GB2121808A - Cloud-point-lowering copolymer additives for fuel compositions - Google Patents
Cloud-point-lowering copolymer additives for fuel compositions Download PDFInfo
- Publication number
- GB2121808A GB2121808A GB08315552A GB8315552A GB2121808A GB 2121808 A GB2121808 A GB 2121808A GB 08315552 A GB08315552 A GB 08315552A GB 8315552 A GB8315552 A GB 8315552A GB 2121808 A GB2121808 A GB 2121808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- dicarboxylic
- unsaturated
- radical
- formula
- 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.)
- Granted
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims description 13
- 239000000654 additive Substances 0.000 title description 23
- 239000000446 fuel Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- -1 primary amine compounds Chemical class 0.000 claims abstract description 23
- 239000007789 gas Substances 0.000 claims abstract description 14
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 6
- 150000005690 diesters Chemical class 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 5
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 16
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 5
- 230000001151 other effect Effects 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000013078 crystal Substances 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 3
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- FOGXVHIVRBKOQG-UHFFFAOYSA-N n',n'-didodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCN(CCCN)CCCCCCCCCCCC FOGXVHIVRBKOQG-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SWVSKCPPMNGBGL-UHFFFAOYSA-N 10-aminodecan-1-ol Chemical compound NCCCCCCCCCCO SWVSKCPPMNGBGL-UHFFFAOYSA-N 0.000 description 1
- QCSCNTGILDKNRW-UHFFFAOYSA-N 11-aminoundecan-1-ol Chemical compound NCCCCCCCCCCCO QCSCNTGILDKNRW-UHFFFAOYSA-N 0.000 description 1
- PPMMRVOODATNRT-UHFFFAOYSA-N 13-aminotridecan-1-ol Chemical compound NCCCCCCCCCCCCCO PPMMRVOODATNRT-UHFFFAOYSA-N 0.000 description 1
- FAGQNUXPKGWBBI-UHFFFAOYSA-N 14-aminotetradecan-1-ol Chemical compound NCCCCCCCCCCCCCCO FAGQNUXPKGWBBI-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- ULAXUFGARZZKTK-UHFFFAOYSA-N 2-aminopentan-1-ol Chemical compound CCCC(N)CO ULAXUFGARZZKTK-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- QCCRZABDWHPVCI-UHFFFAOYSA-N 3-(2,4,6-trimethyldecoxy)propan-1-amine Chemical compound CCCCC(C)CC(C)CC(C)COCCCN QCCRZABDWHPVCI-UHFFFAOYSA-N 0.000 description 1
- TWXCJZHSMRBNGO-UHFFFAOYSA-N 3-decoxypropan-1-amine Chemical compound CCCCCCCCCCOCCCN TWXCJZHSMRBNGO-UHFFFAOYSA-N 0.000 description 1
- AGFZAZKFCMPYGS-UHFFFAOYSA-N 3-docosoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCCCN AGFZAZKFCMPYGS-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- HPIKNEFNXLGDDK-UHFFFAOYSA-N 3-hexadecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCOCCCN HPIKNEFNXLGDDK-UHFFFAOYSA-N 0.000 description 1
- RESBJBYIDKHFGE-UHFFFAOYSA-N 3-icosoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCOCCCN RESBJBYIDKHFGE-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- RDCAZFAKCIEASQ-UHFFFAOYSA-N 3-octoxypropan-1-amine Chemical compound CCCCCCCCOCCCN RDCAZFAKCIEASQ-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- YUUFAJOXLZUDJG-UHFFFAOYSA-N 4-methoxybutan-1-amine Chemical compound COCCCCN YUUFAJOXLZUDJG-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- FGUVIEZMWVLUBS-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-(2-iodo-5-methoxyphenyl)sulfanylpurin-6-amine Chemical compound COC1=CC=C(I)C(SC=2N(C3=NC=NC(N)=C3N=2)CCNCC(C)(C)C)=C1 FGUVIEZMWVLUBS-UHFFFAOYSA-N 0.000 description 1
- VNMOWKHAHQJUJI-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-(2-iodo-5-methoxyphenyl)sulfanylpurin-6-amine Chemical compound COC1=CC=C(I)C(SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=C1 VNMOWKHAHQJUJI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000112 cooling gas Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- FJXVASQTCNSEID-UHFFFAOYSA-N n',n'-di(tetradecyl)propane-1,3-diamine Chemical compound CCCCCCCCCCCCCCN(CCCN)CCCCCCCCCCCCCC FJXVASQTCNSEID-UHFFFAOYSA-N 0.000 description 1
- JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- FDBKCXQMGWOXCF-UHFFFAOYSA-N n',n'-dioctadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCN(CCCN)CCCCCCCCCCCCCCCCCC FDBKCXQMGWOXCF-UHFFFAOYSA-N 0.000 description 1
- ZINLVDIYZWIFLG-UHFFFAOYSA-N n',n'-dioctylpropane-1,3-diamine Chemical compound CCCCCCCCN(CCCN)CCCCCCCC ZINLVDIYZWIFLG-UHFFFAOYSA-N 0.000 description 1
- HRWWZALMBMPXTI-UHFFFAOYSA-N n'-(3-decoxypropyl)propane-1,3-diamine Chemical compound CCCCCCCCCCOCCCNCCCN HRWWZALMBMPXTI-UHFFFAOYSA-N 0.000 description 1
- HLDPTEWDRAWMRM-UHFFFAOYSA-N n'-[3-(2,4,6-trimethyldecoxy)propyl]propane-1,3-diamine Chemical compound CCCCC(C)CC(C)CC(C)COCCCNCCCN HLDPTEWDRAWMRM-UHFFFAOYSA-N 0.000 description 1
- BIWCZXIHIQDFSM-UHFFFAOYSA-N n'-docosylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNCCCN BIWCZXIHIQDFSM-UHFFFAOYSA-N 0.000 description 1
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 1
- UKNVXIMLHBKVAE-UHFFFAOYSA-N n'-hexadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCNCCCN UKNVXIMLHBKVAE-UHFFFAOYSA-N 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- SSSZZOVUXFLWCQ-UHFFFAOYSA-N n'-tetradecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCNCCCN SSSZZOVUXFLWCQ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
-
- 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
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Novel polymeric compounds having a number-average molecular weight in the range 2000 to 10,000 are produced by the condensation of one or more primary amine compounds of formula R-Z[-(CH2)n-NH-]m-H (I> and/or HO-CH2-R''-NH2 (II> where, in formula (I), R represents a univalent saturated C1-30 aliphatic radical, Z is an oxygen atom, an imino group or a bivalent group =NR', in which R' is a univalent C1-30 aliphatic radical, preferably straight chain and preferably containing from 12 to 24 carbon atoms; n is 2, 3 or 4 and m is 0, 1, 2, 3 or 4, provided that m is not 0 unless Z is imino; and, in Formula II, R'' is a bivalent saturated C1-18 aliphatic radical, preferably straight-chain, on a copolymer formed between: (A) vinyl acetate, and (B) at least one unsaturated alpha , beta - dicarboxylic compound that may be a dicarboxylic acid, a diester of such an acid or an anhydride. Alternatively, such copolymers may be prepared by pre-reacting (B) with the amino compound and then polymerising the product with vinyl acetate. Such compounds are added to middle hydrocarbon distillates, especially gas oils, to lower their cloud point. The compounds also have other effects on such distillates.
Description
SPECIFICATION
Cloud-point-lowering copolymers and compositions containing them
This invention relatesto the lowering of the cloud point of middle hydrocarbon distillates.
Novel nitrogen-bearing additives useful as agents for lowering the cloud pointofthe middle hydrocarbon distillates have now been discovered. They are described in more detail below, and constitute one embodiment ofthe present invention.
The petroleum distillates with which the present invention is concerned are middle distillates (fuel oils and gas oils) whose distillation range (standard ASTM
D 86-67) is between 1 500C and 450"C. The gas oils, which are more particularly considered herein, have a distillation range from an initial temperature in the range 160"C to 190"C, to a final temperature in the range350 Cto 390 C.
There are, on the market, a large number of substances intended to improve the filterability limit temperature and the pour point of paraffin-rich petroleum cuts, such as long-chain olefin-base polymers, or-olefin-base copolymers, ethylene-(vinyl acetate) copolymers, N-acylaminoethylesters of polymers containing acids, and halocarbon compounds.
Such substances act on the kinetic crystallisation phenomena and modify the size of the crystals, enabling the suspension to be used ata lower temperature without clogging passages and filters.
The above-mentioned substances do not modify the temperature at which the first paraffin crystals appear.
In fact, it was considered hitherto thatthattemperaturn was a factor that depends on the molecular weight and the formula ofthe paraffins and the nature ofthe solvent.
A reduction in the cloud point of middle distillates (in particular gas oils) by means of an additive would be a consideration of substantial attraction from the point of view of refiners as, without modifying the distillation system, itwould make it possible to comply with the specifications which at the present time are developing in the direction of increasing severity.
The present invention provides polymericcompounds having a number-average molecularweightin the rage 2000 to 10,000 and resulting from the condensation of one or more primary amine com pounds offormula
R - Z - [- (CH2)n - NH ~]m - H (I) and/or HO - CH2 - R" - NH2 (II) where, in formula (I), R represents a univalent saturated C1-30 aliphatic radical, Z is an oxygen atom, an imino group ora bivalentgroup =NR', in which R' is a u nivalent C130 aliphatic radical, preferably straight chain and preferably containing from 12 to 24 carbon atoms; n is 2,3or4and mis 0,1, 2,3or4, provided that mis not 0 unless Z is imino; and, Formula II, R" is a bivalent saturated C118 aliphatic radical, preferably straight-chain, on a copolymerformed between (A) vinyl acetate, and (B) at least one unsaturated os,ss-dicarboxyiic compound that may be a dicarboxy licacid, a diesterofsuch an acid or an anhydride.
It has been found that compounds ofthe present invention, when added to middle distillates, allow the first paraffin crystals to appear only at a lower temperature than thetemperature at which such crystals would appear without such additives. This is all the more surprising in that the property is retained after a number of heating and cooling cycles and is revealed by a mechanism that is as yet unexplained.
Compounds of the present invention also have an effect on other properties ofthe middle distallates, in particular gas oils, by modifying the performance of the medium that contains the precipitated paraffins.
Thus, compounds ofthe present invention have a substantial action on the filterability limit temperature and the pour point.
When the paraffin crystals which are caused to form by the cooling operation have appeared, their natural tendency is to gravitate to the bottom where they accumulate. That phenomenon, which is generally referred to as sedimentation, causes clogging of passages and filters and is prejudicial to satisfactory use of middle distillates and in particular gas oils.
Compounds of the present invention are capable of substantially reducing the rate of sedimentation ofthe paraffinsformed by cooling gas oils and other middle distillates.
Finally, compounds of the invention can also inhibit corrosion of metal surfaces bythe gas oils and other middle distillates to which they are added.
In theforegoing definition ofthe compounds ofthe invention, the proportions of the units corresponding to monomers (A) and (B) are preferably in the vicinity of 50%-50%, in which casethe units corresponding to the monomers (A) and (B) are distributed alternately in the copolymer.
The unsaturated oc,-dicarboxylic compound (B) may be maleic acid, an alkylmaleic acid (in particular methyl maleic or citraconic acid), an alkyl diester of the said acids (in particular a methyl, ethyl or propyl diester) ora corresponding anhydride. In accordance with the invention, anhydrides are preferred, more particularly maleic anhydride.
The compounds offormula (I) above may be primary amines havingtheformula R-NH2 (in that case, in formula (I), Z represents imino and mis zero).
Preferably, the radical R is a straight-chain C12-24 radical. The following may be mentioned as specific examples of such amines: dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine and docosylamine.
The compounds offormula (I) may also be polyamines derived from saturated aliphatic amines and corresponding to the formula:
R - NH - [- (CH2)n - NH ]m - H which corresponds to general formula (I) in which Z is imino, mis from 1 to 4 and n is from 2 to 4, preferably 3.
Preferably, R is a C12-24 straight chain. Specific compounds include N - dodecyl -1,3 - diaminopropane, N -tetradecyl - 1,3-diaminopropane, N hexadecyl - 1,3 - diaminopropane, N - octadecyl - 1,3 - diaminopropane, N - eicoysl - 1,3 - diaminopropane, N - docosyl -1,3 - diaminopropane, N - hexadecyl
dipropylenetriamine, N - octadecyl - dipropy
lenetriamine, N - eicosyl - dipropylenetriamine and N
docosyl - dipropylenetriamine.
The compounds offormula (I) may also be polyamines ofthe following formula: R' - N - [- (CH2)n - NH i m - H which corresponds to general formula (I) in which Z represents =NR' and each of R and R',whichare identical or different, is a C1-24 alkyl radical, preferably containing fron 8to 24 carbon atoms, and R and R' together preferably contain from 16 to 32 carbon atoms; n is from 2to 4and mis from 1 to 4.The following may be mentioned as specific compounds: N,N - diethyl -1,2 - diaminoethane, N,N - diisopropyl 1,2-diaminoethane, N,N -dibutyl - 1,2-diami- noethane, N,N - diethyl -1,4 - diaminobutane, N,N dimethyl - 1,3 - diaminopropane, N,N - diethyl -1,3 - diaminopropane, N,N - dioctyl - 1,3 - diaminopropane, N,N -didecyl - diaminopropane, N,N -didodecyl - 1,3 - diaminopropane, N,N - ditetradecyl - 1,3- diaminopropane, N,N -dihexadecyl - 1,3-diaminopro- pane, N,N - dioctadecyl -1,3 - diaminopropane, N,N didodecyl - dipropylenetriamine, N,N - ditetradecyl dipropylenetriamine, N,N - dihexadecyl - dipropylenetriamine and N,N - dioctadecyl - dipropylenetriamine.
Finally, the compounds of formula (I) may be ethers ofaminesofthefollowingformula: 90- (CH2)n - NH ]m - H which corresponds to the general formula (I) in which
Z is an oxygen atom. R preferablycontainsfrom 12to 24 carbon atoms, m is an integeroffrom 1 to 4and n is a integeroffrom 2to4, preferably2 or3.
The following may be quoted as specific ether amines; 2-methoxyethylamine, 3-methoxypropylamine, 4-methoxybutylamine, 3-ethoxypropylamine, 3-octyloxypropylamine, 3-decyloxypropylamine, 3hexadecyloxypropylamine, 3-eicosyloxypropylamine, 3-docosyloxypropylamine, N-(3- octyloxypropyl)-1,3 : - diaminopropane, N - (3 - decyloxypropyl) - 1,3 diaminopropane, 3 - (2,4,6 -trimethyldecyloxy) propylamine, and N - [3 - (2,4,6 - trimethyldecyloxy) - propyl]1,3-diaminopropane.
The following may be mentioned as specific examples ofthe amino-alcohol ofthe general formula (ill): monoethanoline, 1 aminopropan - 3 - ol, 1 - aminobutan-4-ol, 1 -aminopentan -5-ol, 1 -aminohexan - 6- ol, 1 -aminoheptan -7-oIl -aminooctan-8-ol, 1 aminodecan - 10 - ol, 1 - aminoundecan - 11 - ol, 1 aminotridecan - 13 - ol, 1 - aminotetradecan -14 - ol, 1 aminohexadecan 16-ol,2-amino-2-methyl propan -1 -ol, 2-aminobutan -1 -ol and 2-aminopentan -1 ol.
Preparation ofthe additives according to the invention generally comprises two stages: preparation of the vinyl acetate - oc,P - dicarboxylic monomer
copolymer, followed by condensation on the polymer formed of at least one compound offormula (I) and/or (II).
Preparation of the base copolymers is effected in the
first stage by conventional methods of polymerization
by a free-radical process, for example in the presence of a starter ofthe azobisisobutyronitrile or peroxide
(such as lauroyl peroxide) type, in solution in a
hydrocarbon solvent such as cyclohexane, isooctane, dodecane, bezene, toluene, xylene or diisopropylbenzene, or in solution in tetrahydrofuran or dioxan. Itwill be advantageous to use hydrocarbon cuts having a relatively high boiling temperature such as a kerosene ora gas oil.
The amounts ofsolvent used will usually be such thatthe concentration by weight of dry matter is in the range 25 to 70% and preferably in the vinicity of 50%.
The copolymerisation reaction in the presence of a free-radical-forming stalPer, is performed at a temper- ature in the range 40 to 1 000C, preferably 50 to 70"C.
Depending on the operating conditions, the reaction may lastforfrom 2to 10 hour?n most cases from 3 to 5 hours. The result is a solution of copolymer, in the form of a viscous liquid.
For preparation ofthe additives according to the invention, the second stage comprises condensing the compound offormula (I) or (II) on the copolymer formed in thefirststage by any usual method.
In general, the compound(s) offormula (I) and/or (Il) is/are added to the copolymer solution produced as described above, in a molar proportion that substan tially corresponds to the proportion of unsaturated diacid, diester or an hydride used in preparing the copolymer. That proportion may be for example from 0.9 to 1.1 moles of compound offormula (I) and/or (II) per mole of dicarboxylic compound. It is also possible to envisage a more substantial deficit in respect of the compound offormula (I) and/or (11). It is then possible to use a proportion which is as small for example as 0.5 mole per mole of dicarboxylic compound used in the copolymer.
The reaction is performed by heating the mixture at a temperature in the range 75 to 130"C, preferably 80 to 1 00'C, the duration ofthe reaction being from 1 to 6 hours, with a duration of about 2 hours usually being sufficient. The reaction ofthe substances offormula (I) and/or (II) on the units (B) ofthe copolymer gives rise to imide (succinimide) groups accompanied by the formation ofwater or alcohol, depending whether the dicarboxylic units (B) are diacid, an hydride or diester groups. If desired, the volatile substances formed may be removed from the reaction mixture, either by entrainmentwith an inertgassuch as nitrogen or argon, or by azeotropic distillation with a selected solvent.
Certain ofthe additives according to the invention may be synthesized by effecting radical copolymeriza tion of vinyl acetate and N-substituted maleimides, the latter being produced by preliminary reaction of the compound(s) offormula (I) and/or (II) on maleic anhydride or one of its above-mentioned derivatives.
The additives are produced in solution in the selected solvent and. may be used in that form directly in the middle petroleum distillateswhose cloud point isto be improved.
Although the mechanism by which the compounds
ofthe present invention act on the temperature at which paraffin crystals appear in the middle distillate
has not yet been clearly ascertained, a marked
improvement in the cloud point of the middle distillates when treated by such compounds is observed when the are added in concentrations ranging forexamplefrom 0.001 to 1% by weight and preferablyfrom 0.01 to 0.2% by weight. The reduction in the cloud point may be up to 4K or in some cases even more.
A remarkablefactto be noted is that additives ofthe present invention also have the property of inhibiting sedimentation of n-paraffins in middle distillates in a rest condition, improving the filtrability limittempera ture and the pour temperature, and inhibitiing corrosion of metal surfaces in contact with such distillates.
The following examples illustrate but do not limit the invention.
EXAMPLE 1
Step a
Using a reaction vessel ofthermostatically controlled double jacket type with a capacity of 1 litre and provided with an efficient mechanical agitator system, 43 g (0.5 mol) ofvinyl acetate, 49 g (0.5 mol) of maleic anhydride, 350 ml oftoluene and 2.8 g of azobisisobutyronitrile are introduced into the reaction vessel.
The agitated mixture is heated for 6 hours at a temperature of 70 C, and the resulting copolymer is filtered off, rinsed with toluene and then dried under vacuum at800C.
Stepb
To the resulting 18.4 g of the copolymer is added 14 g (that isto say, 0.05 mol equivalent of primary amine) of a commercial mixture of fatty amines containing approximately 1% of C14 amine, 28% of C16 amine and 71% of C18 amine. Heptane is added so thatthe percentage of dry matter is close to 60%,then the mixture is heated under refluxfor3 hours to produce additive A in solution in heptane. The concentration of final product is adjusted to 50% by weight.
EXAMPLE2
Additive B is prepared under identical conditions to those described in Step bin Example 1 from 9.2 g of the copolymer prepared in Stepaof Example 1, and 8.1 g (that is to say, 0.027 mol equivalent of primary amine) of a mixture of primary amines having fatty chains, comprising approximately 1% of C14 amine, 5% of C16 amine, 42% of C18 amine, 12% ofC20 amine and 40% of C22 amine.
EXAMPLE3
Additive C is produced under conditions similarto those described in Step b of Example 1 bythe condensation of 16.96 g, i.e. 0.053 mol equivalent of primary amine, of a mixture of fatty amines of a composition comprising 5% of C16 amine, 15% of C18 amine, 40% of C20 amine and 40% of C22 amine, on 18.4g of copolymer produced in accordance with
Example 1 Step a.
EXAMPLES 4 to 6
These Examples use a copolymer produced in accordance with Example 1 Step a and, using the mode of operation described in Example 1 Step b, condensation is effected in respect of the following, observing the molar proportions set out in Example 1
Step babove: Example 4:3 - - (2,4,6 -trimethyldecyl)oxy propyla- mine, which gives additive D.
Example 5: 1 - aminohexadecan -16 ol, which gives additive E.
Example 6: N,N-didodecyl 1,3-diaminopropane, which gives additive F.
Additives I to Ill are used in the form of solutions
containing 50% ofdrymatterinheptane,while additives IV to VI are used in the form of solutions of the same content in toluene.
The degree of activity of the additives described in these Examples was tested on two cuts of gas oils of
ARAMCO origin, which are referred to, hereinafter as
G1 and G2 and the characteristics of which are set out in Table I below: TABLE I
ASTM distillation % distilled Density at 15 Gas oils I.P.( C) F.P.( C) at 350 C in kg/l G1 181 382 89 0.846 Go 186 385 87 0.847 AdditivesAto Fwere incorporated, in a proportion of 0.1% by weight, in the above-described gas oil cuts G1andG2.
For each of the compositions which were formed in thatway,three parameters were determined:
the cloud point, using the AFNOR T 60-105 method:
thefiltrability limittemperature (FLT) using the
AFNOR M 07-042 method; and
the pour point, using the AFNOR T 60-105 method.
The results ofthose measurement operations are set out in Table II below:
TABLE n
Cloud point ( C) F.L.T. ( C) Pour point ( C) Additives G1 G2 G1 G2 G1 G2 without + 2 + 6 0 + 3 - 6 - 3 0.1% A - 1 + 2 - 4 0 - 12 - 15 0.1% B 0 + 3 - 4 0 - 9 - 9 0.1% C - 1 + 2 - 3 - 1 - 12 - 12 0.1% D 0 + 3 - 3 0 - 9 - 9 0.1% E -1 + 2 - 3 - 1 - 12 - 9 0.1% F - 1 + 2 - 4 - 1 - 12 - 9 EXAMPLE 7
This Example involves testing the anti-corrosion effect of additive A of Example 1.
This additive was used in the two gas oils G1 and G2 already described above in a level of concentration of 0.01% by weight.
The corrosion test involved studying corrosion due to artificial sea water on cylindrical testpieces of polished iron orsteel, in accordancewiththe standardASTM D 665, modified in that the temperature was 32.2 C and the period of time 20 hours.
The two gas oils G1 and G2without additive gave testpieces which are 100% rusted on their surface, whilethetwo gas oils containing 0.01% by weight of additive A gave intact testpieces with 0% rust.
Claims (16)
1. Polymericcompounds having a number-average molecularweight in the range 2000 to 10,000 and resulting from the condensation of one or more primary amine compounds offormula
R - Z - [ - (CH2)n - NH - ]m - H (I) (I)
and/or HO - CH2 - R" - NH2 (II) where, in formula (I), R represents a univalent saturated C 30 aliphatic radical, Z is an oxygen atom, an imino group or a bivalent group =NR', in which R' is a univalentC1 aliphatic radical; n is 2,3 or4and m is 1,2,3or4, provided that m is not 0 unlessZis imino; and, in Formula II, R" is a bivalentsaturated C1-18 aliphatic radical, on a copolymerformed between: (A) vinyl acetate, and (B) at lest one unsaturated ,ss-dicarboxylic com
pound that may be a dicarboxylic acid, a diester of such an acid or an anhydride.
2. Acompound according to Claim 1 containing approximately 50 molar % of units (A) and approximately 50 molar % of units (B).
3. A compound according to Claim 1 or2inwhich the unsaturated os,ss-dicarboxylic compound from which the units (B) originate comprises at least one maleicoralkylmaleicacid, a methyl, ethyl orpropyl diester of such an acid, or a maleic or alkylmaleic anhydride.
4. A compound according to any one of Claims 1 to 3 in which the amine compound (I) comprises at least one straight-chain C12-24 primary monoamine.
5. Acompound according to any one of Claims 1 to 3 in which the amine compound (I) comprises at least one polyamine oftheformula: 9 - NH - [- (CH2)n - NH im - H in which R represents a straight-chain C12-24 alkyl radical,nis2,3or4andmisl,2,3or4.
6. A compound according to any one of Claims 1 to 3 in which the amine compound (I) comprises at least one polyamine having the formula:
R - NR' - [ - (CH2)n - NH ]mH in which each of Rand R' represents a straight-chain C824alkyl radical and R and R' together contain from l6to32carbonatoms,nis2,3or4andmisl,2,3or4.
7. Acompound according to any one of Claims 1
to 3 in which the amine compound (I) comprises at
least one ether amine having the following formula: R - O - [ - (CH2)n - NH im - H in which R represents a C12-24 alkyl radical, n is 2,3 or4 and m is 1, 2, 3 or 4.
8. A compound according to any one of Claims 1
to 3 in which the amine compound (II) comprises at
least one amino alcohol having the following for
mula: HO - CH2 - R"- NH2 in which R" represents a straight-chain C1-18 alkylene
radical.
9. Acompound according to any one of Claims 1
to 8 produced by the radical copolymerisation of
suitable proportions of vinyl acetate and at least one
ofthe said unsaturated a,ss-dicarboxylic compounds;
followed bythe condensation, on the copolymer
formed, of at least one compound offormula (I) and (II) in a proportion of at least 0.5 mole per mole of
unsaturated a,ss-dicarboxyliccompound used.
10. A compound according to Claim 9 in which the
proportion ofthe compound offormula (I) or(ll) is
from 0.9 to 1.1 mole per mole of unsaturated cx,P-dicarboxylic compound used.
11. A compound according to any one of Claims 1
to 8 produced by the radical copolymerisation of
suitable proportions of vinyl acetate and at least one
unsaturated a,ss-dicarboxylic compound, comprising
at least one N-substituted imide produced by pre
liminary reaction of an unsaturated a,ssi-dicarboxylic compound with at least one compound offormula (I)
or (II).
12. A compound according to Claim 1 substantial
ly as hereinbefore described in any one of Examples 1
to6.
13. A middle distillate composition comprising
major proportion of middle distillate having a distilla
tion range between 150 and 450 C and a minor
proportion, sufficientto reduce its cloud point of at
least one compound according to any one of Claims 1
to12.
14. Acomposition according to Claim 13 in which
the middle distillate comprises a gas oil cut having a
distillation rangefrom an initial temperature of 160 to 1900Cto a final temperature of 350 to 390 C.
15. A middle distillate composition according to
Claim 13 or 14 in which the proportion of the
compound according to anyone of Claims 1 to 12 is
from 0.001 to 1% weight.
16. A composition according to Claim 15 in which
the proportion ofthesaid compound is from 0.01% to
0.2% by weight
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8210088A FR2528051B1 (en) | 1982-06-08 | 1982-06-08 | NITROGEN ADDITIVES FOR USE AS DISORDERS TO REDUCE THE POINT OF MEDIUM HYDROCARBON DISTILLATES AND COMPOSITIONS OF MEDIUM HYDROCARBON DISTILLATES CONTAINING THE ADDITIVES |
Publications (3)
Publication Number | Publication Date |
---|---|
GB8315552D0 GB8315552D0 (en) | 1983-07-13 |
GB2121808A true GB2121808A (en) | 1984-01-04 |
GB2121808B GB2121808B (en) | 1986-03-12 |
Family
ID=9274836
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB08315552A Expired GB2121808B (en) | 1982-06-08 | 1983-06-07 | Cloud-point-lowering copolymer additives for fuel compositions |
Country Status (5)
Country | Link |
---|---|
DE (1) | DE3320720A1 (en) |
FR (1) | FR2528051B1 (en) |
GB (1) | GB2121808B (en) |
IT (1) | IT1185501B (en) |
NL (1) | NL189818C (en) |
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FR3125298A1 (en) | 2021-07-19 | 2023-01-20 | Totalenergies Marketing Services | Use of an additive composition to reduce emissions from diesel vehicles |
FR3144623A1 (en) | 2022-12-30 | 2024-07-05 | Totalenergies Onetech | Fuel additive composition comprising at least one secondary arylamine and at least one nitroxide |
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GB1025795A (en) * | 1962-10-18 | 1966-04-14 | Exxon Research Engineering Co | Improvements in lubricating oil compositions |
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GB1084557A (en) * | 1964-10-30 | 1967-09-27 | Monsanto Co | Flocculating materials and use thereof |
GB1092965A (en) * | 1965-05-14 | 1967-11-29 | Bayer Ag | Process for the dyeing of chrome leather |
FR2471405A1 (en) * | 1979-12-13 | 1981-06-19 | Inst Francais Du Petrole | Terpolymer from acrylic! ester, di:isobutylene! - and di:carboxylic acid deriv., as low temp. flow improver for hydrocarbon oils |
GB2065676A (en) * | 1979-12-13 | 1981-07-01 | Inst Francais Du Petrole | Terpolymers and their manufacture and use as additives foroil |
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FR1342117A (en) * | 1961-07-25 | 1963-11-08 | Bayer Ag | Iron (iii) gamma oxide and process for its preparation |
US3974267A (en) * | 1975-04-24 | 1976-08-10 | Cities Service Company | Manufacture of iron oxides |
US4210424A (en) * | 1978-11-03 | 1980-07-01 | Exxon Research & Engineering Co. | Combination of ethylene polymer, normal paraffinic wax and nitrogen containing compound (stabilized, if desired, with one or more compatibility additives) to improve cold flow properties of distillate fuel oils |
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- 1982-06-08 FR FR8210088A patent/FR2528051B1/en not_active Expired
-
1983
- 1983-06-06 NL NLAANVRAGE8302012,A patent/NL189818C/en not_active IP Right Cessation
- 1983-06-06 IT IT21470/83A patent/IT1185501B/en active
- 1983-06-07 GB GB08315552A patent/GB2121808B/en not_active Expired
- 1983-06-08 DE DE19833320720 patent/DE3320720A1/en active Granted
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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GB846508A (en) * | 1957-12-20 | 1960-08-31 | Exxon Research Engineering Co | A process for producing oil additives |
GB1025795A (en) * | 1962-10-18 | 1966-04-14 | Exxon Research Engineering Co | Improvements in lubricating oil compositions |
GB1077956A (en) * | 1963-07-22 | 1967-08-02 | Ici Ltd | Vinyl acetate copolymers |
GB1084557A (en) * | 1964-10-30 | 1967-09-27 | Monsanto Co | Flocculating materials and use thereof |
GB1092965A (en) * | 1965-05-14 | 1967-11-29 | Bayer Ag | Process for the dyeing of chrome leather |
FR2471405A1 (en) * | 1979-12-13 | 1981-06-19 | Inst Francais Du Petrole | Terpolymer from acrylic! ester, di:isobutylene! - and di:carboxylic acid deriv., as low temp. flow improver for hydrocarbon oils |
GB2065676A (en) * | 1979-12-13 | 1981-07-01 | Inst Francais Du Petrole | Terpolymers and their manufacture and use as additives foroil |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5814110A (en) * | 1986-09-24 | 1998-09-29 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
GB2197877A (en) * | 1986-10-07 | 1988-06-02 | Exxon Chemical Patents Inc | Additives for wax containing distillated fuel |
GB2197878A (en) * | 1986-10-07 | 1988-06-02 | Exxon Chemical Patents Inc | Middle distillate compositions with reduced wax crystal size |
US9169452B2 (en) | 2010-12-23 | 2015-10-27 | Total Raffinage Marketing | Modified alkyl-phenol-aldehyde resins, use thereof as additives for improving the properties of liquid hydrocarbon fuels in cold conditions |
US9657250B2 (en) | 2010-12-23 | 2017-05-23 | Total Raffinage Marketing | Modified alkyl-phenol-aldehyde resins, use thereof as additives for improving the properties of liquid hydrocarbon fuels in cold conditions |
US10167435B2 (en) | 2011-02-08 | 2019-01-01 | Total Marketing Services | Liquid compositions for marking liquid hydrocarbon motor fuels and other fuels, motor fuels and other fuels containing them and process for detecting the markers |
US10081773B2 (en) | 2011-07-12 | 2018-09-25 | Total Marketing Services | Additive compositions that improve the stability and the engine performances of diesel fuels |
US10538714B2 (en) | 2011-07-12 | 2020-01-21 | Total Marketing Services | Additive compositions that improve the stability and the engine performances of diesel fuels |
US9587193B2 (en) | 2012-02-17 | 2017-03-07 | Total Marketing Services | Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels |
US9534183B2 (en) | 2012-06-19 | 2017-01-03 | Total Marketing Services | Additive compositions and use thereof for improving the cold properties of fuels and combustibles |
US10767128B2 (en) | 2016-07-21 | 2020-09-08 | Total Marketing Services | Copolymer suitable for use as a detergent additive for fuel |
US10767126B2 (en) | 2016-10-21 | 2020-09-08 | Total Marketing Services | Combination of fuel additives |
Also Published As
Publication number | Publication date |
---|---|
IT8321470A0 (en) | 1983-06-06 |
NL189818B (en) | 1993-03-01 |
DE3320720C2 (en) | 1993-03-04 |
DE3320720A1 (en) | 1983-12-08 |
FR2528051B1 (en) | 1986-05-02 |
GB8315552D0 (en) | 1983-07-13 |
NL8302012A (en) | 1984-01-02 |
GB2121808B (en) | 1986-03-12 |
FR2528051A1 (en) | 1983-12-09 |
NL189818C (en) | 1993-08-02 |
IT1185501B (en) | 1987-11-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19990607 |