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CN107325274A - A kind of preparation method of low color polyoxyethylene sorbitan monoleate - Google Patents

A kind of preparation method of low color polyoxyethylene sorbitan monoleate Download PDF

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Publication number
CN107325274A
CN107325274A CN201710760065.XA CN201710760065A CN107325274A CN 107325274 A CN107325274 A CN 107325274A CN 201710760065 A CN201710760065 A CN 201710760065A CN 107325274 A CN107325274 A CN 107325274A
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preparation
reaction
anhydrous sorbitol
oleate
polyoxyethylene sorbitan
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朱建民
刘兆滨
仲崇纲
陈杨英
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Liaoning Oxiran Pharmaceutical Excipient Co Ltd
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Liaoning Oxiran Pharmaceutical Excipient Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/04End-capping

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The present invention provides a kind of preparation method of low color polyoxyethylene sorbitan monoleate, including:In the presence of inorganic acid and antioxidant, sorbierite is carried out dehydration reaction, obtain anhydrous sorbitol;Add organic sodium alkoxide to adjust the pH value of anhydrous sorbitol to pH=10 12, oxirane is added afterwards and carries out ethoxylation with anhydrous sorbitol, anhydrous sorbitol APEO is obtained;And in a nitrogen atmosphere, add oleate and carry out ester exchange reaction with anhydrous sorbitol APEO, obtain low color polyoxyethylene sorbitan monoleate.The preparation method of the present invention avoids the process that the activated carbon used in conventional method, hydrogen peroxide carry out multistep decolouring, separating treatment is not needed in the middle of each course of reaction, ester exchange reaction is carried out using oleate simultaneously rather than direct esterification is carried out using oleic acid, good process repeatability, production efficiency is substantially improved, and product quality is stable.

Description

A kind of preparation method of low color polyoxyethylene sorbitan monoleate
Technical field
The present invention relates to a kind of chemical industry synthesis method, and in particular to a kind of preparation method of low color polyoxyethylene sorbitan monoleate.
Background technology
Polyoxyethylene sorbitan monoleate, is commonly called as Tween 80, also referred to as polyoxyethylene (20) sorbitan monooleate, and it is a kind of hydrophilic Type nonionic surfactant, there is significant resistance to electrolyte, and hydrophily is strong, is widely used in liquid, semisolid, solid In preparation, as O/W types emulsifying agent, solubilizer, wetting agent, dispersant and stabilizer.Because there is preferable hydrotropy to act on for it, When preparing the injection of insoluble drug, cosolvent, emulsifying agent and stabilizer are commonly used for.
Current polyoxyethylene sorbitan monoleate synthetic method generally has following two:(1) sorbierite is acted on oleic acid in base catalyst It is lower that dehydration and esterification occur simultaneously, obtain sorbitan monooleate (being commonly called as sorbester p17), then again with 20 molar parts Ring of numbers oxidative ethane condensation reaction, obtains Tween-80, refers to United States Patent (USP) US4297290.(2) sorbierite is in acidic catalyst First it is dehydrated under agent effect, obtains anhydrous sorbitol, then occurring esterification with oleic acid again obtains sorbitan monooleate, Finally reacted with 20 molfraction ethylene oxide condensations, obtain polyoxyethylene sorbitan monoleate.US8334397B2, which is disclosed, uses methyl oleate generation The process that reaction prepares sorbitan monooleate, the hardship of its polyoxyethylene sorbitan monoleate prepared are carried out for oleic acid and anhydrous sorbitol Taste can be significantly reduced.In addition, CN101701065B, CN102127217B etc. disclose a new preparation process:Sorbierite First dehydration obtains anhydrous sorbitol under acidic catalyst effect, is then lost with the reaction of 20 molfraction ethylene oxide condensations Water sorbitol polyoxyethylene ether, finally occurs esterification with oleic acid again and obtains polyoxyethylene sorbitan monoleate.
Three of the above method has the drawback that:In order to prepare the polyoxyethylene sorbitan monoleate of low color number, mistake is being prepared It is required for being decolourized with activated carbon after water sorbierite or sorbitan monooleate, it is after 80s preparing polysorbate It is also required to be decolourized with activated carbon or hydrogen peroxide, and then can just obtains the polyoxyethylene sorbitan monoleate of low color number.In preparation process not Its application in downstream product all can be influenceed more than 500 using the color number of the polyoxyethylene sorbitan monoleate obtained by any decolorization process.
The content of the invention
In view of the deficienciess of the prior art, can conveniently prepare low color polysorbate it is an object of the invention to provide one kind 80 method, the problem of solving complicated decolorization process in the prior art, low production efficiency.
To achieve the above object, the present invention is adopted the following technical scheme that:
A kind of preparation method of low color polyoxyethylene sorbitan monoleate, including:
In the presence of inorganic acid and antioxidant, sorbierite is carried out dehydration reaction, obtain anhydrous sorbitol;
Add organic sodium alkoxide to adjust the pH value of anhydrous sorbitol to pH=10-12, oxirane and dehydration are added afterwards Sorbierite carries out ethoxylation, obtains anhydrous sorbitol APEO;And
In a nitrogen atmosphere, add oleate and carry out ester exchange reaction with anhydrous sorbitol APEO, obtain low color Number polyoxyethylene sorbitan monoleate.
In an embodiment of the preparation method of the present invention, the reaction temperature of the dehydration reaction is 100~180 DEG C, vacuum is 700~759mmHg, and the reaction time is 5-15h.
In another embodiment of the preparation method of the present invention, the inorganic acid is in sulfuric acid, phosphoric acid, phosphorous acid One or more, the antioxidant is the one or more in sodium hypophosphite, sodium sulfite, sodium hydrogensulfite.
In another embodiment of the preparation method of the present invention, the consumption of the inorganic acid is sorbierite weight 0.5-1.5%, the consumption of the antioxidant is the 0.1-0.5% of sorbierite weight.
In another embodiment of the preparation method of the present invention, the organic sodium alkoxide is sodium methoxide or caustic alcohol.
In another embodiment of the preparation method of the present invention, the weight ratio of oxirane and anhydrous sorbitol is 1: 0.17~0.20.
In another embodiment of the preparation method of the present invention, the reaction temperature of the ethoxylation is 120 ~160 DEG C, the reaction time is 4-10h.
In another embodiment of the preparation method of the present invention, the oleate is methyl oleate or ethyl oleate.
In another embodiment of the preparation method of the present invention, anhydrous sorbitol APEO and the oleate Weight ratio be 1: 0.28~0.35.
In another embodiment of the preparation method of the present invention, the reaction temperature of the ester exchange reaction is 150- 210 DEG C, the reaction time is 6-14h.
The present invention preparation method another embodiment in, after ester exchange reaction, in addition to add go from Sub- water, inorganic ions is removed by ion exchange resin post, is adjusted the electrical conductivity of product to less than 50, is then steamed moisture.
The preparation method of the present invention avoids the mistake that the activated carbon used in conventional method, hydrogen peroxide carry out multistep decolouring Separating treatment is not needed in the middle of journey, each course of reaction, while carrying out ester exchange reaction using oleate rather than using oleic acid Direct esterification is carried out, good process repeatability, production efficiency is substantially improved, product quality is stable.
Embodiment
Technical scheme is described further below according to specific embodiment.Protection scope of the present invention is not limited In following examples, these examples are enumerated merely for exemplary purpose without limiting the present invention in any way.
The preparation method of the present invention is broadly divided into following several stages:Dehydration reaction prepares anhydrous sorbitol;Ethoxylation Reaction prepares anhydrous sorbitol APEO;And ester exchange reaction prepares polyoxyethylene sorbitan monoleate.
It is in the presence of inorganic acid and antioxidant, sorbierite is carried out dehydration reaction, obtain dehydration in dehydration reaction Sorbierite, reaction temperature is 100~180 DEG C, and vacuum is 700~759mmHg, and the reaction time is 5-15h.
Sorbierite used is usually sorbitol aqueous solution in dehydration reaction, and its mass concentration is 70% or so.
Inorganic acid used is the one or more in sulfuric acid, phosphoric acid, phosphorous acid in dehydration reaction, and consumption is sorbierite weight The 0.5-1.5% of amount.
Antioxidant used is the one or more in sodium hypophosphite, sodium sulfite, sodium hydrogensulfite in dehydration reaction, is used Measure as the 0.1-0.5% of sorbierite weight.Antioxidant is able to ensure that the oxygen dissolved in course of reaction cannot participate in reaction and produce Coloring matter, so as to substantially reduce the color number of anhydrous sorbitol, and then reduces the color number of final product polyoxyethylene sorbitan monoleate.
Before ethoxylation, the pH of the anhydrous sorbitol obtained by previous step need to be adjusted to alkalescence, it is usually used to have Machine sodium alkoxide such as sodium methoxide or caustic alcohol are adjusted, and the pH of anhydrous sorbitol is adjusted to pH=10-12.
Above-mentioned organic sodium alkoxide is added generally in the form of organic alcoholic solution, such as methanol solution of sodium methylate, in order to avoid Low boiling Organic Alcohol also assists in ethoxylation generation accessory substance, in addition it is also necessary to carry out second again after carrying out vacuum removal low boiling Organic Alcohol Oxygen glycosylation reaction.
It is that oxirane carries out the obtained dehydration mountain of reaction with the anhydrous sorbitol obtained by previous step in ethoxylation Pears alcohol APEO, the addition total amount of its ethylene oxide and the weight ratio of anhydrous sorbitol are 1: 0.17~0.20, and it rubs That ratio about 20:1, to ensure being smoothed out for reaction.
The reaction temperature of ethoxylation is 120~160 DEG C, and the reaction time is 4-10h.
After ethoxylation, it is passed through inert gas such as nitrogen to replace the air in reaction vessel, adjusts reaction gas Atmosphere, adds oleate afterwards, it is carried out ester exchange reaction with the anhydrous sorbitol APEO obtained by previous step and is made Polyoxyethylene sorbitan monoleate crude product.
Oleate used is methyl oleate or ethyl oleate in ester exchange reaction, and esterification is carried out using ester-interchange method Rather than direct esterification is carried out using oleic acid, can so it reaction system is maintained close to neutrality, it is to avoid under the conditions of strong acid-base Generate coloring matter.
In ester exchange reaction, the weight ratio of anhydrous sorbitol APEO and oleate is 1: 0.28~0.35, reaction Temperature is 150-210 DEG C, and the reaction time is 6-14h.
Extra separating treatment need not be carried out in the middle of dehydration reaction, ethoxylation and ester exchange reaction, also Avoid the process that the activated carbon used in conventional method, hydrogen peroxide carry out multistep decolouring.
After ester exchange reaction, can also deionization processing be carried out to polyoxyethylene sorbitan monoleate crude product, that is, add deionized water, led to Cross ion exchange resin post and remove inorganic ions, adjust the electrical conductivity of product to less than 50, then steam moisture, finally give low color number Polyoxyethylene sorbitan monoleate.
Ion exchange resin post used is the group that cationic resin column and resin anion (R.A.) post used in conventional deionization are formed Close, evaporation efficiency can be improved using thin film evaporator by steaming moisture.
Unless otherwise defined, term used herein is the implication that those skilled in the art are generally understood that.
With reference to embodiment, the invention will be further described.
Embodiment
Determination of colority opens the SD-2 chromascopes of prestige electronics using Shanghai in each embodiment, and conductivity meter is DDS-307A types.
Embodiment 1
(1) at room temperature, 100g70% sorbitol aqueous solution is added into 250mL four-hole bottle, stirring is started and is warming up to 90 DEG C, vacuum 750mmHg is evacuated down to, water is steamed in decompression until water removal is complete.It is continuously heating to 125 DEG C of temperature in the kettle, Xiang Qi It is middle to add the nitration mixture catalyst 0.7g (phosphoric acid configured:Sulfuric acid=17:1 weight ratio) and antioxidant sodium hypophosphite 0.14g.Subtract Pressure is warming up to 135 DEG C, maintains vacuum 750mmHg, is incubated 5 hours, obtains anhydrous sorbitol 63g.
(2) 60 DEG C are cooled to, 20% methanol solution of sodium methylate is added thereto and is adjusted to pH=10.5, is stirred 30 minutes, It is evacuated down to 350mmHg and removes low-boiling-point substance methanol therein.It is then transferred into 1L high pressure ethoxylation kettles, nitrogen displacement kettle In air three times, be then warming up to 125 DEG C, oxirane added in batches and maintains pressure to be no more than 0.4MPa, until epoxy The addition of ethane is 338g, continues to react 1h, and untill reaction pressure no longer declines, kettle is driven in decompression, obtains Sorbitan Alcohol APEO 401g.
(3) above-mentioned anhydrous sorbitol APEO is transferred in 1L reaction kettle of the esterification, adds methyl oleate 115g, so After be warming up to 180 DEG C, nitrogen bubble reaction 12h, cooling obtains polyoxyethylene sorbitan monoleate crude product 502g.
(4) added into polyoxyethylene sorbitan monoleate crude product after 500g deionized waters, 30min is stirred, then by resin cation Post and resin anion (R.A.) post carry out ion exchange, control the electrical conductivity of product<50, further with thin film evaporator in 100 DEG C of steamings The polyoxyethylene sorbitan monoleate product 485g that color number is 75 is obtained after water outlet.
Embodiment 2
(1) at room temperature, 100g70% sorbitol aqueous solution is added into 250mL four-hole bottle, stirring is started and is warming up to 90 DEG C, vacuum 720mmHg is evacuated down to, water is steamed in decompression until water removal is complete.It is continuously heating to 125 DEG C of temperature in the kettle, Xiang Qi It is middle to add the phosphoric acid catalyst 0.7g and antioxidant Sodium Thiosulfate 0.14g configured.Decompression is warming up to 150 DEG C, maintains vacuum 720mmHg is spent, 10 hours is incubated, obtains anhydrous sorbitol 65g.
(2) 60 DEG C are cooled to, 20% methanol solution of sodium methylate is added thereto and is adjusted to pH=12, stirs 30 minutes, takes out Vacuum removes low-boiling-point substance methanol therein to 350mmHg.It is then transferred into 1L high pressure ethoxylation kettles, nitrogen displacement kettle Air three times, be then warming up to 155 DEG C, oxirane added in batches and maintains pressure to be no more than 0.4MPa, until epoxy second The addition of alkane is 345g, continues to react 1h, and untill reaction pressure no longer declines, kettle is driven in decompression, obtains anhydrous sorbitol APEO 407g.
(3) above-mentioned anhydrous sorbitol APEO is transferred in 1L reaction kettle of the esterification, adds methyl oleate 120g, so After be warming up to 210 DEG C, nitrogen bubble reaction 6h, cooling obtains polyoxyethylene sorbitan monoleate crude product 506g.
(4) added into polyoxyethylene sorbitan monoleate crude product after 450g deionized waters, 30min is stirred, then by resin cation Post and resin anion (R.A.) post carry out ion exchange, control the electrical conductivity of product<50, further with thin film evaporator in 100 DEG C of steamings The polyoxyethylene sorbitan monoleate product 490g that color number is 85 is obtained after water outlet.
Embodiment 3
(1) at room temperature, 100g70% sorbitol aqueous solution is added into 250mL four-hole bottle, stirring is started and is warming up to 90 DEG C, vacuum 735mmHg is evacuated down to, water is steamed in decompression until water removal is complete.It is continuously heating to 125 DEG C of temperature in the kettle, Xiang Qi It is middle to add the phosphorous acid catalyst 0.35g and antioxidant sodium hydrogensulfite 0.32g configured.Decompression is warming up to 175 DEG C, remains true Reciprocal of duty cycle 735mmHg, is incubated 8 hours, obtains anhydrous sorbitol 60g.
(2) 60 DEG C are cooled to, 20% methanol solution of sodium methylate is added thereto and is adjusted to pH=11.5, is stirred 30 minutes, It is evacuated down to 350mmHg and removes low-boiling-point substance methanol therein.It is then transferred into 1L high pressure ethoxylation kettles, nitrogen displacement kettle In air three times, be then warming up to 135 DEG C, oxirane added in batches and maintains pressure to be no more than 0.4MPa, until epoxy The addition of ethane is 335g, continues to react 1h, and untill reaction pressure no longer declines, kettle is driven in decompression, obtains Sorbitan Alcohol APEO 395g.
(3) above-mentioned anhydrous sorbitol APEO is transferred in 1L reaction kettle of the esterification, adds ethyl oleate 135g, so After be warming up to 170 DEG C, nitrogen bubble reaction 14h, cooling obtains polyoxyethylene sorbitan monoleate crude product 522g.
(4) added into polyoxyethylene sorbitan monoleate crude product after 530g deionized waters, 30min is stirred, then by resin cation Post and resin anion (R.A.) post carry out ion exchange, control the electrical conductivity of product<50, further with thin film evaporator in 100 DEG C of steamings The polyoxyethylene sorbitan monoleate product 510g that color number is 75 is obtained after water outlet.
In summary, preparation method of the invention reduces color number in the preparation of anhydrous sorbitol using antioxidant, it is to avoid The activated carbon, the hydrogen peroxide that are used in conventional method be not required in the middle of the process of multistep decolouring, each course of reaction to be separated Processing, while carrying out ester exchange reaction using oleate rather than carrying out direct esterification, good process repeatability, production using oleic acid Efficiency is substantially improved, and product quality is stable.
Those skilled in the art should be noted that embodiment described in the invention is only exemplary, can be Various other replacements, changes and improvements are made in the scope of the present invention.Thus, the invention is not restricted to above-mentioned embodiment, and only It is defined by the claims.

Claims (11)

1. a kind of preparation method of low color polyoxyethylene sorbitan monoleate, including:
In the presence of inorganic acid and antioxidant, sorbierite is carried out dehydration reaction, obtain anhydrous sorbitol;
Add organic sodium alkoxide to adjust the pH value of anhydrous sorbitol to pH=10-12, oxirane and Sorbitan are added afterwards Alcohol carries out ethoxylation, obtains anhydrous sorbitol APEO;And
In a nitrogen atmosphere, add oleate and carry out ester exchange reaction with anhydrous sorbitol APEO, obtain low color number and gather Sorb ester 80.
2. preparation method according to claim 1, wherein the reaction temperature of dehydration reaction is 100~180 DEG C, vacuum Spend for 700~759mmHg, the reaction time is 5-15h.
3. preparation method according to claim 1, wherein the inorganic acid be one kind in sulfuric acid, phosphoric acid, phosphorous acid or A variety of, the antioxidant is the one or more in sodium hypophosphite, sodium sulfite, sodium hydrogensulfite.
4. preparation method according to claim 3, wherein the consumption of the inorganic acid is the 0.5- of sorbierite weight 1.5%, the consumption of the antioxidant is the 0.1-0.5% of sorbierite weight.
5. preparation method according to claim 1, wherein the organic sodium alkoxide is sodium methoxide or caustic alcohol.
6. the weight ratio of preparation method according to claim 1, its ethylene oxide and anhydrous sorbitol be 1: 0.17~ 0.20。
7. preparation method according to claim 1, wherein the reaction temperature of the ethoxylation is 120~160 DEG C, Reaction time is 4-10h.
8. preparation method according to claim 1, wherein the oleate is methyl oleate or ethyl oleate.
9. preparation method according to claim 8, wherein anhydrous sorbitol APEO and the weight of the oleate Than for 1: 0.28~0.35.
10. preparation method according to claim 1, wherein the reaction temperature of the ester exchange reaction is 150-210 DEG C, instead It is 6-14h between seasonable.
11. preparation method according to any one of claim 1 to 10, wherein after ester exchange reaction, in addition to add Enter deionized water, inorganic ions is removed by ion exchange resin post, adjust the electrical conductivity of product to less than 50, then steam moisture.
CN201710760065.XA 2017-08-28 2017-08-28 A kind of preparation method of low color polyoxyethylene sorbitan monoleate Pending CN107325274A (en)

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CN110591074A (en) * 2019-09-27 2019-12-20 湖北葛店人福药用辅料有限责任公司 Polysorbate 80 for injection and preparation method thereof
CN114349720A (en) * 2022-01-24 2022-04-15 抚顺东科新能源科技有限公司 Preparation method of colorless sorbitan

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