WO2014031530A1 - Inhibition de la corrosion provoquée par les solutions aqueuses à base d'aldéhydes - Google Patents

Inhibition de la corrosion provoquée par les solutions aqueuses à base d'aldéhydes Download PDF

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Publication number
WO2014031530A1
WO2014031530A1 PCT/US2013/055560 US2013055560W WO2014031530A1 WO 2014031530 A1 WO2014031530 A1 WO 2014031530A1 US 2013055560 W US2013055560 W US 2013055560W WO 2014031530 A1 WO2014031530 A1 WO 2014031530A1
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WO
WIPO (PCT)
Prior art keywords
phosphate salt
soluble phosphate
basic soluble
combinations
group
Prior art date
Application number
PCT/US2013/055560
Other languages
English (en)
Inventor
Stephen R. Keenan
Jonathan Collins
Sunder Ramachandran
Vladimir Jovancicevic
Rose Tompkins
Grahame N: TAYLOR
Richard L. Martin
Michael L. Walker
Original Assignee
Baker Hughes Incorporated
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
Priority claimed from US13/589,794 external-priority patent/US9068269B2/en
Application filed by Baker Hughes Incorporated filed Critical Baker Hughes Incorporated
Publication of WO2014031530A1 publication Critical patent/WO2014031530A1/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
    • 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
    • C23F11/167—Phosphorus-containing compounds
    • C23F11/1673—Esters of phosphoric or thiophosphoric acids
    • 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
    • C23F11/18—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 inorganic inhibitors
    • C23F11/184—Phosphorous, arsenic, antimony or bismuth containing compounds

Definitions

  • the invention relates to the prevention or mitigation of corrosion.
  • the invention particularly relates to the prevention or mitigation of corrosion caused by aldehydes.
  • H 2 S Sulfide (H 2 S) and/or mercaptans are often encountered in the exploration for and production of oil and natural gas.
  • the presence of H 2 S and mercaptans is usually objectionable because they may react with other hydrocarbons or fuel system components.
  • Another reason that the H 2 S and mercaptans are objectionable is that they are often highly corrosive.
  • Still another reason that H 2 S and mercaptans are undesirable is that they have highly noxious odors.
  • the odors resulting from H 2 S and mercaptans are detectable by the human nose at comparatively low concentrations and are well known.
  • mercaptans are used to odorize natural gas and used as a repellant by skunks and other animals.
  • H 2 S and/or mercaptans One solution to these problems is to "scavenge" H 2 S and/or mercaptans.
  • Certain aldehydes are known to be useful for these purposes.
  • glyoxal OHCCHO
  • Glyoxal and other aldehydes such as acrolein and formaldehyde are known to be useful in a variety of other applications such as biocides, disinfectants, and the like.
  • Aldehydes may be corrosive to metals such as aluminum, iron, and steel. It would be desirable to be able to employ such aldehydes at high concentration while minimizing the corrosion caused to metals in contact with the aldehydes.
  • the invention is a method for employing an aldehyde in an aqueous solution while mitigating corrosion to metal in contact with the aldehyde solution.
  • the method includes employing a corrosion inhibitor prepared using a member selected from the group consisting of a mono-basic soluble phosphate salt, di-basic soluble phosphate salt, a tri-basic soluble phosphate salt, a phosphate ester, a thiophosphate ester, a thioamine, Mannich Reaction Product, and combinations thereof.
  • the invention is, in a process for the exploration for or the production of crude oil and/or natural gas, employing an aldehyde as a H 2 S sulfide scavenger and employing a corrosion inhibitor prepared using a member selected from the group consisting of a mono-basic soluble phosphate salt, di-basic soluble phosphate salt, a tri-basic soluble phosphate salt, a phosphate ester, a thiophosphate ester, a thioamine, Mannich Reaction Product (MRP), and combinations thereof.
  • an aldehyde as a H 2 S sulfide scavenger
  • a corrosion inhibitor prepared using a member selected from the group consisting of a mono-basic soluble phosphate salt, di-basic soluble phosphate salt, a tri-basic soluble phosphate salt, a phosphate ester, a thiophosphate ester, a thioamine, Mannich Reaction Product (MRP
  • the disclosure is directed to a method for employing an aldehyde in an aqueous solution while mitigating corrosion to metal in contact with the aldehyde solution, the method including employing a corrosion inhibitor prepared using a formulation including a mono-, di- or tri- basic soluble phosphate salt.
  • a corrosion inhibitor prepared using a formulation including a mono-, di- or tri- basic soluble phosphate salt.
  • an aldehyde aqueous solution is employed.
  • the aldehydes which may be employed in the practice of the method of the disclosure include, but are not limited to glyoxal, acrolein, glutaraldehyde, formaldehyde, and combinations thereof.
  • the aldehydes may be particularly a problem when in a comparatively concentrated form.
  • the method of the disclosure is often employed where the aldehydes are present at a concentration of from about 4 to about 95% by weight.
  • the aldehydes are more dilute or concentrated, they often are not sufficiently corrosive to warrant a corrosion inhibitor; however they may be employed anytime that the aldehydes are present at a concentration such that a significant amount of corrosion may occur. This will vary according to the type of metal the aldehydes are contacting and the level of resilience of the system to which they are applied.
  • the aldehyde will be present at a concentration of from about 5 to about 80 wt.%. In other embodiments, the concentration may be from about 10 to about 75 wt.%.
  • a mono-, di- or tri-basic soluble phosphate salt is used to mitigate corrosion by the aldehydes as discussed about. While any soluble salt may be used, in many embodiments, the phosphate salts employed will be selected from the group consisting of LJH2PO4 NaH 2 P0 4 , Na 2 HP0 4 , Na 3 P0 4 , KH 2 P0 4 , K 2 HP0 4 ; K 3 P0 4 ; and combinations thereof.
  • the mono, di, or tri-basic soluble phosphate salt may include more than one cation.
  • the mono-, di- or tri-basic soluble phosphate salt may be selected from the group consisting of lithium, potassium, and sodium.
  • the phosphate salts may be employed in any concentration effective to prevent or mitigate corrosion caused by the aldehydes.
  • the mono-, di- or tri-basic phosphate salts may be present at a concentration of from about 10 ppm to 10% (by wt). In other embodiments, they may be present at a concentration of from about 100 ppm to about 2%. In still other embodiments, they are present at a concentration of from about 1000 ppm to about 1 percent.
  • the aldehydes may be admixed with a phosphate ester, a thiophosphate ester, or a thioamine.
  • phosphate esters means compounds having the general formula:
  • n is an integer ranging from about 0 to about 20; and R1 , R2, and R3 are H or a C1 -C18 alkyl, aryl or alkyl aryl moiety. The sum of all n's is at least 1 .
  • Exemplary phosphate esters include but are not limited to: methyl phosphate, dimethyl phosphate, trimethyl phosphate, ethyl phosphate, diethyl phosphate, triethyl phosphate, butyl phosphate, dibutyl phosphate, tributyl phosphate, 2-ethylhexyl phosphate, 2-diethyhexyl phosphate, tri(2-ethylhexyl) phosphate, ibutoxyethyl phosphate, dibutoxyethyl phosphate tributoxyethyl phosphate, phenyl phosphate, diphenyl phosphate triphenyl phosphate, cresyl phosphate, dicresyl phosphate, tricredyl phosphate, xylenyl phosphate, dixylenyl phosphate, trixylenyl phosphate, isopropylphenyl phosphate, bis(is
  • Aromatic condensed phosphate esters may also be used and include, but are not limited to resorcinol polyphenylphosphate, resorcinol poly(di-2,6- xylyl)phosphate, bisphenol A polycredylphosphate, hydroquinone poly(2,6- xylyl)phosphate, and a condensate thereof.
  • the thiophophate esters useful with the method of the disclosure include, but are not limited to bis(2-ethylhexyl) thiophosphate, diethyl thiophosphate, dimethyl thiophosphate, bis(2-ethylhexyl) dithiophosphate, diethyl dithiophosphate and dimethyl dithiophosphate.
  • Dilauryl dithiophosphate, a lauryl trithiophosphite and a triphenyl thiophosphate may also be used with the methods of the application.
  • the thioamines may include, but are not limited to: N,N-dithio-bis- dimethylamine, ⁇ , ⁇ -dithio - bis - diethylamine, N,N-dithio-bis-dipropylamine, N,N-dithio-bis-diisopropylamine, ⁇ , ⁇ -dithio-bis-dibutylamine, N, N-dithio-bis- diisobutylamine, ⁇ , ⁇ -dithio-bisdiamylamine, N.N-dithio-bis-dihexylamine, N, N- dithiobis - diheptylamine, and ⁇ , ⁇ -dithio-bis-dioctylamine.
  • the N,N- monothioamines as: for example ⁇ , ⁇ -thio-bis-morpholine, N,N-thio-bis- dimethylamine, N,N-thio-bis-diethylamine, ⁇ , ⁇ -thio-bis-dipropylamine, and N,N-thio-bis-diisopropylamine.
  • MRP Mannich Reaction Products
  • the Mannich Reaction Product may be prepared by in situ Mannich reaction of tris(hydroxymethyl)aminomethane with a mixture of the corresponding nitroparaffin and formaldehyde followed by reduction of the nitro group of the product to an amine via hydrogenation in the presence of a hydrogenation catalyst.
  • the Mannich Reaction Product may be prepared by admixing a phenol, an alkanolamines, and a formaldehyde mixed in molar ratios resulting in an initiator which can be alkoxylated to prepare polyols.
  • the Mannich Reaction Product may be prepared using an aldehyde is selected from the group consisting of formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, and stearaldehyde, benzaldehyde, salicylaldehyde, furfural, thiophene aldehyde, and formaldehyde-producing reagents, where the formaldehyde-producing regent is selected from the group consisting of paraformaldehyde and formalin, atoms. This would include formaldehyde, but could also include other aldehydes such a propionaldhyde.
  • the phenol component may be selected from phenol and 4,4'-dihydroxydiphenylpropane-2,2; but also alkyl substituted phenols wherein the aromatic ring may have one or more alkyl moieties having from 1 to 20 carbons.
  • One such compound would be nonyl phenol.
  • Amines useful with the method of the disclosure include primary amines and secondary amines, but these compounds may also further comprise functional groups which are inert in a Mannich reaction, e.g. tertiary amino groups, alkoxy groups and hydroxyl groups.
  • Such primary amines include those selected from the group consisting of monoalkyl amines, hydroxyalkyl amines and dialkyaminoalkyl amines.
  • each alkyl group in the amines may comprise from 1 to 20 carbon atoms which may be interrupted by non adjectent oxygen atoms.
  • Suitable primary amines are propyl amine, n-butyl amine, aminoethanol, 2- (C ( i ) -C (4) -alkoxy)ethyl amine, such as 2-methoxyethyl amine, 2-ethoxyethyl amine, 2-(hydroxy-C ( i ) -C (4) -alkoxy)ethyl amine such as 2-(hydroxyalkoxy)ethyl amine, and 2-(di-C ( i ) -C (4) -alkylamino)ethyl amine such as 2- dimethylaminoethyl amine, 2-diethylaminoethyl amine and 3-(di-C ( i ) -C (4) - alkylamino)propyl amine such as 3-dimethylaminopropyl amine and 3- diethylaminopropyl amine.
  • Suitable secondary amines are di-C ( ) - C ( io ) -alkyl amines such as diethyl amine, di-n-propyl amine, diisopropyl amine, dicyclohexyl amine, cyclic amines such as morpholine and piperidine, di- (hydroxy-C ( i ) -C (4) -alkyl) amines such as diethanol amine, etc.
  • the amine can even be just ammonia.
  • the phosphate salts or other corrosion inhibitors, aldehyde, and water may be admixed in any way known to be useful to those of ordinary skill in the art of preparing additives.
  • these components may be combined in a single container batch and admixed using a static or active mixer.
  • the aldehyde and water may be first admixed and then a solution of the mono-, di- or tri-basic phosphate salt introduced.
  • the three streams may be introduced simultaneous through a static mixes into a vessel.
  • the alkaline phosphate salts useful with the method of the disclosure may be employed at a pH range of from about 4.0 to about 9.0. In some embodiments, the pH range may vary from about 4.5 to about 8.5 while in other embodiments the pH may be from about 5 to about 9.
  • the mono-, di- and tri-basic salt employed in the method of disclosure work in two ways to prevent corrosion.
  • the phosphates contact and build an inorganic insoluble metal phosphate film on the metal surface.
  • an iron phosphate film forms.
  • the basic nature of the mono, di, and tri-basic phosphate salts either partially or perhaps fully removes the acidic H 2 S(s) from the aldehydes. Interfering with the acid H 2 S could affect the ability of the aldehydes to chelate metal thus removing or at least moderating this corrosion mechanism.
  • the disclosure includes a process for the exploration for or the production of crude oil and/or natural gas, the process including employing an aldehyde as a H 2 S sulfide scavenger and employing a corrosion inhibitor prepared from a formulation including a mono-, di- or tri- basic soluble phosphate salt.
  • the process of the disclosure includes both exploration and production. Exploration includes drilling an oil and gas well, and then completing the well to start production of hydrocarbons. Production includes producing production fluid from the oil and gas well.
  • the drilling fluids, formation brines, or the crude oil and/or natural gas encountered in either exploration or production may include undesirable levels of H2S and/or other mercaptans. Employment of an aldehyde scavenger as well as a corrosion inhibitor may be required in these circumstances.
  • the aldehyde scavengers maybe employed in the process of the disclosure in any way known to be useful to those of ordinary skill in the art of producing oil and gas. For example, it may be atomized and introduced into a gas stream or directly admixed, liquid phase to liquid phase, with a crude oil stream.
  • the hydrogen sulfide-containing stream may be passed through a contact tower or bubble tower including the scavenger of the application.
  • Such towers may include other scavengers as well such as those disclosed in U.S. Patent Application No 5508012, the disclosure of which is hereby incorporated by reference in its entirety. It may also be employed as in, for example, the U.S. Provisional Patent Application having the serial number 61/4671 16, which application is fully incorporated herein by reference.
  • Corrosion tests were performed by holding mild steel corrosion coupons at 60°C for the times shown in the Table. Corrosion was determined as mils per year loss of metal. The concentration of each compound tested was 1 % except as noted below. The blank (control) and each sample was 40% by weight aqueous glyoxal. Results are shown below in Table 1.
  • Corrosion tests were performed by immersing mild steel corrosion coupons at 35°C into glyoxal-containing solutions in C02 for 1 hour pre- corrosion (blank) and monitor corrosion rate by linear polarization resistance (LPR). After the corrosion rate is stabilized the corrosion inhibitor was injected and rate continuously monitored for approximately 20 hours. Corrosion was determined as mils per year (mpy). The concentration of corrosion inhibitors varied from 30-550 ppm. The solution consisted of 5% by weight aqueous glyoxal. Results are shown below in the Table 2.
  • Example 3 The method of Example 3 is repeated substantially identically except that the temperature is 55°C, the time is 17 hours, the concentration of glyoxal is 20% and the concentration of the additives and the resulting corrosions rates are shown below in Table 3. Table 3

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Abstract

Les aldéhydes utiles en tant que piégeurs de sulfure d'hydrogène peuvent être corrosifs pour certains métaux tels que l'acier, le fer et l'aluminium. L'effet corrosif des aldéhydes peut être atténué par un inhibiteur de corrosion sélectionné dans le groupe constitué par : un sel de phosphate dibasique soluble, un sel de phosphate tribasique soluble, un ester de phosphate, un ester de thiophosphate, un amine soufré, un produit de réaction de Mannich, et une combinaison de ceux-ci.
PCT/US2013/055560 2012-08-20 2013-08-19 Inhibition de la corrosion provoquée par les solutions aqueuses à base d'aldéhydes WO2014031530A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13/589,794 US9068269B2 (en) 2011-10-05 2012-08-20 Inhibiting corrosion caused by aqueous aldehyde solutions
US13/589,794 2012-08-20

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WO2014031530A1 true WO2014031530A1 (fr) 2014-02-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3566762A3 (fr) * 2018-04-19 2020-02-12 Nexgen Oilfield Chemicals, LLC Procédés et compositions permettant de récupérer des sulfures et du dioxyde de carbone à partir de pétrole et de gaz naturel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4554090A (en) * 1984-03-09 1985-11-19 Jones L W Combination corrosion/scale inhibitor
US5091113A (en) * 1987-05-15 1992-02-25 Ciba-Geigy Corporation Corrosion inhibiting composition
US20050169794A1 (en) * 2004-02-04 2005-08-04 Welton Thomas D. Thiol / aldehyde corrosion inhibitors
US20060194700A1 (en) * 2005-02-25 2006-08-31 Weatherford/Lamb Corrosion inhibitor systems for low, moderate and high temperature fluids and methods for making and using same
US20060264335A1 (en) * 2005-05-17 2006-11-23 Bj Services Company Corrosion inhibitor intensifier and method of using the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4554090A (en) * 1984-03-09 1985-11-19 Jones L W Combination corrosion/scale inhibitor
US5091113A (en) * 1987-05-15 1992-02-25 Ciba-Geigy Corporation Corrosion inhibiting composition
US20050169794A1 (en) * 2004-02-04 2005-08-04 Welton Thomas D. Thiol / aldehyde corrosion inhibitors
US20060194700A1 (en) * 2005-02-25 2006-08-31 Weatherford/Lamb Corrosion inhibitor systems for low, moderate and high temperature fluids and methods for making and using same
US20060264335A1 (en) * 2005-05-17 2006-11-23 Bj Services Company Corrosion inhibitor intensifier and method of using the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3566762A3 (fr) * 2018-04-19 2020-02-12 Nexgen Oilfield Chemicals, LLC Procédés et compositions permettant de récupérer des sulfures et du dioxyde de carbone à partir de pétrole et de gaz naturel

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