EP0144423A1 - Melanges liquefies d'oxydes de trialkylphosphine - Google Patents

Melanges liquefies d'oxydes de trialkylphosphine

Info

Publication number
EP0144423A1
EP0144423A1 EP84902843A EP84902843A EP0144423A1 EP 0144423 A1 EP0144423 A1 EP 0144423A1 EP 84902843 A EP84902843 A EP 84902843A EP 84902843 A EP84902843 A EP 84902843A EP 0144423 A1 EP0144423 A1 EP 0144423A1
Authority
EP
European Patent Office
Prior art keywords
trialkylphosphine oxides
trialkylphosphine
liquefied
oxides
mixtures
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.)
Withdrawn
Application number
EP84902843A
Other languages
German (de)
English (en)
Inventor
Richard Williamson Cummins
Burton Murry Baum
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.)
FMC Corp
Original Assignee
FMC Corp
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 FMC Corp filed Critical FMC Corp
Publication of EP0144423A1 publication Critical patent/EP0144423A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • This invention relates to phosphine oxides, and in particular to liquefied mixtures of tr ialkylphosphine oxides useful as components in aircraft hydraulic fluids and in other formulations.
  • Modern aircraft are equipped with a number of hydraulically actuated mechanisms such as brakes, power steering for taxiing, landing gear, control surfaces, that is, wing flaps, elevator, rudder and the like.
  • the quantity of hydraulic fluid that must be carried can be substantial upwards of about 175 gallons.
  • the substitution of a hydraulic fluid with a specific gravity of 0.878 instead of 1.00 amounts to a weight savings of about 200 pounds over the commonly used phosphate ester based hydraulic fluids.
  • a comparable product having a lower specific gravity would be of benefit to the aircraft industry.
  • liquid mixed trialkylphosphine oxides are excellent base stocks in the formulation of low density hydraulic fluids and the provision of such compositions and their use in hydraulic devices and processes constitutes the principal objects and purposes of the invention.
  • trialkylphosphine oxides are obtained by combining individual members to provide mixtures which through mutual melting point depression remain in the liquid state.
  • trialkylphosphine oxides as single compounds, are highly crystalline solids. Although they constitute a known chemical series, trialkylphosphine oxides have not, so far as can be ascertained, been prepared and utilized as liquefied mixtures.
  • trialkylphosphine oxides can be selected in which the alkyls are alike or dif ferent with respect to their isomeric configuration and number of carbon atoms.
  • a mixture of trialkylphosphine oxides in which the number of carbon atoms per alkyl is 6 to 10 would include a large number of homologous and isomeric compounds.
  • the synthesis of sufficient numbers of different structures in order to provide and maintain stable liquefied mixtures can be arduous and time-consuming.
  • reaction sequence is conducted by introducing phosphine into a molar excess of the monoolefin mixture in the presence of the radical initiator under inert conditions at moderately elevated temperatures about 80°C to about 120°C.
  • the resulting intermediate phosphines are then oxidized, preferably with hydrogen peroxide, to the corresponding mixed phosphine oxide.
  • Suitable radical initiators include any number of compounds which are photochemically or thermochemically decomposed to form free radicals under the reactive conditions.
  • a preferred radical initiator is azobisisobutyronitrile.
  • the reaction was carried out following the procedure for preparing individual trialkylphosphine oxides as set forth in U. S. Patent No. 2,803,597 to Stiles and J. Org. Chem. 26, 5138 (1961).
  • the hydraulic fluids of the invention will normally contain very minor amounts, typically about 0.01% to about 5.0% by weight of various additives of the type normally incorporated in formulating hydraulic fluid compositions such as antioxidants, rust inhibitors, corrosion inhibitors, antifoam agents, antiwear agents, cavitation inhibitors, pour point depressants, and other special purpose additives.
  • various additives of the type normally incorporated in formulating hydraulic fluid compositions such as antioxidants, rust inhibitors, corrosion inhibitors, antifoam agents, antiwear agents, cavitation inhibitors, pour point depressants, and other special purpose additives.
  • Rust and corrosion inhibitors commonly employed include benzothiazole, benzotr iazole, tr iethanolamine, phenothiazine, trialkyl phosphites, N-acrylsarcosines, propyl gallate, succinic acid and alkylsuccinic acids.
  • Additives to inhibit foaming and cavitation include organosilicones, dialkyl carboxylic acid esters such as diethyl succinate or dioctyl sebacate.
  • Antioxidants include dialkylthiodipropionate, for example, dilaurylthiodipropionate, etc., organic amines, for example, diphenylamine, phenylnaphthylamine, hindered phenols, etc.
  • the herein trialkylphosphine oxides are characterized by exceptionally low density and are thus particularly suitable as the base stock in hydraulic fluids for aircraft.
  • the common commercial phosphate ester type hydraulic fluids for example, tributylphosphate and dibutylphenylphosphate have a specific gravity of about at least 1.000
  • the trialkylphosphine oxides of the invention exhibit an average specific gravity of about 0.878. This translates into substantial weight savings for large commercial airliners such as the 747 which has a hydraulic fluid capacity of about 175 gallons.
  • reaction mixture was vacuum stripped at 100°C and 30-50 mm Hg (4 to 6.7 kPa) to remove toluene and unreacted olefins and the residue taken up in 600 ml of isopropyl alcohol and oxidized by the dropwise addition of 122 ml of 30% hydrogen peroxide (1.08 moles).
  • the oxidized mixture was vacuum stripped at 30°C and 5 mm Hg (667 Pa) to give 559 g of crude tri(C 6 -C 8 -C 10 ) phosphine oxide corresponding to 96.5% of theory based on phosphine.
  • the crude product having an acid number of > 4, was dissolved in 300 ml of petroleum ether and stirred for 3 hours with 250 ml of saturated aqueous Na 2 CO 3 solution and 100 ml of saturated aqueous NaCl solution. After phase separation and vacuum stripping at 30°C and
  • the herein liquefied trialkylphosphine oxide mixtures exhibit antistatic properties as evidenced by the marked decrease in volume resistivity of thermoplastic polymers in which such phosphine oxides have been incorporated.
  • the liquefied trialkylphosphine oxide mixtures possess other useful and valuable characteristics. For instance, liquid decyl hexyl octylphosphine oxide, a representative member of the series obtained by reacting molar proportions of 1-hexene, 1-octene and 1-decene with phosphine followed by oxidation of the reaction mixture, is capable of plasticizing nylon.
  • Plastic films containing the liquid trialkylphosphine oxides of the invention are rendered more transparent.
  • polyethylene film which tends to be milky or hazy, was obtained in highly clarified form. Similar results were realized with nylon film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Abstract

Oxydes de trialkylphosphine mélangés liquéfiés utiles dans la composition de fluides hydrauliques de faible densité.
EP84902843A 1983-06-13 1984-05-24 Melanges liquefies d'oxydes de trialkylphosphine Withdrawn EP0144423A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US50395983A 1983-06-13 1983-06-13
US503959 1983-06-13

Publications (1)

Publication Number Publication Date
EP0144423A1 true EP0144423A1 (fr) 1985-06-19

Family

ID=24004246

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84902843A Withdrawn EP0144423A1 (fr) 1983-06-13 1984-05-24 Melanges liquefies d'oxydes de trialkylphosphine

Country Status (2)

Country Link
EP (1) EP0144423A1 (fr)
WO (1) WO1984004923A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2191490B (en) * 1986-06-10 1990-06-27 East China Inst Of Chemical Te Process for the recovery of carboxylic acids from fermentation broth
GB9117603D0 (en) * 1991-08-15 1991-10-02 Albright & Wilson Organophorus compounds
CN102180903A (zh) * 2011-03-10 2011-09-14 常熟新特化工有限公司 一种三正辛基氧化膦的制备方法
CN114174309A (zh) * 2019-07-29 2022-03-11 赢创运营有限公司 从水性培养基中萃取碳酸、脂族酸、酯和醇的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803597A (en) * 1949-04-30 1957-08-20 Shell Dev Process for producing organic phosphines
US3666543A (en) * 1969-11-24 1972-05-30 Ludwig Maier Tris-(2-hydroxyalkyl)-phosphine oxide flame retardant articles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8404923A1 *

Also Published As

Publication number Publication date
WO1984004923A1 (fr) 1984-12-20

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Legal Events

Date Code Title Description
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

AK Designated contracting states

Designated state(s): BE DE FR GB LU NL

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19850614

RIN1 Information on inventor provided before grant (corrected)

Inventor name: CUMMINS, RICHARD, WILLIAMSON

Inventor name: BAUM, BURTON, MURRY