US20090057618A1 - Corrosion inhibitors containing amphoteric surfactants - Google Patents

Corrosion inhibitors containing amphoteric surfactants Download PDF

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Publication number
US20090057618A1
US20090057618A1 US12/231,243 US23124308A US2009057618A1 US 20090057618 A1 US20090057618 A1 US 20090057618A1 US 23124308 A US23124308 A US 23124308A US 2009057618 A1 US2009057618 A1 US 2009057618A1
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US
United States
Prior art keywords
alkyl
metal
metal salt
amphoteric surfactant
corrosion inhibitors
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.)
Abandoned
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US12/231,243
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English (en)
Inventor
Dirk Leinweber
Michael Feustel
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Clariant Finance BVI Ltd
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Clariant International Ltd
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Filing date
Publication date
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Assigned to CLARIANT INTERNATIONAL LTD. reassignment CLARIANT INTERNATIONAL LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FEUSTEL, MICHAEL, LEINWEBER, DIRK
Publication of US20090057618A1 publication Critical patent/US20090057618A1/en
Assigned to CLARIANT FINANCE (BVI) LTD. reassignment CLARIANT FINANCE (BVI) LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CLARIANT INTERNATIONAL LTD.
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C23F11/16—Sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0073—Anticorrosion compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/145—Amides; N-substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3472—Organic compounds containing sulfur additionally containing -COOH groups or derivatives thereof

Definitions

  • the present invention relates to a process for corrosion inhibition on and in apparatuses for conveying and transporting hydrocarbons in oil production and processing by adding a metal salt of N-acylmethionine and an amphoteric surfactant to the corrosive system.
  • amides, amidoamines or imidazolines of fatty acids and polyamines have an extremely good oil solubility and, owing to poor partitioning, are therefore present only in low concentration in the corrosive water phase. Accordingly, these products must be used at a high dose in spite of their poor biodegradability.
  • Quaternary alkylammonium compounds are alternative corrosion inhibitors of the prior art, which also have biostatic properties in addition to the corrosion-inhibiting properties.
  • the quats have a substantially reduced film persistence, for example compared with the imidazolines, and therefore likewise lead to effective corrosion protection only in relatively high doses.
  • the strong algae toxicity and the moderate biodegradability are increasingly limiting the use of quats to ecologically insensitive fields of use.
  • JP-A-8 337 562 and JP-A-8 337 563 describe N-acylamino acids and their alkali metal salts, which can also be used as corrosion inhibitors.
  • JP-A-49 026 145 describes alkali metal salts of N-acylamino acids, which salts can be used as corrosion inhibitors.
  • N-Lauroylglycine sodium salt is mentioned as an example.
  • metal salts of N-acylmethionine as a mixture with amphoteric surfactants have an excellent effect as corrosion inhibitors and show good biodegradability and reduced toxicity. Owing to a synergistic effect between the metal salt of N-acylmethionine and nonionic surfactant, the dosages can be substantially reduced in comparison with the prior art, with the result that the novel corrosion inhibitor mixtures are also advantageous economically.
  • the invention therefore relates to the use of compositions containing metal salts of compounds of the formula (1)
  • R 1 is C 1 - to C 29 -alkyl, C 2 - to C 29 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, and amphoteric surfactants as corrosion inhibitors.
  • the invention furthermore relates to a process for inhibiting corrosion on metal surfaces, in particular of iron-containing metals, by adding at least one metal salt of compounds of the formula (1) and an amphoteric surfactant to a corrosive system which is in contact with the metal surfaces.
  • the invention furthermore relates to compositions containing at least one metal salt of a compound of the formula (1) and at least one amphoteric surfactant.
  • the invention furthermore relates to the use of metal salts of compounds of the formula (1) together with amphoteric surfactants as metal processing compositions.
  • the compositions according to the invention also afford very good corrosion protection even under strong mechanical load, such as during grinding, cutting and drilling of metal workpieces.
  • Corrosive systems in the context of this invention are preferably liquid/liquid or liquid/gaseous multiphase systems consisting of water and hydrocarbons which contain corrosive constituents, such as salts and acids, in free and/or dissolved form.
  • the corrosive constituents may also be gaseous, such as, for example, hydrogen sulfide and carbon dioxide.
  • Hydrocarbons in the context of this invention are organic compounds which are constituents of mineral oil/natural gas, and the secondary products thereof. Hydrocarbons in the context of this invention are also readily volatile hydrocarbons, such as, for example, methane, ethane, propane and butane. For the purposes of this invention, these also include the further gaseous constituents of mineral oil/natural gas, such as, for example, hydrogen sulfide and carbon dioxide.
  • Preferred surfactants are those which, in a concentration of 0.5% by weight in water, produce a surface tension of this aqueous solution of not more than 55 mN/m, particularly preferably of not more than 50 mN/m and especially not more than 45 mN/m.
  • R 1 is C 3 - to C 23 -alkyl, C 3 - to C 23 -alkenyl, C 6 - to C 24 -aryl or C 7 - to C 25 -alkylaryl, in particular an alkyl or alkenyl group having 7 to 17 carbon atoms.
  • amphoteric surfactants are described in detail in U.S. Pat. No. 5,106,609, U.S. Pat. No. 6,169,060 and WO 9949008. Particularly suitable amphoteric (zwitterionic) surfactants correspond to the formulae (2) to (14):
  • R is an alkyl, alkenyl, hydroxyalkyl or alkylaryl group having 4 to 22 carbon atoms
  • each radical R1, independently of one another is an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms or two R1 groups are linked to one another via an —O or —NH group with ring formation
  • A is an alkylene group having 2 to 4 carbon atoms or mixtures thereof
  • x is a number from 0 to 10.
  • M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium and m and n, independently of one another, are numbers from 1 to 4.
  • Examples are C 12/14 -alkyldimethylcarboxybetaine, C 12/14 -alkylamidopropyl-N,N-dimethyl-N-carboxylmethylbetaine, stearyldimethylcarboxybetaine, behenyldimethylcarboxybetaine, oleyldi(hydroxyethyl)carboxybetaine or oleyidimethyl-3-carboxypropylbetaine.
  • Examples are sodium lauroamphoacetate, sodium lauroamphodiacetate, sodium lauroamphopropionate, sodium lauroamphodipropionate, octylaminopropionic acid, octyliminodipropionic acid, cocoaminopropionic acid and cocoiminodipropionic acid.
  • Examples are cocodimethylsulfopropylbetaine, octyldimethyldi(hydroxyethyl)sulfopropylbetaine and stearyldimethylsulfobutylbetaine.
  • Particularly preferred amine oxides of the formulae (12) and (13) are C 8 -C 18 -alkyldimethylamine oxides and C 8 -C 18 -alkoxyethyldihydroxyethylamine oxides, such as cocodimethylamine oxide, stearyldimethylamine oxide, lauryldi(hydroxylethyl)amine oxide, and myristyldimethylamine oxide.
  • Alkyl- or alkenylimidazoliniumbetaines of the formula (14) are particularly preferred with R ⁇ C 7 -C 17 -alkyl or -alkenyl.
  • Examples are coconut fatty acid (hydroxyethylimidazoline)carboxymethylbetaine, oleic acid (hydroxyethylimidazoline)carboxymethylbetaine and tall oil fatty acid (hydroxyethylimidazoline)carboxymethylbetaine.
  • compositions according to the invention can be used alone or in combination with other known corrosion inhibitors.
  • the composition according to the invention is used in an amount such that sufficient corrosion protection is obtained under the given conditions.
  • Preferred concentrations in which the compositions according to the invention are used are from 5 to 5000 ppm, preferably from 10 to 1000 ppm, in particular from 15 to 150 ppm.
  • the mixing ratio between metal salt of the compound 1 and amphoteric surfactant is preferably from 1:9 to 9:1, in particular from 3:7 to 7:3.
  • compositions according to the invention with other corrosion inhibitors of the prior art are also particularly suitable as corrosion inhibitors.
  • N-Oleoyl-DL-methionine potassium salt having an active substance content of 40%
  • N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 8 g of tall oil fatty acid (hydroxyethylimidazoline)-carboxymethylbetaine, 20 g of butylglycol and 32 g of water.
  • N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 8 g of tall oil fatty acid (hydroxyethylimidazoline)carboxymethylbetaine, 20 g of butylglycol and 32 g of water.
  • N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 2 g of tall oil fatty acid (hydroxyethylimidazoline)-carboxymethylbetaine, 20 g of butylglycol and 23 g of water.
  • the compounds according to the invention were tested as corrosion inhibitors in the Shell wheel test. Coupons of C steel (DIN 1.1203 with 15 cm 2 surface area) were immersed in a salt water/petroleum mixture (9:1, 5% strength NaCl solution adjusted to pH 3.5 with acetic acid) and exposed to this medium at a speed of 40 rpm at 70° C. for 24 hours. The inhibitor dose was 50 ppm of a 24% solution of the inhibitor. The protection values were calculated from the decrease in the mass of the coupons, based on a blank value.
  • “comparison 1” designates a commercially available residue amine quat based on dicocosalkyl dimethylammonium chloride
  • “comparison 2” a commercially available imidazoline salt based on oleic acid diethylenetriamine
  • “comparison 3” an example from DE-10 2006 002 784 (morpholinium salt of N-cocoyl-DL-methionine, corrosion inhibitor of the prior art).
  • compositions according to the invention have very good corrosion inhibition properties at a very low dose and in some cases even substantially surpass the activity of the inhibitors of the prior art.
  • example 24 shows that the synergistic effect of the metal salt of N-acylmethionine in combination with an amphoteric surfactant decreases at a ratio of >9:1 but is still present.
  • the compounds according to the invention exhibit improved biodegradability and lower toxicity compared to the comparative examples from the prior art.
US12/231,243 2007-08-31 2008-08-29 Corrosion inhibitors containing amphoteric surfactants Abandoned US20090057618A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007041217.9 2007-08-31
DE102007041217A DE102007041217B3 (de) 2007-08-31 2007-08-31 Verwendung von Zusammensetzungen als Korrosionsinhibitoren enthaltend amphotere Tenside und die Zusammensetzungen

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US20090057618A1 true US20090057618A1 (en) 2009-03-05

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US (1) US20090057618A1 (de)
EP (1) EP2031092A3 (de)
BR (1) BRPI0803371A2 (de)
DE (1) DE102007041217B3 (de)

Cited By (16)

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KR20140146150A (ko) * 2012-03-30 2014-12-24 지보당 에스아 식품 향미 화합물로서의 n-아실화된 메티오닌 유도체
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
US10836712B2 (en) 2012-03-30 2020-11-17 Givaudan S.A. Organic compounds
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
US11122826B2 (en) 2013-10-02 2021-09-21 Givaudan Sa Organic compounds
CN114350264A (zh) * 2022-02-18 2022-04-15 河北工业大学 一种用于钴互连结构钴膜cmp粗抛的碱性抛光液及其制备方法
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties

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CN103556156A (zh) * 2013-11-20 2014-02-05 天津亿利科能源科技发展股份有限公司 一种高二氧化碳高硫化氢油田用缓蚀剂及其制备方法
US10385015B2 (en) * 2015-09-30 2019-08-20 Givaudan S.A. N-acylated methionine sulfoxides as food flavouring compounds
DE102019104019A1 (de) * 2019-02-18 2020-08-20 Johann Wolfgang Goethe-Universität Gegen Korrosion geschütztes Erzeugnis, Verfahren zur Herstellung und Verwendung einer Aminosäureverbindung zum Korrosionsschutz

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Cited By (23)

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US11524933B2 (en) 2012-03-30 2022-12-13 Givaudan Sa In or relating to organic compounds
US10913922B2 (en) 2012-03-30 2021-02-09 Givaudan S.A. N-acylated methionine derivatives as food flavoring compounds
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US11832638B2 (en) 2012-03-30 2023-12-05 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
CN104254253A (zh) * 2012-03-30 2014-12-31 奇华顿股份有限公司 作为食品加香化合物的n-酰化甲硫氨酸衍生物
KR102124224B1 (ko) 2012-03-30 2020-06-18 지보당 에스아 식품 향미 화합물로서의 n-아실화된 메티오닌 유도체
KR20140146150A (ko) * 2012-03-30 2014-12-24 지보당 에스아 식품 향미 화합물로서의 n-아실화된 메티오닌 유도체
US10836712B2 (en) 2012-03-30 2020-11-17 Givaudan S.A. Organic compounds
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
US11492326B2 (en) 2012-03-30 2022-11-08 Givaudan Sa Organic compounds
US11091429B2 (en) 2012-03-30 2021-08-17 Givaudan Sa Organic compounds
US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
US11122826B2 (en) 2013-10-02 2021-09-21 Givaudan Sa Organic compounds
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties
CN114350264A (zh) * 2022-02-18 2022-04-15 河北工业大学 一种用于钴互连结构钴膜cmp粗抛的碱性抛光液及其制备方法

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DE102007041217B3 (de) 2009-04-30
BRPI0803371A2 (pt) 2009-05-05
EP2031092A3 (de) 2011-04-13
EP2031092A2 (de) 2009-03-04

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