CN107868156A - A kind of novel hydrates kinetic inhibitor - Google Patents
A kind of novel hydrates kinetic inhibitor Download PDFInfo
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- CN107868156A CN107868156A CN201610861462.1A CN201610861462A CN107868156A CN 107868156 A CN107868156 A CN 107868156A CN 201610861462 A CN201610861462 A CN 201610861462A CN 107868156 A CN107868156 A CN 107868156A
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F126/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
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Abstract
The invention discloses a kind of hydrate dynamic inhibitor of structural formula as shown in formula I, it is of the invention water-soluble fine, inhibitory activity is high, good inhibition can be obtained, and dosage is few, cost reduces, with low dosage, efficiently, the advantages that applicability is wide, can be under low dosage concentration (0.1~10wt%), used in high supercooling degree environment, hydrate nucleation time can effectively be delayed, reduce hydrate generating rate, suitable for oil gas water three phase or profit or air water two-phase coexistent system, applied to oil-gas mining, suppress the generation of hydrate in processing and course of conveying, do not restricted by degree of supercooling and application scenario, prospect with wide application.Wherein n=100~40000, R are * (CH2) m*, m=1~5.
Description
Technical field：
The present invention relates to chemical technology field, and in particular to a kind of novel hydrates kinetic inhibitor.
Background technology：
From Hammerschmidt in 1934 first in natural-gas transfer pipeline find gas hydrates since people
The understanding for gas hydrates and research are started.Gas hydrates be some light gas compositions in natural gas such as
One kind that hydrogen, carbon dioxide, nitrogen, methane, ethane, hydrogen sulfide etc. interact and formed with hydrone under certain condition
Non-stoichiometric clathrate complex.Later it has been found that some other light gas or liquid can also be with water one
Hydrate is formed under conditions of fixed, is referred to as gas hydrate or Study of Clathrate Hydrates.Study of Clathrate Hydrates structure can substantially be divided into three
Type, i.e. I type, II type and H types.
As oil-gas field development is towards deep-sea development, flowing safety guarantee problem more highlights caused by hydrate.It is deep
The complex environment of marine high pressure low temperature so that gas hydrates are easily formed, and cause failure, the pipe of oil-gas mining instrument and equipment
The blocking in road, great potential safety hazard, influence normal oil-gas mining and transport operation.Oil gas in some shallow seas and extremely frigid zones is defeated
Send in pipeline, due to the change in weather or season, be also readily formed gas hydrates, result in blockage, i.e., it is usually said
Ice block up phenomenon, influence normally to transport and safety.At present, the expense for suppressing hydrate generation accounts for the 5% of production of hydrocarbons cost
~8%.In the near future, in the exploitation transport process of gas hydrates, with greater need for take precautions against gas hydrates generation,
Effective managing risk.
Prevent the method that hydrate generates from mainly having two kinds, i.e. physical method and chemical method.Physical method is to make oil gas
System does not possess thermodynamic (al) formation condition, has voltage drop method, temperature-raising method and except three kinds of water law；Chemical method then mainly passes through addition
Some chemical addition agents are formed changing the nucleus of hydrate, the property in terms of crystal growth or aggregation suppresses the life of hydrate
Into.These chemical addition agents mainly have thermodynamic inhibitor, kinetic inhibitor, three kinds of polymerization inhibitor.Research and practice have shown that
Physical method has certain inhibition, but because its cost is high, application limitation is big, therefore physical method application relatively has
Limit, it is generally used to do the rescue method after auxiliary rejection condition and pipeline obstruction.Chemical method have simple, economy, species it is more,
The advantages that effect is good, it is to prevent most extensive, the most promising method of hydrate generation at present.Conventional thermodynamic inhibitor has first
The soluble alcohols such as alcohol, ethanol, ethylene glycol, inorganic salts etc..Thermodynamic inhibitor is once widely used in oil ＆ gas industry, but uses
Amount is big (concentration in aqueous will reach mass fraction can just have preferable inhibition for 10%~60%), cost it is high and
Environment is polluted, is just gradually eliminated.Using kinetic inhibitor and polymerization inhibitor as representative low-dosage inhibitor (in aqueous
Can be effectively for 0.5%~2% as long as concentration reaches mass fraction) just turning into the master that oil ＆ gas industry is used to suppress hydrate generation
Want chemical addition agent.Polymerization inhibitor is some surfactants or polymer, can be mixed with oil phase and be adsorbed to hydrate
The surface of grain, hydrate crystal grain is dispersed in suspension within condensation phase, so as to prevent hydrate aggregation caking, reach and suppress its obstruction
The purpose of pipeline.Kinetic inhibitor can delay the nucleation time of hydrate crystal, reduce the speed of growth, prevent hydrate brilliant
The further growth of body, the generation of hydrate in pipeline can be effectively prevented and treated, the generation of dynamic control risk, reduces production of hydrocarbons
Cost, increase production of hydrocarbons benefit.
At present, poly-N-vinylcaprolactam (PNVCL) is that a kind of temperature with lower critical solution temperature (LCST) is quick
Perceptual (Thermo-sensitive) high polymer, has the advantages of good biocompatibility and small bio-toxicity, is grown in medical science and pharmaceutically
Phase and be widely applied.Turn into the focus of research as dynamic hydrate inhibitor in recent years, can individually or and thermodynamics
Inhibitor compounds, and widely applies in natural gas, Oil/gas Well and conveyance conduit, has dosage few, efficient, small etc. to environmental hazard
Feature.But there is poorly water-soluble, (degree of supercooling be more than 12 DEG C) under the conditions of higher degree of supercooling loses inhibition the defects of in it.
Promote researcher constantly to explore, make every effort to develop efficient, applied widely, high financial profit and environment-friendly new type water
Compound inhibitors.
The content of the invention：
The purpose of the present invention is in view of the shortcomings of the prior art, there is provided a kind of novel hydrates kinetic inhibitor, the suppression
Preparation is water-soluble very well, and inhibitory activity is high, can obtain good inhibition, and dosage is few, and cost reduces, suitable for oil gas water three
Phase or profit or air water two-phase coexistent system, have wide applicability, are not restricted by degree of supercooling and application scenario.
The present invention is achieved by the following technical programs：
A kind of hydrate dynamic inhibitor of structural formula as shown in formula I, the hydrate dynamic inhibitor are carboxyl
The poly N-vinyl caprolactam of change, it is polymerized by mercaptan carboxylic acid and N- vinylcaprolactam monomers；
Wherein n=100~40000, R are * (CH2) m*, m=1~5.
The volume ratio of mercaptan carboxylic acid and N- the vinylcaprolactam monomer is 1:20~5:1.
Average molecular weight Mw=100~400000 of the hydrate dynamic inhibitor.
Preferably, the mercaptan carboxylic acid is TGA.
The preparation method of the hydrate dynamic inhibitor, comprises the following steps：By chain initiator azodiisobutyronitrile,
N- vinylcaprolactams monomer and mercaptan carboxylic acid mix in DMF solvent, in nitrogen atmosphere in 40~
Reacted 4~20 hours at a temperature of 150 DEG C；Obtained head product is recrystallized after being cooled to room temperature, filtered, being dried, and obtains mesh
Mark product；The initiator amount accounts for 0.5wt%~1.5wt% of solvent load；Mercaptan carboxylic acid and N- vinylcaprolactams
The volume ratio of monomer is 1:20~5:1；Solvent load is 2-10 times of N- vinylcaprolactam monomer volumes.
The reagent of recrystallization is cold ether.
The present invention also protects the application of the hydrate dynamic inhibitor, and the hydrate inhibitor is applied to oil gas water
The generation of hydrate in three-phase system, profit or air water two-phase system, relative to the dense of water when the hydrate inhibitor uses
It is 1~25MPa to spend for 0.1wt%~20wt%, applicable pressure, and temperature is -25~25 DEG C.
Relative to the concentration of water it is preferably 0.1wt%~10wt% when the hydrate inhibitor uses.
Beneficial effects of the present invention are as follows：
(1) present invention is used as kinetic inhibitor polymer, and carboxyl is added on poly N-vinyl caprolactam polymeric chain,
Therefore the polymeric water-soluble is fine, has wide applicability, suitable for oil gas water three phase or profit or air water two-phase coexistent
System, applied to the generation for suppressing hydrate in oil-gas mining, processing and course of conveying.
(2) inhibitory activity of the present invention is high, and dosage is few, and cost reduces：Because the hydrophilic radical of carboxyl preferably, on carboxyl
Oxygen atom can with hydrone formed hydrogen bond, so as to prevent guest molecule to be contacted with hydrone.The addition of such a inhibitor
Far smaller than conventional heat inhibitor, run-of-the-mill concentration are about 0.1~10wt%, and reagent cost substantially reduces.
In a word, the present invention is water-soluble very well, and inhibitory activity is high, can obtain good inhibition, and dosage is few, cost drop
It is low, have the advantages that low dosage, efficiently, applicability it is wide, can be under low dosage concentration (0.1~10wt%), high supercooling degree environment
It middle use, can effectively delay hydrate nucleation time, hydrate generating rate be reduced, suitable for oil gas water three phase or profit or gas
Water two-phase coexistent system, applied to the generation for suppressing hydrate in oil-gas mining, processing and course of conveying, not by degree of supercooling and answer
Restricted with occasion, there is the prospect of wide application.
Brief description of the drawings：
Fig. 1 is the carbon-13 nmr spectra figure of the product of embodiment 1；
Fig. 2 is the infrared spectrogram of the product of embodiment 1.
Embodiment：
It is to further explanation of the invention, rather than limitation of the present invention below.
Embodiment 1：The synthesis of hydrate dynamic inhibitor (abbreviation PVCSCOOH) of the structural formula as shown in formula II
Wherein, n average value is 115.
Synthetic method comprises the following steps：Weigh chain initiator azodiisobutyronitrile 176mg, N- vinylcaprolactam list
Body 10g, TGA 0.28mL, DMF 50mL is measured in 100mL eggplant shaped reaction bottles, after being sealed with rubber stopper
Vacuumize-lead to nitrogen 3 times, then with liquid nitrogen frozen-pumping-ramp cycle 3 times；Reacted in nitrogen atmosphere under the conditions of 80 DEG C of oil baths
12 hours；Obtained head product is cooled to after room temperature to be slowly dropped into 500mL cold diethyl ethers and is recrystallized, filtered, gained solid
Dried 1 hour under the conditions of 105 DEG C after being dried 48 hours under the conditions of 45 DEG C in vacuum drying chamber, obtain target product and divide equally again
Son amount (Mw) is 15892, its13CNMR spectrograms (CD3CN makees solvent) as shown in figure 1, chemical shift δ positioned at 30.52,34.76,
35.79th, 42.14,42.77,43.70,46.41,49.59,171.61 absworption peak difference correspondence position 8,4,2,3,5,6,7,9
Carbon atom absworption peak, δ corresponds to the absworption peak of carboxyl at 22.98 and 174.40.Its infrared spectrogram is as shown in Fig. 2 IR
Wave number is~1680cm in spectrogram-1It is C=O absworption peaks, wave number is~1300cm-1It is-C-N absworption peaks, wave number is~3500cm-1,~3000cm-1,~1680cm-1,~1250cm-1It is carboxyl characteristic absorption peak.
Embodiment 2：Inhibition is evaluated
The evaluation method of inhibition of the present invention is as follows：
Experimental facilities is visualization high-pressure stirring experimental provision, and the device chief component reacts including sapphire highpressure
Kettle, magnetic stirring apparatus, air bath, temperature and pressure transmitter, vavuum pump, gas cylinder and data collecting instrument etc..The sapphire highpressure
Reactor maximum working pressure 11MPa, operating temperature range -30~100 DEG C.Air bath can provide -30~100 DEG C of constant temperature
Degree.The parameter such as pressure, temperature and rotating speed in data collecting system collection in real time and storage reactor kettle.The formation of hydrate can lead to
Temperature or pressure change when crossing reaction are judged or visualized that form is directly observed.After reaction starts, pressure is dashed forward in kettle
The point that so decline, temperature rise simultaneously is the starting point of hydrate generation.Hydrate induction time is exactly that gas is passed through in kettle, pressure
Constant power is 8.0MPa, starts the time declined, temperature while rising are undergone occur to pressure.Hydrate generates the time completely
To be passed through gas in reactor, it is 8.0MPa that pressure, which starts constant, and the undergone time is balanced to reaction.The work of new inhibitor
It can be quantified with effect according to the induction time of hydrate, reaction deadline.Time is longer, and inhibition is better.
Specific implementation process：
Reaction experiment temperature is set to 2 DEG C, and experimental pressure 8.0MPa, experimental gas is methane.Methane hydrate generates at 2 DEG C
Balance pressure 3.20MPa.Before experiment operation, reactor is first cleaned repeatedly with deionized water three to five times, then purged with nitrogen
Reactor and experiment pipe-line system, it is ensured that system is dried.Reactor is vacuumized, sucks 12.0mL deionized water or preparation
Hydrate inhibitor solution, to exclude air in kettle, the methane gas of 1MPa purity 99.99% is first passed through, is then vacuumized again,
So 3 times repeatedly, the experimental gas less than 1MPa is finally passed through, ensures malleation in kettle and is not reaching to the bar of hydrate generation
Part.Start low temperature thermostat bath to cool to autoclave, until temperature in the kettle reaches 2 DEG C.After temperature stabilization, air inlet is opened
Valve, gas cylinder valve is opened, be passed through methane (entering precooling before reactor) until pressure reaches 8.0MPa in kettle.Start to start magnetic force
Agitator, and keep rotating speed 800rmp.Because methane is dissolved in water, experiment start time pressure slightly declines.Use form simultaneously
Observation and temperature, pressure change curve method, judge whether hydrate generates.
It is 198653 by weight average molecular weight, mass concentration is respectively 0.1%, 0.5%, 1% and 2% poly N-vinyl pyrrole
Network alkanone (abbreviation PVP K90) aqueous solution is added in reactor and tested, as a result as shown in table 1.
By weight average molecular weight be 12531, mass concentration be respectively 0.1%, 0.5%, 1% and 2% poly N-vinyl oneself
Lactam aqueous solution is added in reactor and tested, as a result as shown in table 1.
The weight average molecular weight that embodiment 1 is obtained is 15892 hydrate dynamic inhibitor (abbreviation PVCSCOOH) water
Solution is respectively to be tested in 0.1%, 0.5%, 1% and 2% addition reactor by mass concentration, as a result as shown in table 1.
Table 1
As shown in Table 1, the present invention can use, can have under low dosage concentration (0.1~2wt%) in high supercooling degree environment
Effect delays hydrate nucleation time, reduces hydrate generating rate, have the advantages that low dosage, efficiently, applicability it is wide, with compared with
Good inhibition.
Claims (6)
1. a kind of hydrate dynamic inhibitor of structural formula as shown in formula I, the hydrate dynamic inhibitor is carboxylated
Poly N-vinyl caprolactam, be polymerized by mercaptan carboxylic acid and N- vinylcaprolactam monomers；
Wherein n=100~40000, R are * (CH2) m*, m=1~5.
2. hydrate dynamic inhibitor according to claim 1, it is characterised in that mercaptan carboxylic acid and the N- vinyl
The volume ratio of caprolactam monomer is 1:20~5:1.
3. the preparation method of the hydrate dynamic inhibitor described in a kind of claim 1, it is characterised in that including following step
Suddenly：Chain initiator azodiisobutyronitrile, N- vinylcaprolactams monomer and mercaptan carboxylic acid is molten in N,N-dimethylformamide
Mix, reacted 4~20 hours at a temperature of 40~150 DEG C in nitrogen atmosphere, it is laggard that obtained head product is cooled to room temperature in agent
Row is recrystallized, filtered, being dried to obtain target product；The initiator amount accounts for 0.5wt%~1.5wt% of solvent load；Mercapto
The volume ratio of yl carboxylic acid and N- vinylcaprolactam monomers is 1:20~5:1；Solvent load is N- vinylcaprolactam lists
2-10 times of body volume.
4. the application of the hydrate dynamic inhibitor described in claim 1.
5. the application of hydrate dynamic inhibitor according to claim 4, it is characterised in that the hydrate inhibitor
Applied to the generation of hydrate in oil gas water three phase system, profit or air water two-phase system, when the hydrate inhibitor uses
Concentration relative to water is 0.1wt%~20wt%, and it is 1~25MPa to be applicable pressure, and temperature is -25~25 DEG C.
6. the application of hydrate dynamic inhibitor according to claim 5, it is characterised in that the hydrate inhibitor
Relative to the concentration of water it is 0.1wt%~10wt% during use.
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| CN201610861462.1A CN107868156B (en) | 2016-09-27 | 2016-09-27 | A kind of novel hydrates kinetic inhibitor |
| PCT/CN2016/109355 WO2018058786A1 (en) | 2016-09-27 | 2016-12-11 | Novel hydrate kinetic inhibitor |
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| CN201610861462.1A CN107868156B (en) | 2016-09-27 | 2016-09-27 | A kind of novel hydrates kinetic inhibitor |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109705246A (en) * | 2018-12-14 | 2019-05-03 | 中国科学院广州能源研究所 | A kind of hydrate dynamic inhibitor |
| CN111116798A (en) * | 2019-12-24 | 2020-05-08 | 中国科学院广州能源研究所 | Modified natural gas hydrate kinetic inhibitor |
| CN111285969A (en) * | 2020-03-06 | 2020-06-16 | 中国科学院广州能源研究所 | Hyperbranched amide hydrate kinetic inhibitor and preparation method and application thereof |
| CN111649237A (en) * | 2020-01-16 | 2020-09-11 | 中石化中原石油工程设计有限公司 | Ground gathering and transporting system for exhausted gas reservoir |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112877047B (en) * | 2021-01-27 | 2022-08-23 | 四川柏诗特能源科技有限公司 | Efficient prevention and control agent and process for solving low-temperature freezing and blocking of natural gas production pipeline |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109705246A (en) * | 2018-12-14 | 2019-05-03 | 中国科学院广州能源研究所 | A kind of hydrate dynamic inhibitor |
| CN109705246B (en) * | 2018-12-14 | 2020-05-05 | 中国科学院广州能源研究所 | Hydrate kinetic inhibitor |
| WO2020118780A1 (en) * | 2018-12-14 | 2020-06-18 | 中国科学院广州能源研究所 | Hydrate kinetics inhibitor |
| US11919978B2 (en) | 2018-12-14 | 2024-03-05 | Guangzhou Institute Of Energy Conversion, Chinese Academy Of Sciences | Hydrate kinetics inhibitor |
| CN111116798A (en) * | 2019-12-24 | 2020-05-08 | 中国科学院广州能源研究所 | Modified natural gas hydrate kinetic inhibitor |
| CN111116798B (en) * | 2019-12-24 | 2021-07-23 | 中国科学院广州能源研究所 | Modified natural gas hydrate kinetic inhibitor |
| CN111649237A (en) * | 2020-01-16 | 2020-09-11 | 中石化中原石油工程设计有限公司 | Ground gathering and transporting system for exhausted gas reservoir |
| CN111649237B (en) * | 2020-01-16 | 2021-11-26 | 中石化中原石油工程设计有限公司 | Ground gathering and transporting system for exhausted gas reservoir |
| CN111285969A (en) * | 2020-03-06 | 2020-06-16 | 中国科学院广州能源研究所 | Hyperbranched amide hydrate kinetic inhibitor and preparation method and application thereof |
| WO2021159835A1 (en) * | 2020-03-06 | 2021-08-19 | 中国科学院广州能源研究所 | Hyperbranched amide hydrate kinetic inhibitor and preparation method therefor and application thereof |
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| Publication number | Publication date |
|---|---|
| CN107868156B (en) | 2019-10-08 |
| WO2018058786A1 (en) | 2018-04-05 |
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