CN104710560B - A kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil - Google Patents
A kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil Download PDFInfo
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Abstract
The present invention relates to a kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil；The pour-point depressant is made up of dicyclopentadiene with Long Chain Alkyl Acrylate polymer and organic solvent, and based on gross weight 100%, the ratio of each component is：Dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil 3~25%, organic solvent 75~97%；Dicyclopentadiene and Long Chain Alkyl Acrylate polymer be by dicyclopentadiene and octadecyl acrylate, the ester of acrylic acid 20, Behenyl acrylate monoesters or mixed ester, it is that initiator carries out radical polymerization with azodiisobutyronitrile, dicyclopentadiene is 1 with the mol ratio of acrylate:10、3:10、1:2 and 1:1；This pour-point depressant adds dosage 100ppm pour-point depressant solids in crude oil, under treatment temperature is for 80 DEG C and static conditions, mixed crude condensation point can be reduced into 19 DEG C by 30 DEG C, and the viscosity break ratio at 29 DEG C is 93.9~95.1%.
Description
Technical field
The present invention is a kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil.It is related to general chemistry side
Method, the preparation of high molecular polymer and crude oil pipeline conveying technology field.
Background technology
In the development of recent decades, its species is continuously increased crude stream pour-point depressant, but all with molecular weight it is thousands of to 3~
Based on 50000 high molecular polymer, with alkene, acrylate, ethylene vinyl acetate, styrene, maleic anhydride（Maleic two
Acid）, acrylamide, the monomer such as acrylonitrile carry out polymerisation.Mainly have：Chinese Academy of Sciences's orchidization oil-soluble pour-point depressant, mainly
It is made up of high polymers such as polyisobutene, hydrogenated polyisoprene, ethylene-propylene block copolymers.A kind of use of Tianjin Normal University
Long Chain Alkyl Acrylate and the pour point depressant for crude oil of other copolymers synthesis.China Petroleum Pipeline Technological research center is Oilfield of Sudan
The pour-point depressant that piped oil is developed is containing Long Chain Alkyl Acrylate and ethene etc..Tianjin Normal University is with Dagang Oilfield joint research and development to big
Port crude oil by the pour-point depressant of efficient pour-point depressing process is constituted with Long Chain Alkyl Acrylate and maleic anhydride etc..CNPC day
One pour-point depressant patent of Ran Qi companies is by the special solvent preparation of the compoundings such as ethylene copolymer and Long Chain Alkyl Acrylate
Into.Petrochina transfering natural gas from the west to the east Shanghai branch and a kind of pour point depressant of petrochina pipeline scientific research center
Synthesis and pour point depression performance study.Tianjin Normal University is carried out with the Long Chain Alkyl Acrylate of synthesis with maleic anhydride, styrene
The pour-point depressant research experiment of ternary polymerization.Mink cell focus National Key Laboratory of China University Of Petroleum Beijing is with Shengli Oil Field to pour point depression of crude oil
The preparation research of agent ethylene-methyl acrylate copolymer.University Of Science and Technology Of Tianjin can make pour-point depressant by adjusting the chain length of higher alcohols
The research of different composition crude oil can be better adapted for.Shanghai engineering university is by common to acrylic acid high-carbon ester and vinylacetate etc.
The research that different series amine solution obtains a series of new pour point depressant is carried out after poly-.Liaoning Normal University is with metering system
Sour high-carbon ester styrene, maleic anhydride etc. are the development of the condensation point pour point depressant for crude oil high of raw material.Hubei University and Xiantao City
A kind of pour point depressant for crude oil by quadripolymers such as monomeric acrylic high-carbon alcohol esters of nine institute's joint research and developments.Jilin Institute of Chemical Technology grinds
The pour point depressant for crude oil with high-activity polyisobutene as primary raw material of system.China Petroleum Pipeline Technological research center is on domestic and international
The study mechanism of pour point depressant for crude oil pour-point depressing process.The amorphous ethylene-propylene of a kind of thermal cracking of German Texaco Inc.-non-conjugated
The patented technology of diene terpolymer pour-point depressant.Texaco Inc.'s drop of the application comprising ethylene-propylene-diene terpolymer
Coagulate patent of the additive as mineral oil pour-point depressant.One kind alkyl high of German Hirst company（Methyl）Acrylate and second
The copolymer of alkenyl monomer-ether, diester, pyrimidine or amino Gp. is used as pour point depressant for crude oil.French petroleum and natural gas companies
A kind of effect disquisition of polypropylene pour-point depressant in crude oil.Petrobras (Petroleo Brasileiro research center and Rio de Janeiro university develop
Use ethylene-vinyl acetate copolymer（EVA）As the wax inhibitor of Brazilian crude oil.France's carbonization and oil activated carbon company
A kind of stable emulsion for reducing condensation point of crude oil and suppress paraffin deposit of research and development, composition in emulsion with olefin copolymer/
Based on polypropylene.India's Pu Na cities Chemical Engineering in the presence of dicyclopentadiene is hydrogenated, is carried out with natural science laboratory
Research on polyacrylic intermiscibility, form, crystallization and dynamic mechanical.One kind of Ya Shilan oil companies of the U.S. is adopted
With tetrahydro-dicyclopentadiene and lower carbon number hydrocarbons, low-flash high density liquid hydrocarbon fuels etc. drop.Dicyclopentadiene above-mentioned is not
Apply in pour point depressant for crude oil.
The main chain of above-mentioned pour-point depressant is alkane, it is impossible to had containing special aromatic hydrocarbon and other ring-type chemicals with crude oil
Effect is acted on.This patent by studying the influence of anti-initiator, catalyst and reaction temperature to polymer, synthesis dicyclopentadiene with
Long Chain Alkyl Acrylate polymer.By reacting rate of heat release and conversion ratio in calorimeter research course of reaction, product is realized
Pilot scale and industrialized production.By field test, the crude oil pipeline of the products application that this patent is researched and developed to Chad is conveyed, real
Existing Chad's crude oil pipeline normal temperature, efficient and safe conveying.
The content of the invention
It is an object of the invention to provide a kind of to pour point depression of crude oil and the more preferable dicyclopentadiene of viscosity reduction and acrylic acid higher alcohols
Ester polymer pour point depressant for crude oil.The high molecular polymer in main chain contain 5 yuan of rings, can fully with crude oil in colloid in
Aromatic rings and other ring-type chemicals are acted on, and are improved containing colloid to the brilliant modified effect of crude oil wax.
The present invention is made up of dicyclopentadiene with Long Chain Alkyl Acrylate polymer and organic solvent, is in gross weight
The ratio of each component is in 100%：It is dicyclopentadiene and Long Chain Alkyl Acrylate polymer type crude oil pour-point depressant 3%~25%, organic
Solvent 75%~97%.
Wherein：Dicyclopentadiene is by dicyclopentadiene and octadecyl acrylate, third with Long Chain Alkyl Acrylate polymer
The monoesters or mixed ester of the ester of olefin(e) acid 20 and Behenyl acrylate, with azodiisobutyronitrile (AIBN) for initiator carries out freedom
Base is polymerized, and dicyclopentadiene is 1 with the mol ratio of acrylate:10、3:10、1:2 and 1:1.Acrylate is single methanol（C18 alcohol,
C20 alcohol, C22 alcohol）Or mixed alcohol, mixed alcohol ratio is C18 alcohol：C20 alcohol：C22 alcohol mol ratio is 1:1:1；1:2:1、2:2:1、3:
2:1.The weight average molecular weight Mw of polymer is 1*104~80*104。
Long Chain Alkyl Acrylate is prepared first：
25mL acrylic acid, 81.17g octadecyl alcolols, 0.9829g p-methyl benzenesulfonic acid are added toward the there-necked flask of 250mL（Catalysis
Agent）, 0.6881g hydroquinones（Polymerization inhibitor）With 50mL hexamethylenes, magneton is put into, loads onto reflux condensing tube and water knockout drum.Will be anti-
Answer device to be put into 125 DEG C of oil bath, stir, react 6 hours.After reaction terminates, will be reacted by the method for vacuum distillation and produced
Hexamethylene and unreacted acrylic acid in thing are extracted out.Above-mentioned product is octadecyl acrylate.The synthesis of the ester of acrylic acid 20 is needed
The alcohol added in above-mentioned synthesis is changed to 89.57g eicosanols.The synthesis of Behenyl acrylate need to be by addition in above-mentioned synthesis
Alcohol is changed to 97.98g docosanols.
The synthetic method of dicyclopentadiene and Long Chain Alkyl Acrylate polymer：
Dicyclopentadiene and Long Chain Alkyl Acrylate method for producing polymer：For dicyclopentadiene and acrylic acid higher alcohols
The acrylate of ester polymer synthesis is single methanol（C18 alcohol, C20 alcohol, C22 alcohol）, or mixed alcohol（C18 alcohol：C20 alcohol：C24 alcohol rubs
You are than being 1:1:1；1:2:1、2:2:1、3:2:1）Deng.Dicyclopentadiene is 1 with the molar ratio of Long Chain Alkyl Acrylate:10；
3:10；1:2 and 1:1.
The synthesis of dicyclopentadiene and octadecyl acrylate polymer：
Dicyclopentadiene is 1 with octadecyl acrylate mol ratio:Synthetic method when 10：Toward the there-necked flask of 250mL,
Add 25.000g octadecyl acrylates, 100mg azodiisobutyronitriles（AIBN）, 1.018g dicyclopentadienes, magneton, vacuumize-
Inflated with nitrogen three times, the toluene 25mL that addition flowed back, 65 DEG C of oil bath is polymerized 10 hours.
Dicyclopentadiene is 3 with octadecyl acrylate mol ratio:Synthetic method when 10：Toward the there-necked flask of 250mL,
Add 25.000g octadecyl acrylates, 120mg azodiisobutyronitriles（AIBN）, 3.055g dicyclopentadienes, magneton, vacuumize-
Inflated with nitrogen three times, the toluene 25mL that addition flowed back, 65 DEG C of oil bath is polymerized 10 hours.
Dicyclopentadiene is 1 with octadecyl acrylate mol ratio:Synthetic method when 2：Toward the there-necked flask of 250mL,
Add 25.000g octadecyl acrylates, 150mg azodiisobutyronitriles（AIBN）, 5.092g dicyclopentadienes, magneton, vacuumize-
Inflated with nitrogen three times, the toluene 25mL that addition flowed back, 65 DEG C of oil bath is polymerized 10 hours.
Dicyclopentadiene is 1 with octadecyl acrylate mol ratio:Synthetic method when 1：Toward the there-necked flask of 250mL,
Add 25.000g octadecyl acrylates, 200mg azodiisobutyronitriles（AIBN）, 10.185g dicyclopentadienes, magneton takes out true
Sky-inflated with nitrogen three times, the toluene 25mL that addition flowed back, 65 DEG C of oil bath is polymerized 10 hours.
Dicyclopentadiene is to be changed to the alcohol added in above-mentioned synthesis with the synthetic method of the ester polymer of acrylic acid 20
27.157g eicosanols.Dicyclopentadiene is that will be added in above-mentioned synthesis with the synthetic method of Behenyl acrylate polymer
Alcohol is changed to 27.157g docosanols.
The acrylic acid mixed ester method for producing polymer of dicyclopentadiene and different proportion：The alcohol that will be added in above-mentioned synthesis
Addition according to the form below
Organic solvent is：There are gasoline, diesel oil, or aromatic hydrocarbon solvent is such as：Dimethylbenzene, heavy aromatics, C9 aromatic hydrocarbons, C10 aromatic hydrocarbons.
The present invention is the mixture by above-mentioned high molecular polymer and organic solvent, and carboxylic acid is contained in organic polymer, can
Organic amine with colloid in crude oil, asphalitine is reacted.The present invention has improvement obvious to condensation point of crude oil and viscosity.
Specific embodiment
Embodiment 1.
(1) Long Chain Alkyl Acrylate first：
25mL acrylic acid, 81.17g octadecyl alcolols, 0.9829g p-methyl benzenesulfonic acid are added toward the there-necked flask of 250mL（Catalysis
Agent）, 0.6881g hydroquinones（Polymerization inhibitor）With 50mL hexamethylenes, magneton is put into, loads onto reflux condensing tube and water knockout drum.Will be anti-
Answer device to be put into 125 DEG C of oil bath, stir, react 6 hours.After reaction terminates, will be reacted by the method for vacuum distillation and produced
Hexamethylene and unreacted acrylic acid in thing are extracted out.Above-mentioned product is octadecyl acrylate.The synthesis of the ester of acrylic acid 20 is needed
The alcohol added in above-mentioned synthesis is changed to 89.57g eicosanols.The synthesis of Behenyl acrylate need to be by addition in above-mentioned synthesis
Alcohol is changed to 97.98g docosanols.
(2) synthetic method of dicyclopentadiene and Long Chain Alkyl Acrylate polymer：
Dicyclopentadiene is 3 with octadecyl acrylate mol ratio:Synthetic method when 10：Toward the there-necked flask of 250mL,
Add 8.329g octadecyl acrylates, the ester of 9.048g acrylic acid 20,9.766g Behenyl acrylates, 120mg azos two different
Butyronitrile（AIBN）, 3.055g dicyclopentadienes, magneton vacuumizes-inflated with nitrogen three times, the toluene 25mL that addition flowed back, oil bath
65 DEG C, it is polymerized 10 hours.
This pour point depressant for crude oil is adding dosage 100ppm pour-point depressants to Chad's crude oil mixed crude（Solid）, treatment temperature be 80
DEG C and static experiment under the conditions of, crude oil mixed crude condensation point can be reduced to 19 DEG C by 30 DEG C, the viscosity break ratio at 29 DEG C is
93.9%。
Embodiment 2.
(1) Long Chain Alkyl Acrylate first：
25mL acrylic acid, 81.17g octadecyl alcolols, 0.9829g p-methyl benzenesulfonic acid are added toward the there-necked flask of 250mL（Catalysis
Agent）, 0.6881g hydroquinones（Polymerization inhibitor）With 50mL hexamethylenes, magneton is put into, loads onto reflux condensing tube and water knockout drum.Will be anti-
Answer device to be put into 125 DEG C of oil bath, stir, react 6 hours.After reaction terminates, will be reacted by the method for vacuum distillation and produced
Hexamethylene and unreacted acrylic acid in thing are extracted out.Above-mentioned product is octadecyl acrylate.The synthesis of the ester of acrylic acid 20 is needed
The alcohol added in above-mentioned synthesis is changed to 89.57g eicosanols.The synthesis of Behenyl acrylate need to be by addition in above-mentioned synthesis
Alcohol is changed to 97.98g docosanols.
(2) synthetic method of dicyclopentadiene and Long Chain Alkyl Acrylate polymer：
Dicyclopentadiene is 1 with octadecyl acrylate mol ratio:Synthetic method when 2：Toward the there-necked flask of 250mL,
Add 6.247g octadecyl acrylates, the ester of 13.572g acrylic acid 20,7.325 Behenyl acrylates, 150mg azos two different
Butyronitrile（AIBN）, 5.092g dicyclopentadienes, magneton vacuumizes-inflated with nitrogen three times, the toluene 25mL that addition flowed back, oil bath
65 DEG C, it is polymerized 10 hours.
This pour point depressant for crude oil is adding dosage 100ppm pour-point depressants to Chad's crude oil mixed crude（Solid）, treatment temperature be 80
DEG C and static experiment under the conditions of, crude oil mixed crude condensation point can be reduced to 19 DEG C by 30 DEG C, the viscosity break ratio at 29 DEG C is
95.1%。
Embodiment 3.
(1) Long Chain Alkyl Acrylate first：
25mL acrylic acid, 81.17g octadecyl alcolols, 0.9829g p-methyl benzenesulfonic acid are added toward the there-necked flask of 250mL（Catalysis
Agent）, 0.6881g hydroquinones（Polymerization inhibitor）With 50mL hexamethylenes, magneton is put into, loads onto reflux condensing tube and water knockout drum.Will be anti-
Answer device to be put into 125 DEG C of oil bath, stir, react 6 hours.After reaction terminates, will be reacted by the method for vacuum distillation and produced
Hexamethylene and unreacted acrylic acid in thing are extracted out.Above-mentioned product is octadecyl acrylate.The synthesis of the ester of acrylic acid 20 is needed
The alcohol added in above-mentioned synthesis is changed to 89.57g eicosanols.The synthesis of Behenyl acrylate need to be by addition in above-mentioned synthesis
Alcohol is changed to 97.98g docosanols.
(2) synthetic method of dicyclopentadiene and Long Chain Alkyl Acrylate polymer：
Dicyclopentadiene is 1 with octadecyl acrylate mol ratio:Synthetic method when 1：Toward the there-necked flask of 250mL,
Add 9.995g octadecyl acrylates, the ester of 10.857g acrylic acid 20,5.860 Behenyl acrylates, 200mg azos two different
Butyronitrile（AIBN）, 10.185g dicyclopentadienes, magneton vacuumizes-inflated with nitrogen three times, the toluene 25mL that addition flowed back, oil bath
65 DEG C, it is polymerized 10 hours.
This pour point depressant for crude oil is adding dosage 100ppm pour-point depressants to Chad's crude oil mixed crude（Solid）, treatment temperature be 80
DEG C and static experiment under the conditions of, crude oil mixed crude condensation point can be reduced to 19 DEG C by 30 DEG C, the viscosity break ratio at 29 DEG C is
94.2%。
Application conditions：Contain a certain amount of gum asphalt crude oil with high solidifying point.Due to dicyclopentadiene and Long Chain Alkyl Acrylate
Polymer type crude oil pour-point depressant is to introduce caged scaffold on the main chain of high molecular polymer, is dicyclopentadiene high with acrylic acid
Carbon alcohol ester copoly type pour point depressant for crude oil, in main chain contain 5 yuan of rings, can fully with crude oil in colloid in aromatic rings and its
He acts on ring-type chemicals, improves containing colloid to the brilliant modified effect of crude oil wax.
The form of product：Product dissolves in alkane such as gasoline, diesel oil, or is dissolved in aromatic hydrocarbon such as dimethylbenzene, heavy aromatics, C9 virtues
Hydrocarbon, C10 aromatic hydrocarbons.
Claims (3)
1. the preparation method of a kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil, the dicyclopentadiene
With Long Chain Alkyl Acrylate polymer pour point depressant for crude oil by dicyclopentadiene and Long Chain Alkyl Acrylate polymer and organic solvent
Composition, based on gross weight 100%, the ratio of each component is：Dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depression of crude oil
Agent 3~25%, organic solvent 75%~97%, it is characterised in that：
1) Long Chain Alkyl Acrylate is prepared first：
Added toward the there-necked flask of 250mL 25mL acrylic acid, 81.17g octadecyl alcolols, 0.9829g p-methyl benzenesulfonic acid, 0.6881g pairs
Benzenediol and 50mL hexamethylenes, are put into magneton, load onto reflux condensing tube and water knockout drum；Reaction unit is put into 125 DEG C of oil bath
In, stirring is reacted 6 hours；After reaction terminates, by the method for vacuum distillation by the hexamethylene in product and unreacted
Acrylic acid is extracted out；Above-mentioned product is octadecyl acrylate；The synthesis of the ester of acrylic acid 20 need to change the alcohol added in above-mentioned synthesis
It is 89.57g eicosanols；The alcohol added in above-mentioned synthesis need to be changed to 97.98g docosanols by the synthesis of Behenyl acrylate；
2) synthetic method of dicyclopentadiene and Long Chain Alkyl Acrylate polymer：
Dicyclopentadiene is by dicyclopentadiene and octadecyl acrylate, acrylic acid 20 with Long Chain Alkyl Acrylate polymer
The monoesters or mixed ester of ester, Behenyl acrylate, are that initiator carries out radical polymerization, bicyclic penta 2 with azodiisobutyronitrile
Alkene is 1 with the mol ratio of acrylate:10、3:10、1:2 and 1:1.
2. the preparation side of dicyclopentadiene according to claim 1 and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil
Method, it is characterised in that：When acrylate is mixed ester, C18 alcohol：C20 alcohol：C22 alcohol mol ratio is 1:1:1、 1:2:1、2:2:1、
3:2:1。
3. the application of a kind of dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil, the dicyclopentadiene and third
Olefin(e) acid high-carbon ester polymer pour point depressant for crude oil is made up of dicyclopentadiene with Long Chain Alkyl Acrylate polymer and organic solvent,
Based on gross weight 100%, the ratio of each component is：Dicyclopentadiene and Long Chain Alkyl Acrylate polymer pour point depressant for crude oil 3~
25%th, organic solvent 75%~97%, it is characterised in that：As pour point depressant for crude oil, dosage 100ppm pour-point depressants are added in crude oil
Solid, under treatment temperature is for 80 DEG C and static conditions, can be reduced to 19 DEG C by mixed crude condensation point by 30 DEG C.
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| CN106468396A (en) * | 2016-08-28 | 2017-03-01 | 山东成泰化工有限公司 | A kind of petroleum pour depressant of hexahydro-phthalic acid two high-carbon alcohol ester |
| CN113307546B (en) * | 2021-04-09 | 2022-05-20 | 武汉市市政建设集团有限公司 | Durable ultrathin wearing layer and preparation method thereof |
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| US3499741A (en) * | 1966-08-12 | 1970-03-10 | Texaco Inc | Pour depressant composition |
| US3681302A (en) * | 1966-08-12 | 1972-08-01 | Texaco Inc | Pour depressant compositions of cracked ethylene/propylene/diene terpolymers |
| US3608231A (en) * | 1969-04-15 | 1971-09-28 | Texaco Inc | Pour depressant composition |
| DE3807394A1 (en) * | 1988-03-07 | 1989-09-21 | Henkel Kgaa | USE OF SELECTED COPOLYMER TYPES OF ACRYLIC AND / OR METHACRYLIC ACID ESTERS AS FLOW-IMPROVERS IN PARAFFIN-LIKE PETROLEUM AND PETROLEUM FRACTIONS (I) |
| CN1074037C (en) * | 1996-09-04 | 2001-10-31 | 中国科学院大连化学物理研究所 | Pour point reducer for high pour point crude oil |
| CN100349852C (en) * | 2005-08-29 | 2007-11-21 | 上海华谊丙烯酸有限公司 | A (methyl) higher aliphatic acrylate preparation method |
| CN101705138A (en) * | 2009-11-18 | 2010-05-12 | 济南开发区星火科学技术研究院 | Pour point depressant of lubricating oil and preparation method thereof |
| CN101845299B (en) * | 2010-05-17 | 2014-02-19 | 湖北大学 | Crude oil pour point depressant and preparation method thereof |
| CN102952233B (en) * | 2011-08-18 | 2015-05-20 | 中国石油化工股份有限公司 | Polymer used in lubricating oil pour point depressing, lubricating oil pour point depressant, and preparation method thereof |
| CN103184043A (en) * | 2013-02-28 | 2013-07-03 | 大连大学 | Crude oil pour point depressant and preparation method thereof |
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Effective date of registration: 20170124 Address after: 100007 Dongcheng District, Dongzhimen, China, North Street, No. 9 Oil Mansion, No. Applicant after: China National Petroleum Corporation Applicant after: China Petroleum Pipeline Bureau Engineering Co., Ltd. Address before: 100007 Dongcheng District, Dongzhimen, China, North Street, No. 9 Oil Mansion, No. Applicant before: China National Petroleum Corporation Applicant before: China Petroleum and Natural Gas Pipeline Bureau |
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Effective date of registration: 20190409 Address after: 100007 Oil Mansion, Oil Mansion, 9 Dongzhimen North Street, Dongcheng District, Beijing. Co-patentee after: China Petroleum Pipeline Bureau Engineering Co., Ltd. Patentee after: China National Petroleum Corporation Co-patentee after: Sino Oil King Shine Chemical Co., Ltd., Langfang Development Zone Address before: 100007 Oil Mansion, Oil Mansion, 9 Dongzhimen North Street, Dongcheng District, Beijing. Co-patentee before: China Petroleum Pipeline Bureau Engineering Co., Ltd. Patentee before: China National Petroleum Corporation |