EP1252269A1 - Multifunctional additive compositions enabling middle distillates to be operable in cold conditions - Google Patents
Multifunctional additive compositions enabling middle distillates to be operable in cold conditionsInfo
- Publication number
- EP1252269A1 EP1252269A1 EP00993628A EP00993628A EP1252269A1 EP 1252269 A1 EP1252269 A1 EP 1252269A1 EP 00993628 A EP00993628 A EP 00993628A EP 00993628 A EP00993628 A EP 00993628A EP 1252269 A1 EP1252269 A1 EP 1252269A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- chosen
- additives
- carbon atoms
- additive
- 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
- 239000000654 additive Substances 0.000 title claims abstract description 104
- 230000000996 additive effect Effects 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims description 16
- 229920001577 copolymer Polymers 0.000 claims abstract description 27
- -1 amine salts Chemical class 0.000 claims abstract description 20
- 239000000446 fuel Substances 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims abstract description 9
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 238000004062 sedimentation Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 235000019198 oils Nutrition 0.000 claims description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 125000001204 arachidyl 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])[H] 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000913 palmityl 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])[H] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000007084 catalytic combustion reaction Methods 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 239000003879 lubricant additive Substances 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000010775 animal oil Substances 0.000 claims description 3
- 239000007866 anti-wear additive Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 239000004071 soot Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- PJNIZPXBKOEEGD-UHFFFAOYSA-N 2-(decylamino)ethanol Chemical compound CCCCCCCCCCNCCO PJNIZPXBKOEEGD-UHFFFAOYSA-N 0.000 claims description 2
- HCYSJBICYOIBLS-UHFFFAOYSA-N 2-(dodecylamino)ethanol Chemical compound CCCCCCCCCCCCNCCO HCYSJBICYOIBLS-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- NMJKZQOQEDDLSR-UHFFFAOYSA-N dodec-1-ene;furan-2,5-dione Chemical compound O=C1OC(=O)C=C1.CCCCCCCCCCC=C NMJKZQOQEDDLSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- COBLIZNSZVKDMR-UHFFFAOYSA-N furan-2,5-dione;octadec-1-ene Chemical compound O=C1OC(=O)C=C1.CCCCCCCCCCCCCCCCC=C COBLIZNSZVKDMR-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- JCDVRVQHKIBXTB-UHFFFAOYSA-N n'-[2-(docosylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNCCNCCN JCDVRVQHKIBXTB-UHFFFAOYSA-N 0.000 claims 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 claims 1
- 229940014569 pentam Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Chemical group CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004420 diamide group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- KXDZDQGNGXHCGI-UHFFFAOYSA-N octan-4-yl nitrate Chemical compound CCCCC(CCC)O[N+]([O-])=O KXDZDQGNGXHCGI-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 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
-
- 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
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
-
- 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
- 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
- C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
-
- 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
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
- C10L10/16—Pour-point depressants
Definitions
- Cold operability corresponds to a limit temperature at which middle distillates can be used without clogging problem. It is intermediate between the cloud point temperature (ASTM D 2500-98) characteristic of the start of crystallization of paraffins in the distillate and the pour point of the latter (ASTM D 97-96a).
- paraffins are crystallized at the bottom of the tank, they can be entrained at start-up in the fuel circuit and in particular clog the filters and prefilters placed upstream of the injection systems (pump and mjectors). Similarly for the storage of domestic fuel oils, paraffins precipitate in the bottom tank and can be driven and obstruct the lines upstream of the pump and the boiler supply system (nozzle and filter). It is obvious that the presence of solids, such as paraffin crystals, prevents the normal circulation of the middle distillate.
- TLF additives Filterability Limit Temperature
- the petroleum industry endeavored to develop anti-sedimentation additives, that is to say dispersants, which keep the paraffinic crystals in suspension in the middle distillate which prevents them from depositing and clump together.
- anti-sedimentation additives that is to say dispersants, which keep the paraffinic crystals in suspension in the middle distillate which prevents them from depositing and clump together.
- the Applicant has in particular developed such an additive described in patent EP 0 674 689.
- the combined action of the TLF and anti-sedimentation additives has not made it possible to improve the cold operability of all the middle distillates produced in refineries originating of all known crude oils.
- the present invention relates to a new multifunctional additive making it possible to lower and maintain the operating temperature when cold up to temperatures above -20 ° C., but also to increase the cetane content of these distillates, without any sedimentation. paraffins contained in middle distillates.
- a subject of the present invention is therefore a multifunctional additive for the cold operability of fuels consisting of copolymers having at least one dicarboxylic unit with at least one olefinic unit and on which are grafted nitrogen and / or ester functions of general formula (I) below:
- R x and R 2 are hydrogen or alkyl radicals comprising from 1 to 20 carbon atoms
- R 3 and R 6 are hydrogen or alkyl radicals comprising from 1 to 30 carbon atoms
- R3 chosen from alkyl groups comprising from 10 to 30 carbon atoms when R6 is hydrogen and vice versa
- R 4 and R 5 are hydrogen or an alkyl group comprising from 1 to 22 carbon atoms
- X is chosen from: ⁇ ) amme salts of type O NH + -R ' x
- R 'i and R' 2 are chosen from alkyl groups comprising from 1 to 18 carbon atoms, alkylamines comprising from 1 to 18 carbon atoms, N-alkylpolyalkylenepolyamines of formula
- R ' 3 and R' 4 identical or different, being hydrogen or a linear or branched alkyl group comprising from 1 to 22 carbon atoms, and x, y and z whole numbers, x varying from 1 to 6 and y and z varying from 0 to 6, and the mono and polyhydroxylated amines and polyamines,
- esters -OR ′ 5 , R ′ 5 being chosen from alkyl radicals comprising from 1 to 30 carbon atoms and the N-alkylpolyalkylenepolyamines of formula (II),
- alkylamines comprising from 1 to 44 carbon atoms and the N-alkylpolyalkylenepolyamines of formula
- the copolymer of formula (I) is preferably a copolymer containing from 45 to 65 mol% of at least one olefin unit and from 55 to 35 mol% of at least one dicarboxylic unit.
- the dicarboxylic units are preferably chosen from the group consisting of maleic anhydride, citraconic anhydride and fuma ⁇ que acid, and the olefin units chosen from linear or branched alkenyl units comprising from 1 to 30 carbon atoms.
- the copolymer is chosen from maleic anhydride-octadecene, maleic anhydride-dodecene and maleic anhydride-hexadecene copolymers.
- R 1 and R 2 are radicals preferably chosen from the group consisting of the dodecyl and octadecyl radicals and R 3 is chosen from alkyl groups comprising from 10 to 20 carbon atoms.
- R 'i and R' 2 are chosen from alkyl radicals with 12 to 18 carbon atoms, alkylamines comprising from _ to 22 carbon atoms and N-alkylpolyalkylenepolyamines of formula (II) and the hydroxylated amines of the group comprising diethanolamine, monoethanolamine, N-butylamine, N-decylethanolamine and N-dodecylethanolamine and their alkoxy derivatives, and R 3 chosen from the radicals decyl, tetradecyl, hexadecyl, octadecyl and eicosyl.
- a second additive according to the invention is the copolymer of formula (IV) below:
- R 'i and R' 2 are chosen from alkyl radicals containing from 1 22 carbon atoms and N-alkylpolyalkylenepolyamines from the group comprising N-alkyldiethylenetriammes, N-alkyldipropylenetriamines, N-alkylt ⁇ ethylenetetrammes, N-alkyltetraethy-lenepentammes and N-alkyltetra-propylenepentamines, and R 3 chosen from the radicals decyl, tetradecylhexadecyl, octadecyl and eicosyl.
- a third additive according to the invention is a copolymer of formula (V) below:
- the aikylamines and polyalkylene polyamines of formula (II) are preferably chosen from the group comprising dibutylamine, didodecylamine, dioctadecylamme, N-alkylethylenediammes, N-alkylpropylenediam es, N-alkylbutylenediammes, N- alkyldiethylenetriammes, N-alkyldipropylenetamines, N-alkyldibutylenets, N-alkyltriethylene tetrams, N-alkyltripropylenetetrams, N-alkyltributylenetetrams, N-alkyltetraethylene-tetramines, N-alkyltetra-ethylenetramines, from 12 to 22 carbon atoms, preferably N-dodecyldipropylenetriamme, N-octadecyldiprop
- a second subject of the invention is an additive composition
- an additive composition comprising an additive of formula (I) and at least one additive chosen from filtrablity and / or flow additives, procetane additives, catalytic combustion promoters and soot, detergents, lubricant additives, anti-wear and anti-foam additives, and other additives or additive compositions for improving the cloud point, dispersion and sedimentation of paraffins.
- procetane additive in particular (but not limited to) chosen from alkyl nitrates, preferably 2-ethylhexyl nitrate, aroyl peroxides, preferably benzyl peroxide, and alkyl peroxides, preferably ter-butyl peroxide.
- filterability additive in particular (but not limited to) chosen from ethylene / vinyl acetate (EVA), ethylene / vinyl propionate (EVP), ethylene / vinyl ethanoate (EVE), ethylene / methyl methacrylate copolymers ( EMMA), and ethylene / alkyl fumarate.
- additives examples include EP-A-0187488, FR-A- 2490669, EP-A-0722481, EP-A-0832172.
- anti-foam additive in particular (but not limited to) chosen from polysiloxanes, oxyalkyl polysiloxanes, and fatty acid amides derived from vegetable or animal oils. Examples of such additives are given in the following documents: EP-A-0861182, EP-A-0663000, EP-A-0736590.
- detergent and / or anti-corrosion additive in particular (but not limited to) selected from the group consisting of lashings, succmimides, alkenyl succimimides, polyalkylammes, polyalkyl polyammes and polyetherammes. Examples of such additives are given in the following documents: EP-A-0938535.
- lubricating or anti-wear additive in particular (but not limited to) chosen from the group consisting of fatty acids and their ester or amide derivatives, in particular glycerol monooleate, and derivatives of mono- and polycyclic carboxylic acids.
- cloud point additive in particular (but not limited to) chosen from the group consisting of long chain olefin / (meth) acrylic / maleimide terpolymers, and polymers of fumaric / maleic acid esters.
- anti-sedimentation additive in particular (but not li itatively) chosen from the group constituted by copolymers of (meth) acrylic acid / (meth) acrylate amidified by a polyamme, polyken alkenylsuccinimides, derivatives of phthalamic and fatty amino acid with double chain.
- EP-A-0261959 EP-A-00593331, EP-A-0674689, EP-A-0327423, EP-A-0512889, EP-A-0832172.
- polyfunctional additive for cold operability selected from the group consisting of polymers based on olefins and alkenyl nitrate as described in EP 0 573 490.
- a third object according to the invention is a fuel, fuel and / or fuel oil containing a major part of hydrocarbon base constituted by gasolines, middle distillates, synthetic fuels, animal or vegetable oils, whether or not esterified, and their mixtures. , and a minor part corresponding from 50 to 1000 ppm to at least one multifunctional additive of formula (I).
- This additive can be present in the fuel or fuel with at least one additive from the group consisting of procetane additives, catalytic combustion and soot promoters, detergents, lubricant additives, anti-wear additives, anti-additives. foam, anti-corrosion additives and other additives or additive compositions to improve the cloud point, dispersion and sedimentation of paraffins.
- the present example aims to show the filterability and flow efficiency of the additives according to the invention with a view to illustrating the intrinsic properties of the additives of formula (III), (IV) and (V) when they are used alone and when used in formulation with other additives.
- the additive (III) referenced below as additive 1 consists of a copolymer comprising maleic anhydride units and octadecene units in a molar ratio 1/1, Ri, R 2 , R ' x and R' 2 being identical and corresponding to radical dodecylamme.
- additive 2 consists of a copolymer comprising maleic anhydride units and octadecene units in a molar ratio 1/1, Ri and R ′ x being a hydrogen atom, R 2 a butyl radical and R ′ 2 being a dodecyl radical.
- additive 3 consists of a copolymer comprising maleic anhydride units and octadecene units in a molar ratio 1/1, Ri is a hydrogen atom, R 2 being a radical ethylamme and R ' 5 being a hexadecyl radical.
- the above copolymers are generally obtained by chemical modification of an alpha-olefin / maleic anhydride type copolymer, the alpha-olefin here being octadecene.
- the octadecene / maleic anhydride copolymer is synthesized in solution in a preferably aromatic solvent (for example toluene or xylene).
- the chain length of the olefin varies between 13 and 30 carbons, and this monomer is radically copolymerized (in a molar ratio varying from 0.4 to 0.6 with maleic anhydride, in mass or in solution.
- an initiator of the peroxide, hydroperoxide or azonitrile type in order to control the molecular mass of the polymer, and this, in weight concentrations varying from 0.5 to 5% of the sum of the monomers. preferably at temperatures between 60 and 140 ° C., and more precisely between 80 and 120 ° C.
- 2 molar equivalents of amine are reacted on a molar equivalent of anhydride, without bringing the temperature to a value too high not to obtain a diamide structure
- the reaction temperature can vary from 20 ° C. to 90 ° C., and preferably from 40 to 80 ° C. ester on subsequently reacts an alcohol in comparable proportions.
- the additives according to the invention provide a greater pour point gain than the known additives FI. This gain is further increased when the additives 1,2 and 3 are combined with one of the additives FI.
- the example presents the anti-sedimentation properties of the additives of formula (III), (IV) and (V) described in example 1 when they are introduced alone into the three gas oils 1, 2 and 3 at a content 0.025% by weight or in combination with two additives FI ⁇ and FI 2 at a concentration of 0.0125% by weight each.
- the effectiveness of these additives is determined in application of standard NF M07-085 (95), by a quotation of the TLF and of the starting crystallization temperature (TCC). The results are shown in Table IV below.
- the present example illustrates the capacity of additives 1,2 and 3 of the invention to lower the cloud point of gas oils, this cloud point corresponding to the starting crystallization temperature (TCC) determined according to standard IP 389/90.
- the present example illustrates the procetane effect brought about by the additive 3 of formula (III), used as such or in mixture with ethyl-2-hexyl nitrate, this effect being measured by applying standard ASTM-D613.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Detergent Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Beans For Foods Or Fodder (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK00993628T DK1252269T3 (en) | 1999-12-28 | 2000-12-27 | Composition of multifunctional additives for use in medium distillates in cold |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9916560A FR2802940B1 (en) | 1999-12-28 | 1999-12-28 | COMPOSITION OF MULTIFUNCTIONAL ADDITIVES FOR COLD OPERABILITY OF MEDIUM DISTILLATES |
FR9916560 | 1999-12-28 | ||
PCT/FR2000/003697 WO2001048122A1 (en) | 1999-12-28 | 2000-12-27 | Multifunctional additive compositions enabling middle distillates to be operable in cold conditions |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1252269A1 true EP1252269A1 (en) | 2002-10-30 |
EP1252269B1 EP1252269B1 (en) | 2004-12-15 |
Family
ID=9553895
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00993628A Expired - Lifetime EP1252269B1 (en) | 1999-12-28 | 2000-12-27 | Multifunctional additive compositions enabling middle distillates to be operable in cold conditions |
Country Status (15)
Country | Link |
---|---|
US (2) | US7326262B2 (en) |
EP (1) | EP1252269B1 (en) |
JP (1) | JP2003518549A (en) |
KR (1) | KR100700416B1 (en) |
AT (1) | ATE284938T1 (en) |
AU (1) | AU5787801A (en) |
CZ (1) | CZ299447B6 (en) |
DE (1) | DE60016804T2 (en) |
ES (1) | ES2234710T3 (en) |
FR (1) | FR2802940B1 (en) |
HU (1) | HU225070B1 (en) |
PL (1) | PL191951B1 (en) |
PT (1) | PT1252269E (en) |
RU (1) | RU2257400C2 (en) |
WO (1) | WO2001048122A1 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2802940B1 (en) | 1999-12-28 | 2003-11-07 | Elf Antar France | COMPOSITION OF MULTIFUNCTIONAL ADDITIVES FOR COLD OPERABILITY OF MEDIUM DISTILLATES |
DE10349851B4 (en) * | 2003-10-25 | 2008-06-19 | Clariant Produkte (Deutschland) Gmbh | Cold flow improver for fuel oils of vegetable or animal origin |
KR101143114B1 (en) * | 2003-11-13 | 2012-05-08 | 인피늄 인터내셔날 리미티드 | A method of inhibiting deposit formation in a jet fuel at high temperatures |
DE10357877B4 (en) * | 2003-12-11 | 2008-05-29 | Clariant Produkte (Deutschland) Gmbh | Fuel oils from middle distillates and oils of vegetable or animal origin with improved cold properties |
DE10357880B4 (en) * | 2003-12-11 | 2008-05-29 | Clariant Produkte (Deutschland) Gmbh | Fuel oils from middle distillates and oils of vegetable or animal origin with improved cold properties |
US20050138859A1 (en) * | 2003-12-16 | 2005-06-30 | Graham Jackson | Cold flow improver compositions for fuels |
CA2562255C (en) * | 2004-04-06 | 2013-01-29 | Rodney Lee Cravey | Pour point depressant additives for oil compositions |
CN1786046A (en) * | 2005-11-21 | 2006-06-14 | 中国科学院长春应用化学研究所 | Polymer end closing agent of carbon diovide-epoxide copolymer and its preparation method |
DE102006022719B4 (en) | 2006-05-16 | 2008-10-02 | Clariant International Limited | Cold flow improver for vegetable or animal fuel oils |
FR2925916B1 (en) * | 2007-12-28 | 2010-11-12 | Total France | VINYL ETHYLENE / UNSATURATED TERPOLYMER / UNSATURATED ESTERS AS AN ADDITIVE TO ENHANCE COLD LIQUID HYDROCARBONS LIKE MEDIUM DISTILLATES AND FUELS OR COMBUSTIBLES |
JP4131748B1 (en) * | 2008-01-16 | 2008-08-13 | 株式会社タイホーコーザイ | Fuel additive |
RU2471858C2 (en) * | 2010-12-27 | 2013-01-10 | Игорь Анатольевич Ревенко | Method of increasing rate and completeness of fuel oxidation in combustion systems |
US10557096B2 (en) | 2014-11-27 | 2020-02-11 | Basf Se | Copolymer and use thereof for reducing crystallization of paraffin crystals in fuels |
WO2018064270A1 (en) * | 2016-09-29 | 2018-04-05 | Ecolab USA, Inc. | Paraffin inhibitors, and paraffin suppressant compositions and methods |
AU2017335819B2 (en) * | 2016-09-29 | 2021-10-21 | Ecolab Usa Inc. | Paraffin suppressant compositions and methods |
US20180155645A1 (en) * | 2016-12-07 | 2018-06-07 | Ecolab Usa Inc. | Antifouling compositions for petroleum process streams |
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JPS5486505A (en) | 1977-12-22 | 1979-07-10 | Toho Kagaku Kougiyou Kk | Fuel oil composition |
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DE3405843A1 (en) * | 1984-02-17 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | COPOLYMERS BASED ON MALEINIC ACID ANHYDRIDE AND (ALPHA), (BETA) -UNAUSAUTED COMPOUNDS, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS PARAFFIN INHIBITORS |
JPS61211397A (en) | 1985-03-18 | 1986-09-19 | Kao Corp | Flowability improver for fuel oil |
JPS61296090A (en) | 1985-06-25 | 1986-12-26 | Kao Corp | Fuel oil additive |
GB8706369D0 (en) * | 1987-03-18 | 1987-04-23 | Exxon Chemical Patents Inc | Crude oil |
GB8812380D0 (en) * | 1988-05-25 | 1988-06-29 | Exxon Chemical Patents Inc | Fuel oil compositions |
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US5857287A (en) * | 1997-09-12 | 1999-01-12 | Baker Hughes Incorporated | Methods and compositions for improvement of low temperature fluidity of fuel oils |
FR2792646B1 (en) * | 1999-04-26 | 2001-07-27 | Elf Antar France | COMPOSITION OF MULTI-FUNCTIONAL COLD OPERABILITY ADDITIVES FOR MEDIUM DISTILLATES |
FR2802940B1 (en) | 1999-12-28 | 2003-11-07 | Elf Antar France | COMPOSITION OF MULTIFUNCTIONAL ADDITIVES FOR COLD OPERABILITY OF MEDIUM DISTILLATES |
-
1999
- 1999-12-28 FR FR9916560A patent/FR2802940B1/en not_active Expired - Fee Related
-
2000
- 2000-12-27 WO PCT/FR2000/003697 patent/WO2001048122A1/en active IP Right Grant
- 2000-12-27 HU HU0204536A patent/HU225070B1/en not_active IP Right Cessation
- 2000-12-27 JP JP2001548641A patent/JP2003518549A/en active Pending
- 2000-12-27 ES ES00993628T patent/ES2234710T3/en not_active Expired - Lifetime
- 2000-12-27 DE DE60016804T patent/DE60016804T2/en not_active Expired - Lifetime
- 2000-12-27 CZ CZ20022295A patent/CZ299447B6/en not_active IP Right Cessation
- 2000-12-27 PL PL356098A patent/PL191951B1/en unknown
- 2000-12-27 PT PT00993628T patent/PT1252269E/en unknown
- 2000-12-27 RU RU2002120507/04A patent/RU2257400C2/en not_active IP Right Cessation
- 2000-12-27 US US10/149,844 patent/US7326262B2/en not_active Expired - Fee Related
- 2000-12-27 EP EP00993628A patent/EP1252269B1/en not_active Expired - Lifetime
- 2000-12-27 KR KR1020027008391A patent/KR100700416B1/en not_active IP Right Cessation
- 2000-12-27 AT AT00993628T patent/ATE284938T1/en active
- 2000-12-27 AU AU57878/01A patent/AU5787801A/en not_active Abandoned
-
2008
- 2008-02-04 US US12/025,558 patent/US8100988B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO0148122A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU5787801A (en) | 2001-07-09 |
ATE284938T1 (en) | 2005-01-15 |
EP1252269B1 (en) | 2004-12-15 |
JP2003518549A (en) | 2003-06-10 |
US20080244964A1 (en) | 2008-10-09 |
HU225070B1 (en) | 2006-06-28 |
US8100988B2 (en) | 2012-01-24 |
US20030163951A1 (en) | 2003-09-04 |
RU2002120507A (en) | 2004-01-10 |
FR2802940B1 (en) | 2003-11-07 |
FR2802940A1 (en) | 2001-06-29 |
KR100700416B1 (en) | 2007-03-27 |
DE60016804T2 (en) | 2005-12-15 |
RU2257400C2 (en) | 2005-07-27 |
PT1252269E (en) | 2005-04-29 |
PL356098A1 (en) | 2004-06-14 |
CZ299447B6 (en) | 2008-07-30 |
US7326262B2 (en) | 2008-02-05 |
KR20020074181A (en) | 2002-09-28 |
ES2234710T3 (en) | 2005-07-01 |
WO2001048122A1 (en) | 2001-07-05 |
DE60016804D1 (en) | 2005-01-20 |
PL191951B1 (en) | 2006-07-31 |
HUP0204536A2 (en) | 2003-05-28 |
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