CN106316756A - Aryl olefin monomer rectification polymerization inhibitor and preparation method thereof - Google Patents
Aryl olefin monomer rectification polymerization inhibitor and preparation method thereof Download PDFInfo
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- CN106316756A CN106316756A CN201510337570.4A CN201510337570A CN106316756A CN 106316756 A CN106316756 A CN 106316756A CN 201510337570 A CN201510337570 A CN 201510337570A CN 106316756 A CN106316756 A CN 106316756A
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Abstract
The invention relates to a rectification polymerization inhibitor, and especially relates to an aryl olefin monomer rectification polymerization inhibitor. The rectification polymerization inhibitor comprises a component A and a component B, the component A is a nitroxide radical compound, and the component B is a polyol ether compound. A mass ratio of the component A to the component B is (0.2-3.0):1. The compounded polymerization inhibitor has new polymer dispersing and dissolving functions, fully shows the substantial polymerization inhibition effect, avoids use of a retarder and other highly toxic substances, improves the quality of products, reduces the output of tar, effectively prolongs the running period of an aryl olefin monomer device, eliminates hidden safety troubles, and has good economic and social benefits. The invention also provides a preparation method of the aryl olefin monomer rectification polymerization inhibitor. The method is simple, and is easy to enforce.
Description
Technical field
The present invention relates to a kind of rectifying polymerization inhibitor, particularly relate to rectifying polymerization inhibitor of a kind of aromatic olefin monomers and preparation method thereof.
Background technology
Aromatic olefin monomers chemical property is active, and such as styrene is a kind of important polymerization monomer, it can with self-polymerization or and its
He is polymerized by monomer, is widely used in synthesis macromolecular material, coating, medicine and other fields.Styrene the most just can be sent out
Raw thermal excitation polyreaction slowly.Styrene is a kind of broad-spectrum polymerization monomer, and it can be with self-polymerization or single with other
Body polymerization becomes the raw material for manufacturing a large amount of domestic and industrial product.Styrene chemical property is active, is easily polymerized, in environment temperature
Degree is lower just can occur thermal excitation polyreaction slowly, and temperature is the highest, and polymerization speed is the fastest.In order to reduce phenyl ethylene rectification mistake
Polymerization losses in journey, it is ensured that distillation system is normally carried out, it is necessary to add polymerization inhibitor in distillation process.
Since styrene monomer industrialized production, people constantly carry out the exploitation of polymerization inhibitors for styrene rectification, to reduce inhibition
The toxicity of agent, improves inhibition efficiency, reduces the loss in the styrene course of processing；Some low toxicities of period efficient polymerization inhibitor kind
Start to use on Styrene Process.These polymerization inhibitors mainly have two big kinds: true polymerization inhibitor and retarder, true polymerization inhibitor
As NO free radical compounds can produce longer induction period, each free radical can be made in induction period all to terminate, make polymerization complete
Full cut-off only, does not therefore have polymer to produce substantially in induction period.Once induction period terminates, and starts to produce number of polymers, therefore
Use true polymerization inhibitor, there is potential safety hazard that is easily short by free radical consumption, service life and that cause monomer implode.Retarder
As more stable in nitro-phenolic compound chemical property, inhibition process lost efficacy few, but only made a part of radical termination, made polymerization anti-
Should slow down, the most not produce obvious induction period, so causing the content of polymer the most slowly to increase.
In order to overcome the shortcoming of above two polymerization inhibitor, Chinese scholars uses compounding to true polymerization inhibitor and retarder, both can prolong
Long induction period in polymerization, it is also possible to make the rate of polymerization after induction period reduce, thus play the effect reducing polymer, play collaborative
Effect.Such as, CN1392127A discloses a kind of styrene polymerization inhibitor and purposes, and this polymerization inhibitor selects NO free radical and phenol
Compounds is compounding component, forms according to a certain ratio, and preferable consumption is 400～800mg/kg, under the conditions of heating 2h,
Polymer content 0.17%, the compound polymerization inhibitor of formation is significantly improved compared with the polymerization inhibition effect of the one-component of same concentration, toxicity
Lower than phenolic compound, use temperature higher, it is adaptable to cinnamic distillation process.
CN102249842A describes a kind of cinnamic efficient and environment-friendly type polymerization inhibitor, is also compound polymerization inhibitor, by nitrogen oxygen freely
Base class compound, hydroxylamine compound, nitro-phenolic compound and phosphite ester compound are constituted, and this compound system make use of
Synergism between component, overcomes retarder and the respective shortcoming of true polymerization inhibitor, increases molten in styrene of polymerization inhibitor
Xie Du.
CN102070394A discloses a kind of antisludging agent for styrene rectification system, by process for preparation of di-tert-butyl phenol antioxidant, nitrophenols
Five kinds of components of benzene kind solvent such as class polymerization inhibitor, hydroxyl amine polymerization inhibitor, succimide class dispersant and ethylbenzene are compounding to be formed, institute
Solve the technical problem that be suppression phenyl ethylene rectification during produce dirty thing, and by stick to equipment surface dirty thing disperse under
Come, thus extend the cycle of operation of styrene device.Wherein polymerization inhibitor component is also with between true polymerization inhibitor and retarder
Synergism, to improve polymerization inhibition effect.
CN103360201A relates to a kind of method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, mixes including by hydro carbons
Thing in the presence of polymerization inhibitor with double solvents carry out extracting rectifying reclaim styrene therein, described double solvents include 80～
The cosolvent of main solvent, 0.01～19% of 99% and 0.1～the water of 2.0%, extraction main solvent is selected from sulfone compound, hydrotropy
Agent is the mixture of methoxyphenol or methoxyphenol and glycol monomethyl ether, and polymerization inhibitor is by NO free radical, nitrophenols, azanol
Compound is compounding to be formed.This invention selects compound extracting solvent to coordinate with high-efficiency polymerization inhibitor, can significantly reduce cinnamic aggregate rate.
Summary of the invention
For the deficiencies in the prior art, it is an object of the invention to provide the rectifying polymerization inhibitor of a kind of aromatic olefin monomers, toxicity is little,
Under high temperature, polymerization inhibition effect is good, has dispersion hydrotropy effect while anti-polymerization, and the present invention also provides for its preparation method.
The rectifying polymerization inhibitor of aromatic olefin monomers of the present invention, including component A and B component, component A is NO free radical class
Compound, B component is polyol ethers compounds.
The present invention is except two kinds of components of A, B, it is also possible to containing a small amount of or other components of trace.Other components can be that alcohols is molten
One or more in agent, benzene class or hydro carbons.Alcohols solvent is methanol, ethanol, butanol or ethylene glycol；Benzene class is toluene or second
Benzene；Hydro carbons is hexamethylene or normal hexane etc..The Functionality, quality and appealing design of other components elects the 0-30% of two kinds of component gross masses of A, B as.
The rectifying polymerization inhibitor of aromatic olefin monomers of the present invention, is preferably made up of component A and B component, component A be nitrogen oxygen from
By base class compound, B component is polyol ethers compounds.
Wherein:
Component A is 0.2～3.0:1 with the mass ratio of B component.
Component A is preferably 0.5～2.0:1 with the mass ratio of B component.
NO free radical compounds be 1-hydroxyl-TEMPO (hereinafter referred to as 1-TMHPO),
TEMPO (TMHPO), 4-hydroxyl-TEMPO
(4-TMHPO), three (4-hydroxyl-TEMPO) phosphorus (TMHPOP), 4-acetylaminohydroxyphenylarsonic acid 2,
One or many in 2,6,6-tetramethyl piperidine nitrogen oxygen free radicals (4-A-TMHPO) or di-tert-butyl nitroxide (DTBNO)
Kind.
Polyol ethers compounds be diethylene glycol monobutyl ether (be called for short EGMBE), dibutyl ethylene glycol ether (EGEBE), three
Glycol monoethyl ether (TEGMME), triethylene glycol butyl ether (TEGMBE), Dipropylene glycol mono-n-butyl Ether (DPGBE), dipropyl
One or more in glycol dimethyl ether (DPGDME) or butanediol diglycidyl ether (BDGE).
The rectifying polymerization inhibitor of aromatic olefin monomers of the present invention, including component A and B component, component A is NO free radical class
Compound, B component is polyol ethers compounds.NO free radical class polymerization inhibitor is a kind of true polymerization inhibitor, in induction period internal resistance
Poly-efficiency is high, can terminate living radical chain and increase.Auxiliary agent is polyol ethers compounds, and (nitrogen oxygen is freely with main polymerization inhibitor
Base class polymerization inhibitor) produce synergism, extend the induction period of true polymerization inhibitor；Meanwhile, this compound dissolution, dispersibility are strong,
Can the polymer of generation be dissolved in the middle of material, make polymer prevented from caking be flocked on equipment surface, prevent from blocking tower.
So, utilize the synergism of main polymerization inhibitor and auxiliary agent, on the one hand overcome the difficult problem that true polymerization inhibitor induction period is short, more greatly
Inhibit to degree the polymerization of aromatic olefin monomers；On the other hand, even if creating the polymer of trace, this polymerization inhibitor can also lead to
Cross dispersion dissolution, polymer uniform is distributed in the middle of material so that it is be difficult to gathering and stick to equipment or pipe surface, have
Effect extends the cycle of operation of virtue alkene rectifier unit, decreases the tar yield in distillation process, it is to avoid implode or blocking pipeline
Potential safety hazard occurs.
Polymerization inhibitor of the present invention, in the distillation process of aromatic olefin monomers, considers from polymerization inhibition effect and economic benefit,
Polymerization inhibitor consumption is the 0.001%～0.1% of aromatic olefin monomers quality, preferably 0.005%～0.08%, the vacuum of distillation process
Being 0.005～0.1Mpa, rectification temperature is 80～140 DEG C.
In liquid condition under polymerization inhibitor room temperature of the present invention, during commercial Application, polymerization inhibitor can feed together along with being newly added monomer,
Join in aromatic olefin monomers rectifying column, to ensure the polymerization inhibitor effective distribution in monomer.Owing to polymerization inhibitor is in monomer rectifying mistake
Journey gradually uses up, so suitably to supplement polymerization inhibitor in distillation process, to ensure device to have enough polymerization inhibitors send out
Waving inhibition, in production, inhibitor solution adds in a continuous manner, to ensure that polymerization inhibitor consumption reaches minimum use requirement.This
The polymerization inhibitor of invention is for the negative pressure high temperature distillation process of aromatic olefin monomers, and maximum operation (service) temperature is up to 140 DEG C.
The polymerization inhibitor of the present invention belongs to aerobic-type polymerization inhibitor, and the existence of a small amount of oxygen can strengthen its polymerization inhibition effect.
The compound polymerization inhibitor of the present invention can be used for the production process of aromatic olefin monomers, is particularly well-suited to negative pressure high temperature distillation process, especially
It is applicable to styrene high temperature distillation process.Also extend to the transport of aromatic olefin monomers, store and use the application of process, with
Improve the purity of monomer, reduction cost, eliminate safe hidden trouble.
The preparation method of the rectifying polymerization inhibitor of aromatic olefin monomers of the present invention, mixes component A and B component, at room temperature
Stir, obtain product.
The invention have the advantages that
(1) polymerization inhibitor for aromatic olefin monomers distillation process of the present invention, utilizes the synergism between component dexterously,
Overcome prior art can only, polymerization inhibitor compounding by several true polymerization inhibitors and retarder in use first dissolve with solvent
Defect.
(2) compound polymerization inhibitor of the present invention makes polymerization inhibitor have the new function of dispersing and dissolving polymer.
(3) compound polymerization inhibitor of the present invention, has given full play to true polymerization inhibitor polymerization inhibition effect significant advantage, it is to avoid use retarder
Deng highly toxic substance, improve product quality, reduce tar yield.
(4) compound polymerization inhibitor of the present invention, is liquid solution at normal temperatures, improves its dissolubility in aromatic olefin monomers,
Rectifier unit can be directly added into use, the industrial operation eliminating heating for dissolving, operate with more convenient.
(5) function of the dispersing and dissolving polymer of compound polymerization inhibitor, effectively extends the cycle of operation of aromatic olefin monomers device, disappears
Except potential safety hazard, there are preferable economic benefit and social benefit.
(6) polymerization inhibitor that the present invention provides, has dispersion hydrotropy effect while anti-polymerization, and toxicity is little, at high temperature inhibit
Effective and can in time the polymer of generation be disperseed, to improve virtue alkene rectification yield, reduce and pollute, eliminate safety the most hidden
Suffer from.
Detailed description of the invention
Below in conjunction with embodiment, the present invention will be further described.
Below in conjunction with embodiment, the invention will be further described, but it is not limiting as the enforcement of the present invention.
In embodiment, material used is in addition to specified otherwise, is commercial.
The part mentioned in embodiment is mass fraction.
Embodiment 1～12
Weigh two kinds of components of A, B of the present invention by certain consumption, be stirred at room temperature uniformly, obtain polymerization inhibitor, with benzene second
Alkene joins in four-hole boiling flask together, adds a condenser above four-hole boiling flask, with the air 5～10 in nitrogen exchange system
Minute, to reduce the oxygen content in flask, then system sealing, four-hole boiling flask is placed in thermostatic heater heating, at 125 DEG C
Under the conditions of constant temperature certain time, polystyrene content in sample analysis styrene.
Growing amount with gravimetric detemination polymer: utilize polymer not dissolve in the characteristic of methanol, adds enough doing in the sample
Dry methanol, makes polymer precipitate completely, then filters, is dried, weighs, constant weight, can obtain generating the quality of polymer.
Experimental result is as shown in table 1, and in table, polymerization inhibitor system each constituent mass number is using cinnamic quality as 100 parts of benchmarks.
Table 1 different component polymerization inhibitor polymerization inhibition effect
Note: 4-TMHPO is 4-hydroxyl-TEMPO, and 1-TMHPO is 1-hydroxyl-2,2,
6,6-tetramethyl piperidine nitrogen oxygen free radicals, TMHPO is TEMPO, and TMHPOP is
Three (4-hydroxyl-TEMPO) phosphorus, DTBNO is di-tert-butyl nitroxide,
4-A-TMHPO is 4-acetylaminohydroxyphenylarsonic acid-TEMPO.
In B component, EGMBE is the abbreviation of diethylene glycol monobutyl ether, and EGEBE is dibutyl ethylene glycol ether, TEGMME
For triethylene glycol monomethyl ether, TEGMBE is triethylene glycol butyl ether, and DPGBE is Dipropylene glycol mono-n-butyl Ether, and DPGDME is
Dimethyl ether, BDGE is butanediol diglycidyl ether.
As shown in Table 1, under the hot conditions of 125 DEG C, the polymerization inhibitor that two kinds of components of A, B are compounding present preferably inhibition
Effect, polymer content is relatively low.
Embodiment 13～19
Prepare polymerization inhibitor according to the process described in embodiment 1～12, and join in styrene, permanent under the conditions of 125 DEG C
Temperature 3 hours, polystyrene content in sample analysis styrene, wherein component A be TMHPOP, B component be EGMBE.
Using cinnamic quality as 100 parts of benchmarks, component A: B component is 1:1, under different polymerization inhibitor consumptions, polymerization inhibition effect is such as
Shown in table 2.
Under table 2 different amounts, polymerization inhibition effect compares
Visible, along with the increase of polymerization inhibitor consumption, polymerization inhibition effect significantly improves.In actual application, can be from polymerization inhibitor consumption and warp
Ji benefit considers.
Embodiment 20
Experimental procedure and method are analyzed in styrene poly-with embodiment 13～19, reacting by heating under the conditions of 125 DEG C, timing sampling
Styrene-content.Using cinnamic quality as 100 parts of benchmarks, wherein component A is TMHPOP, consumption 0.02 part；
B component is EGMBE, consumption 0.02 part.As shown in table 3 in the experimental result of different time.
Table 3 compound polymerization inhibitor polymerization inhibition effect is over time
| Response time, h | Polymer content % |
| 1 | 0.0 |
| 2 | 0.0 |
| 3 | 0.16 |
| 4 | 0.35 |
| 5 | 0.65 |
| 6 | 0.90 |
| 8 | 1.82 |
Embodiment 21
Compound polymerization inhibitor, with embodiment 20, is joined in methyl styrene by experimental procedure and method, heats under the conditions of 125 DEG C
Reaction, polymethylstyrene content in methyl styrene analyzed by timing sampling.Using the quality of methyl styrene as 100 parts of benchmark
Calculating, wherein component A is TMHPO, consumption 0.03 part；B component is EGMBE, consumption 0.02 part.At different time
Experimental result as shown in table 4.
The polymerization inhibition effect of table 4 compound polymerization inhibitor p-methylstyrene
Embodiment 22
Compound polymerization inhibitor is used in certain factory's phenyl ethylene rectification tower, using cinnamic quality as 100 parts of benchmarks, wherein A
Component is TMHPOP, consumption 0.015 part；B component is EGMBE, consumption 0.015 part, i.e. the total consumption of polymerization inhibitor 0.03%.
Phenyl ethylene rectification tower operates under condition of negative pressure, and overhead is mainly containing ethylbenzene, toluene, benzene and lighter component, tower bottoms
For crude styrene.Its operation service condition is: tower top operation Stress control, 14～21kpa, operates temperature about 75 DEG C, at the bottom of tower
Operation temperature about 97 DEG C, in tower, the compound polymerization inhibitor concentration general control in charging is 0.015%, inhibitor concentration one in tower bottoms
As 0.03%.
The compound polymerization inhibitor not consumed enters refining benzene ethylene column with tower bottoms.This tower is also a rectification for operation under condition of negative pressure
Tower, adds after overhead is condensed and obtains styrene product, and tower bottoms is tar liquid, main containing styrene and tar.Work
In industry, the height of tar yield is to weigh polymerization inhibition effect and affect the key factor of styrene product yield.Remainder is along with tar
Enter in tar storage tank.
Comparative example 1
Rectification process is identical with embodiment 22, and polymerization inhibitor uses this factory former polymerization inhibitor formula, for nitropheneol DNBP and true resistance
Poly-agent 628D, consumption is: in tower, the compound polymerization inhibitor concentration in charging is generally 0.025%, inhibitor concentration one in tower bottoms
As 0.10%.Comparing result is as shown in table 5.
The table 5 tar yield contrast in producing
Visible, after the formula of the present invention, tar yield is decreased obviously, and improves the styrene monomer yield in distillation process.
Embodiment 23
By certain consumption weighed styrene andRustless steel θ ring filler join in two four-hole boiling flasks together, with benzene second
The quality of alkene is as 100 parts of benchmarks, and adding component A in one of them four-hole boiling flask is TMHPOP, consumption 0.015 part；
B component is EGEBE, consumption 0.015 part；A condenser is added, with the air in nitrogen exchange system above four-hole boiling flask
5～10 minutes, to reduce the oxygen content in flask, then system sealing, four-hole boiling flask is placed in thermostatic heater heating,
Constant temperature 24 hours under the conditions of 125 DEG C, period has polymer to deposit in filler.Then lower the temperature, take out filler, dry, claim
Weight.
Comparative example 2
Technique used is identical with embodiment 23, and difference is in four-hole boiling flask to add DNBP0.015 part and 628D0.015 part.
Testing embodiment 23 and comparative example 2, result shows, uses polymerization inhibitor, filler to have no obvious by embodiment 23
Weightening finish；The filler taken out in comparative example 2, shows there is polymer deposition, weightening finish 1%.Visible, B component of the present invention is to polymerization
Thing has obvious hydrotropy peptizaiton, and polymer can be made preferably to be dispersed in monomer solution.
Claims (8)
1. the rectifying polymerization inhibitor of an aromatic olefin monomers, it is characterised in that: including component A and B component, component A is nitrogen oxygen
Radical type compound, B component is polyol ethers compounds.
The rectifying polymerization inhibitor of aromatic olefin monomers the most according to claim 1, it is characterised in that: component A and the matter of B component
Amount ratio is 0.2～3.0:1.
The rectifying polymerization inhibitor of aromatic olefin monomers the most according to claim 1, it is characterised in that: component A and the matter of B component
Amount ratio is 0.5～2.0:1.
4. according to the rectifying polymerization inhibitor of the aromatic olefin monomers described in claim 1,2 or 3, it is characterised in that: NO free radical
Compounds be 1-hydroxyl-TEMPO, TEMPO,
4-hydroxyl-TEMPO, three (4-hydroxyl-TEMPOs)
One or more in phosphorus, 4-acetylaminohydroxyphenylarsonic acid-TEMPO or di-tert-butyl nitroxide.
5. according to the rectifying polymerization inhibitor of the aromatic olefin monomers described in claim 1,2 or 3, it is characterised in that: polyhydric alcohol ethers
Compound is diethylene glycol monobutyl ether, dibutyl ethylene glycol ether, triethylene glycol monomethyl ether, triethylene glycol butyl ether, dipropylene glycol
One or more in monobutyl ether, dimethyl ether or butanediol diglycidyl ether.
The rectifying polymerization inhibitor of aromatic olefin monomers the most according to claim 1, it is characterised in that: this polymerization inhibitor is for virtue alkene
In the distillation process of monomer, polymerization inhibitor consumption is the 0.001%～0.1% of aromatic olefin monomers quality.
The rectifying polymerization inhibitor of aromatic olefin monomers the most according to claim 1, it is characterised in that: this polymerization inhibitor is for virtue alkene
In the distillation process of monomer, the vacuum of distillation process is 0.005～0.1Mpa, and rectification temperature is 80～140 DEG C.
8. a preparation method for the rectifying polymerization inhibitor of the aromatic olefin monomers described in claim 1,2,3,6 or 7, its feature
It is: component A and B component are mixed, is stirred at room temperature uniformly, obtains product.
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| CN110330404A (en) * | 2019-07-02 | 2019-10-15 | 宜兴市中大凯水处理有限公司 | A kind of polymerization inhibitors for styrene rectification and preparation method thereof |
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| CN108341736A (en) * | 2017-01-23 | 2018-07-31 | 中国石油化工股份有限公司 | A kind of compound polymerization inhibitor and its application |
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