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CN103403129B - 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 Download PDF

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Publication number
CN103403129B
CN103403129B CN201180034667.8A CN201180034667A CN103403129B CN 103403129 B CN103403129 B CN 103403129B CN 201180034667 A CN201180034667 A CN 201180034667A CN 103403129 B CN103403129 B CN 103403129B
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Prior art keywords
hydrogen sulfide
alpha
scavenger
fluid
hydrocarbon fluid
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CN201180034667.8A
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Chinese (zh)
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CN103403129A (en
Inventor
D·R·康普顿
J·拜伦·斯特里克兰
胡安·M·加西亚三世
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ChampionX LLC
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Ondeo Nalco Co
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Gas Separation By Absorption (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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

Alpha-amino group ether is used for the purposes removing hydrogen sulfide from hydrocarbon
The cross reference of related application
Nothing
About the research of federal government-funded or the statement of exploitation
Inapplicable
Background of invention
The present invention relates generally to the acid carburet hydrogen of process and liquid hydrocarbon with the hydrogen sulfide removed in it or the level of hydrogen sulfide reduced in it.The toxicity of the hydrogen sulfide in hydrocarbon fluid (hydrocarbon fluid) is in industry well-known.This makes take sizable cost every year and make great efforts the content of hydrogen sulfide to be reduced to safe level.
In big production plants, more economical is install regeneration system rapidly to process acid gas stream usually.These systems adopt the compound used in absorption tower to contact produced fluid and optionally absorbing hydrogen sulphide and other possible toxicants, such as carbonic acid gas and mercaptan usually.Absorption compound regenerates subsequently and is again used in system.Usually, hydrogen sulfide absorption material other materials of comprising alkanolamine, PEG, hindered amine and can regenerating.
Non-renewable scavenging agent for the hydrogen sulfide removal of packaged unit is divided into four general classifications: 1) based on aldehyde, 2) based on metal oxide, 3) based on caustic alkali and 4) other techniques.By non-renewable compound in the removal of hydrogen sulfide, scavenging agent and hydrogen sulfide react the compound generating nonlethal compound or can remove from hydrocarbon.Such as, when aldehyde and hydrogen sulfide react, the compound being called formthionals (as trithian) is defined.
The aldehyde scavenging agent of prior art generally includes low-molecular-weight aldehyde and ketone and adducts thereof.Low-molecular-weight aldehyde can also be combined with alkyl or alkanolamine, as United States Patent (USP) the 4th, disclosed in 748, No. 011.The scavenging agent that other aldehyde derive comprises the reaction product of lower molecular weight alkanolamine and aldehyde, as United States Patent (USP) the 4th, disclosed in 978, No. 512.PCT application WO 92/01481 discloses a kind of some trisubstituted six hydrogen-s-triazine that use to reduce the method for the sulfide in different application.German document DE4027300 discloses a kind of for removing H 2the regenerated solvent of S and mercaptan.United States Patent (USP) the 5th, 347, No. 004 discloses 1,3, the purposes of 5 alkoxyalkylene Hexahydrotriazines.PCT application WO 91 US 5232 disclose hydroxyalkyl triazine scavenging agent, particularly N, N ', N "-three (2-hydroxyethyl) six hydrogen-s-triazine.United States Patent (USP) the 5th, 774, No. 024 combination disclosing alkyl triazine scavenging agent and quaternary ammonium salt, wherein quaternary ammonium salt enhances effect of alkyl triazine.But, the trial of these prior aries normally aqueous-based chemistries and need fully mixing to allow scavenging agent effectively contact hydrocarbon fluid and remove hydrogen sulfide.
Thus, obviously there is the demand of improving one's methods and the application to using the scavenging agent dissolved in pending hydrocarbon fluid to remove hydrogen sulfide from this fluid.It is admitting of " prior art " relative to the present invention that technology described by this part is not intended to form any patent quoted herein, announcement or other information, represents unless specifically so.In addition, this part should not be interpreted as meaning to have carried out retrieving or do not exist other relevant informations defined in 37 CFR § 1.56 (a).
Summary of the invention
At least one embodiment of the present invention relates to a kind of method for removing hydrogen sulfide from hydrocarbon fluid.The method comprises makes described fluid contact with the composition comprising hydrogen sulfide scavenger of significant quantity.The amount of hydrogen sulfide scavenger is enough to the amount reacting to reduce the hydrogen sulfide be discharged in the vapour space (vaporspace) with hydrogen sulfide.The reaction product of hydrogen sulfide scavenger and hydrogen sulfide keeps solvable in hydrocarbon fluid.Hydrogen sulfide scavenger comprises at least one alpha-amino group ether.
Composition can comprise one that is selected from by the following list formed:
N, N ' two (methylene radical) two (N, the N-dibutylamine) of-oxygen,
N, N '-(methylene-bis (oxygen) two (methylene radical)) two (N, N-dibutylamine),
And arbitrary combination.
The reaction product that sulfide removes preparation and hydrogen sulfide can not form independent stream layer.The method can further include following step: secondary amine and formaldehyde equivalent are reacted generate at least some to remove preparation.Hydrocarbon fluid can be liquid.
Detailed Description Of The Invention
Based on the object of the application, shown in these terms are defined as follows:
" alpha-amino group ether " means the molecule according to following formula:
Wherein: R 1, R 2, R 3, R 4be the carbon containing side chain containing 1-20 carbon atom, and comprise ring compound and acyclic compound.Ring compound can be aromatics or non-aromatic.Example includes but not limited to methyl, ethyl, propyl group, the tertiary butyl, cyclopentyl, cyclohexyl, morpholino and phenyl and they can be identical group or one or more different groups.B is ether, and it can be Sauerstoffatom or the group (such as-OCH all at two ends with Sauerstoffatom 2o-or OC 2h 4o-).
" formaldehyde equivalent " means to comprise according to formula: (CH 2o) nthe material composition of at least one group, wherein n be more than or equal to 1 integer, and/or comprise the material composition of formaldehyde or associated molecule such as paraformaldehyde and/or s-trioxane.
" hydrocarbon fluid " means the liquid or the gas that consist predominantly of machine material, and described organic materials includes but not limited to kerosene, crude oil, emulsion of crude oil, field condensate (oilfield condensate), petroleum residual oil, refined fuels, distillate fuel, oil fuel, heating oil, diesel oil, gasoline, jet engine fuel, marine fuel oil and any combination thereof.
" non-renewable scavenging agent " means the scavenging agent consumed by scavenging process.
" regeneration scavenging agent " means to can't help the scavenging agent that scavenging process consumes.
" scavenging agent " means to can be used for reduce such as, but not limited to the amount of some other material composition of hydrogen sulfide or the material composition of effect alleviating these compositions in fluid medium, such as, but not limited to alpha-amino group ether.
If above-mentioned definition or in other descriptions mentioned Anywhere of the application and the implication in normally used implication, dictionary or be incorporated in the application described in data implication by reference (clear and definite or in secret) is inconsistent, term so in the application and claim especially should be understood to explain according to the definition in the application and describing, instead of explains according to the definition of conventional definition, dictionary or the definition that is incorporated to by reference.In view of above, if term only can be understood according to the explanation of dictionary, if term is by Kirk-Othmer Encyclopedia of Chemical Technology, 5th edition, (2005), (by Wiley, John & Sons, Inc. publish) define, so how this term of control is defined by this definition in the claims.
In at least one embodiment, the hydrogen sulfide in hydrocarbon fluid reduces by being incorporated in described fluid by alpha-amino group ether scavenging agent.
In at least one embodiment, alpha-amino group ether is a part for the removing preparation used in hydrocarbon fluid.Preparation comprises alpha-amino group ether and can also be made up of carrier fluid.Preparation can be introduced in hydrocarbon fluid by mechanism, and described mechanism includes but not limited to any mechanism disclosed in syringe pump or United States Patent (USP) the 5th, 774, No. 024 and the 5th, 840, No. 177.Under the background of hydrocarbon gas fluid, gas can be made to pass through to contain the absorption tower of removing preparation.
The advantage using alpha-amino group ether scavenging agent to compare other scavenging agents is that alpha-amino group ether scavenging agent is dissolved in hydrocarbon fluid, and reason is alpha-amino group ether is not water based product.
As shown in Figure 1, at least one embodiment, hydrogen sulfide scavenger is reacted by secondary amine and formaldehyde or other formaldehyde equivalent such as paraformaldehyde or s-trioxane and is produced.This generates the material composition of the alpha-amino group ether (compd B and Compound C) mainly comprising two kinds of forms.The 10%-25% of composition is single oxygen ether (compd B) and the 50%-80% of composition is the dioxygen ether (Compound C) between ether oxygen with single carbon atom.Reaction product also comprises the non-ether diamine (compd A) of 10-25%.Compd A is the inevitable by product of reaction mixture.Reaction can be undertaken by mixed reactant in a solvent, and solvent is such as, but not limited to petroleum naphtha (oil) heavy aromatic solvent (Aromatic 150 of such as ExxonMobil and Solvesso) or petroleum naphtha light aromatic solvent (Aromatic 100 of such as Americhem Sales Corporation).
In at least one embodiment, in reaction mixture the ratio of amine and formaldehyde in the scope of 1.5: 1 to 1: 1.5 (comprising end points) and preferably between 1.2: 1 to 1: 1.2.
In at least one embodiment, any one in R and R ' group corresponds to the radicals R described in the definition of " alpha-amino group ether " 1, R 2, R 3, R 4in any one.
In at least one embodiment, when R is normal-butyl and R ' is H, so:
Compd A is N, N, N ', N '-tetrabutyl methane diamines,
Compd B is N, N '-oxygen two (methylene radical) two (N, N-bis-butylidene), and
Compound C is N, N '-(methylene-bis (oxygen) two (methylene radical)) two (N, N '-dibutylamine).
Removing composition contemplated by least some comprises containing following preparation:
(compd A, B and C), (A and B), (A and C), (B and C), (only C) and (only B).
Embodiment
Foregoing teachings can be understood better by reference to the following examples, provide embodiment to be object in order to explain instead of be intended to limit the scope of the invention.
Test the sample of hydrocarbon fluid to determine effect of scavenging agent.Table 1 compares composition of the present invention at 22 DEG C in petroleum naphtha, table 2 be at 22 DEG C in kerosene and table 3 be at 97 DEG C in slurry oil (slurry oil of the clarification produced in such as carbon black oil, decanted oil and refinery).Sample comprises the hydrogen sulfide of change level and comparatively carries out processing or keep untreated with the alpha-amino group ether scavenging agent of various dose, and records the H reduced in each sample 2the amount of S.
Table 1: petroleum naphtha 22 DEG C
Table 2: kerosene 22 DEG C
Table 3: slurry oil 97 DEG C
The H existed in the vapour space is determined by the hydrogen sulfide levels measuring the vapour space according to ASTM D5705-03 2the amount of S.Test process is changed by running at the temperature of non-60 DEG C.The sample sample of 1 gallon being divided into multiple 500 milliliters is used for test.The container processed is by pre-loaded compd A-C, and fluid then to be tested is dumped in this container.
In each example, dose ratio is the numerical value of the ppm processing rate for determining sample.His-and-hers watches 1, untreated sample produces the hydrogen sulfide observed value of 800ppm in the vapour space.The dose ratio of 0.2 represents the additive treating sample with 160ppm.The dose ratio of 0.3 represents the additive treating sample with 240ppm.
These data show that the existence of sample alpha-amino group ether scavenging agent decreases the H in hydrocarbon fluid in relatively short time quantum 2s and to be exposed to time of alpha-amino group ether before test longer, continues to reduce H 2s.
Although the present invention can be presented as many different forms, shown in the drawings and describe concrete preferred embodiment of the present invention in this article in detail.Present disclosure is the example of the principle of the invention and is not intended to limit the invention to explained particular.Mention all patents, patent application, scientific paper and any other reference material to be herein incorporated to by reference of text at this.In addition, the present invention includes any possible combination of some or all of different embodiments that is described herein and that be incorporated to herein.
Above-mentioned disclosure be intended that illustrative and be not exhaustively.This description expects many changes and possibility by making those skilled in the art.All these possibilities and change intention are included within the scope of the claims, and wherein term " comprises " and meaning " including, but are not limited to ".Those skilled in the art will recognize that other equivalents of specific embodiments described herein, this equivalent is also intended to included by claim.
All scopes disclosed herein and parameter are understood to include the every number between wherein comprised any and all subranges and end points.Such as, the scope " 1 to 10 " stated should be believed to comprise any and all subranges of (and comprising 1 and 10) between minimum value 1 and maximum value 10; Namely, with minimum value 1 or larger beginning (as, 1 to 6.1) and with (as 2.3 to 9.4,3 to 8,4 to 7) all subranges of maximum value 10 or less end, and be finally each number 1,2,3,4,5,6,7,8,9 and 10 comprised within the scope of this.
This accomplishes the description of preferred and selectable embodiment of the present invention.Those skilled in the art will recognize that other equivalents of specific embodiments described herein, this equivalent intention is by investing included by this claim.

Claims (4)

1. one kind for reducing the method for the amount of the hydrogen sulfide in hydrocarbon fluid, described method contacts with the composition comprising hydrogen sulfide scavenger of significant quantity by making this fluid, wherein the amount of hydrogen sulfide scavenger is enough to react to reduce the hydrogen sulfide existed in the vapour space with hydrogen sulfide, the reaction product of described hydrogen sulfide scavenger and described hydrogen sulfide keeps solvable in described hydrocarbon fluid, and described hydrogen sulfide scavenger comprises at least one alpha-amino group ether.
2. the method for claim 1, wherein said composition comprises one that is selected from by the following list formed:
N, N ' two (methylene radical) two (N, the N-dibutylamine) of-oxygen,
N, N '-(methylene-bis (oxygen) two (methylene radical)) two (N, N-dibutylamine),
And can N be comprised, N, N ', the arbitrary combination of N '-tetrabutyl methane diamines.
3. the method for claim 1, the described reaction product that wherein said sulfide removes preparation and described hydrogen sulfide does not form independent stream layer.
4. the method for claim 1, also comprises the steps: that secondary amine and formaldehyde equivalent are reacted and generates at least some to remove preparation.
CN201180034667.8A 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons Active CN103403129B (en)

Applications Claiming Priority (3)

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

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CN103403129B true CN103403129B (en) 2015-05-20

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AR (1) AR082165A1 (en)
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CA (1) CA2805404C (en)
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US9638018B2 (en) * 2012-12-19 2017-05-02 Ecolab Usa Inc. Scavenging hydrogen sulfide
WO2014100051A1 (en) 2012-12-19 2014-06-26 Nalco Company Squeeze treatment for in situ scavenging of hydrogen sulfide
US9523045B2 (en) 2013-01-30 2016-12-20 Ecolab Usa Inc. Hydrogen sulfide scavengers
US9663390B2 (en) 2013-05-10 2017-05-30 Ecolab Usa Inc. Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product
WO2014210166A1 (en) 2013-06-27 2014-12-31 Ecolab Usa Inc. Epoxide-based hydrogen sulfide scavengers
US9273254B2 (en) 2013-12-20 2016-03-01 Ecolab Usa Inc. Amino acetals and ketals as hydrogen sulfide and mercaptan scavengers
US9458393B2 (en) 2014-04-15 2016-10-04 Ecolab Usa Inc. Hydantoins as hydrogen sulfide and mercaptan scavengers
US10308886B2 (en) 2015-04-22 2019-06-04 Ecolab Usa Inc. Development of a novel high temperature stable scavenger for removal of hydrogen sulfide
CA2997416C (en) 2015-09-08 2023-06-27 Ecolab Usa Inc. Hydrogen sulfide scavengers
US10513662B2 (en) 2017-02-02 2019-12-24 Baker Hughes, A Ge Company, Llc Functionalized aldehydes as H2S and mercaptan scavengers
JPWO2018207657A1 (en) 2017-05-12 2020-05-21 株式会社クラレ Sulfur-containing compound removal device and sulfur-containing compound removal method
WO2018218641A1 (en) * 2017-06-02 2018-12-06 General Electric Company Method of mitigation of tramp amines in application of h2s scavengers
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WO2020154251A1 (en) 2019-01-23 2020-07-30 Ecolab Usa Inc. Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a michael acceptor
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WO2012009396A2 (en) 2012-01-19
JP5890409B2 (en) 2016-03-22
EP2593535A2 (en) 2013-05-22
AR082165A1 (en) 2012-11-14
KR20130047739A (en) 2013-05-08
MX2013000507A (en) 2013-02-27
CA2805404C (en) 2018-11-27
CN103403129A (en) 2013-11-20
RU2013102414A (en) 2014-08-20
BR112013000890A2 (en) 2016-05-17
US20120012507A1 (en) 2012-01-19
SG187078A1 (en) 2013-02-28
RU2563633C2 (en) 2015-09-20
JP2013531728A (en) 2013-08-08
EP2593535A4 (en) 2014-04-23
WO2012009396A3 (en) 2012-05-18

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