US3522022A - Corrosion inhibited fuel oils - Google Patents

Corrosion inhibited fuel oils Download PDF

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Publication number
US3522022A
US3522022A US795965A US3522022DA US3522022A US 3522022 A US3522022 A US 3522022A US 795965 A US795965 A US 795965A US 3522022D A US3522022D A US 3522022DA US 3522022 A US3522022 A US 3522022A
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United States
Prior art keywords
weight
acid
carbon atoms
corrosion
parts
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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
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US795965A
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English (en)
Inventor
Adolf May
Heinz Liebscher
Heinz Muller
Engelbert Krempl
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Hoechst AG
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Hoechst AG
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Filing date
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Publication of US3522022A publication Critical patent/US3522022A/en
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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
    • C10L1/14—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
    • C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof

Definitions

  • Oil-soluble organic compounds have hitherto been added to the fuels in order to prevent such corrosion. From US. Pats. 2,330,524, 2,433,243, 2,736,658 and 2,976,179 it is known to use monoor polyamine salts of carboxylic acids as corrosion inhibitors. Furthermore, in US. Pat. 2,790,779 the use of amido-carboxylic acids or of their salts as corrosion inhibitors in liquid fuels has been proposed. However, these products do not satisfy the high requirements of the practice regarding corrosion inhibition.
  • the oiland water-soluble amine salts of the last-mentioned amide-carboxylic acids in addition have the disadvantage of forming in the liquid fuels, if low amounts of water are present, pasty emulsion flocks which cause serious troubles, for example, by clogging burners and filters in heating devices.
  • primary, secondary or tertiary aliphatic amines there may be used especially alkylor alkenyl-amines containing 3 to 8 carbon atoms, as well as cycloalkylamines containing 5 to 7 carbon atoms in the ring.
  • alkylor alkenyl-amines containing 3 to 8 carbon atoms
  • cycloalkylamines containing 5 to 7 carbon atoms in the ring.
  • preferred amines there may be mentioned, for example, isopropylamine, butylamine, hexylamine, triethylamine, iso-octylamine, allylamine, cyclohexylamine, N-methylcyclohexylamine and N,N-dimethyl-cyclohexylamine.
  • alkane-carboxylic acids containing 4 to 15 carbon atoms suitably those containing 6 to 15 carbon atoms.
  • alkane-carboxylic acids containing 4 to 15 carbon atoms suitably those containing 6 to 15 carbon atoms.
  • butyric acid, caprylic acid, caproic acid, capric acid, coconut oil fatty acid as well as mixtures of fatty acids as those contained, for example in the coconut oil first run fatty acid or those contained in mixtures of fatty acids having unbranched and branched alkyl radicals of about 3 to 12 carbon atoms and obtained by the oxidation of paraflin hydrocarbons.
  • suitable acid components of the Formula II there may be mentioned, for example, N-oleyl-N-methylaminoacetic acid, N-lauroyl-N-methyl-aminoacetic acid, N-myristoyl-N-methyl-aminoacetic acid, N-cocosacyl-N- methyl-aminoacetic acid, N-stearoyl-N-methyl-aminoacetic acid, N-palmitoyl-N-methyl-aminoacetic acid and N- lauroyl-N-ethyl-aminoacetic acid.
  • the acids of the Formula I are used in admixture with the acids of the Formula II.
  • the proportion of one of the two acid components must amount to at least 20% by weight.
  • the amine component (a), on the one hand, and the two acid components (b), on the other hand may be used in the stoichiometrical quantitative ratio required for the formation of neutral salts.
  • a small excess of the acid components or suitably, an excess of amine component In general, about 0.9 to 2 gram-equivalents of amine component are used per one gram-equivalent of acid components.
  • mixtures of components (a) and (b) are used as corrosion inhibitors which contain an excess of amine, referred to the equivalent weights.
  • alkylamine is particularly suitable, if acid components with shorter hydrocarbon radicals are used to employ preferably an amine which has more hydrophobic properties, for example N-methylcyclohexylamine.
  • the quantity of corrosion inhibitors of the present invention to be added to the liquid fuels may vary within certain limits, depending on the requirements.
  • the corrosion inhibitors are added in quantities of about 0.0001 to 0.5% by weight, referred to the liquid fuels; preferably, 0.001 to 0.05% by Weight of corrosion inhibitors are used.
  • the excellent corrosion inhibiting action of the additives of the present invention consisting of amines and mixtures of acids of the Formulae I and II, is shown in the following table listing the products as Examples 1-9.
  • the number of the patent in which the respective product has been described is indicated in brackets. As No. 20, the corrosion of fuel oil alone was tested.
  • CORROSION INHIBITION IN FUEL OIL Quantity added (percent by Evalu- No. Additive dissolved in fuel oil EL weight) ation 1...-- Cyclohexylamine salt of a mixture of 75 0.03 parts by weight of N-myristoyl-N-meth- 0. ylamino acetic acid and 25 parts by weight of synthetic first run fatty acid.
  • N,N-dimethyl-cyclohexylamine salt of 0.03 a mixture of 50 parts by weight N-oleoyl- 0. 05 N'methylamino acetic acid and 50 parts by weight of synthetic first run fatty acid. 2
  • the counter-electrode and the measuring electrode are Connected in a closed circuit and the potential between measuring and comparison electrode is recorded by means of a compensation recorder which is connected to the measuring cell over an amplifier having an input impedance of more than 10 ohms.
  • the measuring electrode is subjected to a current load: the voltage is increased over a potentiometer connected to a 50 v. battery until the measuring electrode is loaded with a current density of A./cm. This current density is maintained during the measurements. The course of the potential between measuring and comparison electrode is recorded versus time.
  • the steel sample under current load does not show a constant potential or shows a potential which is distinctly below 1000 mv., the steel sample can be considered as being incompletely or not at all rendered pas sive. Visual examination after the test will show strong surface corrosion and pitting.
  • samples of fuel oil EL to which the corrosion inhibitors indicated in the table had been added, were tested for their tendency to form emulsion flocks.
  • 0.050% by weight of the inhibitor to be tested and, in addition, 0.4 ml. of water were added each time to 1 liter each of the fuel oil. The samples were then vigorously shaken twice for 5 minutes and examined visually for the presence of separated flocks.
  • Liquid fuel oils as claimed in claim 1 which contain 0.001 to 0.05% by weight of the said additives.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Lubricants (AREA)
US795965A 1966-10-07 1969-02-03 Corrosion inhibited fuel oils Expired - Lifetime US3522022A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF0050385 1966-10-07
DEF0051615 1967-02-23

Publications (1)

Publication Number Publication Date
US3522022A true US3522022A (en) 1970-07-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
US795965A Expired - Lifetime US3522022A (en) 1966-10-07 1969-02-03 Corrosion inhibited fuel oils

Country Status (9)

Country Link
US (1) US3522022A (de)
AT (1) AT286477B (de)
BE (1) BE704841A (de)
CH (1) CH503100A (de)
DE (1) DE1645746A1 (de)
GB (1) GB1183399A (de)
NL (1) NL6713367A (de)
NO (1) NO119452B (de)
SE (1) SE305500B (de)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4478604A (en) * 1982-04-01 1984-10-23 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof
US4496368A (en) * 1983-06-17 1985-01-29 Texaco Inc. Isopropylidene malonate-N-alkyl alkylenediamine condensation products
US4640787A (en) * 1982-04-01 1987-02-03 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof
US5300235A (en) * 1991-02-08 1994-04-05 Exxon Chemical Patents Inc. Corrosion inhibitors
US5312459A (en) * 1989-07-25 1994-05-17 Sprugel Friedrich A Additive for liquefied-gas fuels
US5322630A (en) * 1992-05-14 1994-06-21 Exxon Chemical Patents Inc. Amine derivatives as corrosion inhibitors
WO1996038518A1 (en) * 1995-05-30 1996-12-05 Ashland Inc. Additive system for fuel oil
US20060288638A1 (en) * 2005-06-27 2006-12-28 Schwab Scott D Lubricity additive for fuels
US20080060608A1 (en) * 2006-09-07 2008-03-13 Angela Priscilla Breakspear Method and use for the prevention of fuel injector deposits
US20090056203A1 (en) * 2007-08-29 2009-03-05 Baker Hughes Incorporated Branched carboxylic acids as fuel lubricity additives
US20110061292A1 (en) * 2009-09-14 2011-03-17 Baker Hughes Incorporation No-Sulfur Fuel Lubricity Additive

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2649725B1 (fr) * 1989-07-12 1994-01-14 Lapluye Gerard Composition protectrice des metaux, son procede de preparation, et procedes de protection des metaux
FR2661690A1 (fr) * 1989-07-12 1991-11-08 Lapluye Gerard Compositions protectrices des metaux, leur procede de preparation, et leurs procedes de protection des metaux.
DE19747895A1 (de) * 1997-10-30 1999-05-06 Henkel Kgaa Metallbehandlungsflüssigkeit für den neutralen pH-Bereich
JP4383660B2 (ja) * 1998-01-13 2009-12-16 ベイカー ヒューズ インコーポレイテッド 燃料の潤滑性を改善する組成物および方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2330524A (en) * 1941-06-16 1943-09-28 Alox Corp Corrosion inhibitor
US2433243A (en) * 1946-05-21 1947-12-23 Gulf Oil Corp Diesel fuel oils
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2736658A (en) * 1952-07-23 1956-02-28 Armour & Co Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions
US2790779A (en) * 1953-07-27 1957-04-30 Geigy Chem Corp Rust preventive compositions containing monoamidocarboxylic acids
US2939842A (en) * 1957-12-30 1960-06-07 Universal Oil Prod Co Corrosion inhibitor
US2976179A (en) * 1954-08-23 1961-03-21 Exxon Research Engineering Co Rust preventives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2330524A (en) * 1941-06-16 1943-09-28 Alox Corp Corrosion inhibitor
US2433243A (en) * 1946-05-21 1947-12-23 Gulf Oil Corp Diesel fuel oils
US2736658A (en) * 1952-07-23 1956-02-28 Armour & Co Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2790779A (en) * 1953-07-27 1957-04-30 Geigy Chem Corp Rust preventive compositions containing monoamidocarboxylic acids
US2976179A (en) * 1954-08-23 1961-03-21 Exxon Research Engineering Co Rust preventives
US2939842A (en) * 1957-12-30 1960-06-07 Universal Oil Prod Co Corrosion inhibitor

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4478604A (en) * 1982-04-01 1984-10-23 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof
US4640787A (en) * 1982-04-01 1987-02-03 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof
US4496368A (en) * 1983-06-17 1985-01-29 Texaco Inc. Isopropylidene malonate-N-alkyl alkylenediamine condensation products
US5312459A (en) * 1989-07-25 1994-05-17 Sprugel Friedrich A Additive for liquefied-gas fuels
US5300235A (en) * 1991-02-08 1994-04-05 Exxon Chemical Patents Inc. Corrosion inhibitors
US5322630A (en) * 1992-05-14 1994-06-21 Exxon Chemical Patents Inc. Amine derivatives as corrosion inhibitors
WO1996038518A1 (en) * 1995-05-30 1996-12-05 Ashland Inc. Additive system for fuel oil
EP1739154A2 (de) 2005-06-27 2007-01-03 Afton Chemical Corporation Schmierfähigkeitsadditiv für Kraftstoffe
US20060288638A1 (en) * 2005-06-27 2006-12-28 Schwab Scott D Lubricity additive for fuels
EP1739154A3 (de) * 2005-06-27 2008-07-16 Afton Chemical Corporation Schmierfähigkeitsadditiv für Kraftstoffe
CN1891799B (zh) * 2005-06-27 2011-04-20 雅富顿公司 燃料用润滑添加剂
US8287608B2 (en) 2005-06-27 2012-10-16 Afton Chemical Corporation Lubricity additive for fuels
US20080060608A1 (en) * 2006-09-07 2008-03-13 Angela Priscilla Breakspear Method and use for the prevention of fuel injector deposits
US20090056203A1 (en) * 2007-08-29 2009-03-05 Baker Hughes Incorporated Branched carboxylic acids as fuel lubricity additives
US7867295B2 (en) * 2007-08-29 2011-01-11 Baker Hughes Incorporated Branched carboxylic acids as fuel lubricity additives
US20110061292A1 (en) * 2009-09-14 2011-03-17 Baker Hughes Incorporation No-Sulfur Fuel Lubricity Additive
US8262749B2 (en) 2009-09-14 2012-09-11 Baker Hughes Incorporated No-sulfur fuel lubricity additive
US8425628B2 (en) 2009-09-14 2013-04-23 Baker Hughes Incorporated No-sulfur fuel lubricity additive

Also Published As

Publication number Publication date
NO119452B (de) 1970-05-19
BE704841A (de) 1968-04-09
DE1645746A1 (de) 1970-01-02
NL6713367A (de) 1968-04-08
SE305500B (de) 1968-10-28
CH503100A (de) 1971-02-15
GB1183399A (en) 1970-03-04
AT286477B (de) 1970-12-10

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