CN108774544B - Oil product decolorizing agent - Google Patents

Oil product decolorizing agent Download PDF

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CN108774544B
CN108774544B CN201810740854.1A CN201810740854A CN108774544B CN 108774544 B CN108774544 B CN 108774544B CN 201810740854 A CN201810740854 A CN 201810740854A CN 108774544 B CN108774544 B CN 108774544B
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oil
surfactant
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CN108774544A (en
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常军君
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Yunnan Juzhong Energy Technology Co ltd
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Yunnan Juzhong Energy Technology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G29/00Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20Organic compounds not containing metal atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G29/00Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20Organic compounds not containing metal atoms
    • C10G29/22Organic compounds not containing metal atoms containing oxygen as the only hetero atom
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G29/00Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20Organic compounds not containing metal atoms
    • C10G29/22Organic compounds not containing metal atoms containing oxygen as the only hetero atom
    • C10G29/24Aldehydes or ketones
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G53/00Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • C10G53/02Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
    • C10G53/08Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one sorption step

Abstract

The invention relates to an oil product decolorizing agent, which comprises 100 weight parts of N-methyl pyrrolidone, 10-30 weight parts of 1, 3-diethyl acetonedicarboxylate, 1-20 weight parts of phenylmalonic acid and 10-30 weight parts of surfactant. According to the invention, the reaction of phenylmalonic acid and an alkaline compound is utilized, and the sulfonated polyimide can promote the adsorption of an acidic compound in an adsorption material. Respectively removing the acidic compound and the alkaline compound, thereby realizing high-efficiency decolorization.

Description

Oil product decolorizing agent
Technical Field
The present invention relates to a decoloring agent for oil products of circulating oil, common diesel, minus line, machine refining, etc.
Background
It is known that the gas oil produced in the thermal cracking and coking process has high content of unsaturated hydrocarbon and poor oil stability, and can not be directly used as finished product. Generally used as a catalytic cracking raw material or used as a blending component of internal combustion engine fuel after being hydrofined. Straight run gas oils are not sufficiently refined and often contain trace amounts of impurities such as gums, sulfur-, nitrogen-, or nitrogen-containing nonhydrocarbon compounds, and the like, resulting in darker products. During the storage of the diesel oil products, the color of the products is further deepened due to the chemical or physical action of impurities, so that the service performance of the oil products is reduced, and the appearance quality is poor, so that the diesel oil products are not favorable for sale.
The research on the cause of the discoloration of the oil products is more, and BattsB.D. and the like shows that the darkening of the color of the oil products is mainly the autooxidation of olefin to generate hydroperoxide, the hydroperoxide is the precursor for generating sediments, and the formation of the sediments is caused by the free radical principle. Acidic compounds with better solubility in oil products easily form soluble colloid under the catalytic action of non-basic nitrogen compounds such as pyrrole, indole and the like, so that the color of the oil products becomes dark. OpinderB.K. et al describe the mechanisms of oil color change and sediment formation, and it is believed that neutral nitride oxidation produces polar compounds, which are the main pathway for oil color deepening. The yellow Chong product et al (yellow Chong product, study of unstable components of heavy oil catalytic cracking light diesel oil. Petroleum institute (petroleum processing), 2001, 17 (6): 73-78) considers that the main components causing the color of the oil product to become dark are phenolic substances.
The acid washing and alkali washing method is the earliest developed decoloring technology, has mature process and comprises acid washing, alkali washing and acid and alkali combined refining method. The acid and base used commercially for decolorization are typically H2SO4 and NaOH. Yan macro, etc. (Yan macro, Huwen, alkali washing and stabilizing agent to raise the stability of diesel oil. oil refining design, 2000, 30 (5): 35-37) and the oil color is obviously improved by alkali washing with dilute alkali. Although the acid-base washing method has the characteristics of simple equipment and process, low investment and the like, the method generates a large amount of acid residues and alkaline residues and is easy to pollute the environment.
The colored substances in diesel oil are generally polar compounds containing hetero atoms such as sulfur, nitrogen or oxygen, and the adsorption method utilizes the strong adsorption effect of an adsorbent on the polar compounds to achieve the purpose of decolorization. Typical adsorbents are modified clays, bentonite, alumina, activated carbon, and the like. The Yasuhiro Shiraishi and the like investigate the adsorption and removal effects of the modified SiO2-Al2O3 on sulfides and nitrides in oil products, and the results show that the adsorbent can effectively reduce the contents of the sulfur and the nitrogen compounds in the oil products and improve the color of the oil products. The old and literature art, the research of removing basic nitrogen compounds in catalytic cracking diesel oil, the oil refining design, 2001, 31 (1): 52-54, researches the adsorption denitrification effect of the adsorption method on the nitrogen compounds in the oil products, and the result shows that the nitrogen compounds are removed through the adsorption effect, the color number of the oil products is reduced from 19 to 6, and meanwhile, the stability of the oil products is obviously improved.
The extraction method selectively removes colored substances from the oil product by utilizing the different solubility of certain solvents to colored components and colorless components in the oil product, thereby removing the color of the oil product. The solvent needs to meet the conditions of high selectivity on polar compounds such as sulfur, nitrogen, oxygen and the like in the oil product, low selectivity on saturated hydrocarbon, aromatic hydrocarbon and olefin, large density difference between the solvent oil and the oil product, low price and easy obtainment of the solvent and the like. Common solvents for oil product decolorization include methanol, ethanol, furfural, dimethyl sulfoxide, organic acids and the like. It is often difficult to achieve the desired effect with a single solvent.
The prior art lacks an oil product decolorizing agent which has simple process, convenient use, small dosage, low cost and high-efficiency decolorization.
Disclosure of Invention
In order to solve the technical problem, the invention provides an oil product decolorizing agent which comprises 100 parts by weight of N-methylpyrrolidone, 10-30 parts by weight of diethyl 1, 3-acetonedicarboxylate, 1-20 parts by weight of phenylmalonic acid and 10-30 parts by weight of surfactant.
As a preferred technical solution, the surfactant is a nonionic surfactant and/or an anionic surfactant.
As a preferable technical scheme, the anionic surfactant is benzene sulfonate with 8-16 alkyl carbon atoms or alkyl diphenyl ether disulfonate with 12-16 alkyl carbon atoms.
As a preferred technical scheme, the nonionic surfactant is a block copolymer of polyoxyethylene and polyoxypropylene.
As a preferable technical scheme, the oil product decolorizing agent also comprises a solid component, wherein the solid component comprises 2-40 parts by weight of adsorbed inorganic substance, 0.1-5 parts by weight of catalyst and 1-5 parts by weight of sulfonated polyimide.
As a preferable technical scheme, the adsorbed inorganic substance is one or more selected from activated carbon powder, CaOH powder, attapulgite particles, activated clay, bentonite and diatomite.
As a preferable technical scheme, the catalyst is selected from one or more of X-type molecular sieve catalyst, Y-type molecular sieve catalyst, mordenite molecular sieve catalyst and ZSM-5 molecular sieve catalyst.
As a preferable technical scheme, the polymerization degree of the sulfonated polyimide is 20-80.
As a preferable technical scheme, the mass ratio of the solid component to the N-methylpyrrolidone is 1: 5-10.
An oil product decoloring process, wherein the oil product dehydration process comprises the following steps:
heating the fuel oil to be decolorized to 70-80 ℃, and keeping the temperature constant;
under the constant temperature environment, adding 100 parts by weight of N-methyl pyrrolidone, 10-30 parts by weight of diethyl 1, 3-acetonedicarboxylate, 1-20 parts by weight of phenylmalonic acid and 10-30 parts by weight of surfactant into 4000 parts by weight of fuel oil to be decolorized, and stirring for 40-80 minutes at 70-80 ℃;
after separating the color phase, continuously adding 2-40 parts by weight of adsorbed inorganic substance, 0.1-5 parts by weight of catalyst and 1-5 parts by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
and cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product.
Since the basic compound and the acidic compound in the oil product can affect each other with the lapse of time, the chromaticity of the oil product can be greatly improved, so that it is particularly important to completely remove the basic compound and the acidic compound. According to the invention, the reaction of phenylmalonic acid and an alkaline compound is utilized, and the sulfonated polyimide can promote the adsorption of an acidic compound in an adsorption material. Respectively removing the acidic compound and the alkaline compound, thereby realizing high-efficiency decolorization.
The above-described and other features, aspects, and advantages of the present application will become more apparent with reference to the following detailed description.
Detailed Description
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control.
An oil product decolorizing agent is prepared from 100 parts by weight of N-methyl pyrrolidone, 10-30 parts by weight of 1, 3-diethyl acetonedicarboxylate, 1-20 parts by weight of phenylmalonic acid and 10-30 parts by weight of surfactant. The oil product decolorizing agent also comprises solid components, wherein the solid components comprise 2 to 40 weight parts of adsorbed inorganic substances, 0.1 to 5 weight parts of catalyst and 1 to 5 weight parts of sulfonated polyimide.
The adsorbed inorganic substance is selected from one or more of activated carbon powder, CaOH powder, attapulgite particles, activated clay, bentonite and diatomite.
The catalyst is selected from one or more of X-type molecular sieve catalyst, Y-type molecular sieve catalyst, mordenite molecular sieve catalyst and ZSM-5 molecular sieve catalyst.
Surfactant (b):
the surfactant of the present invention may be selected from nonionic surfactants and anionic surfactants.
In the present invention, the anionic surfactant may be polyoxyethylene alkyl ether sulfate, linear alkylbenzene sulfonate, alkyl sulfate, alcohol sulfate, secondary alkane sulfonate, α -olefin sulfonate, α -sulfo fatty acid ester salt, fatty acid polyoxyethylene ether sulfate, polyoxyethylene alkyl ether carboxylate, or the like.
For example, the linear alkylbenzene sulfonate is a benzene sulfonate having an alkyl group of 8 to 16 carbon atoms or an alkyl diphenyl ether disulfonate having 12 to 16 carbon atoms, and preferably, a benzene sulfonate having an alkyl group of 12 to 16 carbon atoms, for example, sodium dodecylbenzene sulfonate, potassium dodecylbenzene sulfonate, sodium tridecylbenzene sulfonate, sodium tetradecylbenzene sulfonate, sodium pentadecylbenzene sulfonate, sodium hexadecylbenzene sulfonate, sodium hexadecyldiphenyl ether disulfonate, and the like.
In one embodiment, the anionic surfactant is sodium hexadecylbenzene sulfonate.
In a preferred embodiment, the anionic surfactant is sodium hexadecyldiphenyloxide disulfonate.
For example, the alkyl sulfate is an alkyl sulfate having an alkyl group with 8 to 20 carbon atoms, such as sodium dodecyl sulfate, sodium tetradecyl sulfate, and sodium hexadecyl sulfate.
In one embodiment, the anionic surfactant is sodium lauryl sulfate.
For example, the alpha-olefin sulfonate is an alpha-olefin sulfonate having an alkyl group with 8 to 20 carbon atoms, such as sodium alpha-dodecene sulfonate, sodium alpha-hexadecene sulfonate, sodium alpha-octadecene sulfonate, and sodium alpha-eicosene sulfonate.
In one embodiment, the anionic surfactant is sodium alpha-tetradecene sulfonate.
For example, the polyoxyethylene alkyl ether sulfate is a polyoxyethylene alkyl ether sulfate having an alkyl group with 8 to 20 carbon atoms and an average number of moles of ethylene oxide added of 1 to 10.
The polyoxyethylene alkyl ether carboxylate is a polyoxyethylene alkyl ether carboxylate having an alkyl group with 8 to 20 carbon atoms and an average addition mole number of ethylene oxide of 1 to 10.
The nonionic surfactant in the present invention is preferably one having a melting point of 45 ℃ or higher. Examples of the nonionic surfactant include: higher alcohol ethylene oxide adducts, alkylphenol ethylene oxide adducts, fatty acid ethylene oxide adducts, polyol fatty acid ester ethylene oxide adducts, higher alkylamine ethylene oxide adducts, fatty acid alkanolamide ethylene oxide adducts, ethylene oxide adducts of fats and oils, block copolymers of polyoxyalkylene (block copolymers of polyoxyethylene. polyoxypropylene, block copolymers of polyoxyethylene. polyoxybutylene, block copolymers of polyoxyethylene. polyoxypropylene. polyoxybutylene, etc.), fatty acid esters of glycerin, fatty acid esters of pentaerythritol, fatty acid esters of sorbitol, fatty acid esters of sorbitan, fatty acid esters of sucrose, alkyl ethers of polyhydric alcohol, fatty acid amides of alkanolamides; and copolymers obtained by block addition polymerization of butylene oxide and/or propylene oxide to active hydrogen-containing compounds such as higher alcohols, alkylphenols, fatty acids, polyhydric alcohols, higher alkylamines, fatty acid amides, fats and oils, or fatty acid alkanolamides, followed by addition polymerization of ethylene oxide, but not limited thereto. These may be used alone or in combination of 2 or more.
In some embodiments, the nonionic surfactant is a block copolymer of polyoxyethylene polyoxypropylene having the structure:
R-O[(EO)a/(PO)b]-H
wherein R represents an alkyl group having 10 to 18 carbon atoms, preferably 12 to 14 carbon atoms; a represents a number of 0 to 20; b represents a number of 0 to 20; except for the case where both a and b are 0. a is preferably 6 to 15, more preferably 7 to 12, and b is preferably 0 to 10, more preferably 1 to 5, and particularly preferably 1 to 3.
In the present invention, the "EO" means an oxyethylene group; the "PO" refers to an oxypropylene group.
Sulfonated polyimide
The structural formula of the sulfonated polyimide is as follows:
Figure 100002_DEST_PATH_IMAGE002
wherein 0< b <1, n =20-80
For example, R1 may be:
Figure 100002_DEST_PATH_IMAGE004
for example, R2 may be:
Figure 100002_DEST_PATH_IMAGE006
x is
Figure DEST_PATH_IMAGE008
Or
Figure 864651DEST_PATH_IMAGE008
For example, R3 may be:
Figure DEST_PATH_IMAGE010
,
y is
Figure DEST_PATH_IMAGE012
Or
Figure DEST_PATH_IMAGE014
The preparation method of the sulfonated polyimide used in the invention is as follows:
(1) adding sulfonated diamine monomer, non-sulfonated diamine monomer, NMP and triethylamine into a dry three-necked bottle provided with a condenser pipe and a nitrogen inlet and outlet, stirring at room temperature and under a nitrogen atmosphere until the diamine monomer is completely dissolved, then adding equimolar 1, 4, 5, 8-naphthalic anhydride and 1-2 times of benzoic acid into a reaction bottle, heating the reaction system to 70-100 ℃, reacting for 2-10 hours at the temperature, then raising the temperature to 170-190 ℃, and reacting for 5-50 hours;
(2) and directly or diluting the obtained highly viscous sulfonated polyimide solution with m-cresol, precipitating the highly viscous sulfonated polyimide solution into acetone or ethyl acetate, washing the precipitated sulfonated polyimide solution with acetone or ethyl acetate for 1-3 times, and drying.
An oil product decoloring process, wherein the oil product dehydration process comprises the following steps:
heating the fuel oil to be decolorized to 70-80 ℃, and keeping the temperature constant;
under the constant temperature environment, adding 100 parts by weight of N-methyl pyrrolidone, 10-30 parts by weight of diethyl 1, 3-acetonedicarboxylate, 1-20 parts by weight of phenylmalonic acid and 10-30 parts by weight of surfactant into 4000 parts by weight of fuel oil to be decolorized, and stirring for 40-80 minutes at 70-80 ℃;
after separating the color phase, continuously adding 2-40 parts by weight of adsorbed inorganic substance, 0.1-5 parts by weight of catalyst and 1-5 parts by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
and cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product.
Since the basic compound and the acidic compound in the oil product can affect each other with the lapse of time, the chromaticity of the oil product can be greatly improved, so that it is particularly important to completely remove the basic compound and the acidic compound. According to the invention, the reaction of phenylmalonic acid and an alkaline compound is utilized, and the sulfonated polyimide can promote the adsorption of an acidic compound in an adsorption material. The acidic and basic compounds are removed separately.
Hereinafter, the present invention will be described in more detail by way of examples, but it should be understood that these examples are merely illustrative and not restrictive. The starting materials used are all commercially available, unless otherwise stated.
The present invention is described in detail below with reference to several examples.
Preparation of sulfonated polyimides
To a dry 100mL three-necked flask equipped with a condenser and nitrogen inlet and outlet was added 3.6mmol of 3, 3-bis (4-sulfophenoxy) benzidine, 0.4mmol of 9, 9-bis (4-aminophenyl) fluorene, 25mL of LNMP, and 1.22mL of triethylamine. After the diamine monomer was completely dissolved, 4.0mmol of 1, 4, 5, 8-naphthalenedicarboxylic anhydride and 0.693 g of benzoic acid were added. The reaction mixture was stirred at room temperature for 0.5 hour, then heated to 80 ℃ for 1 hour, and further heated to 180 ℃ for 3 hours. After the reaction, the obtained polymer solution was diluted with 20mL of nmmp, then slowly poured into 250mL of acetone to obtain a fibrous precipitate, filtered, washed with acetone several times, and dried under vacuum to obtain sulfonated polyimide (polymer 20).
Preparation of polyimide
To a dry 100mL three-necked flask equipped with a condenser and nitrogen inlet and outlet was added 4mmol9, 9-bis (4-aminophenyl) fluorene, 25mL NMMP and 1.22mL triethylamine. After the diamine monomer was completely dissolved, 4.0mmol of 1, 4, 5, 8-naphthalenedicarboxylic anhydride and 0.693 g of benzoic acid were added. The reaction mixture was stirred at room temperature for 0.5 hour, then heated to 80 ℃ for 1 hour, and further heated to 180 ℃ for 3 hours. After the reaction was completed, the resulting polymer solution was diluted with 20mL of nmmp, then poured slowly into 250mL of acetone to obtain a fibrous precipitate, filtered, washed with acetone several times, and dried under vacuum to obtain sulfonated polyimide (polymer 21).
Example 1
4000 parts by weight of minus line diesel oil with the color number of 5.1 is heated to 75 ℃, and the temperature is kept constant;
adding 100 parts by weight of N-methyl pyrrolidone, 20 parts by weight of diethyl 1, 3-acetonedicarboxylate, 5 parts by weight of phenylmalonic acid and 15 parts by weight of surfactant into minus line diesel oil under a constant temperature environment, and stirring for 60 minutes at 70-80 ℃;
after separating the color phase, continuously adding 20 parts by weight of activated clay, 0.5 part by weight of ZSM-5 molecular sieve catalyst and 3 parts by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
and cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product. The color number of the obtained fuel oil finished product is 1.4 and the yield of the oil product is 97.2 percent through detection.
Example 2
Heating 4000 parts by weight of machine-refined diesel oil with the color number of 5.8 to 75 ℃, and keeping the temperature constant;
adding 100 parts by weight of N-methyl pyrrolidone, 20 parts by weight of diethyl 1, 3-acetonedicarboxylate, 5 parts by weight of phenylmalonic acid and 15 parts by weight of surfactant into minus line diesel oil under a constant temperature environment, and stirring for 60 minutes at 70-80 ℃;
after separating the color phase, continuously adding 10 parts by weight of activated clay, 0.5 part by weight of ZSM-5 molecular sieve catalyst and 1 part by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
and cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product. The color number of the obtained fuel oil finished product is 1.3 through detection, and the oil product yield is 98.1%.
Example 3
Heating 4000 parts by weight of catalytic diesel oil with the color number of 5.5 to 75 ℃, and keeping the temperature constant;
adding 100 parts by weight of N-methyl pyrrolidone, 20 parts by weight of diethyl 1, 3-acetonedicarboxylate, 5 parts by weight of phenylmalonic acid and 15 parts by weight of surfactant into minus line diesel oil under a constant temperature environment, and stirring for 60 minutes at 70-80 ℃;
after separating the color phase, continuously adding 15 parts by weight of activated clay, 0.5 part by weight of ZSM-5 molecular sieve catalyst and 1 part by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
and cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product. The color number of the obtained fuel oil finished product is 1.5 through detection, and the oil product yield is 96.5%.
Comparative example 1
Same as in example 3, but 5 parts by weight of phenylmalonic acid were not added. The color number of the obtained fuel oil finished product is 2.2 and the yield of the oil product is 96.9 percent through detection.
Comparative example 2
The same as in example 3, but 1 part by weight of sulfonated polyimide was not added. The color number of the obtained fuel oil finished product is 2.4 and the yield of the oil product is 98.2 percent through detection.
Comparative example 3
As in example 3, 1 part by weight of sulfonated polyimide (degree of polymerization: 200) was added. The color number of the obtained fuel oil finished product is 2.8 and the yield of the oil product is 97.3 percent through detection.
Comparative example 4
As in example 3, 1 part by weight of polyimide (degree of polymerization: 21) was added. The color number of the obtained fuel oil finished product is 2.1 and the yield of the oil product is 97.6 percent through detection.
It can be seen that phenylmalonic acid and sulfonated polyimide play a very important role in the decolorization process.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. All equivalent changes and modifications made according to the disclosure of the present invention are covered by the scope of the claims of the present invention.

Claims (6)

1. The oil product decoloring process is characterized by comprising the following steps:
heating the fuel oil to be decolorized to 70-80 ℃, keeping the temperature constant, wherein the fuel oil to be decolorized contains an alkaline compound and an acidic compound;
under the constant temperature environment, adding 100 parts by weight of N-methyl pyrrolidone, 10-30 parts by weight of diethyl 1, 3-acetonedicarboxylate, 1-20 parts by weight of phenylmalonic acid and 10-30 parts by weight of surfactant into 4000 parts by weight of fuel oil to be decolorized, and stirring for 40-80 minutes at 70-80 ℃;
after separating the color phase, continuously adding 2-40 parts by weight of adsorbed inorganic substance, 0.1-5 parts by weight of catalyst and 1-5 parts by weight of sulfonated polyimide, heating to 120-150 ℃, stirring and decoloring for 1-3 hours;
cooling the decolorized fuel oil to room temperature, and filtering to obtain a fuel oil finished product;
the structural formula of the sulfonated polyimide is as follows:
Figure DEST_PATH_IMAGE001
wherein 0< b <1, n =20-80
R1 is:
Figure DEST_PATH_IMAGE002
r2 is:
Figure DEST_PATH_IMAGE003
x is
Figure DEST_PATH_IMAGE004
R3 is:
Figure DEST_PATH_IMAGE005
,
y is
Figure DEST_PATH_IMAGE006
Or
Figure DEST_PATH_IMAGE007
2. An oil decolorization process according to claim 1, characterized in that said surfactant is a nonionic surfactant and/or an anionic surfactant.
3. The oil product decoloring process according to claim 2, wherein the anionic surfactant is benzene sulfonate with C8-16 alkyl or alkyl diphenyl ether disulfonate with C12-16 alkyl.
4. The oil product decolorizing process of claim 2, characterized in that the nonionic surfactant is a block copolymer of polyoxyethylene and polyoxypropylene.
5. The oil decoloring process according to claim 1, wherein the adsorbed inorganic substance is selected from the group consisting of activated carbon powder, Ca (OH)2One or more of powder, attapulgite particles, activated clay, bentonite and diatomite.
6. An oil decolorization process according to claim 1, characterized in that said catalyst is selected from one or more of X-type molecular sieve catalyst, Y-type molecular sieve catalyst, mordenite molecular sieve catalyst, ZSM-5 molecular sieve catalyst.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1253992A (en) * 1998-11-16 2000-05-24 王福祥 Refining production process of off-colour diesel oil and coker diesel oil
CN102146297A (en) * 2011-03-04 2011-08-10 苏州久泰集团公司 Method for producing environmental-friendly aromatic oil
CN104805675A (en) * 2015-03-03 2015-07-29 上海彭港实业发展有限公司 Decolorizing agent
CN105778989A (en) * 2016-04-06 2016-07-20 成都天丰清洁能源发展有限公司 Crude diesel oil discoloring agent
CN106833719A (en) * 2017-03-08 2017-06-13 中国石油大学(北京) A kind of method of extract and separate crude oil
CN108003934A (en) * 2016-10-28 2018-05-08 中国石油化工股份有限公司 The method of deep desulfurization of gasoline and the equipment for deep desulfurization of gasoline

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1470606A (en) * 2003-06-23 2004-01-28 华东理工大学 Method for removing alkali-nitrogen compound from poor wax oil by complex extraction

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1253992A (en) * 1998-11-16 2000-05-24 王福祥 Refining production process of off-colour diesel oil and coker diesel oil
CN102146297A (en) * 2011-03-04 2011-08-10 苏州久泰集团公司 Method for producing environmental-friendly aromatic oil
CN104805675A (en) * 2015-03-03 2015-07-29 上海彭港实业发展有限公司 Decolorizing agent
CN105778989A (en) * 2016-04-06 2016-07-20 成都天丰清洁能源发展有限公司 Crude diesel oil discoloring agent
CN108003934A (en) * 2016-10-28 2018-05-08 中国石油化工股份有限公司 The method of deep desulfurization of gasoline and the equipment for deep desulfurization of gasoline
CN106833719A (en) * 2017-03-08 2017-06-13 中国石油大学(北京) A kind of method of extract and separate crude oil

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