CN107445857A - A kind of preparation method of the chain alkyl acid amido propyl dimethylamine with CO2 response performances - Google Patents
A kind of preparation method of the chain alkyl acid amido propyl dimethylamine with CO2 response performances Download PDFInfo
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Abstract
The present invention provides a kind of preparation method of the chain alkyl acid amido propyl dimethylamine with CO2 response performances, and being related to several has CO2Preparation, purification, structure and the CO of the chain alkyl acid amido propyl diformazan amines of response performance2Response characterizes.It is described that there is CO2The chain alkyl acid amido propyl dimethylamine of response performance includes palmitic acid amido propyl dimethylamine, stearic amide diemethylamine, oleamide diemethylamine and behenamide diemethylamine, and preparation temperature is relatively low, method is simple and yield is high.Chain alkyl acid amido propyl dimethylamine agueous solution has CO2Response, it is passed through CO2Phase transformation can be brought it about, can be applied to the reaction and separation of opposed polarity demand, its aqueous solution can be used as CO2Response type gel.Compound prepared by the present invention can also be used for oil gas field and improve recovery ratio application.
Description
Technical field
The invention belongs to oilfield exploitation product technique field, and in particular to a kind of chain alkyl with CO2 response performances
The preparation of sour amido propyl dimethylamine and method of purification.
Background technology
The unique tertiary amine molecule structure of chain alkyl acid amido propyl diformazan amine end groups assigns its outstanding CO2Response
Energy.Pass through CO2Induction, the controllable body of the response of another physical property structure can be changed into from a kind of physical property structure
System.I.e. in CO2Under induction, molecule can be changed into highly polar structure from low polar structure, can use it for different needing difference
In the reaction or separation process of polar solvent.
Pass through CO2Induction, makes chain alkyl acid amido propyl diformazan amine end groups be changed into strong from the tertiary amine structure of slightly water-wet
Hydrophilic quaternary ammonium structure, whole molecule are also changed into the strong ionic surface of hydrophily by nonionic surfactant form and lived
Property agent.Due to chain alkyl structure, easily wind in aqueous, easily form vermiculate glues, System forming gel and
With good viscoplasticity, it can be applied to Oil/gas Well water blockoff and well fracturing use.Continue to lead in the system for forming gel
Cross inert gas (such as：Air, argon gas etc.) system can revert to the tertiary amine class formation of slightly water-wet again.The system plastic of realization is broken
The circulation of glue is controllable.
Chinese patent CN201510792794, it was recently reported that utilize erucic acid and diemethylamine reaction generation erucyl amide propyl group
Dimethylamine, but do not have the sign of specific catalysts, purification process and final products.CN201210047173, ACS
Sustainable Chem.Eng.2013,1,75-79 are reported by erucic acid and diemethylamine synthetic mesophase system erucic acid acyl
Amine diemethylamine further reacts generation glycine betaine, does not there is purifying and the table of intermediate erucyl amide diemethylamine
Sign.At present report be concentrated mainly on by long chain acid amido propyl dimethylamine be chemical reactive synthesis raw material generation glycine betaine and its
Derivative, severe reaction conditions during betaines compound synthesis, accessory substance is more, and purification is complex, it is difficult to obtains purity
Higher betaines surfactant.
The end-product long chain acid amido propyl dimethylamine of this report is the intermediate of glycine betaine synthetic reaction, it is possible to reduce is closed
Into step and there is its unique CO2Response performance.Report and limited by catalysts and purification process before, required temperature
It is higher not have good transformation efficiency and purification step.Therefore, how efficient easy to synthesize with CO2Response
The surfactant of energy is most important, particularly its detailed synthetic method and method of purification, for such surfactant
Popularization and application have great importance.
The content of the invention
It is an object of the invention to provide one kind to have CO2The preparation of the chain alkyl acid amido propyl dimethylamine of response and carry
Pure method, and to product structure and CO2Response performance is characterized.
It is provided by the present invention that there is CO2The chain alkyl acid amido propyl dimethyl amine compound of response, the long-chain
The formula of alkyl acid amido propyl dimethyl amine compound is as follows：
Wherein R is C13H27,C15H29, C15H31Or C19H39。
As the specific record of embodiment, described chain alkyl acid amido propyl dimethyl amine compound is specific as follows：
Above-mentioned has CO2The preparation method of the chain alkyl acid amido propyl diformazan amines of response, includes
Following steps：
1) condensation reaction：
Chain alkyl acid and N, N- dimethylaminopropylamine are added to condenser pipe and fractional still head by certain mol proportion
In three-necked flask, catalyst is added, deicer is added in fractional still head, condensation reaction is carried out under the conditions of inert gas shielding, instead
Answer 120~150 DEG C of temperature, reaction a period of time；
2) purify：
Rotary evaporation removes unreacted N after reaction stops, and N- dimethylaminopropylamines, adds acetone and water in the crude product
Mixed solvent to remove catalyst and unreacted raw material impurity, filter simultaneously with the mixed solvent of acetone and water wash it is final must
To target product chain alkyl acid amido propyl dimethylamine.
Described chain alkyl acid, is palmitic acid, stearic acid, oleic acid and behenic acid.
Chain alkyl acid and N, N- dimethylaminopropylamine ratio are 1 in described step 1)：1-1.5 it is optimized for 1：1.2.
The catalyst is sodium fluoride.
Reaction time is 3-10 hour, is optimized for 6-8 hour.
The in the mixed solvent acetone of the acetone and water and the ratio of water are 1.5~2.5：1.
The deicer is any one or two kinds of in calcium chloride, alundum (Al2O3).
Chain alkyl acid amido propyl dimethylamine provided by the present invention is used for oil gas field and subsurface rock pressure break；Or
Application in reaction and separation that opposed polarity needs；
A kind of its application method, it is to be passed through CO in chain alkyl acid amido propyl dimethylamine agueous solution2It is used for oil gas afterwards
Field and subsurface rock pressure break.
The invention provides with CO2The preparation of the chain alkyl acid amido propyl diformazan amines of response performance, carry
Pure method, structural characterization and CO2Response performance.Preparation temperature is relatively low, method is simple and yield is high, need to only add catalyst and anti-
Answer and direct de-watering apparatus is accessed in device；Method of purification is simple and product purity is higher, only need to have specific blend solvent repeatedly to wash
It can obtain.Chain alkyl acid amido propyl dimethylamine agueous solution has CO2Response performance, it is passed through CO2Muddiness can be brought it about
The change of degree, viscosity and ionic formses.CO prepared by the present invention2Response type compound can be applied to the reaction of opposed polarity demand
And separation, low polarity and the reciprocal conversion of highly polar solvent can be achieved.Compound prepared by the present invention can also be used for oil gas field
Deng subsurface rock pressure break application.
Brief description of the drawings
Fig. 1：Oleamide diemethylamine nucleus magnetic hydrogen spectrum figure.
Embodiment
With reference to embodiment, the present invention will be further described：
Embodiment 1
1) by stearic acid and N, N- dimethylaminopropylamines in molar ratio 1：1.1 are added to three with condenser pipe and fractional still head
In mouthful flask, add sodium fluoride and be used as catalyst, in fractional still head addition calcium chloride as deicer to isolate by-product in time
Thing water, makes reaction be carried out to positive reaction direction, carries out condensation reaction under nitrogen protective condition, 130~150 DEG C of reaction temperature,
8 hours of reaction time.
2) and then rotary evaporation removes unreacted dimethylaminopropylamine, is 2 with acetone and water ratio：1 mixed solution is more
Secondary washing is to colourless, filtering, dry C23H48N2O white solids.Yield：99%,1HNMR(400MHz,Chloroform-d)δ
7.22s, (s, 1H), 3.47 (J=2.6Hz, 1H), 2.28 (J=9.4Hz, 2H), 2.11-1.95 (8H), 1.84 (2H), 1.51
(2H), 1.13 (J=13.2Hz, 28H), 0.78 (J=6.1,3H).Elementary analysis result：Theoretical value：C,74.94；H,13.12；
N,7.60；O,4.34.Experiment value：C,75.12；H,13.26；N,7.21；O,4.41.As a result show that products collection efficiency is high, purity is high.
Embodiment 2
By oleic acid and N, N- dimethylaminopropylamines in molar ratio 1：1.1 are added to three mouthfuls of burnings with condenser pipe and fractional still head
In bottle, add sodium fluoride and be used as catalyst, in fractional still head addition calcium chloride as deicer to isolate water byproduct in time,
Reaction is carried out to positive reaction direction, carry out condensation reaction under nitrogen protective condition, 130~150 DEG C of reaction temperature, during reaction
Between 8 hours.Then rotary evaporation removes unreacted dimethylaminopropylamine, is 2 with acetone and water ratio：1 mixed solution is more
Secondary washing is to colourless, liquid separation, dry C23H46N2O deep yellow color liquids.Yield：99%,1HNMR(400MHz,Chloroform-
d)ppm:δ 7.22 (s, 2H), 5.19 (J=2.5Hz, 2H), 3.17 (J=4.5Hz, 2H), 2.22 (J=9.1,6.4Hz, 3H),
2.12-1.88 (10H), 1.87 (s, 3H), 1.69-1.22 (7H), 1.15 (J=13.2Hz, 20H), 0.74 (J=6.3,
3.8Hz,3H).Elementary analysis result：Theoretical value：C,75.35；H,12.65；N,7.64；O,4.36.Experiment value：C,75.92；H,
12.26；N,6.97；O,4.85.As a result show that products collection efficiency is high, purity is high.
Embodiment 3
By palmitic acid and N, N- dimethylaminopropylamines in molar ratio 1：1.1 are added to three mouthfuls with condenser pipe and fractional still head
In flask, add sodium fluoride and be used as catalyst, in fractional still head addition calcium chloride as deicer to isolate accessory substance in time
Water, makes reaction be carried out to positive reaction direction, carries out condensation reaction under nitrogen protective condition, 130~150 DEG C of reaction temperature, instead
8 hours between seasonable.Then rotary evaporation removes unreacted dimethylaminopropylamine, is 2 with acetone and water ratio：1 mixing is molten
Repeatedly washing is to colourless for liquid, filtering, dry C21H44N2O white solid powders.Yield：99%,1HNMR(400MHz,
Chloroform-d)ppm:δ7.20(s,1H),3.29(2H),2.38(2H),2.15(8H),1.51(2H),1.16-1.21(J
=11.2Hz, 26H), 0.74 (t, J=4.7Hz, 3H) elementary analysis results：Theoretical value：C,74.06；H,13.02；N,8.22；
O,4.70.Experiment value：C,74.42；H,12.90；N,8.12；O,4.56.As a result show that products collection efficiency is high, purity is high.
Embodiment 4
By behenic acid and N, N- dimethylaminopropylamines in molar ratio 1：1.1 are added to three mouthfuls with condenser pipe and fractional still head
In flask, add sodium fluoride and be used as catalyst, in fractional still head addition calcium chloride as deicer to isolate accessory substance in time
Water, makes reaction be carried out to positive reaction direction, carries out condensation reaction under nitrogen protective condition, 130~150 DEG C of reaction temperature, instead
8 hours between seasonable.Then rotary evaporation removes unreacted dimethylaminopropylamine, is 2 with acetone and water ratio：1 mixing is molten
Repeatedly washing is to colourless for liquid, filtering, dry C28H56N2O white clumpy solids.Yield：99%,1HNMR(400MHz,
Chloroform-d) δ 7.22 (s, 1H), 3.41 (J=2.7Hz, 2H), 2.25 (J=9.4Hz, 2H), 2.12-1.90 (8H),
1.85 (2H), 1.49 (2H), 1.13 (J=14.9Hz, 38H), 0.77 (J=6.0,3H).Elementary analysis result：Theoretical value：C,
76.65；H,13.32；N,6.38；O,3.65.Experiment value：C,76.82；H,13.25；N,6.31；O,3.62.As a result product is shown
Yield is high, purity is high.
Embodiment 5：Chain alkyl acid amido propyl dimethyl amine compound has CO2Response
CO is passed through in the aqueous solution of chain alkyl acid amido propyl dimethylamine2Phase transformation can be brought it about, i.e., by muddiness
Liquid is changed into clarified solution, is changed into cationic from nonionic, is changed into high viscoelastic fluid from low viscosity fluid.
Found by studying for a long period of time, CO is being passed through in chain alkyl acid amido propyl dimethylamine agueous solution2Afterwards, system macroscopic view
State is changed into clear liquid from milky dirty solution；Shown in equation below, it is changed into from uncharged nonionic form with just
The quaternary ammonium salt cationic form of electric charge；The Newton type fluid for being similar to water viscosity from viscosity is changed into having very high viscoelastic height viscous
Non-Newtonian fluid, viscosity can increase more than three orders of magnitude greater.
Chain alkyl acid amido propyl dimethylamine agueous solution is passed through CO2Afterwards, CO occurs2Respond the reaction equation of change such as
Under：
The above results show that chain alkyl acid amido propyl dimethylamine agueous solution prepared by the present invention has CO2 responses
Can, the change of turbidity, viscosity and ionic formses can be brought it about by being passed through CO2.CO2 response type compounds prepared by the present invention
The reaction and separation of opposed polarity demand are can be applied to, low polarity and the reciprocal conversion of highly polar solvent can be achieved；So as to
In the subsurface rock pressure break application such as oil gas field.
Claims (10)
1. one kind has CO2The chain alkyl acid amido propyl dimethyl amine compound of response, it is characterised in that described long-chain
The formula of alkyl acid amido propyl dimethyl amine compound is as follows：
Wherein R is C13H27,C15H29, C15H31Or C19H39。
2. compound as claimed in claim 1, it is characterised in that described chain alkyl acid amido propyl dimethyl amine chemical combination
The structural formula of thing is
3. the preparation method of the compound described in claim 1, it is characterised in that described method includes having the following steps：
1) condensation reaction：
Chain alkyl acid and N, N- dimethylaminopropylamine are added to by certain mol proportion to three mouthfuls with condenser pipe and fractional still head
In flask, catalyst sodium fluoride is added, deicer is added in fractional still head, condensation reaction is carried out under the conditions of inert gas shielding,
120~150 DEG C of reaction temperature；
2) purify：
Rotary evaporation removes unreacted N after reaction stops, N- dimethylaminopropylamines, adds the mixed of acetone and water in the crude product
Bonding solvent is filtered and washed with the mixed solvent of acetone and water and finally give mesh to remove catalyst and unreacted raw material impurity
Mark product chain alkyl acid amido propyl dimethylamine.
4. method as claimed in claim 3, it is characterised in that described chain alkyl acid is palmitic acid, stearic acid, oleic acid or
Behenic acid.
5. method as claimed in claim 3, it is characterised in that chain alkyl acid and N, N- dimethylamino in described step 1)
Propylamine ratio is 1：1-1.5.
6. method as claimed in claim 3, it is characterised in that the reaction time in described step 1) is 3-10 hour.
7. method as claimed in claim 3, it is characterised in that the mixed solvent of the acetone and water in described step 2)
In, the ratio of acetone and water is 1.5~2.5：1.
8. method as claimed in claim 3, it is characterised in that the deicer in described step 2) is calcium chloride, three oxidations
It is any one or two kinds of in two aluminium.
9. the chain alkyl acid amido propyl dimethyl amine compound described in claim 1 is in oil gas field and subsurface rock pressure break
Application；Or the application in the reaction and separation that opposed polarity needs.
10. a kind of method of oil gas field and subsurface rock pressure break, it is characterised in that described method is by described in claim 1
Chain alkyl acid amido propyl dimethyl amine compound water solution in be passed through CO2It is used for oil gas field and subsurface rock pressure break afterwards.
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| CN108659808A (en) * | 2018-02-02 | 2018-10-16 | 中国地质大学（北京） | CO2It drives envelope and alters system and CO2The method of the displacement of reservoir oil |
| CN108865100A (en) * | 2018-05-29 | 2018-11-23 | 中国石油集团川庆钻探工程有限公司长庆井下技术作业公司 | One kind is reusable to drop the system that blocks water |
| CN110257042A (en) * | 2019-07-06 | 2019-09-20 | 西南石油大学 | A kind of reservoir breaks the clean fracturing fluid and preparation method thereof of glue automatically |
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| CN115850569A (en) * | 2022-12-08 | 2023-03-28 | 西南石油大学 | For micro-crack of cement stoneRepaired CO 2 Preparation method of responsive gel material |
| CN116023917A (en) * | 2021-10-26 | 2023-04-28 | 中国石油化工股份有限公司 | CO (carbon monoxide) 2 Responsive gel system, preparation method thereof and oil reservoir CO prevention 2 Leakage method |
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