JP5701860B2 - 第四級アンモニウムアミドおよび/またはエステル塩 - Google Patents
第四級アンモニウムアミドおよび/またはエステル塩 Download PDFInfo
- Publication number
- JP5701860B2 JP5701860B2 JP2012510858A JP2012510858A JP5701860B2 JP 5701860 B2 JP5701860 B2 JP 5701860B2 JP 2012510858 A JP2012510858 A JP 2012510858A JP 2012510858 A JP2012510858 A JP 2012510858A JP 5701860 B2 JP5701860 B2 JP 5701860B2
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- JP
- Japan
- Prior art keywords
- detergent
- acylating agent
- quaternized
- diaminopropane
- hydrocarbyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Quaternary ammonium amide Chemical class 0.000 title description 63
- 239000003599 detergent Substances 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 104
- 239000000446 fuel Substances 0.000 claims description 82
- 239000003795 chemical substances by application Substances 0.000 claims description 81
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 25
- 150000001408 amides Chemical class 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000001302 tertiary amino group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 239000003586 protic polar solvent Substances 0.000 claims description 15
- 238000002485 combustion reaction Methods 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 239000007859 condensation product Substances 0.000 claims description 11
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002816 fuel additive Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 9
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 9
- PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 claims description 8
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 8
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 7
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 6
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 150000003512 tertiary amines Chemical group 0.000 claims description 6
- PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 claims description 5
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 claims description 5
- STWODXDTKGTVCJ-UHFFFAOYSA-N 4-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1C1CCNCC1 STWODXDTKGTVCJ-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 claims description 5
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 claims description 5
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 claims description 5
- SORARJZLMNRBAQ-UHFFFAOYSA-N n,n',n'-trimethylpropane-1,3-diamine Chemical compound CNCCCN(C)C SORARJZLMNRBAQ-UHFFFAOYSA-N 0.000 claims description 5
- UICCSKORMGVRCB-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNCCN(CC)CC UICCSKORMGVRCB-UHFFFAOYSA-N 0.000 claims description 5
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 5
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 claims description 5
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 claims description 4
- ULDIVZQLPBUHAG-UHFFFAOYSA-N n',n',2,2-tetramethylpropane-1,3-diamine Chemical compound CN(C)CC(C)(C)CN ULDIVZQLPBUHAG-UHFFFAOYSA-N 0.000 claims description 4
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims description 4
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims description 4
- YYAYTNPNFKPFNG-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propan-1-amine Chemical compound CC1CCCCN1CCCN YYAYTNPNFKPFNG-UHFFFAOYSA-N 0.000 claims 3
- 150000008065 acid anhydrides Chemical class 0.000 claims 3
- MKDYQLJYEBWUIG-UHFFFAOYSA-N n',n'-diethyl-n-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 claims 3
- 125000001453 quaternary ammonium group Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 description 71
- 230000000996 additive effect Effects 0.000 description 36
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 34
- 150000002148 esters Chemical class 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 229930195733 hydrocarbon Natural products 0.000 description 20
- 150000002430 hydrocarbons Chemical class 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 239000004215 Carbon black (E152) Substances 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
- 229960002317 succinimide Drugs 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000002270 dispersing agent Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 11
- 229920002367 Polyisobutene Polymers 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000004185 ester group Chemical group 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical class NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000002283 diesel fuel Substances 0.000 description 7
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000002272 engine oil additive Substances 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000005462 imide group Chemical group 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 3
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000008050 dialkyl sulfates Chemical group 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- VKKTUDKKYOOLGG-UHFFFAOYSA-N 1-(diethylamino)propan-1-ol Chemical compound CCC(O)N(CC)CC VKKTUDKKYOOLGG-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- GGJSWHVQHRPELC-UHFFFAOYSA-N 2-ethylnonan-1-ol Chemical compound CCCCCCCC(CC)CO GGJSWHVQHRPELC-UHFFFAOYSA-N 0.000 description 2
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000000132 electrospray ionisation Methods 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000010763 heavy fuel oil Substances 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- WLNSKTSWPYTNLY-UHFFFAOYSA-N n-ethyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCNCCN(C)C WLNSKTSWPYTNLY-UHFFFAOYSA-N 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000010248 power generation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2381—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds polyamides; polyamide-esters; polyurethane, polyureas
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
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Description
本発明の第四級アミドおよび/またはエステル清浄剤は、(a)第三級アミン官能基を持つ非四級化アミドおよび/またはエステル清浄剤と、(b)四級化剤との反応生成物と説明してもよい。いくつかの実施形態では、非四級化清浄剤は、(i)ヒドロカルビル置換アシル化剤と、(ii)前記アシル化剤と縮合できる酸素または窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物である。
本発明に使用するのに好適な非四級化アミドおよび/またはエステル清浄剤は、(i)ヒドロカルビル置換アシル化剤と、(ii)前記アシル化剤と縮合できる酸素または窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含み、得られた清浄剤は、少なくとも1つの第三級アミノ基を持ち、さらにアミド基および/またはエステル基を含む。典型的には、前記アシル化剤と縮合できる酸素または窒素原子を持つ化合物により、得られた清浄剤が、アミド基を含むか、またはエステル基を含むかどうかは決定された(determined)。いくつかの実施形態では、非四級化清浄剤およびそれから得られた四級化清浄剤は、イミド基をまったく含まない。いくつかの実施形態では、非四級化清浄剤およびそれから得られた四級化清浄剤は、エステル基をまったく含まない。こうした実施形態では、本清浄剤は、アミド基を少なくとも1つ、または1つのみ含む。
(R1)(R2)C=C(R6)(CH(R7)(R8)) (I)
式中、R1およびR2は各々独立に水素、または炭化水素系基であり;R6、R7およびR8は各々独立に水素、または炭化水素系基であり、好ましくは少なくとも1つは少なくとも20個の炭素原子を含むヒドロカルビル基である。
(R3C(O)(R4)nC(O))R5 (IV)
および
本発明の四級化アミドおよび/またはエステル清浄剤は、上述の非四級化清浄剤を四級化剤と反応させると、形成される。好適な四級化剤として、選択された硫酸ジアルキル、ハロゲン化ベンジル、ヒドロカルビル置換カルボネート;酸と組み合わせたヒドロカルビルエポキシド、またはこれらの混合物が挙げられる。
本発明の四級化アミドおよび/またはエステル清浄剤は、燃料組成物および添加剤濃縮組成物など様々な種類の組成物中で添加剤として使用してもよい。
本発明の四級化清浄剤は、燃料組成物の添加剤として使用してもよい。本発明の燃料組成物は、上述の燃料添加剤および液体燃料を含み、内燃機関または開放火炎バーナーへの燃料供給に有用である。これらの組成物は、1種または複数種の追加添加剤をさらに含んでもよい。これらの任意の添加剤については以下に記載する。いくつかの実施形態では、本発明に使用するのに好適な燃料として、市販されている任意の燃料が挙げられ、いくつかの実施形態では、市販されている任意のディーゼル燃料および/またはバイオ燃料が挙げられる。
添加剤濃縮物は、1種または複数種の添加剤を含み、さらにある種の燃料、油または希釈液もある程度の量含む組成物である。こうした濃縮物はその後、添加剤の取り扱いおよび提供に都合がよいように、他の組成物に加えてもよく、その結果、上述の燃料組成物などの最終組成物が得られる。
本発明の燃料および添加剤組成物は、上述の四級化清浄剤を含み、さらに1種または複数種の追加添加剤も含む。こうした追加の性能添加剤は、内燃機関の種類、およびその機関に使用されている燃料の種類、燃料の質、ならびに機関を運転する使用条件を含むいくつかの因子に応じて、燃料組成物に加えてもよい。
本発明は、四級化アミドおよび/またはエステル清浄剤の調製プロセスであって、(a)第三級アミン官能基を持つ非四級化アミドおよび/またはエステル清浄剤と、(b)四級化剤とを反応させ;それにより四級化清浄剤を得ることを含む調製プロセスを提供する。
本発明の添加剤は、プロトン性溶媒の存在下で誘導してもよい。いくつかの実施形態では、これらの添加剤の調製に使用するプロセスは、メタノールを実質的に含まないか、または含まない。メタノールを実質的に含まないとは、反応混合物中のメタノールが0.5重量パーセント未満、0.1重量パーセント未満または0.05重量パーセント未満であることを意味することがあり、メタノールを完全に含まないことを意味することもある。
一実施形態では、本発明のプロセスは、四級化アミドおよび/またはエステル清浄剤を生成する。四級化清浄剤は、内燃機関および/または開放火炎バーナーに使用する燃料に使われる添加剤として使用してもよい。
上述の添加剤は、燃料組成物中の清浄剤として使用する以外に、潤滑油組成物中の分散剤型添加剤として使用してもよい。こうした潤滑組成物は、少量の、本明細書に記載の第四級アンモニウム塩、および大量の潤滑粘度の油を含んでいてもよい。添加剤が存在してもよい具体的なレベルについては、燃料組成物に関する上述のレベルと同じである。潤滑組成物は、上述の任意の追加添加剤をさらに含んでもよい。
ポリイソブチレンコハク酸無水物(500g)を、それ自体、数平均分子量1000の高分子ビニリデンポリイソブチレンと無水マレイン酸とを反応させて調製し、70℃に加熱し、スターラー、冷却器、サブラインの添加管に連結したフィードポンプ、窒素ライン、および熱電対/温度制御システムを備えたジャケット付き反応槽に仕込む。反応槽にヘプタン(76.9グラム)を加え、次いで反応温度を70℃に保持しながら、ジメチルアミノプロピルアミン(52.3g)を徐々に加える。添加が終了したら、反応槽を70℃で1時間保持する。得られる生成物、非四級化スクシンアミド清浄剤を冷却して集める。
ポリイソブチレンコハク酸無水物(100pbw)を、それ自体、数平均分子量1000の高分子ビニリデンポリイソブチレンと無水マレイン酸とを反応させて調製し、80℃に加熱し、スターラー、冷却器、サブラインの添加管に連結したフィードポンプ、窒素ライン、および熱電対/温度制御システムを備えたジャケット付き反応槽に仕込む。反応槽を100℃に加熱する。バッチ温度を120℃未満に維持しながら、反応物にジメチルアミノプロピルアミン(10.9pbw)を8時間の期間にわたって仕込む。次いで反応混合物を150℃に加熱し、温度で4時間維持する。得られる生成物、非四級化スクシンイミド清浄剤を冷却して集める。
本発明の好ましい実施形態によれば、例えば、以下が提供される。
(項1)
アミド基またはエステル基を含む第四級アンモニウム塩清浄剤を含む組成物であって、前記第四級化清浄剤は、
(a)非四級化清浄剤であって、アミド基またはエステル基を含み、第三級アミン官能基を持つ非四級化清浄剤;および
(b)四級化剤
の反応生成物を含む、組成物。
(項2)
(a)の前記非四級化清浄剤はアミド基を含み、前記第四級アンモニウム塩清浄剤は第四級アンモニウムアミド塩清浄剤である、上記項1に記載の組成物。
(項3)
(a)と(b)との前記反応中にプロトン性溶媒が存在し、(a)と(b)との前記反応は、前記清浄剤の構造に存在する任意の酸基以外に任意の追加酸成分を本質的に含まない、上記項1〜2のいずれかに記載の組成物。
(項4)
前記プロトン性溶媒は1〜10個の炭素原子を含む直鎖または分枝アルコールを含む、上記項3に記載の組成物。
(項5)
(a)の前記非四級化清浄剤は、ヒドロカルビル置換アシル化剤と、前記アシル化剤と縮合できる酸素または窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含む、上記項1〜4のいずれかに記載の組成物。
(項6)
前記ヒドロカルビル置換アシル化剤はポリイソブチレンコハク酸無水物を含む、上記項5に記載の組成物。
(項7)
前記アシル化剤と縮合できる酸素または窒素原子を持つ前記化合物は、1−アミノピペリジン、1−(2−アミノエチル)ピペリジン、1−(3−アミノプロピル)−2−ピペコリン、1−メチル−(4−メチルアミノ)ピペリジン、4−(1−ピロリジニル)ピペリジン、1−(2−アミノエチル)ピロリジン、2−(2−アミノエチル)−1−メチルピロリジン、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、N,N−ジブチル−1,3−ジアミノプロパン、N,N,N’−トリメチルエチレンジアミン、N,N−ジメチル−N’−エチルエチレンジアミン、N,N−ジエチル−N’−メチルエチレンジアミン、N,N,N’−トリエチルエチレンジアミン、N,N,N’−トリメチル−1,3−プロパンジアミン、N,N,2,2−テトラメチル−1,3−プロパンジアミン、2−アミノ−5−ジエチルアミノペンタン、N,N,N’,N’−テトラエチルジエチレントリアミン、3,3’−ジアミノ−N−メチルジプロピルアミン、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、トリエタノールアミン、N,N−ジメチルアミノプロパノール、N,N−ジエチルアミノプロパノール、N,N−ジエチルアミノブタノール、トリイソプロパノールアミン、1−[2−ヒドロキシエチル]ピペリジン、2−[2−(ジメチルアミン)エトキシ]−エタノール、N−エチルジエタノールアミン、N−メチルジエタノールアミン、N−ブチルジエタノールアミン、N,N−ジエチルアミノエタノール、N,N−ジメチルアミノエタノール、2−ジメチルアミノ−2−メチル−1−プロパノール、またはこれらの組み合わせを含む、上記項5〜6のいずれかに記載の組成物。
(項8)
前記アシル化剤と縮合できる酸素または窒素原子を持つ前記化合物は、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、またはこれらの組み合わせを含む、上記項5〜7のいずれかに記載の組成物。
(項9)
(b)の前記四級化剤はエチレンオキシド、プロピレンオキシド、ブチレンオキシド、スチレンオキシド、またはこれらの組み合わせを含む、上記項1〜8のいずれかに記載の組成物。
(項10)
上記項1〜9のいずれかに記載の組成物を含み、さらに燃料を含み、任意にさらに前記第四級アンモニウムアミド塩清浄剤以外の1種または複数種の燃料添加剤を含む、燃料組成物。
(項11)
内燃機関または開放火炎バーナーを運転する方法であって、前記機関またはバーナーに上記項10に記載の燃料組成物を供給することを含む、方法。
(項12)
第四級アンモニウム塩清浄剤の製造プロセスであって、
I. (a)非四級化清浄剤であって、アミド基またはエステル基を含み、第三級アミン官能基を持つ非四級化清浄剤を(b)四級化剤と反応させること;
それにより前記四級化分散剤を得ること;
を含み、
(a)と(b)との前記反応中にプロトン性溶媒が存在し、(a)と(b)との前記反応は、前記清浄剤の構造に存在する任意の酸基以外に任意の追加酸成分を含まない
プロセス。
(項13)
(a)の前記非四級化清浄剤は、ヒドロカルビル置換アシル化剤と、前記アシル化剤と縮合できる酸素または窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含む、上記項12に記載のプロセス。
(項14)
(b)の前記四級化剤は、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、スチレンオキシド、またはこれらの組み合わせを含む、上記項12〜13のいずれかに記載のプロセス。
(項15)
前記プロセスは、
II. (a)の前記混合物を約50℃〜約130℃の温度に加熱すること;
III. 前記反応が終了するまで保持すること;
それにより前記四級化分散剤を得ること
をさらに含む、上記項12〜14のいずれかに記載のプロセス。
Claims (12)
- 多くの量のアミド基を含む第四級アンモニウム塩清浄剤を含む組成物であって、前記第四級アンモニウム塩清浄剤は、
(a)非四級化清浄剤であって、多くの量のアミド基を含み、第三級アミン官能基を持つ非四級化清浄剤;および
(b)四級化剤
の反応生成物を含み、
ここで、(a)の前記非四級化清浄剤は、ヒドロカルビル置換ジカルボン酸アシル化剤と、前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含み、
前記ヒドロカルビル置換ジカルボン酸アシル化剤は、ポリオレフィンと、α,β−一価不飽和C 4 〜C 10 酸無水物との反応生成物であり、
前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物は、1−アミノピペリジン、1−(2−アミノエチル)ピペリジン、1−(3−アミノプロピル)−2−ピペコリン、1−メチル−(4−メチルアミノ)ピペリジン、4−(1−ピロリジニル)ピペリジン、1−(2−アミノエチル)ピロリジン、2−(2−アミノエチル)−1−メチルピロリジン、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、N,N−ジブチル−1,3−ジアミノプロパン、N,N,N’−トリメチルエチレンジアミン、N,N−ジメチル−N’−エチルエチレンジアミン、N,N−ジエチル−N’−メチルエチレンジアミン、N,N,N’−トリエチルエチレンジアミン、N,N,N’−トリメチル−1,3−プロパンジアミン、N,N,2,2−テトラメチル−1,3−プロパンジアミン、2−アミノ−5−ジエチルアミノペンタン、N,N,N’,N’−テトラエチルジエチレントリアミン、3,3’−ジアミノ−N−メチルジプロピルアミン、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、またはこれらの組み合わせを含む、
組成物。 - (a)と(b)との前記反応中にプロトン性溶媒が存在し、(a)と(b)との前記反応は、前記非四級化清浄剤の構造に存在する任意の酸基以外に任意の追加酸成分を本質的に含まない、請求項1に記載の組成物。
- 前記プロトン性溶媒は1〜10個の炭素原子を含む直鎖または分枝アルコールを含む、請求項2に記載の組成物。
- 前記ヒドロカルビル置換ジカルボン酸アシル化剤はポリイソブチレンコハク酸無水物である、請求項1〜3のいずれかに記載の組成物。
- 前記アシル化剤と縮合できる窒素原子を持つ前記化合物は、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、またはこれらの組み合わせを含む、請求項1〜4のいずれかに記載の組成物。
- (b)の前記四級化剤はエチレンオキシド、プロピレンオキシド、ブチレンオキシド、スチレンオキシド、またはこれらの組み合わせを含む、請求項1〜5のいずれかに記載の組成物。
- 請求項1〜6のいずれかに記載の組成物を含み、さらに燃料を含み、任意にさらに前記第四級アンモニウム塩清浄剤以外の1種または複数種の燃料添加剤を含む、燃料組成物。
- 内燃機関または開放火炎バーナーを運転する方法であって、前記機関またはバーナーに請求項7に記載の燃料組成物を供給することを含む、方法。
- 多くの量のアミド基を含有する第四級アンモニウム塩清浄剤の製造プロセスであって、
I. (a)非四級化清浄剤であって、多くの量のアミド基を含み、第三級アミン官能基を持つ非四級化清浄剤を(b)四級化剤と反応させること;
それにより前記第四級アンモニウム塩清浄剤を得ること;
を含み、
ここで、(a)の前記非四級化清浄剤は、ヒドロカルビル置換ジカルボン酸アシル化剤と、前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含み、
前記ヒドロカルビル置換ジカルボン酸アシル化剤は、ポリオレフィンと、α,β−一価不飽和C 4 〜C 10 酸無水物との反応生成物であり、
前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物は、1−アミノピペリジン、1−(2−アミノエチル)ピペリジン、1−(3−アミノプロピル)−2−ピペコリン、1−メチル−(4−メチルアミノ)ピペリジン、4−(1−ピロリジニル)ピペリジン、1−(2−アミノエチル)ピロリジン、2−(2−アミノエチル)−1−メチルピロリジン、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、N,N−ジブチル−1,3−ジアミノプロパン、N,N,N’−トリメチルエチレンジアミン、N,N−ジメチル−N’−エチルエチレンジアミン、N,N−ジエチル−N’−メチルエチレンジアミン、N,N,N’−トリエチルエチレンジアミン、N,N,N’−トリメチル−1,3−プロパンジアミン、N,N,2,2−テトラメチル−1,3−プロパンジアミン、2−アミノ−5−ジエチルアミノペンタン、N,N,N’,N’−テトラエチルジエチレントリアミン、3,3’−ジアミノ−N−メチルジプロピルアミン、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、またはこれらの組み合わせを含み、
(a)と(b)との前記反応中にプロトン性溶媒が存在し、(a)と(b)との前記反応は、前記非四級化清浄剤の構造に存在する任意の酸基以外に任意の追加酸成分を含まない
プロセス。 - (b)の前記四級化剤は、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、スチレンオキシド、またはこれらの組み合わせを含む、請求項9に記載のプロセス。
- 前記プロセスは、
II. (a)の前記混合物を約50℃〜約130℃の温度に加熱すること;
III. 前記反応が終了するまで保持すること;
それにより前記第四級アンモニウム塩清浄剤を得ること
をさらに含む、請求項9または10のいずれかに記載のプロセス。 - 多くの量のアミド基を含む第四級アンモニウム塩清浄剤を含む組成物であって、前記第四級アンモニウム塩清浄剤は、プロトン性溶媒の存在下での以下:
(a)非四級化清浄剤であって、多くの量のアミドを含み、第三級アミン官能基を持つ非四級化清浄剤;および
(b)四級化剤
の反応生成物を含み、
ここで、(a)の前記非四級化清浄剤は、ヒドロカルビル置換ジカルボン酸アシル化剤と、前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物との縮合生成物を含み、
前記ヒドロカルビル置換ジカルボン酸アシル化剤は、ポリオレフィンと、α,β−一価不飽和C 4 〜C 10 酸無水物との反応生成物であり、
前記アシル化剤と縮合できる窒素原子を持ち、さらに少なくとも1つの第三級アミノ基を持つ化合物は、1−アミノピペリジン、1−(2−アミノエチル)ピペリジン、1−(3−アミノプロピル)−2−ピペコリン、1−メチル−(4−メチルアミノ)ピペリジン、4−(1−ピロリジニル)ピペリジン、1−(2−アミノエチル)ピロリジン、2−(2−アミノエチル)−1−メチルピロリジン、N,N−ジエチルエチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジブチルエチレンジアミン、N,N−ジメチル−1,3−ジアミノプロパン、N,N−ジエチル−1,3−ジアミノプロパン、N,N−ジブチル−1,3−ジアミノプロパン、N,N,N’−トリメチルエチレンジアミン、N,N−ジメチル−N’−エチルエチレンジアミン、N,N−ジエチル−N’−メチルエチレンジアミン、N,N,N’−トリエチルエチレンジアミン、N,N,N’−トリメチル−1,3−プロパンジアミン、N,N,2,2−テトラメチル−1,3−プロパンジアミン、2−アミノ−5−ジエチルアミノペンタン、N,N,N’,N’−テトラエチルジエチレントリアミン、3,3’−ジアミノ−N−メチルジプロピルアミン、3,3’−イミノビス(N,N−ジメチルプロピルアミン)、またはこれらの組み合わせを含む、
組成物。
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