Source: http://www.google.com/patents/US5840920?dq=5191154
Timestamp: 2017-07-23 11:26:21
Document Index: 761152671

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Patent US5840920 - Process for preparing compositions useful as intermediates for preparing ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA process for reacting olefinic compounds, certain carboxylic reactants, and aldehydes or ketones and products prepared by the process. The compositions of the process are useful as intermediates for the preparation of additives for lubricants and fuels....http://www.google.com/patents/US5840920?utm_source=gb-gplus-sharePatent US5840920 - Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS5840920 APublication typeGrantApplication numberUS 08/694,046Publication dateNov 24, 1998Filing dateAug 8, 1996Priority dateAug 8, 1996Fee statusLapsedAlso published asUS6207839Publication number08694046, 694046, US 5840920 A, US 5840920A, US-A-5840920, US5840920 A, US5840920AInventorsMark R. BakerOriginal AssigneeThe Lubrizol CorporationExport CitationBiBTeX, EndNote, RefManPatent Citations (24), Non-Patent Citations (4), Referenced by (28), Classifications (147), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives
In one preferred embodiment, at least one R is derived from polybutene, that is, polymers of C4 olefins, including 1-butene, 2-butene and isobutylene. Those derived from isobutylene, i.e., polyisobutylenes, are especially preferred. In another preferred embodiment, R is derived from polypropylene. In another preferred embodiment, R is derived from ethylene-alpha olefin polymers, including ethylene-propylene-diene polymers. Representative of such polymers are the ethylene-propylene copolymers and ethylene-propylene-diene terpolymers marketed under the TRILENE® tradename by the Uniroyal Company. Molecular weights of such polymers may vary over a wide range, but especially preferred are those having number average molecular weights (Mn) ranging from about 300 to about 20,000, preferably 700 to about 10,000, often from 900 to 2,500. In one preferred embodiment, the olefin is an ethylene-propylene-diene terpolymer having Mn ranging from about 900 to about 8,000, often up to about 2,000. Such materials are included among the TRILENE® polymers marketed by the Uniroyal Company, Middlebury, Conn. USA and ORTHOLEUM® 2052 marketed by the DuPont Company.
In one embodiment the polybutene is substantially monoolefinic, comprising at least about 30 mole %, preferably at least about 50 mole % vinylidene groups, more often at least about 70 mole % vinylidene groups. Such materials and methods for preparing them are described in U.S. Pat. Nos. 5,071,919; 5,137,978; 5,137,980; 5,286,823 and 5,408,018, and in published European patent application EP 646103-A1, each of which is expressly incorporated herein by reference. They are commercially available, for example under the tradenames ULTRAVIS® (BP Chemicals) and Glissopal (BASF).
The process of this invention is conducted at temperatures ranging from ambient up to the lowest decomposition temperature of any of the reactants, usually from about 60° C. to about 220° C., more often from about 120° C. to about 180° C., preferably up to about 160° C. When the reaction is conducted in the presence of organic sulfonic acid or mineral acid catalyst, the reaction is usually conducted at temperatures up to about 160° C. The process employs from about 0.6 moles of reactant (B) per mole of olefinic compound (A), up to 1.5 moles (B) per equivalent of (A), more often from about 0.8 moles (B) per mole of (A) to about 1.2 moles (B) per equivalent of (A), even more often from about 0.95 moles (B) per mole of (A) to about 1.05 moles (B) per equivalent of (A). Reactant (C) is used in amounts ranging from about 0.5 to about 2 moles per mole of (B), preferably, from about 0.8 to about 1.5 moles per mole of (B), and most often from about 0.9 to about 1.1 moles per mole of (B). As noted herein, many reactants contain water which is removed. Removal of water at moderate temperatures is attainable employing reduced pressure, a solvent that aids in azeotropic distillation of water, or by purging with an inert gas such as N2.
A reactor is charged with 250 parts of polyisobutylene (GLISSOPAL® ES3250, BASF) having Mn about 1000 and containing about 87 mole percent terminal vinylidene groups, 52 parts 50% aqueous glyoxylic acid, 15 parts paraformaldehyde and 1 part 70% aqueous methanesulfonic acid. These are heated with mixing, under N2, to 160° C. and are held at temperature for a total of 4.5 hours. The materials are stripped to 135° C. and 25 millimeters Hg pressure (mm Hg) and filtered. The filtrate has saponification no ═32.4, and contains (GPC) 96.3% material having Mn ═1432 and Mw ═2157.
A reactor is charged with 250 parts of the polyisobutylene of Example 1, 37 parts of 50% aqueous glyoxylic acid, 7.5 parts paraformaldehyde and 1 part 70% aqueous methanesulfonic acid. The materials are heated with mixing under N2, to 160° C. and are held at temperature for 5 hours, collecting 26 parts water. The materials are stripped to 125° C. and 25 mm Hg and filtered. The filtrate has saponification no ═40.3, contains 13.9% unreacted polyisobutylene and has (GPC) Mn ═1539 and Mw ═2693.
Employing the same reactants as in Example 2, 1200 parts of polyisobutylene, 177.6 parts 50% aqueous glyoxylic acid, 4.8 parts 70% aqueous methanesulfonic acid and 36 parts paraformaldehyde are reacted, under N2, at 160° C. for 5.5 hours, collecting 114 parts water. The materials are cooled to 100° C. and stripped to 140° C. and 20 mm Hg and filtered. The filtrate has saponification no ═44 and has (VPO) Mn ═1852.
Employing the same reactants as in Example 2, 3000 parts of polyisobutylene, 444 parts, 444 parts 50% aqueous glyoxylic acid, 12 parts 70% aqueous methanesulfonic acid and 99 parts paraformaldehyde are reacted, under N2 at 160° C. for 5 hours, collecting 344 parts water then for an additional 3 hours. The materials are cooled then stripped to 160° C. and 30 mm Hg and filtered. The filtrate has saponification no ═44, has (GPC) Mn ═1450 and contains 17% unreacted polyisobutylene.
Employing the same reactants as in Example 2, 3000 parts of polyisobutylene, 488 parts 50% aqueous glyoxylic acid, 12 parts 70% aqueous methanesulfonic acid and 99 parts paraformaldehyde are reacted, under N2, at 120° C. for hours, collecting water then at 160° C. for 5 hours, collecting water. The materials are cooled to 140° C. and filtered. The filtrate has saponification no ═50, has (GPC) Mn ═1475, Mw ═2422 and contains 15 % unreacted polyisobutylene.
A reactor is charged with 832 parts of polyisobutylene (GLISSOPAL ES3252) having Mn about 2400 and containing about 70 mole percent terminal vinylidene groups, 61.6 parts 50% aqueous glyoxylic acid, 13.7 parts paraformaldehyde, 3 parts 70% aqueous methanesulfonic acid, and 571.2 parts mineral oil. The materials are heated to 120° C. over 1 hour, collecting water, then to 160° C. over 1 hour, reacted at 160° C. for 8 hours, while collecting water. The materials are stripped to 160° C. and 25 mm Hg and filtered at 140° C. The filtrate has saponification no ═13.4. (GPC) Mn ═4324, Mw ═9779 (65 %) and Mn ═340, Mw ═412. (35%).
A reactor is charged with 4000 parts polyisobutylene (ULTRAVIS® 10, BP Chemicals) having Mn about 1000 and containing about 80 mole % terminal vinylidene groups, 592 parts 50% aqueous glyoxylic acid, 132 parts paraformaldehyde and 16 parts 70% aqueous methanesulfonic acid. The materials are heated to 120° C. over 0.75 hour then to 160° C. over 2.5 hours, collecting water, then reacted at 160° C for a total of 6 hours; total water collected, 475 parts. The materials are stripped to 160° C. and 40 mm Hg and filtered. The filtrate contains 19.9% unreacted polyisobutylene, has saponification no. ═42 and (GPC) Mn ═1419, Mw ═3272.
A reactor is charged with 1000 parts of the polyisobutylene used in Example 1, 148 parts of 50% aqueous glyoxylic acid, 29 parts glyoxal and 2 parts 70% aqueous methane sulfonic acid. Under N2, the materials are heated to 130° C., held at 130° C. for 2 hours, heated to 160° C., and held at 160° C. for 4 hours, while collecting a total of 108 parts aqueous distillate. The materials are mixed with 730.7 parts mineral oil and filtered at 140° C. obtaining a filtrate having total acid no ═11.8 and saponification no ═26.5.
A reactor is charged with 800 parts of the polyisobutylene used in Example 1, 118.4 parts of 50% aqueous glyoxylic acid, 18.6 parts glyoxal and 1.6 parts 70% aqueous methane sulfonic acid. Under N2, the materials are heated to 140° C., held at 140°-148° C. for 6 hours, then at 145° C. for 7 hours, while collecting aqueous distillate. The materials are mixed with 567 parts mineral oil and filtered at 145° C. obtaining a filtrate having total acid no ═0, saponification no ═23.2 and (GPC) 59.94% Mn ═1743, Mw ═2184; 40.1% Mn ═358.
A reactor is charged with 1000 parts of the polyisobutylene used in Example 1, 37 parts 50% aqueous glyoxylic acid, 35.6 parts nonyl aldehyde and 1 part 70% aqueous methane sulfonic acid. The materials are heated, under N2, to 160° C. and are held at 160° C. for 5 hours while collecting 23.9 parts aqueous distillate. The materials are stripped to 125° C. at 56 mm Hg, then filtered at 20° C. The filtrate has total acid no. ═14.8, saponification no. ═36.4 and, by GPC, 100% Mn 1191, Mw 1881, and contains 25% unreated polyisobutylene (TLC-FID).
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Terada et al., Tetrahedron Letters, 35, 6693 (1994).* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6147036 *Aug 8, 1997Nov 14, 2000The Lubrizol CorporationProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives and derivatives thereofUS6211122 *Jul 27, 1998Apr 3, 2001The Lubrizol CorporationCarboxylic compositions and derivatives thereof and use as lubricating oil and fuel additivesUS6827750Aug 24, 2001Dec 7, 2004Dober Chemical CorpControlled release additives in fuel systemsUS6835218Aug 24, 2001Dec 28, 2004Dober Chemical Corp.Fuel additive compositionsUS7883638May 27, 2008Feb 8, 2011Dober Chemical CorporationControlled release cooling additive compositionsUS7938277May 27, 2008May 10, 2011Dober Chemical CorporationControlled release of microbiocidesUS8109287Jul 22, 2009Feb 7, 2012Cummins Filtration Ip, Inc.Controlled release of additives in fluid systemsUS8425772Jul 29, 2011Apr 23, 2013Cummins Filtration Ip, Inc.Filtration device with releasable additiveUS8591747May 26, 2009Nov 26, 2013Dober Chemical Corp.Devices and methods for controlled release of additive compositionsUS8702995May 27, 2008Apr 22, 2014Dober Chemical Corp.Controlled release of microbiocidesUS20090294379 *May 27, 2008Dec 3, 2009Dober Chemical CorporationControlled release of additive compositionsEP2998384A1Jun 13, 2006Mar 23, 2016The Lubrizol CorporationDiesel fuel composition comprising a quaternary ammonium salt detergentWO2009045979A1Sep 30, 2008Apr 9, 2009The Lubrizol CorporationLubricants that decrease micropitting for industrial gearsWO2011059626A1Oct 14, 2010May 19, 2011The Lubrizol CorporationLubricant system clean-up compositions and methods thereofWO2011159742A1Jun 15, 2011Dec 22, 2011The Lubrizol CorporationMethods of removing deposits in oil and gas applicationsWO2012084906A1Dec 20, 2011Jun 28, 2012Rhodia OperationsFuel additive composition containing a dispersion of iron particles and a 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CorporationImidazole containing quaternary ammonium saltsWO2015184301A2May 29, 2015Dec 3, 2015The Lubrizol CorporationCoupled quaternary ammonium saltsWO2017083042A1Oct 11, 2016May 18, 2017The Lubrizol CorporationUsing quaternary amine additives to improve water separationWO2017096159A1Dec 2, 2016Jun 8, 2017The Lubrizol CorporationUltra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails* Cited by examinerClassifications U.S. Classification549/266, 549/320, 549/273, 549/295International ClassificationC10L1/14, C10L1/224, C10M129/92, C10L10/02, C10L1/232, C08F8/00, C10L1/16, C10L1/198, C10M167/00, C10L1/238, C07D309/30, C10L1/20, C10L1/18, C10L10/00, C10L1/22, C10L1/24, C10M133/52, C10M159/12, C10L1/30, C07D307/33, C10L1/26Cooperative ClassificationC08F8/10, C10M2223/045, C10M2217/04, C10L1/1905, C10L1/233, C10M2217/028, C10M2219/02, C10L1/1883, C10L1/306, C10M2207/028, C10M2229/05, C10M167/00, C10L1/1691, C10L1/1881, C10M2223/02, C10M2207/22, C10M2223/04, C10M2219/087, C10M2217/02, C10L1/1802, C10M2215/065, C10M2215/067, C10L10/02, C10L1/1832, C10L1/191, C10M2217/00, C10M129/92, C10M2207/027, C10L1/2691, C10M2203/10, C10M2215/02, C10L1/1817, C10L1/1616, C10L1/1824, C10M133/52, C10M2207/404, C10M2205/026, C07D307/33, C10L1/1641, C10M2203/102, C10M2215/068, C10M2217/06, C10M159/12, C10L1/1985, C10N2240/08, C10M2227/061, C10M2203/024, C10M2207/40, C10M2207/26, C10M2203/022, C10L1/2456, C10L1/198, C10M2219/084, C10M2219/088, C10M2207/08, C10L1/238, C10M2207/128, C10M2223/042, C10L1/221, C10L1/303, C10M2229/02, C07D309/30, C10L1/224, C10M2217/046, C10M2203/108, C10M2223/047, C10M2207/262, C10M2229/042, C10M2215/24, C10M2215/06, C10M2215/066, C10M2223/049, C10M2215/26, C10L10/00, C10L1/143, C10N2210/02, C10M2219/046, C10M2209/086, C10M2203/02, C10M2215/064, C10M2203/04, C10L1/2383, C10M2229/04, C10L1/2225, C10M2207/129, C10M2203/104, C10M2215/04, C10L1/2493, C10M2215/28, C10M2205/06, C10M2219/066, C10M2207/402, C10M2207/123, C10L1/2406, C10M2207/023, C10M2219/089, C10M2215/086, C10L1/201, C10M2203/106, C10N2270/02, C10M2229/041, C10M2207/026, C10L1/232, C10M2223/10, C10M2207/124European ClassificationC08F8/00, C10L1/198, C10L1/224, C10L1/238, C10L1/232, C10L1/14B, C10L10/02, C10M167/00, C10M159/12, C10L10/00, C07D309/30, C10L1/22W, C10L1/18W, C10M133/52, C10L1/30A1, C10M129/92, C07D307/33Legal EventsDateCodeEventDescriptionAug 8, 1996ASAssignmentOwner name: LUBRIZOL CORPORATION, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAKER, MARK R.;REEL/FRAME:008156/0185Effective date: 19960808Jun 11, 2002REMIMaintenance fee reminder mailedNov 25, 2002LAPSLapse for failure to pay maintenance feesJan 21, 2003FPExpired due to failure to pay maintenance feeEffective date: 20021124RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services