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WO2015153160A1 - Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux - Google Patents

Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux Download PDF

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Publication number
WO2015153160A1
WO2015153160A1 PCT/US2015/021949 US2015021949W WO2015153160A1 WO 2015153160 A1 WO2015153160 A1 WO 2015153160A1 US 2015021949 W US2015021949 W US 2015021949W WO 2015153160 A1 WO2015153160 A1 WO 2015153160A1
Authority
WO
WIPO (PCT)
Prior art keywords
amount
earth metal
alkaline earth
reaction
oil
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.)
Ceased
Application number
PCT/US2015/021949
Other languages
English (en)
Inventor
Mohamed G. Fahmy
Roger L. PARSONS
Lindsey K. CONANT
Darren J. BECKER
Jeremy T. STRAUCH
Rodney J. LUKASZEWSKI
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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 Lubrizol Corp filed Critical Lubrizol Corp
Priority to CN201580029206.XA priority Critical patent/CN106687569A/zh
Priority to US15/301,674 priority patent/US20170015925A1/en
Priority to EP15716918.6A priority patent/EP3126476A1/fr
Priority to SG11201608327TA priority patent/SG11201608327TA/en
Priority to CA2944879A priority patent/CA2944879A1/fr
Publication of WO2015153160A1 publication Critical patent/WO2015153160A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G99/00—Subject matter not provided for in other groups of this subclass
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the metal compounds are delivered as metal salts.
  • the anionic portion of the salt can be hydroxide, oxide, carbonate, borate, or nitrate.
  • the reaction mixture will be subjected to treatment with steam.
  • the alkylphenate composition thus prepared will be heated to 120 to 280 °C or alternatively 200 to 250°C, or 210 to 230, or 216 to 240°C, and steam will be supplied thereto.
  • the steam may be provided at superatmospheric pressure and at a temperature of 120 °C to 250 °C, or alternatively 190-240°C, but in any event should be supplied as steam and not as liquid water.
  • Supplying the steam at superatmospheric pressure means that the steam may be provided from a source of steam at superatmospheric pressure; the actual contact between the steam and the reaction mixture is not necessarily conducted at superatmospheric pressure.
  • a single detergent that of the disclosed technology
  • multiple detergents may be present. If there are multiple detergents, the additional detergents may be additional phenate detergents, or they may be detergents of other types.
  • An example of another type of detergent is a sulfonate detergent, prepared from a sulfonic acid. Suitable sulfonic acids include sulfonic and thiosulfonic acids, including mono or polynuclear aromatic or cycloaliphatic compounds. Certain oil-soluble sulfonates can be represented
  • the sulfonate detergent may be a predominantly linear alkylbenzenesulfonate detergent having a metal ratio of at least 8 as described in paragraphs [0026] to [0037] of US Patent Application 2005-065045.
  • the linear alkyl group may be attached to the benzene ring anywhere along the linear chain of the alkyl group, but often in the 2, 3 or 4 position of the linear chain, and in some instances predominantly in the 2 position.
  • Salixarate detergents are overbased materials that can be represented by a compound comprising at least one unit of formula (I) or formula (II) and each end of the compound having a terminal group of formula (III) or (IV):
  • Glyoxylate detergents are similar overbased materials which are based on an anionic group which, in one embodiment, may have the structure
  • each R is independently an alkyl group containing at least 4 or 8 carbon atoms, provided that the total number of carbon atoms in all such R groups is at least 12 or 16 or 24.
  • each R can be an olefin polymer substituent.
  • the acidic material upon from which the overbased glyoxylate detergent is prepared is the condensation product of a hydroxyaromatic material such as a hydrocarbyl-substituted phenol with a carboxylic reactant such as glyoxylic acid or another omega-oxoalkanoic acid.
  • Another class of ashless dispersant is high molecular weight esters, prepared by reaction of a hydrocarbyl acylating agent and a polyhydric aliphatic alcohol such as glycerol, pentae- rythritol, or sorbitol. Such materials are described in more detail in U.S. Patent
  • Antioxidants encompass phenolic antioxidants, which may comprise a butyl substituted phenol containing 2 or 3 t-butyl groups. The para position may also be occupied by a hydrocarbyl group, an ester- containing group, or a group bridging two aromatic rings. Antioxidants also include aromatic amine, such as nonylated diphenylamines or (optionally alkylated) phenyl- nap hthyl amine. Other antioxidants include sulfurized olefins, titanium compounds, and molybdenum compounds.
  • U.S. Pat. No. 4,285,822 discloses lubricating oil compositions containing a molybdenum and sulfur containing composition.
  • lubricating oils include pour point depressing agents, extreme pressure agents, color stabilizers and anti-foam agents.
  • the lubricant may comprise at least one of a supplemental overbased detergent, a dispersant, an antioxidant, a viscosity improver, an anti-wear agent, a pour point depressant, or an extreme pressure agent.
  • Lubricants containing the materials of the disclosed technology may be used for the lubrication of a wide variety of mechanical devices, including internal combustion engines, both two-stroke cycle and four-stroke cycle, spark-ignited and compres- sion-ignited, sump-lubricated or non-sump-lubricated.
  • the engines may be run on a variety fuels including gasoline, diesel fuel, alcohols, bio-diesel fuel, and hydrogen, as well as mixtures of these (such as gasoline-alcohol mixtures, e.g., E-10, E-15, E-85).
  • the disclosed lubricants are suitable for use as lubricants for marine diesel engines, particularly as cylinder lubricants.
  • the present technology provides a method for lubricating an internal combustion engine, comprising supplying thereto a lubricant comprising the composition as described herein.
  • the invention is suitable for 2-stroke or 4-stroke engines, including marine diesel engines, such as 2- stroke marine diesel engines.
  • each chemical component described is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, that is, on an active chemical basis, unless otherwise indicated.
  • each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade.
  • Volatile materials are removed from a commercial-scale product correspond- ing to Example 1 , above, by the stripping process described either in Example 2 or Reference Example 3, below:
  • Example 2 A batch of carbon dioxide-treated material is stripped by circulating the batch, originating in a feed tank, though an external heat exchanger and then a flash tank, and finally back to the feed tank, for a period of time referred to as "strip- back."
  • Heat is also applied directly to the stripper feed tank throughout the strip- back phase, until the batch reaches a target temperature of 218-226°C.
  • the flash tank is operated at a target pressure of 8-16 kPa (60-120 mm Hg absolute), with a residence time of approximately 3 minutes.
  • Flow through the flash tank provides 2 to 3 volumet- ric turnovers of the batch through the flash tank during the strip-back phase, over approximately 6 hours. Thereafter, the liquid outflow from the flash tank is redirected to a filter-feed tank, with stripping conditions otherwise maintained.
  • steam is fed to the flash tank via a sub-surface inlet line, at an approximately uniform rate, targeting delivery of approximately 18 parts by weight total steam (based on 100 parts by weight of initial alkylphenol reactant, before sulfur coupling and neutralization/overbasing).
  • the batch is filtered by use of 1 weight% filter aid (FAUC).

Landscapes

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

Abstract

L'invention concerne un alkylphénate soufré surbasifié d'un métal alcalinoterreux préparé en faisant réagir un alkylphénol avec un hydroxyde d'un métal alcalinoterreux ou un oxyde d'un métal alcalinoterreux avec du soufre en présence d'un alkylène glycol ou d'un dialkylène glycol, ou son éther et en présence d'une huile de viscosité lubrifiante, et éventuellement à faire réagir le produit résultant avec du dioxyde de carbone, formant ainsi une composition dans l'huile d'un alkylphénate soufré d'un métal alcalinoterreux. La composition est chauffée et soumise à une extraction à la vapeur puis à une filtration. Le produit résultant présente un débit et une efficacité de filtration plus élevés.
PCT/US2015/021949 2014-04-04 2015-03-23 Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux Ceased WO2015153160A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201580029206.XA CN106687569A (zh) 2014-04-04 2015-03-23 制备硫化的碱土金属十二烷基酚盐的方法
US15/301,674 US20170015925A1 (en) 2014-04-04 2015-03-23 Method for preparing a sulfurized alkaline earth metal dodecylphenate
EP15716918.6A EP3126476A1 (fr) 2014-04-04 2015-03-23 Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux
SG11201608327TA SG11201608327TA (en) 2014-04-04 2015-03-23 Method for preparing a sulfurized alkaline earth metal dodecylphenate
CA2944879A CA2944879A1 (fr) 2014-04-04 2015-03-23 Procede de preparation d'un dodecylphenate soufre d'un metal alcalinoterreux

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201461975256P 2014-04-04 2014-04-04
US61/975,256 2014-04-04

Publications (1)

Publication Number Publication Date
WO2015153160A1 true WO2015153160A1 (fr) 2015-10-08

Family

ID=52875774

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/021949 Ceased WO2015153160A1 (fr) 2014-04-04 2015-03-23 Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux

Country Status (6)

Country Link
US (1) US20170015925A1 (fr)
EP (1) EP3126476A1 (fr)
CN (1) CN106687569A (fr)
CA (1) CA2944879A1 (fr)
SG (1) SG11201608327TA (fr)
WO (1) WO2015153160A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9688939B1 (en) 2016-01-26 2017-06-27 Infineum International Limited Metal detergents
EP3199612A1 (fr) 2016-01-26 2017-08-02 Infineum International Limited Détergents de métaux
EP3205708A1 (fr) 2016-02-15 2017-08-16 Infineum International Limited Détergents de métaux

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US6569818B2 (en) 2000-06-02 2003-05-27 Chevron Oronite Company, Llc Lubricating oil composition
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EP2055761A2 (fr) * 2007-10-31 2009-05-06 Chevron Oronite Company LLC Compositions d'huile lubrifiante comportant un carburant biodiesel et un détergent
WO2010077630A1 (fr) 2008-12-09 2010-07-08 The Lubrizol Corporation Composition lubrifiante contenant un composé issu d'un acide hydroxycarboxylique
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WO2013119623A1 (fr) 2012-02-08 2013-08-15 The Lubrizol Corporation Procédé de préparation d'un dodécylphénate de métal alcalino-terreux sulfuré

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US2501731A (en) 1946-10-14 1950-03-28 Union Oil Co Modified lubricating oil
US2680096A (en) 1951-02-12 1954-06-01 California Research Corp Process for preparing sulfurized polyvalent metal phenates
US2616925A (en) 1951-03-16 1952-11-04 Lubrizol Corp Organic alkaline earth metal complexes formed by use of thiophosphoric promoters
US2616911A (en) 1951-03-16 1952-11-04 Lubrizol Corp Organic alkaline earth metal complexes formed by use of sulfonic promoters
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US2777874A (en) 1952-11-03 1957-01-15 Lubrizol Corp Metal complexes and methods of making same
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US3488284A (en) 1959-12-10 1970-01-06 Lubrizol Corp Organic metal compositions and methods of preparing same
US3256186A (en) 1963-02-12 1966-06-14 Lubrizol Corp Process for producing carbonated basic metal compositions
US3381022A (en) 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
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US6569818B2 (en) 2000-06-02 2003-05-27 Chevron Oronite Company, Llc Lubricating oil composition
US20050065045A1 (en) 2001-11-05 2005-03-24 Wilk Melody A. Sulfonate detergent system for improved fuel economy
US20060079413A1 (en) 2004-10-12 2006-04-13 The Lubrizol Corporation, A Corporation Of The State Of Ohio Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
US20060217271A1 (en) 2005-03-28 2006-09-28 The Lubrizol Corporation Titanium compounds and complexes as additives in lubricants
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EP2055761A2 (fr) * 2007-10-31 2009-05-06 Chevron Oronite Company LLC Compositions d'huile lubrifiante comportant un carburant biodiesel et un détergent
WO2010077630A1 (fr) 2008-12-09 2010-07-08 The Lubrizol Corporation Composition lubrifiante contenant un composé issu d'un acide hydroxycarboxylique
WO2013119623A1 (fr) 2012-02-08 2013-08-15 The Lubrizol Corporation Procédé de préparation d'un dodécylphénate de métal alcalino-terreux sulfuré

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9688939B1 (en) 2016-01-26 2017-06-27 Infineum International Limited Metal detergents
EP3199612A1 (fr) 2016-01-26 2017-08-02 Infineum International Limited Détergents de métaux
EP3205708A1 (fr) 2016-02-15 2017-08-16 Infineum International Limited Détergents de métaux

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CA2944879A1 (fr) 2015-10-08
US20170015925A1 (en) 2017-01-19
SG11201608327TA (en) 2016-11-29
EP3126476A1 (fr) 2017-02-08

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