US20090057617A1 - Corrosion inhibitors containing anionic surfactants - Google Patents

Corrosion inhibitors containing anionic surfactants Download PDF

Info

Publication number
US20090057617A1
US20090057617A1 US12/231,231 US23123108A US2009057617A1 US 20090057617 A1 US20090057617 A1 US 20090057617A1 US 23123108 A US23123108 A US 23123108A US 2009057617 A1 US2009057617 A1 US 2009057617A1
Authority
US
United States
Prior art keywords
alkyl
formula
anionic surfactant
cation
alkenyl
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
Application number
US12/231,231
Inventor
Dirk Leinweber
Michael Feustel
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.)
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Assigned to CLARIANT INTERNATIONAL LTD. reassignment CLARIANT INTERNATIONAL LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FEUSTEL, MICHAEL, LEINWEBER, DIRK
Publication of US20090057617A1 publication Critical patent/US20090057617A1/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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23FNON-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
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • C23F11/14Nitrogen-containing compounds
    • C23F11/145Amides; N-substituted amides
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/54Compositions for in situ inhibition of corrosion in boreholes or wells
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • C11D1/10Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0073Anticorrosion compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/34Organic compounds containing sulfur
    • C11D3/349Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23FNON-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
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • C23F11/16Sulfur-containing compounds
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23FNON-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
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • C23F11/167Phosphorus-containing compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/34Organic compounds containing sulfur
    • C11D3/3472Organic 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 ionic 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 anionic 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 anionic 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)
  • 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 anionic 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 anionic surfactant.
  • the invention furthermore relates to the use of metal salts of compounds of the formula (1) together with anionic 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.
  • N-acylmethionine is effected by acylation of methionine by means of carboxylic acid chloride or carboxylic anhydride in the presence of a base (e.g. sodium hydroxide).
  • a base e.g. sodium hydroxide
  • DL-methionine is preferably used for this purpose, but the pure enantiomeric forms may likewise be used.
  • the hydroxides of alkali metals or alkaline earth metals are preferred as the base used for the preparation of the metals salts according to the invention.
  • the hydroxides of Na, K, Ca and Mg are particularly preferred.
  • the metal salts according to the invention are preferably alkali metal or alkaline earth metal salts, in particular Na, K, Ca or Mg salts, of the compounds of the formula 1.
  • the metal salts of N-acylmethionine are present in unneutralized and isolated form and are formulated directly with the anionic surfactants according to the invention to give the corrosion inhibitor mixture according to the invention.
  • the preparation process for the corrosion inhibitors according to the invention is substantially more economical.
  • the metal salts of N-acylmethionine according to the invention are obtained as a rule as 10-50% strength solutions in water and are formulated directly with one or more anionic surfactants to give the corrosion inhibitor mixture.
  • alcoholic solvents such as, for example, methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, methyl glycol, butyl glycol or butyl diglycol, may be added.
  • Suitable anionic surfactants are:
  • Suitable alkylphosphates are salts of the formula (RO) n (O ⁇ P)(OM) l , in which R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
  • R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
  • M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkyl ether phosphates are salts of the formula [RO(A) m ] n (O ⁇ P)(OM) l , in which R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
  • A is an ethoxy or propoxy unit
  • m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12.
  • M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkylphosphonates are salts of the formula (2)
  • Suitable alkylpolyalkylene glycol ether carboxylates or alkylarylpolyalkylene glycol ether carboxylates are salts of the formula RO(A) m CO 2 M, in which R is a C 4 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
  • A is an ethoxy or propoxy unit
  • m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12
  • M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylmethyltaurates are salts of the formula R(C ⁇ O)(NCH 3 )CH 2 CH 2 SO 3 M, in which R is a C 5 -C 29 -alkyl or a C 5 -C 29 -alkenyl radical, preferably a C 7 -C 17 -alkyl, or a C 7 -C 17 -alkenyl radical.
  • M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylsarcosinates are salts of the formula R(C ⁇ O)(NCH 3 )CH 2 CO 2 M, in which R is a C 5 -C 29 -alkyl or a C 5 -C 29 -alkenyl radical, preferably a C 7 -C 17 -alkyl or an C 7 -C 17 -alkenyl radical.
  • M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylglutamates are salts of the formula (3)
  • Suitable alkylsuccinates are salts of the formula (4)
  • Suitable alkylsuccinimides are salts of the formula (5)
  • 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, based on the weight of the phases to be inhibited with respect to the corrosion properties.
  • the mixing ratio between metal salt of the compound 1 and anionic surfactant is preferably from 1:9 to 9:1, in particular from 3:7 to 7:3, especially from 1:2 to 2:1.
  • compositions according to the invention with other corrosion inhibitors and/or those of the prior art are also particularly suitable as corrosion inhibitors.
  • N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 10 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate, 20 g of butylglycol and 15 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 39 shows that the synergistic effect of the metal salt of N-acylmethionine in combination with an anionic 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The invention relates to the use of compounds of the formula (1)
Figure US20090057617A1-20090305-C00001
in which R1 is C1- to C29-alkyl, C2- to C29-alkenyl, C6- to C30-aryl or C7- to C30-alkylaryl, and anionic surfactants as corrosion inhibitors.

Description

  • The present invention is described in the German priority application No. 10 2007 041 204.7 filed Aug. 31, 2007, which is hereby incorporated by reference as is fully disclosed herein.
  • 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 ionic surfactant to the corrosive system.
  • In industrial processes in which metals come into contact with water or with oil/water two-phase systems, there is the danger of corrosion. This is particularly pronounced if the aqueous phase has a high salt content, as in oil extraction and processing processors, or is acidic due to dissolved acid gases, such as carbon dioxide or hydrogen sulfide. The exploitation of a deposit and the processing of oil are therefore not possible without special additives for protecting the equipment used.
  • Although suitable corrosion inhibitors for oil production and processing have long been known, they are unacceptable in future for offshore applications for reasons relating to environmental protection.
  • As typical corrosion inhibitors of the prior art, 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 (quats) are alternative corrosion inhibitors of the prior art, which also have biostatic properties in addition to the corrosion-inhibiting properties. In spite of improved water solubility, 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.
  • U.S. Pat. No. 4,240,823 describes N-acylmethionine derivatives which are used as growth regulators in the area of crop protection.
  • 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.
  • A disadvantage of the compounds of the prior art is, however, that their activity at low doses is often not sufficient.
  • DE-10 2006 002 784 discloses N-acylmethionine ammonium salts which have an excellent effect as corrosion inhibitors and show good biodegradability and reduced toxicity. A disadvantage of these compounds is, however, their complicated preparation and the associated relatively high production costs.
  • It was an object of the present invention to provide novel corrosion inhibitors which, in combination with improved corrosion protection, also afford improved biodegradability and lower toxicity in comparison with the corrosion inhibitors of the prior art in addition to good water solubility. Furthermore, the novel corrosion inhibitors should be capable of being produced at an economically acceptable price.
  • It has now surprisingly been found that metal salts of N-acylmethionine as a mixture with anionic 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 anionic 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)
  • Figure US20090057617A1-20090305-C00002
      • in which R1 is C1- to C29-alkyl, C2- to C29-alkenyl, C6- to C30-aryl or C7- to C30-alkylaryl, and anionic 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 anionic 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 anionic surfactant.
  • The invention furthermore relates to the use of metal salts of compounds of the formula (1) together with anionic surfactants as metal processing compositions. Here, 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.
  • In a further preferred embodiment of the invention, R1 is C3- to C23-alkyl, C3- to C23-alkenyl, C6- to C24-aryl or C7- to C25-alkylaryl, in particular an alkyl or alkenyl group having 7 to 17 carbon atoms.
  • The preparation of metal salts of N-acylmethionine is effected by acylation of methionine by means of carboxylic acid chloride or carboxylic anhydride in the presence of a base (e.g. sodium hydroxide). For economic reasons, DL-methionine is preferably used for this purpose, but the pure enantiomeric forms may likewise be used. C8-18 alkyl or alkenyl chlorides, such as, for example, octanoyl chloride, decanoyl chloride, dodecanoyl chloride, coconut fatty acid chloride or oleyl chloride, are preferably used for the acylation.
  • The hydroxides of alkali metals or alkaline earth metals are preferred as the base used for the preparation of the metals salts according to the invention. The hydroxides of Na, K, Ca and Mg are particularly preferred. Accordingly, the metal salts according to the invention are preferably alkali metal or alkaline earth metal salts, in particular Na, K, Ca or Mg salts, of the compounds of the formula 1.
  • In contrast to DE-10 2006 002 784, the metal salts of N-acylmethionine are present in unneutralized and isolated form and are formulated directly with the anionic surfactants according to the invention to give the corrosion inhibitor mixture according to the invention. As a result, the preparation process for the corrosion inhibitors according to the invention is substantially more economical.
  • The metal salts of N-acylmethionine according to the invention are obtained as a rule as 10-50% strength solutions in water and are formulated directly with one or more anionic surfactants to give the corrosion inhibitor mixture. For stabilizing the aqueous formulations, alcoholic solvents, such as, for example, methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, methyl glycol, butyl glycol or butyl diglycol, may be added.
  • Suitable anionic surfactants are:
  • Alkylsulfonates, olefinsulfonates, alkylsulfates, alkylaryl ether sulfates, alkyl ether sulfates, sulfosuccinates, alkylsuccinates, alkylphosphates, alkyl ether phosphates, alkylphosphonates, alkylpolyalkylene glycol ether carboxylates, alkylarylpolyalkylene glycol ether carboxylates, fatty acid isethionates, N-acylmethyltaurates, N-acylsarcosinates, alkylbenzenesulfonates, alkylnaphthalenesulfonates, N-acylglutamates, amphoacetates, alkylsulfamidocarboxylates, alkyl- and alkenylglycerylsulfates and fatty acid-protein condensates which are obtained by reacting fatty acid chlorides with oligopeptides.
  • Preferred anionic surfactants are described in more detail below:
  • Suitable alkylphosphates are salts of the formula (RO)n(O═P)(OM)l, in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. For n and l, 0<n<3 and 0<l<3, with the proviso that n+l=3. Preferably, 1≦n≦2 and 1≦l≦2. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkyl ether phosphates are salts of the formula [RO(A)m]n(O═P)(OM)l, in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. A is an ethoxy or propoxy unit, m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12. For n and l, 0<n<3 and 0<l<3, with the proviso that n+l=3. Preferably, 1≦n≦2 and 1≦l≦2. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkylphosphonates are salts of the formula (2)
  • Figure US20090057617A1-20090305-C00003
      • in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkylpolyalkylene glycol ether carboxylates or alkylarylpolyalkylene glycol ether carboxylates are salts of the formula RO(A)mCO2M, in which R is a C4-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. A is an ethoxy or propoxy unit, m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12, and M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylmethyltaurates are salts of the formula R(C═O)(NCH3)CH2CH2SO3M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl, or a C7-C17-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylsarcosinates are salts of the formula R(C═O)(NCH3)CH2CO2M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl or an C7-C17-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable N-acylglutamates are salts of the formula (3)
  • Figure US20090057617A1-20090305-C00004
      • in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl or a C7-C17-alkenyl radical. M+ is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkylsuccinates are salts of the formula (4)
  • Figure US20090057617A1-20090305-C00005
      • in which D=CH2CHR and R is a C6-C30-alkyl or a C6-C30-alkenyl radical, preferably a C8-C18-alkyl or a C8-C18-alkenyl radical, R′ is hydrogen or a C1-C8-alkyl or a C3-C18-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Suitable alkylsuccinimides are salts of the formula (5)
  • Figure US20090057617A1-20090305-C00006
      • in which R is a C6-C30-alkyl or a C6-C30-alkenyl radical, preferably a C8-C18-alkyl or a C8-C18-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • The compositions according to the invention can be used alone or in combination with other known corrosion inhibitors. In general, 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, based on the weight of the phases to be inhibited with respect to the corrosion properties. The mixing ratio between metal salt of the compound 1 and anionic surfactant is preferably from 1:9 to 9:1, in particular from 3:7 to 7:3, especially from 1:2 to 2:1.
  • Mixtures of the compositions according to the invention with other corrosion inhibitors and/or those of the prior art are also particularly suitable as corrosion inhibitors.
  • EXAMPLES
  • General Method for the Preparation of Metal Salts of N-acylmethionine
  • In a standard stirred apparatus, 1 mol of DL-methionine in 300 ml of water are neutralized with 50% strength aqueous metal hydroxide solution. 1 mol of carboxylic acid chloride is metered into the resulting solution at 15-20° C., the pH being kept at 10-13 by simultaneous metering of 15% strength aqueous metal hydroxide solution. The reaction solution is stirred for a further 3 h at room temperature. The resulting metal salt of N-acylmethionine is characterized by means of the alkali number (AN) and active substance content. Stated percentages are percentages by weight, based on the weight of the salt according to the invention.
  • Example 1 N-Cocoyl-DL-methionine Sodium Salt (Comparison)
  • N-Cocoyl-DL-methionine sodium salt having an active substance content of 40% and an AN=65 mg KOH/g was obtained from coconut fatty acid chloride, DL-methionine and sodium hydroxide.
  • Example 2 N-Oleoyl-DL-methionine potassium Salt (Comparison)
  • N-Oleoyl-DL-methionine potassium salt having an active substance content of 40% and an AN=56 mg KOH/g was obtained from oleoyl chloride, DL-methionine and potassium hydroxide.
  • Example 3 Corrosion Inhibitor Mixture 1
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium di(2-ethylhexyl)phosphate and 20 g of butylglycol.
  • Example 4 Corrosion Inhibitor Mixture 2
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium bis(lauryltetraethoxy)phosphate and 20 g of butylglycol.
  • Example 5 Corrosion Inhibitor Mixture 3
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium octylphosphonate and 20 g of butylglycol.
  • Example 6 Corrosion Inhibitor Mixture 4
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of (oleyl alcohol+10 EO)-ether carboxylic acid sodium salt and 20 g of butylglycol.
  • Example 7 Corrosion Inhibitor Mixture 5
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength dispersion of coconut fatty acid methyltaurate sodium salt and 20 g of butylglycol.
  • Example 8 Corrosion Inhibitor Mixture 6
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium lauroyl sarcosinate and 20 g of butylglycol.
  • Example 9 Corrosion Inhibitor Mixture 7
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium N-cocoylglutamate and 20 g of butylglycol.
  • Example 10 Corrosion Inhibitor Mixture 8
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of potassium monoisopropyl octenylsuccinate and 20 g of butylglycol.
  • Example 11 Corrosion Inhibitor Mixture 9
  • 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate and 20 g of butylglycol.
  • Example 12 Corrosion Inhibitor Mixture 10
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium di(2-ethylhexyl)phosphate and 20 g of butylglycol.
  • Example 13 Corrosion Inhibitor Mixture 11
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium bis(lauryltetraethoxy)phosphate and 20 g of butylglycol.
  • Example 14 Corrosion Inhibitor Mixture 12
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium octylphosphonate and 20 g of butylglycol.
  • Example 15 Corrosion Inhibitor Mixture 13
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of (oleyl alcohol+10 EO)-ethercarboxylic acid sodium salt and 20 g of butylglycol.
  • Example 16 Corrosion Inhibitor Mixture 14
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength dispersion of coconut fatty acid methyltaurate sodium salt and 20 g of butylglycol.
  • Example 17 Corrosion Inhibitor Mixture 15
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium lauroyl sarcosinate and 20 g of butylglycol.
  • Example 18 Corrosion Inhibitor Mixture 16
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium N-cocoylglutamate and 20 g of butylglycol.
  • Example 19 Corrosion Inhibitor Mixture 17
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of potassium monoisopropyl octenylsuccinate and 20 g of butylglycol.
  • Example 20 Corrosion Inhibitor Mixture 18
  • 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate and 20 g of butylglycol.
  • Example 21 Corrosion Inhibitor Mixture 19
  • 55 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 10 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate, 20 g of butylglycol and 15 g of water.
  • Activity of the compounds according to the invention as corrosion inhibitors
  • 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 cm2 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.
  • In the following tables, “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 and “comparison 3” an example from DE-10 2006 002 784 (morpholinium salt of N-cocoyl-DL-methionine, corrosion inhibitor of the prior art).
  • TABLE 1
    (Shell wheel test)
    Example Corrosion inhibitor ø protection %
    Comparison 1 Standard quat 28
    Comparison 2 Oleic acid DETA imidazoline 70
    Comparison 3 Morpholinium salt of N-cocoyl-DL- 75
    methionine
    Comparison 4 from example 1 67
    Comparison 5 from example 2 69
    21 from example 3 77
    22 from example 4 79
    23 from example 5 86
    24 from example 6 88
    25 from example 7 81
    26 from example 8 88
    27 from example 9 90
    28 from example 10 80
    29 from example 11 91
    30 from example 12 76
    31 from example 13 76
    32 from example 14 84
    33 from example 15 85
    34 from example 16 76
    35 from example 17 82
    36 from example 18 87
    37 from example 19 78
    38 from example 20 92
    39 from example 21 81
  • As is evident from table 1, the 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.
  • In comparison with example 29, example 39 shows that the synergistic effect of the metal salt of N-acylmethionine in combination with an anionic surfactant decreases at a ratio of >9:1 but is still present.
  • TABLE 2
    Biodegradability (OECD 306) and toxicity (EC50 Skeletonema
    Costatum) of selected corrosion inhibitors according to the
    invention
    Biodegradability Toxicity
    Example Corrosion inhibitor [%] EC50 [mg/l]
    Comparison 1 Standard quat 15.2 0.57
    Comparison 2 Oleic acid DETA 6.8 0.33
    imidazoline
    39 from example 6 93.0 80.5
    40 from example 9 95.3 65.3
    41 from example 10 86.9 120.5
    42 from example 15 90.5 105.9
    43 from example 18 92.1 91.4
    44 from example 19 85.4 150.2
  • As can clearly be seen from table 4, the compounds according to the invention exhibit improved biodegradability and lower toxicity compared to the comparative examples from the prior art.

Claims (18)

1. A method for inhibiting corrosion on a metal surface, said method comprising contacting said metal surface with a composition comprising a metal salt of the compound of the formula (1)
Figure US20090057617A1-20090305-C00007
in which R1 is C1- to C29-alkyl, C2- to C29-alkenyl, C6- to C30-aryl or C7- to C30-akylaryl, and an anionic surfactant.
2. The method of claim 1, wherein R1 is an alkyl or alkenyl group having 7 to 17 carbon atoms.
3. The method of claim 1, wherein the metal salt is an alkali metal salt.
4. The method of claim 1, wherein the anionic surfactant is an alkylphosphate which carries an alkyl group having 6 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms.
5. The method of claim 1, wherein the anionic surfactant is an alkyl ether phosphate which carries an alkyl group having 6 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms.
6. The method of claim 1, wherein the anionic surfactant is an alkylphosphonate of the formula (2)
Figure US20090057617A1-20090305-C00008
in which R is a C6- to C30-alkyl radical or a C7- to C30-alkylaryl radical and M is a cation.
7. The method of claim 1, wherein the anionic surfactant is an alkylpolyalkylene glycol ether carboxylate or alkylarylpolyalkylene glycol ether carboxylate of the formula RO(A)mCO2M, in which R is a C4-C30-alkyl or a C7-C30-alkylaryl radical, A is an ethoxy or propoxy unit, m is a number greater than 0 and M is a cation.
8. The method of claim 1, wherein the anionic surfactant is an N-acylmethyltaurate of the formula R(C═O)(NCH3)CH2CH2SO3M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical and M is a cation.
9. The method of claim 1, the anionic surfactant is an N-acylsarcosinate of the formula R(C═O)(NCH3)CH2CO2M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical and M is a cation.
10. The method of claim 1, wherein the anionic surfactant is an N-acylglutamate of the formula (3)
Figure US20090057617A1-20090305-C00009
in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical and M is a cation.
11. The method of claim 1, wherein the anionic surfactant is an alkylsuccinate of the formula (4)
Figure US20090057617A1-20090305-C00010
in which D is —CH2CHR—, R is a C6-C30-alkyl or a C6-C30-alkenyl radical, R′ is hydrogen or a C1-C18-alkyl or a C3-C18-alkenyl radical and M is a cation.
12. The method of claim 1, the anionic surfactant is an alkylsuccinimide of the formula (5)
Figure US20090057617A1-20090305-C00011
in which R is a C6-C30-alkyl or a C6-C30-alkenyl radical and M is a cation.
13. The method of claim 1, wherein a total amount of metal salt to nonionic surfactant is from 5 to 5000 ppm.
14. The method of claim 1, wherein a weight ratio of metal salt to nonionic surfactant is from 1:9 to 9:1.
15. The method of claim 1, wherein said composition further comprises a hydrocarbon and said metal surface is an apparatus for conveying and transporting the hydrocarbon.
16. The method of claim 1, wherein the composition further comprises a metal processing composition.
17. A composition containing at least one metal salt of a compound of the formula (1)
Figure US20090057617A1-20090305-C00012
in which R1 is C1- to C29-alkyl, C2- to C29-alkenyl, C6- to C30-aryl or C7- to C30-alklaryl, and at least one anionic surfactant.
18. The composition as claimed in claim 17, wherein a weight ratio of metal salt to nonionic surfactant is from 9:1 to 1:9.
US12/231,231 2007-08-31 2008-08-29 Corrosion inhibitors containing anionic surfactants Abandoned US20090057617A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007041204A DE102007041204B3 (en) 2007-08-31 2007-08-31 Use of composition as corrosion inhibitors containing anionic surfactants and the compositions
DE102007041204.7 2007-08-31

Publications (1)

Publication Number Publication Date
US20090057617A1 true US20090057617A1 (en) 2009-03-05

Family

ID=40032614

Family Applications (1)

Application Number Title Priority Date Filing Date
US12/231,231 Abandoned US20090057617A1 (en) 2007-08-31 2008-08-29 Corrosion inhibitors containing anionic surfactants

Country Status (4)

Country Link
US (1) US20090057617A1 (en)
EP (1) EP2031094A3 (en)
BR (1) BRPI0803881A2 (en)
DE (1) DE102007041204B3 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120292022A1 (en) * 2010-11-22 2012-11-22 E. I. Du Pont De Nemours And Company Composition for improving oil recovery including n-lauroyl amino acid-based compounds and microbes
US11760920B1 (en) 2022-04-06 2023-09-19 Halliburton Energy Services, Inc. Lubricant for monovalent and divalent brines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109943312B (en) * 2019-03-19 2021-03-09 中国海洋石油集团有限公司 Oil displacement agent and preparation method thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2426496A (en) * 1944-03-21 1947-08-26 Shell Dev Corrosion protecting compositions
US2991244A (en) * 1957-12-31 1961-07-04 Exxon Research Engineering Co Lubricating compositions containing phosphonic acid salts
US3903005A (en) * 1973-11-05 1975-09-02 Texaco Inc Corrosion inhibited compositions
US5178786A (en) * 1989-08-04 1993-01-12 The Lubrizol Corporation Corrosion-inhibiting compositions and functional fluids containing same
US5233087A (en) * 1989-05-22 1993-08-03 The Procter & Gamble Company Process for making alkyl ethoxy carboxylates
US6117364A (en) * 1999-05-27 2000-09-12 Nalco/Exxon Energy Chemicals, L.P. Acid corrosion inhibitor
US6150425A (en) * 1997-07-17 2000-11-21 Shiseido Company, Ltd. O/W/O type multiphase emulsion

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5014651B1 (en) * 1969-12-30 1975-05-29
JPS5648585B2 (en) 1972-07-05 1981-11-17
JPS5343377B2 (en) * 1975-03-19 1978-11-18
FR2345077A1 (en) 1976-03-24 1977-10-21 Philagro Sa NEW REGULATORY COMPOSITIONS OF PLANT GROWTH BASED ON N-ACYL METHIONINE DERIVATIVES
JPS546039A (en) * 1977-06-17 1979-01-17 Ajinomoto Co Inc Additive for polyolefin and composition
JPS5835264B2 (en) * 1978-09-30 1983-08-01 出光興産株式会社 Volatile rust inhibitor
ES2134944T3 (en) * 1993-05-08 1999-10-16 Henkel Kgaa SILVER ANTICORROSIVE AGENT II.
US5531934A (en) * 1994-09-12 1996-07-02 Rohm & Haas Company Method of inhibiting corrosion in aqueous systems using poly(amino acids)
JPH08337562A (en) 1995-04-11 1996-12-24 Kashima Sekiyu Kk N-acylamino acid compound
JPH08337563A (en) 1995-04-11 1996-12-24 Kashima Sekiyu Kk N-acylamino acid and its salt
JPH0940624A (en) * 1995-05-23 1997-02-10 Kao Corp Production of n-long chain acylamino acid or its salt
US5776875A (en) * 1996-07-16 1998-07-07 Nalco Chemical Company Use of biodegradable polymers in preventing scale build-up
BR9713464A (en) * 1996-08-30 2000-05-23 Solutia Inc New water-soluble metal machining fluids.
GB9810869D0 (en) * 1998-05-20 1998-07-22 Ass Octel Biodegradable corrosion inhibitors
JP4422226B2 (en) * 1998-12-11 2010-02-24 株式会社Adeka Amino acid derivative type lubricant
DE19930683B4 (en) * 1999-07-02 2005-02-10 Clariant Gmbh Corrosion inhibitors with improved water solubility
JP2005187828A (en) * 2003-12-24 2005-07-14 Sumitomo Chemical Co Ltd Method for preventing corrosion in facility for treating waste water containing organic sulfur compound
DE102006002784B4 (en) 2006-01-20 2007-11-29 Clariant International Limited Use of sulfur amide compound and an amine compound, as corrosion inhibitors on and in the preparation and transport of hydrocarbons in the preparation and processing of petroleum, and in metal processing auxiliary agent

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2426496A (en) * 1944-03-21 1947-08-26 Shell Dev Corrosion protecting compositions
US2991244A (en) * 1957-12-31 1961-07-04 Exxon Research Engineering Co Lubricating compositions containing phosphonic acid salts
US3903005A (en) * 1973-11-05 1975-09-02 Texaco Inc Corrosion inhibited compositions
US5233087A (en) * 1989-05-22 1993-08-03 The Procter & Gamble Company Process for making alkyl ethoxy carboxylates
US5178786A (en) * 1989-08-04 1993-01-12 The Lubrizol Corporation Corrosion-inhibiting compositions and functional fluids containing same
US6150425A (en) * 1997-07-17 2000-11-21 Shiseido Company, Ltd. O/W/O type multiphase emulsion
US6117364A (en) * 1999-05-27 2000-09-12 Nalco/Exxon Energy Chemicals, L.P. Acid corrosion inhibitor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120292022A1 (en) * 2010-11-22 2012-11-22 E. I. Du Pont De Nemours And Company Composition for improving oil recovery including n-lauroyl amino acid-based compounds and microbes
US11760920B1 (en) 2022-04-06 2023-09-19 Halliburton Energy Services, Inc. Lubricant for monovalent and divalent brines

Also Published As

Publication number Publication date
EP2031094A3 (en) 2011-04-20
DE102007041204B3 (en) 2009-04-30
EP2031094A2 (en) 2009-03-04
BRPI0803881A2 (en) 2009-06-30

Similar Documents

Publication Publication Date Title
US20090057618A1 (en) Corrosion inhibitors containing amphoteric surfactants
US20100234592A1 (en) Corrosion Inhibitors Having Increased Biodegradability and Reduced Toxicity
US7615102B2 (en) Corrosion and gas hydrate inhibitors with an increased biological degradability and a reduced toxicity
EP0526251B1 (en) Corrosion inhibitors
US8105988B2 (en) Corrosion inhibitors for a fluid
US8833450B2 (en) Nitrogen containing compounds as corrosion inhibitors
US9228089B2 (en) Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors
US20100219379A1 (en) Corrosion inhibitors containing amide surfactants for a fluid
US7435845B2 (en) Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US9103039B2 (en) Quaternary ammonium corrosion inhibitor
US6261346B1 (en) Method for protecting metal surfaces against corrosion in liquid or gaseous media
US20090057616A1 (en) Corrosion inhibitors containing cationic surfactants
US11459498B2 (en) Alkyl lactone-derived corrosion inhibitors
US5853619A (en) Low toxic corrosion inhibitor
US6372918B1 (en) Compound for inhibiting corrosion
US20090057617A1 (en) Corrosion inhibitors containing anionic surfactants
US7160507B2 (en) Corrosion inhibitors with improved water solubility and improved film persistence
EP0520761B1 (en) Amine adducts as corrosion inhibitors
US4238349A (en) Method and a composition for inhibiting corrosion
US8105987B2 (en) Corrosion inhibitors for an aqueous medium
US20090057615A1 (en) Corrosion inhibitors containing nonionic surfactants
US7008561B2 (en) Ether carboxylic acids based on alkoxylated mercaptobenzothiazoles and use of the same as corrosion inhibitors
US5530131A (en) N-alkyl-n&#39;-poly(oxyalkyl)-hexahydropyrimidines
ES2384421T3 (en) Corrosion inhibitors with increased biological degradability and reduced toxicity
US20100283011A1 (en) Corrosion Inhibitors Having Increased Biological Degradability And Minimized Toxicity

Legal Events

Date Code Title Description
AS Assignment

Owner name: CLARIANT INTERNATIONAL LTD., SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LEINWEBER, DIRK;FEUSTEL, MICHAEL;REEL/FRAME:021519/0287

Effective date: 20080811

AS Assignment

Owner name: CLARIANT FINANCE (BVI) LTD., VIRGIN ISLANDS, BRITI

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CLARIANT INTERNATIONAL LTD.;REEL/FRAME:022429/0222

Effective date: 20090313

Owner name: CLARIANT FINANCE (BVI) LTD.,VIRGIN ISLANDS, BRITIS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CLARIANT INTERNATIONAL LTD.;REEL/FRAME:022429/0222

Effective date: 20090313

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION