CN103833573A - Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control - Google Patents
Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control Download PDFInfo
- Publication number
- CN103833573A CN103833573A CN201210471500.4A CN201210471500A CN103833573A CN 103833573 A CN103833573 A CN 103833573A CN 201210471500 A CN201210471500 A CN 201210471500A CN 103833573 A CN103833573 A CN 103833573A
- Authority
- CN
- China
- Prior art keywords
- hydrophobic monomer
- reaction
- monomer based
- synthesis technique
- twin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a synthesis technology of a twin-tailed hydrophobic monomer based on reaction temperature control. The technology comprises the following steps: 1, dissolving acryloyl chloride in a dichloromethane solution; 2, adding the above obtained acryloyl chloride and dichloromethane mixed solution, dibutylamine and an aqueous solution of NaOH into a reaction container, and fully shaking; 3, placing the reaction container in a 5-7DEG C water bath; 4, stirring, and letting in an inert gas; 5, separating out an organic layer, and washing; 6, drying, and carrying out reduced pressure distillation to vaporize a solvent in order to obtain a light yellow oily liquid; and 7, adding a polymerization inhibitor, and carrying out reduced pressure distillation under a certain degree of vacuum at a certain temperature to obtain a colorless oily liquid which is a target product. The twin-tailed hydrophobic monomer can be successfully synthesized through the technology, and the synthesized twin-tailed hydrophobic monomer has the advantages of excellent performances, simple synthesis steps and substantially reduced synthesis cost; and the reaction temperature in the synthesis process is controlled to improve the yield of the product.
Description
Technical field
The present invention relates to a kind of synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction.
Background technology
Hydrophobic associated water-soluble polymer is in the hydrophilic backbone of polymkeric substance, to introduce minute quantity hydrophobic grouping and a kind of water-soluble polymers of forming.In the aqueous solution, the hydrophobic grouping of hydrophobic associated water-soluble polymer, because hydrophobic effect trends towards associating together, forms in molecule and intermolecular association.Hydrophobic associated water-soluble polymer shows the special flow sex change that is different from general water-soluble polymers, these characteristics make hydrophobic associated polymer in many industrial technologies as the fields such as intensified oil reduction, washing, coating all show huge potentiality, thereby the exploration of hydrophobic associated water-soluble polymer is become to recent two decades carry out one of problem the most interesting in water-soluble polymers research field, and become the focus that industry and academia are studied.
Hydrophobic associated water-soluble polymer, comprises hydrophobically modified water-soluble polymers, refers to the water-soluble polymers with a small amount of hydrophobic grouping on polymer hydrophilicity macromolecular chain.On water-soluble macromolecule chain, introducing a small amount of hydrophobic grouping makes its aqueous solution show unique rheological property.On certain polymer concentration, hydrophobic part associates and forms dynamic three-dimensional net structure, thereby forms very large supramolecule chain aggregation body, increases the hydrodynamic volume of polymkeric substance, improves significantly the viscosity of solution.The electrolytical polarity that can increase solvent that adds of small molecules, strengthens hydrophobic association effect, produces obvious salt resistance.Under high shear forces, the dynamic physical cross-linked network structure that hydrophobic association forms is destroyed, soltion viscosity declines, shearing action reduction or the physical crosslinking of eliminating between rear macromolecular chain form again, viscosity will be recovered again, the irreversible machinery degraded of the polymkeric substance that general high molecular do not occur under high shear rate.Just because of its unique SOLUTION PROPERTIES, it may be applied in a lot of fields, as tertiary oil recovery, pharmacy, solar energy converting, makeup, coating, water treatment and flow improver etc.Its correlative study in recent years receives much attention.
Hydrophobic close ester phenomenon is very general, as far back as nineteen twenty, in formation micella process, has the association between hydrocarbon group.Below critical association concentration, mainly form in molecule and associate, consequently make a ball of string shrink, hydrodynamic volume reduces; More than CAC, main formation take Interpolymer Association as main supramolecular structure has good tackifying.By Interpolymer Association, on the macro property of solution, show the feature that tackifying is strong, have certain temperature resistance, anti-salt and anti-shear ability.These special performances of hydrophobic associated polymer make it in many industrial technologies, all show huge application potential, and have great importance for the solution behavior that imitates the amphiphilic class material in life entity, thereby the exploration of hydrophobic associated water-soluble polymer is become to recent two decades carry out one of problem the most interesting in water-soluble polymers research field, and become the focus that industry and academia are studied.
Hydrophobic associated water-soluble polymer is by the atom difference that forms main chain, can be divided into carbochain and heteroatoms molecular backbone chain polymkeric substance, the former is mainly the multipolymer being obtained by the alkene monomer polymer of hydrophilic radical and hydrophobic grouping, what hydrophilic monomer was conventional mainly contains acrylamide and vinylformic acid etc., and hydrophobic monomer mainly contains acrylamide derivative, long-chain acrylate etc.; The latter mainly passes through water-soluble high-molecular compound modification through macromolecular reaction, introduces hydrophobic functional group.Macromolecular reaction method advantage is directly to make starting raw material with commercial polymer, and the product relative molecular mass obtaining is high, and its shortcoming is that reaction is carried out in full-bodied polymers soln, and reactant is not easy to mix.Natvosol (HEC) can be reacted with the hydrophobic compound with active group in this way, these hydrophobic compounds can be with the epoxy compounds of chain alkyl, halohydrocarbon, carboxylic acid halides, isocyanic ester etc., also can be at polyoxyethylene glycol (PEG) two termination hydrophobic groupings, but the amount of the general hydrophobic grouping of introducing is all little, because the high solvability that can significantly reduce water-soluble polymer of content of hydrophobic monomers, and heteroatoms trunk polymer is compared with carbon chain polymer, thermostability is poor.Because when the carbon atom in macromolecular chain is replaced by heteroatomss such as oxygen, sulphur, nitrogen, the bond energy of C-O, C-S, C-N key is lower than C-C key, and polymer thermostable reduces.Therefore be, mainly the multipolymer being obtained by the vinyl monomer polymerization of hydrophilic radical and hydrophobic grouping for the hydrophobic associated water-soluble polymer of tertiary oil production in oil field at present.The conventional hydrophilic monomer of hydrophobic associated polymer that utilizes process for copolymerization to prepare is acrylamide (AM), because acrylamide is suitable for preparing the water-soluble polymers of high molecular, reasonable price.In addition, in order to increase the solvability of multipolymer, the anionic monomer that also can add other as vinylformic acid (methacrylic acid), vinylsulfonate, 2-methyl-2-acrylamido propanesulfonic acid (AMPS) etc. with cationic monomer as β-dimethyl-aminoethylmethacrylate base trimethyl ammonium chloride, 2-acrylimide base-2-trimethoxysilyl propyl methacrylate ammonium chloride (AMPTAC), diallyldimethylammonium chloride etc.
The synthetic main indexes of twin tail hydrophobic monomer is the productive rate of product, its influence factor comprises proportioning raw materials, temperature of reaction, alr mode and reaction times etc., suitable temperature of reaction of how to confirm, seems particularly important to the synthesis technique of twin tail hydrophobic monomer.
Summary of the invention
The object of the invention is to overcome the shortcoming and defect of above-mentioned prior art, a kind of synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction is provided, this synthesis technique can successfully synthesize twin tail hydrophobic monomer, and the excellent property of the twin tail hydrophobic monomer synthesizing, synthesis step is simple, greatly reduces synthetic cost; And by controlling the temperature of reaction in building-up process, thereby improve the productive rate of product.
Object of the present invention is achieved through the following technical solutions: a kind of synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction, comprises the following steps:
(a) first, acrylate chloride is dissolved in dichloromethane solution;
(b) then, acrylate chloride and methylene dichloride mixing solutions, Di-n-Butyl Amine, the NaOH aqueous solution are added in reaction vessel, fully shake up;
(c) then, reaction vessel is placed in to 5～7 ℃ of water-baths;
(d) stir and pass into rare gas element;
(e) separate organic layer washing;
(f) dry, underpressure distillation steams solvent, obtains light yellow oily liquid;
(g) add stopper, underpressure distillation at certain vacuum degree and temperature, obtains colourless oil liquid and is target product.
Described rare gas element is nitrogen.
In described step (e), separate organic layer by separating funnel.
In described step (f), carry out underpressure distillation by rotatory evaporator.
In described step (e), first use distilled water wash 2 times, then with concentrated sodium chloride solution washing 1 time.
Described stopper is cuprous chloride.
Described siccative is anhydrous magnesium sulfate.
Described temperature of reaction is 5.5 ℃.
Described temperature of reaction is 6.5 ℃.
Temperature of reaction is 6.0 ℃.
In sum, the invention has the beneficial effects as follows: can successfully synthesize twin tail hydrophobic monomer, and the excellent property of the twin tail hydrophobic monomer synthesizing, synthesis step is simple, greatly reduces synthetic cost; And by controlling the temperature of reaction in building-up process, thereby improve the productive rate of product.
Accompanying drawing explanation
fig. 1 is the affect schematic diagram of temperature of reaction on productive rate.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited only to this.
Embodiment:
The synthesis technique of a kind of twin tail hydrophobic monomer based on control temperature of reaction the present invention relates to, comprises the following steps:
(a) first, acrylate chloride is dissolved in dichloromethane solution;
(b) then, acrylate chloride and methylene dichloride mixing solutions, Di-n-Butyl Amine, the NaOH aqueous solution are added in reaction vessel, fully shake up;
(c) then, reaction vessel is placed in to 5～7 ℃ of water-baths;
(d) stir and pass into rare gas element;
(e) separate organic layer washing;
(f) dry, underpressure distillation steams solvent, obtains light yellow oily liquid;
(g) add stopper, underpressure distillation at certain vacuum degree and temperature, obtains colourless oil liquid and is target product.
Described rare gas element is nitrogen.
In described step (e), separate organic layer by separating funnel.
In described step (f), carry out underpressure distillation by rotatory evaporator.
In described step (e), first use distilled water wash 2 times, then with concentrated sodium chloride solution washing 1 time.
Described stopper is cuprous chloride.
Described siccative is anhydrous magnesium sulfate.
The synthetic main indexes of twin tail hydrophobic monomer is the productive rate of product, and temperature of reaction is its important influence factor, and suitable temperature of reaction of how to confirm, seems particularly important to the synthesis technique of twin tail hydrophobic monomer.In order to obtain best temperature of reaction, the present invention has done the impact experiment of differential responses temperature on product yield, and experimental result as shown in Figure 1, as shown in Figure 1: along with the increase of temperature, reaction yield raises gradually, and when temperature of reaction is during at 5 ℃, it is maximum that reaction yield reaches.Increase temperature, productive rate lowers gradually, and changing down is very fast again.Because acrylate chloride is highly active chemical substance, need to react at a lower temperature.So it is 5 ℃ that synthon is selected optimal reaction temperature.
The above, be only preferred embodiment of the present invention, not the present invention done to any pro forma restriction, every foundation technical spirit of the present invention, and any simple modification, equivalent variations that above embodiment is done, within all falling into protection scope of the present invention.
Claims (10)
1. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction, is characterized in that, comprises the following steps:
(a) first, acrylate chloride is dissolved in dichloromethane solution;
(b) then, acrylate chloride and methylene dichloride mixing solutions, Di-n-Butyl Amine, the NaOH aqueous solution are added in reaction vessel, fully shake up;
(c) then, reaction vessel is placed in to 5～7 ℃ of water-baths;
(d) stir and pass into rare gas element;
(e) separate organic layer washing;
(f) dry, underpressure distillation steams solvent, obtains light yellow oily liquid; ;
(g) add stopper, underpressure distillation at certain vacuum degree and temperature, obtains colourless oil liquid and is target product.
2. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, described rare gas element is nitrogen.
3. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, in described step (e), separates organic layer by separating funnel.
4. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, in described step (f), carries out underpressure distillation by rotatory evaporator.
5. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, in described step (e), first uses distilled water wash 2 times, then with concentrated sodium chloride solution washing 1 time.
6. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, described stopper is cuprous chloride.
7. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, described siccative is anhydrous magnesium sulfate.
8. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, described temperature of reaction is 5.5 ℃.
9. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, described temperature of reaction is 6.5 ℃.
10. the synthesis technique of the twin tail hydrophobic monomer based on control temperature of reaction according to claim 1, is characterized in that, temperature of reaction is 6.0 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210471500.4A CN103833573A (en) | 2012-11-20 | 2012-11-20 | Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210471500.4A CN103833573A (en) | 2012-11-20 | 2012-11-20 | Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103833573A true CN103833573A (en) | 2014-06-04 |
Family
ID=50797514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210471500.4A Pending CN103833573A (en) | 2012-11-20 | 2012-11-20 | Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103833573A (en) |
-
2012
- 2012-11-20 CN CN201210471500.4A patent/CN103833573A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104744650A (en) | Preparation and application of hybrid copolymer containing POSS (polyhedral oligomeric silsesquioxane) base | |
| CN103837448A (en) | Method for testing influence of surfactant on apparent viscosity of hydrophobic association polymer | |
| CN103833573A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on reaction temperature control | |
| CN103833577A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on drying temperature control | |
| CN103833584A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on reaction time control | |
| CN103833572A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on distillation temperature control | |
| CN103833575A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on stirring time control | |
| CN103833580A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on drying time control | |
| CN103833582A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on distillation time control | |
| CN103833571A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on stirring mode control | |
| CN103833574A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on distillation pressure control | |
| CN103833568A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on inert gas introduction speed control | |
| CN103833581A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on cooling time control | |
| CN103833578A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on stirring speed control | |
| CN103833583A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on reaction monomer concentration control | |
| CN103833567A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on pH value control | |
| CN103833585A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on cooling temperature control | |
| CN103833576A (en) | Synthesis technology of twin-tailed hydrophobic monomer based on raw material ratio control | |
| CN106478463B (en) | A kind of temperature-resistant anti-salt monomer and polymer and its preparation method and application | |
| CN103833579A (en) | Synthesis technology of twin-tailed hydrophobic monomer | |
| CN103833898A (en) | Synthesis technology of twin-tailed hydrophobic association polymer based on reaction temperature control | |
| CN103833901A (en) | Synthesis technology of twin-tailed hydrophobic association polymer based on hydrophobic monomer addition amount control | |
| CN103833905A (en) | Synthesis technology of twin-tailed hydrophobic association polymer based on stirring speed control | |
| CN103837438A (en) | Method for determining intrinsic viscosity of twin-tailed hydrophobic association polymer | |
| CN103833893A (en) | Synthesis technology of twin-tailed hydrophobic association polymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140604 |