EP0191952B1 - 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
EP0191952B1
EP0191952B1 EP85116667A EP85116667A EP0191952B1 EP 0191952 B1 EP0191952 B1 EP 0191952B1 EP 85116667 A EP85116667 A EP 85116667A EP 85116667 A EP85116667 A EP 85116667A EP 0191952 B1 EP0191952 B1 EP 0191952B1
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EP
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Prior art keywords
mol
formula
salts
alkenyl
corrosion inhibitors
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EP85116667A
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German (de)
English (en)
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EP0191952A1 (fr
Inventor
Werner Dr. Ritschel
Hermann Dr. Hoffmann
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Hoechst AG
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Hoechst AG
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    • 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 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 said to be between 28 and 50 .
  • 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 C 1 -C 10 amines and subsequent neutralization with C 2 -C 4 alkanolamines.
  • Further alkenylsuccinic acid halamides and their use as anti-corrosion agents are known from German Offenlegungsschriften 3319183 and 3341 013.
  • the use of succinic acid halamides as corrosion inhibitors in petroleum production and processing is not yet known.
  • rust inhibitors which are obtained by reacting dicarboxylic acids with acylated polyalkylene polyamines.
  • these products are not salts of dicarboxylic acids and polyalkylene polyamines, but the dicarboxylic acid is bound here to the amino group solely by acylation.
  • the invention relates to salts of alkenylsuccinic acid halamides of the formulas where 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 C S -C 22 -, preferably C 10 -C 18 alkyl, C 5 -C 22 -, preferably C 10 -C 18 alkenyl or cycloalkyl, R 3 is a group of the formula R 4 is either a group of the formula -COR 2 and simultaneously R 5 is hydrogen or R 4 and R 5 are simultaneously the same as R 3 , Y is hydrogen or methyl, n is a number from 0 to 12 and 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 alkenylsuccinic 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.
  • R alkyl chain of tallow fatty acid and proceeds as described in the general instructions. After the end of the reaction, 848 g of isobutanol are added and a yellow solution with an active substance content of 50% is obtained.
  • R alkyl skeleton of naphthenic acid and proceeds as described in the general instructions. Finally, put 1 060 g Methanol, whereupon one contains a brown solution which contains 50% of the active substance.
  • a dynamic test (so-called “wheel test”) was used to test the inhibitor compositions, a method with 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 a mechanical movement (40 rpm by means of a shaft rotating the test vessels) at 70 ° C. for 24 hours. subjected.
  • test sheet strips were then cleaned with an inhibiting acid, degreased and weighed after drying to determine the weight loss.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Claims (3)

1. Sels d'acides alcényl-succinamiques répondant à l'une des formules : (Voir formules page 9)
Figure imgb0021
dans lesquelles R' représente un alcényle en C6-C100, de préférence en C9-C22, et A représente le radical protoné d'une amide-amine répondant à la formule Il :
Figure imgb0022
dans laquelle R2 représente un alkyle en C5-C22, de préférence en C10-C18, un alcényle en C5-C22, de préférence en C10-C18, ou un cycloalkyle, R3 représente un radical
Figure imgb0023
R4 représente un radical -COR2 et, en même temps, R5 représente l'hydrogène, ou R4 et R5 ont chacun, en même temps, la même signification que R3, Y représente l'hydrogène ou un méthyle, n désigne un nombre de 0 à 12 et x désigne un nombre de 1 à 3.
2. Procédé pour préparer les composés définis à la revendication 1, procédé caractérisé en ce qu'on fait réagir un anhydride alcényl-succinique de formule :
Figure imgb0024
avec l'ammoniac, puis on fait réagir les alcényl-succinates d'ammonium ainsi obtenus avec une amide-amine de formule :
Figure imgb0025
3. Application des composés selon la revendication 1 comme inhibiteurs de corrosion dans des émulsions HL (« eau-dans-l'huile »).
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 EP0191952A1 (fr) 1986-08-27
EP0191952B1 true EP0191952B1 (fr) 1988-09-07

Family

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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)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3830068A1 (de) * 1988-09-03 1990-04-05 Hoechst Ag Amidoamin-salze von alkenylbernsteinsaeurederivaten, verfahren zu deren herstellung und deren verwendung als korrosionsinhibitoren
DE59102414D1 (de) * 1990-06-23 1994-09-08 Hoechst Ag Salze von Alkenylbernsteinsäurehalbamiden und deren Verwendung als Korrosionsschutzmittel und Emulgatoren für Metallbearbeitungsöle.
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
FR2700336B1 (fr) * 1993-01-11 1995-04-14 Hoechst France Succinimides substituées, leur procédé de préparation et leur application comme inhibiteur de corrosion.
CA2424903A1 (fr) * 2002-04-23 2003-10-23 Rohm And Haas Company Produits de reaction entre une amine et un acide utilises comme dispersants d'asphaltenes dans du petrole brut
US20040232042A1 (en) * 2003-05-23 2004-11-25 Ravindranath Mukkamala Amine-acid reaction products as asphaltene dispersants in crude oil

Family Cites Families (4)

* 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
DE3319183A1 (de) * 1983-05-27 1984-11-29 Hoechst Ag, 6230 Frankfurt Verwendung von alkenylbernsteinsaeurehalbamiden als korrosionsschutzmittel
DE3341013A1 (de) * 1983-11-12 1985-05-23 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeure-mono-dialkylamide als wasserloesliche korrosionsschutzmittel

Also Published As

Publication number Publication date
EP0191952A1 (fr) 1986-08-27
DE3501180A1 (de) 1986-07-17
US4722812A (en) 1988-02-02
JPS61167651A (ja) 1986-07-29
DE3564805D1 (en) 1988-10-13

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