CN108440750A - A kind of preparation method of high-purity polyethylene glycol aldehyde derivative - Google Patents
A kind of preparation method of high-purity polyethylene glycol aldehyde derivative Download PDFInfo
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- CN108440750A CN108440750A CN201810321911.2A CN201810321911A CN108440750A CN 108440750 A CN108440750 A CN 108440750A CN 201810321911 A CN201810321911 A CN 201810321911A CN 108440750 A CN108440750 A CN 108440750A
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- polyethylene glycol
- aldehyde derivative
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic compounds containing oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
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- General Chemical & Material Sciences (AREA)
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- External Artificial Organs (AREA)
- Medicinal Preparation (AREA)
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Abstract
The invention discloses a kind of preparation methods of high-purity polyethylene glycol aldehyde derivative, specifically include following steps：Step 1：Enough catalyst are added into polyethylene glycol；Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, and to which the mixture of polyethylene glycol aldehyde derivative and water be made, reaction principle is：2‑CH2OH+O2The CHO+2H of==22O, reaction condition are heating and catalyst；Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and carries out dialysis treatment.By the present invention in that the terminal hydroxy group obtained in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which high-purity polyethylene glycol aldehyde derivative be made, have preparation difficulty low, it is conveniently operated, manufacturing cost is low, the advantages of being convenient for promoting and preparation efficiency is high, be convenient for industrialized production.
Description
Technical field
The present invention relates to polyethylene glycol aldehyde derivative technical field, more particularly to a kind of high-purity polyethylene glycol aldehydes spreads out
The preparation method of biology.
Background technology
Polyethylene glycol (PEG) is a kind of polyether high molecular compound that purposes is extremely wide, it can be applied to medicine, defends
The various fields such as life, food, chemical industry.PEG can be dissolved in water and many solvents, and the polymer has excellent biofacies
Capacitive can be dissolved in tissue fluid in vivo, can rapidly be excluded external and not produced any toxic side effects by body, it more difficult to
It is that when PEG and the coupling of other molecules, its many advantageous properties can be also transferred in conjugate therewith.Therefore, it is being cured
Application on receives extensive attention.Polyethylene glycol can be used as excipient substance to improve the various of drug in pharmaceutical industries
Performance, such as dispersibility, film forming, lubricity, slow release.In the synthesis and modification of novel biomaterial, polyethylene glycol is made
For a part for material, it will assign material new characteristic and function, as hydrophily, flexibility, anticoagulant property and anti-macrophage gulp down
Biting property etc..In the application of polyethylene glycol, end group plays conclusive effect, and the polyethylene glycol of different end group has different use
On the way, the polyethylene glycol polymer end of the chain is not limited solely to band terminal hydroxy group, other stronger functionalization of reactivity in practical applications
Group, such as p-methyl benzenesulfonic acid ester group, amino, carboxyl, aldehyde radical can also be introduced in the both ends of polyglycol chain.These functionalization
The introducing of group expands the application range of polyethylene glycol, makes it in organic synthesis, Peptide systhesis, Polymer Synthesizing and drug
Sustained-release and controlled release, targeting dispenser etc. are many-sided to all have wide application prospect, and the report in relation to synthesizing and applying increasingly increases.
Polyethylene glycol aldehyde derivative belongs to one kind in a variety of polyethyleneglycol derivatives, existing to be used to prepare high-purity
There is also some disadvantages for the preparation method of polyethylene glycol aldehyde derivative, if convert aldehyde groups rate is low, prepare difficulty and manufacturing cost
The problems such as high and preparation efficiency is low.
Therefore, inventing a kind of preparation method of high-purity polyethylene glycol aldehyde derivative, have very much must to solve the above problems
It wants.
Invention content
The purpose of the present invention is to provide a kind of preparation methods of high-purity polyethylene glycol aldehyde derivative, are gathered by making
Terminal hydroxy group in ethylene glycol reacts with oxygen to form aldehyde radical and water, and the mixture of polyethylene glycol aldehyde derivative and water is made
And dialysis frozen dried is carried out, to which high-purity polyethylene glycol aldehyde derivative be made, has preparation difficulty low, is conveniently operated,
Manufacturing cost is low, the advantages of being convenient for promoting and preparation efficiency is high, be convenient for industrialized production, to solve to propose in above-mentioned background technology
The problem of.
To achieve the above object, the present invention provides the following technical solutions：A kind of high-purity polyethylene glycol aldehyde derivative
Preparation method specifically includes following steps：
Step 1：Enough catalyst are added into polyethylene glycol；
Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；
Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which polyethylene glycol be made
The mixture of aldehyde derivative and water, reaction principle are：
2-CH2OH+O2==2-CHO+2H2O, reaction condition are heating and catalyst；
Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and is carried out
Dialysis treatment；
Step 5：Then the mixture of the polyethylene glycol aldehyde derivative after dialysing in step 4 and water is cooled to 0-
5℃；
Step 6：Then freeze drying equipment is used to carry out frozen dried, freeze-drying to mixture after cooling in step 5
Temperature setting is -45--35 DEG C, the water sublimed in mixture；
Step 7：Re-dry processing is carried out to the mixture by step 6 processing, drying temperature is set as 30-35 DEG C,
Polyethylene glycol aldehyde derivative is made；
Step 8 carries out infrared detection to polyethylene glycol aldehyde derivative obtained in step 7, and to detection data into
Row record.
Preferably, the catalyst in the step 1 is set as copper.
Preferably, heating temperature is set as 80-100 DEG C in the step 3.
Preferably, freeze drying equipment is set as freeze drying box in the step 6.
The technique effect and advantage of the present invention：
1：By the present invention in that the terminal hydroxy group obtained in polyethylene glycol reacts with oxygen to form aldehyde radical and water, poly- second is made
The mixture of glycol aldehyde derivative and water simultaneously carries out dialysis frozen dried, derives to which high-purity polyethylene glycol aldehydes be made
Object has preparation difficulty low, is conveniently operated, and manufacturing cost is low, high with preparation efficiency convenient for promoting, and is convenient for the excellent of industrialized production
Point；
2：By carrying out infrared detection to polyethylene glycol aldehyde derivative obtained, and detection data is recorded, from
And the aldehyde group content in polyethylene glycol aldehyde derivative obtained is quickly judged, so that operator can be with fast direct
That sees recognizes the convert aldehyde groups rate of current polyethylene glycol aldehyde derivative obtained so that operator can be more intuitive
It solves and prepares result.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical solution in the embodiment of the present invention is clearly and completely retouched
It states, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on the present invention
In embodiment, every other implementation obtained by those of ordinary skill in the art without making creative efforts
Example, shall fall within the protection scope of the present invention.
Embodiment 1：
A kind of preparation method of high-purity polyethylene glycol aldehyde derivative, specifically includes following steps：
Step 1：Enough catalyst are added into polyethylene glycol, the catalyst is set as copper；
Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；
Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which polyethylene glycol be made
The mixture of aldehyde derivative and water, reaction principle are：
2-CH2OH+O2==2-CHO+2H2O, reaction condition are that heating and catalyst, heating temperature are set as 80 DEG C；
Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and is carried out
Dialysis treatment；
Step 5：Then the mixture of the polyethylene glycol aldehyde derivative after dialysing in step 4 and water is cooled to 0
℃；
Step 6：Then freeze drying box is used to carry out frozen dried to mixture after cooling in step 5, freeze temperature is set
- 45 DEG C are set to, the water sublimed in mixture；
Step 7：Re-dry processing is carried out to the mixture by step 6 processing, drying temperature is set as 30 DEG C, is made
Polyethylene glycol aldehyde derivative；
Step 8 carries out infrared detection to polyethylene glycol aldehyde derivative obtained in step 7, and to detection data into
Row record.
Convert aldehyde groups rate is about 93% in the present embodiment, and preparation difficulty is general with preparation efficiency, and manufacturing cost is relatively low.
Embodiment 2：
A kind of preparation method of high-purity polyethylene glycol aldehyde derivative, specifically includes following steps：
Step 1：Enough catalyst are added into polyethylene glycol, the catalyst is set as copper；
Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；
Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which polyethylene glycol be made
The mixture of aldehyde derivative and water, reaction principle are：
2-CH2OH+O2==2-CHO+2H2O, reaction condition are that heating and catalyst, heating temperature are set as 90 DEG C；
Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and is carried out
Dialysis treatment；
Step 5：Then the mixture of the polyethylene glycol aldehyde derivative after dialysing in step 4 and water is cooled to 3
℃；
Step 6：Then freeze drying box is used to carry out frozen dried to mixture after cooling in step 5, freeze temperature is set
- 40 DEG C are set to, the water sublimed in mixture；
Step 7：Re-dry processing is carried out to the mixture by step 6 processing, drying temperature is set as 33 DEG C, is made
Polyethylene glycol aldehyde derivative；
Step 8 carries out infrared detection to polyethylene glycol aldehyde derivative obtained in step 7, and to detection data into
Row record.
Convert aldehyde groups rate is about 97% in the present embodiment, prepare difficulty it is relatively low, preparation efficiency is higher, manufacturing cost compared with
It is low.
Embodiment 3：
A kind of preparation method of high-purity polyethylene glycol aldehyde derivative, specifically includes following steps：
Step 1：Enough catalyst are added into polyethylene glycol, the catalyst is set as copper；
Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；
Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which polyethylene glycol be made
The mixture of aldehyde derivative and water, reaction principle are：
2-CH2OH+O2==2-CHO+2H2O, reaction condition are that heating and catalyst, heating temperature are set as 100 DEG C；
Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and is carried out
Dialysis treatment；
Step 5：Then the mixture of the polyethylene glycol aldehyde derivative after dialysing in step 4 and water is cooled to 5
℃；
Step 6：Then freeze drying box is used to carry out frozen dried to mixture after cooling in step 5, freeze temperature is set
- 35 DEG C are set to, the water sublimed in mixture；
Step 7：Re-dry processing is carried out to the mixture by step 6 processing, drying temperature is set as 35 DEG C, is made
Polyethylene glycol aldehyde derivative；
Step 8 carries out infrared detection to polyethylene glycol aldehyde derivative obtained in step 7, and to detection data into
Row record.
Convert aldehyde groups rate is about 92% in the present embodiment, prepare difficulty it is general, preparation efficiency is higher, manufacturing cost compared with
It is low.
By above-described embodiment 1-3 it is found that the polyethylene glycol aldehyde derivative aldehyde radical that each item data in embodiment 2 is prepared
Conversion ratio highest, that is, purity highest, while having preparation difficulty low, it is conveniently operated, manufacturing cost is low, convenient for promoting and preparing effect
Rate is high, the advantages of being convenient for industrialized production, while by carrying out infrared detection to polyethylene glycol aldehyde derivative obtained, and right
Detection data is recorded, to quickly be judged the aldehyde group content in polyethylene glycol aldehyde derivative obtained, to
So that operator can be with the convert aldehyde groups rate for recognizing current polyethylene glycol aldehyde derivative obtained of quicklook so that behaviour
Author can be with more intuitive understanding to preparation result.
Finally it should be noted that：The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention,
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still may be used
With technical scheme described in the above embodiments is modified or equivalent replacement of some of the technical features,
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in the present invention's
Within protection domain.
Claims (4)
1. a kind of preparation method of high-purity polyethylene glycol aldehyde derivative, which is characterized in that specifically include following steps：
Step 1：Enough catalyst are added into polyethylene glycol；
Step 2：Polyethylene glycol heat and is passed through sufficient amount of oxygen during heating；
Step 3：Terminal hydroxy group in polyethylene glycol reacts with oxygen to form aldehyde radical and water, to which polyethylene glycol aldehydes be made
The mixture of derivative and water, reaction principle are：
2-CH2OH+O2==2-CHO+2H2O, reaction condition are heating and catalyst；
Step 4：Then the mixture of polyethylene glycol aldehyde derivative and water in step 3 is fitted into bag filter and is dialysed
Processing；
Step 5：Then the mixture of the polyethylene glycol aldehyde derivative after dialysing in step 4 and water is cooled to 0-5 DEG C；
Step 6：Then freeze drying equipment is used to carry out frozen dried, freeze temperature to mixture after cooling in step 5
- 45--35 DEG C are set as, the water sublimed in mixture；
Step 7：Re-dry processing is carried out to the mixture by step 6 processing, drying temperature is set as 30-35 DEG C, is made
Polyethylene glycol aldehyde derivative；
Step 8 carries out infrared detection to polyethylene glycol aldehyde derivative obtained in step 7, and remembers to detection data
Record.
2. a kind of preparation method of high-purity polyethylene glycol aldehyde derivative according to claim 1, it is characterised in that：Institute
The catalyst stated in step 1 is set as copper.
3. a kind of preparation method of high-purity polyethylene glycol aldehyde derivative according to claim 1, it is characterised in that：Institute
It states heating temperature in step 3 and is set as 80-100 DEG C.
4. a kind of preparation method of high-purity polyethylene glycol aldehyde derivative according to claim 1, it is characterised in that：Institute
It states freeze drying equipment in step 6 and is set as freeze drying box.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113308900A (en) * | 2021-06-08 | 2021-08-27 | 安徽弋尚纺织科技有限公司 | Production process of crease-resistant and wear-resistant suit fabric |
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|---|---|---|---|---|
| US6465694B1 (en) * | 1998-10-26 | 2002-10-15 | University Of Utah Research Foundation | Method for preparation of polyethylene glycol aldehyde derivatives |
| CN1970086A (en) * | 2006-11-30 | 2007-05-30 | 复旦大学 | Monomodified PEGylated insulin and its preparation method |
| CN101357986A (en) * | 2007-06-13 | 2009-02-04 | 康达医药科技有限公司 | Polyethylene glycol functional derivative and preparation method thereof |
| CN102037056A (en) * | 2008-05-20 | 2011-04-27 | 韩国埃迪碧化学株式会社 | A method for preparing high-purity polyethyleneglycol aldehyde derivatives |
| CN104109235A (en) * | 2014-05-30 | 2014-10-22 | 厦门赛诺邦格生物科技有限公司 | Mono-functionalized polyethylene glycol with nitrogen atom branched center and its preparation method and biologically-relevant matter |
-
2018
- 2018-04-11 CN CN201810321911.2A patent/CN108440750A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6465694B1 (en) * | 1998-10-26 | 2002-10-15 | University Of Utah Research Foundation | Method for preparation of polyethylene glycol aldehyde derivatives |
| CN1970086A (en) * | 2006-11-30 | 2007-05-30 | 复旦大学 | Monomodified PEGylated insulin and its preparation method |
| CN101357986A (en) * | 2007-06-13 | 2009-02-04 | 康达医药科技有限公司 | Polyethylene glycol functional derivative and preparation method thereof |
| CN102037056A (en) * | 2008-05-20 | 2011-04-27 | 韩国埃迪碧化学株式会社 | A method for preparing high-purity polyethyleneglycol aldehyde derivatives |
| CN104109235A (en) * | 2014-05-30 | 2014-10-22 | 厦门赛诺邦格生物科技有限公司 | Mono-functionalized polyethylene glycol with nitrogen atom branched center and its preparation method and biologically-relevant matter |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113308900A (en) * | 2021-06-08 | 2021-08-27 | 安徽弋尚纺织科技有限公司 | Production process of crease-resistant and wear-resistant suit fabric |
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Application publication date: 20180824 |