CN106750247A - 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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- CN106750247A CN106750247A CN201611237004.7A CN201611237004A CN106750247A CN 106750247 A CN106750247 A CN 106750247A CN 201611237004 A CN201611237004 A CN 201611237004A CN 106750247 A CN106750247 A CN 106750247A
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- alcohol
- aeo
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- low free
- free alcohol
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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）With fatty alcohol roh as initiator, reacted with ethylene carbonate in the presence of base catalyst, ethoxy alkyl ether is obtained；2）After ethoxy alkyl ether heats up, oxirane is added to carry out addition reaction in the presence of base catalyst, reaction adds acetic acid to neutralize, obtains low free alcohol AEO after terminating.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 few, and its AEO active constituent content is high, compared with similar product obtained in 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, biological
The degraded excellent combination property such as fast and obtain a class 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 class in status, is widely used in emulsifying agent, dispersant, profit
The fields such as humectant, detergent and cosmetics.
AEO is the polymer that a class has 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 the key factor for influenceing AEO properties of product, the AEO of low free alcohol content has
The advantages of effective component content is high, application effect is good.
At present, AEO is mainly with 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, it is few specifically designed for free alcohol content to the shadow of 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, low free alcohol AEO with excellent compatibility preparation method.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that comprise the following steps：
1）With fatty alcohol R-OH as initiator, reacted with ethylene carbonate in the presence of base catalyst, hydroxyl second is obtained
Base alkyl ether R-OHCH2CH2OH；
2）By step 1）The ethoxy alkyl ether R-OHCH for obtaining2CH2OH is heated up, and epoxy second is added in the presence of base catalyst
Alkane carries out addition reaction, and reaction adds acetic acid to neutralize, obtains low free alcohol AEO R-O after terminating（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, NaOH, sodium methoxide or more than one mixtures.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that step 1）Reaction temperature
It is 50~80 DEG C to spend, and the reaction time is 1~3 hour.
The preparation method of described a kind of 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.
The preparation method of described a kind of low free alcohol AEO, it is characterised in that step 2）Reaction temperature
It is 100~140 DEG C to spend, and 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 uses traditional base catalyst, such as potassium hydroxide, NaOH, sodium methoxide, its raw material is simple and easy to get,
Low cost, simple production process, reaction temperature are low, production efficiency is high；
2）The present invention uses two-step method synthetic technology, and the fatty alcohol alcohol APEO of synthesis has that free alcohol content is low, by-product
The advantages of thing is few, and its AEO active constituent content is high, compared with similar product obtained in prior art, this
The free alcohol content that invention is obtained in product is down to 0.7% from 6%, greatly improves the product quality of AEO.
Specific 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 methyl alcohol
Sodium, opens pressure-relief valve, and pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 50 DEG C, is reacted 2 hours.Then, close
Pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 100
DEG C, 9.0mol (396g) oxirane is passed through, lead within 2.5 hours, continue to react 0.5 hour, after completion of the reaction, cool down, release,
Acetic acid is added to 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 hydrogen-oxygens
Change potassium, open pressure-relief valve, pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 70 DEG C, is reacted 1.5 hours.So
Afterwards, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to
140 DEG C, 10.5mol (462g) oxirane is passed through, led within 3.5 hours, continue to react 0.5 hour.After completion of the reaction, cool down,
Release, adds acetic acid to neutralize, and 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 hydrogen
Sodium oxide molybdena, opens pressure-relief valve, and pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 80 DEG C, is reacted 1.0 hours.
Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat kettle temperature rising
To 120 DEG C, 6.25mol (275g) oxirane is passed through, led within 1.5 hours, continue to react 0.5 hour.After completion of the reaction, it is cold
But, release, adds acetic acid to neutralize, and 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 hydrogen-oxygens
Change potassium, open pressure-relief valve, pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 60 DEG C, is reacted 3.0 hours.So
Afterwards, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to
110 DEG C, 1.5mol (66g) oxirane is passed through, led within 0.5 hour, continue to react 0.5 hour.After completion of the reaction, cool down, unload
Pressure, adds acetic acid to neutralize, and 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 first
Sodium alkoxide, opens pressure-relief valve, and pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 65 DEG C, is reacted 2.5 hours.So
Afterwards, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to
130 DEG C, 12.75mol (561g) oxirane is passed through, led within 1.0 hours, continue to react 0.5 hour.After completion of the reaction, cool down,
Release, adds acetic acid to neutralize, and 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
NaOH, opens pressure-relief valve, and pressure-relief valve is connected by pipeline and alkali liquor absorption groove, is to slowly warm up to 75 DEG C, and reaction 2.0 is small
When.Then, pressure-relief valve is closed, oxirane measuring tank is connected with autoclave pressure, with nitrogen displacement gas reactor 3 times, treat kettle temperature
120 DEG C are risen to, 22.75mol (1001g) oxirane is passed through, led within 2.0 hours, continue to react 0.5 hour.Reaction is finished
Afterwards, cool down, release, add acetic acid to 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 and pressure
Power kettle is connected.With nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 100 DEG C, be passed through 10.0mol (440g) oxirane,
Lead within 2.5 hours, continued to react 0.5 hour.After completion of the reaction, cool down, release, add acetic acid to 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, by oxirane measuring tank with
Autoclave pressure is connected.With nitrogen displacement gas reactor 3 times, treat that kettle temperature rises to 140 DEG C, be passed through 11.0mol (484g) oxirane,
Lead within 3.5 hours, continued to react 0.5 hour.After completion of the reaction, cool down, release, add acetic acid to 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 NaOH, by oxirane measuring tank
It 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 second
Alkane, has led to for 1.5 hours, continues to react 0.5 hour.After completion of the reaction, cool down, release, add acetic acid to 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 is obtained, its free alcohol content
Substantially reduce, 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）With fatty alcohol R-OH as initiator, reacted with ethylene carbonate in the presence of base catalyst, hydroxyl second is obtained
Base alkyl ether R-OHCH2CH2OH；
2）By step 1）The ethoxy alkyl ether R-OHCH for obtaining2CH2OH is heated up, and epoxy second is added in the presence of base catalyst
Alkane carries out addition reaction, and reaction adds acetic acid to neutralize, obtains low free alcohol AEO R-O after terminating（CH2CH2O）m+ 1H,
Its synthetic route is as follows：
,
Wherein：R is C8~10、C12~14Or C16~18Saturated straight chain alkyl；M=1~21.
2. a kind of 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.
3. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that alkali
Property catalyst be any one or more than one mixtures in potassium hydroxide, NaOH, sodium methoxide.
4. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that step
Rapid 1）Reaction temperature be 50~80 DEG C, the reaction time be 1~3 hour.
5. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that institute
It is fatty alcohol and the 0.5~1% of ethylene carbonate gross mass to state the addition of base catalyst.
6. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that fat
Fat alcohol is 1 with the molar ratio of ethylene carbonate：1.
7. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that fat
Fat alcohol is 1 with the molar ratio of oxirane：1-21.
8. a kind of preparation method of low free alcohol AEO according to claim 1, it is characterised in that step
Rapid 2）Reaction temperature be 100~140 DEG C, the reaction time be 1~4 hour.
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Cited By (2)
| 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 |
| CN109265323A (en) * | 2018-08-23 | 2019-01-25 | 浙江三江化工新材料有限公司 | A kind of preparation method of Narrow Molecular Weight Distribution bisphenol A polyethenoxy ether |
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 isomerous 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 |
-
2016
- 2016-12-28 CN CN201611237004.7A patent/CN106750247B/en active Active
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 isomerous 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 |
Cited By (3)
| 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 |
| CN109265323A (en) * | 2018-08-23 | 2019-01-25 | 浙江三江化工新材料有限公司 | A kind of preparation method of Narrow Molecular Weight Distribution bisphenol A polyethenoxy ether |
| 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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