EP2593535A2 - Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons - Google Patents

Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons

Info

Publication number
EP2593535A2
EP2593535A2 EP11807425.1A EP11807425A EP2593535A2 EP 2593535 A2 EP2593535 A2 EP 2593535A2 EP 11807425 A EP11807425 A EP 11807425A EP 2593535 A2 EP2593535 A2 EP 2593535A2
Authority
EP
European Patent Office
Prior art keywords
hydrogen sulfide
scavenger
alpha
bis
fluid
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.)
Ceased
Application number
EP11807425.1A
Other languages
German (de)
French (fr)
Other versions
EP2593535A4 (en
Inventor
Dennis R. Compton
Byron J. Strickland
Juan M. Garcia, Iii
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.)
ChampionX LLC
Original Assignee
Nalco Co LLC
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 Nalco Co LLC filed Critical Nalco Co LLC
Publication of EP2593535A2 publication Critical patent/EP2593535A2/en
Publication of EP2593535A4 publication Critical patent/EP2593535A4/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN

Definitions

  • This invention relates generally to the treatment of sour gas and liquid hydrocarbon to remove or reduce the levels of hydrogen sulfide therein.
  • the toxicity of hydrogen sulfide in hydrocarbon fluids is well known in the industry. This has caused considerable expense and efforts to be expended annually to reduce its content to a safe level.
  • a regenerative system for treating sour gas streams.
  • These systems typically employ a compound used in an absorption tower to contact the produced fluids and selectively absorb the hydrogen sulfide and possibly other toxic materials such as carbon dioxide and mercaptans. The absorption compound is then regenerated and reused in the system.
  • Typical hydrogen sulfide absorption materials include alkanolamines, PEG, hindered amines, and other species that can be regenerated.
  • Nonregenerative scavengers for small plant hydrogen sulfide removal fall into four general categories: 1) aldehyde based, 2) metallic oxide based, 3) caustic based, and 4) other processes.
  • the scavenger reacts with the hydrogen sulfide to form a nonlethal compound or a compound, which can be removed from the hydrocarbon.
  • a chemical compound known as formthionals e.g., trithiane
  • Prior Art aldehyde scavengers typically include low molecular weight aldehydes and ketones and adducts thereof.
  • the low molecular weight aldehydes may also be combined with an alkyl or alkanolamine as disclosed in US Patent 4,748,011.
  • Other aldehyde derived scavengers include the reaction product of low molecular weight alkanolamines and aldehydes as disclosed in US Patent 4,978,512.
  • PCT Application WO 92/01481 discloses a method of reducing sulfides in different applications using certain tri-substituted-hexahydro-s-triazines.
  • German reference DE4027300 discloses a regenerative solvent for removing 3 ⁇ 4S and mercaptans.
  • US Patent 5,347,004 discloses the use of 1,3,5 alkoxyalkylene hexahydro triazines.
  • PCT Application WO 91 US 5232 discloses hydroxyalkyl triazine scavengers, specifically an N,N',N"-tris(2-hydroxyethyl)hexahydro-s-triazine.
  • US Patent 5,774,024 discloses the combination of an alkyl triazine scavenger and quaternary ammonium salt, where the quaternary ammonium salt enhances the effectiveness of the alkyl-triazine..
  • These prior art attempts however are frequently water-based chemicals and require significant mixing to allow the scavenger to effectively contact the hydrocarbon fluid and remove the hydrogen sulfide.
  • At least one embodiment of the invention is directed towards a method for removing hydrogen sulfide from a hydrocarbon fluid.
  • the method comprises contacting the fluid with an effective amount of a composition comprising a hydrogen sulfide scavenger.
  • the amount of hydrogen sulfide scavenger is sufficient to react with the hydrogen sulfide to reduce the amount hydrogen sulfide released into the vapor space .
  • the reaction product of the hydrogen sulfide scavenger and the hydrogen sulfide remain soluble in the hydrocarbon fluid.
  • the hydrogen sulfide scavenger contains at least one alpha-amino ether.
  • composition may include one item selected from the list consisting of:
  • the reaction product of the sulfide scavenging formulation and the hydrogen sulfide may not form a separate fluid layer.
  • the method may also further comprise the step of reacting a secondary amine with a formaldehyde equivalent to form at least some of the scavenging formulation.
  • the hydrocarbon fluid may be a liquid.
  • Alpha-amino ether means a molecule according to the formula:
  • R l9 R 2 , R 3 , R4 are carbon containing side chains containing 1 - 20 carbon atoms and includes cyclic and acyclic compounds.
  • the cyclic compounds can be aromatic or non-aromatic. Examples include but are not limited to, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, morpholino, and phenyl, and they all can be the same group or one or more different groups.
  • B is an ether group, which is either an oxygen atom or a group having an oxygen atom at both ends (such as -OCH 2 0- or-OCsUtO-).
  • Formaldehyde equivalent means a composition of matter containing at least one group according to the formula: ( ⁇ 3 ⁇ 40) ⁇ in which n is an integer greater than or equal to 1, and/or a composition of matter including formaldehyde or related molecules such as
  • Hydrocarbon fluid means a liquid or gas predominantly comprising organic material including but not limited to kerosene, crude oil, crude oil emulsions, oilfield condensate, petroleum residua, refined fuels, distillate fuels, fuel oil, heating oils, diesel fuel, gasoline, jet fuel, bunker fuel oils, and any combination thereof.
  • Non-Regenerative Scavenger means a scavenger, which is consumed by the process of scavenging.
  • Regenerative Scavenger means a scavenger, which is not consumed by the process of scavenging.
  • “Scavenger” means a composition of matter, such as but not limited to alpha- amino ethers, useful in reducing the amount of or mitigating the effects of some other composition of matter, such as but not limited to hydrogen sulfide, in a fluid medium.
  • the hydrogen sulfide in a hydrocarbon fluid is reduced by the introduction of an alpha-amino ether scavenger into the fluid.
  • the alpha-amino ether is a portion of a scavenging formulation is used in a hydrocarbon fluid.
  • the formulation comprises alpha-amino ether and can consist of a carrier liquid as well.
  • the formulation can be introduced into the hydrocarbon fluid by mechanical means including but not limited to injection pumps or any mechanism disclosed in US Patents 5,744,024 and 5,840,177.
  • the gas may be passed through an absorption tower containing a scavenging formulation.
  • alpha-amino ether scavenger is soluble in hydrocarbon fluids, since it is not a water-based product.
  • the hydrogen sulfide scavenger is produced by reacting a secondary amine with formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • the reaction product also comprises 10-25% of the non-ether diamine (compound A).
  • Compound A is an unavoidable side product of the reaction mixture.
  • the reaction can be performed by mixing the reactants in solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
  • solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
  • the ratio of amine to formaldehyde in the reaction mixture is inclusively within the range of 1.5:1 to 1:1.5 and is preferably between 1.2:1 and 1:1.2.
  • any of the R and R' groups correspond to any of the Ri, R 2 , R , and R4, groups described in the definition of "alpha-amino ether".
  • Compound A is ⁇ , ⁇ , ⁇ ', ⁇ '-tetrabutylmethanediamine
  • Compound B is N,N'-oxybis(methylene)bis(N,N-dibutylene), and
  • Compound C is N 5 N'-(methylenebis(oxy)bis(methylene))bis(N,N'-dibutylamine).
  • compositions comprising:
  • Table 1 compares the inventive composition in naphtha at 22 degrees C
  • Table 2 kerosene at 22 degrees C, and Table 3 slurry oil (such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery) at 97 degrees C.
  • slurry oil such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery
  • Tat le 2 tes 22 °C
  • the amount of H 2 S present in the vapor space was determined by measuring the vapor space hydrogen sulfide levels according to ASTM D5705-03. test procedure was modified by running at temperatures other than 60°C. A one-gallon sample was divided into multiple 500 milliliter samples for testing. The treated containers were pre-dosed with Compounds A-C and then the fluid being tested was poured into the container. In each example, the dose ratio was the number used to determine the ppm treat rate for the sample. For table 1 the untreated sample resulted in a vapor space

Abstract

The invention provides a method of removing hydrogen sulfide from hydrocarbon fluids. The method involves using an alpha-amino ether as a hydrogen sulfide scavenger. This allows for the introduction of an oil soluble scavenger in lieu of water-soluble scavengers.

Description

USE OF ALPHA-AMINO ETHERS FOR THE REMOVAL OF HYDROGEN SULFIDE
FROM HYDROCARBONS
Cross-Reference to Related Applications
None.
Statement Regarding Federally Sponsored Research or Development
Not Applicable.
Background of the Invention
This invention relates generally to the treatment of sour gas and liquid hydrocarbon to remove or reduce the levels of hydrogen sulfide therein. The toxicity of hydrogen sulfide in hydrocarbon fluids is well known in the industry. This has caused considerable expense and efforts to be expended annually to reduce its content to a safe level.
In large production facilities, it is generally more economical to install a regenerative system for treating sour gas streams. These systems typically employ a compound used in an absorption tower to contact the produced fluids and selectively absorb the hydrogen sulfide and possibly other toxic materials such as carbon dioxide and mercaptans. The absorption compound is then regenerated and reused in the system. Typical hydrogen sulfide absorption materials include alkanolamines, PEG, hindered amines, and other species that can be regenerated.
Nonregenerative scavengers for small plant hydrogen sulfide removal fall into four general categories: 1) aldehyde based, 2) metallic oxide based, 3) caustic based, and 4) other processes. In the removal of hydrogen sulfide by nonregenerative compounds, the scavenger reacts with the hydrogen sulfide to form a nonlethal compound or a compound, which can be removed from the hydrocarbon. For example, when formaldehyde reacts with hydrogen sulfide a chemical compound known as formthionals (e.g., trithiane) is formed. Prior Art aldehyde scavengers typically include low molecular weight aldehydes and ketones and adducts thereof. The low molecular weight aldehydes may also be combined with an alkyl or alkanolamine as disclosed in US Patent 4,748,011. Other aldehyde derived scavengers include the reaction product of low molecular weight alkanolamines and aldehydes as disclosed in US Patent 4,978,512. PCT Application WO 92/01481 discloses a method of reducing sulfides in different applications using certain tri-substituted-hexahydro-s-triazines. German reference DE4027300 discloses a regenerative solvent for removing ¾S and mercaptans. US Patent 5,347,004 discloses the use of 1,3,5 alkoxyalkylene hexahydro triazines. PCT Application WO 91 US 5232 discloses hydroxyalkyl triazine scavengers, specifically an N,N',N"-tris(2-hydroxyethyl)hexahydro-s-triazine. US Patent 5,774,024 discloses the combination of an alkyl triazine scavenger and quaternary ammonium salt, where the quaternary ammonium salt enhances the effectiveness of the alkyl-triazine.. These prior art attempts however are frequently water-based chemicals and require significant mixing to allow the scavenger to effectively contact the hydrocarbon fluid and remove the hydrogen sulfide.
Thus there is clear need and utility for an improved method of scavenging hydrogen sulfide from hydrocarbon fluids using scavengers that are soluble in the fluid that is being treated. The art described in this section is not intended to constitute an admission that any patent, publication or other information referred to herein is "prior art" with respect to this invention, unless specifically designated as such. In addition, this section should not be construed to mean that a search has been made or that no other pertinent information as defined in 37 CFR § 1.56(a) exists.
Brief Summary of the Invention
At least one embodiment of the invention is directed towards a method for removing hydrogen sulfide from a hydrocarbon fluid. The method comprises contacting the fluid with an effective amount of a composition comprising a hydrogen sulfide scavenger. The amount of hydrogen sulfide scavenger is sufficient to react with the hydrogen sulfide to reduce the amount hydrogen sulfide released into the vapor space . The reaction product of the hydrogen sulfide scavenger and the hydrogen sulfide remain soluble in the hydrocarbon fluid. The hydrogen sulfide scavenger contains at least one alpha-amino ether.
The composition may include one item selected from the list consisting of:
Ν,Ν' -oxybis(methylene)bis(N,N-dibutylamine) ,
N,N'-(methylenebis(oxy)bis(methyIene))bis(N,N-dibutylamine),
and any combination thereof.
The reaction product of the sulfide scavenging formulation and the hydrogen sulfide may not form a separate fluid layer. The method may also further comprise the step of reacting a secondary amine with a formaldehyde equivalent to form at least some of the scavenging formulation. The hydrocarbon fluid may be a liquid.
Detailed Description of the Invention
For purposes of this application the definition of these terms is as follows:
"Alpha-amino ether" means a molecule according to the formula:
Where: Rl9 R2, R3, R4, are carbon containing side chains containing 1 - 20 carbon atoms and includes cyclic and acyclic compounds. The cyclic compounds can be aromatic or non-aromatic. Examples include but are not limited to, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, morpholino, and phenyl, and they all can be the same group or one or more different groups. B is an ether group, which is either an oxygen atom or a group having an oxygen atom at both ends (such as -OCH20- or-OCsUtO-).
"Formaldehyde equivalent" means a composition of matter containing at least one group according to the formula: (Ο¾0)η in which n is an integer greater than or equal to 1, and/or a composition of matter including formaldehyde or related molecules such as
paraformaldehyde, and/or s-trioxane.
"Hydrocarbon fluid" means a liquid or gas predominantly comprising organic material including but not limited to kerosene, crude oil, crude oil emulsions, oilfield condensate, petroleum residua, refined fuels, distillate fuels, fuel oil, heating oils, diesel fuel, gasoline, jet fuel, bunker fuel oils, and any combination thereof.
"Non-Regenerative Scavenger" means a scavenger, which is consumed by the process of scavenging.
"Regenerative Scavenger" means a scavenger, which is not consumed by the process of scavenging.
"Scavenger" means a composition of matter, such as but not limited to alpha- amino ethers, useful in reducing the amount of or mitigating the effects of some other composition of matter, such as but not limited to hydrogen sulfide, in a fluid medium.
In the event that the above definitions or a description stated elsewhere in this application is inconsistent with a meaning (explicit or implicit) which is commonly used, in a dictionary, or stated in a source incorporated by reference into this application, the application and the claim terms in particular are understood to be construed according to the definition or description in this application, and not according to the common definition, dictionary definition, or the definition that was incorporated by reference. In light of the above, in the event that a term can only be understood if it is construed by a dictionary, if the term is defined by the Kirk-Othmer Encyclopedia of Chemical Technology, 5th Edition, (2005), (Published by Wiley, John & Sons, Inc.) this definition shall control how the term is to be defined in the claims.
In at least one embodiment, the hydrogen sulfide in a hydrocarbon fluid is reduced by the introduction of an alpha-amino ether scavenger into the fluid.
In at least one embodiment the alpha-amino ether is a portion of a scavenging formulation is used in a hydrocarbon fluid. The formulation comprises alpha-amino ether and can consist of a carrier liquid as well. The formulation can be introduced into the hydrocarbon fluid by mechanical means including but not limited to injection pumps or any mechanism disclosed in US Patents 5,744,024 and 5,840,177. In the context of gaseous hydrocarbon fluids, the gas may be passed through an absorption tower containing a scavenging formulation.
One advantage of the use of the alpha-amino ether scavenger over other scavengers is that the alpha-amino ether scavenger is soluble in hydrocarbon fluids, since it is not a water-based product.
As illustrated in FIG. 1, in at least one embodiment the hydrogen sulfide scavenger is produced by reacting a secondary amine with formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane. This produces a composition of matter that predominantly comprises two forms of alpha-amino ethers (compounds B and C). 10%-25% of the composition is a mono oxygen ether (compound B) and 50%-80% of the composition is a bis oxygen ether with a single carbon atom between the ether oxygens (compound C). The reaction product also comprises 10-25% of the non-ether diamine (compound A). Compound A is an unavoidable side product of the reaction mixture. The reaction can be performed by mixing the reactants in solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
In at least one embodiment the ratio of amine to formaldehyde in the reaction mixture is inclusively within the range of 1.5:1 to 1:1.5 and is preferably between 1.2:1 and 1:1.2.
In at least one embodiment any of the R and R' groups correspond to any of the Ri, R2, R , and R4, groups described in the definition of "alpha-amino ether".
In at least one embodiment when R is n-butyl and R' is H then:
Compound A is Ν,Ν,Ν',Ν'-tetrabutylmethanediamine,
Compound B is N,N'-oxybis(methylene)bis(N,N-dibutylene), and
Compound C is N5N'-(methylenebis(oxy)bis(methylene))bis(N,N'-dibutylamine).
At least some contemplated scavenging compositions include formulations comprising:
(Compound A, B, and C), (A and B), (A and C), (B and C), (C alone), and (B alone). EXAMPLES
The foregoing may be better understood by reference to the following example, which is presented for purposes of illustration and is not intended to limit the scope of the invention.
Samples of hydrocarbon fluids were tested to determine the efficiency of the scavenger. Table 1 compares the inventive composition in naphtha at 22 degrees C,
Table 2 kerosene at 22 degrees C, and Table 3 slurry oil (such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery) at 97 degrees C. The samples
contained variable levels of hydrogen sulfide and were comparatively treated with various dosages of alpha-amino ether scavenger or left untreated, and the amounts H2S reduced in each sample was recorded.
!
Table 1: Naphtha 22 'C
H2S
ppm H2S Percent Dose
Treatment fppm) Reduced Reduction Ratio Time
Untreated 800
Compounds A- C 20 780 97.5 0.2 2 h
Compounds A- C 6 794 99.2 0.3 2 h
Compounds A- C 3 797 99.6 0.2 24 h
Compounds A- C <1 >799 99.9 0.3 24h
ί
Compounds A- C 12 (4) 788 (796) 98.5 (99.5) 0.2 (24h)
Tat le 2: tes 22 °C
testes ppm H2S Percent Dose
Treatment (ppm) Reduced Reduction Ratio Time
Untreated 1400
Compounds A - C 400 1000 71 0.1 2 h
Compounds A - C 220 1180 84 0.2 2 h
Compounds A - C 95 1305 93 0.3 2 h
Table 3: Slurry oil 97 °C
H2S
ppm H2S Percent Dose
Treatment (ppm) Reduced Reduction Ratio Time
Untreated 1300
Compounds A - C 450 850 65 0.1 2.5 h
Compounds A - C 240 1060 82 0.2 2.5 h
Compounds A - C 180 1120 86 0.3 2.5 h
Compounds A - C 140 1160 89 0.4 2.5 h
Compounds A - C 90 1210 93 0.5 2.5 h
The amount of H2S present in the vapor space was determined by measuring the vapor space hydrogen sulfide levels according to ASTM D5705-03. test procedure was modified by running at temperatures other than 60°C. A one-gallon sample was divided into multiple 500 milliliter samples for testing. The treated containers were pre-dosed with Compounds A-C and then the fluid being tested was poured into the container. In each example, the dose ratio was the number used to determine the ppm treat rate for the sample. For table 1 the untreated sample resulted in a vapor space
hydrogen sulfide measurement of 800 ppm. A dose ratio of 0.2 indicates the sample was treated with 160 ppm of additive. A dose ratio of 0.3 indicates that the sample was
treated with 240 ppm of additive.
This data demonstrates that the presence of the alpha-amino ether scavenger reduced the H2S in the hydrocarbon fluids in a relatively short amount of time and continued to reduce the H2S the longer the sample was exposed to the alpha-amino ether prior to testing.
While this invention may be embodied in many different forms, there are shown in the drawings and described in detail herein specific preferred embodiments of the invention. The present disclosure is an exemplification of the principles of the
invention and is not intended to limit the invention to the particular embodiments
illustrated. All patents, patent applications, scientific papers, and any other referenced materials mentioned herein are incorporated by reference in their entirety. Furthermore, the invention encompasses any possible combination of some or all of the various
embodiments described herein and incorporated herein.
The above disclosure is intended to be illustrative and not exhaustive. This description will suggest many variations and alternatives to one of ordinary skill in this art. All these alternatives and variations are intended to be included within the scope of the claims where the term "comprising" means "including, but not limited to". Those familiar with the art may recognize other equivalents to the specific embodiments described herein which equivalents are also intended to be encompassed by the claims.
All ranges and parameters disclosed herein are understood to encompass any and all subranges subsumed therein, and every number between the endpoints. For example, a stated range of "1 to 10" should be considered to include any and all subranges between (and inclusive of) the minimum value of 1 and the maximum value of 10; that is, all subranges beginning with a minimum value of 1 or more, (e.g. 1 to 6.1), and ending with a maximum value of 10 or less, (e.g. 2.3 to 9.4, 3 to 8, 4 to 7), and finally to each number 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 contained within the range.
This completes the description of the preferred and alternate embodiments of the invention. Those skilled in the art may recognize other equivalents to the specific embodiment described herein which equivalents are intended to be encompassed by the claims attached hereto.

Claims

Claims
1. A method of reducing the amount of hydrogen sulfide in a hydrocarbon fluid by contacting that fluid with an effective amount of a composition comprising a hydrogen sulfide scavenger, wherein the amount of hydrogen sulfide scavenger is sufficient to react with the hydrogen sulfide to reduce the hydrogen sulfide found in the vapor phase., the reaction product of the hydrogen sulfide scavenger and the hydrogen sulfide remain soluble in the hydrocarbon fluid, the hydrogen sulfide scavenger contains at least one alpha-amino ether.
2. The method of claim 1 wherein the composition includes one item selected from the list consisting of:
N,N'-oxybis(methylene)bis(N,N-dibutylamine),
N,N'-(methylenebis(oxy)bis(methyIene))bis(N,N-dibutylamine),
and any combination thereof that may include Ν,Ν,Ν'Ν'-tetrabutylmethanediamine.
3. The method of claim 1 in which the reaction product of the sulfide scavenging formulation and the hydrogen sulfide do not form a separate fluid layer.
4. The method of claim 1 further comprising the step of reacting a secondary amine with a formaldehyde equivalent to form at least some of the scavenging formulation.
EP20110807425 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons Ceased EP2593535A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/836,037 US20120012507A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
PCT/US2011/043793 WO2012009396A2 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons

Publications (2)

Publication Number Publication Date
EP2593535A2 true EP2593535A2 (en) 2013-05-22
EP2593535A4 EP2593535A4 (en) 2014-04-23

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KR (1) KR20130047739A (en)
CN (1) CN103403129B (en)
AR (1) AR082165A1 (en)
BR (1) BR112013000890A2 (en)
CA (1) CA2805404C (en)
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RU (1) RU2563633C2 (en)
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