CN106867571A - A kind of high functionality parents notion crude oil metal-chelator and preparation method thereof - Google Patents
A kind of high functionality parents notion crude oil metal-chelator and preparation method thereof Download PDFInfo
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- CN106867571A CN106867571A CN201710152895.4A CN201710152895A CN106867571A CN 106867571 A CN106867571 A CN 106867571A CN 201710152895 A CN201710152895 A CN 201710152895A CN 106867571 A CN106867571 A CN 106867571A
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- 0 CCC([C@](C)/C(/*C(C(NC(C)C)=O)*(*)=C)=N/C1OC(C)*)OC(*)C1O Chemical compound CCC([C@](C)/C(/*C(C(NC(C)C)=O)*(*)=C)=N/C1OC(C)*)OC(*)C1O 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/205—Metal content
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- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention relates to prepare a kind of high functionality parents notion crude oil metal-chelator and preparation method thereof, the crude oil metal-chelator has good removal effect to metals such as Calcium in Crude Oil, iron, nickel, vanadium, it is to be obtained by carboxymethyl chitosan, N N-isopropylacrylamides and propene sulfonic acid class monomer graft copolymerization, its general structure is：Wherein, R is H or CH3；Number of repeat unit m is 100~1000, and degree of polymerization x is 2~500, and degree of polymerization y is 2~500.MOLECULE DESIGN and structure control that the crude oil metal-chelator passes through polymerized monomer and copolymer, using microwave radiation technology initiation grafting copolymerization green synthesis process, realize gathering and cooperateing with for various functional groups such as amino, amide groups, carboxyl, hydroxyl, sulfonic group, ether, isopropyl, the degree of functionality and hydrophilic and oleophilic for effectively increasing the metal-chelator are amphiphilic, and crude oil decalcifying rate reaches more than 80%, deferrization rate and reaches more than 75%, nickel removal rate and reach more than 30%, vanadium removal rate and reaches more than 35%.
Description
Technical field
The present invention relates to a kind of high functionality parents notion crude oil metal-chelator and preparation method thereof, it is adaptable to crude oil
In the metal such as calcium, iron, nickel, vanadium removing.
Background technology
Constantly increase recently as Global Oil consumption figure and conventional crude resource it is increasingly exhausted, people start by
Sight aims at that those working processes are more difficult but the relatively large number of non-conventional crude oil of reserves.However, tenor in non-conventional crude oil
Higher, based on calcium, iron, nickel, vanadium, they can damage catalytic cracking and catalytic hydrogenation in petroleum refining process to these metals
Catalyst, have serious damaging effect.Calcium in Crude Oil and the main presence in the form of naphthenate and phenates of iron；And nickel and vanadium
The main structure with porphyrin compound is present, and its structure is highly stable.Existing crude oil metal removal technology can mainly sum up
It is catalytic hydrogenation method, chemical precipitation method, metal deactivation method, chelating removal method and group technology etc..Wherein chelating removal method is utilized
Crude electric desalter, can simultaneously remove various metals, and equipment cost is low, removal effect is good, with good development prospect.Chela
Close removal method mainly to take by force from naphthenate or porphyrin compound by metals such as calcium, iron, nickel, vanadium by metal-chelator, turn
More stable chelate products soluble in water are melted into, then water-oil separating is carried out by the de- device of electricity, removing purpose is reached, so method
Amphipathic requirement to chelating agent is higher.
Existing metal-chelator mainly has inorganic acids, organic carboxyl acid class and containing phosphorus species etc..Inorganic acid pair sets
Strong corrosiveness is had, is progressively substituted；Organic carboxyl acid class metal remover is preferable to the removal effect of calcium and iron, but
Removal efficiency for nickel vanadium is very low；Although preferable to the removal effect of various metals containing phosphorus species, water body is easily caused
Eutrophication problem, does not meet the requirement of environmental protection.Chinese patent CN87105863A, CN1657594A using hydroxycarboxylic acid,
Monocarboxylic acid, dicarboxylic acids and amino acid are chelating agent, and with certain decalcification effect, but contained functional group is single, de- to nickel vanadium
Except effect is poor；The chelating removal method that Chinese patent CN102816586A, CN102443422 B are announced, with phosphoric acid, trimethyl phosphate
It is chelating agent with the phosphorus-containing compound such as dimethylphosphite, but scavenger is phosphorous, is not inconsistent cyclization to the removal effect of nickel vanadium preferably
Guaranteed request.Therefore, a kind of without phosphorus high functionality parents crude oil metal-chelator is invented, meets economic, social and environment instantly
Need.
The present invention is obtained a kind of high functionality parents copolymerization using the green synthesis process of microwave radiation technology initiation grafting copolymerization
Thing crude oil metal-chelator.
The content of the invention
Technical problem：It is an object of the invention to provide a kind of high functionality parents notion crude oil metal-chelator.The height
Degree of functionality parents notion crude oil metal-chelator is not phosphorous, is environment-friendly type metal scavenger；Introduced in chelator molecule
Carboxymethyl chitosan structure, is easily biodegradable, environment-friendly.
Technical scheme：A kind of high functionality parents notion crude oil metal-chelator of the invention is by carboxymethyl chitosan
Sugar, NIPA and the graft copolymerization of propene sulfonic acid class monomer are obtained, and its general structure is：
Wherein, R is H or CH3；Number of repeat unit m be 100~1000, degree of polymerization x be 2~500, degree of polymerization y be 2~
500。
A kind of preparation method of above-mentioned high functionality parents notion crude oil metal-chelator is：
At room temperature, in terms of the quality of carboxymethyl chitosan, by carboxymethyl chitosan, 10~30 times of carboxymethyl chitosan quality
Deionized water, the NIPA of 0.1~6 times of carboxymethyl chitosan quality be added in reactor, be uniformly dissolved
Lead to nitrogen afterwards, under 40~90 DEG C, blanket of nitrogen, first carry out microwave irradiation 2~20 minutes, the power of microwave is 90~800W, micro-
After amplitude is shone, then to 0.01~0.2 times of initiator of carboxymethyl chitosan quality, 0.01~0.2 times of carboxylic first of addition in reactor
After the sulfydryl class chain-transferring agent of base chitosan mass, 0.1~6 times of propene sulfonic acid class monomer of carboxymethyl chitosan quality is added dropwise,
The monomer is the aqueous solution of 10wt.%~25wt.%, is dripped off within 60~180 minutes, microwave reaction 5~30 minutes again after dripping off, instead
Should after be down to room temperature, obtain the high functionality parents notion crude oil metal-chelator that solid content is 20~60wt.%.
Propene sulfonic acid described in a kind of preparation method of above-mentioned high functionality parents notion crude oil metal-chelator
Class monomer is propene sulfonic acid or methacrylic sulfonic acid；Described sulfydryl class chain-transferring agent is mercaprol or mercaptopropionic acid；It is described
Initiator be azo dicyclohexyl formonitrile HCN or azo dicyano valeric acid.
Beneficial effect：A kind of high functionality parents notion crude oil metal-chelator of the invention has following superiority
Energy：
1st, the high functionality parents notion crude oil metal-chelator is not phosphorous, is environment-friendly type metal scavenger；Chela
Carboxymethyl chitosan structure is introduced in mixture molecule, is easily biodegradable, it is environment-friendly；
2nd, the present invention is prepared for containing amino, acid amides by the MOLECULE DESIGN to polymerized monomer and copolymer and structure control
High functionality parents' chelating agent that various functional groups such as base, carboxyl, hydroxyl, sulfonic group, ether, isopropyl gather.Amino, sulfonic acid
Base, ether, carboxyl, hydroxyl, amide groups are water-soluble good, chelatropic reaction, shape can occur with heavy metal in crude oil in oil-water interfaces
Into water-soluble products；Isopropyl oil-soluble is good, can improve the contact area of two-phase interface, so that metal removal effect is improved,
Can not only efficient removal calcium, iron, and can effectively remove nickel, vanadium；
3rd, the high functionality parents notion crude oil metal-chelator synthesis technique uses microwave assisting method, graft reaction rank
Microwave grafting pretreatment of the section to carboxymethyl chitosan makes it produce a large amount of grafting avtive spots, effectively increases graft reaction effect
Rate；Polymerization stage is polymerized using microwave radiation technology again, shortens reaction time, improve production efficiency；Reaction uses " one pot
Boil " synthetic method, without separating, production technology environmental protection, atom utilization is high.
Specific embodiment
Embodiment 1：At room temperature, 5g carboxymethyl chitosans, 150g deionized waters, 15g NIPAs are added
To in reactor, nitrogen is led to after being uniformly dissolved, under 80 DEG C, blanket of nitrogen, first carry out microwave irradiation 20 minutes, the power of microwave is
500W, after microwave irradiation, then to 0.5g azo dicyclohexyl formonitrile HCNs and 0.18g mercaprols is added in reactor after, be added dropwise
250g mass fractions are the propene sulfonic acid aqueous solution of 10wt.%, are dripped off within 180 minutes, microwave reaction 30 minutes, microwave again after dripping off
Power 400W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 25.3ppm, iron content 11.2ppm, nickel content
16.7ppm, content of vanadium 69.3ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 180ppm,
Decalcification rate is 87.5%, and deferrization rate is 77.8%, and nickel removal rate is 30.3%, and vanadium removal rate is 36.2%.
Embodiment 2：At room temperature, 10g carboxymethyl chitosans, 100g deionized waters, 6g NIPAs are added
To in reactor, nitrogen is led to after being uniformly dissolved, under 90 DEG C, blanket of nitrogen, first carry out microwave irradiation 5 minutes, the power of microwave is
90W, after microwave irradiation, then to 0.1g azo dicyano valeric acids and 0.5g mercaptopropionic acids is added in reactor after, 240g matter is added dropwise
Amount fraction is the methacrylic sulfonic acid aqueous solution of 25wt.%, is dripped off within 60 minutes, microwave reaction 10 minutes, microwave work(again after dripping off
Rate 100W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 25.8ppm, iron content 11.0ppm, nickel content
16.7ppm, content of vanadium 69.6ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 200ppm,
Decalcification rate is 84.1%, and deferrization rate is 78.1%, and nickel removal rate is 32.3%, and vanadium removal rate is 37.5%.
Embodiment 3：At room temperature, 24g carboxymethyl chitosans, 300g deionized waters, 60g NIPAs are added
Enter in reactor, nitrogen is led to after being uniformly dissolved, under 70 DEG C, blanket of nitrogen, first carry out microwave irradiation 15 minutes, the power of microwave
Be 200W, after microwave irradiation, then to 0.48g azo dicyclohexyl formonitrile HCNs and 0.24g mercaptopropionic acids is added in reactor after, drop
Plus 120g mass fractions are the propene sulfonic acid aqueous solution of 20wt.%, are dripped off within 120 minutes, microwave reaction 25 minutes again after dripping off are micro-
Wave power 600W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 24.4ppm, iron content 14.6ppm, nickel content
17.1ppm, content of vanadium 64.3ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 250ppm,
Decalcification rate is 88.7%, and deferrization rate is 78.5%, and nickel removal rate is 36.8%, and vanadium removal rate is 38.9%.
Embodiment 4：At room temperature, 8g carboxymethyl chitosans, 90g deionized waters, 48g NIPAs are added
To in reactor, nitrogen is led to after being uniformly dissolved, under 90 DEG C, blanket of nitrogen, first carry out microwave irradiation 2 minutes, the power of microwave is
800W, after microwave irradiation, then to 1.6g azo dicyano valeric acids and 1.6g mercaprols is added in reactor after, 200g matter is added dropwise
Amount fraction is the methacrylic sulfonic acid aqueous solution of 15wt.%, is dripped off within 90 minutes, microwave reaction 30 minutes, microwave work(again after dripping off
Rate 150W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 22.4ppm, iron content 11.3ppm, nickel content
18.7ppm, content of vanadium 67.8ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 210ppm,
Decalcification rate is 89.0%, and deferrization rate is 80.1%, and nickel removal rate is 31.4%, and vanadium removal rate is 37.1%.
Embodiment 5：At room temperature, 16g carboxymethyl chitosans, 200g deionized waters, 1.6g NIPAs are added
Enter in reactor, nitrogen is led to after being uniformly dissolved, under 60 DEG C, blanket of nitrogen, first carry out microwave irradiation 2 minutes, the power of microwave
Be 750W, after microwave irradiation, then to the isobutyl imidazoline of 3g azos two and 1.2g mercaptopropionic acids is added in reactor after, 160g is added dropwise
Mass fraction is the propene sulfonic acid aqueous solution of 20wt.%, is dripped off within 120 minutes, microwave reaction 5 minutes, microwave power again after dripping off
750W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 28.9ppm, iron content 10.2ppm, nickel content
16.7ppm, content of vanadium 68.3ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 150ppm,
Decalcification rate is 82.4%, and deferrization rate is 76.7%, and nickel removal rate is 30.1%, and vanadium removal rate is 35.6%.
Embodiment 6：At room temperature, 20g carboxymethyl chitosans, 320g deionized waters, 45g NIPAs are added
Enter in reactor, nitrogen is led to after being uniformly dissolved, under 40 DEG C, blanket of nitrogen, first carry out microwave irradiation 8 minutes, the power of microwave
Be 300W, after microwave irradiation, then to 0.8g azo dicyano valeric acids and 3g mercaprols is added in reactor after, 20g matter is added dropwise
Amount fraction is the methacrylic sulfonic acid aqueous solution of 10wt.%, is dripped off within 90 minutes, microwave reaction 20 minutes, microwave work(again after dripping off
Rate 700W.Room temperature is down to after reaction, light yellow clear high functionality parents notion crude oil metal-chelator is obtained.
With Oman's Basra mixed crude as test oil, its calcium content 28.6ppm, iron content 9.8ppm, nickel content
19.4ppm, content of vanadium 66.3ppm, when gained high functionality parents notion crude oil metal-chelator dosage is 230ppm,
Decalcification rate is 85.8%, and deferrization rate is 78.3%, and nickel removal rate is 33.1%, and vanadium removal rate is 40.3%.
The performance test methods of above-mentioned high functionality parents notion crude oil metal-chelator are：
Experiment crude oil used is Oman-Basra mixed crude, and (volume ratio of Oman's crude oil and Basra crude oil is 3:1
~1:3), the wherein content of calcium metal is 20~30ppm, and the content of metallic iron is 5~15ppm, the content of metallic nickel for 15~
25ppm, the content of vanadium metal is 60~70ppm.
40g crude oil is taken, is mixed with 2.8g deionized waters and 20ppm demulsifiers, 30min, Ran Hou are preheated at 80 DEG C
Stirred 5 minutes with the intensity of 1800r/min in agitator, be transferred in electrical desalter, according still further to crude quality 150~
250ppm adds crude oil metal-chelator.Technology of electric de-salting parameter is：125 DEG C of electro-desalting temperature, forceful electric power field intensity is
1200V/cm, the residence time is 10~15 minutes, and light current field intensity is 400V/cm, and the residence time is 5~10 minutes, during sedimentation
Between be 30 minutes.Gathered after profit is completely separated in electrical desalter it is de- after crude oil, after taking off in crude oil tenor analysis
Method referring to《Petrochemical Engineering Analysis method collects》In GB/T 508-1991 methods, pre-processed with dry ash method, gained ash content
Soaked with a small amount of distilled water, 3mL HCl solution (volume ratios 1 are added along the wall of cup of silica crucible：1)、10mL HNO3Solution
(volume ratio 1：1), in continue on temp.-regulating electric heating device slowly heated quartz crucible until ash content be completely dissolved, be evaporated up to solution
Remaining 2-3mL, color switchs to transparent, takes out cooling, gained sample is transferred in 25mL volumetric flasks, with distilled water by its constant volume
To 25mL.Measured using inductively coupled plasma emission spectrography (ICP-AES) calcium in above-mentioned prepared solution, iron,
The content of nickel, vanadium.
Crude oil demetallization per in terms of w, calculate decalcification rate, deferrization rate, nickel removal rate and vanadium removal rate by formula (1)：
Demetallization per w=[(X0-X1)/X0]×100 (1)
In formula：W-demetallization per, unit is %；
X0- before processing tenor, unit is μ g/g；
X1Tenor after-treatment, unit is μ g/g.
Claims (5)
1. a kind of high functionality parents notion crude oil metal-chelator, it is characterised in that the metal-chelator is by carboxymethyl chitosan
Sugar, NIPA and the graft copolymerization of propene sulfonic acid class monomer are obtained, and its general structure is：
Wherein, R is-H or-CH3；Number of repeat unit m is 100~1000, and degree of polymerization x is 2~500, and degree of polymerization y is 2~500.
2. a kind of a kind of preparation method of high functionality parents notion crude oil metal-chelator as claimed in claim 1, its
It is characterised by that the preparation method is：
Under room temperature, blanket of nitrogen, in terms of the quality of carboxymethyl chitosan, by carboxymethyl chitosan, 10~30 times of carboxymethyl chitosans
The deionized water of saccharic amount, the NIPA of 0.1~6 times of carboxymethyl chitosan quality are added in reactor, molten
40~90 DEG C are warming up to after solution is uniform, microwave irradiation is first carried out 2~20 minutes, the power of microwave is 90~800W, microwave irradiation
Afterwards, then to 0.01~0.2 times of organic initiators of carboxymethyl chitosan quality, 0.01~0.2 times of carboxymethyl of addition in reactor
After the sulfydryl class chain-transferring agent of chitosan mass, 0.1~6 times of propene sulfonic acid class monomer of carboxymethyl chitosan quality is added dropwise, should
Monomer is the aqueous solution of 10wt.%~25wt.%, is dripped off within 60~180 minutes, microwave reaction 5~30 minutes again after dripping off, reaction
After be down to room temperature, obtain the high functionality parents notion crude oil metal-chelator that solid content is 20~60wt.%.
3. the preparation method of a kind of high functionality parents notion crude oil metal-chelator according to claim 2, it is special
Levy is that propene sulfonic acid class monomer described in the preparation method is propene sulfonic acid or methacrylic sulfonic acid.
4. the preparation method of a kind of high functionality parents notion crude oil metal-chelator according to claim 2, it is special
Levy is that sulfydryl class chain-transferring agent described in the preparation method is mercaprol or mercaptopropionic acid.
5. the preparation method of a kind of high functionality parents notion crude oil metal-chelator according to claim 2, it is special
Levy is that organic initiators described in the preparation method are azo dicyclohexyl formonitrile HCN or azo dicyano valeric acid.
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