EP1192239B1 - Zusammensetzung von merhzweckzusätzen zur kälteverwendbarkeit der mitteldestillate - Google Patents

Zusammensetzung von merhzweckzusätzen zur kälteverwendbarkeit der mitteldestillate Download PDF

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Publication number
EP1192239B1
EP1192239B1 EP00922705A EP00922705A EP1192239B1 EP 1192239 B1 EP1192239 B1 EP 1192239B1 EP 00922705 A EP00922705 A EP 00922705A EP 00922705 A EP00922705 A EP 00922705A EP 1192239 B1 EP1192239 B1 EP 1192239B1
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Prior art keywords
composition
additive
chosen
weight
anhydride
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EP00922705A
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English (en)
French (fr)
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EP1192239A1 (de
Inventor
Franck Eydoux
Robert Leger
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Total Marketing Services SA
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TotalFinaElf France SA
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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
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained

Definitions

  • the present invention relates to a new composition of multifunctional additives improving the cold operability of middle distillates, especially in during slow cooling processes during storage fuels and fuels at low temperatures. It aims in particular to improve the anti-sedimentation properties for application in fuels for Diesel engines and in fuels such as fuel oils domestic for boilers.
  • Cold operability corresponds to a temperature limit at which middle distillates can be used without clogging problem. She is intermediate between cloud point temperature (ASTM D 2500-66) characteristic of the onset of crystallization of paraffins in the distillate and the pour point of the latter (ASTM D 97-66).
  • paraffins are crystallized at bottom of the tank, they can be dragged starting in the engine and clogging in particular the filters and prefilters arranged upstream of the injection systems (pump and injectors).
  • paraffins precipitate at the bottom of the tank and may be entrained and obstruct upstream pipes pump and 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 Temporal Limit of Filterability
  • the present invention relates to a composition multifunctional additives for lowering and maintain the cold operability temperature of middle distillates, so that during a stage of slow cooling during storage in a closed enclosure, up to temperatures above -20 ° C, we do not observe no sedimentation of the paraffins contained in the middle distillates.
  • the composition of additives is obtained by combining 50 to 80% AB and 20 to 50% by weight of the CD reaction product.
  • the composition of additives comprises from 50 to 80% by weight of a combination AB, CD in an AB / CD molar ratio varying from 0.2 to 4, and from 20 to 50% by weight of a mixture of AD, CB in a ratio AD / CB molar varying from 0.2 to 4.
  • the carboxylic compound (A) is preferably chosen in the group comprising dodecylmaleic anhydrides, dodecenylmaleic, hexadecylmaleic, hexadecenylmaleic octadecylmaleic, octadecenylmaleic, eicosylmaleic and éicosénylmaléique.
  • the polyalkyleneamine (B) is preferably chosen in the group comprising diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine and tetrapropylene.
  • the copolymer (C) is preferably a copolymer containing 45 to 65 mol% of at least one acid unit carboxylic and from 55 to 35 mol% of at least one ester unit alkylated.
  • the carboxylic acid units are chosen preferably among the units resulting from acids acrylic and methacrylic, and alkyl ester patterns among the patterns resulting from acrylic esters and methacrylics, and their derivatives.
  • the copolymer (C) is chosen from acrylic acid / methacrylic ester copolymers and methacrylic acid / acrylic ester copolymers containing 45 to 65 mole% of acid units and 55 to 35 mole% of ester patterns.
  • the N-alkylpolyalkylenepolyamine (D) is preference chosen from the group comprising N-alkylethylenediamines, N-alkylpropylenediamines, N-alkylbutylenediamines, N-alkyldiethylenetriamines, N-alkyldipropylenetriamines, N-alkyldibutylenetriamines, N-alkyltriethylenetetramines, N-alkyltripropylenetetramines and N-alkyltributylenetetramines having a alkyl radical comprising from 12 to 22 carbon atoms.
  • D is chosen from N-dodecyldipropylenetriamine, N-octadecyldipropylene triamine, N-octadecyldiethylenetriamine and N-docosyldiethylenetriamine.
  • a second object of the invention is a fuel containing a major part of middle distillate containing usually a filterability additive, and some minor, for example 50 to 1000 ppm of a composition Multifunctional cold operability additives for slow cooling.
  • This example presents the two methods of cooling implemented as well as the composition of diesel and additives tested.
  • the quench cooling method described in standard NFT M07-085, consists in pouring a sample of distillate in a graduated cylinder in volume and place for 24 hours in a refrigerated cabinet at one temperature generally set between -13 and -20 ° C, i.e. a temperature at least 1 ° C lower than its temperature cloud point, and at least 6 ° C higher than its pour point temperature.
  • the anti-sedimentation function of the additive compositions is therefore effective. If the upper phase is clear and a cloudy compaction appears at the bottom of the test tube, the sedimentation is important and the composition of additives ineffective in anti-sedimentation.
  • the slow cooling method is to introduce the sample of diesel fuel with or without additives into a cylinder graduated in volume, to place in a cabinet refrigerated at a temperature 10 ° C higher than the cloud point temperature of said diesel.
  • the sample is gradually cooled from this temperature from 1 to 3 ° C / hour, up to a final test temperature that can reach -15 to -20 ° C. Once the final temperature reached, the sample is kept for 24 hours at this temperature, then we do the visual rating already mentioned for the rapid quenching method, as well as the samples from the top and bottom of the test piece to determine the temperatures Tcc and TLF of these different phases. Interpretation of the results is identical to the rapid quenching method.
  • This example aims to show the difference between the quench cooling method and the method by slow cooling to 1 ° C per hour and therefore the interest to select additives reproducing the phenomenon of actual cooling of a stopped car tank and therefore the diesel cooling process.
  • composition of multifunctional additives is all the more effective the smaller the sum of the six differences on the three diesel fuels.
  • Ranking difference Tcc TLF gap difference Tcc TLF gap difference Tcc TLF gap Gi + TLF 21.2 11 17.8 10 19.7 10 89.7 11 AD 2.1 0 3.9 3 9.4 1 19.4 1 st AB 6.2 4 15.8 11 12.0 2 51 4 CD 2.2 6 7.2 3 12.7 4 35.1 2 CB 16.1 6 17.0 9 19.2 11 78.3 10 X 1 5.0 0 15.5 6 17.3 9 52.8 5 X 2 4.6 0 14.3 7 17.1 10 53 6 X 3 8.2 2 16.3 9 16.2 8 59.7 8 X 4 9.6 3 17.0 11 13.7 4 58.3 7 X 5 10.5 3 12.3 5 12.0 5 47.8 3 X 6 11.4 3 16.0 9 18.5 9 66.9 9 Slow method 1

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Beans For Foods Or Fodder (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Confectionery (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (11)

  1. Zusammensetzung von Mehrzweckzusätzen zur Kälteverwendbarkeit der Mitteldestillate resultierend aus einer Reaktion von Carboxylverbindungen mit Aminverbindungen dadurch gekennzeichnet, dass sie wenigstens 50 Gew.% einer Mischung enthält, die gebildet ist aus:
    a) 10 bis 90 Gew.% eines Additivs (AB) wenigstens einer Carboxylverbindung (A) ausgewählt unter den Anhydriden der Alkylmaleinsäuren und Alkenylmaleinsäuren und den Anhydriden der Alkylsuccinate und Alkenylsuccinate mit 4 bis 32 Kohlenstoffatomen in den Radikalen der Alkyle und Alkenyle, den Säuren und den korrespondierenden Estern mit wenigstens einer Aminverbindung (B) ausgewählt unter den Polyakylaminen mit folgender allgemeiner Formel (I): NH2-[(CH2)n-NH-]m-H worin n eine ganze Zahl ist variierend zwischen 2 und 4 und m eine ganze Zahl ist variierend zwischen 1 und 4, dass Molverhältnis A/B variierend zwischen 1 / m+1 und m+1, insbesondere zwischen 1 und 2,
    b) und 90 bis10 Gew.% eines Additivs (CD)
    i) wenigstens eines Copolymers (C) resultierend aus einer Reaktion von wenigstens einer ersten ungesättigten substituierten oder unsubstituierten Carbonsäure mit wenigstens einem Akylester wenigstens einer zweiten ungesättigten substituierten oder unsubstituierten Carbonsäure, identisch oder verschieden zur ersten Carbonsäure, mit folgender allgemeiner Formel (II):
    Figure 00220001
    in der R1 und R2, identisch oder verschieden, ausgewählt sind aus der Gruppe bestehend aus Wasserstoff, und linearen oder verzweigten Alkylgruppen mit 1 bis 20 Kohlenstoffatomen, R3 Wasserstoff ist oder eine lineare Alkylgruppe von höchstens 3 Kohlenstoffatomen und R4 Wasserstoff ist oder eine Alkylgruppe von 1 bis 25 Kohlenstoffatomen,
    ii) mit einem N-alkylpolyalkylenpolyamin (D) mit folgender allgemeiner Formel (III): R5-NH-[-(CH2)p- NH-]q-H worin R5 ein gesättigtes aliphatisches Radikal mit 12 bis 22 Kohlenstoffatomen ist, p eine ganze Zahl ist variierend zwischen 2 und 4, q eine ganze Zahl ist variierend zwischen 1 und 4, das Molverhältnis C/D variierend zwischen 1 / q+1 und q+1, insbesondere variierend zwischen 1 und 2 .
  2. Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass sie gebildet ist aus:
    50 bis 100 Gew.% einer Kombination enthaltend 20 bis 80 Gew.% eines Additivs AB und 80 bis 20 Gew.% eines Additivs CD,
    und 0 bis 50 Gew.% einer Kombination der Additive AD und CB erhältlich durch Reaktion von A und von D mit einem Molverhältnis variierend zwischen 0,2 und 4, und von B mit C mit einem Molverhältnis variierend zwischen 0,2 und 4.
  3. Zusammensetzung nach Anspruch 1 oder 2 dadurch gekennzeichnet, dass sie erhältlich ist durch Kombination von 50 bis 80% eines Additivs AB und 20 bis 50 Gew.% eines Additivs CD.
  4. Zusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass sie 50 bis 80 Gew.% einer Kombination AB,CD mit einem Molverhältnis AB/CD variierend zwischen 0,2 und 4, und 20 bis 50 Gew.% einer Kombination AD,CB mit einem Molverhältnis AD/CB variierend zwischen 0,2 und 4 aufweist.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass die Carboxylverbindung (A) ausgewählt ist aus der Gruppe, bestehend aus einem Anhydrid der Dodecylmaleinsäure, Dodecenylmaleinsäure, Hexadecylmaleinsäure, Hexadecenylmaleinsäure, Oktadecylmaleinsäure, Oktadecenylmaleinsäure, Eicosylmaleinsäure und Eicosenylmaleinsäure.
  6. Zusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das Polyalkylamin (B) ausgewählt ist in der Gruppe aufweisend das Diethylentriamin, das Dipropylentriamin, das Triethylentetramin, das Tetraethylenpentamin und das Tetrapropytenpentamin.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass das Copolymer (C) ausgewählt ist unter den Copolymeren enthaltend 45 bis 65 Mol% wenigstens einer Carbonsäure-Einheit und 55 bis 35 Mol% wenigstens einer Alkylester-Einheit, die Carbonsäure-Einheiten ausgewählt sind unter Acrylsäure-Einheiten und Methacrylsäure-Einheiten und die Alkylester-Einheiten unter Acrylester-Einheiten und Methacrylester-Einheiten, und ihren Derivaten.
  8. Zusammensetzung nach Anspruch 7, dadurch gekennzeichnet, dass das Copolymer (C) ausgewählt ist unter den Copolymeren von Acrylsäure/Methacrylester und Copolymeren von Methacrylsäure/Acrylester enthaltend 45 bis 65 Mol% Carbonsäure-Einheiten und 55 bis 35 Mol% Ester-Einheiten.
  9. Zusammensetzung nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass das N-alkylpolyalkylenpolyamin (D) eine Verbindung ist aus der Gruppe bestehend aus N-alkylethylendiaminen, N-alkylpropylendiaminen, N-alkylbutylendiaminen, den N-alkyldiethylentriaminen, den N-alkyldipropylentriaminen, den N-alkyldibutylentriaminen, den N-alkyltriethylentetraminen, den N-alkyltripropylentetraminen und den N-alkyltributylentetraminen präsentierend ein Alkylradikal, das 12 bis 22 Kohlenstoffatome aufweist.
  10. Zusammensetzung nach Anspruch 9, dadurch gekennzeichnet, dass N-alkylpolyalkylenpolyamin D ausgewählt ist in der Gruppe aufweisend das N-dodecyldipropylentriamin, das N-oktadecyldipropylentriamin, das N-oktadecyldiethylentriamin und das N-docosyldiethylentriamin.
  11. Treibstoff enthaltend einen größeren Teil eines Mitteldestillats, enthaltend gegebenenfalls ein Filtrierbarkeitsadditiv und einen kleineren Teil, beispielsweise 50 bis 1000 ppm einer Zusammensetzung von Mehrzweckzusätzen nach einem der Ansprüche 1 bis 10.
EP00922705A 1999-04-26 2000-04-21 Zusammensetzung von merhzweckzusätzen zur kälteverwendbarkeit der mitteldestillate Expired - Lifetime EP1192239B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SI200030075T SI1192239T1 (en) 1999-04-26 2000-04-21 Multifunctional additive composition for cold process treatment of middle distillates

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9905235A FR2792646B1 (fr) 1999-04-26 1999-04-26 Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens
FR9905235 1999-04-26
PCT/FR2000/001052 WO2000065000A1 (fr) 1999-04-26 2000-04-21 Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens

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EP1192239B1 true EP1192239B1 (de) 2003-02-05

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US (1) US6623536B1 (de)
EP (1) EP1192239B1 (de)
JP (1) JP2002543237A (de)
KR (1) KR100657047B1 (de)
AT (1) ATE232233T1 (de)
CA (1) CA2367927C (de)
CZ (1) CZ296126B6 (de)
DE (1) DE60001368T2 (de)
DK (1) DK1192239T3 (de)
ES (1) ES2192175T3 (de)
FR (1) FR2792646B1 (de)
PL (1) PL192234B1 (de)
PT (1) PT1192239E (de)
SI (1) SI1192239T1 (de)
SK (1) SK285752B6 (de)
WO (1) WO2000065000A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2802940B1 (fr) * 1999-12-28 2003-11-07 Elf Antar France Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens
FR2839315B1 (fr) * 2002-05-03 2006-04-28 Totalfinaelf France Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures
US20050138859A1 (en) * 2003-12-16 2005-06-30 Graham Jackson Cold flow improver compositions for fuels

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2490669A1 (fr) * 1980-09-19 1982-03-26 Elf France Nouvelles compositions d'additifs permettant l'amelioration de la temperature limite de filtrabilite et l'inhibition simultanee des cristaux de n-paraffines formes lors du stockage a basse temperature des distillats moyens
FR2510598A1 (fr) * 1981-07-30 1983-02-04 Inst Francais Du Petrole Utilisation d'additifs azotes comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2633638B1 (fr) * 1988-06-29 1991-04-19 Inst Francais Du Petrole Formulations d'additifs azotes pour carburants moteurs et les carburants moteurs les contenant
IT1229659B (it) * 1989-04-21 1991-09-06 Euron Spa Additivo detergente, disperdente ed anti ruggine per combustibili ed oli lubrificanti.
JPH0751711B2 (ja) * 1991-11-26 1995-06-05 三洋化成工業株式会社 燃料油用流動性向上剤および燃料油組成物
FR2699550B1 (fr) * 1992-12-17 1995-01-27 Inst Francais Du Petrole Composition de distillat moyen de pétrole contenant des additifs azotés utilisables comme agents limitant la vitesse de sédimentation des paraffines.
FR2710652B1 (fr) * 1993-09-30 1995-12-01 Elf Antar France Composition d'additifs d'opérabilité à froid des distillats moyens.
DE4430294A1 (de) * 1994-08-26 1996-02-29 Basf Ag Polymermischungen und ihre Verwendung als Zusatz für Erdölmitteldestillate
FR2735494B1 (fr) * 1995-06-13 1997-10-10 Elf Antar France Additif bifonctionnel de tenue a froid et composition de carburant
CA2189918C (en) * 1995-11-13 2005-01-25 Richard Mark Scott Dispersant additives
US5755834A (en) * 1996-03-06 1998-05-26 Exxon Chemical Patents Inc. Low temperature enhanced distillate fuels
GB9610363D0 (en) * 1996-05-17 1996-07-24 Ethyl Petroleum Additives Ltd Fuel additives and compositions
DE19622052A1 (de) * 1996-05-31 1997-12-04 Basf Ag Paraffindispergatoren für Erdölmitteldestillate

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Publication number Publication date
SK285752B6 (sk) 2007-07-06
CA2367927A1 (en) 2000-11-02
PL192234B1 (pl) 2006-09-29
JP2002543237A (ja) 2002-12-17
ATE232233T1 (de) 2003-02-15
KR100657047B1 (ko) 2006-12-12
FR2792646B1 (fr) 2001-07-27
PL352553A1 (en) 2003-08-25
PT1192239E (pt) 2003-06-30
ES2192175T3 (es) 2003-10-01
DE60001368T2 (de) 2003-11-27
EP1192239A1 (de) 2002-04-03
WO2000065000A1 (fr) 2000-11-02
CA2367927C (en) 2008-06-17
DK1192239T3 (da) 2003-05-26
DE60001368D1 (de) 2003-03-13
US6623536B1 (en) 2003-09-23
CZ296126B6 (cs) 2006-01-11
SI1192239T1 (en) 2003-06-30
CZ20013842A3 (cs) 2002-05-15
KR20020050755A (ko) 2002-06-27
SK15132001A3 (sk) 2002-05-09
FR2792646A1 (fr) 2000-10-27

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