CN1847366A - Method of eliminating naphthenic acid from crude oil or fraction oil - Google Patents
Method of eliminating naphthenic acid from crude oil or fraction oil Download PDFInfo
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- CN1847366A CN1847366A CN 200610075671 CN200610075671A CN1847366A CN 1847366 A CN1847366 A CN 1847366A CN 200610075671 CN200610075671 CN 200610075671 CN 200610075671 A CN200610075671 A CN 200610075671A CN 1847366 A CN1847366 A CN 1847366A
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Abstract
The method of eliminating naphthenic acid from crude oil or fraction oil is to add at least one kind of ionic liquid and/or one supplementary compound into crude oil or fraction oil and to eliminate naphthenic acid through mixing reaction at 20-80 deg.c, standing and separating. The ionic liquid and the supplementary compound possess excellent miscibility with the crude oil or the fraction oil, and thus has less emulsification and easy complexation with naphthenic acid to produce corresponding ionic liquid-naphthenic acid complex, which is further separated from crude oil or fraction oil in the subsequent standing. The ionic liquid may be reused. The said process has high naphthenic acid eliminating rate up to 90 %, mild separation condition, low power consumption and less corrosion to the apparatus.
Description
Technical field
The present invention relates to the refining of petroleum field, particularly relate to a kind of method that removes naphthenic acid in crude oil or the distillate.
Background technology
In crude oil processing, refining industry, owing to contain oxygenatedchemicals in the crude oil, as naphthenic acid etc., it is very unfavorable to its time processing to make, can severe corrosion equipment, influence the security of refining process and the use properties of petroleum products.At present the acid stripping method that adopted of refinery have that alkali cleaning, ammonia are washed, mixing, hydrogenation and add method such as inhibiter crude oil and distillate are carried out depickling, but in deacidification, alkali wash need use a large amount of alkali lye, it is excessive to exist the alkali lye use, quantity of wastewater effluent is big, and the sepn process oil loss is big, separates not thorough, acid removal rate is low, shortcomings such as the easy emulsification of crude oil; And ammonia is washed method because a little less than the selected solvent alkalescence, low with the naphthenic acid reactive activity, the naphthenic acid acid number of acid removal rate and proposition is lower; Add inhibiter and mixing can not tackling the problem at its root; The hydrofining cost is bigger, and waste naphthenic acid resource.These methods also exist shortcomings such as solvent loss is big, agent/oil volume ratio is high, and quantity of wastewater effluent is big, and acid removal rate is low, and the sepn process oil loss is big in addition.
Ionic liquid (ionic liquids) is called ionic liquid at room temperature (room temperature ionicliquid), room temperature melting salt (room temperature molten salts), organic ion liquid etc. again, is meant only to be made up of ion to be the salt of liquid under room temperature or low temperature.Just found first ionic liquid---nitro ethamine as far back as 1914, but the progress in this field is slow thereafter, up to 1992, Wikes leader's research group synthesized low melting point, anti-hydrolysis, stable strong 1-ethyl-3-methyl imidazolium tetrafluoroborate ionic liquid ([emim] BF
4) after, ion liquid research is just developed rapidly, has developed a series of ion liquid system subsequently.Compare with ionogen with traditional organic solvent, ionic liquid has a series of outstanding advantages: (1) does not almost have vapour pressure, non-volatile, colourless, tasteless; (2) bigger equilibrium temperature scope is arranged, in the temperature range (100 ℃～200 ℃) of broadness, all be in liquid state, the electrochemical stability potential window of better chemical stability and broad; (3) can regulate its solvability by the design of zwitterion to inorganics, water, organism and polymkeric substance.
Summary of the invention
The purpose of this invention is to provide a kind of separation condition gentleness, simple, the method that remove in crude oil or distillate naphthenic acid little to the corrodibility of equipment.
The method that removes naphthenic acid in crude oil or the distillate provided by the present invention is that at least a ionic liquid and/or ancillary compound are joined in crude oil or the distillate, 20-80 ℃ of following hybrid reaction, leaves standstill, separates the crude oil or the distillate that obtain depickling;
Wherein, described ancillary compound is selected from the compound of formula I, formula II or formula III:
(formula I) (formula II) (formula III)
In the formula, the position of two nitrogen is for facing, position or contraposition in formula II and the formula III; R is a hydrogen, has the alkyl of 1-18 carbon atom, aryl or cycloalkyl.
Ancillary compound can be exemplified below: 1-Methylimidazole, 1-butyl imidazole, 1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline, 1-picoline and 2-ethylpyridine.
Ionic liquid with the compound of formula IV, formula V or formula VI as positively charged ion,
(formula IV) (formula V) (formula VI)
Wherein, Z is N or P; R
1, R
2, R
3, R
4, R
5Alkyl, alkoxyl group or aryl for 1-25 carbon atom;
Described ionic liquid with following ion as negatively charged ion: PF
6 -, Br
-, F
-, Cl
-, I
-, NO
3 -, AICl
4 -, BF
4 -, B (R
7)
4 -, R
7OSOC
3 -, R
7SO
4 -, R
7CO
2 -, R
7OPO
3 2-Or (R
7O) (R
8O) PO
2-R wherein
7, R
8Be respectively the alkyl or aryl of H, a 1-30 carbon atom.
Ionic liquid can be exemplified below: 1-ethyl-3 methylimidazole salt, 1-butyl-3-methylimidazole salt, L-Ala 4-butyl ammonium and chloro methyl butyl imidazoles.
In the methods of the invention, the mole dosage of ionic liquid or ancillary compound gets final product a little more than the naphthenic acid in crude oil or the distillate, with the mol ratio 1～2: 1 of naphthenic acid in crude oil or the distillate.
Also can reuse then with ionic liquid behind the acid-respons or ancillary compound, and can obtain wherein naphthenic acid in that reclaim the back with naphthenic acid separates through heating under 80-230 ℃.
Because ionic liquid and ancillary compound and crude oil and distillate have good mutual solubility, when the present invention adopts ionic liquid or ancillary compound to remove acidic cpd in crude oil or the distillate, be not easy to take place emulsification, and complexing takes place in easy and acid, generate corresponding ionic liquid-acid complex, through leave standstill can with crude oil or distillate layering, thereby realize separating with crude oil or distillate; Reclaim through obtaining regeneration after heating with the ionic liquid behind the crude separation, ionic liquid can be recycled; Naphthenic acid decreasing ratio height can reach about 90% in crude oil or the distillate; The sepn process mild condition, energy expenditure is low; Sepn process is not used has corrosive alkali lye, and oil loss is little, realizes clean separation, and little to the corrodibility of equipment.
Description of drawings
Fig. 1 removes the process flow sheet of naphthenic acid for the present invention.
Embodiment
The present invention adopts technical process that ionic liquid separates naphthenic acid in crude oil or the distillate as shown in Figure 1: ionic liquid and/or ancillary compound are mixed in reaction tower 1 with crude oil or distillate, temperature is controlled at 20-80 ℃, here can adopt the counter-current operation mode, also can adopt the mode of mixing, only need allow both fully contact and get final product; Then, the mixed solution that mixes pumped in the separating tank 2 leave standstill, from the bottom of separating tank 2 acidiferous ionic liquid is separated, remaining in the separating tank 2 promptly is depickling oil; And acidiferous ionic liquid enters in the regenerating tank 3, at 80-230 ℃ of following thermal regeneration, ionic liquid and/or ancillary compound are separated with naphthenic acid, thereby realize the recycle of ionic liquid and/or ancillary compound, naphthenic acid does not have destroyed in this process yet.
Among the present invention, ionic liquid can be selected broad variety, can constitute by a kind of positively charged ion and a kind of negatively charged ion or several cation and several negatively charged ion, the any ionic compound or the mixture that are being in a liquid state below 100 ℃, this ionic liquid and crude oil or distillate have solvability preferably, and the ionic liquid-acid complex that forms and crude oil or distillate do not dissolve each other.
Described ionic liquid with the compound of formula IV, formula V or formula VI as positively charged ion,
(formula IV) (formula V) (formula VI)
Wherein, Z is N or P; R
1, R
2, R
3, R
4, R
5Alkyl, alkoxyl group or aryl for 1-25 carbon atom;
Described ionic liquid with following ion as negatively charged ion: PF
6 -, Br
-, F
-, Cl
-, I
-, NO
3 -, AICl
4 -, BF
4 -, B (R
7)
4 -, R
7OSO
3 -, R
7SO
4 -, R
7CO
2 -, R
7OPO
3 2-Or (R
7O) (R
8O) PO
2-R wherein
7, R
8Be respectively the alkyl or aryl of H, a 1-30 carbon atom.
Ionic liquid commonly used comprises the imidazol ion of quaternary ammonium alkyl ion, alkyl quaternary phosphonium ion, alkyl replacement, the pyridinium ion that the N-alkyl replaces according to cation type; Be preferably the imidazol ion that alkyl replaces, as 1-butyl-3-methylimidazole salt, L-Ala 4-butyl ammonium and chloro methyl butyl imidazoles.
Employed ancillary compound can form liquid salt with acid among the present invention, this liquid salt is liquid under the temperature condition of crude oil hybrid reaction, promptly under this temperature in the process of separating liquid salt, formed liquid salt is not significantly decomposed, and the formed liquid salt of ancillary compound is immiscible with crude oil or distillate, form two immiscible liquid phases of separating, and formed salt can by the heating mode be easy to depickling, thereby return to original compound form.This compounds that can be used as ancillary compound contains nitrogen-atoms, for example at least one nitrogen-atoms.The molecular weight of ancillary compound is preferably less than the compound of 1000g/mol.
Ancillary compound can be an organism, also can be inorganics, preferred organism.
Described ancillary compound is selected from the compound of formula I, formula II or formula III:
(formula I) (formula II) (formula III)
In the formula, the position of two nitrogen is for facing, position or contraposition in formula II and the formula III; R can singly replace, and is polysubstituted, and wherein R is a hydrogen, has the alkyl of 1-18 carbon atom, aryl or cycloalkyl.
In addition, can use the mixture of ancillary compound or the target that solution reaches invention.Particularly preferred ancillary compound generally is lower than 150 ℃ with the fusing point of the salt that acid forms, and especially preferably is lower than 100 ℃.Preferred ancillary compound is 1 monomethyl imidazoles, 1-butyl imidazole, 1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline, 1-picoline, 2-ethylpyridine.
With [BM M] BF
4Mix in reaction tower with distillate, the mole dosage of imidazole derivative is 1.4 times of naphthenic acid mole number in the distillate, mixing temperature is 30 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 60 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 80 ℃ of heating 60 minutes again, and from the imidazole derivative that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 80%-85% of naphthenic acid in the distillate.
Embodiment 2: ionic liquid [EM M] PF
6(EM M represents 1-ethyl-3-Methylimidazole in the formula) and [BMM] BF
4Depickling
With ionic liquid imidazole derivative [EM M] PF
6With [BM M] BF
4In reaction tower 1, mix with crude oil according to mol ratio 1: 1, the mole dosage of imidazole derivative is 2 times of naphthenic acid mole number in the crude oil, mixing temperature is 100 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 30 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly a depickling crude oil.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 230 ℃ of heating 40 minutes again, and from the imidazole derivative that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 90%-98% of naphthenic acid in the crude oil.
Embodiment 3: ionic liquid [BM M] AlCl
4With [BM M] PF
6Depickling
With ionic liquid imidazole derivative [BM M] AlCl
4With [BM M] PF
6Mix with distillate counter current contact in reaction tower 1 according to mol ratio mixing in 0.5: 1, the imidazole derivative consumption equates with naphthenic acid molar content in the distillate, mixing temperature is 60 ℃, mixing time is 60 minutes, the liquid pumping that mixes was left standstill 40 minutes to separating tank 2, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 120 ℃ of heating 60 minutes again, and from the imidazole derivative that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 70%-80% of naphthenic acid in the distillate.
Embodiment 4:[BM M] AlCl
4With the depickling of 1-Methylimidazole
With [BM M] AlCl
4Mix at 1: 0.5 with distillate according to mol ratio with the 1-Methylimidazole and in reaction tower, to mix, the mole dosage of imidazole derivative is 1.4 times of naphthenic acid mole number in the distillate, mixing temperature is 30 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 60 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 80 ℃ of heating 60 minutes again, and from the imidazole derivative that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 85%-90% of naphthenic acid in the distillate.
Embodiment 5,1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline depickling
1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline is mixed in reaction tower with distillate, the mole dosage of 1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline is 2 times of naphthenic acid mole number in the distillate, mixing temperature is 60 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 60 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 140 ℃ of heating 60 minutes again, and from 1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 90%-95% of naphthenic acid in the distillate.
Embodiment 6, the depickling of 2-ethylpyridine
The 2-ethylpyridine is mixed in reaction tower with distillate, the mole dosage of 2-ethylpyridine is 2 times of naphthenic acid mole number in the distillate, mixing temperature is 40 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 60 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 120 ℃ of heating 60 minutes again, and from the 2-ethylpyridine that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 85%-90% of naphthenic acid in the distillate.
Embodiment 7,1-butyl imidazole and the depickling of 2-ethylpyridine
The 1-butyl imidazole mixed with distillate according to mol ratio with the 2-ethylpyridine at 1: 0.5 in reaction tower, mix, the mole dosage of mixture is 2 times of naphthenic acid mole number in the distillate, mixing temperature is 40 ℃, mixing time 60 minutes, the liquid pumping that mixes was left standstill 60 minutes to separating tank, bottom by separating tank will be separated with the ionic liquid behind the acid-respons, and the remainder in the separating tank is exactly the depickling distillate.The ionic liquid of separating is pumped in the regenerating tank, temperature is controlled at 120 ℃ of heating 60 minutes again, and from 1-butyl imidazole and 2-ethylpyridine that the regeneration abhiseca obtains reclaiming, a jar end obtains naphthenic acid.The extrusion rate 85%-90% of naphthenic acid in the distillate.
Claims (6)
1, a kind of method that removes naphthenic acid in crude oil or the distillate is that at least a ionic liquid and/or ancillary compound are joined in crude oil or the distillate, 20-80 ℃ of following hybrid reaction, leaves standstill, separates the crude oil or the distillate that obtain depickling;
Wherein, described ancillary compound and oil product have solvability preferably, and can form, fusing point immiscible with oil with acid and be lower than 150 ℃ ionic liquid, are selected from the compound of formula I, formula II or formula III:
(formula I) (formula II) (formula III)
In the formula, the position of two nitrogen is for facing, position or contraposition in formula II and the formula III; R can be single replacement, and is polysubstituted, and wherein R is hydrogen, has alkyl, aryl or a cycloalkyl of 1-18 carbon atom.
2, method according to claim 1 is characterized in that: described ancillary compound is selected from the 1-Methylimidazole, 1-butyl imidazole, 1-hydroxyethyl-2-cycloalkyl-2-tetrahydroglyoxaline, 1-picoline and 2-ethylpyridine.
3, method according to claim 1 is characterized in that: described ionic liquid comprises at least a positively charged ion and at least a negatively charged ion, be in a liquid state below 100 ℃, ionic liquid with the compound of formula IV, formula V or formula VI as positively charged ion,
(formula IV) (formula V) (formula VI)
Wherein, Z is N or P; R
1, R
2, R
3, R
4, R
5Alkyl, alkoxyl group or aryl for 1-25 carbon atom;
Described ionic liquid with following ion as negatively charged ion: PF
6 -, Br
-, F
-, Cl
-, I
-, NO
3 -, AICl
4 -, BF
4 -, B (R
7)
4 -, R
7OSO
3 -, R
7SO
4 -, R
7CO
2 -, R
7OPO
3 2-Or (R
7O) (R
8O) PO
2-R wherein
7, R
8Be respectively the alkyl or aryl of H, a 1-30 carbon atom.
4, method according to claim 3 is characterized in that: described ionic liquid is selected from 1-ethyl-3 methylimidazole salt, 1-butyl-3-methylimidazole salt, L-Ala 4-butyl ammonium and chloro methyl butyl imidazoles.
5, according to the arbitrary described method of claim 1-4, it is characterized in that: the mol ratio 1～2: 1 of naphthenic acid in ionic liquid or ancillary compound and crude oil or the distillate.
6, according to the arbitrary described method of claim 1-4, it is characterized in that: ionic liquid behind described and the acid-respons and/or ancillary compound also can under 80-230 ℃ through heating and naphthenic acid separates back recovery.
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|---|---|---|---|
| CNB200610075671XA CN100506949C (en) | 2006-04-18 | 2006-04-18 | Method of eliminating naphthenic acid from crude oil or fraction oil |
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|---|---|---|---|
| CNB200610075671XA CN100506949C (en) | 2006-04-18 | 2006-04-18 | Method of eliminating naphthenic acid from crude oil or fraction oil |
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| CN100506949C CN100506949C (en) | 2009-07-01 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101982525A (en) * | 2010-11-09 | 2011-03-02 | 中国海洋石油总公司 | Method for removing sulfides in gasoline by imidazolium ionic liquid |
| US20110155647A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for de-acidifying hydrocarbons |
| US20110155635A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from resid |
| US20110155637A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing nitrogen from vacuum gas oil |
| US20110155645A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from crude oil |
| US20110155638A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing sulfur from vacuum gas oil |
| US20110155644A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from vacuum gas oil |
| CN102597176A (en) * | 2009-06-22 | 2012-07-18 | 挪威国家石油公司 | Method for isolation and quantification of naphthenate forming acids ("ARN acids") in crude oil |
| US8574427B2 (en) | 2011-12-15 | 2013-11-05 | Uop Llc | Process for removing refractory nitrogen compounds from vacuum gas oil |
Family Cites Families (9)
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| US4634519A (en) * | 1985-06-11 | 1987-01-06 | Chevron Research Company | Process for removing naphthenic acids from petroleum distillates |
| US4752381A (en) * | 1987-05-18 | 1988-06-21 | Nalco Chemical Company | Upgrading petroleum and petroleum fractions |
| CN1032749C (en) * | 1993-02-26 | 1996-09-11 | 中国石化广州石油化工总厂 | Oil-removing purifying of crude naphthenic acid by amination |
| CN1063741C (en) * | 1995-07-21 | 2001-03-28 | 中国石化兰州炼油化工总厂 | Method for recovery of petroleum acids from mixed extract of isopropyl alcohol-ammonia water |
| FR2800090B1 (en) * | 1999-10-22 | 2003-03-21 | Elf Exploration Prod | PROCESS FOR DEACIDIFYING CRUDE OILS AND DEVICE FOR IMPLEMENTING SAME |
| US6642421B1 (en) * | 2000-04-18 | 2003-11-04 | Exxonmobil Research And Engineering Company | Method for isolating enriched source of conducting polymers precursors |
| MY138064A (en) * | 2002-01-24 | 2009-04-30 | Basf Ag | Method for the separation of acids from chemical reaction mixtures by means of ionic fluids |
| CN1235843C (en) * | 2004-03-12 | 2006-01-11 | 北京石油化工学院 | Method for eliminating and reclaiming acid component from oil products |
| CN100375739C (en) * | 2006-02-28 | 2008-03-19 | 中国科学院过程工程研究所 | Process of eliminating and recovering naphthenic acid from oil product |
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2006
- 2006-04-18 CN CNB200610075671XA patent/CN100506949C/en active Active
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|---|---|---|---|---|
| CN102597176A (en) * | 2009-06-22 | 2012-07-18 | 挪威国家石油公司 | Method for isolation and quantification of naphthenate forming acids ("ARN acids") in crude oil |
| CN102597176B (en) * | 2009-06-22 | 2015-11-25 | 挪威国家石油公司 | The method of acid (" ARN acid ") is formed for separating of with the naphthenate in quantitative crude oil |
| US8608952B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for de-acidifying hydrocarbons |
| US8580107B2 (en) * | 2009-12-30 | 2013-11-12 | Uop Llc | Process for removing sulfur from vacuum gas oil |
| US20110155645A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from crude oil |
| US20110155638A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing sulfur from vacuum gas oil |
| US20110155644A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from vacuum gas oil |
| US20110155635A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing metals from resid |
| US20110155647A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for de-acidifying hydrocarbons |
| US20110155637A1 (en) * | 2009-12-30 | 2011-06-30 | Uop Llc | Process for removing nitrogen from vacuum gas oil |
| US8608943B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing nitrogen from vacuum gas oil |
| US8608950B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing metals from resid |
| US8608951B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing metals from crude oil |
| US8608949B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing metals from vacuum gas oil |
| CN101982525A (en) * | 2010-11-09 | 2011-03-02 | 中国海洋石油总公司 | Method for removing sulfides in gasoline by imidazolium ionic liquid |
| US8574427B2 (en) | 2011-12-15 | 2013-11-05 | Uop Llc | Process for removing refractory nitrogen compounds from vacuum gas oil |
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Effective date of registration: 20170220 Address after: 100010 Beijing, Chaoyangmen, North Street, No. 25, No. Patentee after: China National Offshore Oil Corporation Patentee after: China National Offshore Oil Corporation Patentee after: CNOOC Refining & Chemical Research Institute (Beijing) Co., Ltd. Address before: 100027 Beijing city Dongcheng District Dongzhimen Street No. 6 Patentee before: China National Offshore Oil Corporation Patentee before: China National Offshore Oil and Gas Development and Utilization Co., Ltd. |
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Address after: 100010 Chaoyangmen North Street, Dongcheng District, Dongcheng District, Beijing Co-patentee after: China National Offshore Oil Corporation Patentee after: China Offshore Oil Group Co., Ltd. Co-patentee after: CNOOC Refining & Chemical Research Institute (Beijing) Co., Ltd. Address before: 100010 Chaoyangmen North Street, Dongcheng District, Dongcheng District, Beijing Co-patentee before: China National Offshore Oil Corporation Patentee before: China National Offshore Oil Corporation Co-patentee before: CNOOC Refining & Chemical Research Institute (Beijing) Co., Ltd. |
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