WO2007086661A1 - Procédé permettant d'éliminer le calcium d'une huile hydrocarbonée - Google Patents

Procédé permettant d'éliminer le calcium d'une huile hydrocarbonée Download PDF

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Publication number
WO2007086661A1
WO2007086661A1 PCT/KR2007/000179 KR2007000179W WO2007086661A1 WO 2007086661 A1 WO2007086661 A1 WO 2007086661A1 KR 2007000179 W KR2007000179 W KR 2007000179W WO 2007086661 A1 WO2007086661 A1 WO 2007086661A1
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WIPO (PCT)
Prior art keywords
calcium
formula
oil
compound represented
compound
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Application number
PCT/KR2007/000179
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English (en)
Inventor
Byong Sung Kwak
Ik Sang Yoo
Dong Hyon Sheen
Sang Chul Lim
Jin Kyu Choi
Tae Won Uhm
Original Assignee
Sk Energy Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020060086201A external-priority patent/KR101300323B1/ko
Application filed by Sk Energy Co., Ltd. filed Critical Sk Energy Co., Ltd.
Publication of WO2007086661A1 publication Critical patent/WO2007086661A1/fr

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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
    • C10G29/02—Non-metals

Definitions

  • the present invention relates to a method of removing calcium from hydrocarbonaceous oil, and more particularly, to a method of removing calcium from hydrocarbonaceous oil, in which a lipophilic compound, represented by Formula 1 below, is dissolved in hydrocarbonaceous oil, including calcium-containing crude oil or hydrocarbon residue, to thus prepare a homogeneous phase, from which calcium can then be efficiently removed:
  • Rl and R2 which are the same as or different from each other, are hydrogen, methyl, ethyl, propyl, phenyl, bromo, chloro, trifluoromethyl, or 3-(4-chlorophenyl), or Rl and
  • R2 may be chemically bonded to each other to form a ring together, in which one or more members of the ring may be optionally substituted with a hetero atom, such as nitrogen, oxygen, or sulfur.
  • Ca in crude oil is mainly present in the form of calcium naphthenate. Further, crude oil having a high calcium content is crude oil (Heidrum, Captain) native to the North Sea, crude oil (Bohai, Shangri) native to China, crude oil (Shering) native to Indonesia, and crude oil (San Joaquin Valley) native to North America, as well as crude oil (Doba, Quito) native to West Africa, including Chad and Sudan, where new oil wells are being drilled these days.
  • crude oil having a high calcium content is crude oil (Heidrum, Captain) native to the North Sea, crude oil (Bohai, Shangri) native to China, crude oil (Shering) native to Indonesia, and crude oil (San Joaquin Valley) native to North America, as well as crude oil (Doba, Quito) native to West Africa, including Chad and Sudan, where new oil wells are being drilled these days.
  • US Patent No. 4,778,589 discloses a method of removing calcium from hydrocarbonaceous oil using an aqueous solution of hydroxo carboxylic acid, in particular, citric acid.
  • hydroxo carboxylic acid in particular, citric acid.
  • citric acid When calcium is removed, calcium citrate is produced.
  • Calcium citrate has low solubility in water, and thus a large amount of precipitate remains in a desalting device, remarkably decreasing calcium removal efficiency. Further, upon the removal of calcium from hydrocarbonaceous oil containing high concentrations of calcium, the pH of the aqueous solution that is used becomes too high, leading to device corrosion problems.
  • US Patent No. 4,778,590 discloses a method of removing calcium using amino-carboxylic acid or salts thereof, in particular, EDTA (Ethylene Diamino Tetra Acetic Acid).
  • EDTA Ethylene Diamino Tetra Acetic Acid
  • US Patent No. 4,778,591 discloses a method of removing calcium from hydrocarbonaceous oil using aqueous carbonic acid and salts thereof, in particular, ammonium carbonate.
  • the above method has been reported to be economically disadvantageous because ammonium carbonate should be used in an amount about 5 times as much as the amount of calcium in order to achieve calcium removal efficiency of 90% or higher.
  • US Patent Nos. 4,778,592 and 4,789,463 disclose a method of removing iron from hydrocarbonaceous oil using EDTA and citric acid, respectively.
  • US Patent No. 4,853,109 discloses a method of removing calcium using dicarboxylic acid, in particular, oxalic acid.
  • US Patent No. 4,988,433 discloses the use of monocarboxylic acid and salts thereof for calcium removal.
  • ammonium carboxylic acid is used.
  • acetic acid should be used in an amount about 30 times as much as the amount of calcium.
  • acetic acid is used in an amount 3.3 times as much as the amount of calcium, but the removal efficiency is low, around 46%, and thus the above technique is not industrially important.
  • the upper portion of a distillation device may undesirably corrode in processes subsequent to a desalting process.
  • US Patent No. 5,593,573 discloses the use of sulfonic acid or its salts, in particular, ammonium sulfate, as a calcium removal agent.
  • sulfonic acid or its salts in particular, ammonium sulfate
  • the pH of the aqueous solution layer is controlled to be 6-8, and also, a 10% precipitation inhibitor is used therewith so as to prevent the production of a great amount of calcium sulfate in the desalting process.
  • the above patent suffers because the use of the agent is complicated and economic benefits are negated.
  • ammonium sulfate should be used in an amount at least 6 times the amount of calcium, leading to negation of economic and industrial benefits.
  • sulfonic acid which is a strong acid, remains in the hydrocarbonaceous oil, it causes problems of corrosion of the distillation device in processes subsequent to the desalting process.
  • US Patent Application Publication Nos. 2004-45875 and 2005-241997 disclose a method of removing metal and amine from hydrocarbonaceous oil using aqueous hydroxy acid.
  • the hydroxy acid used include glycolic acid, glucolic acid, C2-C4 alpha-hydroxy acid, and polyhydroxy acid.
  • the glycolic acid is problematic because it remains in the hydrocarbonaceous oil and consequently corrodes the upper portion of a distillation column at high temperatures in processes subsequent to the desalting process.
  • US Patent No. 6,905,593 discloses a method of removing calcium from hydrocarbonaceous oil by maintaining the pH of an aqueous layer in the range of 3.0 ⁇ 5.0 using acetic acid and aqueous ammonia.
  • the control of the pH requires an excessive amount of water, and acetic acid should be used in an amount 9 times the amount of calcium so as to assure calcium removal efficiency of 98% or higher, and thus the industrial usefulness of the above method is limited.
  • secondary corrosion of the distillation device is caused by the acetic acid dissolved in hydrocarbonaceous oil.
  • Japanese Unexamined Patent Publication No. Sho. 52-30284 discloses a method of removing various metals from crude oil using inorganic acid, alkyl phosphate ester and an oxidant.
  • Japanese Unexamined Patent Publication No. Sho. 47-22947 discloses a method of removing metal using alkyl phosphate ester and alkyl carboxylic acid in the absence of inorganic acid, but it results in low metal removal efficiency.
  • the above methods are useful for rapidly mixing the lipophilic layer, comprising hydrocarbon oil, with the aqueous layer, in which the calcium removal agent is dissolved, so as to increase the calcium removal efficiency, and furthermore, for generating an interfacial reaction between the two layers, which are not mixed with each other.
  • the crude oil having high concentrations of calcium, it is difficult to mix, attributable to the viscosity thereof, and thereby limitations are imposed on the use of the high- concentration mixing ratio.
  • all the methods for increasing the calcium removal efficiency have the above-mentioned problems.
  • a lipophilic compound represented by Formula 1 when used, it can be directly added to hydrocarbonaceous oil to thus dissolve it and can consequently be provided in a homogeneous phase in which the compound is uniformly dissolved in crude oil or hydrocarbonaceous oil without the use of an excessive amount of water or another solvent, and furthermore, using only the water present in hydrocarbonaceous oil or a small additional amount of water, the compound is hydrolyzed to thus react with a calcium compound, thereby easily and efficiently removing calcium from hydrocarbonaceous oil, including high-calcium crude oil or hydrocarbon residue.
  • an object of the present invention is to provide a novel method of efficiently removing calcium from hydrocarbonaceous oil, including crude oil or hydrocarbon residue.
  • the present invention provides a method of removing calcium from crude oil, comprising steps of:
  • Rl and R2 which are the same as or different from each other, are hydrogen, methyl, ethyl, propyl, phenyl, bromo, chloro, trifluoromethyl, or 3-(4-chlorophenyl), or Rl and R2 may be chemically bonded to each other to form a ring together, in which one or more members of the ring may be optionally substituted with a hetero atom, such as nitrogen, oxygen, or sulfur;
  • Rl and R2 are as defined above; 3) subjecting the compound represented by Formula 2 along with calcium naphthenate present in the homogeneous mixture to metal substitution, thus producing calcium dicarboxylate; and
  • a lipophilic dicarboxylic anhydride compound is completely dissolved in calcium-containing oil, such as crude oil, to form a homogeneous phase, which is then subjected to hydrolysis to thus produce an aqueous compound having a carboxylic group, after which the aqueous compound is reacted with calcium so that the calcium is deposited as an insoluble material for easy removal, thereby effectively removing calcium while solving problems related to the limited mixing ratio of crude oil having high concentrations of calcium, pH control, and transport and use thereof due to the use of excessive amount of water.
  • the method of the present invention can be advantageously applied to the extraction of high-calcium crude oil from an oil well, the pretreatment of crude oil before distillation, the removal of calcium from hydrocarbon mixtures, and the efficient removal of calcium from other oils containing calcium, and is therefore expected to be industrially useful.
  • the method of efficiently removing calcium from hydrocarbonaceous oil including calcium-containing crude oil or hydrocarbon residue is provided.
  • the method of the present invention is characterized in that it selectively uses a lipophilic compound represented by Formula 1 below:
  • Rl and R2 which are the same as or different from each other, are hydrogen, methyl, ethyl, propyl, phenyl, bromo, chloro, trifluoromethyl, or 3-(4-chlorophenyl), or Rl and R2 may be chemically bonded to each other to form a ring together, in which one or more members of the ring may be optionally substituted with a hetero atom, such as nitrogen, oxygen, or sulfur.
  • a lipophilic dicarboxylic anhydride compound which may be converted into an aqueous compound having a carboxylic group through hydrolysis, is selected, and then a homogeneous mixture is prepared. Thereafter, a compound having a carboxylic group, produced through hydrolysis, is reacted with calcium in the oil, yielding an insoluble compound, capable of being deposited, whereby the calcium can be effectively removed through the simple and easy process of the invention.
  • the method of removing the calcium according to the present invention comprises 1) adding a lipophilic compound represented by Formula 1 to a hydrocarbon source containing calcium, thus preparing a homogeneous mixture; 2) hydrolyzing the compound represented by Formula 1 in the homogeneous mixture, thus producing a compound represented by Formula 2 below:
  • Rl and R2 are as defined above; 3) subjecting the compound represented by Formula 2 and calcium naphthenate present in the homogeneous mixture to metal substitution, thus producing calcium dicarboxylate; and 4) desalting the calcium dicarboxylate to thereby remove it.
  • the present invention is intended to remove calcium from a hydrocarbon source, not limited to high-calcium crude oil and hydrocarbon residue, including atmospheric residue or vacuum residue, which is a semi-finished product obtained in a crude oil refining process, but also including other hydrocarbon oils, such as shale oil, shale sands, liquefied coal oil, and tar sands. Accordingly, the method of the present invention enables the effective removal of calcium from a hydrocarbon source containing 10 to 3,000 ppm calcium.
  • an appropriate lipophilic dicarboxylic anhydride compound represented by
  • Formula 1 which may be converted into an aqueous compound having a carboxylic group through hydrolysis, is selected and added to a hydrocarbon source including calcium-containing crude oil or hydrocarbon reside from which the calcium should be removed.
  • the compound may be directly added in a solid phase or in a liquid phase, or alternatively, may be added in the form of a high-concentration solution through dissolution in a diluting agent.
  • a diluting agent any solvent may be used, as long as it may dissolve the dicarboxylic anhydride compound represented by Formula 1, with the exception of water.
  • Examples of a general organic solvent include, but are not limited to, acetone, benzene, xylene, kerosene, 1,4-dioxane, chloroform, carbon tetrachloride, ethylacetate, dimethylforrnamide, tetrahydrofuran, dimethylsulfoxide, sulfolane, methylethylketone, and/or diethyleneglycol dimethylether, and preferably, xylene, dimethylformamide, tetrahydrofuran, dimethylsulfoxide, diethyleneglycol dimethylether and/or 1,4-dioxane.
  • concentration of the compound to be diluted varies with the solvent, it preferably falls within the range from 5 to 80 wt%, and more preferably from 20 to 60 wt%.
  • the compound represented by Formula 1 is used in a molar ratio ranging from 0.5 to 20, and preferably 1.0 to 10 relative to the amount of calcium contained in the crude oil.
  • the molar ratio is less than 0.5, the removal efficiency is decreased in terms of the equivalent reaction.
  • the ratio exceeds 20, the disposal cost is increased, and furthermore, the cost of post-treatment in a wastewater disposal plant after the desalting process is greatly increased.
  • the compound represented by Formula 1 is added to the crude oil or hydrocarbon oil to thus prepare a homogeneous mixture
  • any method which is known to those skilled in the art may be applied.
  • the added compound is stirred at a predetermined temperature of 20 ⁇ 80°C, and preferably 30 ⁇ 50°C, for a time period ranging from 1 sec to 2 hours, and preferably from 0.2 min to 0.5 hours, so as to realize complete dispersion and sufficient dissolution thereof.
  • a homogeneous mixture in which the anhydride compound represented by Formula 1 is completely dissolved, may be obtained.
  • the compound represented by Formula 1 is hydrolyzed using water which is already present in the crude oil, thereby producing the compound represented by Formula 2.
  • the compound may be hydrolyzed even without the use of additional water.
  • water is further added in an amount not less than the minimum amount required to hydrolyze the compound represented by Formula 1.
  • water is used in a molar ratio ranging from 1 to 10, and preferably 1.5 to 5, relative to the amount of the compound represented by Formula 1.
  • the hydrolysis is performed at a reaction temperature of 30 ⁇ 90°C, and preferably 40 ⁇ 80°C, for a reaction time of 1-30 min, and preferably 5-10 min.
  • the compound thus produced, represented by Formula 2 is present in a dissolved and homogeneous state.
  • the compound represented by Formula 2 and the calcium naphthenate are subjected to metal substitution, thus producing calcium dicarboxylate.
  • the stirring speed of the reactor be controlled. For example, a stirring speed of 100-4,000 ⁇ m, and preferably 200-3,000 rpm, should be maintained to assure a desired mixing state.
  • the stirring speed of an impeller is increased when a mixing pump and a centrifugal pump have the same mixing capability.
  • a reaction temperature of 30-180°C, and preferably 50 ⁇ 140°C, and a reaction time ranging from 1 sec to 4 hours, and preferably from 1 min to 60 min, be maintained.
  • the produced calcium dicarboxylate is removed through a desalting process.
  • a general production process may be applied, hi the present invention, the process was performed using a PED (Portable Electronic Desalter, available from Inter Av.).
  • the desalting process was performed for a time period ranging from 10 min to 2 hours, and preferably 1 hour, and at 50 ⁇ 100°C, and preferably 9O 0 C.
  • water may be used in an amount of 5 ⁇ 50%, and preferably 10%.
  • an additive is used to increase oil-water separation efficiency, and any additive typically known in the art may be used.
  • a commercially available demulsifier Prochem 2X24, Petrolite
  • the method of removing the calcium is preferably conducted at a reaction pressure ranging from atmospheric pressure to 20 atm.
  • the method of the present invention is expected to be variously applicable to diverse fields requiring the removal of calcium, in particular, the extraction of high-calcium crude oil from oil wells, the pretreatment of crude oil before distillation, and the removal of calcium from hydrocarbon mixtures and other oils.
  • MAN was added in solid phase or in liquid phase, in which it was dissolved in an organic solvent, after which the stirring speed was set at 1,000 rpm and the reaction temperature was increased to 4O 0 C, followed by performing the stirring process for 10 min. 25.2 ⁇ l of water was added thereto, and the reaction temperature was increased to 90°C, followed by performing the stirring process for 2 hours.
  • the reaction solution was removed from the high-pressure reactor, and 90 g thereof was placed in a 100 ml reactor. 10 ml of water was added thereto and 1 mg of a demulsifier
  • EDPT Electrostatic Dehydration & Precipitation Tester
  • the calcium removal reaction was conducted in the same manner as in Example 2, with the exception that the reaction was performed under atmospheric pressure and high pressure.
  • the period of time required to increase the temperature of crude oil from room temperature to 140°C was 10 min.
  • the reaction time and temperature were adjusted to be suitable for the production site, and a 20% Doba blend was used, and thus the reaction conditions were simulated.
  • the period of time required to transfer the crude oil to the desalter was 10 min.
  • the temperature was increased from room temperature to 140°C, and, for the next 7 min, the reaction temperature was maintained at 140°C before the oil was added into the desalter.
  • Table 6 which shows the results of testing to determine the time and temperature required for treating the crude oil used in an actual distillation plant, when the method of the present invention was applied at a production site, excellent efficiency could be realized.

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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)

Abstract

Cette invention concerne un procédé permettant d'éliminer le calcium d'une huile hydrocarbonée et concerne en particulier un procédé permettant d'éliminer le calcium d'une huile hydrocarbonée consistant à ajouter un composé lipophile à l'huile hydrocarbonée, telle qu'une huile brute contenant du calcium ou un résidu d'hydrocarbure, afin de préparer un mélange homogène qui est ensuite hydrolysé puis mis en réaction avec le composé calcium présent dans l'huile de façon que le calcium puisse être éliminé plus facilement et plus efficacement. Contrairement aux procédés conventionnels, le procédé de cette invention utilise un composé soluble dans l'huile hydrocarbonée, telle qu'une huile brute à forte teneur en calcium, ce qui supprime le besoin de recourir à un processus de séparation d'une couche lipophile d'une couche aqueuse nécessitant une quantité d'eau excessive, et permet d'éliminer le calcium facilement et efficacement. Le procédé de cette invention présente par conséquent des avantages en terme d'utilité industrielle.
PCT/KR2007/000179 2006-01-25 2007-01-10 Procédé permettant d'éliminer le calcium d'une huile hydrocarbonée WO2007086661A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20060007770 2006-01-25
KR10-2006-0007770 2006-01-25
KR1020060086201A KR101300323B1 (ko) 2006-01-25 2006-09-07 탄화수소류 유분으로부터 칼슘의 제거방법
KR10-2006-0086201 2006-09-07

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009113095A3 (fr) * 2008-01-24 2009-11-26 Dorf Ketal Chemicals (I) Private Limited Procédé d’élimination de métaux d’une charge d’hydrocarbures en utilisant des esters d’acides carboxyliques
WO2013024489A1 (fr) * 2011-06-29 2013-02-21 Dorf Ketal Chemicals (India) Private Limited Additif et procédé d'élimination du calcium des huiles contenant du naphténate de calcium
US8685233B2 (en) 2006-08-22 2014-04-01 Dork Ketal Chemicals (I) Private Limited Method of removal of calcium from hydrocarbon feedstock
US9790438B2 (en) 2009-09-21 2017-10-17 Ecolab Usa Inc. Method for removing metals and amines from crude oil
US20200199438A1 (en) * 2017-06-19 2020-06-25 Ecolab Usa Inc. Naphthenate inhibition
WO2020130852A1 (fr) * 2018-12-21 2020-06-25 Equinor Energy As Traitement d'hydrocarbures produits

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5976358A (en) * 1996-10-04 1999-11-02 Exxon Research And Engineering Co. Removal of +2 ion charged metal dissolved in a petroleum feed
US20030150779A1 (en) * 2000-05-30 2003-08-14 Collins Ian Ralph Process for removing metal ions from crude oil
US6905593B2 (en) * 2003-09-30 2005-06-14 Chevron U.S.A. Method for removing calcium from crude oil
US20050241996A1 (en) * 2004-05-03 2005-11-03 Garcia Juan M Iii Decalcification of refinery hydrocarbon feedstocks

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5976358A (en) * 1996-10-04 1999-11-02 Exxon Research And Engineering Co. Removal of +2 ion charged metal dissolved in a petroleum feed
US20030150779A1 (en) * 2000-05-30 2003-08-14 Collins Ian Ralph Process for removing metal ions from crude oil
US6905593B2 (en) * 2003-09-30 2005-06-14 Chevron U.S.A. Method for removing calcium from crude oil
US20050241996A1 (en) * 2004-05-03 2005-11-03 Garcia Juan M Iii Decalcification of refinery hydrocarbon feedstocks

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8685233B2 (en) 2006-08-22 2014-04-01 Dork Ketal Chemicals (I) Private Limited Method of removal of calcium from hydrocarbon feedstock
US9080110B2 (en) 2008-01-24 2015-07-14 Dorf Ketal Chemicals (I) Private Limited Composition comprising combination of esters of carboxylic acids for removing metals from hydrocarbon feedstock
CN101939285A (zh) * 2008-01-24 2011-01-05 多尔夫凯塔尔化学制品（I）私人有限公司 利用羧酸酯从原料烃中去除金属的方法
JP2011510151A (ja) * 2008-01-24 2011-03-31 ドルフ ケタール ケミカルズ（Ｉ） プライベート リミテッド カルボン酸のエステルを使用して炭化水素供給原料から金属を除去する方法
AU2009222921B2 (en) * 2008-01-24 2012-12-06 Dorf Ketal Chemicals (I) Private Limited Method of removing metals from hydrocarbon feedstock using esters of carboxylic acids
US8440072B2 (en) 2008-01-24 2013-05-14 Dorf Ketal Chemicals (I) Private Limited Method of removing metals from hydrocarbon feedstock using esters of carboxylic acids
KR101606515B1 (ko) 2008-01-24 2016-03-25 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 카르복실산의 에스테르를 이용한 탄화수소 공급 원료에서의 금속 제거 방법
WO2009113095A3 (fr) * 2008-01-24 2009-11-26 Dorf Ketal Chemicals (I) Private Limited Procédé d’élimination de métaux d’une charge d’hydrocarbures en utilisant des esters d’acides carboxyliques
US9790438B2 (en) 2009-09-21 2017-10-17 Ecolab Usa Inc. Method for removing metals and amines from crude oil
US8840781B2 (en) 2011-06-29 2014-09-23 Dorf Ketal Chemicals (India) Private Limited Additive and method for removal of calcium from crude oils containing calcium naphthenate
KR20140045508A (ko) * 2011-06-29 2014-04-16 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 칼슘 나프테네이트를 함유하는 오일에서 칼슘 제거를 위한 첨가제 및 방법
AU2012296145B2 (en) * 2011-06-29 2016-03-31 Dorf Ketal Chemicals (India) Private Limited Additive and method for removal of calcium from oils containing calcium naphthenate
TWI551676B (zh) * 2011-06-29 2016-10-01 多爾夫凱塔爾化學製品（Ｉ）私人有限公司 用於自含有環烷酸鈣之原油中移除鈣之添加劑及方法
WO2013024489A1 (fr) * 2011-06-29 2013-02-21 Dorf Ketal Chemicals (India) Private Limited Additif et procédé d'élimination du calcium des huiles contenant du naphténate de calcium
KR101866927B1 (ko) * 2011-06-29 2018-06-14 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 칼슘 나프테네이트를 함유하는 오일에서 칼슘 제거를 위한 첨가제 및 방법
US20200199438A1 (en) * 2017-06-19 2020-06-25 Ecolab Usa Inc. Naphthenate inhibition
US11718779B2 (en) * 2017-06-19 2023-08-08 Championx Usa Inc. Naphthenate inhibition
WO2020130852A1 (fr) * 2018-12-21 2020-06-25 Equinor Energy As Traitement d'hydrocarbures produits
US11965131B2 (en) 2018-12-21 2024-04-23 Equinor Energy As Treatment of produced hydrocarbons

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