WO2022172279A1 - Composé dioléyle inhibant la corrosion, et formulation d'amine de celui-ci formant un film inhibant la corrosion - Google Patents

Composé dioléyle inhibant la corrosion, et formulation d'amine de celui-ci formant un film inhibant la corrosion Download PDF

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Publication number
WO2022172279A1
WO2022172279A1 PCT/IN2021/050346 IN2021050346W WO2022172279A1 WO 2022172279 A1 WO2022172279 A1 WO 2022172279A1 IN 2021050346 W IN2021050346 W IN 2021050346W WO 2022172279 A1 WO2022172279 A1 WO 2022172279A1
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WO
WIPO (PCT)
Prior art keywords
corrosion inhibiting
compound
dioleyl
corrosion
amine
Prior art date
Application number
PCT/IN2021/050346
Other languages
English (en)
Inventor
Raghava Krishna KANALA
Naresh KOTTARI
Venkatesan SANTHANAM
Ravi BALASUBRAMANIAM
Original Assignee
Hindustan Petroleum Corporation Limited
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 Hindustan Petroleum Corporation Limited filed Critical Hindustan Petroleum Corporation Limited
Publication of WO2022172279A1 publication Critical patent/WO2022172279A1/fr

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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
    • C23F11/04Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in markedly acid liquids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/28Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with other reducing agents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G7/00Distillation of hydrocarbon oils
    • C10G7/10Inhibiting corrosion during distillation
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G75/00Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
    • C10G75/02Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of corrosion inhibitors
    • 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
    • C23F11/141Amines; Quaternary ammonium compounds

Definitions

  • the present invention describes a corrosion inhibiting dioleyl compound and synthesis process for preparing the said dioleyl compound. Further, the present invention also describes corrosion inhibiting fdm forming amine formulation prepared from the said dioleyl compound. Wherein, the said corrosion inhibiting film forming amine formulation is used for inhibiting corrosion of metal surfaces, especially, inhibiting corrosion of crude oil units.
  • HC1 gas To mitigate this corrosion as caused by HC1 gas, some neutralizing amines and film forming amines are dosed at overhead section of the crude unit.
  • the mechanism of film forming amine are the formation of a film which can act as a hydrophobic barrier against corrosive species, such as, HC1.
  • the US20160002793 A 1 discloses a method and compositions for inhibiting corrosion on metal surfaces of gas turbine air compressors.
  • the methods comprise contacting the metal surfaces with a corrosion inhibiting composition comprising at least one filming amine.
  • a corrosion inhibiting composition comprising at least one filming amine.
  • a polyamine of formula H2N-((CH2)x -NH)y - R1 is also disclosed, wherein, x ranges from about 1 to about 8; y ranges from about 0 to about 7; and R1 is a saturated or unsaturated aliphatic C12-C24 hydrocarbon radical.
  • the filming amine as used herein may be any material that forms an organic film on metal surfaces thereby preventing corrosive and oxidizing materials from contacting the metal surfaces.
  • W02020174607A1 discloses a method for providing corrosion protection to a water-steam circuit having both internal surfaces made of aluminium or aluminium alloy and internal surfaces made of steel.
  • the said method comprises operating the water-steam circuit with water having a pH value, measured at 22°C, in the range of pH 8.8 to 10.0, in particular in the range of pH 9.0 to 9.6, especially in the range of pH 9.2 to 9.6 and containing a film forming amine.
  • Oleyl amine/oleyl 1,3 diamine acts as barrier for the corrosive species and thus protects the metal surfaces.
  • the objective of the present invention is to provide an easily synthesizable dioleyl compound for inhibiting the corrosion of metal surfaces.
  • the main objective of the present invention is to provide a method for synthesizing a corrosion inhibiting dioleyl compound for inhibiting corrosion in the crude distillation units/hydro treating units/fluid catalytic cracking units.
  • the specific objective of the present invention is to provide a corrosion inhibiting film forming amine formulation for inhibiting corrosion of metal surfaces, especially, corrosion caused by HC1 gas in the crude oil units.
  • the present invention discloses a corrosion inhibiting dioleyl compound and a method for synthesizing the said corrosion inhibiting dioleyl compound.
  • the corrosion inhibiting dioleyl compound is prepared by firstly preparing a reaction mixture by adding oleyl amine (14gm) into acetyl acetone (5gm) and stirring for 6 hours at 60°C. Then adding the solution of the said reaction mixture in 200ml methanol, and then treating with sodium borohydride at 0°C, and then warming to Reaction Temperature (RT) and stirred at Reaction Temperature (RT) for 12 hours. Thereafter, the final compound is diluted with ethylacetate and washed with a washing agent.
  • the present invention also discloses a process for preparing a corrosion inhibiting formulation.
  • the process includes preparing an amine solution of Cyclohexylamine, Ethanolamine (MEA) and Morpholine, all taken in equal ratios. Further, the corrosion inhibiting dioleyl compound as prepared above is added in the said amine solution.
  • the said amine solution is 90-99 weight percent and corrosion inhibiting dioleyl compound of Formula-1 is 1-10 weight percent.
  • the ratio of the said amine solution and the corrosion inhibiting dioleyl compound is 95:5 weight percent. Then, the solution as obtained is stirred for 20 minutes to obtain the said corrosion inhibiting formulation.
  • the present invention also discloses use of the said corrosion inhibiting dioleyl compound in the said corrosion inhibiting formulation to control corrosion of a crude distillation unit, a hydrocarbon treating unit, and/or a fluid catalytic unit.
  • Fig. 2 Illustrates the rate of mass change due to adsorption on a SS-coated quartz crystal for different film forming amine formulations.
  • the present invention also discloses a method for synthesizing the said corrosion inhibiting dioleyl compound.
  • the corrosion inhibiting dioleyl compound is prepared by firstly preparing a reaction mixture by adding oleyl amine (14g) into a solution of acetyl acetone and then stirring the said reaction mixture for 6 hours at 60°C.
  • the corrosion inhibiting dioleyl compound of Formula- 1 as prepared hereinabove is added in the said amine solution.
  • the ratio of the said amine solution and the corrosion inhibiting dioleyl compound is 95:5 weight percent.
  • the solution as obtained is stirred for 20 minutes to obtain the said film forming amine formulation.
  • the said fdm forming amine formulation is used to control corrosion of a crude distillation unit, a hydrocarbon treating unit, a fluid catalytic unit especially protecting these units from the acidic by-products such as HC1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé dioléyle inhibiteur de corrosion, un procédé pour le synthétiser et une formulation d'amine formant un film inhibant la corrosion préparée à partir dudit composé dioléyle. Ladite formulation d'amine formant un film inhibant la corrosion est utilisée pour inhiber la corrosion d'unités de distillation, d'unités d'hydro-traitement de pétrole brut et d'unités de craquage catalytique de fluide. Le composé dioléyle divulgué dans la présente invention peut être synthétisé facilement et réduit le coût global de préparation de la formulation d'amine formant un film inhibant la corrosion. De plus, la formulation d'amine formant un film inhibant la corrosion telle que préparée à partir dudit composé dioléyle présente d'excellentes propriétés d'inhibition de la corrosion.
PCT/IN2021/050346 2021-02-15 2021-04-07 Composé dioléyle inhibant la corrosion, et formulation d'amine de celui-ci formant un film inhibant la corrosion WO2022172279A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN202141006275 2021-02-15
IN202141006275 2021-02-15

Publications (1)

Publication Number Publication Date
WO2022172279A1 true WO2022172279A1 (fr) 2022-08-18

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PCT/IN2021/050346 WO2022172279A1 (fr) 2021-02-15 2021-04-07 Composé dioléyle inhibant la corrosion, et formulation d'amine de celui-ci formant un film inhibant la corrosion

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WO (1) WO2022172279A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160002793A1 (en) 2013-03-01 2016-01-07 General Electric Company Compositions and methods for inhibiting corrosion in gas turbine air compressors
EP3246380A1 (fr) * 2016-05-18 2017-11-22 Bharat Petroleum Corporation Ltd. Régulation de la corrosion de distillat de tête dans une unité de production de pétrole brut au moyen de mélanges d'amines multiples
WO2020008477A1 (fr) * 2018-07-04 2020-01-09 Hindustan Petroleum Corporation Limited Formulation d'amine de neutralisation et son procédé de préparation
WO2020051302A1 (fr) * 2018-09-06 2020-03-12 Ecolab Usa Inc. Inhibiteurs de corrosion à base de propylènediamine oléylique
WO2020174607A1 (fr) 2019-02-27 2020-09-03 Kurita Water Industries Ltd. Procédé pour fournir une protection contre la corrosion à un circuit eau-vapeur

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160002793A1 (en) 2013-03-01 2016-01-07 General Electric Company Compositions and methods for inhibiting corrosion in gas turbine air compressors
EP3246380A1 (fr) * 2016-05-18 2017-11-22 Bharat Petroleum Corporation Ltd. Régulation de la corrosion de distillat de tête dans une unité de production de pétrole brut au moyen de mélanges d'amines multiples
WO2020008477A1 (fr) * 2018-07-04 2020-01-09 Hindustan Petroleum Corporation Limited Formulation d'amine de neutralisation et son procédé de préparation
WO2020051302A1 (fr) * 2018-09-06 2020-03-12 Ecolab Usa Inc. Inhibiteurs de corrosion à base de propylènediamine oléylique
WO2020174607A1 (fr) 2019-02-27 2020-09-03 Kurita Water Industries Ltd. Procédé pour fournir une protection contre la corrosion à un circuit eau-vapeur

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