WO2010027353A1 - Process for removing hydrogen sulfide in crude oil - Google Patents

Process for removing hydrogen sulfide in crude oil Download PDF

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Publication number
WO2010027353A1
WO2010027353A1 PCT/US2008/075030 US2008075030W WO2010027353A1 WO 2010027353 A1 WO2010027353 A1 WO 2010027353A1 US 2008075030 W US2008075030 W US 2008075030W WO 2010027353 A1 WO2010027353 A1 WO 2010027353A1
Authority
WO
WIPO (PCT)
Prior art keywords
crude oil
weight
hydrogen sulfide
chloride
percent
Prior art date
Application number
PCT/US2008/075030
Other languages
English (en)
French (fr)
Inventor
Lawrence John Karas
Alan E. Goliaszewski
Original Assignee
General Electric Company
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 General Electric Company filed Critical General Electric Company
Priority to CN2008801310239A priority Critical patent/CN102144019A/zh
Priority to MX2011002377A priority patent/MX2011002377A/es
Priority to RU2011107198/04A priority patent/RU2499031C2/ru
Priority to BRPI0808265A priority patent/BRPI0808265A2/pt
Priority to CA2735429A priority patent/CA2735429A1/en
Priority to PCT/US2008/075030 priority patent/WO2010027353A1/en
Priority to US13/061,290 priority patent/US20110155646A1/en
Publication of WO2010027353A1 publication Critical patent/WO2010027353A1/en
Priority to EC2011010860A priority patent/ECSP11010860A/es

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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

Definitions

  • This invention relates generally to methods for removing hydrogen sulfide and more particularly, to removing hydrogen sulfide from crude oil.
  • Crude oil may contain hydrogen sulfide, which is highly corrosive in the presence of water and poisonous in very small concentrations.
  • the risk of exposure to hydrogen sulfide from handling crude oil is a health and safety concern during storage, transportation (shipping, truck or pipeline) and processing of the crude oil.
  • Hydrogen sulfide scavengers are used to remove hydrogen sulfide from the crude oil.
  • Typical hydrogen sulfide scavengers are triazines and aldehydes.
  • triazines release amines into the liquid hydrocarbon media and residual triazines thermally decompose to release additional amines into the liquid hydrocarbon media and may pose additional health concerns.
  • the free amines can form salts, which deposit on the processing equipment and cause corrosion.
  • Aldehydes can have slower reaction kinetics and may have incomplete hydrogen sulfide scavenging. What is needed is an improved scavenger for removing hydrogen sulfide from crude oil.
  • a method for reducing the amount of hydrogen sulfide present in crude oil includes adding a hydrogen sulfide scavenger composition to the crude oil to capture the hydrogen sulfide, migrating the captured sulfides to an aqueous phase and removing the aqueous phase from the crude oil, wherein the hydrogen sulfide scavenger composition includes glyoxal and a quaternary ammonium salt.
  • the various embodiments provide an improved hydrogen scavenging process for crude oil that quickly captures hydrogen sulfide and does not generate amine byproducts.
  • a method for reducing the amount of hydrogen sulfide present in crude oil includes adding a hydrogen sulfide scavenger composition to the crude oil to capture the hydrogen sulfide, migrating the captured sulfides to an aqueous phase and removing the aqueous phase from the crude oil, wherein the hydrogen sulfide scavenger composition includes glyoxal and a quaternary ammonium salt.
  • the crude oil may be any type of crude oil containing hydrogen sulfide. Any amount of hydrogen sulfide in the crude oil may be reduced and the actual amount of residual hydrogen sulfide will vary depending on the starting amount.
  • the hydrogen sulfide levels are reduced to 150 ppm by weight or less, as measured in the vapor phase, based on the weight of the crude oil. In another embodiment, the hydrogen sulfide levels are reduced to 100 ppm by weight or less, as measured in the vapor phase, based on the weight of the crude oil. In another embodiment, the hydrogen sulfide levels are reduced to 50 ppm by weight or less, as measured in the vapor phase, based on the weight of the crude oil. In another embodiment, the hydrogen sulfide levels are reduced to 20 ppm by weight or less, as measured in the vapor phase, based on the weight of the crude oil.
  • the hydrogen sulfide scavenger composition is added to the crude oil in any conventional manner.
  • the scavenger composition is injected into the crude oil by a conventional in-line injection system and may be injected at any point inline suitable to allow the scavenger to mix with the crude oil, such as in a pipeline or in a tanker.
  • the scavenger composition can be added to the crude oil in a continuous manner or can be added in one or more batch modes and repeated additions may be made.
  • the scavenger composition is added to the crude oil in any amount sufficient to reduce the levels of hydrogen sulfide in the crude oil.
  • the scavenger composition is added in an amount of from about 1 ppm to about 3000 ppm by weight, based on the weight of the crude oil.
  • the scavenger composition is added in an amount of from about 10 ppm by weight to about 2000 ppm by weight, based on the weight of the crude oil.
  • the scavenger composition is added in an amount of from about 50 ppm by weight to about 1500 ppm by weight, based on the weight of the crude oil.
  • the scavenger composition is added in an amount of from about 100 ppm by weight to about 1200 ppm by weight, based on the weight of the crude oil.
  • the hydrogen sulfide scavenger may be added neat or diluted with water or solvent and may be formulated or blended with other suitable materials or additives.
  • the hydrogen sulfide scavenger composition captures and neutralizes hydrogen sulfide in the crude oil by incorporating the sulfur into an inert ringed compound.
  • the ringed compound is non-hazardous and is attracted to a water phase and migrates to a water phase away from an oil phase.
  • the hydrogen sulfide scavenger composition comprises glyoxal and a quaternary ammonium compound.
  • Glyoxal is a water-soluble aldehyde and may include oligomers of glyoxal. Glyoxal is commercially available.
  • the glyoxal is catalyzed with a quaternary ammonium salt, which improves the efficacy of the scavenger composition and enhances removal of hydrogen sulfide.
  • the catalyst may be any suitable quaternary ammonium salt. In one embodiment, the catalyst has formula I:
  • Ri, R 2 , R 3 and R 4 are each independently an alkyl group having from 1 to 30 carbon atoms, an aryl group having from 6 to 30 carbon atoms or an arylalkyl group having from 7 to 30 carbon atoms; and X is a halide, sulfate, nitrate or carboxylate.
  • the alkyl groups and the aryl groups may be substituted or unsubstituted.
  • R 1 is an alkyl group having from 1 to 24 carbon atoms.
  • R 2 is an alkyl having from 1 to 24 carbon atoms, an aryl group having from 6 to 24 carbon atoms or an arylalkyl group having from 7 to 24 carbon atoms.
  • R 3 and R 4 are each, independently, an alkyl group having from 1 to 24 carbon atoms. In another embodiment, R 3 and R 4 are each, independently, an alkyl group having from 1 to 4 carbon atoms.
  • the alkyl group includes, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, decyl or dodecyl.
  • the aryl group may be phenyl.
  • the arylalkyl group include may be benzyl.
  • the halide may be chloride, bromide or iodide.
  • the sulfate may be a methyl sulfate.
  • the nitrate may be a bisulfate nitrate.
  • the carboxylate may be acetate.
  • the quaternary ammonium salt is alkyl benzyl ammonium chloride or benzyl cocoalkyl (C 12 -C 18 ) dimethylammonium chloride.
  • the quaternary ammonium salt includes, but is not limited to dicocoalkyl (C 12 -C 18 ) dimethylammonium chloride, ditallowdimethylammonium chloride, di(hydrogenated tallow alkyl) dimethyl quaternary ammonium methyl chloride, methyl bis (2-hydroxyethyl cocoalkyl (C 12 -C 18 ) quaternary ammonium choride, dimethyls- ethyl) tallow ammonium methyl sulfate, n-dodecylbenzyldimethylammonium chloride, n- octadecylbenzyldimethyl ammonium chloride, n-dodecyltrimethylammonium sulfate
  • the quaternary ammonium salt is present from about 0.01 to about 15 percent by weight based on the amount of glyoxal. In another embodiment, the quaternary ammonium salt is present from about 1 to about 10 percent by weight based on the amount of glyoxal.
  • the scavenger composition is attracted to an aqueous phase and the captured sulfides will migrate into an aqueous phase. If an emulsion is present, the captured sulfides can be migrated into the aqueous phase from the crude oil and removed with the aqueous phase. If no emulsion is present, a water wash can be added to attract the captured sulfides.
  • the hydrogen sulfide scavenger composition is added before the crude oil is treated in a desalter, which emulsifies the hydrocarbon media with a water wash to extract water soluble contaminants and separates and removes the water phase from the crude oil.
  • a water wash is added in an amount suitable for forming an emulsion with the crude oil.
  • the water wash is added in an amount of from about 1 to about 50 percent by volume based on the volume of the emulsion.
  • the wash water is added in an amount of from about 1 to about 25 percent by volume based on the volume of the emulsion.
  • the wash water is added in an amount of from about 1 to about 10 percent by volume based on the volume of the emulsion.
  • the amount of crude oil is present in an amount of from about 50 to about 99 percent by volume based on the volume of the emulsion.
  • the crude oil is present in an amount of from about 75 to about 99 percent by volume based on the volume of the emulsion. In another embodiment, the crude oil is present in an amount of from about 90 to about 99 percent by volume based on the volume of the emulsion.
  • the water wash and crude oil are emulsified by any conventional manner. In one embodiment, the water wash and crude oil are heated and thoroughly mixed to produce an oil-in- water emulsion. In one embodiment, the water wash and crude oil are heated at a temperature in a range of from about 90 0 C to about 150 0 C.
  • the water wash and crude oil are mixed in any conventional manner, such as an in-line static mixer or an in-line mix valve with a pressure drop of about 0.2 to about 2 bar depending on the density of the crude oil.
  • the emulsion is allowed to separate, such as by settling, into an aqueous phase and an oil phase.
  • the aqueous phase is removed.
  • the aqueous phase is removed by draining the aqueous phase.
  • Demulsifiers may be added to aid in separating the water from the crude oil.
  • the demulsifiers include, but are not limited to, oxyalkylated organic compounds, anionic surfactants, nonionic surfactants or mixtures of these materials.
  • the oxyalkylated organic compounds include, but are not limited to, phenolformaldehyde resin ethoxylates, alkoxylated polyols and amines, such as Pluronic ® block co-polymers.
  • the anionic surfactants include alkyl or aryl sulfonates, such as dodecylbenzenesulfonate.
  • demulsifiers may be added in amounts to contact the water from about 1 to about 1000 ppm by weight based on the weight of the crude oil. Combinations of additives may be used, but the total amounts of additives added should be in the range of from about 1 to about 1000 ppm by weight based on the weight of the crude oil.
  • Hydrogen sulfide scavenging tests were performed on a crude oil containing 500 ppm hydrogen sulfide in the liquid phase from a Texas refinery in Valero. Testing was performed using the modified ASTM 5705-95 test that measures vapor phase H 2 S two hours after treatment (140 0 F) via dragger tube. Results are shown in Table 1.
  • MEA is monoethanol amine
  • 2Triazine 8411C is available commercially from Clearwater, Inc as Sulfa-Clear 8411C.
  • 3MMA is monomethyl amine
  • Catalyst is cocoalkyldimethylbenzyl ammonium chloride (Arquad ® DMCB-80) at 1.6% by weight treatment level (actives basis) based on the weight of the triazine or glyoxal.
  • Sample 1 has comparable results to the use of a triazine in reducing hydrogen sulfide, but the catalyzed glyoxal can be removed in an aqueous phase; whereas, the triazine remains with the oil and can generate amines upon further processing.
  • the catalyzed glyoxal sample shows significant improvement over glyoxal; whereas, catalyzing the triazine does not improve the performance of the triazine..
  • the concentration of the hydrogen sulfide in the vapor phase was determined at different levels of treatment dosages after 1 hour and 2 hours for samples 1 and comparative examples CE-I and CE-3, as shown in Table 2.
  • Table 2 The concentration of the hydrogen sulfide in the vapor phase was determined at different levels of treatment dosages after 1 hour and 2 hours for samples 1 and comparative examples CE-I and CE-3, as shown in Table 2.
  • Sample 1 reduce and control the hydrogen sulfide level.
  • Sample 1 has comparable results to CE-I and CE-3. However, Sample 1 can be removed in an aqueous phase and does not generate amines like the triazine samples will.
  • a demulsif ⁇ er was added to the H 2 S-infused crude oil in the amounts shown in Table 3.
  • wash water 5% by volume wash water was mixed with glyoxal and cocoalkyldimethylbenzyl ammonium chloride, as shown in Table 3, and added to the H 2 S-infused crude oil.
  • the wash water was mixed with the H 2 S-infused crude oil at 4000 rpm for 2 seconds, grids on, and heated to 130 0 C at a pressure of 4 psi to form an emulsion.
  • the emulsion was allowed to sit for 32 minutes to separate the water phase from the crude oil. A water drop reading was performed to test the emulsion separation and is shown in Table 4. The water phase was removed from the separated emulsion and observed for clarity as shown in Table 3.
  • Demulsif ⁇ er is an alkoxylated alkylphenol formaldehyde available commercially from General Electric Company. 2Doses based on 100 ml total volume.
  • Treatment is glyoxal and cocoalkyldimethylbenzyl ammonium chloride at 1.6% by weight treatment level (actives basis) based on the weight of the glyoxal.
  • the increasing cloudiness in the separated water at higher levels of hydrogen sulfide treatment indicates the presence of captured hydrogen sulfide products that were removed with the water. Also, the hydrogen sulfide scavenger does not negatively impact the separation of the emulsion.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
PCT/US2008/075030 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil WO2010027353A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CN2008801310239A CN102144019A (zh) 2008-09-02 2008-09-02 用于从原油中去除硫化氢的方法
MX2011002377A MX2011002377A (es) 2008-09-02 2008-09-02 Procedimiento para remover sulfuro de hidrogeno en petroleo crudo.
RU2011107198/04A RU2499031C2 (ru) 2008-09-02 2008-09-02 Способ удаления сероводорода из сырой нефти
BRPI0808265A BRPI0808265A2 (pt) 2008-09-02 2008-09-02 "método para reduzir a quantidade de sulfeto de hidrogênio presente em óleo bruto"
CA2735429A CA2735429A1 (en) 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil
PCT/US2008/075030 WO2010027353A1 (en) 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil
US13/061,290 US20110155646A1 (en) 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil
EC2011010860A ECSP11010860A (es) 2008-09-02 2011-03-02 Proceso para remover sulfuro de hidrogeno en petroleo crudo

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2008/075030 WO2010027353A1 (en) 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil

Publications (1)

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WO2010027353A1 true WO2010027353A1 (en) 2010-03-11

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PCT/US2008/075030 WO2010027353A1 (en) 2008-09-02 2008-09-02 Process for removing hydrogen sulfide in crude oil

Country Status (8)

Country Link
US (1) US20110155646A1 (zh)
CN (1) CN102144019A (zh)
BR (1) BRPI0808265A2 (zh)
CA (1) CA2735429A1 (zh)
EC (1) ECSP11010860A (zh)
MX (1) MX2011002377A (zh)
RU (1) RU2499031C2 (zh)
WO (1) WO2010027353A1 (zh)

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EP2593535A2 (en) * 2010-07-14 2013-05-22 Nalco Company Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
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US9752083B2 (en) 2012-08-21 2017-09-05 Lonza, Inc. Method of scavenging hydrogen sulfide and/or sulfhydryl compounds
RU2532019C1 (ru) * 2013-07-30 2014-10-27 Ахматфаиль Магсумович Фахриев Реагент для нейтрализации сероводорода и подавления роста сульфатвосстанавливающих бактерий

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ECSP11010860A (es) 2011-04-29
RU2011107198A (ru) 2012-10-10
CN102144019A (zh) 2011-08-03
US20110155646A1 (en) 2011-06-30
CA2735429A1 (en) 2010-03-11
BRPI0808265A2 (pt) 2019-09-24
RU2499031C2 (ru) 2013-11-20
MX2011002377A (es) 2011-09-21

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