WO1997044414A1 - Procede pour moteur diesel marin et carburant correspondant - Google Patents

Procede pour moteur diesel marin et carburant correspondant Download PDF

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Publication number
WO1997044414A1
WO1997044414A1 PCT/GB1997/001380 GB9701380W WO9744414A1 WO 1997044414 A1 WO1997044414 A1 WO 1997044414A1 GB 9701380 W GB9701380 W GB 9701380W WO 9744414 A1 WO9744414 A1 WO 9744414A1
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WIPO (PCT)
Prior art keywords
fuel
process according
detergent
marine diesel
amine
Prior art date
Application number
PCT/GB1997/001380
Other languages
English (en)
Inventor
Robert William Allen
Michael James Attfield
Original Assignee
Bp Chemicals (Additives) Limited
Castrol Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bp Chemicals (Additives) Limited, Castrol Limited filed Critical Bp Chemicals (Additives) Limited
Priority to AU29077/97A priority Critical patent/AU2907797A/en
Publication of WO1997044414A1 publication Critical patent/WO1997044414A1/fr

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    • C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)

Definitions

  • the present invention relates in general to marine diesel engines, typically four-stroke medium speed diesel engines, and to fuels therefor
  • the present invention relates to a process for reducing liner lacquering in a marine diesel engine operating on a fuel capable of giving rise thereto
  • a problem recently observed in connection with marine diesel engines, such as those powering Dutch fishing vessels, is that of liner lacquering whereby a hard resin-like material forms on cylinder liners and fills the honing grooves. This problem manifests itself in increased lubricating oil consumption which incurs a financial penalty
  • a solution to the problem, namely replacing the cylinder liners at regular intervals also carries a financial penalty in that the vessel is temporarily out of commission during replacement of the liners in addition to the cost of replacement itself
  • the present invention provides a process for reducing liner lacquering in a marine diesel engine operating on a marine diesel fuel of a quality capable of giving rise to liner lacquering which process comprises adding to the fuel a liner lacquering reducing amount of a fuel-soluble composition comprising - (A) at least one diesel detergent, and (B) at least one combustion improver
  • Marine diesel engines which are prone to liner lacquering problems are generally four stroke engines running on gas oils and to a lesser extent two stroke crosshead engines
  • Marine diesel fuels of a quality capable of giving rise to liner lacquering are generally those having a high, typically greater than 340°C, for example greater than 360°C, preferably greater than 420°C, temperature for a 90% volume recovery during distillation and a high, ie greater than 25%, particularly greater than 35%, aromatics content Generally this is accompanied by a low saturates content (less than 60%) and a low olefins content (less than 3%).
  • the cetane number of such fuels is also generally about 40, or less
  • marine diesel fuels of a quality capable of giving rise to liner lacquering are generally those of a low sulphur content for example less than 2%, preferably less than 0.5%, more preferably less than 0.2% w/w
  • the fuel-soluble composition added to the fuel comprises (A) at least one diesel detergent, and (B) at least one combustion improver.
  • the diesel detergent (A) are materials which function to prevent the build-up of deposits in inter alia the injection system, particularly the injector nozzle, of a diesel engine which can adversely affect both the fuel flow and fuel atomisation characteristics of the injector.
  • diesel detergent includes all those materials which would be suitable for use in diesel engines and which have detergent action, generally classified as dispersants which have detergency action. Detergency in diesel engines is generally associated with a range of amine type detergents and polymeric dispersants typified by the following compounds:- amines, imidazolines, amides, fatty acid succinimides, polyalkylene succinimides. polyalkylene amines and polyether amines.
  • Preferred detergents are (i) oil-soluble amides or imides of long-chain hydrocarbyl-substituted mono- or dicarboxylic acids or their anhydrides and (ii) long-chain hydrocarbons having a polyamine attached directly thereto.
  • a preferred detergent is an imide or amide formed by the reaction of a polyalkene substituted succinic acylating agent and an amine.
  • Succinimides are a well-known class of detergent. Typical of the art relating to such materials is GB-A- 1565627 and the prior art acknowledged therein Typically, they are prepared by reacting a polyalkene, in the presence or absence of chlorine, with either maleic acid, or preferably maleic anhydride, to produce a polyalkene-substituted succinic acid or anhydride and thereafter reacting the polyalkene-substituted succinic acid or anhydride with a nitrogenous material, suitably an amine, which may be a mono-, di- or polyamine
  • a suitable succinimide has the formula -
  • R ⁇ IS a hydrocarbyl group, typically a polyolefin group, preferably containing between 30 and 300 carbon atoms, more preferably between 50 and 150 carbon atoms
  • R J is a divalent group such that HbNR-'NXY is an alkylene amine, such as an ethylene or propylene amine, for example
  • R-* is - (CH ⁇ CI-bNH ⁇ CI- ⁇ CP ⁇ wherein k is zero or an integer from 1 to 7, preferably 2 to 6, or a mixed ethylene/propylene amine, for example H 2 N(CH2)3NH(CH2)2NH(CH 2 )3 NH 2 - and
  • X and Y are independently either hydrogen, alkyl, or hydroxy alkyl, each of 1 -6 carbon atoms, eg methyl, ethyl or hydroxyethyl, or together form the group -
  • R 3 in the formula (I) may be a divalent group such that ⁇ NR ⁇ NXY is an alkanolamine or a polyether amine.
  • R3 may also be a divalent group such that ⁇ NR ⁇ NXY is an aromatic or araliphatic amine, eg of 6-20 carbon atoms, such as phenylene or biphenylene diamine or bis( amino benzyl)
  • R is derived from either ethylene, propylene, 1- butene, isobutene, l-hexene, l-octene, and the like.
  • the polyalkene may be derived from an internal olefin, eg 2-butene, or an interpoiymer, eg an ethylene/propylene copolymer
  • the polyalkene is a polyisobutene.
  • the succinimide may be either a mono- or a bis-succinimide.
  • Diesel detergents are marketed in various additive packages marketed by several additive manufacturers In general the additive packages available appear to be based on compounds which can be classified as polymeric dispersants.
  • the high viscosity of these compounds generally dictates that they are distributed in diluted form, typically 50% or more of an aromatic kerosene diluent being used. Any of the commercially available detergents may be employed. The amount of detergent employed may be sufficient to provide up to 1000 ppm, for example up to 500 ppm, typically up to 250 ppm in the fuel, for example 100 to 200 ppm.
  • combustion improver (B) these are compounds which are useful in promoting the combustion of hydrocarbon fuels, in particular diesel fuels. They are believed to act as catalysts for the oxidation of combustion residues and exhaust gases of hydrocarbon fuels Any of the additives which have been suggested for use in diesel fuels to reduce particulate emissions may be employed as the component (B), for example those described in US Patent Nos. 2,926,454; 3,410,670, 3,413, 102, 3,539,3 12 and 3,499,742.
  • organometallic compounds either alone or in combination with oxygenated compounds, have been described as useful for reducing soot and visible paniculate matters from the exhausts of diesel fuelled engines
  • Typical of such combinations are a mixture of an oxygenated compound and an alkyl cyclopentadienyl manganese tricarbonyl as described in US Patent No. 4,207,078; a mixture of a wax oxidate and an alkylcyclopentadienyl manganese tricarbonyl complex salt as described in US Patent No. 4,222,746, and a mixture of a diesel fuel soluble compound of a rare earth metal, preferably cerium, and an oxygenated compound as described in US Patent No.
  • the diesel fuel soluble compounds of a rare earth metal are suitably organometallic compounds containing oxygen, preferably the carbonyls, typically rare earth metal salts of alkyl carboxylic acids, and of cycloalkyl carboxylic acids, preferably a rare earth octoate of the formula
  • Suitable oxygenated compounds include alkylcarbitols having from about 5 to about 16 carbon atoms, preferably a monoalkyl ether of diethylene glycol The most preferred carbitol is n- hexylcarbitol
  • a preferred class of combustion improvers useful in the performance of the present invention are rare earth metal oxidic compounds, preferably cerium oxidic compounds, for example cerium carboxylates, sulphonates, salicylates, and the like
  • preferred compounds include those of Ce(IV), especially those containing for each Ce(IV) atom two residues of an organic oxyacid, advantageously at least one of which has a pKa greater than 1 , or a mixture of such acids, and one other oxygen atom bonded to the Ce(IV) atom in addition to the oxygen atoms constituting the organic oxyacid residues (this oxygen
  • Preferred compounds for use in the process of the invention include those derived from cerium and a sulphonic acid
  • the amount of combustion improver employed may suitably be sufficient to provide up to 500 ppm, for example up to 200 ppm, typically up to 50 ppm in the fuel, for example from 10 - 50 ppm
  • the fuel soluble composition may include as an optional component (C) a cetane improver
  • a cetane improver These are materials which promote fast oxidation of fuels and thus improve their ignition characteristics
  • Typical cetane improvers include the alkyl nitrates, ether nitrates, dinitrates of polyethylene glycols and certain peroxides In general, however, in view of their low cost and ease of handling primary alkyl nitrates are preferred
  • suitable cetane improvers useful in the performance of the invention include iso-propyl nitrate, iso-amy!
  • cetane improver is iso-octyl nitrate
  • cetane improver should increase the cetane number of the fuel to about 45, or greater
  • the cetane number of the fuel may be increased by the addition of a hydrocarbon fraction known to be beneficial to ignition quality, for example a paraffinic hydrocarbon fraction
  • the fuel- soluble composition preferably incorporates as component (D) a demulsifier for fuel-water emulsions
  • a demulsifier for fuel-water emulsions Any of the commercially available demulsifiers may be employed, suitably in an amount sufficient to provide a treat level of from 5 to 50 ppm in the fuel
  • suitable demulsifiers are the quaternary amine salts
  • suitable demulsifiers include alkoxylated polyglycols and arylsulphonates
  • the fuel-soluble composition preferably further incorporates as component (E) an antioxidant Antioxidants are useful for inhibiting gum formation during fuel storage Diesel antioxidants m current use are mainly based on hindered phenol or amine. foi example phenylenediamines, structures Any of the commercially available diesel antioxidants may be employed, suitably in an amount sufficient to provide a dose tate of from 2 to 200 ppm in the fuel
  • the fuel-soluble composition may also suitably incorporate a liquid carrier for the components (A) and (B) and optionally (C), (D) and/or (E) Suitable carriers include liquid hydrocarbons, for example kerosene Alternatively, diesel fuel itself may be used as a carrier
  • Additives such as antifoams, for example polysilicone based compounds, corrosion inhibitors, for example carboxylic acids, amines, amides and amine salts of carboxylic acids, wax crystal modifiers/distillate flow improvers, etc , may be incorporated if desired
  • the fuel-soluble composition may be incorporated into the fuel during its manufacture Alternatively the composition may be blended into additive-free fuel contained in the fuel storage tanks of individual vessels
  • the present invention provides a marine diesel fuel composition suitable for use in a marine diesel engine which composition comp ⁇ ses a marine diesel fuel of a quality capable of giving rise to liner lacquering and a liner lacquering reducing amount of a fuel-soluble composition as hereinbefore described
  • a further aspect of the invention comprises the use of a fuel-soluble composition as describe above to reduce liner lacquering in a marine diesel engine
  • the invention will now be further illustrated by reference to the following Examples Example 1
  • the lubricating oil consumption of an SWD 240 engine fitted in a Dutch fishing vessel burning an additive-fiee diesel fuel was measured A value of 300 litres/week was l ecorded, which value is consistent with liner lacquering
  • a package comprising a polyisobutene succimmide detergent and a combustion improver derived from cerium and a sulphonic acid
  • the formulation of the package was as follows 18 8% polyisobutene succinimide 17 1% dodecyl phenol (detergent) 5 0% cerium sulphonate (combustion improver)
  • the dose was 800 ppm m/m (mg/kg), equating to a level of total detergent in the fuel of about 290ppm, (about I SOppm of succinimide) and a level of combustion improver of 40ppm
  • Example 2 the dose of package was 650ppm, and it can be seen that by 1000 hours after addition of the package the consumption had fallen from about 1 2 g/bhp hr to 0 8 g/bhp hi ( 1 l g/kW hr)
  • Example 3 the dose of package was 700ppm, and it can be seen that by 1000 hours attei addition ot the package the consumption had fallen from about 1 1 g/bhp hi to 0 83 g/bhp hr ( 1 lg/kW hr)
  • Example 4 the dose of package was 1200ppm, and 300 hours after addition of the package the consumption had fallen from about 2 2 g/bhp hr to about 0 8 g/bhp hr ( 1 I g/kW hr)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

La présente invention a pour objet un procédé visant à réduire le dépôt de laque sur les chemises des cylindres d'un moteur diesel marin, ledit procédé consistant à ajouter au carburant une quantité réduisant le dépôt de laque sur les chemises d'une composition soluble dans le carburant contenant: (A) au moins un détergent pour diesel, et (B) au moins un agent améliorant la combustion. Le détergent sera de préférence un imide ou un imide formé par réation d'un agent d'acylation succinique substitué polyalkène et d'un amine, en particulier un succinimide, et l'agent améliorant la combustion sera de préférence un composé d'oxyde de cérium.
PCT/GB1997/001380 1996-05-20 1997-05-19 Procede pour moteur diesel marin et carburant correspondant WO1997044414A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29077/97A AU2907797A (en) 1996-05-20 1997-05-19 Marine diesel process and fuel therefor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9610563.0 1996-05-20
GBGB9610563.0A GB9610563D0 (en) 1996-05-20 1996-05-20 Marine diesel process and fuel therefor

Publications (1)

Publication Number Publication Date
WO1997044414A1 true WO1997044414A1 (fr) 1997-11-27

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WO (1) WO1997044414A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999035217A1 (fr) * 1998-01-10 1999-07-15 Lubrizol Adibis Holdings (Uk) Limited Composition de carburant
WO2001088069A1 (fr) * 2000-05-16 2001-11-22 Infineum International Limited Utilisation d'additifs pour un fonctionnement de moteur ameliore
WO2001088362A1 (fr) * 2000-05-16 2001-11-22 Infineum International Limited Procede d'exploitation de moteurs diesel
WO2002012417A1 (fr) * 2000-08-03 2002-02-14 Cesare Pedrazzini Additif utilise pour reduire la formation de particules dans des emissions provenant de la combustion du diesel
EP1344809A1 (fr) * 2002-03-13 2003-09-17 Infineum International Limited Compositions additives pour combustible diesel pour l'amélioration de pièges à particules
WO2004065529A1 (fr) * 2003-01-23 2004-08-05 Oxonica Limited Nanoparticles d'oxyde de cerium utilisees en tant qu'additifs pour carburant
WO2007128954A1 (fr) * 2006-04-06 2007-11-15 Oxonica Energy Ltd Biocarburant
US7775166B2 (en) 2007-03-16 2010-08-17 Afton Chemical Corporation Method of using nanoalloy additives to reduce plume opacity, slagging, fouling, corrosion and emissions
EP2292722A1 (fr) 2002-03-28 2011-03-09 The Lubrizol Corporation Procédé de fonctionnement de moteur à combustion interne par l'introduction de détergent dans une chambre de combustion
US7967876B2 (en) * 2006-08-17 2011-06-28 Afton Chemical Corporation Nanoalloy fuel additives
US8741821B2 (en) 2007-01-03 2014-06-03 Afton Chemical Corporation Nanoparticle additives and lubricant formulations containing the nanoparticle additives
EP1512736B1 (fr) 2003-09-05 2018-05-02 Infineum International Limited Compositions d'additifs stabilisées pour carburants diesel
US10443006B1 (en) 2018-11-27 2019-10-15 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US10597594B1 (en) 2018-11-27 2020-03-24 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US10781391B2 (en) 2018-11-27 2020-09-22 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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WO1996015209A1 (fr) * 1994-11-16 1996-05-23 Bp Chemicals (Additives) Limited Procede utile pour reduire le depot de laque sur les chemises de cylindres dans un moteur diesel marin
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FR2359199A1 (fr) * 1976-07-22 1978-02-17 Gamlen Naintre Sa Derives oleosolubles de metaux de terres rares utiles comme adjuvants de combustion dans les moteurs diesel
FR2585360A1 (fr) * 1985-07-29 1987-01-30 Rosenbluth Germain Procede de reduction des imbrules de combustion et agent pour sa mise en oeuvre
EP0423744A1 (fr) * 1985-08-16 1991-04-24 The Lubrizol Corporation Produits combustibles
EP0368834A1 (fr) * 1988-10-03 1990-05-16 Lang & Co., chemisch-technische Produkte Kommanditgesellschaft Catalyseur de combustion aqueux et combustible
FR2637909A1 (fr) * 1988-10-18 1990-04-20 Rouet Jean Additifs de combustion comportant des derives metalliques, leur procede de fabrication et leur utilisation
EP0417990A1 (fr) * 1989-09-11 1991-03-20 Ethyl Petroleum Additives, Inc. Succinimides et leur utilisation en tant qu'additifs pour combustible
EP0435631A1 (fr) * 1989-12-22 1991-07-03 Ethyl Petroleum Additives Limited Compositions de combustible diesel
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EP0575189A1 (fr) * 1992-06-17 1993-12-22 Rhone-Poulenc Chemicals Limited Composés de cérium IV organiques et leur préparation et utilisation
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WO1996026255A1 (fr) * 1995-02-24 1996-08-29 Rhone-Poulenc Chimie Utilisation d'un compose de cerium pour la protection des moteurs a combustion interne

Cited By (22)

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Publication number Priority date Publication date Assignee Title
US6235068B1 (en) 1998-01-10 2001-05-22 The Lubrizol Corporation Fuel composition
WO1999035217A1 (fr) * 1998-01-10 1999-07-15 Lubrizol Adibis Holdings (Uk) Limited Composition de carburant
KR100757617B1 (ko) * 2000-05-16 2007-09-10 인피늄 인터내셔날 리미티드 엔진 작동을 개선시키기 위한 첨가제의 용도
WO2001088069A1 (fr) * 2000-05-16 2001-11-22 Infineum International Limited Utilisation d'additifs pour un fonctionnement de moteur ameliore
WO2001088362A1 (fr) * 2000-05-16 2001-11-22 Infineum International Limited Procede d'exploitation de moteurs diesel
WO2002012417A1 (fr) * 2000-08-03 2002-02-14 Cesare Pedrazzini Additif utilise pour reduire la formation de particules dans des emissions provenant de la combustion du diesel
JP2004506067A (ja) * 2000-08-03 2004-02-26 ペドラッツィーニ　　チェサレ ディーゼル油の燃焼によって生じる排気中の煤塵を低減するための添加剤及びそれを含有する燃料組成物
US7524338B2 (en) 2000-08-03 2009-04-28 Cesare Pedrazzini Additive for reducing particulate in emissions deriving from the combustion of diesel oil or fuel oil having a metallic oxidation catalyst, at least one organic nitrate, and a dispersing agent
EP1344809A1 (fr) * 2002-03-13 2003-09-17 Infineum International Limited Compositions additives pour combustible diesel pour l'amélioration de pièges à particules
KR100992272B1 (ko) * 2002-03-13 2010-11-05 인피늄 인터내셔날 리미티드 미립자 트랩을 개선시키기 위한 디젤 연료 첨가제 조성물
EP2292722A1 (fr) 2002-03-28 2011-03-09 The Lubrizol Corporation Procédé de fonctionnement de moteur à combustion interne par l'introduction de détergent dans une chambre de combustion
WO2004065529A1 (fr) * 2003-01-23 2004-08-05 Oxonica Limited Nanoparticles d'oxyde de cerium utilisees en tant qu'additifs pour carburant
AU2004205788B2 (en) * 2003-01-23 2010-09-02 Energenics Europe Limited Cerium oxide nanoparticles as fuel additives
EP1512736B1 (fr) 2003-09-05 2018-05-02 Infineum International Limited Compositions d'additifs stabilisées pour carburants diesel
WO2007128954A1 (fr) * 2006-04-06 2007-11-15 Oxonica Energy Ltd Biocarburant
US7967876B2 (en) * 2006-08-17 2011-06-28 Afton Chemical Corporation Nanoalloy fuel additives
US8741821B2 (en) 2007-01-03 2014-06-03 Afton Chemical Corporation Nanoparticle additives and lubricant formulations containing the nanoparticle additives
US7775166B2 (en) 2007-03-16 2010-08-17 Afton Chemical Corporation Method of using nanoalloy additives to reduce plume opacity, slagging, fouling, corrosion and emissions
US10443006B1 (en) 2018-11-27 2019-10-15 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US10597594B1 (en) 2018-11-27 2020-03-24 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US10781391B2 (en) 2018-11-27 2020-09-22 Exxonmobil Research And Engineering Company Low sulfur marine fuel compositions
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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GB9610563D0 (en) 1996-07-31

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