CN108314750A - A method of synthesis Diacetone Acrylamide and acrylamide copolymer - Google Patents
A method of synthesis Diacetone Acrylamide and acrylamide copolymer Download PDFInfo
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- CN108314750A CN108314750A CN201810046622.6A CN201810046622A CN108314750A CN 108314750 A CN108314750 A CN 108314750A CN 201810046622 A CN201810046622 A CN 201810046622A CN 108314750 A CN108314750 A CN 108314750A
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- acrylamide
- diacetone acrylamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a kind of methods of synthesis Diacetone Acrylamide and acrylamide copolymer, it is using carbon dioxide as medium, using persulfate and Bisulphite redox system as initiator, more than the critical-temperature of carbon dioxide and pressure, precipitation polymerization is carried out to Diacetone Acrylamide and acrylamide comonomer, obtains Diacetone Acrylamide and acrylamide copolymer.A concentration of 0.05~0.5mol/l of initial content of initiator；Diacetone Acrylamide, the total monomer concentration of acrylamide are 1~8mol/l；Persulfate is one kind in potassium peroxydisulfate, sodium peroxydisulfate or ammonium persulfate in initiator, and bisulfites is one kind of potassium bisulfite, sodium hydrogensulfite or ammonium bisulfite.Since the present invention replaces organic solvent using nontoxic and pollution-free medium supercritical carbon dioxide, avoids using toxic, harmful, volatile and inflammable organic solvent pollution on the environment, effect that is environmentally protective, energy saving, economizing on resources may be implemented.
Description
Technical field
The present invention relates to a kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer, it is specifically a kind of with
Supercritical carbon dioxide is the method that solvent synthesizes Diacetone Acrylamide and acrylamide copolymer.
Background technology
The method of existing synthesis Diacetone Acrylamide and acrylamide copolymer, generally using solution polymerization, or
Aqueous deposited polymerization is carried out in water.Using solution polymerization, other than the process of solvent recovery to be increased, the organic or nothing that uses
Solvent is also easy to bring pollution to environment and polymerizate.And aqueous phase precipitation method is used, reaction product need to add deionized water dilute
It releases, acetone precipitation, washing and drying will not only expend a large amount of energy, but also can make process complications, make on production cost
It rises.
Invention content
Technical problem to be solved by the present invention lies in propose a kind of to replace conventional solvent synthesis pair third with supercritical carbon dioxide
The method of ketone acrylamide and acrylamide copolymer, the pollution to avoid organic solvent to environment adapt to environmentally protective, section
The requirement that can, economize on resources.
In order to solve the above technical problems, a kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer of the present invention
Using carbon dioxide as medium, using persulfate and Bisulphite redox system as initiator, in the critical of carbon dioxide
Temperature carries out precipitation polymerization to Diacetone Acrylamide and acrylamide comonomer, obtains diacetone acrylamide with more than pressure
Amide and acrylamide copolymer.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, it includes the following steps：It will be double
Reaction kettle is added in acetone acrylamide, acrylamide monomer and initiator, seals, and the initial content of the initiator is a concentration of
0.05~0.5mol/l；Be passed through carbon dioxide, the air in the reaction kettle is discharged, and make the Diacetone Acrylamide,
The total monomer concentration of acrylamide is 1~8mol/l, then fastens the exits and entrances valve of the reaction kettle, is heated；With temperature
Raising, the reacting kettle inner pressure constantly rises, when reaction temperature reaches 32~40 DEG C, by the pressure in the reaction kettle
（The pressure of carbon dioxide i.e. in kettle）Control is in 8MPa or more, 45MPa or less；At this point, start blender, the reaction time is 3~
20 hours, until reaction terminates.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, in the redox system
The persulfate is one kind in potassium peroxydisulfate, sodium peroxydisulfate or ammonium persulfate.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, in the redox system
The bisulfites is one kind of potassium bisulfite, sodium hydrogensulfite or ammonium bisulfite.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the Diacetone Acrylamide exist
Shared molar percentage is 0~70% in two kinds of monomers（Without 0%）.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the acrylamide is in two kinds of lists
Shared molar percentage 30~100% in body（Without 100%）.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the Diacetone Acrylamide,
The total monomer concentration of acrylamide is 2~6mol/l.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, persulfate in the initiator
Molar ratio with the initial content of bisulfites is 1:1, a concentration of 0.08~0.3mol/ of the initiator initial content
l。
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the pressure control in the reaction kettle
System is in 20~30MPa.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the reaction temperature control is 33
~38 DEG C.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer, the reaction time is 4~10
Hour.
The method of above-mentioned a kind of synthesis Diacetone Acrylamide and acrylamide copolymer is passed through cooling after reaction
Water makes the reaction kettle be cooled to room temperature；The air outlet valve for opening the reaction kettle is depressurized to normal pressure, takes out product, i.e., not aqueous
Diacetone Acrylamide and acrylamide copolymer.
The present invention by adopting the above-described technical solution, it using nontoxic and pollution-free medium supercritical carbon dioxide come generation
For organic solvent, the temperature and pressure of carbon dioxide is higher than its critical-temperature and critical pressure.Supercritical carbon dioxide is simultaneous at this time
The property for having liquids and gases, the pressure by changing supercritical carbon dioxide can change the dissolving of supercritical carbon dioxide
Property, thus the use instead of toxic, harmful, volatile and inflammable organic solvent is can be used to, avoid chemical industry organic solvent to ring
It is seriously polluted caused by border.Since carbon dioxide is current many by-products industrially generated, it can get from environment, use
Environment can be returned after chemical process, without any by-product, while own has that non-combustible, nontoxic, chemical stability is good,
It the advantages that cheap and easy to get, thus use it for synthesis Diacetone Acrylamide and sodium acrylate copolymer, can be to avoid having used
Malicious, harmful, volatile and inflammable organic solvent pollutes the environment, and realizes work that is environmentally protective, energy saving, economizing on resources
With.
Specific implementation mode
A kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer of embodiment 1, it includes the following steps：
By the acrylamide of a concentration of 2.3mol/l, the Diacetone Acrylamide of a concentration of 1.7mol/l and a concentration of 0.1
The initiator of mol/l（The mixture of ammonium persulfate and sodium hydrogensulfite, mixed molar ratio are 1:1）It is added separately to react
Kettle, sealing.Wherein, Diacetone Acrylamide molar percentage shared in two kinds of monomers is 42.5%, and acrylamide is at two kinds
Shared molar percentage 57.5% in monomer.
It is passed through carbon dioxide 25 minutes, the air in reaction kettle is discharged, makes Diacetone Acrylamide, acrylamide
Total monomer initial concentration is 4mol/l.
Then the exits and entrances valve of reaction kettle is fastened, is heated.When temperature rises to 30 DEG C, the high pressure of reaction kettle is opened
Pump, and supplement a certain amount of carbon dioxide.With the raising of temperature, the pressure in reaction kettle is made constantly to increase, when temperature reaches
When 35 DEG C of required reaction temperature, the pressure in reaction kettle is controlled, so that it is maintained required pressure 20MPa, starts stir at this time
Mix device, the time that record reaction starts.After reacting 6 hours, reaction kettle is made to be cooled to room temperature.
The air outlet valve for opening reaction kettle, is depressurized to normal pressure.Products therefrom is a large amount of white products, i.e., not aqueous diacetone
Acrylamide and acrylamide copolymer.
A kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer of embodiment 2, it includes the following steps：
By the acrylamide of a concentration of 1.9mol/l, the Diacetone Acrylamide of a concentration of 3.1mol/l and a concentration of 0.2
The initiator of mol/l（The mixture of sodium peroxydisulfate and potassium bisulfite, mixed molar ratio are 1:1）It is added separately to react
Kettle, sealing.Wherein, Diacetone Acrylamide molar percentage shared in two kinds of monomers is 62%, and acrylamide is in two kinds of lists
Shared molar percentage 38% in body.
It is passed through carbon dioxide 25 minutes, the air in reaction kettle is discharged, makes Diacetone Acrylamide, acrylamide
Total monomer initial concentration is 5mol/l.
Then the exits and entrances valve of reaction kettle is fastened, is heated.When temperature rises to 30 DEG C, the high pressure of reaction kettle is opened
Pump, and supplement a certain amount of carbon dioxide.With the raising of temperature, the pressure in reaction kettle is made constantly to increase, when temperature reaches
When 33 DEG C of required reaction temperature, the pressure in reaction kettle is controlled, so that it is maintained required pressure 25MPa, starts stir at this time
Mix device, the time that record reaction starts.After reacting 7 hours, reaction kettle is made to be cooled to room temperature.
The air outlet valve for opening reaction kettle, is depressurized to normal pressure.Products therefrom is a large amount of white products, i.e., not aqueous diacetone
Acrylamide and acrylamide copolymer.
A kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer of embodiment 3, it includes the following steps：
By the acrylamide of a concentration of 1.1mol/l, the Diacetone Acrylamide of a concentration of 2.2mol/l and a concentration of
The initiator of 0.25mol/l（The mixture of potassium peroxydisulfate and ammonium bisulfite, mixed molar ratio are 1:1）It is added separately to
Reaction kettle, sealing.Wherein, Diacetone Acrylamide molar percentage shared in two kinds of monomers is 66.67%, acrylamide
The shared molar percentage 33.33% in two kinds of monomers.
It is passed through carbon dioxide 25 minutes, the air in reaction kettle is discharged, makes Diacetone Acrylamide, acrylamide
Total monomer initial concentration is 3.3mol/l.
Then the exits and entrances valve of reaction kettle is fastened, is heated.When temperature rises to 30 DEG C, the high pressure of reaction kettle is opened
Pump, and supplement a certain amount of carbon dioxide.With the raising of temperature, the pressure in reaction kettle is made constantly to increase, when temperature reaches
When 36 DEG C of required reaction temperature, the pressure in reaction kettle is controlled, so that it is maintained required pressure 29MPa, starts stir at this time
Mix device, the time that record reaction starts.After reacting 3 hours, reaction kettle is made to be cooled to room temperature.
The air outlet valve for opening reaction kettle, is depressurized to normal pressure.Products therefrom is a large amount of white products, i.e., not aqueous diacetone
Acrylamide and acrylamide copolymer.
In the method for the present invention, initiator is the wherein mistake made of two kinds of material mixings of persulfate and bisulfites
Sulfate plays oxidation, and bisulfites plays reduction, therefore forms redox system.
Claims (10)
1. a kind of method of synthesis Diacetone Acrylamide and acrylamide copolymer, which is characterized in that it is with carbon dioxide
Medium, using persulfate and Bisulphite redox system as initiator, carbon dioxide critical-temperature and pressure with
On, precipitation polymerization is carried out to Diacetone Acrylamide and acrylamide comonomer, obtains Diacetone Acrylamide and acryloyl
Amine copolymer object.
2. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as described in claim 1, feature exist
In it includes the following steps：Reaction kettle is added in Diacetone Acrylamide, acrylamide monomer and initiator, sealing is described to draw
Send out a concentration of 0.05~0.5mol/l of initial content of agent；It is passed through carbon dioxide, the air in the reaction kettle is discharged, and is made
The Diacetone Acrylamide, the total monomer concentration of acrylamide are 1~8mol/l, then fasten the inlet and outlet of the reaction kettle
Valve, heating；With the raising of temperature, the reacting kettle inner pressure constantly rises, will when reaction temperature reaches 32~40 DEG C
Pressure in the reaction kettle（The pressure of carbon dioxide i.e. in kettle）Control is in 8MPa or more, 45MPa or less；It is stirred at this point, starting
Device is mixed, the reaction time is 3~20 hours, until reaction terminates.
3. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 1 or 2, feature
It is, the persulfate in the redox system is one kind in potassium peroxydisulfate, sodium peroxydisulfate or ammonium persulfate；Institute
State one kind that the bisulfites in redox system is potassium bisulfite, sodium hydrogensulfite or ammonium bisulfite.
4. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In Diacetone Acrylamide molar percentage shared in two kinds of monomers is 0~70%；The acrylamide is at two kinds
Shared molar percentage 30~100% in monomer.
5. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In the Diacetone Acrylamide, the total monomer concentration of acrylamide are 2~6mol/l.
6. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In the molar ratio of the initial content of persulfate and bisulfites is 1 in the initiator:1, the initiator is initially used
A concentration of 0.08~0.3mol/l of amount.
7. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In the pressure in the reaction kettle is controlled in 20~30MPa.
8. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In the reaction temperature control is at 33~38 DEG C.
9. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 2, feature exist
In the reaction time is 4~10 hours.
10. the method for a kind of synthesis Diacetone Acrylamide and acrylamide copolymer as claimed in claim 1 or 2, special
Sign is, after reaction, is passed through cooling water, and the reaction kettle is made to be cooled to room temperature；The air outlet valve of the reaction kettle is opened, is dropped
It is depressed into normal pressure, takes out product, i.e., not aqueous Diacetone Acrylamide and acrylamide copolymer.
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| CN201810046622.6A CN108314750B (en) | 2018-01-18 | 2018-01-18 | Method for synthesizing diacetone acrylamide and acrylamide copolymer |
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| CN201810046622.6A CN108314750B (en) | 2018-01-18 | 2018-01-18 | Method for synthesizing diacetone acrylamide and acrylamide copolymer |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019043A (en) * | 2019-12-12 | 2020-04-17 | 贵州师范学院 | CO (carbon monoxide)2/N2Switch type temperature-sensitive polymer and preparation method thereof |
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| US20150345079A1 (en) * | 2012-11-22 | 2015-12-03 | Kemira Oyj | Polymer and its preparation and use |
| CN105585650A (en) * | 2014-10-21 | 2016-05-18 | 中国石油化工股份有限公司 | Preparation method of high-molecular-weight polyacrylamide |
| CN105646774A (en) * | 2015-12-29 | 2016-06-08 | 四川光亚聚合物化工有限公司 | Hydrophobic associated polymer and preparation method thereof |
-
2018
- 2018-01-18 CN CN201810046622.6A patent/CN108314750B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150345079A1 (en) * | 2012-11-22 | 2015-12-03 | Kemira Oyj | Polymer and its preparation and use |
| CN105585650A (en) * | 2014-10-21 | 2016-05-18 | 中国石油化工股份有限公司 | Preparation method of high-molecular-weight polyacrylamide |
| CN105646774A (en) * | 2015-12-29 | 2016-06-08 | 四川光亚聚合物化工有限公司 | Hydrophobic associated polymer and preparation method thereof |
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| 张玉平 等: ""AM/DAAM二元共聚物的合成与表征"", 《化学世界》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019043A (en) * | 2019-12-12 | 2020-04-17 | 贵州师范学院 | CO (carbon monoxide)2/N2Switch type temperature-sensitive polymer and preparation method thereof |
| CN111019043B (en) * | 2019-12-12 | 2021-07-13 | 贵州师范学院 | CO (carbon monoxide)2/N2Switch type temperature-sensitive polymer and preparation method thereof |
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Effective date of registration: 20230228 Address after: 351200 Fengting Industrial Park, Xianyou County, Putian City, Fujian Province Patentee after: Fujian Zhiye Industrial Co.,Ltd. Address before: No.1 building and No.2 building, No.333, Haiyang 1st Road, Lingang New District, China (Shanghai) pilot Free Trade Zone, Pudong New Area, Shanghai, 200120 Patentee before: Shanghai Zhicha Technology Co.,Ltd. Effective date of registration: 20230228 Address after: No.1 building and No.2 building, No.333, Haiyang 1st Road, Lingang New District, China (Shanghai) pilot Free Trade Zone, Pudong New Area, Shanghai, 200120 Patentee after: Shanghai Zhicha Technology Co.,Ltd. Address before: Building 2, photovoltaic technology park, 1288 Kanghe Road, Xiuzhou District, Jiaxing City, Zhejiang Province, 314001 Patentee before: JIAXING University |