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US2844534A Expired / Lapsed US ⏱️ 0.0 years remaining

High molecular weight branched-chain ethers of lubricating grade

Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1952-10-20
•
Granted: 1958-07-22
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Expires: 1972-10-20
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Abstract

Abstract Synthetic rubbers, e.g. isobutylene-diolefin and butadiene-styrene copolymers are plasticized with ethers obtained from the mixed alcohols produced by the " oxo " process (see Group IV (b)), said ethers having the formula R-O-R1 wherein R and R1 represent hydrocarbon radicals having at least 8, preferably 10 to 20, carbon atoms, and wherein either or both R and R1 represent branched-chain hydrocarbon radicals.ALSO:The invention comprises ethers of the general formula R-O-R1, wherein R and R1 represent hydrocarbon radicals having at least 8 carbon atoms, preferably 10 to 20 carbon atoms, and wherein either or both of the symbols R and R1 represent branched-chain hydrocarbon radicals, characterized in that said ethers are obtained from the mixed alcohols produced by the oxo process. The preferred ethers are those having pour points below 20 DEG F. and flash points above 300 DEG F. Suitable oxo alcohols are obtained by subjecting dimers, trimers, tetramers or higher polymers or copolymers of propylene, butylene or isobutylene to the oxo process and hydrogenating the products. The oxo ethers may be prepared by heating the oxo alcohols with sulphuric acid or p-toluene-sulphonic acid. The ethers may be used as lubricants, in lubricating compositions (see Group III), and as plasticizers for synthetic rubbers (see Group IV (a)). Examples describe the preparation of ethers by heating C13 or C16 oxo alcohols with sulphuric acid or p-toluenesulphonic acid.ALSO:Lubricating compositions comprise ethers having the general formula ROR1, wherein R and R1 represent hydrocarbon radicals having at least 8, preferably 10 to 20, carbon atoms and wherein either or both R and R1 represent branched-chain radicals, characterized in that said ethers are obtained from the mixed alcohols produced by the oxo process (see Group IV(b)), together with other lubricants, such as mineral oils, esters, formals, mercaptals, polyethers and oxidized mineral oils, or together with from 2-30 per cent by weight of an extreme pressure agent containing sulphur and/or phosphorus and/or halogen, e.g. tri-cresyl phosphate. The ethers may also be blended with viscosity index improvers, anti-foamants, pour depressants, and anti-oxidants. Lubricating greases are obtained by incorporating into the ethers a grease thickener, preferably an alkali or alkaline earth metal soap of a C10-C30 fatty acid or a complex metal soap of a C10-C30 fatty acid and a C1-C5 carboxylic acid such as acetic, furoic, acrylic, or crotonic acid. In examples, lubricating greases are obtained from a C13 oxo ether together with a complex lithium soap of co-neutralized Hydrofol Acids 54 and acetic or crotonic acid, and (1) phenyl-a -naphthylamine, (2) phenothiazine or (3) C8 oxo phosphate and phenyl-a -naphthyamine.

Inventors

  • 👤 Delmer L Cottle
  • 👤 Arnold J Morway
  • 👤 David W Young

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 15:13
CPC Classifications
C; C10; C10M; C10M169/00; C07; C07C; C07C29/00; C07C29/16; C07C41/00; C07C41/01; C07C41/09; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C08; C08K; C08K5/00; C08K5/04; C08K5/06; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/185; C10L1/1852; C10M105/00; C10M105/08; C10M105/18; C10M105/74; C10M117/00; C10M117/02; C10M133/00; C10M133/02; C10M133/04; C10M133/12; C10M2207/00; C10M2207/04; C10M2207/0406; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/122; C10M2207/1225; C10M2207/125; C10M2207/126; C10M2207/1265; C10M2207/129; C10M2207/16; C10M2207/166; C10M2207/18; C10M2207/186; C10M2207/20; C10M2207/206; C10M2207/24; C10M2207/246; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/066; C10M2215/067; C10M2215/068; C10M2219/00; C10M2219/10; C10M2219/104; C10M2219/108; C10M2223/00; C10M2223/003; C10M2223/02; C10M2223/023; C10M2223/04; C10M2223/0405; C10M2223/041; C10M2223/042; C10M2223/049; C10M2223/0495; C10M2223/06; C10M2223/0603; C10M2223/08; C10M2223/083; C10M2223/10; C10M2223/103; C10N; C10N2010/00; C10N2010/02; C10N2040/00; C10N2040/08; C10N2040/30; C10N2040/32; C10N2040/34; C10N2040/36; C10N2040/38; C10N2040/40; C10N2040/42; C10N2040/44; C10N2040/50

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 104 words
AN ETHER OF THE GENERAL FORMULA R-O-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED CHAIN ALCOIHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400*F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL.
Claim 2
Dependent Claim 104 words
AN ETHER OF THE GENERAL FORMULA R-O-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED CHAIN ALCOIHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400*F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL.
Claim 3
Dependent Claim 125 words
A LUBRICATING GREASE COMPRISING AS A LUBRICATING OIL CONSTITUENT A LUBRICATING PROPORTION OF AN EHTER OF THE GENERAL FORMULA R-O-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED-CHAIN ALCOHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400*F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL, AND A GREASE THICKENING PROPORTION OF A GREASE THICKENER.
Claim 4
Dependent Claim 125 words
A LUBRICATING GREASE COMPRISING AS A LUBRICATING OIL CONSTITUENT A LUBRICATING PROPORTION OF AN EHTER OF THE GENERAL FORMULA R-O-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED-CHAIN ALCOHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400*F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL, AND A GREASE THICKENING PROPORTION OF A GREASE THICKENER.
Claim 5
Dependent Claim 122 words
A COMPOSITION OF MATTER COMPRISING A MAJOR PROPORTION OF A SYNTHETIC RUBBER AND A MINOR PLASTICIZING PROPORTION OF AN ETHER HAVING THE GENERAL FORMULA R-0-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED-CHAIN ALCOHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400* F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL.
Claim 6
Dependent Claim 122 words
A COMPOSITION OF MATTER COMPRISING A MAJOR PROPORTION OF A SYNTHETIC RUBBER AND A MINOR PLASTICIZING PROPORTION OF AN ETHER HAVING THE GENERAL FORMULA R-0-R'', WHEREIN R AND R'' ARE THE HYDROCARBON RADICALS OF OXO ALCOHOLS HAVING ABOUT 10 TO 20 CARBON ATOMS PER MOLECULE, SAID OXO ALCOHOL BEING AN ISOMERIC MIXTURE OF BRANCHED-CHAIN ALCOHOLS PRODUCED BY THE CATALYTIC CARBONYLATION OF OLEFINS SELECTED FROM THE GROUP CONSISTING OF POLYMERS AND COPOLYMERS OF C3 AND C4 OLEFINS WITH CO AND H2 AT TEMPERATURES OF ABOUT 300 TO 400* F., UNDER PRESSURES OF ABOUT 2,500 TO 4,000 P. S. I. G., IN THE PRESENCE OF A COBALT CATALYST TO FORM AN ALDEHYDE, FOLLOWED BY CATALYTIC HYDROGENATION OF SAID ALDEHYDE TO FORM SAID OXO ALCOHOL.

References Cited (Backward Citations)

US2366042A Cited
US2455892A Cited
US2595096A Cited
US2623074A Cited
US2671119A Cited
US2594341A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1961-07-21 1962-01-20 1962-07-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1965-07-21 1966-01-20 1966-07-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1969-07-21 1970-01-20 1970-07-22 $7700.00 Window Closed / Lapsed

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