EP0350165A1 - Verfahren, um das Wachstum von aerobischen Pilzen in wasserhaltigen Kohlenwasserstoffen zu verhindern - Google Patents

Verfahren, um das Wachstum von aerobischen Pilzen in wasserhaltigen Kohlenwasserstoffen zu verhindern Download PDF

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Publication number
EP0350165A1
EP0350165A1 EP89305807A EP89305807A EP0350165A1 EP 0350165 A1 EP0350165 A1 EP 0350165A1 EP 89305807 A EP89305807 A EP 89305807A EP 89305807 A EP89305807 A EP 89305807A EP 0350165 A1 EP0350165 A1 EP 0350165A1
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EP
European Patent Office
Prior art keywords
boron
additive
hydrocarbyl
process according
hydrocarbon
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.)
Granted
Application number
EP89305807A
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English (en)
French (fr)
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EP0350165B1 (de
Inventor
Leif Bp Chemicals Hammer (Additives)
Benny Bp Chemicals Smith (Additives)
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.)
Lubrizol Adibis Holdings UK Ltd
Original Assignee
BP Chemicals Additives Ltd
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Publication of EP0350165A1 publication Critical patent/EP0350165A1/de
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/12—Inorganic compounds
    • C10L1/1291—Silicon and boron containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to a method for preventing the growth of aerobic fungi in aqueous hydrocarbons, for example middle distillate fuels, by addition thereto of a material having biostatic activity and to aqueous hydrocarbon compositions containing such material having biostatic activity.
  • compositions comprising a hydrocarbyl-substituted succinimide in which the hydrocarbyl substituent is of sufficient size to impart hydrocarbon solubility and boron provides at least some of the aforesaid needs.
  • US-A-4,092,127 discloses a fuel to which has been added, in an amount sufficient to provide from about 80 to 400 parts per million by weight of boron of an anti-dieseling combination of :-
  • US-A-4,184,851 discloses a fuel composition which comprises a major proportion, i.e. more than 50% by weight, of a distillate petroleum fraction preferably having an atmospheric boiling range of from about 120°C to about 400°C and from about 0.001 to 1.0 wt % of borated oil-soluble succinamic acid or its derivative having the following formula:- wherein R is a straight chain aliphatic hydrocarbon group having from 0 to 1 site of olefinic unsaturation (alkyl or alkenyl) attached at a secondary carbon atom to the succinyl group and is of at least 8 carbon atoms, generally in the range of 14 to 40 carbon atoms and more usually in the range of 15 to 30 carbon atoms; one of X and X1 is hydroxyl and the other is -NYY1 wherein N has its normal meaning of nitrogen and Y and Y1 are aliphatic hydrocarbyl groups of from 8 to 40 carbon atoms, more usually of from 14 to 30 carbon atoms,
  • the additive comprises boron and a hydrocarbyl-substituted succinimide in which the hydrocarbyl substituent is of a size sufficient to impart hydrocarbon solubility.
  • the present invention provides a fuel composition
  • a fuel composition comprising a hydrocarbon contaminated with water and a fungal growth inhibiting amount of an additive characterised in that the additive comprises boron and a hydrocarbyl-substituted succinimide in which the hydrocarbyl substituent is of a size sufficient to impart hydrocarbon solubility.
  • Hydrocarbyl-substituted succinimides are well known as dispersant additives in lubricating oils, see for example GB-A-922,831; GB-A-1565627 and EP-A-0031236 as representative of the extensive patent literature on this subject. Both mono- and bis-succinimides may be employed.
  • the hydrocarbyl substituent may suitably be a substantial saturated hydrocarbyl group containing from about 20 to about 300 carbon atoms, preferably from about 40 to 150 carbon atoms.
  • the substantially saturated hydrocarbyl group is preferably derived from a polyolefin, more preferably from a polyisobutene.
  • the boron may be present in the additive either in the form of a physical admixture with or chemically bound to the hydrocarbyl-substituted succinimide.
  • boron may suitably be present as a boron compound, preferably in the form of a particulate dispersion thereof, suitably incorporating also a carrier for the boron compound.
  • the boron compound may be present as boric acid or a boron salt.
  • the boron compound is preferably in the form of the ammonium salt of boric acid.
  • the carrier may be a hydrocarbon-compatible high-boiling material.
  • Suitable carrier materials include mineral oils which may be solvent refined or otherwise, synthetic lubricating oils, for example of the ester type, liquid polyolefins, for example low molecular weight polyisobutenes, or their oxidised or aminated derivatives, amino and hydroxy derivatives of polyolefins, or liquid olefin copolymers.
  • the carrier may also comprise the hydrocarbyl succinimide component.
  • the mean particle size of the particulate dispersion may suitably be less than 1 micron, preferably less than 0.5 micron.
  • a suitable dispersion of the boron compound may be prepared by wholly or partially desolvating a solvent-in-carrier emulsion of a solution of the boron compound in the presence or absence of the hydrocarbyl-substituted succinimide, preferably in its presence.
  • Suitable solvents for the boron compound include hydrocarbons and substituted hydrocarbons of relatively low boiling point and water, water being preferred.
  • the hydrocarbon may be any hydrocarbon which is susceptible to fungal growth in the presence of water and oxygen.
  • the hydrocarbon may be a crude oil or a crude oil distillate fraction. Suitable hydrocarbon fractions include gasoline, diesel fuel, heavy marine fuels and fuel oils including both domestic and industrial heating oils. Whatever, the hydrocarbon, it is contaminated with water, which may be present in amounts as low as 0.1% w/w, or less.
  • the amount of the additive suitably employed may conveniently be defined in terms of the amount of boron incorporated into the fuel.
  • the amount of additive used may be sufficient to provide up to 500, more generally up to 200 ppm wt in the hydrocarbon.
  • the additive may suitably be compounded with other additives conventionally employed in fuel compositions, for example in the case of a diesel fuel composition the additive package may further incorporate at least one of an anti-rust agent, an anti-foam agent, an antioxidant and a demulsifier. It is an advantage of the additives of the present invention that in addition to providing biostatic activity, they also provide dispersant properties, i.e. they behave as multifunctional additives.
  • polyisobutene mono-succinimide designated hereinafter as PMS
  • PMS polyisobutene (molecular weight about 1000) substituted succinic anhydride 1:1 adduct of tetraethylpentamine (TEPA)
  • PBS polyisobutene bis-succinimide
  • PBS polyisobutene (molecular weight about 1000) substituted succinic anhydride 2:1 product of TEPA was employed.
  • the additives (a) - (d) were compounded into a multi-functional diesel fuel additive package which was tested in diesel fuel.
  • the package contained an anti-rust agent, an anti-foam agent, a demulsifier and an antioxidant.
  • test fuels A - H were tested with 4 fungal strains using a method described by Smith and Crook. [The germination and growth of Cladosporium resinae in fuel oil, 'Biodeterioration. The Proceedings of the Fourth International Biodeterioration Symposium, Berlin' (T.A. Oxley, G. Becker and D. Allsopp, eds) Pitman, London, pp 29-36, 1980].
  • sterile aqueous medium in test tubes is innoculated with a suspension of fungal spores and then overlaid with fuel containing known levels of test additives. Tubes are incubated for ca . 28 days and examined periodically for development of the fungi at the fuel/water interface.
  • test fuel (I) containing no additive was tested.
  • test fuel (Biobor JF, ex US Borax) was tested in test fuels X and Y (270 ppm level).
  • Mould cultures were grown initially on Sabouraud Dextrose Agar slopes (5 slopes of each strain) for 10 days at 27°C. Sterile quarter strength Ringers solution (5 ml) was added to each slope and shaken to obtain a conidial (spore) suspension. The suspensions were then spun in a Sorvall Superspeed centrifuge type SS3 at 5000 rpm for 15 minutes. The conidial pellet was washed once with sterile quarter strength Ringers solution and the suspension adjusted to give a final concentration of 106 conidia per ml.
  • Mains tap water, enriched with 10% Bushnell and Haas medium a mineral salts medium for the culture of hydrocarbon utilising fungi consisting of NH4NO3 (1 g), KH2PO4 (1 g), K2HPO4 (1 g), MgSO4 (0.2 g), FeCl3 (0.01 g), CaCl2 (0.02 g), distilled water (1 litre), pH 7.0 ⁇ 0.3, autoclaved at 121°C for 15 minutes (Bushnell, L.D. and Haas, H.F., J.
  • yeast extract was dispensed in 2.5 ml aliquots in 20 ml Bellco screw capped glass test-tubes and then sterilised by autoclaving at 121°C for 15 minutes. A series of tubes was then inoculated with 1 drop of conidial suspension using a sterile Pasteur pipette. A 2.5 ml aliquot of test fuel was then overlaid on the aqueous medium. Uninoculated aqueous medium overlaid with test fuel was used as control. Five replicates were used for each fuel sample. The procedure was repeated for all four test species.
  • control fuels i.e. diesel fuel minus additives and diesel fuel containing the jet fuel biocide, Biobor JF (Borax Holdings Limited) at a concentration of 270 ppm (20 ppm boron), were laid over inoculated and uninoculated medium as above.
  • SCORE A The degree of fungal colony development in the water was estimated as nil (0), feeble (+), good (++) or very good (+++) and this was converted to a numerical score, viz 0, 1, 2 or 3 (SCORE B).
  • Biobor JF was ineffective in protecting the interface except in the case of Cladosporium .

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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)
  • Lubricants (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP89305807A 1988-06-29 1989-06-08 Verfahren, um das Wachstum von aerobischen Pilzen in wasserhaltigen Kohlenwasserstoffen zu verhindern Expired - Lifetime EP0350165B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888815424A GB8815424D0 (en) 1988-06-29 1988-06-29 Chemical process
GB8815424 1988-06-29

Publications (2)

Publication Number Publication Date
EP0350165A1 true EP0350165A1 (de) 1990-01-10
EP0350165B1 EP0350165B1 (de) 1996-02-07

Family

ID=10639542

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89305807A Expired - Lifetime EP0350165B1 (de) 1988-06-29 1989-06-08 Verfahren, um das Wachstum von aerobischen Pilzen in wasserhaltigen Kohlenwasserstoffen zu verhindern

Country Status (9)

Country Link
EP (1) EP0350165B1 (de)
JP (1) JP2730763B2 (de)
DE (1) DE68925601T2 (de)
DK (1) DK320589A (de)
FI (1) FI96913C (de)
GB (1) GB8815424D0 (de)
GR (1) GR3018936T3 (de)
MY (1) MY131038A (de)
NO (1) NO303838B1 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6368369B1 (en) 2000-01-20 2002-04-09 Advanced Lubrication Technology, Inc. Liquid hydrocarbon fuel compositions containing a stable boric acid suspension
WO2001053435A3 (en) * 2000-01-20 2002-04-25 Mohan L Sanduja Liquid compositions containing a stable boric acid suspension
EP2427535A4 (de) * 2009-05-08 2017-03-15 Triboron International AB Verfahren zur herstellung einer stabilen borlösung
EP3532575A4 (de) * 2016-10-27 2020-07-01 Triboron International AB Verfahren zur verhinderung von mikrobiellem wachstum und mikrobiologisch beeinflusster korrosion bei einem biologisch abbaubaren und/oder erneuerbaren brennstoff, einer hydraulischen flüssigkeit und/oder einem schmiermittel

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3203137A1 (en) * 2020-12-11 2022-06-16 Shell Internationale Research Maatschappij B.V. Use of a detergent additive

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE653601C (de) * 1936-02-24 1937-11-27 Oerlikon Maschf Einphasenkondensatormotor fuer Umkehr der Drehrichtung
US2680058A (en) * 1948-04-27 1954-06-01 Texaco Development Corp Preservation of petroleum in storage
GB773169A (en) * 1955-06-06 1957-04-24 Standard Oil Co Improvements in or relating to motor fuel
FR1288969A (fr) * 1960-03-08 1962-03-30 United States Borax Chem Perfectionnements au traitement des pétroles et fractions de pétrole
GB994496A (en) * 1962-06-11 1965-06-10 United States Borax Chem Quaternary ammonium glycol monoborate salts
US3203971A (en) * 1961-02-21 1965-08-31 Standard Oil Co Glycol borate amine salts
US3325262A (en) * 1963-08-01 1967-06-13 Standard Oil Co Glycol borate amine salts and compositions containing the same
US3347646A (en) * 1967-01-16 1967-10-17 Standard Oil Co Preservation of kerosine during distribution and storage
US3443918A (en) * 1965-09-21 1969-05-13 Chevron Res Gasoline composition
US3991056A (en) * 1973-04-12 1976-11-09 Toa Nenryo Kogyo Kabushiki Kaisha Ashless detergent dispersant
FR2374403A1 (fr) * 1976-12-20 1978-07-13 Exxon Research Engineering Co Additif pour essence pour moteur a allumage par etincelles
US4440656A (en) * 1981-11-23 1984-04-03 Mobil Oil Corporation Borated alkoxylated alcohols and lubricants and liquid fuels containing same
US4718919A (en) * 1986-10-01 1988-01-12 Ppg Industries, Inc. Fuel additive

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU46860A1 (de) * 1964-03-23 1964-11-03

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE653601C (de) * 1936-02-24 1937-11-27 Oerlikon Maschf Einphasenkondensatormotor fuer Umkehr der Drehrichtung
US2680058A (en) * 1948-04-27 1954-06-01 Texaco Development Corp Preservation of petroleum in storage
GB773169A (en) * 1955-06-06 1957-04-24 Standard Oil Co Improvements in or relating to motor fuel
FR1288969A (fr) * 1960-03-08 1962-03-30 United States Borax Chem Perfectionnements au traitement des pétroles et fractions de pétrole
US3203971A (en) * 1961-02-21 1965-08-31 Standard Oil Co Glycol borate amine salts
GB994496A (en) * 1962-06-11 1965-06-10 United States Borax Chem Quaternary ammonium glycol monoborate salts
US3325262A (en) * 1963-08-01 1967-06-13 Standard Oil Co Glycol borate amine salts and compositions containing the same
US3443918A (en) * 1965-09-21 1969-05-13 Chevron Res Gasoline composition
US3347646A (en) * 1967-01-16 1967-10-17 Standard Oil Co Preservation of kerosine during distribution and storage
US3991056A (en) * 1973-04-12 1976-11-09 Toa Nenryo Kogyo Kabushiki Kaisha Ashless detergent dispersant
FR2374403A1 (fr) * 1976-12-20 1978-07-13 Exxon Research Engineering Co Additif pour essence pour moteur a allumage par etincelles
US4440656A (en) * 1981-11-23 1984-04-03 Mobil Oil Corporation Borated alkoxylated alcohols and lubricants and liquid fuels containing same
US4718919A (en) * 1986-10-01 1988-01-12 Ppg Industries, Inc. Fuel additive

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6368369B1 (en) 2000-01-20 2002-04-09 Advanced Lubrication Technology, Inc. Liquid hydrocarbon fuel compositions containing a stable boric acid suspension
WO2001053435A3 (en) * 2000-01-20 2002-04-25 Mohan L Sanduja Liquid compositions containing a stable boric acid suspension
US6645262B1 (en) 2000-01-20 2003-11-11 Advanced Lubrication Technology, Inc. Liquid hydrocarbon fuel compositions containing a stable boric acid suspension
EP2427535A4 (de) * 2009-05-08 2017-03-15 Triboron International AB Verfahren zur herstellung einer stabilen borlösung
US9688937B2 (en) 2009-05-08 2017-06-27 Triboron International Ab Method for producing a stable boric solution
EP3532575A4 (de) * 2016-10-27 2020-07-01 Triboron International AB Verfahren zur verhinderung von mikrobiellem wachstum und mikrobiologisch beeinflusster korrosion bei einem biologisch abbaubaren und/oder erneuerbaren brennstoff, einer hydraulischen flüssigkeit und/oder einem schmiermittel

Also Published As

Publication number Publication date
JP2730763B2 (ja) 1998-03-25
FI893194L (fi) 1989-12-30
EP0350165B1 (de) 1996-02-07
GB8815424D0 (en) 1988-08-03
JPH0247195A (ja) 1990-02-16
DE68925601T2 (de) 1996-06-20
NO892686D0 (no) 1989-06-28
FI893194A0 (fi) 1989-06-29
GR3018936T3 (en) 1996-05-31
DK320589D0 (da) 1989-06-28
DK320589A (da) 1989-12-30
DE68925601D1 (de) 1996-03-21
NO303838B1 (no) 1998-09-07
FI96913C (fi) 1996-09-25
FI96913B (fi) 1996-06-14
MY131038A (en) 2007-07-31
NO892686L (no) 1990-01-02

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