US2091398A - Synthesis of lubricating oils - Google Patents

Synthesis of lubricating oils Download PDF

Info

Publication number
US2091398A
US2091398A US524412A US52441231A US2091398A US 2091398 A US2091398 A US 2091398A US 524412 A US524412 A US 524412A US 52441231 A US52441231 A US 52441231A US 2091398 A US2091398 A US 2091398A
Authority
US
United States
Prior art keywords
oil
viscosity
oils
olefin
lubricating oils
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
Application number
US524412A
Inventor
Jr Frederick W Sullivan
Voorhees Vanderveer
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.)
Standard Oil Co
Original Assignee
Standard Oil Co
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 Standard Oil Co filed Critical Standard Oil Co
Priority to US524412A priority Critical patent/US2091398A/en
Application granted granted Critical
Publication of US2091398A publication Critical patent/US2091398A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G50/00Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • C10G50/02Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes

Definitions

  • the present invention relates to the production of lubricating oils by synthesis by means of catalysts from olefin hydrocarbons.
  • the olefin hydrocarbons subjected to treatment in accordance with this invention have ranged from octene to cetene.
  • the hydrocarbon selected is subjected to treatment with a suitable quantity of the catalyst, say 1 to 5% and in general about 2%, for six to ten hours at temperatures of from to 100 C. and the resulting product allowed to settle to separate the aluminum chloride sludge from the polymerized oil.
  • the sludge is separated and the oil, preferably after Washing with alkali such as sodium hydroxide 50 solution, and water, is reduced by fire. and steam distillation to a bottom of the desired viscosity.
  • alkali such as sodium hydroxide 50 solution
  • oils secured from individual olefins of higher carbon content are similar with respect to their temperature-viscosity characteristics, or better than that derived from octene. With increasing carbon content of the olefin treated, oils of higher cold test are secured.
  • an oil is secured having a viscosity of 717 seconds Saybolt at 100 F. and a cold test of 35 F. or l.'7 C.
  • the treatment of dodecylene in a similar manner likewise produces an oil of low sensitiveness to temperature changes.
  • polymerizing agents having a similar action to aluminum chloride may likewise be employed, such as boron fluoride, zinc chloride, ferric chloride, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Description

l atented Aug. 31, 1937 umrso STATES 2,091,398 SYNTHESIS or LUBRICATING OILS Frederick W. Sullivan, Jr., and Vanderveer Voorhees, Hammond, Ind assignors to Standard; Oil Con'lpany, Chicago, 111., a corporation of Indiana No Drawing. Application March 21, 1931', Serial No. 524,412
7 Claims.
The present invention relates to the production of lubricating oils by synthesis by means of catalysts from olefin hydrocarbons.
It has hitherto been proposed to subject various unsaturated hydrocarbons such as amylene, butylene and ethylene to the action of various catalysts of the type of aluminum chloride, thereby forming heavier oils of a viscosity suitable for use as lubricating oils. The heavy oils thus pro- 10 duced, however, have been found to undergo marked changes in viscosity with changes in temperature, being inferior in this respect to natural oils, such as the lubricating oils derived from Pennsylvania oils, and in many cases inferior to the natural lubricating oils derived from Mid- Continent and naphthenic oils.
It has also hitherto been proposed (U. S. Patent 1,955,260) to subject hydrocarbon waxes to pyrolytic decomposition whereby olefin hydrocarbons are produced largely within the gasoline boiling range, and thereafter to subject the resulting mixture of unsaturated hydrocarbons to the polymerizing action of aluminum chloride. In that process no attempt was made to isolate and polymerize hydrocarbons having a selected boiling range.
We have now discovered that by subjecting olefin compounds, and particularly straightchain olefin compounds individually to the action of aluminum chloride and similar catalysts, said hydrocarbons having 8 or more carbon atoms, the heavy oils secured as a result of the polymerization are markedly superior to natural oils in their temperature-viscosity characteristics, the
changes of viscosity with increasing temperature being less than those taking place in typical oils, for example, of Pennsylvania origin and of like viscosity.
The olefin hydrocarbons subjected to treatment in accordance with this invention have ranged from octene to cetene. The hydrocarbon selected is subjected to treatment with a suitable quantity of the catalyst, say 1 to 5% and in general about 2%, for six to ten hours at temperatures of from to 100 C. and the resulting product allowed to settle to separate the aluminum chloride sludge from the polymerized oil. The sludge is separated and the oil, preferably after Washing with alkali such as sodium hydroxide 50 solution, and water, is reduced by fire. and steam distillation to a bottom of the desired viscosity. Under the conditions set forth, the polymerized oil derived from normal octene and reduced to a viscosity of 88 seconds Saybolt at 210 F. was
found to have a viscosity of 905 seconds Saybolt at F. This oil had a cold test of 25 F. or -31.6 C.
The oils secured from individual olefins of higher carbon content are similar with respect to their temperature-viscosity characteristics, or better than that derived from octene. With increasing carbon content of the olefin treated, oils of higher cold test are secured. Thus, by treatment with cetene, and reduction of the polymerized oil to a Viscosity of 108 seconds Saybolt at 210 R, an oil is secured having a viscosity of 717 seconds Saybolt at 100 F. and a cold test of 35 F. or l.'7 C. The treatment of dodecylene in a similar manner likewise produces an oil of low sensitiveness to temperature changes.
Other known polymerizing agents having a similar action to aluminum chloride may likewise be employed, such as boron fluoride, zinc chloride, ferric chloride, and the like.
We claim:
1. In the method of producing a synthetic lubricating oil wherein an olefin hydrocarbon is subjected to the polymerizing action of a catalytic quantity of aluminum chloride at a temperature below 100 0;, the aluminum chloride forms a sludge with a portion of the olefin material which is separated from the polymerized oil and the separated oil is freed from hydrochloric acid, the improvement which comprises employing as the initial olefin material normal olefin hydrocarbons having at least 8 carbon atoms and substantially free from lower molecular weight olefins, whereby there is produced lubricating oils of abnormally low viscosity temperature coefiicient.
2. The process of producing synthetic lubricating oils of low viscosity temperature coefiicient, which comprises subjecting a normal olefin hydrocarbon material, consisting principally of olefins having between 8 and 16 carbon atoms to the action of from 1 to 5% of aluminum chloride at a temperature not exceeding 100 C. whereby the olefin hydrocarbon is. polymerized to a viscous oil and the aluminum chloride is converted into a sludge, separating said sludge from said oil, neutralizing said oil and subjecting it to distillation to obtain the desired product.
3. The process of producing a synthetic lubricating oil having a viscosity temperature coefficient less than that of a Pennsylvania lubricating oil of equivalent viscosity, comprising subjecting a normal olefin hydrocarbon. having between 8 and 16 carbon atoms to the action of a catalytic quantity of aluminum chloride at a temperature not exceeding 100 C. whereby the olefin hydrocarbon is polymerized to a viscous oil and the aluminum chloride is converted into a sludge, separating said sludge from said oil, neutralizing said oil and subjecting it to distillation to obtain the desired product.
4. The process of claim 3 wherein the normal olefin hydrocarbon employed is normal octene.
5, The process of claim 3 wherein the normal olefin hydrocarbon employed is normal duodecylene.
6'. The process of claim 3 wherein the normal olefin hydrocarbon employed is cetene.
7. In the method of producing a synthetic lubricating oil whereinan olefin hydrocarbon is subjected to the polymerizing action of a catalyst selected from the class consisting of aluminum
US524412A 1931-03-21 1931-03-21 Synthesis of lubricating oils Expired - Lifetime US2091398A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US524412A US2091398A (en) 1931-03-21 1931-03-21 Synthesis of lubricating oils

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US524412A US2091398A (en) 1931-03-21 1931-03-21 Synthesis of lubricating oils

Publications (1)

Publication Number Publication Date
US2091398A true US2091398A (en) 1937-08-31

Family

ID=24089105

Family Applications (1)

Application Number Title Priority Date Filing Date
US524412A Expired - Lifetime US2091398A (en) 1931-03-21 1931-03-21 Synthesis of lubricating oils

Country Status (1)

Country Link
US (1) US2091398A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2462360A (en) * 1949-02-22 Method of preparing lubricating
US2500161A (en) * 1948-08-14 1950-03-14 Socony Vacuum Oil Co Inc Conversion of 1-olefins in the presence of lead tetraacetate
US2620365A (en) * 1949-03-30 1952-12-02 Standard Oil Co Synthetic lubricating oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2462360A (en) * 1949-02-22 Method of preparing lubricating
US2500161A (en) * 1948-08-14 1950-03-14 Socony Vacuum Oil Co Inc Conversion of 1-olefins in the presence of lead tetraacetate
US2620365A (en) * 1949-03-30 1952-12-02 Standard Oil Co Synthetic lubricating oil

Similar Documents

Publication Publication Date Title
US2890161A (en) Production of low cold-test oils using urea
US2312750A (en) Sulphurized addition agent for lubricants and lubricants containing the same
Sullivan Jr et al. Synthetic Lubricating Oils Relation between Chemical Constitution and Physical Properties
US3842134A (en) Polymerization process
US2507731A (en) Process of reacting phosphorus sulfide and olefinic hydrocarbon
US2421082A (en) Lubricant
US2091398A (en) Synthesis of lubricating oils
US2172146A (en) Manufacture of iso-butane
US2389240A (en) Process for the conversion of hydrocarbons
US2189924A (en) Products of hydrocarbons
US2301052A (en) Polymerized hydrocarbon oils
US2357926A (en) Polymerization
US2239533A (en) Pour point depressant
US2822332A (en) Lubricating oil additive and method of preparing the same
US3478113A (en) Hydrocarbon hydraulic oil
US1998350A (en) Process for improving lubricating oils
US2388942A (en) Conversion of hydrocarbons
US2219867A (en) Impregnation of leather and products thereof
US2469725A (en) Synthetic lubrication oil
US2129752A (en) Settling aid in heavy solvents
US2308184A (en) Art of producing wax modifying agents
US2084082A (en) Method of polymerizing olefin hydrocarbons
US1970402A (en) Art of producing lubricating oils
US2288392A (en) Condensation product of aryl amine and long chain aliphatic compound
US2245639A (en) Pour depressor