WO1996005271A1 - Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz - Google Patents

Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz Download PDF

Info

Publication number
WO1996005271A1
WO1996005271A1 PCT/IB1995/000623 IB9500623W WO9605271A1 WO 1996005271 A1 WO1996005271 A1 WO 1996005271A1 IB 9500623 W IB9500623 W IB 9500623W WO 9605271 A1 WO9605271 A1 WO 9605271A1
Authority
WO
WIPO (PCT)
Prior art keywords
metal hydroxide
petroleum
catalyst
aqueous solution
cobalt
Prior art date
Application number
PCT/IB1995/000623
Other languages
English (en)
Inventor
Akhmet Mazgarovich Mazgarov
Azat Faridovich Vildanov
Nailya Gilmutdinovna Bazhirova
Gulnara Burkhanova Niamutdinova
Sergei Nikolaevich Sukhov
Original Assignee
Chevron U.S.A. Inc.
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 Chevron U.S.A. Inc. filed Critical Chevron U.S.A. Inc.
Priority to AU29900/95A priority Critical patent/AU2990095A/en
Priority to MX9700934A priority patent/MX9700934A/es
Priority to EP95925985A priority patent/EP0775182A1/fr
Priority to US08/509,402 priority patent/US5683574A/en
Publication of WO1996005271A1 publication Critical patent/WO1996005271A1/fr
Priority to NO970588A priority patent/NO970588L/no

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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water

Definitions

  • the present invention relates to petrochemistry, specifically to a method for the extraction of mercaptans from petroleum and gas condensates, and may find application in the petroleum, natural gas, petroleum-processing and petrochemical industry.
  • a method for the extraction of mercaptan from petroleum and petroleum byproducts by means of processing the raw material with a cuprate of the naphthene in the oil with the weight ratio of the copper salt to the mercaptan in the raw material falling within the range of from 3 to 4:1 (see Russian Author's Certificate No. 1616959 issued in 1990.)
  • the principal disadvantages of the aforesaid method are: the high rate of consumption of the scarce reagent involved, especially when purifying petroleum with a high content of sour sulfur (mercaptan sulfur) , the difficulty of separating the resulting precipitate from the purified product, the formation of a waste byproduct (a precipitate) which is difficult to utilize, as well as the loss of the purified product together with the discarded residue.
  • sour sulfur mercaptan sulfur
  • the method which most closely resembles the method of the present invention both in its technological essence and the obtained result is a method for the extraction of mercaptans from petroleum distillates by processing with the oxygen of the air in an aqueous solution of an alkali metal hydroxide, in the presence of a cobalt octocarboxytetraphenylphthalocyanine catalyst, in an amount of 0.005 to 0.2 weight percent, as calculated with respect to the aqueous solution of the alkali metal hydroxide (see Russian Author's Certificate No. 1824421 issued in 1991).
  • the principal disadvantages of this method are to be found in the insufficiently high degree of mercaptan extraction from the raw material as well as the low stability of the catalytic activity of the catalyst. it is an object of the present invention to increase the degree to which the raw material is purified and the mercaptan extracted, to increase the stability of the catalytic activity of the catalyst under the conditions of the purification of petroleum and gas condensate.
  • a method of extraction of low molecular weight mercaptans from petroleum or gas condensate containing such low molecular weight mercaptans comprising (1) contacting the mercaptans with oxygen in an aqueous solution of a metal hydroxide, in the presence of a cobalt dihalodihydroxydisulfophthalocyanine catalyst, the catalyst being used in an amount within the range of from about 0.5 x ⁇ o *5 to about 2.5 x 10 "5 weight percent based on the weight of the petroleum or gas condensate, the catalyst being introduced into the petroleum or gas condensate continuously in the form of a catalytic complex in an aqueous solution of a metal hydroxide, the extraction method being conducted at temperature ranging from about 40 to about 60°C and a pressure ranging from about 1.0 to about 1.4 MPa, and (2) separating the petroleum or gas condensate from the aqueous solution of metal hydroxide.
  • the catalytic complex has been prepared by dissolving cobalt dihalodihydroxydisulfo-phthalocyanine in an aqueous solution of a metal hydroxide comprising about 1 weight percent metal hydroxide, based on the combined weight of the metal hydroxide and water, with the subsequent adjustment of the concentration of the metal hydroxide upwards to a level of about 2 to about 20 weight percent.
  • the present invention further provides cobalt dihalodihydroxy-disulfophthalocyanines having the general formula:
  • R is -OH, R t is halogen and R 2 is -S0 3 H.
  • the distinguishing features of the method of the present invention are to be found in the use of the cobalt dihalo- dihydroxydisulfophthalocyanine as the catalyst, the continuous introduction of the catalyst into the petroleum or gas condensate in the form of a catalytic complex in an aqueous solution of a metal hydroxide, the manner of preparation of the catalytic complex which is to be used, and the preferred conditions for the performance of the process.
  • the aforesaid distinguishing characteristics of the proposed method define its novelty and the level of the invention, as compared to the established state-of-the-art, since the application of the cobalt dihalodihydroxydisulfophthalocyanine, with its continuous introduction into the raw material in the form of a catalytic complex, in an aqueous solution of a metal hydroxide, for the purpose of treating petroleum and gas condensates has not been described in the literature, whereas it permits the process to be carried out with a higher degree of mercaptan oxidation, under conditions involving the prolonged use of the catalyst with a decrease in the rate of its consumption.
  • the present invention provides a method of treating petroleum, e.g. whole crude oil, or gas condensates which contain low molecular weight mercaptans to convert the low molecular weight mercaptans to disulfides.
  • low molecular weight mercaptans refers to mercaptans in the C 1 -C 3 range.
  • the method of this invention employs a cobalt dihalo- dihydroxydisulfophthalocyanine catalyst.
  • This catalyst has the following general formula:
  • R is -OH, R, is halogen (e.g., -Cl or -Br) and Rj is -
  • phthalocyanine structure is not believed to be critical.
  • 17 molecule of the catalyst may contain 1-3 -OH groups, 2-4
  • halogens 18 halogens and 1-3 -S0 3 H groups.
  • the - ⁇ 9 preferred halogen is chlorine, though bromine may also be 20 U sed.
  • the catalyst of this invention is dissolved in an aqueous solution of an metal hydroxide.
  • suitable metal hydroxides include the alkali metal hydroxides and alkaline earth metal hydroxides.
  • the preferred metal hydroxides are the alkali metal hydroxides, with sodium hydroxide being particularly preferred.
  • the concentration of the metal hydroxide in the solution used to treat the petroleum or gas condensate should be from about 2 to about 20 weight percent, based on the weight of the metal hydroxide and water.
  • the cobalt dihalodihydroxydisulfophthalocyanine catalyst of this invention does not readily dissolve either in water or in a strongly alkaline aqueous solution.
  • a weakly alkaline aqueous solution e.g., one containing about one weight percent metal hydroxide
  • raise the metal hydroxide concentration in the resulting catalyst-containing solution to the desired level of from about 2 to about 20 weight percent.
  • Example 1 The proposed method has been successfully tested on a pilot installation with a capacity of 2 tons/hr, using crude oil and gas condensate from the Tengiz formation as a test sample. The method shall now be described with reference to the following examples.
  • Example 1 The proposed method has been successfully tested on a pilot installation with a capacity of 2 tons/hr, using crude oil and gas condensate from the Tengiz formation as a test sample. The method shall now be described with reference to the following examples.
  • Example 1 Example 1
  • the extraction of low molecular weight mercaptans from oil is carried out using a pilot installation, which consists of a cavity to be used for the preparation of the catalytic complex, a reaction column, a settling tank for the separation of the treated oil from the alkaline solution, and pump to be used to supply the solution to a mixer.
  • the initial crude oil, the air, and the catalytic complex together with the aqueous solution of an alkali metal hydroxide which is circulating through the system are continuously fed to the mixer, and from there to the reaction column.
  • the obtained products are fed from the reaction column into the settling tank, taking off treated oil from the top of the column and the circulating alkaline solution from the bottom.
  • the alkaline solution then returns to the mixer and is reused.
  • the continuous supply of the catalytic complex to the mixer is performed by means of a dosing pump, from the cavity which is to be used to prepare the catalytic complex.
  • the preparation of the catalytic complex of cobalt dihalo- dihydroxydisulfophthalocyanine in an aqueous solution of an alkali metal hydroxide is carried out according to the following procedure. 1.6 Grams of cobalt dichlorodihydroxydisulfo-phthalocyanine is dissolved in two liters of a 1 weight percent aqueous solution of an alkali metal hydroxide. Once the catalyst has been completely dissolved, the concentration of the alkali metal hydroxide is adjusted upwards to a level of 20 weight percent. The obtained catalyst solution is introduced into the reaction system at a rate of 0.2 liter/hr. During this time, the 01 concentration of the catalyst constitutes 1 x 10" 5 weight
  • gas condensate is subjected to purification with the continuous supply of the catalytic complex of cobalt dichlorodihydroxy-disulfophthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.1 liter per hour.
  • concentration of catalyst is 0.5 x 10 "5 weight percent. Every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • oil is subjected to purification with the continuous supply of the catalytic complex of cobalt dichlorodihydroxydisulfo- phthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.5 liter per hour.
  • concentration of catalyst in terms of the oil is 2.5 x 10 "s weight percent.
  • the temperature of the process is maintained at 60°C. Every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • gas condensate is subjected to purification with the continuous supply of the catalytic complex of cobalt dichlorodihydroxy-disulfophthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.1 liter per. hour.
  • concentration of catalyst is 0.5 x 10" 5 weight percent.
  • the pressure of the system is maintained at 1.0 MPa Every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • gas condensate is subjected to purification with the continuous supply of the catalytic complex of cobalt dichlorodihydroxy-disulfophthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.1 liter per hour.
  • concentration of catalyst is 0.5 x 10 s weight percent.
  • the pressure of the system is maintained at 1.4 MPa every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • oil is subjected to purification with a single-step of loading the reaction system with the catalytic complex of cobalt dichloro-dihydroxydisulfophthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.1 liter per hour.
  • concentration of catalyst comprises 2.5 x 10' 3 weight percent. Every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • oil is subjected to purification with the continuous supply of the catalytic complex of octacarboxytetraphenylphthalocyanine in an aqueous solution of an alkali metal hydroxide, prepared as in the case of Example 1, at a rate of 0.5 liter per hour.
  • concentration of catalyst is 2.5 x 10 '5 weight percent. Every four hours, a sample of treated oil is removed and analyzed for the presence of methylmercaptan and ethylmercaptan. The results of the experiment are given in the Table below.
  • the upper aqueous layer is poured off, and the precipitate is filtered on a Nutch filter.
  • the obtained paste is dried at 100°C to a residual humidity of no more than 2%.
  • the dried product is ground in a mill, producing the catalyst powder. It should be noted that this powder may contain impurities, but they do not appear to affect the performance of the catalyst.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Le procédé d'extraction des mercaptans à bas poids moléculaire présents dans le pétrole (par exemple le pétrole brut) ou dans les condensats de gaz consiste à mettre en contact ces mercaptans avec de l'oxygène dans une solution aqueuse d'un hydroxyde métallique, en présence d'une dihalodihydroxydisulfophtalocyanine de cobalt comme catalyseur. Le catalyseur est utilisé à une concentration entre 0,5x10-5 % environ à 2,5x10-5 % environ en poids du pétrole ou du condensat de gaz. Le catalyseur est introduit dans le pétrole brut ou le condensat de gaz d'une manière continue, sous la forme d'un complexe catalytique dans une solution aqueuse d'un hydroxyde métallique. L'extraction s'effectue à une température située entre 40 °C environ et 60 °C environ, sous une pression située entre 1,0 Mpa environ et 1,4 Mpa environ. Finalement, on sépare le pétrole ou le condensat de gaz de la solution de l'hydroxyde métallique.
PCT/IB1995/000623 1994-08-08 1995-07-27 Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz WO1996005271A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU29900/95A AU2990095A (en) 1994-08-08 1995-07-27 A method for the extraction of low molecular weight mercaptans from petroleum and gas condensates
MX9700934A MX9700934A (es) 1994-08-08 1995-07-27 Un metodo para la extraccion de mercaptanos de bajo peso molecular, a patir de petroleo y condensados de gas.
EP95925985A EP0775182A1 (fr) 1994-08-08 1995-07-27 Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz
US08/509,402 US5683574A (en) 1994-08-08 1995-07-31 Method for the extraction of low molecular weight mercaptans from petroleum and gas condensates
NO970588A NO970588L (no) 1994-08-08 1997-02-07 Fremgangsmåte for ekstrahering av lavmolekylære merkaptaner fra petroleum og gasskondensat, og katalysator anvendt ved fremgangsmåten

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU94029714A RU2087521C1 (ru) 1994-08-08 1994-08-08 Способ очистки нефти и газоконденсата от низкомолекулярных меркаптанов
RU94029714 1994-08-08

Publications (1)

Publication Number Publication Date
WO1996005271A1 true WO1996005271A1 (fr) 1996-02-22

Family

ID=20159512

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB1995/000623 WO1996005271A1 (fr) 1994-08-08 1995-07-27 Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz

Country Status (7)

Country Link
EP (1) EP0775182A1 (fr)
AU (1) AU2990095A (fr)
CA (1) CA2196287A1 (fr)
MX (1) MX9700934A (fr)
NO (1) NO970588L (fr)
RU (1) RU2087521C1 (fr)
WO (1) WO1996005271A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2458968C1 (ru) * 2011-02-09 2012-08-20 Ооо "Фотохим" Каталитическая композиция для демеркаптанизации нефти и нефтепродуктов
MD4420C1 (ro) * 2012-06-26 2017-02-28 Оп "Matricon" Ооо Aplicarea componentelor grele întunecate ale petrolului în calitate de catalizator la purificarea oxidativă de hidrogen sulfurat şi mercaptani uşori a compoziţiilor de hidrocarburi şi procedeu de purificare a compoziţiilor de hidrocarburi
RU2656100C2 (ru) * 2016-11-21 2018-05-31 Закрытое акционерное общество "ИВКАЗ" Каталитическая композиция для демеркаптанизации нефти и газоконденсата
RU2750214C1 (ru) * 2020-10-01 2021-06-24 Общество с ограниченной ответственностью "Синтез" Каталитическая композиция для окислительной демеркаптанизации нефти и нефтепродуктов

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3352777A (en) * 1964-12-09 1967-11-14 Universal Oil Prod Co Oxidation of mercaptans
FR2588266A1 (fr) * 1985-10-04 1987-04-10 Inst Francais Du Petrole Procede ameliore d'adoucissement de coupes petrolieres en lit fixe
FR2588265A1 (fr) * 1985-10-04 1987-04-10 Inst Francais Du Petrole Procede d'adoucissement d'une charge d'hydrocarbures contenant des produits soufres

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3352777A (en) * 1964-12-09 1967-11-14 Universal Oil Prod Co Oxidation of mercaptans
FR2588266A1 (fr) * 1985-10-04 1987-04-10 Inst Francais Du Petrole Procede ameliore d'adoucissement de coupes petrolieres en lit fixe
FR2588265A1 (fr) * 1985-10-04 1987-04-10 Inst Francais Du Petrole Procede d'adoucissement d'une charge d'hydrocarbures contenant des produits soufres

Also Published As

Publication number Publication date
RU2087521C1 (ru) 1997-08-20
RU94029714A (ru) 1996-06-20
MX9700934A (es) 1997-04-30
NO970588D0 (no) 1997-02-07
NO970588L (no) 1997-02-07
EP0775182A1 (fr) 1997-05-28
CA2196287A1 (fr) 1996-02-22
AU2990095A (en) 1996-03-07

Similar Documents

Publication Publication Date Title
DE68920559T2 (de) Katalysatorrückgewinnung.
US4090954A (en) Method for oxidizing mercaptans and mercaptide compounds from aqueous alkaline solutions and hydrocarbon distillates
DE1212903B (de) Verfahren zur katalytischen Oxydation von niederwertigen Schwefelverbindungen in Abwaessern
DE2358410A1 (de) Verfahren zur regeneration von katalysatoren
EP0198730A2 (fr) Procédé de régénération d'un catalyseur usagé par une solution aqueuse de peroxyde d'hydrogène stabilisée par un composé organique
JP2889068B2 (ja) ポリスルフイド類の精製法
JP2002241767A (ja) 液状炭化水素からの水銀除去方法
US5683574A (en) Method for the extraction of low molecular weight mercaptans from petroleum and gas condensates
EP0775182A1 (fr) Procede d'extraction des mercaptans a bas poids moleculaire presents dans le petrole et les condensats de gaz
JPS62250092A (ja) デイ−ゼル油の品質向上法
US5880279A (en) Cobalt dihalodihydroxydisulfophthalocyanines
EP0002880B1 (fr) Régénération d'une solution absorbante
US1771350A (en) Process of refining hydrocarbon oils
EP3271487B1 (fr) Traitement d'oximes dégradés, utilisés comme agents d'extraction de métaux, dans des solutions de traitement organiques
JP3824457B2 (ja) 液状炭化水素中の水銀除去法
CA1070504A (fr) Methode d'extraction de l'arsenic de solutions electrolytiques de cuivre, ou de solutions analogues
JPH01113492A (ja) 接触酸化によりスイートニングしたジェット燃料の熱安定性向上法
US4808299A (en) Removal of copper and iron from oil
US1980555A (en) Process for treating oils with an alkaline sulphide
RU2269566C1 (ru) Способ подготовки сероводородсодержащей нефти
US1935207A (en) Process for the purification of a crude hydrocarbon
US2255417A (en) Process for refining hydrocarbons
RU2699020C1 (ru) Способ очистки высококипящих углеводородных фракций от меркаптанов
RU2683283C1 (ru) Способ регенерации молибденсодержащего катализатора гидроконверсии тяжелого углеводородного сырья
JPS6333421B2 (fr)

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 95194287.5

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AM AU BB BG BR BY CA CN CZ EE FI GE HU JP KG KP KR KZ LK LR LT LV MD MG MN MX NO NZ PL RO RU SI SK TJ TT UA UZ VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2196287

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: PA/a/1997/000934

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 1995925985

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1995925985

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1995925985

Country of ref document: EP