CN105503502B - The polymerization inhibitor for preventing alkynes from polymerizeing - Google Patents
The polymerization inhibitor for preventing alkynes from polymerizeing Download PDFInfo
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Abstract
The present invention relates to a kind of polymerization inhibitor for preventing alkynes from polymerizeing, 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 polymerization inhibitor including following components：The B component of 50%~60% component A 20%~30% by percentage to the quality, 10%~20% component C；Wherein, component A is hydroxylamine compound or/and morpholine kind compound, B component is pyridine or/and nitropyridine, and 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 polymerization inhibitor, specifically, being related to a kind of suitable for preventing natural gas partial
Aoxidize the polymerization inhibitor of 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.
Document CN102766008A discloses a kind of polymerization inhibitor of carbon three.The polymerization inhibitor is by following components in percentage by weight group
Into：15-40% 2,6- DI-tert-butylphenol compounds, 10-20% diethyl hydroxylamine, 5-15% isobutanol, 5-15% only son
The propanediol polyoxypropylene polyoxyethylene blocks polyethers of imidodicarbonic diamide and 1-5%.The polymerization inhibitor is used to suppress olefinic polymerization.
Document CN101107274A discloses a kind of polymerization inhibitor of 1,3-butadiene, and the polymerization inhibitor contains one or two
The anti-fouling agent based on alkyl phenol of hydroxyl, anti-fouling agent and organic solvent based on amine.The polymerization inhibitor is used to prevent 1,3- fourths
Diene polymerization.
The present invention provides a kind of polymerization inhibitor for being used to prevent that gas by partial oxidation of natural legal system acetylene technique alkynes from polymerizeing, and has pin
Solves above mentioned problem to property.
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 polymerization inhibitor.The 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 polymerization inhibitors described in using one of technical problem solved, are used for
The method of gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, using technical scheme, can prevent equipment and
Deposition fouling inside 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：One kind is used to prevent alkynes from gathering
The polymerization inhibitor of conjunction.The polymerization inhibitor is made up of component A, B component, component C.Wherein, component A is hydroxylamine compound or/and morpholine
Class compound, B component are pyridine or/and nitropyridine, and component C is acylhydrazone.The component A, B component, component C
Mass ratio is：(50~60):(20~30):(10~20), preferred mass ratio are (50~55):(25~30):(15~
20)。
In above-mentioned technical proposal, in component A, hydroxylamine compound represents at least one in compound selected from following formulas
Kind：Wherein, R1 and R2 is selected from one kind in H, methyl and ethyl, preferably methyl hydroxylamine；Morpholine kind compound
Refer to following formulas and represent at least one of compound：Wherein R is selected from:One in the alkyl of H or 1-4 carbon
Kind.
In above-mentioned technical proposal, in component A, hydroxylamine compound is selected from methyl hydroxylamine, and morpholine kind compound is selected from methyl
Morpholine.In above-mentioned technical proposal, the preferred nitropyridine of B component.
In above-mentioned technical proposal, the preferred benzaldehyde benzoyl hydrazone of component C.
In above-mentioned technical proposal, most preferred technical scheme is：Component A is the mixture of methyl hydroxylamine and methyl morpholine,
Both mass ratioes are 1：1, B component is nitropyridine, and component C is benzaldehyde benzoyl hydrazone, wherein, component A, B component and C groups
Point mass ratio be：(50~53):(26~30):(18~20).For solve above-mentioned technical problem two, it is of the present invention
Technical scheme is as follows：Using polymerization inhibitor described above, the method for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition.
Under the conditions of 0.08MPa~0.12MPa, the polymerization inhibitor was added directly at 100 degrees Celsius~120 degrees Celsius for this method
Oxide and Fe2+It is continuously replenished, absorption has in the 1-METHYLPYRROLIDONE solution of alkynes mixed gas, or after being first dissolved in solvent
It is then added in 1-METHYLPYRROLIDONE solution.
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 mass ratio of component A, the gross mass of B component and component C and solvent is in the polymerization inhibitor
1:(3~10), preferably 1:(3~5).
In above-mentioned technical proposal, in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding polymerization inhibitor and solvent, inhibition
The mass concentration scope of agent is 50~2000 μ g/g, preferably 200-800 μ g/g.
In above-mentioned technical proposal, alkynes mixed gas main component is acetylene, in addition to propine, butine, diacetylene, ethene
One or more in ethyl-acetylene and allene.
In above-mentioned technical proposal, with alkynes mixed gas total volume meter, the percentage by volume of acetylene is 92%~96%, fourth
The percentage by volume of diine is 1.8%~2.5%, and the percentage by volume of vinylacetylene is 0.5%~0.9%, allene
Percentage by volume is 0.5%~0.8%.
During inhibition, it is that each component can preferably disperse from the purpose of solvent.
The initiation system of gas by partial oxidation of natural legal system acetylene technique higher alkyne radical polymerization is present in system
The redox initiation system that peroxide and ferrous ion are formed.The advantage of the invention is that the B component and component C that add
The priming factorses of higher alkyne polymerization are limited from both ends respectively, so that less compound polymerization inhibitor is with regard to that can play preferable resistance
Poly- effect.
It is a kind of including following components by percentage to the quality using technical scheme：50%~60% A groups
Point, 20%~30% B component, the polymerization inhibitor for preventing alkynes polymerization of 10%~20% component C, wherein, component A is azanol
Class compound or/and morpholine kind compound, B component are pyridine or/and nitropyridine, and component C is acylhydrazone, is achieved
The technique effect of total polymer mass fraction 0.99% 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 | Diacetylene | Vinylacetylene | Allene |
| Percentage by volume/% | 95.23 | 1.07 | 0.01 | 2.38 | 0.71 | 0.60 |
【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；Added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is methyl hydroxylamine in polymerization inhibitor, and B component is
Pyridine, component C are benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：50:30:20, solvent is isopropyl
The mass ratio of alcohol, polymerization inhibitor and solvent is 1:5, to add the 1-METHYLPYRROLIDONE solution gross mass after polymerization inhibitor and solvent
Meter, 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, is made
It fully absorbs dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, HP7890 is used
Chromatographic total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymerization
The mass fraction of thing is 2.91%.
【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；Added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is methyl hydroxylamine in polymerization inhibitor, and B component is
Pyridine, component C are benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：55:30:15, solvent is isopropyl
The mass ratio of alcohol, polymerization inhibitor and solvent is 1:5, to add the 1-METHYLPYRROLIDONE solution gross mass after polymerization inhibitor and solvent
Meter, 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, is made
It fully absorbs dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, HP7890 is used
Chromatographic total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymerization
The mass fraction of thing is 3.04%.
【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 polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is methyl hydroxylamine in polymerization inhibitor, and B component is
Pyridine, component C are benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：55:25:20, solvent is isopropyl
The mass ratio of alcohol, polymerization inhibitor and solvent is 1:5, to add the 1-METHYLPYRROLIDONE solution gross mass after polymerization inhibitor and solvent
Meter, 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, is made
It fully absorbs dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, HP7890 is used
Chromatographic total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymerization
The mass fraction of thing is 2.97%.
【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 polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, component A is morpholine in polymerization inhibitor, and B component is pyrrole
Pyridine, component C are benzaldehyde benzoyl hydrazone, and the mass ratio of component A, B component and component C is：50:30:20, solvent is isopropanol,
The mass ratio of polymerization inhibitor and solvent is 1:5, 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 5.32%.
【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；Polymerization inhibitor is dissolved in after solvent and added in 1-METHYLPYRROLIDONE liquid, component A is azanol and methyl morpholine in polymerization inhibitor,
Both divide equally according to mass ratio, and B component is pyridine, and component C is benzaldehyde benzoyl hydrazone, the quality of component A, B component and component C
Than for：50:30:20, solvent is isopropanol, and the mass ratio of polymerization inhibitor and solvent is 1:5, to add after polymerization inhibitor and solvent
1-METHYLPYRROLIDONE solution gross mass meter, the addition of polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, with drum
Bubble mode is passed through alkynes mixed gas, it is fully absorbed dissolving；To the N- methyl dissolved with alkynes mixed gas after 50 hours
Pyrrolidone solution samples, with HP7890 chromatographic total polymer growing amounts.With in sampling sample in addition to the solvents
The gross mass meter of material be present, the mass fraction of total polymer is 2.33%.
【Embodiment 6~28】
It is constant with reference to the raw material composition of embodiment 1~5, mode of operation and operating condition, change following condition：Polymerization inhibitor
Composition, proportioning and addition, the mass ratio and solvent species of polymerization inhibitor and solvent, using with the identical method of embodiment 1~5
Analyze the total polymer growing amount of each embodiment.
In embodiment 1~28, polymerization inhibitor composition, proportioning and addition, selected type of solvent, resistance used in each embodiment
The mass ratio and total polymer growing amount of poly- agent and solvent are shown in Table 2.
In table 2, when component A and B component in polymerization inhibitor are related to 2 kinds of materials, both mass ratioes are 1:1；" proportioning " refers to A groups
Point, the mass ratio of B component and component C；" Bbh " represents benzaldehyde benzoyl hydrazone；" resistance:Agent " represent used in polymerization inhibitor and used molten
The mass ratio of agent；" addition " refers to the inhibition in terms of the 1-METHYLPYRROLIDONE solution gross mass after adding polymerization inhibitor and solvent
Agent addition；" polymer " refer to by material gross mass in addition to the solvents be present in sampling sample in terms of total polymer mass fraction.
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；Added after polymerization inhibitor is dissolved in into solvent in 1-METHYLPYRROLIDONE liquid, polymerization inhibitor is mass ratio 1:1 methyl hydroxylamine and first
Base morpholine, solvent are isopropanol, and the mass ratio of polymerization inhibitor and solvent is 1:5, to add the N- methyl after polymerization inhibitor and solvent
Pyrrolidone solution gross mass meter, the addition of polymerization inhibitor is 500 μ g/g；Under the conditions of 115 DEG C, 0.1MPa, in a manner of bubbling
Alkynes mixed gas is passed through, it is fully absorbed dissolving；To the N- crassitudes dissolved with alkynes mixed gas after 50 hours
Ketone solution sampling, with HP7890 chromatographic total polymer growing amounts.With existence in addition to the solvents in sampling sample
The gross mass meter of matter, the mass fraction of total polymer is 7.98%.
【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 1:5, 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 8.67%.
【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 2- methylphenols, and solvent is isopropyl
The mass ratio of alcohol, polymerization inhibitor and solvent is 1:5, to add the 1-METHYLPYRROLIDONE solution gross mass after polymerization inhibitor and solvent
Meter, 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, is made
It fully absorbs dissolving；To the 1-METHYLPYRROLIDONE solution sampling dissolved with alkynes mixed gas after 50 hours, HP7890 is used
Chromatographic total polymer growing amount.By the gross mass of material in sampling sample in addition to the solvents be present in terms of, total polymerization
The mass fraction of thing is 20.44%.
Claims (10)
1. a kind of polymerization inhibitor for preventing alkynes from polymerizeing, it is characterised in that the polymerization inhibitor is including by percentage to the quality with the following group
Point：50%~60% component A, 20%~30% B component, 10%~20% component C；Wherein, component A is azanol class
Compound or/and morpholine kind compound, B component are pyridine or/and nitropyridine, and component C is acylhydrazone.
2. the polymerization inhibitor according to claim 1 for preventing alkynes from polymerizeing, it is characterised in that in the component A, azanol class
Compound is selected from following formulas and represents at least one of compound：Wherein, R1 and R2 is selected from H, methyl and second
One kind in base；Morpholine kind compound refers to following formulas and represents at least one of compound：Wherein R is selected from
H or carbon number are one kind in 1-4 alkyl.
3. the polymerization inhibitor according to claim 1 for preventing alkynes from polymerizeing, it is characterised in that in the component A, azanol class
Compound is selected from methyl hydroxylamine, and morpholine kind compound is selected from methyl morpholine.
4. the polymerization inhibitor according to claim 1 for preventing alkynes from polymerizeing, it is characterised in that the B component is selected from nitro pyrrole
Pyridine.
5. the polymerization inhibitor according to claim 1 for preventing alkynes from polymerizeing, it is characterised in that the component C is selected from benzaldehyde
Benzoyl hydrazone.
6. the polymerization inhibitor according to claim 1 for preventing alkynes from polymerizeing, it is characterised in that the component A, B component and C groups
Point mass ratio be：(50~55):(25~30):(15~20).
A kind of 7. method for gas by partial oxidation of natural legal system acetylene technique alkynes inhibition, using described in claim 1-6
The polymerization inhibitor for preventing alkynes from polymerizeing, it is characterized in that, 100 degrees Celsius~120 degrees Celsius, under the conditions of 0.08MPa~0.12MPa, institute
State polymerization inhibitor and be added directly into peroxide and Fe2+Be continuously replenished and absorption has the 1-METHYLPYRROLIDONE of alkynes mixed gas
In solution, or it is then added to after being first dissolved in solvent in 1-METHYLPYRROLIDONE solution.
8. the method according to claim 7 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；A in the polymerization inhibitor
The mass ratio of component, the gross mass of B component and component C and solvent is 1:(3~10).
9. the method according to claim 7 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 polymerization inhibitor and the solvent, the matter of the polymerization inhibitor
Amount concentration is 50~2000 μ g/g.
10. the method according to claim 7 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, diacetylene, vinylacetylene and allene
In one or more；With alkynes mixed gas total volume meter, the percentage by volume of acetylene is 92%~96%, the body of diacetylene
Product percentage is 1.8%~2.5%, and the percentage by volume of vinylacetylene is 0.5%~0.9%, the volume basis of allene
Number is 0.5%~0.8%.
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| CN107185562B (en) * | 2017-05-27 | 2019-10-29 | 北京华福工程有限公司 | A kind of catalyst and its preparation method and application for acetylene dimer reaction |
| CN109651040A (en) * | 2017-10-12 | 2019-04-19 | 中国石油化工股份有限公司 | Higher alkyne compound polymerization inhibitor |
| 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 |
| CN109652077B (en) * | 2017-10-12 | 2022-07-12 | 中国石油化工股份有限公司 | Method for preventing polymerization of advanced alkyne in acetylene concentration system |
| 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 |
| 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 |
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