EP0102255A1 - Verfahren zur Herstellung von sulfurierten Erdalkalimetallalkylphenaten verwendbar als Schmierölzusatz - Google Patents

Verfahren zur Herstellung von sulfurierten Erdalkalimetallalkylphenaten verwendbar als Schmierölzusatz Download PDF

Info

Publication number: EP0102255A1
Authority: EP; European Patent Office
Prior art keywords: alkaline earth; glycol; molar ratio; alcohol; base
Prior art date: 1982-06-24
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.): Granted

Application number

EP83401269A

Other languages

English (en)

French (fr)

Other versions

EP0102255B1 (de

Inventor

Jean-Louis Le Coent

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.)

Orogil SA

Original Assignee

Orogil SA

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.)

1982-06-24

Filing date

1983-06-20

Publication date

1984-03-07

1983-06-20 Application filed by Orogil SA filed Critical Orogil SA

1983-06-20 Priority to AT83401269T priority Critical patent/ATE22112T1/de

1984-03-07 Publication of EP0102255A1 publication Critical patent/EP0102255A1/de

1986-09-10 Application granted granted Critical

1986-09-10 Publication of EP0102255B1 publication Critical patent/EP0102255B1/de

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 25
239000010687 lubricating oil Substances 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 99
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 50
239000003921 oil Substances 0.000 claims abstract description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
239000000654 additive Substances 0.000 claims abstract description 10
-1 halide ions Chemical class 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
239000013049 sediment Substances 0.000 claims abstract description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
238000009835 boiling Methods 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
238000006386 neutralization reaction Methods 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
238000010790 dilution Methods 0.000 claims description 12
239000012895 dilution Substances 0.000 claims description 12
239000000047 product Substances 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 9
238000004821 distillation Methods 0.000 claims description 9
238000001914 filtration Methods 0.000 claims description 9
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 6
230000000996 additive effect Effects 0.000 claims description 5
NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 4
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
239000007983 Tris buffer Substances 0.000 claims description 2
239000003599 detergent Substances 0.000 claims description 2
239000000706 filtrate Substances 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
239000000920 calcium hydroxide Substances 0.000 claims 1
229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 claims 1
125000003916 ethylene diamine group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 15
229910052791 calcium Inorganic materials 0.000 description 9
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 7
239000011575 calcium Substances 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
235000008733 Citrus aurantifolia Nutrition 0.000 description 6
235000011941 Tilia x europaea Nutrition 0.000 description 6
239000004571 lime Substances 0.000 description 6
125000002947 alkylene group Chemical group 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000000243 solution Substances 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000005987 sulfurization reaction Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000006479 redox reaction Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000011701 zinc Substances 0.000 description 2
XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
GWMWXFGQYATKBA-UHFFFAOYSA-N Cc(cc1S)ccc1O Chemical compound Cc(cc1S)ccc1O GWMWXFGQYATKBA-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000004435 Oxo alcohol Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
235000001465 calcium Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000010710 diesel engine oil Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000010711 gasoline engine oil Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000007788 liquid Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000010705 motor oil Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000010690 paraffinic oil Substances 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical class [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

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
- 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

Definitions

the present invention relates to a new process for the preparation of sulfurized alkylphenates of alkaline earth metals, especially calcium, of high alkalinity and the application of said sulfurized alkylphenates as detergent-dispersant additives for lubricating oils.
a simplified representation of said mixture constituting 1 "sulfurized alkylphenol” can be the following average formula: where X 'varies from 1 to 3 and generally from 1.4 to 2.5
alkaline-earth bases mention may be made of calcium, barium or strontium oxides or hydroxides, and very particularly lime.
the amount of dilution oil that can be used is such that the amount of oil contained in the final product represents from 25 to 65% by weight of said product and preferably from 30 to 50% by weight of said product.
alkanols such as ethylhexanol, oxo alcohol, decyl alcohol, tridecyl alcohol
alkoxyalkanols such as butoxy-2 ethanol, butoxy-2 propanol, methyl ether of dipropylene glycol.
the halide ions are preferably Cl ions; these can be implemented via ammonium chloride or metal chlorides such as calcium chloride, zinc ...
the neutralization operation is favorably carried out at a temperature between 120 and 180 ° C and preferably between 130 and 170 ° C at a pressure slightly lower than atmospheric pressure (930 10 2 Pa - 960 1 0 2 P a).
Said neutralization operation can also be carried out in the presence of an amine, according to a molar ratio of amine / alkaline earth base, which can range up to 0.2.
amines which can be used, mention may be made of: polyalkyleneamines, such as polyethyleneamines and very particularly ethylenediamine and tris (3-oxa-6-amino-6 hexyl) amine.
Said operation is also favorably carried out in the presence of acetic acid in an amount corresponding to a molar ratio of acetic acid / alkaline earth base which can range up to 0.2 and preferably up to 0.1.
distillation operations succeeding the neutralization operation and the possible carbonation operation are carried out so as to remove water, glycol and alkanol.
the carbonation operation is carried out at a temperature between 145 and 180 ° C at a pressure less than or equal to atmospheric pressure (930 10 2 to 1010 10 2 Pa).
the present invention also relates to a variant of the process described above, a variant consisting in preparing "in situ" in the neutralization medium the alkylphenolsulfurized from alkylphenol and sulfur.
the quantity of sulfur used corresponds to a sulfur / alkylphenol molar ratio of between 0.8 and 2.
the sulfurization-neutralization operation is favorably carried out at a temperature between 145 and 175 ° C and preferably between 155 and 170 ° C, optionally in the presence of an amine as above indicated for the general neutralization step.
the carbonation operation is then carried out at a temperature between 155 and 180 ° C and preferably between 165 and 175 ° C, optionally in the presence of halide ions as above indicated.
the present invention also relates to the product obtained according to the process described above as well as its application as an additive to improve the detergent and dispersing properties of lubricating oils.
the amount of additive to be used depends on the future use of said oils. Thus for a gasoline engine oil, the amount of additive to be added is generally between 1 and 2.5 X; for a diesel engine oil it is generally between 1.8 and 4 X, for a marine engine oil, this can go up to 30 X.
the lubricating oils which can thus be improved can be chosen from a wide variety of lubricating oils, such as lubricating oils of naphthenic base, of paraffinic base and of mixed base, of other hydrocarbon lubricants, for example lubricating oils derived from product coal, and synthetic oils, for example alkylene polymers, alkylene oxide type polymers and their derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxide to presence of water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids, liquid esters of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkylbiphenyl ethers, polymers of silicon.
lubricating oils such as lubricating oils of naphthenic base, of paraffinic base and of mixed base, of other hydrocarbon lubricants, for example lubricating oils derived from product coal, and synthetic oils, for example alkylene polymers, alky
Additional additives may also be present in said lubricating oils alongside the detergent-dispersants obtained according to the process of the invention; include, for example, anti-oxidant, anti-corrosion additives, ashless dispersant additives.
the mixture is heated to 160 ° C. and then a mixture of glycol and ethylhexanol is slowly added over 80 minutes, under slight depression.
the vacuum is gradually tightened to 66.5 ⁇ 10 2 Pa.
the mixture is heated to 190 ° C. for 1 hour, then a nitrogen stripping is carried out for 1 hour at 190 ° C.
the finished product is added to a SAE 50 oil with a paraffinic tendency so as to obtain a solution containing 25% of additive.
glycol is added as a mixture with ethylhexanol or 2-butoxyethanol.
the mixture is heated to 145 ° C., then it remains under a vacuum of 345 ⁇ 10 2 Pa for 30 minutes.
a distillate D 1 is collected.
the vacuum is gradually tightened to 66.5 10 2 Pa while heating up to 190 ° C. It remains for one hour at 190 ° C., then stripping is carried out with nitrogen for 1 hour at 190 ° C.
the mixture is heated to 155 ° C. under slight depression (930 10 2 Pa), a first charge of alcohol consisting of a mixture of glycol and butoxyethanol or butoxypropanol is slowly added over 30 minutes, then a second charge of butoxyethanol or butoxypropanol alone in 40 minutes.
the vacuum is gradually tightened to 66.5 ⁇ 10 2 Pa.
the mixture is heated to 190 ° C. for 1 hour, then a nitrogen stripping is carried out for 1 hour at 190 ° C.
a D2 distillate is collected.
Example 13 The operation described in Example 13 is carried out by introducing the mixture of 10 g of glycol and 10 g of butoxyethanol (1st charge) from the start (and not when the temperature reaches 155 ° C.).
Example 12 The operation described in Example 12 is carried out by introducing the 10 g of glycol at the start and then the 10 g of butoxyethanol at 155 ° C.
Example 26 The operation described in Example 26 is carried out using a dodecylphenol containing 7% of sulfur and an additional quantity of sulfur.

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Fats And Perfumes (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Manufacture And Refinement Of Metals (AREA)

EP83401269A 1982-06-24 1983-06-20 Verfahren zur Herstellung von sulfurierten Erdalkalimetallalkylphenaten verwendbar als Schmierölzusatz Expired EP0102255B1 (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT83401269T ATE22112T1 (de)	1982-06-24	1983-06-20	Verfahren zur herstellung von sulfurierten erdalkalimetallalkylphenaten verwendbar als schmieroelzusatz.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8211060		1982-06-24
FR8211060A FR2529226B1 (fr)	1982-06-24	1982-06-24	Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes

Publications (2)

Publication Number	Publication Date
EP0102255A1 true EP0102255A1 (de)	1984-03-07
EP0102255B1 EP0102255B1 (de)	1986-09-10

Family

ID=9275357

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP83401269A Expired EP0102255B1 (de)	1982-06-24	1983-06-20	Verfahren zur Herstellung von sulfurierten Erdalkalimetallalkylphenaten verwendbar als Schmierölzusatz

Country Status (17)

Country	Link
US (1)	US4514313A (de)
EP (1)	EP0102255B1 (de)
JP (1)	JPS5946262A (de)
AT (1)	ATE22112T1 (de)
AU (1)	AU557851B2 (de)
BR (1)	BR8303347A (de)
CA (1)	CA1182628A (de)
DE (1)	DE3366063D1 (de)
DK (1)	DK162398C (de)
ES (1)	ES523542A0 (de)
FR (1)	FR2529226B1 (de)
GB (1)	GB2123022B (de)
GR (1)	GR78596B (de)
MX (1)	MX26983A (de)
PH (1)	PH19427A (de)
PT (1)	PT76930B (de)
ZA (1)	ZA834555B (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0095322A3 (en) *	1982-05-22	1984-09-05	Orobis Limited	Process for the production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
FR2587353A1 (fr) *	1985-09-17	1987-03-20	Orogil	Nouveaux additifs detergents-dispersants suralcalinises stables a l'hydrolyse pour huiles lubrifiantes et leur procede de preparation
EP0577338A3 (en) *	1992-06-27	1994-06-01	Bp Chemicals Additives	Alkaline earth metal sulphurised hydrocarbyl phenate-containing additive concentrate, process for its production and use thereof

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2564830B1 (fr) *	1984-05-25	1986-09-19	Orogil	Procede de preparation d'alkylaryl sulfonates de metaux alcalino-terreux a partir d'acides alkylaryl sulfoniques lineaires et additifs detergents-dispersants pour huiles lubrifiantes ainsi obtenus
DE3676384D1 (de) *	1985-08-13	1991-02-07	Exxon Chemical Patents Inc	Ueberbasische zusaetze.
US4776969A (en) *	1986-03-31	1988-10-11	Exxon Chemical Patents Inc.	Cyclic phosphate additives and their use in oleaginous compositions
NZ221128A (en) *	1986-08-08	1989-09-27	Chevron Res	Overbased sulphurised alkylphenols as lube oil additives
GB8621343D0 (en) *	1986-09-04	1986-10-15	Exxon Chemical Patents Inc	Overbased alkali metal additives
JPH04183792A (ja) *	1990-11-19	1992-06-30	Idemitsu Kosan Co Ltd	過塩基性硫化アルカリ土類金属フェネート及びその用途
US5292443A (en) *	1992-08-21	1994-03-08	Texaco Inc.	Process for producing neutralized sulfurized alkylphenate lubricant detergent additive
US5529705A (en) *	1995-03-17	1996-06-25	Chevron Chemical Company	Methods for preparing normal and overbased phenates
US5759966A (en) *	1996-10-01	1998-06-02	Chevron Chemical Company	High overbased metal sulfurized alkyphenates
RU2179996C1 (ru) *	2000-11-30	2002-02-27	Открытое акционерное общество "Всероссийский научно-исследовательский институт по переработке нефти"	Способ получения присадки к смазочным маслам
US20030195126A1 (en) *	2002-04-12	2003-10-16	Boons Cornelis Hendrikus Maria	Carboxylated detergent-dispersant-containing compositions having improved properties in lubricating oils
US20040235682A1 (en) *	2003-05-22	2004-11-25	Chevron Oronite Company Llc	Low emission diesel lubricant with improved corrosion protection
US7163911B2 (en) *	2003-05-22	2007-01-16	Chevron Oronite Company Llc	Carboxylated detergent-dispersant additive for lubricating oils
US7435709B2 (en) *	2005-09-01	2008-10-14	Chevron Oronite Company Llc	Linear alkylphenol derived detergent substantially free of endocrine disruptive chemicals
US8399388B2 (en)	2009-07-01	2013-03-19	Chevron Oronite Company Llc	Low temperature performance lubricating oil detergents and method of making the same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1382559A (fr) *	1963-02-12	1964-12-18	Lubrizol Corp	Compositions métalliques solubles dans les huiles et leur procédé de préparation
US3464970A (en) *	1967-03-13	1969-09-02	Maruzen Oil Co Ltd	Process for preparing over-based sulfurized calcium phenates
US3493516A (en) *	1966-05-04	1970-02-03	Chevron Res	Carboxylate modified phenates
FR2026567A1 (de) *	1968-12-19	1970-09-18	Mobil Oil Corp
GB1280749A (en) *	1970-06-18	1972-07-05	Maruzen Oil Company Ltd	Process for preparation of over-based sulphurized phenates
FR2271280A1 (de) *	1974-05-17	1975-12-12	Exxon Research Engineering Co
FR2277145A1 (fr) *	1974-07-05	1976-01-30	Exxon Research Engineering Co	Detergent a base de magnesium surbasique et son application aux huiles lubrifiantes
US4016093A (en) *	1976-03-19	1977-04-05	Mobil Oil Corporation	Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3282835A (en) *	1963-02-12	1966-11-01	Lubrizol Corp	Carbonated bright stock sulfonates and lubricants containing them
GB1144084A (en) *	1966-08-24	1969-03-05	Orobis Ltd	Improvements in or relating to lubricant additives
US3936480A (en) *	1971-07-08	1976-02-03	Rhone-Progil	Additives for improving the dispersing properties of lubricating oil
BE786032A (fr) *	1971-07-08	1973-01-08	Rhone Progil	Nouveaux additifs pour huiles lubrifiantes
FR2300793A1 (fr) *	1975-02-17	1976-09-10	Orogil	Nouvelles compositions lubrifiantes
IT1044574B (it) *	1975-07-14	1980-03-31	Liquichimica Robassomero Spa	Additivo detergentfe per la sua preparazione
FR2355739A1 (fr) *	1976-06-25	1978-01-20	Thibault Jacques	Ensemble de traitement sur supports de colis de qualites differentes
FR2416942A1 (fr) *	1978-02-08	1979-09-07	Orogil	Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes
US4229308A (en) *	1978-02-08	1980-10-21	Rhone-Poulenc Industries	Polymer lubricating oil additives bearing nitrogen groups and their use as additives for lubricating oils
US4222882A (en) *	1978-02-08	1980-09-16	Rhone-Poulenc Industries	Polymers bearing groups derived from N-substituted lactams and their use as lubricating oil additives
FR2429831A2 (fr) *	1978-06-26	1980-01-25	Orogil	Nouveau procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes
FR2450868A1 (fr) *	1979-03-09	1980-10-03	Orogil	Procede de preparation d'alkylphenates de magnesium et application des produits obtenus comme additifs detergents-dispersants pour huiles lubrifiantes

1982
- 1982-06-24 FR FR8211060A patent/FR2529226B1/fr not_active Expired
1983
- 1983-03-21 MX MX26983A patent/MX26983A/es unknown
- 1983-06-20 DE DE8383401269T patent/DE3366063D1/de not_active Expired
- 1983-06-20 AT AT83401269T patent/ATE22112T1/de not_active IP Right Cessation
- 1983-06-20 EP EP83401269A patent/EP0102255B1/de not_active Expired
- 1983-06-22 GR GR71755A patent/GR78596B/el unknown
- 1983-06-22 ZA ZA834555A patent/ZA834555B/xx unknown
- 1983-06-22 AU AU16125/83A patent/AU557851B2/en not_active Ceased
- 1983-06-23 DK DK290083A patent/DK162398C/da not_active IP Right Cessation
- 1983-06-23 CA CA000431110A patent/CA1182628A/fr not_active Expired
- 1983-06-23 ES ES523542A patent/ES523542A0/es active Granted
- 1983-06-23 GB GB08317023A patent/GB2123022B/en not_active Expired
- 1983-06-23 BR BR8303347A patent/BR8303347A/pt not_active IP Right Cessation
- 1983-06-23 PT PT76930A patent/PT76930B/pt not_active IP Right Cessation
- 1983-06-24 JP JP58113000A patent/JPS5946262A/ja active Granted
- 1983-06-24 US US06/507,804 patent/US4514313A/en not_active Expired - Lifetime
- 1983-06-24 PH PH29116A patent/PH19427A/en unknown

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1382559A (fr) *	1963-02-12	1964-12-18	Lubrizol Corp	Compositions métalliques solubles dans les huiles et leur procédé de préparation
US3493516A (en) *	1966-05-04	1970-02-03	Chevron Res	Carboxylate modified phenates
US3464970A (en) *	1967-03-13	1969-09-02	Maruzen Oil Co Ltd	Process for preparing over-based sulfurized calcium phenates
FR2026567A1 (de) *	1968-12-19	1970-09-18	Mobil Oil Corp
GB1280749A (en) *	1970-06-18	1972-07-05	Maruzen Oil Company Ltd	Process for preparation of over-based sulphurized phenates
FR2271280A1 (de) *	1974-05-17	1975-12-12	Exxon Research Engineering Co
FR2277145A1 (fr) *	1974-07-05	1976-01-30	Exxon Research Engineering Co	Detergent a base de magnesium surbasique et son application aux huiles lubrifiantes
US4016093A (en) *	1976-03-19	1977-04-05	Mobil Oil Corporation	Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0095322A3 (en) *	1982-05-22	1984-09-05	Orobis Limited	Process for the production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
FR2587353A1 (fr) *	1985-09-17	1987-03-20	Orogil	Nouveaux additifs detergents-dispersants suralcalinises stables a l'hydrolyse pour huiles lubrifiantes et leur procede de preparation
EP0219382A1 (de) *	1985-09-17	1987-04-22	Orogil	Gegen Hydrolisierung stabilisierte überalkalisierte Detergens-Dispergierzusätze für Schmieröle und Verfahren zu deren Herstellung
EP0577338A3 (en) *	1992-06-27	1994-06-01	Bp Chemicals Additives	Alkaline earth metal sulphurised hydrocarbyl phenate-containing additive concentrate, process for its production and use thereof

Also Published As

Publication number	Publication date
BR8303347A (pt)	1984-02-07
FR2529226B1 (fr)	1987-01-16
DK290083A (da)	1983-12-25
EP0102255B1 (de)	1986-09-10
AU1612583A (en)	1984-01-05
JPS5946262A (ja)	1984-03-15
DK162398C (da)	1992-03-23
GB2123022B (en)	1985-11-13
CA1182628A (fr)	1985-02-19
ATE22112T1 (de)	1986-09-15
PH19427A (en)	1986-04-15
PT76930A (fr)	1983-07-01
GB2123022A (en)	1984-01-25
ZA834555B (en)	1984-03-28
AU557851B2 (en)	1987-01-08
GR78596B (de)	1985-09-27
FR2529226A1 (fr)	1983-12-30
ES8403964A1 (es)	1984-04-01
US4514313A (en)	1985-04-30
ES523542A0 (es)	1984-04-01
PT76930B (fr)	1986-03-11
DE3366063D1 (en)	1986-10-16
MX26983A (es)	1994-03-31
DK290083D0 (da)	1983-06-23
JPS6242957B2 (de)	1987-09-10
DK162398B (da)	1991-10-21
GB8317023D0 (en)	1983-07-27

Legal Events

Date	Code	Title	Description
1984-01-06	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1984-03-07	AK	Designated contracting states	Designated state(s): AT BE CH DE FR IT LI NL SE
1984-05-30	17P	Request for examination filed	Effective date: 19840322
1986-06-18	ITF	It: translation for a ep patent filed
1986-07-26	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
1986-09-10	AK	Designated contracting states	Kind code of ref document: B1 Designated state(s): AT BE CH DE FR IT LI NL SE
1986-09-10	REF	Corresponds to:	Ref document number: 22112 Country of ref document: AT Date of ref document: 19860915 Kind code of ref document: T
1986-10-16	REF	Corresponds to:	Ref document number: 3366063 Country of ref document: DE Date of ref document: 19861016
1987-07-08	PLBE	No opposition filed within time limit	Free format text: ORIGINAL CODE: 0009261
1987-07-08	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT
1987-08-26	26N	No opposition filed
1992-05-15	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: AT Payment date: 19920515 Year of fee payment: 10
1992-05-20	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: SE Payment date: 19920520 Year of fee payment: 10 Ref country code: BE Payment date: 19920520 Year of fee payment: 10
1992-05-21	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: CH Payment date: 19920521 Year of fee payment: 10
1992-06-30	ITTA	It: last paid annual fee
1992-06-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: NL Payment date: 19920630 Year of fee payment: 10
1993-06-20	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: AT Effective date: 19930620
1993-06-21	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: SE Effective date: 19930621
1993-06-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: LI Effective date: 19930630 Ref country code: CH Effective date: 19930630 Ref country code: BE Effective date: 19930630
1993-12-31	BERE	Be: lapsed	Owner name: OROGIL Effective date: 19930630
1994-01-01	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: NL Effective date: 19940101
1994-02-16	NLV4	Nl: lapsed or anulled due to non-payment of the annual fee
1994-02-28	REG	Reference to a national code	Ref country code: CH Ref legal event code: PL
1995-01-31	EUG	Se: european patent has lapsed	Ref document number: 83401269.2 Effective date: 19940110
2002-06-05	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: FR Payment date: 20020605 Year of fee payment: 20
2002-06-28	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: DE Payment date: 20020628 Year of fee payment: 20

Publication	Publication Date	Title
EP0102255B1 (de)	1986-09-10	Verfahren zur Herstellung von sulfurierten Erdalkalimetallalkylphenaten verwendbar als Schmierölzusatz
EP0133088B1 (de)	1987-05-20	Verfahren zur Herstellung von auf Calcium basierten Detergenz-Dispergierzusätzen mit sehr hoher Alkalität und die erhaltenen Produkte
EP0164286B1 (de)	1989-08-02	Verfahren zur Herstellung von auf nichtschäumenden Erdalkalimetallalkylarylsulfonaten basierenden Zusatzstoffen für Schmieröle mit detergens- und dispersierender Wirkung
FR2605329A1 (fr)	1988-04-22	Procede de preparation de derives de metal du groupe 2 d'alkylphenols sulfures rendus surbasiques.
EP0007257B1 (de)	1982-07-14	Verfahren zur Herstellung von Reinigungsmittellösungen hoher Alkalität für Schmieröle und daraus hergestelltes Produkt
EP0003694B1 (de)	1982-02-24	Verfahren zur Bereitung von hochbasischen Mitteln mit detergierender, dispergierender Wirkung für Schmieröle, und so erhaltenes Produkt
FR2935708A1 (fr)	2010-03-12	Composition d'huile lubrifiante et procede pour reduire la precipitation des asphaltenes
EP0102254B1 (de)	1986-12-30	Überalkalisierter Detergens-Dispergierzusatz für Schmieröle
FR2915998A1 (fr)	2008-11-14	Composition d'huile lubrifiante destinee a ameliorer la limitation d'oxydation, d'augmentation de viscosite, de consommation d'huile et de depots sur les pistons.
EP0812313B1 (de)	1999-12-22	Sulfonate mit niedriger basizität
EP0007260B1 (de)	1981-09-23	Verfahren zur Herstellung von Metall enthaltenden reinigenden dispergierenden Zusatzstoffen hoher Alkalität, besonders für Schmieröl, und daraus hergestelltes Produkt
EP0016676B1 (de)	1982-10-13	Verfahren zur Herstellung von Magnesium-Alkylphenaten
EP0101334B1 (de)	1987-11-11	Metallenthaltender Detergens-Dispergierzusatz von hoher Alkalität für Schmieröle
EP0812314B1 (de)	1999-12-22	Magnesium niedrigbasische sulphonate
EP0211722B1 (de)	1990-05-23	Sulfonierte und sulfurisierte Detergens Dispergierzusätze für Schmieröle
FR2625219A1 (fr)	1989-06-30	Additifs detergents-dispersants a base de sels de metaux alcalino-terreux et alcalins pour huiles lubrifiantes
FR2909684A1 (fr)	2008-06-13	Additifs et formulations de lubrifiants utilises pour obtenir des proprietes antiusure ameliorees
EP0006796B1 (de)	1981-11-04	Verfahren zur Herstellung von Metall enthaltenden überalkalisierten Reinigungsmittellösungen für Schmieröl und daraus hergestelltes Produkt
EP0219382B1 (de)	1989-03-22	Gegen Hydrolisierung stabilisierte überalkalisierte Detergens-Dispergierzusätze für Schmieröle und Verfahren zu deren Herstellung
WO2021123658A1 (fr)	2021-06-24	Procede de fabrication d'estolides et composition d'estolides