CN107759485A - A kind of methacrylate monomers for being used to prepare coking inhibitor component - Google Patents

A kind of methacrylate monomers for being used to prepare coking inhibitor component Download PDF

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Publication number
CN107759485A
CN107759485A CN201610675417.7A CN201610675417A CN107759485A CN 107759485 A CN107759485 A CN 107759485A CN 201610675417 A CN201610675417 A CN 201610675417A CN 107759485 A CN107759485 A CN 107759485A
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CN
China
Prior art keywords
positive
coking inhibitor
prepare
inhibitor component
methacrylate monomers
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Pending
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CN201610675417.7A
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Chinese (zh)
Inventor
李洪波
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Tianjin Mingrui Petroleum Science And Technology Co Ltd
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Tianjin Mingrui Petroleum Science And Technology Co Ltd
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Priority to CN201610675417.7A priority Critical patent/CN107759485A/en
Publication of CN107759485A publication Critical patent/CN107759485A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups

Abstract

The invention discloses a kind of methacrylate monomers for being used to prepare coking inhibitor component, its preparation method comprises the following steps：S1：The cloroecther that total carbon number is 18 40 is synthesized by Williamson ether synthetic methods as raw material using positive structure C14 C22 carbon alcohol with the positive C4 C18 alkane of end position dichloro substitution；S2：Cloroecther and NH3 reaction synthesis primary amine；S3：Primary amine synthesizes N Methacrylamides with methacrylic acid by polycondensation reaction；The positive structure C14 C22 carbon alcohol is positive ten four carbon alcohols, positive 16 carbon alcohol, positive octadecanol, positive eicosanol or positive two Lauryl Alcohol, and the positive C4 C16 alkane is normal butane, pentane, n-hexane, normal heptane, normal octane, n -nonane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecane, hexadecane, n-heptadecane or n-octadecane.The present invention can be used in preparing coking inhibitor component, and combined coefficient is high, and cost is low.

Description

A kind of methacrylate monomers for being used to prepare coking inhibitor component
Technical field
The present invention relates to coking inhibitor component technical field, more particularly to a kind of it is used to prepare coking inhibitor component Methacrylate monomers.
Background technology
With the increasingly intensification of petroleum heavyization and society to product demand lighting contradiction, the original of petroleum refining and processing Material is increasingly heavier, and quality is worse and worse；Feedstock oil change brings many unthinkable to petroleum refining and petrochemical industry processing again Difficulty, such as residual hydrocracking, catalytic cracking, hydrodesulfurization, the relevant device of coking device, as heat exchanger, furnace tubing, Reactor, reboiler etc., it is easy to form coking and incrustation, decline heat exchanger efficiency, pipeline blocking, had a strong impact on device Operation and operation；At present, the method for solving problems mainly has two kinds：One kind is to change Machine Design and technological process； Another kind is exactly to use coking and fouling inhibitor；And for the device for having run and having built up at present, first method is It is unpractical；The chemical method of coking inhibitor is added, in the case where not changing technological process, do not influence normal production, Minimal amount of chemical assistant is directly added into work fluid, so as to play the work for suppressing, delaying, removing coking and fouling generation With this method is undoubtedly economic and practical.
Coking Mechanism mainly has the following aspects：
1st, radical reaction green coke；The other factorses of micro oxygen or energy stimulating activity free radical trigger working substance in the logistics that works Polymerisation occurs for alkene, aldehyde ketone, aromatic hydrocarbons in stream etc., forms macromolecule polyalcohol and is further formed insoluble in working media Material, it is deposited on equipment surface.
2nd, on-catalytic green coke；Alkadienes, colloid, asphalitine in working media such as high temperature, high pressure under working condition Generation dehydrogenative condensation forms condensation polymer or small char particle, and it can further produce bigger Jiao as the core of coking（Dirt） Separate out.
3rd, metal catalytic green coke；If working media and the metal on relevant device surface are deposited in the form of ion and complex When, catalytic action can be played to Raolical polymerizable, exacerbate the Raolical polymerizables such as alkene, aldehyde ketone, aromatic hydrocarbons, formed It is insoluble in the material of working media.
4th, work inorganic salts that logistics Central Plains has and formed in accumulating, process, coke fines, catalyst dust etc. is poly- Collection is formed burnt or dirty.
5th, coagulation effect is accelerated after the mutually absorption such as catalyst dust, organic polymer, inorganic salts.
Therefore, it is proposed that a kind of methacrylate monomers for being used to prepare coking inhibitor component.
The content of the invention
Based on technical problem existing for background technology, the present invention proposes a kind of first for being used to prepare coking inhibitor component Base acrylate monomer.
A kind of methacrylate monomers for being used to prepare coking inhibitor component proposed by the present invention, the monomer structure lead to Formula is：
R is the normal chain alkyl that carbon number is 14,16,18,20 or 22 in the formula, n=4-18；
Its preparation method comprises the following steps：
S1：Synthesized using positive structure C14-C22 carbon alcohol with the positive C4-C18 alkane of end position dichloro substitution as raw material by Williamson ethers Method synthesizes the cloroecther that total carbon number is 18-40：
；
S2：Cloroecther and NH3 reaction synthesis primary amine：
；
S3：Primary amine synthesizes N methacrylamide with methacrylic acid by polycondensation reaction：
。
Preferably, the positive structure C14-C22 carbon alcohol is positive ten four carbon alcohols, positive 16 carbon alcohol, positive octadecanol, positive 20 carbon Alcohol or positive two Lauryl Alcohol, the positive C4-C16 alkane are normal butane, pentane, n-hexane, normal heptane, normal octane, n -nonane, just Decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecane, hexadecane, n-heptadecane or positive 18 Alkane.
Preferably, the N methacrylamide synthesizes coking inhibitor component with olefinic monomer copolyreaction.
Preferably, when in the equipment that coking inhibitor is applied to PETROLEUM PROCESSING and refining, the addition of coking inhibitor For 10-1000ppm, and coking inhibitor reaches optimum efficiency with dispersant and antioxidant compounding.
Preferably, the coking inhibitor is applied to the production and processing process of diesel oil, lubricating oil and residual oil, including hydrogenation Heat exchanger, boiler tube, tower and consersion unit during desulfurization, catalytic cracking, hydrofinishing, alkylation, coking.
In the present invention, the positive C4-C18 alkane substituted by positive structure C14-C22 carbon alcohol with end position dichloro is Material synthesis total carbon Number is 18-40 cloroecther, and by cloroecther and NH3 reaction synthesis primary amine, N- is synthesized with metering system acid reaction by primary amine Methacrylamide, the present invention can be used in preparing coking inhibitor component, and combined coefficient is high, and cost is low.
Embodiment
The present invention is made with reference to specific embodiment further to explain.
Embodiment
The present embodiment proposes a kind of methacrylate monomers for being used to prepare coking inhibitor component, the monomer structure Formula is：
R is the normal chain alkyl that carbon number is 14,16,18,20 or 22 in the formula, n=4-18；
Its preparation method comprises the following steps：
S1：Synthesized using positive structure C14-C22 carbon alcohol with the positive C4-C18 alkane of end position dichloro substitution as raw material by Williamson ethers Method synthesizes the cloroecther that total carbon number is 18-40：
；
S2：Cloroecther and NH3 reaction synthesis primary amine：
；
S3：Primary amine synthesizes N methacrylamide with methacrylic acid by polycondensation reaction：
。
In the present embodiment, the positive structure C14-C22 carbon alcohol is positive ten four carbon alcohols, positive 16 carbon alcohol, positive octadecanol, positive two Ten carbon alcohol or positive two Lauryl Alcohol, the positive C4-C16 alkane is normal butane, pentane, n-hexane, normal heptane, normal octane, positive nonyl Alkane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecane, hexadecane, n-heptadecane or just Octadecane, the N methacrylamide synthesize coking inhibitor component with olefinic monomer copolyreaction, when coking inhibitor should During in PETROLEUM PROCESSING and the equipment of refining, the addition of coking inhibitor is 10-1000ppm, and coking inhibitor is with dividing Powder and antioxidant compounding reach optimum efficiency, and the coking inhibitor is applied to diesel oil, the production of lubricating oil and residual oil and place Heat exchanger, boiler tube, tower during reason process, including hydrodesulfurization, catalytic cracking, hydrofinishing, alkylation, coking and Consersion unit, the positive C4-C18 alkane substituted by positive structure C14-C22 carbon alcohol with end position dichloro is that the total carbon number of Material synthesis is 18-40 Cloroecther, by cloroecther and NH3 reaction synthesis primary amine, N- methacryls are synthesized with metering system acid reaction by primary amine Amine, the present invention can be used in preparing coking inhibitor component, and combined coefficient is high, and cost is low.
Example 1：N- metering systems-(4- hexadecane epoxides)-butyramide
（1）Prepare 4- chlorobutyl cetyl ethers：
Sequentially added in 1000mL four-hole bottles the positive hexadecanols of 121.2g (0.5mol), 24.0g (0.6mol) sodium hydroxide powder, 650mL dimethyl sulfoxides, stirring makes well dispersed, is heated slowly to 83 DEG C afterwards, obtains the alcohol sodium solution of light yellow clarification, cools It is standby to 50 DEG C.
76.2g (0.6mol) Isosorbide-5-Nitrae-dichloroetane and 200mL dimethyl sulfoxides are added in 2000mL four-hole bottles, stirring is lower to be added Heat is to 45 DEG C, and self-heat conserving funnel is slowly added into above-mentioned alcohol sodium solution, and 40 ~ 45 DEG C of keeping temperature during dropwise addition, 3h is dripped off, Zhi Houbao Temperature stirring 3.5h, 60 DEG C of 800mL water is slowly instilled under then stirring, oil reservoir is separated while hot, 60 DEG C of hot washes, obtains sticky Grease, yield 89.3%.
（2）Prepare positive 20 ether amines of 4- epoxides：
The above-mentioned cloroecthers of 133.2g (0.4mol) and 780mL dimethyl sulfoxides are added in 2000mL four-hole bottles, with 10ml/min's Speed is slowly introducing NH3, and 86 DEG C are heated to after stirring at normal temperature 30min, adds water 500mL after insulated and stirred 12h, separates oil while hot Layer, obtains sticky grease, yield 90.6% after washing.
（3）Prepare N- metering systems-(4- hexadecane epoxides)-butyramide：
Sequentially added in 2000mL four-hole bottles the above-mentioned ether amines of 125.4g (0.4mol), 43.0 (0.5mol) g methacrylic acids and 700mL dimethyl sulfoxides, are heated to 78 DEG C after stirring at normal temperature 30min, after insulated and stirred 12h plus water 500mL, separate oil reservoir while hot, Sticky grease, yield 93.1% are obtained after washing.
Example 2：Prepare N- metering systems-(4- eicosane epoxides)-butyramide
By example 1 method, higher alcohols are changed to positive eicosanol, cloroecther yield is 85.6%；Primary amine yield 88.1%；N- methyl Acrylamide yield is 90.5%.
Example 3：Prepare N- metering systems-(6- tetradecyloxyanilines)-caproamide
By example 1 method, higher alcohols are changed to tetradecanol, dichloro alkanes are changed to 1,6- dichloro n-hexanes, cloroecther is received Rate is 74.8%；Primary amine yield 85.1%；N methacrylamide yield is 83.2%.
Example 4：Prepare N- metering systems-(6- octadecane epoxides)-caproamide
By example 1 method, higher alcohols are changed to positive octadecyl alcolol, dichloro alkanes are changed to 1,6- dichloro n-hexanes, cloroecther is received Rate is 71.8%；Primary amine yield 83.1%；N methacrylamide yield is 83.4%.
Example 5：Prepare N- metering systems-(8- tetradecyloxyanilines)-caprylamide
By example 1 method, higher alcohols are changed to tetradecanol, dichloro alkanes are changed to 1,8- dichloro normal octanes, cloroecther is received Rate is 79.1%；Primary amine yield 86.3%；N methacrylamide yield is 88.5%.
Example 6：Prepare N- metering systems-(10- hexadecane epoxides)-decyl amide
By example 1 method, higher alcohols are changed to positive hexadecanol, dichloro alkanes are changed to 1,10- dichloro n-decanes, cloroecther is received Rate is 81.1%；Primary amine yield 87.3%；N methacrylamide yield is 83.5%.
Example 7：Prepare N- metering systems-(12- octadecane epoxides)-lauramide
By example 1 method, higher alcohols are changed to positive octadecyl alcolol, dichloro alkanes are changed to 1,12- dichloro n-dodecanes, cloroecther Yield is 77.1%；Primary amine yield 87.5%；N methacrylamide yield is 83.5%.
Example 8：Prepare N- metering systems-(14- eicosane epoxides)-myristamide
By example 1 method, higher alcohols are changed to positive eicosanol, dichloro alkanes are changed to 1,14- dichloro n-tetradecanes, cloroecther Yield is 81.1%；Primary amine yield 82.3%；N methacrylamide yield is 86.5%.
Example 9：Prepare N- metering systems-(16- docosane epoxide)-palmitamide
By example 1 method, higher alcohols are changed to positive docosanol, dichloro alkanes are changed to 1,16- dichloro hexadecanes, chloro Ether yield is 77.4%；Primary amine yield 82.9%；N methacrylamide yield is 86.7%.
The foregoing is only a preferred embodiment of the present invention, but protection scope of the present invention be not limited thereto, Any one skilled in the art the invention discloses technical scope in, technique according to the invention scheme and its Inventive concept is subject to equivalent substitution or change, should all be included within the scope of the present invention.

Claims (5)

  1. A kind of 1. methacrylate monomers for being used to prepare coking inhibitor component, it is characterised in that the monomer structure formula For：
    R is the normal chain alkyl that carbon number is 14,16,18,20 or 22 in the formula, n=4-18；
    Its preparation method comprises the following steps：
    S1：Synthesized using positive structure C14-C22 carbon alcohol with the positive C4-C18 alkane of end position dichloro substitution as raw material by Williamson ethers Method synthesizes the cloroecther that total carbon number is 18-40：
    ；
    S2：Cloroecther and NH3 reaction synthesis primary amine：
    ；
    S3：Primary amine synthesizes N methacrylamide with methacrylic acid by polycondensation reaction：
    。
  2. 2. a kind of methacrylate monomers for being used to prepare coking inhibitor component according to claim 1, its feature It is, the positive structure C14-C22 carbon alcohol is positive ten four carbon alcohols, positive 16 carbon alcohol, positive octadecanol, positive eicosanol or positive 20 Two carbon alcohol, the positive C4-C16 alkane is normal butane, pentane, n-hexane, normal heptane, normal octane, n -nonane, n-decane, positive ten One alkane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecane, hexadecane, n-heptadecane or n-octadecane.
  3. 3. a kind of methacrylate monomers for being used to prepare coking inhibitor component according to claim 1, its feature It is, the N methacrylamide synthesizes coking inhibitor component with olefinic monomer copolyreaction.
  4. 4. a kind of methacrylate monomers for being used to prepare coking inhibitor component according to claim 3, its feature It is, when in the equipment that coking inhibitor is applied to PETROLEUM PROCESSING and refining, the addition of coking inhibitor is 10- 1000ppm, and coking inhibitor reaches optimum efficiency with dispersant and antioxidant compounding.
  5. 5. a kind of methacrylate monomers for being used to prepare coking inhibitor component according to claim 3, its feature It is, the coking inhibitor is applied to the production and processing process of diesel oil, lubricating oil and residual oil, including hydrodesulfurization, catalysis Heat exchanger, boiler tube, tower and consersion unit during cracking, hydrofinishing, alkylation, coking.
CN201610675417.7A 2016-08-17 2016-08-17 A kind of methacrylate monomers for being used to prepare coking inhibitor component Pending CN107759485A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111004116A (en) * 2019-12-19 2020-04-14 湖北美和科技有限公司 Methacrylate monomer for preparing coking inhibitor component
CN112961715A (en) * 2021-03-02 2021-06-15 四川大学 Preparation method and application of novel hydrocarbon fuel coking inhibitor

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0117530A1 (en) * 1983-02-28 1984-09-05 Texaco Development Corporation Production of N-substituted (meth)acrylamides from (meth)acrylates and amines over a metal alkoxide catalyst
JPS60190746A (en) * 1984-03-12 1985-09-28 Mitsui Toatsu Chem Inc Aliphatic n-substituted unsaturated amide compound and preparation thereof
CN1041605A (en) * 1988-10-06 1990-04-25 B.F.谷德里奇公司 Polyacrylate polymers with utilizing substituted urea retarder
EP0619295A1 (en) * 1992-10-21 1994-10-12 KOHJIN CO. Ltd. Process for producing n-monosubstituted (meth)acrylamyde
CN1308117A (en) * 2000-11-29 2001-08-15 中国石油化工集团公司 Coking and scaling inhibitor and its preparation and application

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0117530A1 (en) * 1983-02-28 1984-09-05 Texaco Development Corporation Production of N-substituted (meth)acrylamides from (meth)acrylates and amines over a metal alkoxide catalyst
JPS60190746A (en) * 1984-03-12 1985-09-28 Mitsui Toatsu Chem Inc Aliphatic n-substituted unsaturated amide compound and preparation thereof
CN1041605A (en) * 1988-10-06 1990-04-25 B.F.谷德里奇公司 Polyacrylate polymers with utilizing substituted urea retarder
EP0619295A1 (en) * 1992-10-21 1994-10-12 KOHJIN CO. Ltd. Process for producing n-monosubstituted (meth)acrylamyde
CN1308117A (en) * 2000-11-29 2001-08-15 中国石油化工集团公司 Coking and scaling inhibitor and its preparation and application

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111004116A (en) * 2019-12-19 2020-04-14 湖北美和科技有限公司 Methacrylate monomer for preparing coking inhibitor component
CN112961715A (en) * 2021-03-02 2021-06-15 四川大学 Preparation method and application of novel hydrocarbon fuel coking inhibitor
CN112961715B (en) * 2021-03-02 2022-08-05 四川大学 Preparation method and application of novel hydrocarbon fuel coking inhibitor

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Application publication date: 20180306