EP0191952A1 - Sels d'acides alcénylsuccinamiques, procédé pour leur préparation et leur utilisation comme inhibiteurs de corrosion - Google Patents

Sels d'acides alcénylsuccinamiques, procédé pour leur préparation et leur utilisation comme inhibiteurs de corrosion Download PDF

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Publication number
EP0191952A1
EP0191952A1 EP85116667A EP85116667A EP0191952A1 EP 0191952 A1 EP0191952 A1 EP 0191952A1 EP 85116667 A EP85116667 A EP 85116667A EP 85116667 A EP85116667 A EP 85116667A EP 0191952 A1 EP0191952 A1 EP 0191952A1
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EP
European Patent Office
Prior art keywords
formula
mol
salts
alkenyl
amidamine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
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EP85116667A
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German (de)
English (en)
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EP0191952B1 (fr
Inventor
Werner Dr. Ritschel
Hermann Dr. Hoffmann
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Hoechst AG
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Hoechst AG
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Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0191952A1 publication Critical patent/EP0191952A1/fr
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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
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/145—Amides; N-substituted amides

Definitions

  • succinic acid derivatives are already known as anti-corrosion agents.
  • alkyl or alkenylsuccinic acid half esters are described in US Pat. No. 4,053,426, which are used in the form of the amine salts for lubricants and aqueous metalworking fluids.
  • US Patent 4,235,874 describes alkenyl succinic acid or anhydride and triesters of triethanolamine as corrosion inhibitors for refined petroleum products.
  • US Pat. No. 4,148,605 Ester dicarboxylic acids described, which are obtained by reacting alkenyl succinic anhydride with hydroxy carboxylic acids.
  • succinic acid half-amides are also known: for example, US Pat. No. 2,490,744 lists reaction products of alkenylsuccinic anhydrides with primary amines in a molar ratio of 1.25 to 2: 1 as rust inhibitors in lubricating oils, the total number of carbon atoms in the reaction product being between 28 and 50 should be.
  • German Offenlegungsschrift 3,300,874 alkanolamine salts of alkenylsuccinic acid half-amides are described as corrosion inhibitors for aqueous systems; these compounds are prepared by reacting alkenylsuccinic anhydrides with primary CI - Cl0 amines and subsequent neutralization with C 2 -C 4 alkanolamines.
  • Further alkenylsuccinic acid halamides and their use as corrosion protection agents are known from German Offenlegungsschriften 3 319 183 and 3 341 013.
  • the use of succinic acid halamides as corrosion inhibitors in petroleum production and processing is not yet known.
  • the invention relates to salts of alkenylsuccinic acid halamides of the formulas
  • R 1 is C 6 -C 100 , preferably C 9 -C 22 alkenyl
  • A is the protonated residue of an amidamine of the formula II
  • R 2 is C 5 -C 22 -, preferably C 10 -C 18 alkyl, C 5 -C 22 -, preferably g s-wise C 10 -C 18 alkenyl or cycloalkyl
  • R 3 is a group of the formula - (CH2CHO) H
  • Y is hydrogen or methyl
  • n is a number from 0 to 12
  • x is a number from 1 to 3 mean.
  • Cycloalkyl under R 2 preferably means those groups which are derived from the naphthenic acids.
  • the salts of the formulas Ia and Ib are prepared by first reacting an alkenyl succinic anhydride with excess ammonia, giving the ammonium salts.
  • the reaction can be carried out in an inert organic solvent such as petroleum ether or toluene with gaseous ammonia, the ammonium salt crystallizing out; however, the reaction can just as well be carried out with aqueous ammonia, the ammonium salt being obtained in the form of an aqueous solution.
  • the salts according to the invention are then prepared from these alkenylsuccinic acid half-amide ammonium salts by heating in aqueous solution at about 100 ° C. with an amidamine of the formula II, ammonia escaping.
  • the amidamines are prepared by amidation at about 150 to 160 ° C. of carboxylic acids with amines such as diethylene triamine, triethylene tetramine or tetraethylene pentamine and optionally subsequent oxyalkylation with ethylene oxide or propylene oxide under customarily known reaction conditions.
  • solutions of the compounds according to the invention obtained in the synthesis can be used directly without isolation of the end product.
  • These solutions are expediently diluted with a suitable solvent, for example with a low alcohol, and adjusted to a concentration of about 30 to 50% of active substance.
  • a good corrosion protection effect is obtained by adding this commercial product in quantities of 5 to 100, preferably 10 to 50 ppm to the petroleum or petroleum products.
  • a dynamic test (so-called "wheel test”) was used to test the inhibitor compositions, a method by which the corrosion inhibitors for oil and gas production are tested.
  • Kerosene which contained salt water with 5% by weight NaCl, based on water, was used as the test medium.
  • the emulsion contained 90% by weight of salt water and was saturated with H 2 S or CO 2 .
  • the degreased and weighed sheets were then introduced into the emulsions and subjected to mechanical movement (40 rpm by means of a shaft rotating the test vessels) at 70 ° C. for 24 hours.
  • test sheet strips were then cleaned with an inhibiting acid, degreased and weighed after drying to determine the weight loss.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP85116667A 1985-01-16 1985-12-31 Sels d'acides alcénylsuccinamiques, procédé pour leur préparation et leur utilisation comme inhibiteurs de corrosion Expired EP0191952B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853501180 DE3501180A1 (de) 1985-01-16 1985-01-16 Salze von alkenylbernsteinsaeurehalbamiden, verfahren zu deren herstellung und deren verwendung als korrosionsinhibitoren
DE3501180 1985-01-16

Publications (2)

Publication Number Publication Date
EP0191952A1 true EP0191952A1 (fr) 1986-08-27
EP0191952B1 EP0191952B1 (fr) 1988-09-07

Family

ID=6259921

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85116667A Expired EP0191952B1 (fr) 1985-01-16 1985-12-31 Sels d'acides alcénylsuccinamiques, procédé pour leur préparation et leur utilisation comme inhibiteurs de corrosion

Country Status (4)

Country Link
US (1) US4722812A (fr)
EP (1) EP0191952B1 (fr)
JP (1) JPS61167651A (fr)
DE (2) DE3501180A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0359048A2 (fr) * 1988-09-03 1990-03-21 Hoechst Aktiengesellschaft Sels d'amidoamines des dérivés de l'acide alkénylsuccinique, leur procédé de préparation et leur utilisation comme inhibiteurs de corrosion
EP0464473A1 (fr) * 1990-06-23 1992-01-08 Hoechst Aktiengesellschaft Sels de mono-amides d'acides alcénylsucciniques et leur utilisation comme inhibiteurs de corrosion et emulsifiants pour huiles de traitement de métaux
FR2700336A1 (fr) * 1993-01-11 1994-07-13 Hoechst France Succinimides substituées, leur procédé de préparation et leur application comme inhibiteur de corrosion.
EP1359208A2 (fr) * 2002-04-23 2003-11-05 Rohm And Haas Company Produits de la réaction entre des amines et des acides comme dispersants d'asphalthènes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250225A (en) * 1991-02-04 1993-10-05 Basf Aktiengesellschaft Ammonium salt of an alkenylsuccinic half-amide and the use thereof as corrosion inhibitor in oil and/or gas production technology
US20040232042A1 (en) * 2003-05-23 2004-11-25 Ravindranath Mukkamala Amine-acid reaction products as asphaltene dispersants in crude oil

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4332737A (en) * 1980-04-18 1982-06-01 E. I. Du Pont De Nemours And Company Acid reaction products of polymeric amines
DE3300874A1 (de) * 1983-01-13 1984-07-19 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeurederivate als korrosionsschutzmittel
EP0127132A1 (fr) * 1983-05-27 1984-12-05 Hoechst Aktiengesellschaft Utilisation de monoamides d'acides alcénylsucciniques comme inhibiteurs de corrosion

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3341013A1 (de) * 1983-11-12 1985-05-23 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeure-mono-dialkylamide als wasserloesliche korrosionsschutzmittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4332737A (en) * 1980-04-18 1982-06-01 E. I. Du Pont De Nemours And Company Acid reaction products of polymeric amines
DE3300874A1 (de) * 1983-01-13 1984-07-19 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeurederivate als korrosionsschutzmittel
EP0127132A1 (fr) * 1983-05-27 1984-12-05 Hoechst Aktiengesellschaft Utilisation de monoamides d'acides alcénylsucciniques comme inhibiteurs de corrosion

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0359048A2 (fr) * 1988-09-03 1990-03-21 Hoechst Aktiengesellschaft Sels d'amidoamines des dérivés de l'acide alkénylsuccinique, leur procédé de préparation et leur utilisation comme inhibiteurs de corrosion
EP0359048A3 (fr) * 1988-09-03 1991-10-23 Hoechst Aktiengesellschaft Sels d'amidoamines des dérivés de l'acide alkénylsuccinique, leur procédé de préparation et leur utilisation comme inhibiteurs de corrosion
EP0464473A1 (fr) * 1990-06-23 1992-01-08 Hoechst Aktiengesellschaft Sels de mono-amides d'acides alcénylsucciniques et leur utilisation comme inhibiteurs de corrosion et emulsifiants pour huiles de traitement de métaux
FR2700336A1 (fr) * 1993-01-11 1994-07-13 Hoechst France Succinimides substituées, leur procédé de préparation et leur application comme inhibiteur de corrosion.
EP0606795A1 (fr) * 1993-01-11 1994-07-20 Societe Francaise Hoechst Succinimides substituées, leur procédé de préparation et leur application comme inhibiteur de corrosion
US5382667A (en) * 1993-01-11 1995-01-17 Societe Francaise Hoechst Substituted succinimides as corrosion inhibitors
EP1359208A2 (fr) * 2002-04-23 2003-11-05 Rohm And Haas Company Produits de la réaction entre des amines et des acides comme dispersants d'asphalthènes
EP1359208A3 (fr) * 2002-04-23 2004-11-03 Rohm And Haas Company Produits de la réaction entre des amines et des acides comme dispersants d'asphalthènes

Also Published As

Publication number Publication date
US4722812A (en) 1988-02-02
EP0191952B1 (fr) 1988-09-07
DE3564805D1 (en) 1988-10-13
JPS61167651A (ja) 1986-07-29
DE3501180A1 (de) 1986-07-17

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