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US2073080A - Process for lowering the pour points of mineral oils - Google Patents

Process for lowering the pour points of mineral oils Download PDF

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Publication number
US2073080A
US2073080A US683298A US68329833A US2073080A US 2073080 A US2073080 A US 2073080A US 683298 A US683298 A US 683298A US 68329833 A US68329833 A US 68329833A US 2073080 A US2073080 A US 2073080A
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United States
Prior art keywords
hydrocarbons
pour point
grams
oil
product
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
US683298A
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English (en)
Inventor
Adrianus Johannes Van Peski
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Shell Development Co
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Shell Development Co
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Filing date
Publication date
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Publication of US2073080A publication Critical patent/US2073080A/en
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/135Steam engines or turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/30Refrigerators lubricants or compressors lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/32Wires, ropes or cables lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/34Lubricating-sealants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/36Release agents or mold release agents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/38Conveyors or chain belts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/40Generators or electric motors in oil or gas winning field
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/42Flashing oils or marking oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/44Super vacuum or supercritical use
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/50Medical uses

Definitions

  • pour point reducing agents of greater power than those formerly known can be obtained by using for their manufacture highly condensed cyclic hydrocarbons of compound cyclic structures instead of the simple 4 aromatic hydrocarbons mentioned above.
  • These highly condensed cyclic hydrocarbons may be found as naturally present in certain materials, in which case such mixtures may be used, if desired, as initial stock material for the coupling .-reaction with high molecular parafilnic hydro- I carbons.
  • the following are examples of materials containing highly condensed cyclic hydrocarbons, viz. high boiling Edeleanu extracts or polymers thereof, cracked high boiling distillates 50 or residues.
  • the latter materials contain, inter alia, crackene, a highly condensed aromatic hy-- drocarbon, which when coupled to one of the higher parafilnic hydrocarbons yields a product .with a strong pour point reducing action.
  • Liquid materials of the type of Edeleanu extracts and August cracked residues may be regarded as solutions of aromatic hydrocarbons.
  • the highly condensed cyclic hydrocarbons can also be obtained by subjecting cyclic and particularly aromatic hydrocarbons with or without side 5 chains (partly. or completely hydrogenated, if desired), substituted or not, or derivatives thereof, such as alkyl-aryl, oxy-aryl, or other similar compounds, their homologues and/or analogues,
  • a few examples ;of substances which can be worked up into the desired highly condensed cyclic hydrocarbons are: benzene, naphthalene, anthracene, phenan- 15 threne, tetraline, dihydroanthracene, methylnaphthalene, fluoranthene, chrysene, retene, their homologues and hydrogenation products. It is, however, also possible to start with mixtures or solutions containing these or.
  • metal halides such as aluminium chloride, zinc chloride, ferric chloride, boron fluoride and the like, may be used as condensing agents.
  • the highly condensed cyclic organic compounds may be coupled, or condensed, with a parafllnic hydrocarbon, or a mixture of such hydrocarbons, 40 by any known method, such, for example, as one of those described by Sabatier inhisflatalysis in Organic Chemistry, Chapter XX.
  • the products obtained by condensation of highly condensed cyclic compounds with high molecular paraflinic hydrocarbons can b'subjected to an extraction treatment with selective solvents whereby a separationinto'active' and inactive constituents is effected.
  • Chlorinated parafiin wax prepared in a conventional manner and containing 14.8% C1 was used as a source of parafiinic: radicles to be coupled onto the condensed aromatic nuclei. This coupling was carried out by heating 15 grams of the above condensation product with 40 grams of the chlorinated paraflin wax, at 50-60 C. for about 24 hours in the presence of anhydrous AlCls and about 50 cm of carbon bisulphide. Thereafter the product was separated from the sludge, washed with water and lye and then the constituents boiling below 300 C. were removed by steam distillation. The product thus obtained, when added in a quantity of 0.3% by weight to a Pennsylvania oil having a pour pointof 0 C., lowered the pour point by 15 C.
  • Picene was prepared by heating 3 parts by weight of napththalene with 1 part by weight of aluminium chloride during 10 hours at C., diluting the resulting product with benzene, washing with iced water and eliminating the benzene and non-converted napthalene by steam distillation and small quantities of formed dinaphthyl by distillation in vacuo until the temperature of the liquid is about 270 C. at a pressure of 10 mm.
  • a condensation product of picene with 3 mol. of chlorinated paraffin wax was obtained by stirring 20 grams of picene with 60 grams" of chlorinated paraflin wax and 20 grams of AlCls in cm of kerosene during 24 hours at room temperature,- allowing the temperature to rise slowly to about 90 0., Washing out with water in order to eliminate the AlCla and removing the excess of kerosene and paraflin wax by distillation in a current of nitrogen (in order to exclude the influence of oxygen).
  • 0.5% of the resulting product to a Pennsylvania turbine oil having a pour point of 0 C., a pour point reduction of 5 C. is obtained.
  • addiligg 2% the reduction amounts to more than A product prepared in exactly the same manner by condensation of 1 mol. of napththalene with 3 mol. of chlorinated paraflin wax, when added in a quantity of 0.5% to the same Pennsylvania oil did practically not lower the pour point; 2% gave a pour point reduction of 1 C.
  • a condensation product of picene with 2 mol. of chlorinated paraifin wax was prepared by heating 20 grams of picene with 40 grams of chlorinated paraflin wax and 20 grams of A1613 in 50 cm CS2 during 15 hours at 50-60 C. whilst using a reflux condenser. 0.5% of the resulting product, when added to a Pennsylvania turbine oil, gave a pour point reduction of 9 C. After removing the excess of paraflin wax by distillation, as described in Example 2, 0.5% gave a reduction of 21 C. By extraction with butanone 15 grams of the product was separated into 9 grams insoluble in butanone and 6 grams'soluble in butanone. 0.5% of the insoluble part gave a pour point reduction of more than 20 0., Whilst the soluble part was inactive with regard to Pennsylvania turbine oil.
  • a few tenths per cent of the products manufactured by coupling highly condensed aromatic hydrocarbons with higher paraflinic hydrocar- 7 0 residue after being treated with an excess of 98% bons added to, say lubricating oils, is, as a rule, already sufiicient to obtain a pour point reduction of l0-30 C. dependent on the pour point of the oil to be treated.
  • the products are generally applicable to various kinds of hydrocarbon oils, e. g. natural as well as synthetic lubricating oils (manufactured from mineral or tar oils), fuel oils, oil residues, etc.
  • the compounds in question can be used in drilling wells, in order to prevent the deposition of well-wax.
  • a process for lowering the pour point of mineral oil which comprises incorporating therein a small quantity of an alkylated, highly condensed cyclic hydrocarbon having high molecular paraiiinic side chains, and having nuclei containing more than three aromatic or hydrogenated rings.
  • a process for lowering the pour point of mineral oil which comprises incorporating therein less than 1% of the product obtained by the condensation of halogenated high molecular paraflinic hydrocarbons with highly condensed cyclic hydrocarbons selected from the group consisting oi cyclic hydrocarbons having more than three aromatic or hydrogenated rings in their molecules, and concentrated solutions of such polycyclic hydrocarbons obtained by the condensation of extracts obtained inrefining mineral oils containing cyclic hydrocarbons with selective solvents for non-parafllnic hydrocarbons.
  • a process for lowering the pour point of mineral oil which comprises incorporating therein less than 1% of the product obtained by the condensation of halogenated high molecular parafilnic hydrocarbons with a mixture of pre-condensed cyclic hydrocarbons selected from the group consisting of cyclic hydrocarbons having more than three aromatic or hydrogenated rings in their molecules, and concentrated solutions of such polycyclic hydrocarbons obtained by the condensation of extracts obtained in refining mineral oils containing cyclic hydrocarbons with selective solvents for non-parafilnic hydrocarbons.
  • a mineral oil containing a small quantity sufiicient to reduce the pour point of said mineral oil or an alkylated, highly condensed cyclic hydrocarbon having high molecular paraflinic side chains, and having nuclei containing more than three aromatic or hydrogenated rings is provided.
  • An improved lubricating oil comprising a blend of a viscous hydrocarbon fraction containing a waxy constituent in proportion suflicient to give an undesirably high pour point and a quantity less than 1% out sufllcient to reduce said pour point of an alkylated highly condensed cyclic hydrocarbonhaving high molecular parafllnic side chains, and having nuclei having more than three aromatic or hydrogenated rings.
  • An improved lubricating oil comprising a blend of a viscous hydrocarbon fraction containing' a solid waxy constituent in proportion suflicient to give an undesirably high pour point, and a quantity less than 1% but suflicient to reduce said pour point of alkylated picene having high molecular parafilnic side chainsof the size of normally solid paraflinic hydrocarbons.
  • An improved lubricating oil comprising a blend of a viscous hydrocarbon fraction containing a solid waxy constituent in proportion sufllcient to give an undesirably high pour point, and a quantity less than 1% but suflicient to reduce said pour point of an alkylated, highly condensed cyclic hydrocarbon having high molecular paraifinic side chains of the size of normally solid parafilnic hydrocarbons, and having nuclei of more than three aromatic or hydrogenated rings obtained by condensing liquid SOs-soluble portion of a mineral oil containing cyclic hydrocarbons in the presence of a catalyst.

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  • 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)
  • Lubricants (AREA)
US683298A 1932-08-05 1933-08-02 Process for lowering the pour points of mineral oils Expired - Lifetime US2073080A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL2073080X 1932-08-05

Publications (1)

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US2073080A true US2073080A (en) 1937-03-09

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Application Number Title Priority Date Filing Date
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US (1) US2073080A (zh)
NL (1) NL62123C (zh)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2916447A (en) * 1956-04-26 1959-12-08 Standard Oil Co Lubricant composition
US3036010A (en) * 1958-07-01 1962-05-22 Exxon Standard Sa Non-gassing insulating oils
US3276519A (en) * 1963-05-29 1966-10-04 Halliburton Co Paraffin control method
US4728412A (en) * 1986-09-19 1988-03-01 Amoco Corporation Pour-point depression of crude oils by addition of tar sand bitumen
US4755230A (en) * 1985-01-15 1988-07-05 Baker Oil Tools, Inc. Method of and composition for removing paraffin deposits from hydrocarbon transmission conduits
US10723881B2 (en) * 2014-12-31 2020-07-28 Shell Oil Company Process to prepare a heavy paraffin wax

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2916447A (en) * 1956-04-26 1959-12-08 Standard Oil Co Lubricant composition
US3036010A (en) * 1958-07-01 1962-05-22 Exxon Standard Sa Non-gassing insulating oils
US3276519A (en) * 1963-05-29 1966-10-04 Halliburton Co Paraffin control method
US4755230A (en) * 1985-01-15 1988-07-05 Baker Oil Tools, Inc. Method of and composition for removing paraffin deposits from hydrocarbon transmission conduits
US4728412A (en) * 1986-09-19 1988-03-01 Amoco Corporation Pour-point depression of crude oils by addition of tar sand bitumen
US10723881B2 (en) * 2014-12-31 2020-07-28 Shell Oil Company Process to prepare a heavy paraffin wax

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NL62123C (zh)

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