EP0748365B1 - Überbasische alkyloxybenzolsulfonate als detergentien - Google Patents

Überbasische alkyloxybenzolsulfonate als detergentien Download PDF

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Publication number
EP0748365B1
EP0748365B1 EP95943415A EP95943415A EP0748365B1 EP 0748365 B1 EP0748365 B1 EP 0748365B1 EP 95943415 A EP95943415 A EP 95943415A EP 95943415 A EP95943415 A EP 95943415A EP 0748365 B1 EP0748365 B1 EP 0748365B1
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EP
European Patent Office
Prior art keywords
alkyl
overbased
sulfonate
lubricating oil
alkyl group
Prior art date
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EP95943415A
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English (en)
French (fr)
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EP0748365A4 (de
EP0748365A1 (de
Inventor
William F. King
Richard J. Nelson
Steven G. Lockett
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron Phillips Chemical Co LP
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Chevron Oronite Co LLC
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    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • the present invention relates to an additive especially useful in a marine lubricating oil.
  • British 1,372,532 teaches that mixtures of overbased, alkyl hydroxy benzene sulfonates and alkylsalicylic acids are useful in lubricating oils.
  • the alkyl groups of the sulfonates appear to be attached at either the 1- or 2-position of the alkyl groups.
  • the TBN appears to be about 200.
  • U.S. 4,751,010 teaches that partial sulfonation of alkylphenol results in the formation of an alkyl hydroxy benzene sulfonate that can be overbased using sulfurization and carbonation.
  • the patent is silent as to where the alkyl groups are attached.
  • the TBN appears to be in the range of from 200 to 250.
  • U.S. 5,330,663 and 5,330,664 teach overbased alkylphenoxy sulfonates that have alkyl groups derived from substantially straight-chained olefins that are either internal or alpha. It does not teach using olefins that are partially internal olefins.
  • the present invention provides a lubricating oil having a major amount of base oil of lubricating viscosity; and a minor amount of an overbased, alkyl oxy benzene sulfonate having a TBN of at least 200, preferably at least 250, between 40 wt.% and 80 wt. % of the alkyl group is attached at the 4- position and higher positions of the alkyl group wherein the oxy group is hydroxy, methoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy.
  • Preferably, between 45 wt.% and 70 wt. % of the alkyl group is attached at the 4- position and higher positions of the alkyl group.
  • This lubricating oil is especially useful as a marine lubricating oil.
  • the oxy group is hydroxy
  • the alkyl group of the overbased, alkyl oxy benzene sulfonate has from eighteen to thirty carbon atoms per alkyl group. More preferably, it has from twenty to twenty-four carbon atoms per alkyl group.
  • One process for making this overbased, alkyl oxy benzene sulfonate comprises alkylating an oxy benzene with an olefin between 40 wt.% and 80 wt. % internal olefins to produce an alkyl oxy benzene wherein the oxy group is hydroxy, methoxy, propoxy, butoxy, pentoxy or hexoxy, then sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid; and overbasing the alkyl oxy benzene sulfonic acid to produce the overbased, alkyl oxy benzene sulfonate.
  • the internal olefin is produced by isomerizing an olefin using an iron pentacarbonyl catalyst.
  • the present invention involves highly overbased, alkyl oxy benzene sulfonate detergents where at least 40 wt.% of the alkyl groups are attached at the 4- position and higher positions of the alkyl group.
  • the viscosity is lowered significantly.
  • At least 20 wt.% of the alkyl groups should be attached at the 1-, 2-, and 3- position in order to reduce high temperature deposit formation. While Applicants do not wish to be bound by any particular theory of operation, it is believed that too high of internal attachment leads to structures that are similar to materials derived from branched olefins. Such materials tend to decompose readily at the branching.
  • between 40 wt.% and 80 wt. % (preferably between 45 wt.% and 70 wt. %) of the alkyl group is attached at the 4-position and higher positions of the alkyl group.
  • This type of additive can be produced by alkylating an oxy benzene with an olefin containing between between 40 wt.% and 80 wt.
  • An olefin containing between 20 wt.% and 60 wt. % internal olefins can be formed by isomerizing an alpha olefin using an iron pentacarbonyl catalyst.
  • the present invention comes out of work in trying to find an inexpensive alternative to the use of salicylates in lube oils for marine applications. That alternative should have a TBN of over 250, have a viscosity of less than 6 cm 2 /s (600 cSt), and have comparative properties with commercial salicylates.
  • the lubricating oil has a minor amount of an overbased, alkyl oxy benzene sulfonate having a TBN of at least 200, preferably at least 250, wherein at least 40 wt.% of the alkyl group of the sulfonate is attached at the 4- position and higher positions of the alkyl group.
  • the oxy group can be either hydroxy, methoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy. Preferably, it is hydroxy.
  • TBN Total Base Number
  • Total Base Number refers to the amount of base equivalent to one milligram of KOH in one gram of additive.
  • internal olefins we mean an olefin wherein the double bond is at the 4- position and higher positions of the alkene, instead of at the 1-, 2-, or 3- position.
  • the alkyl group of the overbased, alkyl oxy benzene sulfonate has from eighteen to thirty carbon atoms per alkyl group. More preferably, the alkyl group has from twenty to twenty-four carbon atoms per alkyl group.
  • the additive of the present invention can be produced by alkylating an oxy benzene with an olefin containing between 40 wt.% and 80 wt. % internal olefins to produce an alkyl oxy benzene, sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid; and overbasing the alkyl oxy benzene sulfonic acid to produce the overbased, alkyl oxy benzene sulfonate.
  • An olefin containing between 40 wt.% and 80 wt. % internal olefins can be formed by isomerizing an alpha olefin using an iron pentacarbonyl catalyst.
  • a neutralized slurry of alkyl oxy benzene sulfonic acid is added to a slurry of xylenes, methanol, and calcium hydroxide.
  • the resulting slurry is then carbonated during which a second slurry of alkyl oxy benzene sulfonic acid and a second slurry of xylenes, methanol, and calcium hydroxide are added.
  • the material is stripped to remove methanol and water.
  • Lube oil is then added and the solids removed. The remainder of the solvents are then stripped off and additional lube oil added to adjust the product to the final base number.
  • the oil-soluble, highly overbased, alkyl oxy benzene sulfonate additive compositions produced by the process of this invention are useful lubricating oil additives imparting detergency and dispersency properties when added to the lubricating oil composition employed in the crank case of an internal combustion engine.
  • Such lubricating oil compositions comprise a major amount of base oil of lubricating viscosity; and a minor amount of oil-soluble, highly overbased, alkyl oxy benzene sulfonate additive compositions.
  • These lubricating oil compositions are useful in diesel engines, gasoline engines, as well as in marine engines.
  • Such lubricating oil compositions employ a finished lubricating base oil oil of lubricating viscosity which may be single or multigrade.
  • Multigrade lubricating base oils are prepared by adding viscosity index (VI) improvers.
  • Typical viscosity index improvers are polyalkyl methacrylates, ethylene and propylene copolymers, styrene-diene copolymers, and the like.
  • the lubricating base oils used in such compositions may be mineral oils or synthetic oils of viscosity suitable for use in the crank case of an internal combustion engine such as gasoline engines and diesel engines which include marine engines.
  • Crank case lubricating oils ordinarily have a viscosity of about 13 cm 2 /s (1300 cSt) at -18°C (0° F) to 0.24 cm 2 /s (24 cSt) at 99°C (210° F).
  • the lubricating base oils may be derived from synthetic or natural sources.
  • Mineral oils for use as the base oil in the invention includes paraffinic, naphthenic and other oils that are ordinarily used in lubricating oil compositions. Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
  • Useful synthetic hydrocarbon oils include liquid polymers of ⁇ -olefins having the proper viscosity. Especially useful are the hydrogenated liquid oligomers of C 6 to C 12 ⁇ -olefins such as 1-decene trimer. Likewise, alkylbenzenes of proper viscosity such as didodecyl benzene, can be used.
  • Useful synthetic esters include esters of both monocarboxylic acids and polycarboxylic acids as well as monohydroxy alkenols and polyols.
  • Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate and the like.
  • Complex esters prepared from mixtures of mono and dicarboxylic acid and mono and dihydroxy alkanols can also be used,
  • Blends of hydrocarbon oils with synthetic oils are also useful. For example, blends of 10 to 25 wt. % hydrogenated 1-decene trimer with 75 to 90 wt. % 3210 cm 2 /s at 38°C (150 SUS at 100°F) mineral oil gives an excellent lubricating base oil.
  • the lubricating oil also has an ashless dispersant and a zinc dialkyldithiophosphate.
  • the lubricating oil also has a detergent selected from the group consisting of metal phenates, metal sulfonates, and metal salicylates.
  • additives which may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors, metal deactivators, pour point depressants, anti-oxidants, and a variety of other well-known additives
  • High overbased alkyl hydroxy benzene sulfonates were prepared using an alkylphenol derived by contacting 3.0 moles of phenol per each mole of a normal C 20 to C 24 ⁇ -olefin mixture using Amberlyst-36 catalyst [a polystyrene cross-linked sulfonic acid resin having a Hammett acid function (H o ) of less than -2.2 and an acid number of 5.4 milliequivalents per gram].
  • Amberlyst-36 (trade mark) resin catalyst is commercially available from Rohm & Haas, Philadelphia, PA.
  • the olefin mixture had the following olefinic positions, determined by using a macro program using Nuclear Magnetic Resonance Spectroscopy (NMR). wt. % Alpha wt. % Beta wt. % Internal wt. % Tri-substituted 89.1 0.5 1.4 0.3
  • the alkylation reactions were conducted at 100° C using a batch alkylation unit The reaction time was six hours. Afterwards, the alkylated phenol was recovered by filtering and then stripping the excess phenol from the product stream at 400° F and 133 Pa (abs) (1 torr). The recovered alkylphenol products were analyzed for monoalkyl and dialkyl content and ortho/para substitution by superfluid chromatography (SFC) and fourier transform infrared spectroscopy (FT-IR) respectively.
  • SFC superfluid chromatography
  • FT-IR Fourier transform infrared spectroscopy
  • the alkylated phenol was sulfonated using a falling film reactor. Reaction conditions were as follows:
  • Cyclohexamine analysis for this product indicates that a sulfonate as Ca value of 3.79 wt. % was obtained.
  • the reactor was equipped with a condenser for stripping and the temperature was ramped to 93°C (200° F) over two hours. At 93°C (200° F), the temperature was then ramped to 132°C (270° F) over 30 minutes. At 132°C (270° F), 215 grams of 100 Neutral oil was added and the entire batch was then filtered through a Buchner filter. The filtrate was then stripped to 204°C (400° F) at 5.3 kPa (abs) (40mm Hg vacuum). The base number was then measured with a resulting number of 318. An additional 45 grams of 100 Neutral oil was added to adjust the base number to 312.5.
  • the final product had a viscosity that was too viscous to measure at 100° C at a TBN of 312.5. It had 22.37% of the alkyl group of the sulfonate attached at the 4- position and higher positions of the alkyl group.
  • the final product had a viscosity of 5.8 cm 2 /s (581 cSt) at 100° C at a TBN of 300. It had 49.33 % of the alkyl group of the sulfonate attached at 4- position and higher positions of the alkyl group.
  • the procedures of the Comparative Example were repeated using a polyalpha olefin derived from C 10 dimer.
  • the polyalpha olefin had the following olefinic positions, determined by using a macro program using NMR. wt. % Alpha wt. % Beta wt. % Internal wt. % Tri-substituted 14.0 13.4 29.8 56.0
  • the final product had a viscosity of 1.1 cm 2 /s (109 cSt) at 100° C at a TBN of 296. It had 28.45 % of the alkyl group of the sulfonate attached at 4- position and higher positions of the alkyl group.
  • wt.% is based on the amount of an active component, namely, with neither process oil nor diluent oil.
  • the phenoxy sulfonate employed is that described in Example 1.
  • I. Marine Diesel Engine Oils 1) Phenoxy sulfonate 65.0 wt.% Primary alkyl Zn-DTP 5.9 wt.% Diluent oil 29.1 wt.% 2) Phenoxy sulfonate 64.0 wt.% Alkenylsuccinimide ashless dispersant 6.3 wt.% Diluent oil 29.7 wt.% 3) Phenoxy sulfonate 59.0 wt.% Primary alkyl Zn-DTP 5.4 wt.% Alkenylsuccinimide ashless dispersant 5.9 wt.% Diluent oil 29.7 wt.% 4) Phenoxy sulfonate 63.6 wt.% Phenol type oxidation

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Claims (16)

  1. Additiv, umfassend ein überbasisches Alkyloxybenzolsulfonat mit einer TBN von mindestens 200, wobei zwischen 40 und 80 Gew.% des Alkylrests an der Position 4 und höheren Positionen des Alkylrests gebunden sind, und wobei die Oxygruppe ausgewählt ist aus der Gruppe Hydroxy, Methoxy, Ethoxy, Propoxy, Butoxy, Pentoxy und Hexoxy.
  2. Additiv nach Anspruch 1, wobei das überbasische Alkyloxybenzolsulfonat eine TBN von mindestens 250 hat.
  3. Additiv nach Anspruch 1 oder 2, wobei zwischen 45 und 70 Gew.% des Alkylrests an der Position 4 und höheren Positionen des Alkylrests gebunden sind.
  4. Additiv nach einem der Ansprüche 1 bis 3, wobei die Oxygruppe Hydroxy ist.
  5. Additiv nach einem der Ansprüche 1 bis 4, wobei der Alkylrest 18 bis 30 Kohlenstoffatome je Alkylrest aufweist.
  6. Additiv nach Anspruch 5, wobei der Alkylrest 20 bis 24 Kohlenstoffatome je Alkylrest aufweist.
  7. Verfahren zur Herstellung eines Additivs nach Anspruch 1, umfassend:
    (a) Alkylieren eines Oxybenzols mit einem Olefin, das zwischen 40 und 80 Gew.% innere Olefine aufweist, so dass man ein Alkyloxybenzol erzeugt, wobei die Oxygruppe ausgewählt ist Hydroxy, Methoxy, Ethoxy, Propoxy, Butoxy, Pentoxy und Hexoxy;
    (b) Sulfonieren des Alkyloxybenzols, so dass man eine Alkyloxybenzolsulfonsäure erzeugt; und
    (c) Überalkalisieren der Alkyloxybenzolsulfonsäure, so dass man das überbasische Alkyloxybenzolsulfonat erzeugt.
  8. Verfahren nach Anspruch 7, wobei man das in Schritt
    (a) eingesetzte Olefin durch Isomerisation eines Olefins mit einem Eisenpentacarbonyl-Katalysator erhält.
  9. Schmieröl-Zusammensetzung, umfassend:
    (a) eine größere Menge Basisöl mit Schmierviskosität; und
    (b) eine kleinere Menge Additiv nach einem der Ansprüche 1 bis 6.
  10. Schmierölzusammensetzung nach Anspruch 9, die zudem ein aschefreies Dispersionsmittel und ein Zinkdialkyldithiophosphat enthält.
  11. Schmierölzusammensetzung nach Anspruch 9 oder 10, die zudem einen Viskositätszahl-Verbesserer enthält.
  12. Schmierölzusammensetzung nach Anspruch 9, 10 oder 11, die zudem ein aus Metallphenaten, Metallsulfonaten und Metallsalicylaten ausgewähltes Detergens enthält.
  13. Schmierölzusammensetzung nach Anspruch 9, 10, 11, oder 12, welche ein Schiffsmotor-Schmieröl ist.
  14. Verfahren zur Herstellung des Schmieröls nach Anspruch 9, umfassend das Vereinigen einer größeren Menge Basisöl mit Schmierviskosität und eine kleinere Menge Additiv nach einem der Ansprüche 1 bis 6.
  15. Verwendung der Schmierölzusammensetzung nach einem der Ansprüche 9 bis 14 in einem Diesel- oder Benzinmotor.
  16. Verwendung nach Anspruch 15, wobei der Motor ein Schiffsmotor ist.
EP95943415A 1994-12-28 1995-12-07 Überbasische alkyloxybenzolsulfonate als detergentien Expired - Lifetime EP0748365B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US365272 1989-06-12
US36527294A 1994-12-28 1994-12-28
PCT/US1995/016162 WO1996020265A1 (en) 1994-12-28 1995-12-07 Overbased alkyl oxy benzene sulfonates as detergents

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EP0748365A4 EP0748365A4 (de) 1998-12-16
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FR2774387B1 (fr) * 1998-02-02 2000-12-01 Elf Antar France Lubrifiant marin pour moteur deux temps
EP0945499B1 (de) * 1998-03-26 2011-05-11 Chevron Oronite Company LLC Schmiermittelzusammensetzungen zur Verwendung in mittelschnell laufenden Dieselmotoren
JP2000192069A (ja) * 1998-12-28 2000-07-11 Oronite Japan Ltd ディ―ゼル内燃機関用潤滑油組成物及び添加剤組成物
US6551965B2 (en) * 2000-02-14 2003-04-22 Chevron Oronite Company Llc Marine diesel engine lubricating oil composition having improved high temperature performance
GB0011115D0 (en) 2000-05-09 2000-06-28 Infineum Int Ltd Lubricating oil compositions
EP1298189A1 (de) * 2001-09-28 2003-04-02 Infineum International Limited Schmiermittelzusammensetzungen für Schiffsdieselmotoren
EP1298190B1 (de) * 2001-09-28 2005-10-12 Infineum International Limited Schmiermittelzusammensetzungen für Schiffsdieselmotoren
JP4787016B2 (ja) * 2005-12-28 2011-10-05 シェブロンジャパン株式会社 ディーゼル内燃機関用潤滑油組成物
US7875577B2 (en) * 2005-12-28 2011-01-25 Chevron Japan Ltd. Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines
US8778856B2 (en) * 2009-12-02 2014-07-15 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same

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GB709587A (en) * 1951-01-29 1954-05-26 Bataafsche Petroleum Lubricating oil compositions
US3523898A (en) * 1966-04-05 1970-08-11 Phillips Petroleum Co Increased base number metal petroleum sulfonate and process for its preparation
FR2584414B1 (fr) * 1985-07-08 1987-10-30 Orogil Nouveaux additifs detergents-dispersants sulfones et sulfurises pour huiles lubrifiantes
US5330663A (en) * 1992-09-02 1994-07-19 Chevron Research And Technology Company Neutral and low overbased alkylphenoxy sulfonate additive compositions
US5320762A (en) * 1993-03-12 1994-06-14 Chevron Research And Technology Company Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions

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CA2184159A1 (en) 1996-07-04
EP0748365A1 (de) 1996-12-18
DE69531043T2 (de) 2003-12-04
DE69531043D1 (de) 2003-07-17
WO1996020265A1 (en) 1996-07-04
JPH09511015A (ja) 1997-11-04

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