US20190241822A1 - Composition for removing iron sulfide - Google Patents

Composition for removing iron sulfide Download PDF

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Publication number
US20190241822A1
US20190241822A1 US16/312,363 US201716312363A US2019241822A1 US 20190241822 A1 US20190241822 A1 US 20190241822A1 US 201716312363 A US201716312363 A US 201716312363A US 2019241822 A1 US2019241822 A1 US 2019241822A1
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group
iron sulfide
methyl
composition
carbon atoms
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Abandoned
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US16/312,363
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Inventor
Masaki Shimizu
Yuusuke SAITOU
Takuo Tsuruta
Junichi Fuji
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Kuraray Co Ltd
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Kuraray Co Ltd
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Assigned to KURARAY CO., LTD. reassignment KURARAY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TSURUTA, TAKUO, SAITOU, Yuusuke, FUJI, JUNICHI, SHIMIZU, MASAKI
Publication of US20190241822A1 publication Critical patent/US20190241822A1/en
Abandoned legal-status Critical Current

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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
    • C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
    • C10G75/02—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of corrosion inhibitors
    • 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
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/16—Oxygen-containing compounds
    • 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
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
    • 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
    • C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
    • C10G29/24—Aldehydes or ketones
    • 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
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G9/14—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils in pipes or coils with or without auxiliary means, e.g. digesters, soaking drums, expansion means
    • C10G9/16—Preventing or removing incrustation
    • 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/24—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions
    • 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents

Definitions

  • the present invention relates to a composition for removing iron sulfide and a method for removing iron sulfide, which includes using the same.
  • Hydrogen sulfide that often exists in hydrocarbons, such as fossil fuels and refined petroleum products, for example, natural gas, liquefied natural gas, sour gas, crude oil, naphtha, heavy aromatic naphtha, gasoline, kerosene, diesel oil, light oil, heavy oil, FCC slurry, asphalt, and oil field concentrates, corrodes iron which is used in excavation facilities, etc., to cause generation of iron sulfide.
  • the iron sulfide is accumulated as a deposit within production facilities of fossil fuels and refined petroleum products, to lower operational efficiency of instruments in heat exchanger, cooling tower, reactor, transmission pipeline, furnace, etc., or disturb precise measurement for facility maintenance, and therefore, it is desired to remove this.
  • the acrolein is a compound which is strongly toxic and whose concentration is strictly regulated from the viewpoint of occupational safety and from the viewpoint of environmental safety, so that it involves such a problem that attention is required for handling.
  • the acrolein is problematic from the viewpoint that it is extremely easily polymerized and lacks in thermal stability and also from the viewpoint that it lacks in pH stability, so that its abundance gradually decreases depending upon the pH of the environment to be used.
  • an object of the present invention is to provide a composition containing an active ingredient with high thermal stability and pH stability and being capable of removing iron sulfide safely and efficiently.
  • aldehyde (1) A composition for removing iron sulfide, containing, as an active ingredient, an ⁇ , ⁇ -unsaturated aldehyde represented by the following general formula (1) (hereinafter referred to as “aldehyde (1)”);
  • R 1 to R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, provided that R 1 may be connected to R 2 or R 3 , to constitute an alkylene group having 2 to 6 carbon atoms; and that R 1 and R 2 are not a hydrogen atom at the same time.
  • [2] The composition of [1], wherein R 1 to R 3 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. [3] The composition of [1] or [2], wherein R 3 is a hydrogen atom. [4] A method for removing iron sulfide, including bringing the composition of any of [1] to [3] into contact with iron sulfide. [5] The method of [4], wherein the aldehyde (1) in the composition is added in an amount of 0.1 to 100 parts by mass based on 1 part by mass of iron sulfide.
  • composition of the present invention contains the aldehyde (1), an excellent removal performance of iron sulfide is exhibited.
  • the composition of the present invention has such an advantage that it is extremely low in toxicity and high in thermal stability and pH stability. Though the reasons for this are not elucidated yet, it may be considered as one of factors that since the aldehyde (1) has at least one of an alkyl group, an alkenyl group, and an aryl group at the ⁇ -position thereof, an addition reaction to the ⁇ -position of a bulky molecule, such as a biomolecule and a propagating chain, is hard to occur as compared with acrolein not having a substituent at the ⁇ -position thereof.
  • the aldehyde (1) comes to bond to hydrogen sulfide that is existent in an equilibrium state with iron sulfide to thereby remove hydrogen sulfide, dissolution of iron sulfide is promoted, and as a result, the iron sulfide is removed; and while the aldehyde (1) has a substituent at the ⁇ -position thereof, an attack from hydrogen sulfide that is in general a small molecule is not hindered so much, whereby the removal performance of iron sulfide is kept.
  • FIG. 1 is a graph showing pH stability of senecioaldehyde (SAL).
  • FIG. 2 is a graph showing pH stability of acrolein.
  • composition of the present invention includes the aldehyde (1) as an active ingredient.
  • the alkyl group having 1 to 10 carbon atoms, which R 1 to R 3 each independently represent, may be linear, branched, or cyclic, and examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-octyl group, a n-decyl group, a n-dodecyl group, and a cyclopentyl group.
  • a methyl group, an ethyl group, or a n-propyl group is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is still more preferred.
  • the alkenyl group having 2 to 10 carbon atoms, which R 1 to R 3 each independently represent, may be linear, branched, or cyclic, and examples thereof include a vinyl group, an allyl group, a 1-penten-1-yl group, a 4-methyl-3-penten-1-yl group, a 4-penten-1-yl group, a 1-hexen-1-yl group, a 1-octen-1-yl group, and a 1-decen-1-yl group.
  • an alkenyl group having 1 to 8 carbon atoms is preferred, and an alkenyl group having 1 to 6 carbon atoms is more preferred.
  • Examples of the aryl group having 6 to 12 carbon atoms, which R 1 to R 3 each independently represent, include a phenyl group, a tolyl group, an ethylphenyl group, a xylyl group, a trimethylphenyl group, a naphthyl group, a biphenylyl group. Above all, an aryl group having 6 to 10 carbon atoms is preferred.
  • examples of the alkylene group include an ethylene group, a n-propylene group, a n-butylene group, a n-pentylene group, a hexylene group, a 2-methylethylene group, a 1,2-dimethylethylene group, a 2-methyl-n-propylene group, a 2,2-dimethyl-n-propylene group, and a 3-methyl-n-pentylene group.
  • R 1 to R 3 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 1 and R 2 are a methyl group, and it is still more preferred that both R 1 and R 2 are a methyl group.
  • R 3 is a hydrogen atom.
  • aldehyde (1) examples include 2-butenal, 2-pentenal, 2-hexenal, 2-heptenal, 2-octenal, 2-nonenal, 2-decenal, 2-undecenal, 2-dodecenal, 2-tridecenal, 4-methyl-2-pentenal, 4-methyl-2-hexenal, 5-methyl-2-hexenal, 4,4-dimethyl-2-pentenal, 6-methyl-2-heptenal, 4-ethyl-2-hexenal, 2-methyl-2-butenal, 2-methyl-2-pentenal, 2-methyl-2-hexenal, 2-methyl-2-heptenal, 2-methyl-2-octenal, 4-methyl-2-propyl-2-hexenal, 2,4-dimethyl-2-pentenal, 2,4-dimethyl-2-hexenal, 2,4-dimethyl-2-heptenal, 2,5-dimethyl-2-hexenal, 2,6-dimethyl-2-heptenal, 2,4,4
  • 3-methyl-2-butenal, 3-methyl-2-pentenal, 3-methyl-2-hexenal, 3-methyl-2-heptenal, 3-methyl-2-octenal, 3,7-dimethyl-2,6-octadienal (citral), 3-ethyl-2-pentenal, 3-ethyl-2-hexenal, and 3-propyl-2-hexenal are preferred; 3-methyl-2-butenal, 3-methyl-2-pentenal, and 3-ethyl-2-pentenal are more preferred; and 3-methyl-2-butenal (senecioaldehyde, hereinafter referred to simply as “SAL”) is still more preferred.
  • SAL 3-methyl-2-butenal (senecioaldehyde, hereinafter referred to simply as “SAL”) is still more preferred.
  • aldehyde (1) a commercially available product may be used, or it may be synthesized through an oxidative dehydrogenation reaction of a corresponding ⁇ , ⁇ -unsaturated alcohol (see, for example, JP 60-224652 A).
  • a content proportion of the aldehyde (1) that is an active ingredient in the composition of the present invention can be properly set according to the use embodiment, it is typically 1 to 99.9% by mass, and from viewpoint of cost-effectiveness, it is preferably 5 to 99.9% by mass, and more preferably 5 to 95% by mass.
  • composition of the present invention may contain other iron sulfide remover, such as acrolein, tetrakis(hydroxymethyl)phosphine or a corresponding phosphonium salt, hydrochloric acid, and formic acid, as long as the effects of the present invention are not impaired.
  • iron sulfide remover such as acrolein, tetrakis(hydroxymethyl)phosphine or a corresponding phosphonium salt, hydrochloric acid, and formic acid
  • composition of the present invention may contain an appropriate solvent, such as cyclohexane, toluene, xylene, a heavy aromatic naphtha, and a petroleum distillate; and a monoalcohol or dialcohol having 1 to 10 carbon atoms, e.g., methanol, ethanol, and ethylene glycol.
  • an appropriate solvent such as cyclohexane, toluene, xylene, a heavy aromatic naphtha, and a petroleum distillate
  • a monoalcohol or dialcohol having 1 to 10 carbon atoms, e.g., methanol, ethanol, and ethylene glycol.
  • the composition of the present invention may contain, in addition to the aldehyde (1), a component, such as a surfactant, a corrosion inhibitor, an oxygen scavenger, an iron control agent, a crosslinking agent, a breaker, a coagulant, a temperature stabilizer, a pH adjuster, a dehydration regulator, a swelling prevention agent, a scale inhibitor, a biocide, a friction reducer, a defoaming agent, an agent for preventing a lost circulation of mud water, a lubricating agent, a clay dispersant, a weighting agent, and a gelling agent, as long as the effects of the present invention are not impaired.
  • a component such as a surfactant, a corrosion inhibitor, an oxygen scavenger, an iron control agent, a crosslinking agent, a breaker, a coagulant, a temperature stabilizer, a pH adjuster, a dehydration regulator, a swelling prevention agent, a scale inhibitor,
  • composition of the present invention is not particularly limited with respect to its production method, and it can be, for example, produced by adding and mixing the aldehyde (1) with the aforementioned arbitrary component, such as an iron sulfide remover and a solvent.
  • composition of the present invention is suitably a liquid, it may be converted in a solid form, such as a powder and a fluid, upon being properly supported on a carrier, etc., according to a form to be used for the purpose of removing iron sulfide.
  • the treatment is performed by adding the composition of the present invention in an amount sufficient for the removal of iron sulfide to a liquid containing iron sulfide.
  • the composition of the present invention is added such that the amount of the aldehyde (1) contained in the composition of the present invention is preferably 0.1 to 100 parts by mass, and more preferably 2 to 100 parts by mass based on 1 part by mass of iron sulfide.
  • a temperature on the occasion of performing the treatment in which the composition of the present invention is added to and brought into contact with a liquid containing iron sulfide is preferably in a range of from 0° C. to 150° C., and more preferably from 20° C. to 130° C.
  • Acrolein Product available from Tokyo Chemical Industry Co., Ltd., which contains hydroquinone as a stabilizer
  • the point of time at when SAL was added was defined as 0 hour, and the behavior of iron sulfide was observed. As a result, after elapsing 4 hours, the iron sulfide was dissolved, and the reaction solution became colorless transparent.
  • Example 2 The same test as in Example 1 was carried out, except that citral was used in place of SAL. After elapsing 7 hours, iron sulfide was dissolved, and the reaction solution became colorless transparent.
  • Example 2 The same test as in Example 1 was carried out, except that acrolein was used in place of SAL. After elapsing 4 hours, iron sulfide was dissolved, and the reaction solution became colorless transparent.
  • Temperature rise conditions 70° C. ⁇ (temperature rise at 5° C./min) ⁇ 250° C.
  • Each of SAL and acrolein was dissolved in 0.5 mol/L of phosphoric acid buffer solutions having a pH different from each other, thereby preparing 0.1 wt % solutions. 50 mL of each of the solutions was charged in a sample vial in a nitrogen atmosphere and stored at 23 ⁇ 2° C. On the occasion when the content of each of SAL and acrolein at the time of preparation was defined as 100%, a change of the content ratio was observed according to the absolute calibration curve by means of high-performance liquid chromatography analysis. The results are shown in FIGS. 1 and 2 .
  • pH 1.7 4.9 g of 75% phosphoric acid and 7.8 g of sodium dihydrogen phosphate dihydrate were dissolved in 200 mL of distilled water.
  • pH 6.2 7.8 g of sodium dihydrogen phosphate dihydrate and 7.1 g of disodium hydrogen phosphate were dissolved in 200 mL of distilled water.
  • pH 8.1 0.3 g of sodium dihydrogen phosphate dihydrate and 13.9 g of disodium hydrogen phosphate were dissolved in 200 mL of distilled water.
  • SAL, citral, and acrolein are each an existing compound, and the information regarding the safety is disclosed. For reference, the information regarding the safety is shown in Table 2. SAL and citral are extremely low in the toxicity and safe as compared with acrolein.
  • the aldehyde (1) such as SAL
  • composition of the present invention is useful in view of the fact that it is high in the thermal stability and the pH stability and is able to remove iron sulfide safely and efficiently.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
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  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US16/312,363 2016-06-28 2017-06-21 Composition for removing iron sulfide Abandoned US20190241822A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2016-127916 2016-06-28
JP2016127916 2016-06-28
PCT/JP2017/022837 WO2018003624A1 (ja) 2016-06-28 2017-06-21 硫化鉄除去用の組成物

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US (1) US20190241822A1 (pt)
EP (1) EP3486353A4 (pt)
JP (1) JPWO2018003624A1 (pt)
CN (1) CN109415819A (pt)
BR (1) BR112018076690A2 (pt)
CA (1) CA3028940A1 (pt)
MX (1) MX2018016415A (pt)
RU (1) RU2018145752A (pt)
SG (1) SG11201811541TA (pt)
TW (1) TW201816098A (pt)
WO (1) WO2018003624A1 (pt)

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WO2019124340A1 (ja) * 2017-12-22 2019-06-27 株式会社クラレ 原油または天然ガスの採掘用処理剤

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US2402615A (en) * 1940-09-19 1946-06-25 Du Pont Catalytic process and products thereof
US2571739A (en) * 1949-10-28 1951-10-16 Pure Oil Co Prevention of corrosion of structural metals by hydrogen sulfide, air, and water
US4400368A (en) * 1981-11-24 1983-08-23 Shell Oil Company H2 S Removal process
US4734259A (en) * 1985-11-22 1988-03-29 Dowell Schlumberger Incorporated Mixtures of α,β-unsaturated aldehides and surface active agents used as corrosion inhibitors in aqueous fluids
US6086056A (en) * 1998-04-29 2000-07-11 Leask; Jim Float sink header
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US20150266756A1 (en) * 2014-03-19 2015-09-24 Enersciences Holdings, Llc Methods and apparatus for treating sulfides in produced fluids

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CA3028940A1 (en) 2018-01-04
MX2018016415A (es) 2019-05-09
RU2018145752A (ru) 2020-07-28
RU2018145752A3 (pt) 2020-07-28
CN109415819A (zh) 2019-03-01
WO2018003624A1 (ja) 2018-01-04
JPWO2018003624A1 (ja) 2019-05-16
EP3486353A1 (en) 2019-05-22
EP3486353A4 (en) 2020-03-04
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