CN108440697A - A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate - Google Patents
A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate Download PDFInfo
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Abstract
The invention discloses a kind of synthetic methods of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, include the following steps：Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride；Step 2: being caused with initiator, the dissolving of allylamine hydrochloride monomer itself is polymerize in a solvent；Then solution is slowly dropped in methanol and carries out crystallization, filter to obtain allylamine salt acid polymer；Step 3, allylamine salt acid polymer alkalize to obtain allyl amine polymer；Cithrol, nano aluminium oxide and epoxychloropropane, synthetic hydrochloric acid sevelamer is added in step 4；Step 5, sevelamer hydrochloride first neutralizes to obtain the sevelamer of free state with aqueous slkali, then is reacted with arbon dioxide solution, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；Step 6: preparing 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate piece.The preparation method of the 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate of invention, stable reaction, period are short, and the quality of obtained 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is good.
Description
Technical field
The present invention relates to biomedicine field, the synthetic method of specifically a kind of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate.
Background technology
Aliphatic polyamines resin cation mainly include sevelamer hydrochloride, sevelamer, 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and other
Any possible salt, colesevelam hydrocholoride etc..These products have been applied in disease treatment, are mainly used for treating high phosphorus blood
Disease, diabetes, gout, reduces uric acid at hyperlipidemia, even adsorbs relevant ions.The application principle of such aliphatic polyamines is real
Matter is the suction-operated of resin.The suction-operated of resin has been widely used in industry, agricultural or environmental protection industry (epi).
2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate（Sevelamer carbonate）, chemical name：2- propylene -1- amine and epoxychloropropane it is poly-
Close object carbonate.2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is as a kind of aliphatic poly amine polymer, by prior art discloses preparation methods.
Preparation method is disclosed in the U.S. Patent application of Publication No. US2010/013742, it is specific as follows：By polyallylamine salt
The polymer of hydrochlorate and carbonic acid or heavy carbonic ionic reaction, to form the carbonate that N- is alkylated crosslinked polyallylamine chlorine.It will
The carbonate of obtained polyallylamine reacts under sodium hydroxide effect with crosslinking agent, obtains Sevelamer Carbonate.However it should
Impurity content in the 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate that method is prepared is high, affects the quality of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate.Therefore, of the invention
A kind of synthetic method of novel 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is provided.
Invention content
The purpose of the present invention is to provide a kind of synthetic methods of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, to solve to carry in above-mentioned background technology
The problem of going out.
To achieve the above object, the present invention provides the following technical solutions：
A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, includes the following steps：
Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride, wherein allylamine and concentrated hydrochloric acid
Weight ratio is（2-5）:（10-15）, reaction temperature is 48-55 DEG C, and the reaction time is 1-2 hours；
Step 2: using peroxidating phenyl-diformyl as initiator cause, by allylamine hydrochloride monomer dissolving in a solvent itself
It polymerize, reaction temperature is 92-98 DEG C, and the reaction time is 10-15 hours；Peroxidating phenyl-diformyl and allylamine hydrochloride list
The weight ratio of body is（0.01-0.1）:（50-150）；Cool down after reaction, solution is slowly dropped in methanol and is analysed
Crystalline substance, rate of addition are 30-50 drops/min, continue stirring 1-3 hours after being added dropwise to complete, allylamine salt acid polymer is obtained by filtration；
Step 3, allylamine salt acid polymer react alkalization with the organic alkali solution that pH is 8-12 and obtain allyl amine polymer；
Cithrol, nano aluminium oxide and epoxychloropropane, the allyl amine polymer, poly- second is added in step 4
The weight ratio of diol fatty acid ester, epoxychloropropane and nano aluminium oxide is 1:（0.5-1）:（1-1.3）:（0.1-0.3）, allyl
Amine polymer and epichlorohydrin reaction synthetic hydrochloric acid sevelamer；
Step 5, sevelamer hydrochloride first neutralize to obtain the sevelamer of free state with aqueous slkali, then with arbon dioxide solution
Reaction, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；
Step 6: 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is uniformly mixed with hydroxypropyl methyl cellulose；In 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and hydroxypropyl first
Sodium bicarbonate solution is added in the mixture of base cellulose；By 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, hydroxypropyl methyl cellulose and sodium bicarbonate
The granulating mixture of solution；Powder is sieved；Riboflavin and sodium alginate are added in powder after sizing, and mixes equal
It is even；Tabletting；Coating；To obtain the final product.
As a further solution of the present invention：Organic alkali solution uses sodium methoxide, potassium tert-butoxide or lithium diisopropyl amido.
As a further solution of the present invention：Solvent uses acetonitrile, ethyl alcohol or isopropanol.
As a further solution of the present invention：The weight ratio of allylamine and concentrated hydrochloric acid is 3 in step 1:12, reaction temperature
It it is 50 DEG C, the reaction time is 1.6 hours.
As a further solution of the present invention：Reaction temperature is 95 DEG C in step 2, and the reaction time is 12 hours.
As a further solution of the present invention：The weight of peroxidating phenyl-diformyl and allylamine hydrochloride monomer in step 2
Than being 0.03:120.
As a further solution of the present invention：Rate of addition is 42 drops/min in step 2, continues stirring 2 after being added dropwise to complete
Hour.
As a further solution of the present invention：Allylamine salt acid polymer and pH are anti-for 10 organic alkali solution in step 3
It should alkalize to obtain allyl amine polymer.
As a further solution of the present invention：Allyl amine polymer, cithrol, epoxy chloropropionate in step 4
The weight ratio of alkane and nano aluminium oxide is 1:0.6:1.2:0.2.
Compared with prior art, the beneficial effects of the invention are as follows：
The preparation method of the 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate of invention, stable reaction, period are short, and the quality of obtained 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is good,
Titratable amine content 11.3-14.1mmol/g, swelling index 5-11, soluble oligomer<0.1%, carbonate content 15-
20%；And it is the high income of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, smaller to the harm of environment, it is suitable for industrialized production.
Specific implementation mode
The technical solution of this patent is described in more detail With reference to embodiment.
Embodiment 1
A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, includes the following steps：
Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride, wherein allylamine and concentrated hydrochloric acid
Weight ratio is 2:10, reaction temperature is 48 DEG C, and the reaction time is 1 hour；
Step 2: using peroxidating phenyl-diformyl as initiator cause, by allylamine hydrochloride monomer dissolving in a solvent itself
It polymerize, reaction temperature is 92 DEG C, and the reaction time is 10 hours；Solvent uses acetonitrile；Peroxidating phenyl-diformyl and allylamine
The weight ratio of hydrochloric acid salt monomer is 0.01:50；Cool down after reaction, solution is slowly dropped in methanol and carries out crystallization, drips
Acceleration is 30 drops/min, continues stirring 1 hour after being added dropwise to complete, allylamine salt acid polymer is obtained by filtration；
Step 3, allylamine salt acid polymer react alkalization with the pH organic alkali solutions for being 8 and obtain allyl amine polymer；Organic base
Solution uses sodium methoxide；Cithrol, nano aluminium oxide and epoxychloropropane, the allylamine is added in step 4
Polymer, cithrol, epoxychloropropane and nano aluminium oxide weight ratio be 1:0.5:1:0.1, allylamine is poly-
Close object and epichlorohydrin reaction synthetic hydrochloric acid sevelamer；
Step 5, sevelamer hydrochloride first neutralize to obtain the sevelamer of free state with aqueous slkali, then with arbon dioxide solution
Reaction, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；
Step 6: 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is uniformly mixed with hydroxypropyl methyl cellulose；In 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and hydroxypropyl first
Sodium bicarbonate solution is added in the mixture of base cellulose；By 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, hydroxypropyl methyl cellulose and sodium bicarbonate
The granulating mixture of solution；Powder is sieved；Riboflavin and sodium alginate are added in powder after sizing, and mixes equal
It is even；Tabletting；Coating；To obtain the final product.
Embodiment 2
A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, includes the following steps：
Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride, wherein allylamine and concentrated hydrochloric acid
Weight ratio is 5:15, reaction temperature is 55 DEG C, and the reaction time is 2 hours；
Step 2: using peroxidating phenyl-diformyl as initiator cause, by allylamine hydrochloride monomer dissolving in a solvent itself
It polymerize, reaction temperature is 98 DEG C, and the reaction time is 15 hours；Solvent uses ethyl alcohol；Peroxidating phenyl-diformyl and allylamine
The weight ratio of hydrochloric acid salt monomer is 0.1:150；Cool down after reaction, solution is slowly dropped in methanol and carries out crystallization, drips
Acceleration is 50 drops/min, continues stirring 3 hours after being added dropwise to complete, allylamine salt acid polymer is obtained by filtration；
Step 3, allylamine salt acid polymer react alkalization with the pH organic alkali solutions for being 12 and obtain allyl amine polymer；It is organic
Aqueous slkali uses potassium tert-butoxide；Cithrol, nano aluminium oxide and epoxychloropropane, the alkene is added in step 4
Propylamine polymer, cithrol, epoxychloropropane and nano aluminium oxide weight ratio be 1:1:1.3:0.3, allyl
Amine polymer and epichlorohydrin reaction synthetic hydrochloric acid sevelamer；
Step 5, sevelamer hydrochloride first neutralize to obtain the sevelamer of free state with aqueous slkali, then with arbon dioxide solution
Reaction, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；
Step 6: 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is uniformly mixed with hydroxypropyl methyl cellulose；In 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and hydroxypropyl first
Sodium bicarbonate solution is added in the mixture of base cellulose；By 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, hydroxypropyl methyl cellulose and sodium bicarbonate
The granulating mixture of solution；Powder is sieved；Riboflavin and sodium alginate are added in powder after sizing, and mixes equal
It is even；Tabletting；Coating；To obtain the final product.
Embodiment 3
A kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, includes the following steps：
Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride, wherein allylamine and concentrated hydrochloric acid
Weight ratio is 3:12, reaction temperature is 50 DEG C, and the reaction time is 1.6 hours；
Step 2: using peroxidating phenyl-diformyl as initiator cause, by allylamine hydrochloride monomer dissolving in a solvent itself
It polymerize, reaction temperature is 95 DEG C, and the reaction time is 12 hours；The weight of peroxidating phenyl-diformyl and allylamine hydrochloride monomer
Amount is than being 0.03:120；Solvent uses isopropanol；Cool down after reaction, solution be slowly dropped in methanol and carries out crystallization,
Rate of addition is 42 drops/min, continues stirring 2 hours after being added dropwise to complete, allylamine salt acid polymer is obtained by filtration；
Step 3, allylamine salt acid polymer react alkalization with the pH organic alkali solutions for being 10 and obtain allyl amine polymer；It is organic
Aqueous slkali uses lithium diisopropyl amido；
Cithrol, nano aluminium oxide and epoxychloropropane, the allyl amine polymer, poly- second is added in step 4
The weight ratio of diol fatty acid ester, epoxychloropropane and nano aluminium oxide is 1:0.6:1.2:0.2, allyl amine polymer and epoxy
Chloropropane reacts synthetic hydrochloric acid sevelamer；
Step 5, sevelamer hydrochloride first neutralize to obtain the sevelamer of free state with aqueous slkali, then with arbon dioxide solution
Reaction, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；
Step 6: 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is uniformly mixed with hydroxypropyl methyl cellulose；In 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and hydroxypropyl first
Sodium bicarbonate solution is added in the mixture of base cellulose；By 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, hydroxypropyl methyl cellulose and sodium bicarbonate
The granulating mixture of solution；Powder is sieved；Riboflavin and sodium alginate are added in powder after sizing, and mixes equal
It is even；Tabletting；Coating；To obtain the final product.
The better embodiment of this patent is explained in detail above, but this patent is not limited to above-mentioned embodiment party
Formula, one skilled in the relevant art within the scope of knowledge, can also be under the premise of not departing from this patent objective
Various changes can be made.
Claims (9)
1. a kind of synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, which is characterized in that include the following steps：
Step 1: allylamine and concentrated hydrochloric acid reaction acid chemical conversion salt are obtained allylamine hydrochloride, wherein allylamine and concentrated hydrochloric acid
Weight ratio is（2-5）:（10-15）, reaction temperature is 48-55 DEG C, and the reaction time is 1-2 hours；
Step 2: using peroxidating phenyl-diformyl as initiator cause, by allylamine hydrochloride monomer dissolving in a solvent itself
It polymerize, reaction temperature is 92-98 DEG C, and the reaction time is 10-15 hours；Peroxidating phenyl-diformyl and allylamine hydrochloride list
The weight ratio of body is（0.01-0.1）:（50-150）；Cool down after reaction, solution is slowly dropped in methanol and is analysed
Crystalline substance, rate of addition are 30-50 drops/min, continue stirring 1-3 hours after being added dropwise to complete, allylamine salt acid polymer is obtained by filtration；
Step 3, allylamine salt acid polymer react alkalization with the organic alkali solution that pH is 8-12 and obtain allyl amine polymer；
Cithrol, nano aluminium oxide and epoxychloropropane, the allyl amine polymer, poly- second is added in step 4
The weight ratio of diol fatty acid ester, epoxychloropropane and nano aluminium oxide is 1:（0.5-1）:（1-1.3）:（0.1-0.3）, allyl
Amine polymer and epichlorohydrin reaction synthetic hydrochloric acid sevelamer；
Step 5, sevelamer hydrochloride first neutralize to obtain the sevelamer of free state with aqueous slkali, then with arbon dioxide solution
Reaction, obtains 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate；
Step 6: 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate is uniformly mixed with hydroxypropyl methyl cellulose；In 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate and hydroxypropyl first
Sodium bicarbonate solution is added in the mixture of base cellulose；By 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate, hydroxypropyl methyl cellulose and sodium bicarbonate
The granulating mixture of solution；Powder is sieved；Riboflavin and sodium alginate are added in powder after sizing, and mixes equal
It is even；Tabletting；Coating；To obtain the final product.
2. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that organic alkali solution uses methanol
Sodium, potassium tert-butoxide or lithium diisopropyl amido.
3. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that solvent is using acetonitrile, ethyl alcohol
Or isopropanol.
4. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that allylamine and dense in step 1
The weight ratio of hydrochloric acid is 3:12, reaction temperature is 50 DEG C, and the reaction time is 1.6 hours.
5. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that reaction temperature is in step 2
95 DEG C, the reaction time is 12 hours.
6. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that step 2 benzoyl peroxide diformazan
The weight ratio of acyl and allylamine hydrochloride monomer is 0.03:120.
7. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that step 2 rate of addition is 42
Drop/min continues stirring 2 hours after being added dropwise to complete.
8. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that allylamine hydrochloric acid in step 3
Polymer reacts alkalization with the pH organic alkali solutions for being 10 and obtains allyl amine polymer.
9. the synthetic method of 2-Propen-1-amine polymer with(chloromethyl)oxirane carbonate according to claim 1, which is characterized in that allylamine polymerize in step 4
Object, cithrol, epoxychloropropane and nano aluminium oxide weight ratio be 1:0.6:1.2:0.2.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004352A (en) * | 2019-08-26 | 2020-04-14 | 江苏中天药业有限公司 | Sevelamer carbonate analogue, and preparation method and application thereof |
| CN115260355A (en) * | 2022-05-16 | 2022-11-01 | 江苏中天药业有限公司 | Anion exchange resin, preparation method thereof, compound of anion exchange resin and medicament and taste masking preparation thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159880A (en) * | 2011-12-14 | 2013-06-19 | 上海亿法医药科技有限公司 | Preparation method for sevelamer carbonate |
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- 2018-04-11 CN CN201810321877.9A patent/CN108440697A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159880A (en) * | 2011-12-14 | 2013-06-19 | 上海亿法医药科技有限公司 | Preparation method for sevelamer carbonate |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004352A (en) * | 2019-08-26 | 2020-04-14 | 江苏中天药业有限公司 | Sevelamer carbonate analogue, and preparation method and application thereof |
| CN111004352B (en) * | 2019-08-26 | 2021-08-31 | 江苏中天药业有限公司 | Sevelamer carbonate analogue, and preparation method and application thereof |
| CN115260355A (en) * | 2022-05-16 | 2022-11-01 | 江苏中天药业有限公司 | Anion exchange resin, preparation method thereof, compound of anion exchange resin and medicament and taste masking preparation thereof |
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