CN105566035B - Compound polymerization inhibitor - Google Patents
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- CN105566035B CN105566035B CN201410541506.3A CN201410541506A CN105566035B CN 105566035 B CN105566035 B CN 105566035B CN 201410541506 A CN201410541506 A CN 201410541506A CN 105566035 B CN105566035 B CN 105566035B
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Abstract
The present invention relates to a kind of compound polymerization inhibitor, mainly to solve in gas by partial oxidation of natural legal system acetylene technique alkynes, easily polymerization so as to block system and pipeline, influences the technical problem of device normal operation.The present invention is by using a kind of compound polymerization inhibitor including following components：60%~70% component A by percentage to the quality, 10%~20% B component, 10%~20% component C；Wherein, component A is the one or more in alcohol amine compound, hydroxylamine compound, morpholine kind compound, B component is hexa, component C preferably solves above-mentioned technical problem for the technical scheme of acylhydrazone, available in gas by partial oxidation of natural legal system acetylene technique alkynes inhibition field.
Description
Technical field
The invention belongs to chemical field, is related to a kind of compound polymerization inhibitor, specifically, being related to a kind of suitable for suppressing natural gas
The compound polymerization inhibitor of partial oxidation legal system acetylene technique alkynes polymerization.
Background technology
Gas by partial oxidation of natural legal system acetylene technique goes back by-product propine, butine, diacetylene, vinyl second in addition to acetylene is produced
Alkynes and allene.These alkynes properties are active, influence and act in many factors such as high temperature, micro amount of oxygen, peroxide, iron ions
Under, radical polymerization easily occurs and generates polymer.These polymer deposit fouling, occluding device inside equipment and pipeline
Or pipeline, heat transfer efficiency is influenceed, causes potential safety hazard, reduces the equipment cycle of operation and production efficiency.
Prior art relates generally to the polymerization of ethene suppressing based compound and suppresses the polymerization inhibitor of styrene polymerization.
Document CN1362943A discloses a kind of polymerization inhibitor for being used to prevent polymerization of vinyl compound.The polymerization inhibitor includes
Phenthazine and strong acid.
Document CN101955411A discloses a kind of compound polymerization inhibitor for suppressing styrene polymerization.The compound polymerization inhibitor includes
P-tert-Butylcatechol, o-tert-butyl 4,6- dinitrophenol and/or high-efficiency polymerization inhibitor PI-70.
The present invention provides a kind of compound polymerization inhibitor for being used to suppress the polymerization of gas by partial oxidation of natural legal system acetylene technique alkynes,
Targetedly solves above mentioned problem.
The content of the invention
One of technical problems to be solved by the invention are alkynes easily radical polymerization and the problem of generate polymer, are carried
For a kind of compound polymerization inhibitor.The compound polymerization inhibitor that this method provides has the advantages of polymerization inhibition effect is good.
The two of the technical problems to be solved by the invention are the compound polymerization inhibitors described in using one of technical problem solved,
For the method for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, using technical scheme, can prevent from setting
Deposition fouling inside standby and pipeline, reduces occluding device or pipeline, has the advantages of improving the equipment cycle of operation and production efficiency.
To solve one of above-mentioned technical problem, the technical solution adopted in the present invention is as follows：A kind of compound polymerization inhibitor.This is multiple
Formed with polymerization inhibitor by component A, B component, component C compounding.Wherein, component A be alcohol amine compound, hydroxylamine compound,
One or more in morpholine kind compound, B component are hexa, and component C is acylhydrazone.The component A,
B component, the mass ratio of component C are：(60~70):(10~20):(10~20).
In above-mentioned technical proposal, in component A, alcohol amine compound is selected from monoethanolamine, diethanol amine, dimethyl ethanol
At least one of amine, ehtylethanolamine, preferably diethanol amine, monoethanolamine, more preferably diethanol amine；Hydroxylamine compound is selected from
Following formulas represent at least one of compound：Wherein, R1 and R2 is selected from one kind in H, methyl and ethyl,
It is preferred that azanol, methyl hydroxylamine, more preferably methyl hydroxylamine；Morpholine kind compound represents at least one in compound selected from following formulas
Kind：Wherein R is one kind in 1-4 alkyl, preferably morpholine, methyl morpholine, more preferably methyl selected from H or carbon number
Quinoline.
In above-mentioned technical proposal, the preferred benzaldehyde benzoyl hydrazone of component C.
In above-mentioned technical proposal, preferred scheme is：Component A is diethanol amine, and B component is hexa, C groups
It is divided into benzaldehyde benzoyl hydrazone, wherein, component A, B component, the mass ratio of component C are：(63~67):(14~18):(15~
19).To solve the two of above-mentioned technical problem, the technical solution adopted in the present invention is as follows：Using compound polymerization inhibitor described above,
Method for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition.This method at 100 degrees Celsius~120 degrees Celsius,
Under the conditions of 0.08MPa~0.12MPa, the compound polymerization inhibitor is added directly into peroxide and Fe2+It is continuously replenished, absorbs
Have in the 1-METHYLPYRROLIDONE solution of alkynes mixed gas, or 1-METHYLPYRROLIDONE solution is then added to after being first dissolved in solvent
In.
In above-mentioned technical proposal, in the alcohol compound that the solvent is benzene,toluene,xylene, carbon number is 3-5 at least
One kind, preferably isopropanol.
In above-mentioned technical proposal, the quality of component A, the gross mass of B component and component C and solvent in the compound polymerization inhibitor
Than for 1:(3~8), preferably 1:(3~4).
In above-mentioned technical proposal, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding compound polymerization inhibitor and solvent,
The mass concentration scope of compound polymerization inhibitor is 100~1500 μ g/g, preferably 300-700 μ g/g.
In above-mentioned technical proposal, alkynes mixed gas main component is acetylene, in addition to propine, butine, vinylacetylene,
One or more in diacetylene and allene.
In above-mentioned technical proposal, with alkynes mixed gas total volume meter, the percentage by volume of acetylene is 93%~95%, second
The percentage by volume of vinyl acetylene is 2.0%~2.5%, and the percentage by volume of diacetylene is 0.8%~1.2%, allene
Percentage by volume is 0.6%~1.0%.
During inhibition, it is that each component can preferably disperse from the purpose of solvent.The compounding inhibition of the present invention
Agent its mainly to inhibit mechanism reacted by the living radical inhibited in agent molecule and system, generate non-free radical or can not be after
The continuous low activity free radical for triggering polymerization, so that polymerization.Gas by partial oxidation of natural legal system acetylene technique higher alkyne is certainly
The redox initiation system being made up of the initiation system peroxide present in system and ferrous ion of base polymerization.This
The polymerization inhibitor component that the advantages of invention is to add limits the priming factorses of higher alkyne polymerization, so that less compounding resistance
Poly- agent is with regard to that can play preferable polymerization inhibition effect.
It is a kind of including following components by percentage to the quality using technical scheme：60%~70% A groups
Point, 10%~20% B component, the compound polymerization inhibitor of 10%~20% component C, wherein, component A is ethanolamines chemical combination
One or more in thing, hydroxylamine compound, morpholine kind compound, B component are hexa, and component C is acylhydrazone class
Compound, achieve the technique effect of the total polymer mass fraction 1.09% in terms of it material gross mass in addition to the solvents be present.
Embodiment
With reference to embodiment, the method for further illustrating the present invention.Alkynes mixed gas used in embodiment and comparative example
Composition be shown in Table 1.
Table 1
| Gas forms | Acetylene | Propine | Butine | Vinylacetylene | Diacetylene | Allene |
| Percentage by volume/% | 94.32 | 0.81 | 0.71 | 2.23 | 1.17 | 0.76 |
【Embodiment 1】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Compound polymerization inhibitor is dissolved in after solvent and added in 1-METHYLPYRROLIDONE liquid, component A is monoethanolamine in compound polymerization inhibitor, B
Component is hexa, and component C is benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：63:18:
19, solvent is isopropanol, and the mass ratio of compound polymerization inhibitor and solvent is 1:3, to add the N- after compound polymerization inhibitor and solvent
Methylpyrrolidone solution gross mass meter, the addition of compound polymerization inhibitor is 500 μ g/g；Alkynes gaseous mixture is passed through in a manner of bubbling
Body, it is set to fully absorb dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, use
HP7890 chromatographic total polymer growing amounts.By the gross mass of material in sampling sample in addition to the solvents be present in terms of,
The mass fraction of total polymer is 2.32%.
【Embodiment 2】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Compound polymerization inhibitor is dissolved in after solvent and added in 1-METHYLPYRROLIDONE liquid, component A is monoethanolamine in compound polymerization inhibitor, B
Component is hexa, and component C is benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：60:20:
20, solvent is isopropanol, and the mass ratio of compound polymerization inhibitor and solvent is 1:3, to add the N- after compound polymerization inhibitor and solvent
Methylpyrrolidone solution gross mass meter, the addition of compound polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, with
Bubbling mode is passed through alkynes mixed gas, it is fully absorbed dissolving；To the N- first dissolved with alkynes mixed gas after 50 hours
Base pyrrolidone solution samples, with HP7890 chromatographic total polymer growing amounts.With remove solvent in sampling sample
The outer gross mass meter that material be present, the mass fraction of total polymer is 2.47%.
【Embodiment 3】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Added after compound polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is diethanol in compound polymerization inhibitor
Amine, B component are hexa, and component C is benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：63:
18:19, solvent is isopropanol, and the mass ratio of compound polymerization inhibitor and solvent is 1:3, to add after compound polymerization inhibitor and solvent
1-METHYLPYRROLIDONE solution gross mass meter, the addition of compound polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa,
Alkynes mixed gas is passed through in a manner of bubbling, it is fully absorbed dissolving；To the N- dissolved with alkynes mixed gas after 50 hours
Methylpyrrolidone solution samples, with HP7890 chromatographic total polymer growing amounts.With in sampling sample except molten
The gross mass meter of material outside agent be present, the mass fraction of total polymer is 1.43%.
【Embodiment 4】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Added after compound polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is diethanol in compound polymerization inhibitor
Amine, B component are hexa, and component C is benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：67:
14:19, solvent is isopropanol, and the mass ratio of compound polymerization inhibitor and solvent is 1:3, to add after compound polymerization inhibitor and solvent
1-METHYLPYRROLIDONE solution gross mass meter, the addition of compound polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa,
Alkynes mixed gas is passed through in a manner of bubbling, it is fully absorbed dissolving；To the N- dissolved with alkynes mixed gas after 50 hours
Methylpyrrolidone solution samples, with HP7890 chromatographic total polymer growing amounts.With in sampling sample except molten
The gross mass meter of material outside agent be present, the mass fraction of total polymer is 1.56%.
【Embodiment 5】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Added after compound polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is diethanol in compound polymerization inhibitor
Amine, B component are hexa, and component C is benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：67:
18:15, solvent is isopropanol, and the mass ratio of compound polymerization inhibitor and solvent is 1:3, to add after compound polymerization inhibitor and solvent
1-METHYLPYRROLIDONE solution gross mass meter, the addition of compound polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa,
Alkynes mixed gas is passed through in a manner of bubbling, it is fully absorbed dissolving；To the N- dissolved with alkynes mixed gas after 50 hours
Methylpyrrolidone solution samples, with HP7890 chromatographic total polymer growing amounts.With in sampling sample except molten
The gross mass meter of material outside agent be present, the mass fraction of total polymer is 1.51%.
【Embodiment 6~35】
It is constant with reference to the raw material composition of embodiment 1~5, mode of operation and operating condition, change following condition：Compounding inhibition
The mass ratio and solvent species of composition, proportioning and the addition of agent, compound polymerization inhibitor and solvent, using with the phase of embodiment 1~5
Same method analyzes the total polymer growing amount of each embodiment.
In embodiment 1~35, compound polymerization inhibitor composition, proportioning and addition, selected solvent used in each embodiment
The mass ratio and total polymer growing amount of type, compound polymerization inhibitor and solvent are shown in Table 2.
In table 2, when component A and B component in compound polymerization inhibitor are related to 2 kinds and two or more material, each material is according to quality
Respectively；" proportioning " refers to the mass ratio of component A, B component and component C；" H-am " represents hexa, and " Bbh " represents benzene first
Aldehyde benzoyl hydrazone；" resistance:The mass ratio of compound polymerization inhibitor and solvent for use used in agent " expression；" addition " refers to add compounding resistance
The compound polymerization inhibitor addition of 1-METHYLPYRROLIDONE solution gross mass meter after poly- agent and solvent；" polymer " refers to be taken
The total polymer mass fraction of material gross mass meter in all product in addition to the solvents be present.
Table 2
【Comparative example 1】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Being added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, polymerization inhibitor is diethanol amine, and solvent is isopropanol,
The mass ratio of polymerization inhibitor and solvent is 1:3, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding polymerization inhibitor and solvent,
The addition of polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, alkynes mixed gas is passed through in a manner of bubbling, makes it
Fully absorb dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, with HP7890 gas
Chromatograph total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymer
Mass fraction be 8.91%.
【Comparative example 2】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Being added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, polymerization inhibitor is methyl hydroxylamine, and solvent is isopropanol,
The mass ratio of polymerization inhibitor and solvent is 1:3, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding polymerization inhibitor and solvent,
The addition of polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, alkynes mixed gas is passed through in a manner of bubbling, makes it
Fully absorb dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, with HP7890 gas
Chromatograph total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymer
Mass fraction be 10.23%.
【Comparative example 3】
100 parts of pure 1-METHYLPYRROLIDONE liquid of analysis are added in the stainless steel cauldron for heating and stirring with chuck
Body；Added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, polymerization inhibitor is phenthazine, and solvent is isopropanol, resistance
The mass ratio of poly- agent and solvent is 1:3, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding polymerization inhibitor and solvent, resistance
The addition of poly- agent is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, alkynes mixed gas is passed through in a manner of bubbling, fills it
Divide and absorb dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, with HP7890 gas phases
Chromatograph analyzes total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymer
Mass fraction is 19.17%.
Claims (7)
1. a kind of compound polymerization inhibitor, it is characterised in that the compound polymerization inhibitor includes following components by percentage to the quality：60%
~70% component A, 10%~20% B component, 10%~20% component C；Wherein, component A be alcohol amine compound,
One or more in hydroxylamine compound, morpholine kind compound；
In the component A, alcohol amine compound is in monoethanolamine, diethanol amine, dimethylethanolamine, ehtylethanolamine
It is at least one；Hydroxylamine compound is selected from following formulas and represents at least one of compound：Wherein, R1 and R2 are equal
One kind in H, methyl and ethyl；Morpholine kind compound is selected from following formulas and represents at least one of compound：Wherein, R is one kind in 1-4 alkyl selected from H or carbon number；
B component is hexa, and component C is selected from benzaldehyde benzoyl hydrazone；
The mass ratio of the component A, B component and component C is：(63~67):(14~18):(15~19).
2. compound polymerization inhibitor according to claim 1, it is characterised in that in the component A, alcohol amine compound is selected from
Monoethanolamine, diethanol amine, hydroxylamine compound are selected from azanol, methyl hydroxylamine, and morpholine kind compound is selected from morpholine, methyl morpholine.
A kind of 3. method for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, using described in claim 1 or 2
Compound polymerization inhibitor, it is characterized in that, 100 degrees Celsius~120 degrees Celsius, under the conditions of 0.08MPa~0.12MPa, the compounding inhibition
Agent is added directly into peroxide and Fe2+Be continuously replenished and absorption has the 1-METHYLPYRROLIDONE solution of alkynes mixed gas
In, or be then added to after being first dissolved in solvent in 1-METHYLPYRROLIDONE solution.
4. the method according to claim 3 for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, its feature
It is, at least one of alcohol compound that the solvent is benzene,toluene,xylene, carbon number is 3-5.
5. the method according to claim 3 for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, its feature
It is, the mass ratio of component A, the gross mass of B component and component C and solvent is 1 in the compound polymerization inhibitor:(3~8).
6. the method according to claim 3 for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, its feature
It is, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding the compound polymerization inhibitor and the solvent, the compounding resistance
The mass concentration of poly- agent is 100~1500 μ g/g.
7. the method according to claim 3 for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, its feature
It is, the alkynes mixed gas main component is acetylene, in addition to propine, butine, vinylacetylene, diacetylene and allene
In one or more；With alkynes mixed gas total volume meter, the percentage by volume of acetylene is 93%~95%, vinylacetylene
Percentage by volume be 2.0%~2.5%, the percentage by volume of diacetylene is 0.8%~1.2%, the volume basis of allene
Number is 0.6%~1.0%.
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| CN107314245B (en) * | 2016-06-12 | 2019-03-01 | 中国石油化工股份有限公司 | Compositional type hydrate polymerization inhibitor composition containing lecithin and application thereof |
| 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 |
| CN109651059B (en) * | 2017-10-12 | 2024-03-26 | 中国石油化工股份有限公司 | Method for inhibiting polymerization of higher alkyne in acetylene concentration system |
| CN109651060A (en) * | 2017-10-12 | 2019-04-19 | 中国石油化工股份有限公司 | Higher alkyne combines polymerization inhibitor |
| CN109651061A (en) * | 2017-10-12 | 2019-04-19 | 中国石油化工股份有限公司 | Higher alkyne composite polymerzation inhibitor |
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| WO2007074750A1 (en) * | 2005-12-26 | 2007-07-05 | Toagosei Co., Ltd. | Process for producing (meth)acrylic ester |
| CN101284826B (en) * | 2007-04-11 | 2011-05-25 | 中国石油天然气股份有限公司 | Method for decoloring sulfolane |
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