CN106750247B - A kind of preparation method of low free alcohol AEO - Google Patents
A kind of preparation method of low free alcohol AEO Download PDFInfo
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- CN106750247B CN106750247B CN201611237004.7A CN201611237004A CN106750247B CN 106750247 B CN106750247 B CN 106750247B CN 201611237004 A CN201611237004 A CN 201611237004A CN 106750247 B CN106750247 B CN 106750247B
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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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2603—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 from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—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 from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—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 from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2642—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 from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
The invention discloses a kind of preparation method of low free alcohol AEO, it comprises the following steps：1）Using fatty alcohol roh as initiator, reacted in the presence of base catalyst with ethylene carbonate, ethoxy alkyl ether is made；2）After the heating of ethoxy alkyl ether, oxirane is added in the presence of base catalyst and carries out addition reaction, after reaction terminates plus acetic acid neutralizes, and obtains low free alcohol AEO.The present invention uses two-step method synthetic technology, the fatty alcohol alcohol APEO of synthesis has the advantages that free alcohol content is low, accessory substance is few, and its AEO active constituent content is high, compared with similar product made from prior art, the free alcohol content that the present invention is obtained in product is down to 0.7% from 6%, greatly improves the product quality of AEO.
Description
Technical field
The invention belongs to nonionic surfactant synthesis technical field, and in particular to a kind of low free alcohol fatty alcohol polyoxy
The preparation method of vinethene.
Background technology
AEO be with strong detergency, resistance to hard water, cold washing effect are good, compatibility ability is strong, biology
The degraded excellent combination property such as fast and obtain a kind of Determination of Polyoxyethylene Non-ionic Surfactants of fast development, also right and wrong from
Kind is most in sub- surfactant, yield is maximum, the most important one kind in status, is widely used in emulsifying agent, dispersant, profit
The fields such as humectant, detergent and cosmetics.
AEO is a kind of polymer with different carbon chain number and different adduct numbers, the performance of product with
The difference of carbochain number and adduct number in AEO molecule and change.The free alcohol content of AEO
It is there is the AEO of low free alcohol content an important factor for influenceing AEO properties of product
The advantages that effective component content is high, application effect is good.
At present, AEO is mainly using fatty alcohol as initiator, in different type catalyst（Acidic catalyst
Agent, base catalyst, alkaline earth catalyst, compound base catalyst etc.）In the presence of, and oxirane direct addition reaction and make
.The report of the overwhelming majority is concentrated mainly on different types of catalyst and is distributed width to AEO middle-molecular-weihydroxyethyl
In narrow, by-products content influence, few shadows specifically for free alcohol content to AEO properties of product
Loud research and report.
The content of the invention
For the above-mentioned problems in the prior art, it is an object of the invention to provide a kind of free alcohol content it is low, have
Effective component content is high, has the preparation method of the low free alcohol AEO of excellent compatibility.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that comprise the following steps：
1）Using fatty alcohol R-OH as initiator, reacted, be made with ethylene carbonate in the presence of base catalyst
Ethoxy alkyl ether R-OHCH2CH2OH；
2）By step 1）Obtained ethoxy alkyl ether R-OHCH2CH2OH is heated up, and ring is added in the presence of base catalyst
Oxidative ethane carries out addition reaction, and after reaction terminates plus acetic acid neutralizes, and obtains low free alcohol AEO R-O
（CH2CH2O）m+1H,
Its synthetic route is as follows：
,
Wherein：R is C8~10、C12~14Or C16~18Saturated straight chain alkyl；M=1~21.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that fatty alcohol R-OH is
C8~10Fatty alcohol, C12~14Fatty alcohol or C16~18Any one of fatty alcohol.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that base catalyst is hydrogen
Any one in potassium oxide, sodium hydroxide, sodium methoxide or more than one mixtures.
A kind of preparation method of described low free alcohol AEO, it is characterised in that step 1）Reaction temperature
Spend for 50~80 DEG C, the reaction time is 1~3 hour.
A kind of preparation method of described low free alcohol AEO, it is characterised in that the base catalyst
Addition be the 0.5~1% of fatty alcohol and ethylene carbonate gross mass.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that fatty alcohol and ethylene
The molar ratio of alkene ester is 1：1.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that fatty alcohol and epoxy second
The molar ratio of alkane is 1：1-21.
A kind of preparation method of described low free alcohol AEO, it is characterised in that step 2）Reaction temperature
Spend for 100~140 DEG C, the reaction time is 1~4 hour.
By using the above method, compared with prior art, the present invention has advantages below：
1）The present invention is simple using traditional base catalyst, such as potassium hydroxide, sodium hydroxide, sodium methoxide, its raw material
It is easy to get, cost is low, simple production process, reaction temperature is low, production efficiency is high；
2）The present invention uses two-step method synthetic technology, the fatty alcohol alcohol APEO of synthesis have free alcohol content it is low,
The advantages that accessory substance is few, and its AEO active constituent content is high, with prior art made from similar product phase
Than the free alcohol content that the present invention is obtained in product is down to 0.7% from 6%, greatly improves the product of AEO
Quality.
Embodiment
The C of embodiment 112~14Alcohol polyoxyethylene（10）The preparation of ether
1.0mol is added in pressure reaction still（193.0g）C12~14Alcohol, 1.0mol（88g）Ethylene carbonate and 2.81g
Sodium methoxide, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 50 DEG C, is reacted 2 hours.So
Afterwards, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treats that kettle temperature rises to
100 DEG C, 9.0mol (396g) oxirane is passed through, has been led within 2.5 hours, continue reaction 0.5 hour, after completion of the reaction, cooling, unloaded
Pressure, add acetic acid and neutralize, blowing obtains C12~14Alcohol polyoxyethylene（10）Ether.
The C of embodiment 216~18Alcohol polyoxyethylene（22）The preparation of ether
0.5mol is added in pressure reaction still（124.5g）C16~18Alcohol, 0.5mol（44g）Ethylene carbonate and 1.12g
Potassium hydroxide, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 70 DEG C, reaction 1.5 is small
When.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treats kettle temperature
140 DEG C are risen to, 10.5mol (462g) oxirane is passed through, has led within 3.5 hours, continues reaction 0.5 hour.After completion of the reaction,
Cooling, release, add acetic acid and neutralize, blowing obtains C16~18Alcohol polyoxyethylene（22）Ether.
The C of embodiment 38~10Alcohol polyoxyethylene（6）The preparation of ether
1.25mol is added in pressure reaction still（171.25g）C8~10Alcohol, 1.25mol（110g）Ethylene carbonate and
2.25g sodium hydroxides, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 80 DEG C, reaction
1.0 hour.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, is treated
Kettle temperature rises to 120 DEG C, is passed through 6.25mol (275g) oxirane, has led within 1.5 hours, continues reaction 0.5 hour.React
Bi Hou, cooling, release, add acetic acid and neutralize, blowing obtains C8~10Alcohol polyoxyethylene（6）Ether.
The C of embodiment 412~14Alcohol polyoxyethylene（2）The preparation of ether
1.5mol is added in pressure reaction still（289.5g）C12~14Alcohol, 1.5mol（132g）Ethylene carbonate and 2.11g
Potassium hydroxide, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 60 DEG C, reaction 3.0 is small
When.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treats kettle temperature
110 DEG C are risen to, 1.5mol (66g) oxirane is passed through, has led within 0.5 hour, continues reaction 0.5 hour.After completion of the reaction, it is cold
But, release, add acetic acid and neutralize, blowing obtains C12~14Alcohol polyoxyethylene（2）Ether.
The C of embodiment 58~10Alcohol polyoxyethylene（18）The preparation of ether
0.75mol is added in pressure reaction still（102.75g）C8~10Alcohol, 0.75mol（66g）Ethylene carbonate and
1.52g sodium methoxides, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 65 DEG C, reaction 2.5
Hour.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treats kettle
Temperature rises to 130 DEG C, is passed through 12.75mol (561g) oxirane, has led within 1.0 hours, continues reaction 0.5 hour.Reaction finishes
Afterwards, cool down, release, add acetic acid and neutralize, blowing obtains C8~10Alcohol polyoxyethylene（18）Ether.
The C of embodiment 616~18Alcohol polyoxyethylene（14）The preparation of ether
1.75mol is added in pressure reaction still（435.75g）C16~18Alcohol, 1.75mol（154g）Ethylene carbonate and
3.54g sodium hydroxides, pressure-relief valve is opened, pressure-relief valve is connected by pipeline with alkali liquor absorption groove, is to slowly warm up to 75 DEG C, reaction
2.0 hour.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, is treated
Kettle temperature rises to 120 DEG C, is passed through 22.75mol (1001g) oxirane, has led within 2.0 hours, continues reaction 0.5 hour.Reaction
After, cooling, release, add acetic acid and neutralize, blowing obtains C16~18Alcohol polyoxyethylene（14）Ether.
The C of comparative example 112~14Alcohol polyoxyethylene（10）The preparation of ether
1.0mol is added in pressure reaction still（193.0g）C12~14Alcohol and 2.81g sodium methoxides, by oxirane measuring tank
It is connected with autoclave pressure.With nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 100 DEG C, be passed through 10.0mol (440g) epoxy second
Alkane, lead within 2.5 hours, continued reaction 0.5 hour.After completion of the reaction, cool down, release, add acetic acid and neutralize, blowing.
The C of comparative example 216~18Alcohol polyoxyethylene（22）The preparation of ether
0.5mol is added in pressure reaction still（124.5g）C16~18Alcohol and 1.12g potassium hydroxide, oxirane is measured
Tank is connected with autoclave pressure.With nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 140 DEG C, be passed through 11.0mol (484g) epoxy
Ethane, lead within 3.5 hours, continued reaction 0.5 hour.After completion of the reaction, cool down, release, add acetic acid and neutralize, blowing.
The C of comparative example 38~10Alcohol polyoxyethylene（6）The preparation of ether
1.25mol is added in pressure reaction still（171.25g）C8~10Alcohol and 2.25g sodium hydroxides, by oxirane meter
Measuring tank is connected with autoclave pressure.With nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 120 DEG C, be passed through 7.5mol (330g) epoxy
Ethane, lead within 1.5 hours, continued reaction 0.5 hour.After completion of the reaction, cool down, release, add acetic acid and neutralize, blowing.
Fatty alcohol prepared in prepared AEO and comparative example 1~3 in above-described embodiment 1~6
APEO after tested, the following form of specific targets：
| Sequence number | Carbochain number in molecule | Molecule ethylene oxide number | Free alcohol content（%） |
| Embodiment 1 | 12-14 | 10 | 1.29 |
| Embodiment 2 | 16-18 | 22 | 0.78 |
| Embodiment 3 | 8-10 | 6 | 1.36 |
| Embodiment 4 | 12-14 | 2 | 2.63 |
| Embodiment 5 | 8-10 | 18 | 0.69 |
| Embodiment 6 | 16-18 | 14 | 1.17 |
| Comparative example 1 | 12-14 | 10 | 5.07 |
| Comparative example 2 | 16-18 | 22 | 3.14 |
| Comparative example 3 | 8-10 | 6 | 6.73 |
As can be drawn from Table 1, compared with prior art, in the AEO that the present invention obtains, its free alcohol
Content substantially reduces, therefore AEO active constituent content is high, improves the quality of AEO.
Claims (8)
1. a kind of preparation method of low free alcohol AEO, it is characterised in that comprise the following steps：
1）Using fatty alcohol R-OH as initiator, reacted in the presence of base catalyst with ethylene carbonate, hydroxyl second is made
Base alkyl ether R-OHCH2CH2OH, reaction temperature are 50~80 DEG C；
2）By step 1）Obtained ethoxy alkyl ether R-OHCH2CH2OH is heated up, and epoxy second is added in the presence of base catalyst
Alkane carries out addition reaction, and reaction temperature is 100~140 DEG C, and after reaction terminates plus acetic acid neutralizes, and obtains low free alcohol poly alkyl alcohol
Oxygen vinethene R-O（CH2CH2O）m+1H,
Its synthetic route is as follows：
,
Wherein：R is C8~10、C12~14Or C16~18Saturated straight chain alkyl；M=1~21.
A kind of 2. preparation method of low free alcohol AEO according to claim 1, it is characterised in that fat
Fat alcohol R-OH is C8~10Fatty alcohol, C12~14Fatty alcohol or C16~18Any one of fatty alcohol.
A kind of 3. preparation method of low free alcohol AEO according to claim 1, it is characterised in that alkali
Property catalyst be potassium hydroxide, sodium hydroxide, any one or more than one mixtures in sodium methoxide.
A kind of 4. preparation method of low free alcohol AEO according to claim 1, it is characterised in that step
Rapid 1）Reaction time be 1~3 hour.
A kind of 5. preparation method of low free alcohol AEO according to claim 1, it is characterised in that institute
The addition for stating base catalyst is the 0.5~1% of fatty alcohol and ethylene carbonate gross mass.
A kind of 6. preparation method of low free alcohol AEO according to claim 1, it is characterised in that fat
The molar ratio of fat alcohol and ethylene carbonate is 1：1.
A kind of 7. preparation method of low free alcohol AEO according to claim 1, it is characterised in that fat
The molar ratio of fat alcohol and oxirane is 1：1-21.
A kind of 8. preparation method of low free alcohol AEO according to claim 1, it is characterised in that step
Rapid 2）Reaction time be 1~4 hour.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108130214A (en) * | 2017-12-08 | 2018-06-08 | 武汉奥克特种化学有限公司 | A kind of functional form cleaning surfactant and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109265323B (en) * | 2018-08-23 | 2021-09-28 | 浙江三江化工新材料有限公司 | Preparation method of bisphenol A polyoxyethylene ether with narrow molecular weight distribution |
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| CN101225161A (en) * | 2007-12-21 | 2008-07-23 | 王伟松 | Method for synthesizing isomeric tridecanol polyoxyethylene ether |
| CN102352029A (en) * | 2011-07-19 | 2012-02-15 | 吴金海 | Method for preparing octadecyl amine polyoxyethylene ether |
| CN102634005A (en) * | 2012-03-15 | 2012-08-15 | 上海多纶化工有限公司 | Synthesis method of isomeric alcohol polyethenoxy ether |
| CN103449983A (en) * | 2013-09-24 | 2013-12-18 | 浙江绿科安化学有限公司 | Method for preparing anacardol polyoxyethylene ether |
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2016
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830263A (en) * | 1985-05-09 | 1989-05-16 | Basf Corporation | Thermally stable polyoxyalkylene heat transfer fluids |
| CN101225161A (en) * | 2007-12-21 | 2008-07-23 | 王伟松 | Method for synthesizing isomeric tridecanol polyoxyethylene ether |
| CN102352029A (en) * | 2011-07-19 | 2012-02-15 | 吴金海 | Method for preparing octadecyl amine polyoxyethylene ether |
| CN102634005A (en) * | 2012-03-15 | 2012-08-15 | 上海多纶化工有限公司 | Synthesis method of isomeric alcohol polyethenoxy ether |
| CN103449983A (en) * | 2013-09-24 | 2013-12-18 | 浙江绿科安化学有限公司 | Method for preparing anacardol polyoxyethylene ether |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108130214A (en) * | 2017-12-08 | 2018-06-08 | 武汉奥克特种化学有限公司 | A kind of functional form cleaning surfactant and preparation method thereof |
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