. Antioxidants 1.1 Alkylated monophenols, for example, 2,6-di-tert. -butyl-4-methylphenol, 2-tert. -butyl-4, 6-dimethylphenol, 2,6-di-tert. -butyl-4-ethylphenol, 2,6-di-tert. -butyl-4-n-buylphenol, 2,6-di-tert. -butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- (a-phenylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2 , 6-di-tert. -butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1 '-methylundec-1'-yl) phenol, 2,4-dimethyl-6- (1 • -methylheptadec-1 • -yl) phenol, 2,4-di-methyl-6- (1-ethyltridec-1-yl) phenol and mixtures thereof.
1. 2-hydroquinones and alkylated hydroquinones, for example
2, 6-di-tert. -butyl-4-methoxyphenol, 2, 5-di-tert. -butylhydroquinone, 2,5-di-tert. -hydrohydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tere. -butyl-4-hydroxyanisole, 3, 5-di-tert. -butyl-4-hydroxy-anisole, 3, 5-di-tert. -butyl-4-hydroxyphenyl-stearate, bis (3, 5-di-tert.-butyl-4-hydroxyphenyl) -adipate.
l3-alkylidenebisphenols. for example 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2 * -methylenebis (6-tert-butyl-4-ethylphenol), 2,2 • -methylenebis [4-] methyl-6- (a-methylcyclohexyl) -phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-4-methylphenol), 2,2'- methylenebis (4,6-di-tere-butylphenol), 2,2-ethylidebisbis (4,6-di-tert.-butylphenol), 2,2'-ethylidebis (6-tert-butyl-4-isobutylphenol) ), 2,2'-ethylenebis [6- (a-methylbenzyl) -4-nonylphenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4,4'-methylenebis (2,6-di-tert.-butylphenol), 4,4'-methylenebis (6-tert-butyl-2-methylphenol), 1,1-bis (5-tert.-butyl-4-hydroxy-2) -methyl-nyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1, 1,3-tris (5-tert -butyl-4-) hydroxy-2-methylpheneyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -3-n-dodecyl mercaptobutane, ethylene glycol-bis [3, 3 bis (3'-tere .- butyl-4 '-hydroxyphenyl) butyrate], bis (3-tert.-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadiene , bis [2- (3 '-tert.-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert. -butyl-4-methylphenyl] -terephthalate, 1,1-bis (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2'bis (3,5-di-tert.-butyl-4-hydroxyphenyl) propane , 2, 2-bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-n-dodecylmercapto-butane, 1, 1,5, 5-tetra- (5-tert.-butyl- 4-hydroxy-2-methyl-phenyl) pentane.
1. 4. Compounds of O- v N-benzyl. for example 3, 5,3 ', 5'-tetra-tert, -butyl-4,4 * -dihydroxydibenzyl ether or tris- (3, 5-di-tert-butyl-4-hydrobenzyl) amine.
1. 5. Hydroxybenzylated malonates. for example, dioctadecyl-2, 2-bis- (3, 5-di-tert-butyl-2-hydroxybenzyl) -malonate, di-octadecyl-2- (3-tert-butyl-4-hydroxy-5-) methylbenzyl) -malonate, didodecylmercaptoethyl-2, 2-bis- (3, 5-di-tert-butyl-4-hydroxy-benzyl) -malonate, bis- [4- (1,1,3,3-tetramethylbutyl) phenyl] -2, 2-bis (3, 5-di-tert.-butyl-4-hydroxybenzyl) -malonate.
1. 6. Hydroxybenzyl aromatic compounds. for example, 1, 3, 5- (3,5-di-tert.-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3, 5-di-tert.-butyl- 4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert.-butyl-4-hydroxy-benzyl) phenol.
1. 7. Triazine compounds. for example 2, 4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris- (3, 5-di- tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3, 5) di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1, 3, 5-tris (3,5-di-tert.-butyl-4-hydroxyphenyl-propionyl) -hexahydro-1, 3,5-triazine, 1,3,5-tris (3,5-di-cyclohexyl-4-hydroxybenzyl) isocyanurate.
1. 8. Benzophosphonates. for example dimethyl-2,5-di-tert. -butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert. -butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert. -butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert. -butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the 3,5-di-tert. -butyl-4-hydroxybenzylphosphonic acid.
1. 9. Acylaminophenols. for example, 4-hydroxylauranylide, 4-hydroxystearanilide, N- (3,5-di-tert.-butyl-4-hydroxy-phenyl) -carbamic acid octyl ester.
1. 10. steres of ß- (3,5-di-tert.-butyl-4-hydroxyphenyl) -propionic acid with monohydric or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol , ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3- tiapentadecanol, trimethylhexanediol, trimethylpropane, 4-hydroxymethyl-l-phospha-2, 6-7-trioxabicyclo [2.2.2] -octane.
1. 11. Esters of ß- (5-tert-butyl-4-hydroxy-3-methylphene) propionic acid with monohydric or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, tisdiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, -thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylpropane, 4-hydroxymethyl-l-phospha-2, 6-7-trioxabicyclo [2.2.2] -octane.
1. 12 Esters of ß- (3,5-dicyclohexyl-4-hydroxyphenyl) -propionic acid with monohydric or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonane-diol, ethylene glycol , 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylpropane, 4-hydroxymethyl-l-phospha-2, 6-7-trioxabicyclo [2.2.2] -octane.
1. 13. Esters of 3,5-di-tert. -butyl-4-hydroxyphenyl-acetic with monohydric or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodieti-len-glycol, diethylene glycol, triethylene glycol, penta-erythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylpropane, 4-hydroxymethyl -l-phospha-2, 6-7-trioxabicyclo [2.2.2] -octane.
1. 14. Amides of ß- (3,5-di-tert.-butyl-4-hydroxyphenyl) -propionic acid, for example N, N'-bis (3,5-di-tert.-butyl-4-hydroxyphenylpropionyl) hexamethyleneamine, N, N'-bis (3,5-di-tert.-butyl-4-hydroxyphenylpropionyl) hexamethylenediamine, N, N'-bis (3,5-di-tert.-butyl-4-hydroxyphenylpropionyl) trimethylenediamine, N, N'-bis- (3, 5-di-tert.-butyl-4-hydroxyphenylpropionyl) -hydrazine.
Examples of amine antioxidants: N, N'-diisopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis- (1,4-dimethylpentyl) -p-phenylenediamine , N, N'-bis (l-ethyl-3-methylpentyl) -p-phenylenediamine, N, N-bis (1-methylheptyl) -p-phenylenediamine, N, N '-dicyclohexyl-p-phenylenediamine, N, N '-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethyl-butyl) -N * -phenyl-p-phenylenediamine, N- (l-methylheptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N * -phenyl-p-phenylenediamine, 4- (p-toluenesulfamoyl) diphenylamine, -butyl- p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p, p * -diter, -octyldiphenylamine, 4-n-butylaminophenol , 4-butyryl-aminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis (4-methoxyphenyl) amine, 2,6-di-tert. -butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis [(2-methyl) phenyl) amino] -ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4- (I ', 3'-dimethylbutyl) phenyl] amine, N-phenyl-1-naphthylamine tere . -octilated, a mixture of tere. -butil / tere. mono- and dialkylated octyl diphenyl amines, a mixture of mono- and dialkylated isopropyl / isohexyldiphenylamines, tere mixtures. -butyldiphenylamine mono- and dialkylated, 2,3-dihydro-3/3-dimethyl-4H-l, 4-benzothiazine, phenothiazine, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut -2-one, N, N • bis (2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine, bis (2,2,6,6-tetramethylpiperid-4-yl) sebacate, 2,2,6 , 6-tetra-methylpiperidin-4-one and 2,2,6,6-tetramethylpiperidin-4-ol.
Examples of other antioxidants: aliphatic or aromatic phosphites, thiodi-propionic acid or thiodiacetic acid esters or salts of dithiocarbamic acid or dithiophosphoric acid, 2,2,12,12-tetramethyl-5,9-dihydroxy-3,7, -trithiatridecane and 2, 2, 15, 15-tetramethyl-5, 12-dihydroxy-3, 7,10, 14-tetrathiahexadecane.
Examples of metal deactivators, for example for copper, are; a) Benzotriazoles and their derivatives, for example the 4- or 5-alkylbenzotriazoles (for example tolutriazole) and their derivatives, 4,5,6,7-tetrahydrobenzotriazole and 5,5'-methylenebisbenzotriazole; Mannich or benzotriazole or tolutriazole bases, for example l- [bis (2-ethylhexyl) aminomethyl) tolutriazole and l- [bis (2-ethylhexyl) -aminomethyl) benzotriazole; and alkoxyalkylbenzotriazoles, such as l- (nonyloxymethyl) -benzotriazole, 1- (1-butoethyl) benzotriazole and l- (1-cyclohexyloxybutyl) -tolutriazole.
b) 1,2,4-triazoles and their derivatives, for example the 3-alkyl (or aryl) -1,2,4-triazoles, and the Mannich bases of the 1,2,4-triazoles, such as l- [bis (2-ethylhexyl) aminomethyl-1,2,4-triazole; alkoxyalkyl-1,2,4-triazoles such as l (l-butoxyethyl) -1,2,4-triazole; and the acylated 3-amino-l, 2,4-triazoles.
c) Imidazole derivatives, for example 4,4'-methylenebis (2-undecyl-5-methylimidazole) and bis [(N-methyl) imidazol-2-y1] carbinol-octy1-ether.
d) Heterocyclic sulfur-containing compounds, for example 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole and their derivatives; and 3, 5-bis [di (2-ethylhexyl) aminomethyl] -1,3,4-thiadiazolin-2-one.
e) Amino compounds, for example salicylimidepropyl diamine, salicylaminoguanidine and their salts.
Examples of oxide inhibitors are: a) Organic acids, their esters, metal salts, amine salts and anhydrides, for example alkyl- and alkenyl-succinic acids and their partial esters with alcohols, diols or hydroxycarboxylic acids, partial amides of alkyl acids and alkenyl succinic acids, 4- nonylphenoxyacetic acid, alkoxy and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, dodecyloxy (ethoxy) acetic acid and their amine salts, and also N-oleylsarcosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, for example, dodecenylsuccinic anhydride, 2-carboxymethyl-1-dodecyl-3-methylglycerol and their amine salts.
b) Nitrogen-containing compounds, for example:
I. Primary, secondary or tertiary amines, aliphatic or cycloaliphatic, and salts of amines of organic and inorganic acids, for example the oil-soluble alkylammonium carboxylates, and also the l- [N, N-bis (2-hydroxyethyl ) amino] -3- (4-n-nylphenoxy) propan-2-ol.
II. Heterocyclic compounds, for example substituted i-idazolines and oxazolines and 2-heptadecenyl-1- (2-hydroxyethyl) imidazoline.
c) Phosphorus-containing compounds, for example the partial amine salts of phosphoric acid, or partial phosphonic acid esters, and zinc dialkyldithiophosphates.
d) Sulfur-containing compounds, for example, barium dinonylnaphthalenesulfonates, calcium and petroleum sulfonates, aliphatic carboxylic acids substituted by alkylthio, esters of aliphatic 2-sulfocarboxylic acids and their salts.
e) Glycerol derivatives, for example glycerol monooleate, 1- (alkylphenoxy) -3- (2-hydroxyethyl) glycerols, 1- (alkylphenoxy) -3- (2,3-dihydroxypropyl) glycerols and 2-carboxyalkyl-1 , 3-dialkylglycerols.
Examples of agents that improve the viscosity index are: Polyacrylates, polymethacrylates, vinylpyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers and polyethers.
Examples of agenets that decrease the pour point are: polymethacrylate and alkylated naphthalene derivatives.
Examples of dispersants / surfactants are: Polybutenyl-succinic amines or imides, polybutenyl-phosphonic acid derivatives and basic sulfonates and phenolates of magnesium, calcium and barium.
Examples of anti-skid additives are; Compounds containing sulfur and / or phosphorus and / or halogen, for example sulfurized olefins, and vegetable oils, zinc dialkyldithiophosphates, alkylated triphenyl phosphates, tritolyl phosphate, triarylsyl phosphate, chlorinated pafins, alkyl di- and trisulfides and aryl, amine salts of mono- and dialkyl phosphates, amine salts of methylosphonic acid, diethanolaminomethyloltriazole, bis (2-ethylhexyl) aminomethylol thiazole, derivatives of 2,5-dimercapto, 1,3,4-thiadiazole, 3- [(diisopropoxyphosphintiosyl) thio] -ethyl propionate, triphenyl triphosphate (triphenylphosphorothionate), tris- (alkylphenyl) phosphorothionate and their mixtures (for example tris (isononylphenyl) phosphorothioate), diphenyl-monononylphenyl-phosphorothioate, isobutylphenyl-diphenyl-phosphorothioate, the dodecylamine salt of 3-hydroxy-3-oxide, 3-thiaphosphetane, trithiophosphoric acid, 5,5,5-tris [2-acetate isooctyl], 2-mercaptobenzothiazole derivatives, such as lNN-bis- (2-ethylhexyl) aminomethyl [-2-mercapto-lH- 1, 3-benzothiazole and ethoxy-carbonyl-5-octyldithiocarbamate. Conventional additives are added, for example, at concentrations of 0.01 to 10%, based on the total weight of the fuel. The (ß) component products of this invention can be combined with any of these additives, provided that the components of these mixtures are mutually compatible. The (ß) component products of this invention can be separately added to the fuel or they can be combined with one or more of the described additives to produce an aid formulation, which is suitable for addition to a base fuel. The following examples illustrate the invention in more detail. The parts and percentages are by weight, unless otherwise indicated.
Example 1: Preparation of sunflower oil derivatives with the use of pentaerythritol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) ropionate.
In a sulfonation flask, equipped with reflux condenser and mechanical stirrer, a mixture of 30 g (~ 34 mmol) of sunflower oil, 4.64 g (34 mmol) of pentaerythritol and 37 mf (0.15 mmol) of dibutyl ether tin were kept under nitrogen for 7 hours at 180-1902C. 9.94 g (34 mmol) of methyl 3- (3 ', 5 * -di-tert.-butyl-4'-hydroxyphenyl) propionate and another 37 mg (0.15 mmol) of dibutyl tin oxide were added. The stirring of the reaction mixture was continued for 15 hours at 180-1902C. When cooled, 40.64 g (91%) of the product was obtained as a yellow oil, having a n20D refractive index of 1.4882.
Example 2; Preparation of coconut oil derivatives, which use pentaerythritol and methyl 3- (3 ', 5'-di-tert.-butyl-4 • -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 403 g (~ 0.616 mol) of coconut fat, 83.1 g (0.610 mol) of pentaerythritol, 1.0 g (4 mmol) of dibutyltin oxide and 178.4 g were used. (0.610 mol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 653 g (98%) of the product as a brown oil, having a refractive index n20rj of 1.4781.
Example 3; Preparation of sunflower oil derivatives, which use thiodiethylene glycol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 50 g (~ 57 mol) of sunflower oil, 41.8 g (343 mmol) of thiodiethylene glycol, 448 mg (1.8 mmol of dibutyltin oxide and 200 mmol) were used. g (684 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 279.1 g (96%) of the product as a yellow oil, which has a refractive index n20D of 1.5170.
Example 4: Preparation of coconut oil derivatives, which use thiodiethylene glycol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 49.9 g (~ 76 mmol) of coconut fat, 85.1 g (688 moles) of thiodiethylene glycol, 797 mg (3.2 mmol) of dibutyl tin oxide were used and 402.6 g (1.38 mol) of methyl 3- (3 *, 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 500.7 g (93%) of the product as an orange-brown oil, which has a refractive index n20D of 1.5210.
Example 5: Preparation of sunflower oil derivatives, which use 1,4-butanediol and methyl 3- (3 ', 5 • di-tert.-butyl-4 * -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (~ 34 mmol) of sunflower oil, 14 g (155 mmol) of 1,4-butanediol, 199 mg (0.80 mmol) of dibutyl ether were used. tin and 87.7 g (300 mmoles) of methyl 3- (3 •, 5 * -di-tert.-butyl-4'-hydroxyphenyl) propionate, to supply 124 g (94%) of the product as a reddish oil, which it has a n20o refractive index of 1.5070.
Example 6: Preparation of coconut oil derivatives, which use 1,4-butanediol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example was repeated
1, except that 30 g (~ 46 mmoles) of coconut fat, 14 g (155 mmoles) of 1,4-butanediol, 199 mg (0.80 mmol) of dibutyl tin oxide and 87.7 g (300 mmoles) were used. of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 123 g (93%) of the product as a reddish oil, having a refractive index n 0rj of 1.5025.
Example 7: Preparation of sunflower oil derivatives, using 1,2-propanediol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate.
The procedure described in Example 1 was repeated, except that 30 g (~ 34 mmol) of sunflower oil, 12.2 g (160 mmol) of 1,2-propanediol, 199 mg (0.80 mmol) of dibutyl ether were used. tin and 87.7 g (300 mmol) of methyl 3- (3 ', 5' -di-tert.-butyl-4 • -hydroxyphenyl) propionate, to provide 121.7 g (93.7%) of the product as a yellow oil, which it has a refractive index n20rj of 1.5047.
Example 8: Preparation of sunflower oil derivatives, which use diethylene glycol and methyl 3- (3 ', 5' -di-tert.-butyl-4 • -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (~ 34 mmol) of sunflower oil, 16.7 g (157 mmol) of diethylene glycol, 199 mg (0.80 mmol) of dibutyltin oxide were used and 89.5 g (306 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 137.3 g (99%) of the product as a yellow oil, having a refractive index n20D of 1.5065.
Example 9: Preparation of coconut oil derivatives, using diethylene glycol and methyl 3- (3 •, 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (-46 mmol) of coconut fat, 22.3 g (210 mmol) of diethylene glycol, 249 mg (1.00 mmol) of dibutyltin oxide were used and 121.1 g (414 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 158.1 g (91%) of the product as a yellow oil, which it has a refractive index n 0D of 1.5068.
Example 10: Preparation of sunflower oil derivatives, and use triethylene glycol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example was repeated
1, except that 30 g (~ 34 mmol) of sunflower oil, 15 g (100 mmol) of triethylene glycol, 199 mg (0.80 mmol) of dibutyl tin oxide and 90.65 g (310 mmol) of 3 were used. - (3 ', 5'-di-tert.-butyl-4' -hydroxyphenyl) propionate, methyl. to provide 129 g (95%) of the product as a pale yellow oil, which has a refractive index n20 of 1.5050.
Example 11: Preparation of coconut oil derivatives, which use triethylene glycol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example was repeated
1, except that 30 g (~ 46 mmol) of coconut fat was used,
. 2 g (100 mmol) of triethylene glycol, 199 mg (0.80 mmol) of dibutyltin oxide and 90.65 g (310 min) of 3- (3", 5 '-di-tert.-butyl-4' - hydroxyphenyl) methyl propionate, to give 129.5 g (95%) of the product as a pale yellow oil, having a n20D refractive index of 1.4992.
Example 12: Preparation of the Radiamul derivatives, which use diethylene glycol and methyl 3- (3 *, 5'-di-tert.-butyl-4 • -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (~ 59 mmol) of Radiamuls (glycerol tri Cg / C o), 16.3 g (154 mmol) of diethylene glycol, 224 g (0.90 mmol) of sodium oxide were used. dibutyltin and 95.6 g (327 mmoles) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 132.6 g (99%) of the product as an pale yellow color, which has a refractive index n20j) of 1.5022.
Example 13: Preparation of sunflower oil derivatives, using diethanolamine and methyl 3- (3 •, 5'-di-tert.-butyl-4 • -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated except that 60 g (-68 mmol) of sunflower oil, 14.3 g (136 mmol) of diethanolamine, 149 mg (0.60 mmol) of dibutyltin oxide and 19.9 were used. g (68 mmol) of methyl 3- (3 ', 5' -di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 88.4 g (95%) of the product as a reddish-brown oil, which it has a refractive index n20D of 1.4940.
Example 14: Preparation of coconut oil derivatives, which use diethanolamine and methyl 3- (3 ', 5 * -di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 60 g (-92 mmol) of coconut fat, 19.1 g (182 mmol) of diethanolamine, 174 mg (0.70 mmol) of dibutyltin oxide and 34.2 were used. g (117 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 104.9 g (93%) of the product as a brown oil, which has a refractive index n20D of 1.4905.
Example 15: Preparation of sunflower oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example was repeated
1, except that 30 g (-34 mmoles) of sunflower oil, 14.22 g (154 mmoles) of glycerol, 199 mg (0.80 mmol) of dibutyl tin oxide and 87.73 g (300 mmoles) of 3- ( 3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate methyl, to give 126.5 g (96%) of the product as a pale yellow viscous oil, having a refractive index n20rj of 1.5128 .
Example 16: Preparation of coconut oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (-46 mmol) of coconut fat, 19.4 g (211 mmol) of glycerol, 249 mg (1.0 mmol) of dibutyltin oxide and 118 g were used. (404 mmol) 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate methyl, to give 154 g (92%) of the product as a pale yellow viscous oil, which has a refractive index n20 £) of 1.5123 ..
Example 17: Preparation of sunflower oil derivatives, using glycerol and methyl 3- (3 ', 5' -di-tert.-butyl-4 • -hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (-34 mmol) of sunflower oil, 14.5 g (157 mmol) of glycerol, 180 mg (0.72 mmol) of dibutyltin oxide and 75.20 g were used. (300 mmoles) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 105.0 g (94%) of the product as an orange oil, having an refractive index n20?) of 1.5165.
Example 18: Preparation of coconut oil derivatives, which use diethylene glycol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 1 was repeated, except that 30 g (~ 46 mmol) of coconut fat, 22.6 g (213 mmol) of diethylene glycol, 184 mg (0.70 mmol) of dibutyltin oxide were used and 94.3 g (390 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 131.9 g (98%) of the product as a yellow oil, which has a refractive index n 0D of 1.5118.
Example 19: Preparation of sunflower oil derivatives, using 4-hydroxy-2,2,6,6-methylpiperidine and 3- (3 ', 5'-di-tert.-butyl-4 • -hydroxyphenyl) Methyl propionate. The procedure described in Example 1 was repeated, except that 41.5 gg (-47 mmoles) of sunflower oil, 7.90 g (50 mmoles) of the 4-hydroxy-2,2,6,6-tetra-methylpiperidine were used, 50 mg (0.20 mmol) of dibutyltin oxide and 14.60 g (50 mmol) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 59.4 g ( 95%) of the product as a brown oil, which has a refractive index n20D of 1.4848.
Example 20: Preparation of sunflower oil derivatives, which use 4-amino-2,2,6,6-methylpiperidine and 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) Methyl propionate. The procedure described in Example was repeated
1, except that 41.5 g (-47 mmoles) of sunflower oil, 7.80 g (50 mmoles) of 4-amino-2, 2, 6,6-tetramethyl-piperidine, 50 mg (0.20 mmol) of oxide were used of dibutyl tin and 14.60 g (50 mmol) of methyl 3- (3 ', 5' -di-tert.-butyl-4 • -hydroxyphenyl) propionate, to give 61.8 g (99%) of the product as an oil of chestnut color, which has a refractive index n20D of 1.4887.
Example 21; Preparation of coconut oil derivatives, which use N- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethyl-piperidine and 3- (3 *, 5'-di-tert. methyl butyl-4'-hydroxyphenyl) -propionate. The procedure described in Example 1 was repeated, except that 31.0 g (-47 mmoles) of coconut fat, 10.1 g (50 mmoles) of N- (2-hydroxyethyl) -4-hydroxy-2,2 were used, 6,6-tetramethylpiperidine, 50 mg (0.20 mmol) of dibutyltin oxide and 14.60 g (50 mmol) of methyl 3- (3 ', 5 • -di-tert.-butyl-4' -hydroxyphenyl) propionate , to supply 52.4 g (98%) of the product as a yellow oil, which has a n20o refractive index of 1.4811.
Example 22: Preparation of turnip seed oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. In a sulfonation flask, equipped with reflux condenser and mechanical stirrer, a mixture of 116.3 g (~ 134 mmoles) of turnip seed oil, 86.1 g (935 mmoles) of 85% aqueous glycerol and 2.63 g (15.0 mmoles) ) of calcium acetate, was maintained for 7 hours under a nitrogen atmosphere at 180-190SC. Then 357.5 g (1.22 moles) of methyl 3- (3 •, 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate were added. The reaction mixture was continued to stir for 15 hours at 180-190ac. After cooling, 505 g (99%) of the product was obtained as a yellow oil having a nD refractive index of 1.5122.
Example 23: Preparation of corn germ oil derivatives, which use glycerol and methyl 3- (3 ', 5' -di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example was repeated
22, except that s used 100 g (~ 113 mmoles) of corn germ oil, 57.3 g (624 mmoles) of 85% aqueous glycerol, 2.32 g (13.0 mmoles) of calcium acetate and 282.4 g (966 mmoles) 3- (3 •, 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate methyl, to give 399.0 g (99%) of the product as a yellow oil, having a refractive index n20D of 1.5127.
Example 24; Preparation of sunflower oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 22 was repeated, except that 100 g (~ 113 mmol) of sunflower oil was used. 57.6 g (625 mmoles) of 85% aqueous glycerol, 2.11 g (12.0 mmoles) of calcium acetate and 286.5 g (980 mmoles) of 3- (3 ', 5' -di-tert.-butyl-4 '- hydroxyphenyl) methyl propionate, to provide 403.2 g (99%) of the product as a yellow oil, having a n20D refractive index of 1.5140.
Example 25; Preparation of olive oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 22 was repeated, except that 100g (~114mmol) of olive oil, 58g (630mmol) of 85% aqueous glycerol, 2.11g 12.0mmol) of calcium acetate and 290.4 were used. g (963 mmoles) of methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 408.6 g (99%) of the product as a yellow oil, which has a refractive index n 0n of 1.5110.
Example 26; Preparation of peanut oil derivatives, which use glycerol and methyl 3- (3 ', 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate. The procedure described in Example 22 was repeated, except that 100 g (~114 mmol) of peanut oil were used 58.0 g (630 mmol) of 85% aqueous glycerol, 2.11 g (12.0 mmol) of calcium acetate and 291.4 g (967 mmoles) of methyl 3- (3 •, 5'-di-tert.-butyl-4'-hydroxyphenyl) propionate, to give 413.5 g (99%) of the product as a yellow oil, which has a refractive index n20D of 1.5100.
Example 27: HFRR (High Frequency Reciprocal Equipment) test for low sulfur diesel fuel. The anti-wear properties of the component (ß) products in a low sulfur diesel fuel (available from EMPA, Switzerland) have been tested with the use of the fuel lubricity tester, the HFRR, under the prescribed conditions by the CEC test method F-06-A-96, which is available from CEC Secetariat, Place Madow 1, B-1030 Brussels, Belgium; or SAE Order Department 782, 400 Commonwealth Drive, Arrendale, PA 15096, USA, The details of the test method are described, for example, in Wei Dan Ping and HA Spikes, Wear, 111, 217-235 (1986) or ei Dan Ping, S. Korcek and HA Spikes, SAE 962010. With the HFFR tester, the lubricity of a fuel sample was evaluated through the wear measurement that occurred after 75 minutes of an oscillatory displacement of a steel ball against a flat disk. The diameter of the ball is 6.00 mm, the displacement frequency is 50 Hertz, its stroke length is 1 mm and the load applied to the ball is 200 g. The ball and the flat disk were immersed in the fuel to be tested. Other conditions, such as relative humidity, have an influence on the results and must be kept within the prescribed limits. At the end of the test duration of the wear signal on the ball a correction was measured and applied which normalizes all the results of a standard water vapor pressure of 14 mbar. The results are supplied in microns (μm). A reference of high lubricity and low lubricity are available for calibration. The high lubricity fuel gives a wear mark in the range of 380 to 437 μm. The low lubricity fuel gives a wear mark in the range of 600 to 760 μm. Both fuels are available through the CEC working group. The lower the wear mark, the better the anti-wear properties of the component (ß) products in the low sulfur diesel fuel. The results are summarized in Table 1. Table 1: HFFR test for low sulfur diesel fuel
Claims (17)
- CLAIMS 1. A fuel composition against wear, which comprises: a) a fuel and ß) at least one product, which can be obtained by reaction of components a), b) and c), where component a) is a compound of formula I or a mixture of compounds of formula I, component b) is a compound of formula II or a mixture of compounds of formula II and component c) is a compound of formula III or a mixture of compounds of the formula III, (I) (ni) (II) wherein, in the compound of formula I, the radicals Y, independently of each other, are OH (HOCH2CH2) N- or -HNRi And the radicals Ri are hydrogen, C -C 8 alkyl, C -C cycloalkyl? , C al-C alkenyl, C 7 -C 9 phenylalkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A, these radicals Ai, independently of each other, are C 1 -C 12 alkyl, halogen, hydroxyl, methoxy or ethoxy, wherein R 2 is hydrogen, C?-C8 alkyl, 0o, OH, NO, -CH2CN, l-18 alkoxy, C5-C?-cycloalkoxy, C C-alkenyl, C fen-C9 phenylalkyl, or C7-C9 phenylalkyl, which is mono - di- or tri-substituted on the phenyl ring by C1-C alkyl, or R2 is also C? -C8 acyl, or HOCH2CH2-, is already the number 1, 2, 3, 4 or 6, where, If Y is OH and a is 1, X is C1-C45 alkyl, C3-C8 alkenyl, -CH2CH2T (CH2CH20)), R4 in which R2 has the definitions previous and Ti is oxygen, sulfur or N-. / 5 'R4 is alkyl CI-C Q, b is an integer varying from 0 to 10 and R5 is hydrogen, C? -C? 8 alkyl, or phenyl or If Y is OH and a is 2, it is -CH2CH2T2 (CH2CH20) bCH2CH2-, where b has the above definitions, c O O - CH2 - CH = CH - CH2 - f - CH2CH2 - NH - C - NH - CH? CH _ or CH3 CH2CH20 - - C < ~ ° CH2CH2- CH, where T2 is oxygen, sulfur, N-R50 -SCS and R5 has the I R8 definitions above, Rg is hydrogen, C -C 8 alkyl, or phenyl, c is an integer ranging from 2 to 10, d is an integer that it varies from 2 to 6 and Ry and R, independently of each other, are hydrogen, alkyl l ~ 18 '° phenyl, or Ry and R8 together with the C atom to which they bind, form a cycloalkyl ring C? -C? 2, or if a is 3, X is C3-C10 alkanetriyl, or N (CH2CH2-) 3, or if Y is OH and a is 4, X is C4-C10, C3-Coteotetrayl, (-CH2-CH-CH2) 20, -CH2-CH-CH2-0-CH-CH. where Rg is C1-C4 alkyl, if Y is OH and a is 6, X is CH or alkanohexayl C -C Q, or, if Y is HNRi Y a is 1, X is C 1 -C 8 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl, phenylalkyl Cy-C 9, phenyl, where R2 is as defined before or X is also or X together with Rj_, is a group of the formula -CH2CH2CH2CH2CH2- or -CH2CH2OCH2CH2-, where R O is hydrogen or methyl and e is 2 or 3, or, if Y is -HNRi and a is 2, X is -CfH2f- _cffHll2f 'CH2CH2-, where f is an integer that varies from 2 to 10 and g is an integer that varies from 1 to 6, and in the compound of the formula II, the radicals Z are hydrogen or a group of the formula: O ll and ChH2h0) rC-R k is an integer that varies from 0 to 6, where h is 2 or 3, i is an integer that varies from 0 to 12 and Rn is. alkyl-030, C8-C30 alkenyl, C4-C2 cycloalkyl, phenyl or phenyl-C7-C9 alkyl, with the proviso that the compound or formula II has a group - (chH2ho; rc-R1 ?; in the compound of the formula III, R 2 is C 1 -C 8 alkyl, C 5 C 2 cycloalkyl, phenyl or phenylalkyl Cy-C 9, s is 0, 1 or 2, wherein R 5 is as defined above, m is an integer ranging from 0 to 3, i6 is C C-C8 alkyl, and n is an integer ranging from 1 to 6, where if n is 1, Ri7 is hydrogen, C-C45 alkyl, C5-C2 cycloalkyl, C2-C8 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol, -CH 'where R2 has the above definitions or likewise Riy is CH2CH2-T3-R? 9 or where \ T3 is oxygen, sulfur or N R22 R19 is where R? and R15 are as defined above, or R19 is also hydrogen, C ~ C4 alkyl, phenyl, C5-C2 cycloalkyl or O 11, where -CHg-C-O-Rjjs, p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is alkyl C? -C? 8, phenyl or phenyl which is substituted by 1 to 3 radicals Aif wherein the radicals A , independently of one another, are C 1 -C 2 alkyl, halogen, hydroxyl, methoxy or ethoxy, or R 22 is also C 5 -C 8 cycloalkyl, R 23 and 24 f independently of each other, are hydrogen or methyl, with the proviso that 23 and R 24 do not they are simultaneously methyl; R24 is hydrogen or C-24 alkyl, or if n is 2, R17 is a divalent radical of a hexose, a divalent radical of a hexitol, -CH -) - (CH2) pO- | - (CH2) p- § C.H 2r ~ in which p and q are as defined above, -CH2CH -T4-CH2CH-, -CH2-CH = CH-CH2-, -CH2-C = C-CH2-, wherein R18 and R20 'independently of each other, are hydrogen or C? -C? 2 alkyl, or together are the radial -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, ? T4 is sulfur, N-RI or -SCS- where R7 and R8 / IR «have the above definitions and R g is hydrogen, C? -C? 8 alkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A? , where the radicals Ai are as defined above in formula I, or R2g is also C5-C8 cycloalkyl, or where R2 has the above definitions, if n is 3, Rl7 is a trivalent radical of a hexose, a trivalent radical of a hexitol, CCHH22CCHH-I -CH2CH2-N-CH2CH2- ' where R 27 is hydrogen, CH 2 H, C 1 -C alkyl, C 1 -C 8 alkylamido, or where Q, Ri2 and R? 6 have the above definitions, or if n is 4, Rl7 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol, alcanotetrail if h is 5, Rl7 is a pentavalent radical of a hexose or a radial Rl7 is a hexavalent radical of a hexitol or
- 2. A composition, according to claim 1, wherein, in the compound of the formula III, s is the number 1 or 23. A composition, according to claim 1, wherein, in the compound of the formula I, the radicals Y, independently of each other, are: OH, (HOCH2CH2) 2N- or -HN i and Ri is hydrogen, alkyl cl ~ c10"C5-C7 cycloalkyl, C3-C6 alkenyl, benzyl or phenyl, wherein R2 is hydrogen, C1-C4 alkyl, OH, CH2CN, C6-C alkoxy? , C5 ~ C8 cycloalkoxy, allyl, benzyl, acetyl or HCOCH CH2- and a is number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, X is C? -C30 alkyl, C3-C18 alkenyl, -CH2CH2T? (CH2CH20) bR4 T is oxygen, sulfur or N_R / R4 is C 1 -C 6 alkyl, b is an integer ranging from 0 to 10 and R 5 is hydrogen, alkyl CI-CIQ or phenyl or if Y is OH and a is 2, X is -CH2CH2T2 (CH2CH20) bCH2CH2-, in which b has the above definitions, O O - CH2CH2 - NH - C - C - NH - CH2CH2 - or wherein? R? 77 T is oxygen, sulfur, N-R 50 -S-C-S and R 5 is as defined previously. R « R6 is hydrogen, alkyl CI-CIQ, O phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 'independently of each other, are hydrogen, alkyl l ~ c10 ° phenyl, or R7 and R8 together with the carbon atom to which they are attached, form a C5-C7 cycloalkyl ring, or if Y is -HNRi and a is 1, X is alkyl C? -C? 0, C3-C? alkenyl? 8, C5-C7 cycloalkyl, benzyl, phenyl, to R2 is like it was defined before or or X together with Ri cs a group of the formula -CH2CH2CH CH2CH2 or CH2CH20CH2CH2-, where R or is hydrogen or methyl and e is 2 or 3 and in the compound of formula II, the radicals Z are hydrogen or a group of the formula O and k- is an integer ranging from 0 to 4, where h is 2 or 3, i is an integer ranging from 0 to 6 and Rn is alkyl C? -C20 C, -C20 alkenyl, C5-C7 cycloalkyl, phenyl or benzyl, with the proviso that the compound of formula II comprises a group; in the compound of the formula III Ri2 is C ^ C alkyl, C5-C7 cycloalkyl, phenyl or benzyl, s is 1 or 2, Q is CmmH112m "'-CH, wherein R15 has the above definitions, is an integer ranging from 0 to
- 3, Rlg cs C1-C4 alkyl and n is an integer ranging from 1 to 6, where, if n is 1, R 7 is hydrogen, C 1 -C 30 alkyl, C 5 -C 7 cycloalkyl, C 2 -C 8 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol. where R has the above definitions, or equally Ri7 is CH2CH2-T3-R? 9 or | ~ (CH2) p ° -MCH2) pOR19, in which T3 is oxygen, sulfur or N - R 22 / R19 is where Ri2 and i5 are as defined above, or R19 is likewise hydrogen, alkyl, O-c18-phenyl, C5-C7-cycloalkyl or 11-H- -rc- where p is an integer ranging from 2 to 4, q is an integer that varies from 2 to 20, R22 is C 1 -C 8 alkyl, phenyl or C 5 -C 8 cycloalkyl, R 23 and R 24 are not simultaneously methyl; R25 is hydrogen or C -C 8 alkyl, or if n is 2, Rl7 is a divalent radical of a hexose, a radical where p and q have the above definitions, -CH2CH2-T4-CH2CH2-, -CH2-CH = CH-CH2-, -CH2-C = C-CH2- wherein R18 and R20 'independently of each other, are hydrogen or C? -Cg alkyl, or together are a radical -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, T 4 is sulfur, S, wherein R 7 and R 8 have the above definitions and R g is hydrogen, C 1 -C 6 alkyl, C 5 cycloalkyl, or where R2 has the above definitions.
- 4. A composition, according to claim 1, wherein, in the compound of formula I, the radicals Y, independently of each other, are OH, (OH-CH2CH2) 2N- or -HNRi and Rl is hydrogen, C? -C4 alkyl, or where R2 is hydrogen, C?-C4 alkyl, OH, allyl, benzyl, acetyl or HOCH2CH2- and a is a number of 1,2,3,4 or 6, where if Y is OH and a is 1, X is C 1 -C 8 alkyl, C 3 -C 8 alkenyl, wherein R2 is as defined above, and Ti is oxygen, R4 is C -C4 alkyl, and b is an integer ranging from 0 to 10, or if Y is OH and a is 2, X is -CH2CH2T2 (CH2CH20) bCH2CH2-, where b has the above definitions or equally X is - C c-Hp2, c ~ - CH2-CH = CH-CH2 - wherein T2 is oxygen, sulfur or N-R / 5 ' R5 is hydrogen, b is the number 0 or 1 and c is an integer that varies from 2 to 8, or if a is 3 X is -CH2-CH-CH2- or N (CH2CH2-) 3, if Y is OH it is already 4, CH2- C 2- II "H" X is -CH2-C-CH2- ^ (-CH2-CH-CH2) 20 0 -CH2-CH-CH2-0-CH-CH CH, if Y is OH it is already 6, X is -C 0 -CH 2 -CH-CH-c? -H-CH 2 -, if Y is -HNR and a is 1, X is C 1 -C 0 alkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkyl, or where R2 has the above definitions, or if Y is -HNRi and a is 2, X is CfH2f-, in which f is an integer ranging from 2 to 10 and in the compound of formula II, the radicals Z are hydrogen or a group of the formula O - (ChH2hO) rC-Rr (Y is 1, 2 or 3, h is 2 or 3, i is an integer ranging from 0 to 4 and ll is alkyl CI- C2Q, or C8-C2Q alkenyl, with the proviso that the compound of formula II comprises an O group || - (ChH2hO) rC-R1 ?; in the compound of formula III, R 2 is C 1 -Cg alkyl or C 5 -C 7 cycloalkyl, s is 1 or 2, Q is -CmH 2m- or "CH 2 -CH- § R 16 m is an integer ranging from 0 to 3, Rig is C 1 -C 4 alkyl, and n is an integer that varies from 1 to 6, where, if n is 1, Ri7 is hydrogen,? -C? 8 alkyl, C5-C7 cycloalkyl, C2-C? 8 alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol, CH? , where R2 has the above definitions, or equally i is -I- (CH2) pO - (CH2) pOR19 in which Rig is hydrogen, C -C 8 alkyl, or C 5 -C cycloalkyl, wherein p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, or if n is 2, Rl7 is a divalent radical of a hexose, a divalent radical of a hexitol, -CH, where p and q have the above definitions -CH2CH2-T4-CH2CH2-, or. -CH2CH2-N where CH CH, r is an integer that varies from 2 to 10, \ T4 is sulfur or N - Roe and R26 is hydrogen, C? -C? 0 alkyl, or C5-C8 cycloalkyl, or if n is 3, Ri7 is a trivalent radical of a hexose or c.,. trivalent radical of a hexitol CCHH2CCHH22-- CH2CH2-N-CH2CH2- CH2-CH-CH CH3-CH-CH2-N-CH2-CH-CH3 if n is 4, Rl7 is a tetravalent radial of a hexose, a tetravalent radical of a hexitol, CH3-CH-CH2 CH-j-CH-CHa NN-CH2CH2-N CH3-CH-CH N CH2-CH-CH3 i I
- 5. A composition, according to claim 1, wherein, in the compound of formula I, the radicals Y, independently of each other, are hydroxyl or -NH2 is already an integer varying from 4, where, if a is 1 R2 is hydrogen, methyl or HOCH2CH2-, or if Y is OH and a is 2, where \ T2 is oxygen, sulfur or N _ s, / R5 is hydrogen, b is the number 0 or 1 and c is the number 2, 3 or 4 or if Y is OH and a is 3, X is -CH2-CH-CH2-, if Y is OH and a is 4, CH2- I X is -CH2-C-CH9- and I CH2- in the compound of formula II, Or the radicals Z are hydrogen or a group of the formula j1k is the number 1 and Rll is alkyl CI-C2Q, or C8-C2Q alkenyl, with the proviso that the compound of the formula II comprises a group -C-R1t and in the compound of the formula III, Ri2 is tertiary butyl, R15 is C alquilo-C4 alkyl, and is bonded in the ortho position with respect to the OH group, s is number 1, Q is -CroH2lll- and is attached in the position for relative to the OH group, where m is the number 2, n is 1 and Rl7 is C1-C4 alkyl.
- 6. A composition, according to claim 1, wherein, in the compound of the formula III, R 2 is C -C 4 alkyl, or cyclohexyl, R 5 is C 1 -C 4 alkyl, or cyclohexyl and is attached at the ortho position in relation to the OH group, s is the number 1, Q is -CmH2? n-, and joins in the para position in relation to the OH group, where m is an integer that varies from 0 to 3 and n is an integer that varies from 1 to 4, where, if n is 1, Rl7 is hydrogen, C-CQ alkyl, cyclohexyl, alkenyl CH20H c2 ~ c18 '° -CH2-C-CH2OH * CH2OH if n is 2, Ri7 is -CH2CH2-T4-CH2CH2- wherein p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, r is an integer ranging from 2 to 6, \ T4 is sulfur or N -R26 / R26 is hydrogen or C1-C4 alkyl, or if n is 3, if n is 4,
- 7. A composition, according to claim 1, wherein, in the compound of the formula III, R 2 is tertiary butyl, l 5 is C 1 -C 4 alkyl, and is bonded in the ortho position with respect to the OH group, s is the number 1, Q is -CmH 2m-, and is bonded in the para position with respect to to group OH, where is number 2 and n is an integer, 1, 2, or 4, where, if n is 1, R1 is C1-C4 alkyl, or if n is 2, Rl7 is -f- (CH2) pOj- (CH2) p- 0 CH2CH2-T4-CH2CH2- where p is number 2, q is number 2 and 4 is sulfur or if n is 4
- 8. A composition, according to claim 1, wherein the compound of the formula I is pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine, glycerol, OH the compound of formula II, is sunflower oil, coconut oil, turnip seed oil, corn germ oil, safflower oil, olive oil, peanut oil or Radiamuls, and the compound of the Formula III, in methyl 3- (3 ', 5'-diterc. -butyl-4 * -hydroxyphenyl) propionate or 3- (3'-tere. -butyl-4'-hydroxy-5 • -methylphenyl) -Methyl propionate.
- 9. A composition, according to claim 1, wherein the molar quantitative ratio of components a), b) and e) is from 0.1: 1: 0.1 to 15: 1: 30.
- 10. A composition, according to claim 1, wherein the amount by weight of the active group E-2: in the component (ß) is from 30 to 80% by weight.
- 11. A composition, according to claim 1, wherein the first components a) and b) are reacted with each other and the resulting intermediate product is reacted with the component c).
- 12. A composition, according to claim 1, wherein the component (a) is a hydrocarbon fuel, an oxygenated fuel or a mixture thereof.
- 13. A composition, according to claim 1, wherein the component (a) is a diesel fuel.
- 14. A composition, according to claim 1, wherein the component (a) is a fuel containing less than 0.10% by weight of sulfur.
- 15. A composition, according to claim 1, which contains the component (ß) in an amount of 0.0001 to 10%, based on the weight of the component (a).
- 16. A method for reducing the wear of an engine fuel system, which comprises adding a component (ß), according to claim 1, to the fuel.
- 17. The use of the component (ß), according to claim 1, as an anti-wear agent for a motor fuel system. SUMMARY OF THE INVENTION Lubricity (anti-wear properties) of fuels is improved, for example, hydrocarbon oils, oxygenated fuels or mixtures thereof, particularly diesel or aviation fuels, which have a reduced content of sulfur and / or aromatics, to comply with the regulatory requirements, by the addition of at least one product, which can be obtained by the reaction of components a), b) and e), where component a) is a compound of formula I or a mixture of compounds of formula I, component b) is a compound of formula II or a mixture of compounds of formula II and component c) is a compound of formula III or a mixture of compounds of formula III: (III) (0 (ID in which the general symbols are as defined in claim 1, the compound of formula I is, for example, pentaerythritol tiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, glycol, diethanolamine or glycerol, the compound of formula II is, for example, sunflower oil or coconut fat, and the compound of formula III is, for example, 3- (3 ', 5' -di methyl-4-methyl-4 '-hydroxyphenyl) -propionate. The aforementioned products also improve the corrosion inhibition.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97810052.7 | 1997-02-03 | ||
EP97810052 | 1997-02-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9800903A MX9800903A (en) | 1998-08-30 |
MXPA98000903A true MXPA98000903A (en) | 1998-11-12 |
Family
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