EP0748365B1 - Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents - Google Patents
Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents Download PDFInfo
- 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
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- overbased
- sulfonate
- lubricating oil
- alkyl group
- 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.)
- Expired - Lifetime
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- C10M129/04—Hydroxy compounds
- C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Claims (16)
- Additif comprenant un alkyloxybenzènesul fonate surbasique ayant un indice de basicité total IBT d'au moins 200, dans lequel 40 % en poids à 80 % en poids du groupe alkyle sont fixés en position 4 et en positions supérieures du groupe alkyle, et dans lequel le terme oxy est choisi dans le groupe consistant en des groupes hydroxy, méthoxy, éthoxy, propoxy, butoxy, pentoxy et hexoxy.
- Additif suivant la revendication 1, dans lequel l'alkyloxybenzènesulfonate surbasique a un IBT d'au moins 250.
- Additif suivant la revendication 1 ou 2, dans lequel 45 % en poids à 70 % en poids du groupe alkyle sont fixés en position 4 et en positions supérieures du groupe alkyle.
- Additif suivant l'une quelconque des revendications 1 à 3, dans lequel le groupe oxy est un groupe hydroxy.
- Additif suivant l'une quelconque des revendications 1 à 4, dans lequel le groupe alkyle possède 18 à 30 atomes de carbone par groupe alkyle.
- Additif suivant la revendication 5, dans lequel le groupe alkyle possède 20 à 24 atomes de carbone par groupe alkyle.
- Procédé pour la production d'un additif suivant la revendication 1, comprenant les étapes consistant :(a) à alkyler un oxybenzène avec une oléfine comprenant 40 % en poids à 80 % en poids d'oléfines internes pour produire un alkyloxybenzène, dans lequel le groupe oxy est choisi dans le groupe consistant en des groupes hydroxy, méthoxy, éthoxy, propoxy, butoxy, pentoxy et hexoxy ;(b) à sulfoner l'alkyloxybenzène pour produire un acide alkyloxybenzènesulfonique ; et(c) à rendre surbasique l'acide alkyloxybenzènesulfonique pour produire ledit alkyloxybenzènesulfonate surbasique.
- Procédé suivant la revendication 7, dans lequel l'oléfine utilisée dans l'étape (a) est obtenue en isomérisant une oléfine au moyen d'un catalyseur consistant en fer-pentacarbonyle.
- Composition d'huile lubrifiante comprenant :(a) une quantité dominante d'une huile de base de viscosité propre à la lubrification ; et(b) une petite quantité de l'additif suivant l'une quelconque des revendications 1 à 6.
- Composition d'huile lubrifiante suivant la revendication 9, comprenant en outre un dispersant sans cendre et un dialkyldithiophosphate de zinc.
- Composition d'huile lubrifiante suivant la revendication 9 ou 10, comprenant en outre un agent améliorant l'indice de viscosité.
- Composition d'huile lubrifiante suivant la revendication 9, 10 ou 11, comprenant en outre un détergeant choisi dans le groupe consistant en des phénates métalliques, des sulfonates métalliques et des salicylates métalliques.
- Composition d'huile lubrifiante suivant la revendication 9, 10, 11 ou 12, qui est une huile lubrifiante pour moteur marin.
- Procédé pour la préparation de l'huile lubrifiante suivant la revendication 9, procédé qui comprend l'association d'une quantité dominante d'une huile de base de viscosité propre à la lubrification et d'une petite quantité de l'additif suivant l'une quelconque des revendications 1 à 6.
- Utilisation d'une composition d'huile lubrifiante suivant l'une quelconque des revendications 9 à 14 dans un moteur Diesel ou moteur à essence.
- Utilisation suivant la revendication 15, dans laquelle le moteur est un moteur marin.
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 (fr) | 1994-12-28 | 1995-12-07 | Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0748365A1 EP0748365A1 (fr) | 1996-12-18 |
EP0748365A4 EP0748365A4 (fr) | 1998-12-16 |
EP0748365B1 true EP0748365B1 (fr) | 2003-06-11 |
Family
ID=23438179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95943415A Expired - Lifetime EP0748365B1 (fr) | 1994-12-28 | 1995-12-07 | Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0748365B1 (fr) |
JP (1) | JPH09511015A (fr) |
CA (1) | CA2184159A1 (fr) |
DE (1) | DE69531043T2 (fr) |
WO (1) | WO1996020265A1 (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2774387B1 (fr) * | 1998-02-02 | 2000-12-01 | Elf Antar France | Lubrifiant marin pour moteur deux temps |
EP0945499B1 (fr) * | 1998-03-26 | 2011-05-11 | Chevron Oronite Company LLC | Compositions lubrifiantes utilisable dans les moteurs diesel à vitesse moyenne |
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 (fr) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Composition lubrifiante pour la lubrification d'un moteur diesel marin |
EP1298190B1 (fr) * | 2001-09-28 | 2005-10-12 | Infineum International Limited | Compositions lubrifiantes pour la lubrification d'un moteur diesel marin |
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 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
1995
- 1995-12-07 EP EP95943415A patent/EP0748365B1/fr not_active Expired - Lifetime
- 1995-12-07 JP JP8520479A patent/JPH09511015A/ja not_active Ceased
- 1995-12-07 CA CA002184159A patent/CA2184159A1/fr not_active Abandoned
- 1995-12-07 DE DE69531043T patent/DE69531043T2/de not_active Expired - Fee Related
- 1995-12-07 WO PCT/US1995/016162 patent/WO1996020265A1/fr active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
JPH09511015A (ja) | 1997-11-04 |
DE69531043D1 (de) | 2003-07-17 |
DE69531043T2 (de) | 2003-12-04 |
CA2184159A1 (fr) | 1996-07-04 |
EP0748365A4 (fr) | 1998-12-16 |
EP0748365A1 (fr) | 1996-12-18 |
WO1996020265A1 (fr) | 1996-07-04 |
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