CN103449983A - Method for preparing anacardol polyoxyethylene ether - Google Patents
Method for preparing anacardol polyoxyethylene ether Download PDFInfo
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- CN103449983A CN103449983A CN2013104360586A CN201310436058A CN103449983A CN 103449983 A CN103449983 A CN 103449983A CN 2013104360586 A CN2013104360586 A CN 2013104360586A CN 201310436058 A CN201310436058 A CN 201310436058A CN 103449983 A CN103449983 A CN 103449983A
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- polyoxyethylene ether
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Abstract
The invention discloses a method for preparing anacardol polyoxyethylene ether. The method for preparing the anacardol polyoxyethylene ether is characterized in that anacardol serves as raw materials, polymerization reaction occurs between the anacardol and ethylene oxide under the action of a catalyzer, adsorption treatment is carried out by means of activated clay, and then the anacardol polyoxyethylene ether is obtained. The structural formula of the anacardol polyoxyethylene ether is R=C15H31, R=C15H29, R=C15H27, R=C15H25, n=3-25. A product prepared with the method has the advantage of being free of odor and wide in application fields.
Description
technical field
The present invention relates to a kind of preparation method of cardanol polyoxyethylene ether, belong to the synthesis technical field of polyether compound in organic chemistry.
Background technology
Cardanol is a kind ofly from natural cashew nut shell oil, through modern technique, to refine and to form, contain a large amount of active single component phenol and a small amount of diphenol, can replace or Partial Replacement phenol for the manufacture of epoxy hardener, liquid phenolic resin, liquid or pulverous heat-reactive phenolic resin, purposes very extensively and environmental-protecting performance outstanding.Cardanol has the activity of petroleum phenol, and it is that monohydroxy phenols has a long hydrogeneous base carbochain above, to have wide material sources, the characteristics such as recyclability, hypotoxicity and biological degradability in position betwixt.With petroleum phenol, synthetic alkylphenol polyoxyethylene is difficult for decomposing under physical environment, can cause environmental pollution, in a lot of developed countries, is all the forbidding product.Cardanol replaces the synthetic cardanol polyoxyethylene ether class tensio-active agent of petroleum phenol, has the characteristics such as acid-and base-resisting, because biological degradability is good, is called as " green " tensio-active agent or biomass tensio-active agent.
the structure of cardanol is:
R=C
15H
31 
，
R=C
15H
29 
，
R=C
15H
27 
，
R=C
15H
25 
。
From the structure of cardanol, the meta-substituent R of cardanol is mainly the carbochain of 15 carbon, has the structure of saturated, monoene, diene and triolefin, and the position of ethylene linkage is respectively 8,11 and 14.Cardanol easily and O
2react, its unsaturated terminal chain is oxidized to superoxide.Cardanol and derivative thereof are under the naphthenic acid katalysis or through Overheating Treatment, and the side chain of himself is addition mutually also, i.e. polyaddition reaction.The phenolic hydroxyl group of cardanol easily is oxidised with air to quinones.As time goes on, the color of cardanol can deepen due to oxygenizement.
The synthetic of cardanol polyoxyethylene ether is to take cardanol as raw material, and the phenolic hydroxyl group on the cardanol phenyl ring reacts with ethyleneoxide addition under the effect of catalyzer, generates cardanol polyoxyethylene ether.In the process of synthetic cardanol polyoxyethylene ether, oxidizing reaction or polyreaction easily occur in cardanol, and unsaturated terminal chain is damaged, and two key protection rates are low, and the different mixtures that generate various ingredients of its destructiveness, affect its application performance.
The existing synthetic technology about cardanol polyoxyethylene ether, China Patent No. is: CN101941891, patent name is: a kind of method of synthetic cardanol polyoxyethylene ether, introduced a kind of method of synthetic cardanol polyoxyethylene ether, with cardanol and oxyethane, it is raw material, potassium hydroxide is catalyzer, adds the acetic acid neutralization after reaction.It is few that this method prepares the cardanol polyoxyethylene ether surfactant byproducts, and product color is good, the reaction conditions gentleness, and the prices of raw and semifnished materials are cheap, but do not mention the sfgd. of unsaturated terminal chain.
China Patent No. is: CN102206336B, and patent name is: a kind of saturated cardanol polyoxyethylene ether and preparation method thereof, introduced a kind of saturated cardanol polyoxyethylene ether and preparation method thereof, cardanol is first carried out to hydrogenation reaction; Filtration, distillation and oxyethane carry out addition reaction; Underpressure distillation after adjust pH, filtration; Perhaps cardanol is first carried out to addition reaction with oxyethane; Carry out hydrogenation reaction after adjust pH, filtration, underpressure distillation after filtering.This product does not have the unsaturated double-bond structure of mixing, and has surfactivity and it has stable use properties.But need hydrogenation reaction and pressure distillation, reactions steps is loaded down with trivial details, hydrogenation process will be used organic solvent, easily to environment.
Above two patents of invention are the smell problem of not mentioned cardanol polyoxyethylene ether all.
the content of invention
The object of the present invention is to provide a kind of preparation method of cardanol polyoxyethylene ether, made the cardanol polyoxyethylene ether product made there is odorless, thereby widened its Application Areas.
For achieving the above object, technical scheme of the present invention is:
A kind of preparation method of cardanol polyoxyethylene ether, the cardanol (being purchased from Shanghai Wujing Chemical Industry Co., Ltd.) of take is raw material, under catalyst action, after oxyethane (being purchased from three river chemical industry) polymerization reaction take place, after atlapulgite (being purchased from its scholar's wilkinite chemical industry company limited of Linan, Zhejiang) adsorption treatment, obtain cardanol polyoxyethylene ether again; The structural formula of described cardanol polyoxyethylene ether is:
R=C
15H
31 ，
R=C
15H
29 
，
R=C
15H
27 
，
R=C
15H
25 
，
n=3～25。
Comprise the steps: 1) cardanol is dropped in reactor, add catalyst reaction; 2) after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), control temperature of reaction and pressure, pass into reacting ethylene oxide, add after completion of the reaction the acetic acid neutralization; 3) in step 2) filter after adding the atlapulgite adsorption treatment in the material that obtains after finishing of reaction, make cardanol polyoxyethylene ether.
Described step 1) is specially cardanol is dropped in reactor, and controlling temperature is 20～30 ℃, adds catalyzer in 30min, after catalyzer adds, then reacts 30min.
Described catalyzer adopts one or both in potassium, sodium; The add-on of described catalyzer and the weight percent of cardanol polyoxyethylene ether are 0.2～0.4%.
Described step 2) be specially after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), controlling temperature of reaction is 90～110 ℃; Reaction pressure is 0.2～0.4MPa, passes into oxyethane, and the reaction times is 5～10h, adds after completion of the reaction the acetic acid neutralization.
Described step 3) is specially in step 2) add atlapulgite to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 1～2 hour, makes cardanol polyoxyethylene ether.
The add-on of described atlapulgite and the weight percent of cardanol polyoxyethylene ether are 1.0～3.0%.
The invention has the beneficial effects as follows: the preparation method of a kind of cardanol polyoxyethylene ether of the present invention, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present invention has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present invention, have the characteristics such as odorless;
2. by the present invention, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Embodiment
In the embodiment of the present invention, cardanol used is commercial product, carries out " People's Republic of China's chemical industry standard " HG/T4118-2009.
Embodiment 1
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment: 1) 700 parts of cardanols are dropped in reactor, controlling temperature is 20～30 ℃, adds 3.0 parts, catalyst metal sodium in 30min, after catalyzer adds, then reacts 30min.2), after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), be warming up to 95 ℃, pass into 308 parts of oxyethane, controlling temperature of reaction is 95～100 ℃, and reaction pressure is 0.2MPa, reaction times is 5h, adds after completion of the reaction the acetic acid neutralization.3) in step 2) add 10 parts of atlapulgites to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 2 hours, makes cardanol polyoxyethylene ether.
The cardanol polyoxyethylene ether odorless made by the present embodiment.
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present embodiment has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present embodiment, have the characteristics such as odorless;
2. by the present embodiment, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Embodiment 2
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment: 1) 450 parts of cardanols are dropped in reactor, controlling temperature is 20～30 ℃, adds 2.1 parts, catalyst metal potassium in 30min, after catalyzer adds, then reacts 30min.2), after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), be warming up to 100 ℃, pass into 590 parts of oxyethane, controlling temperature of reaction is 100～105 ℃, and reaction pressure is 0.25MPa, reaction times is 8h, adds after completion of the reaction the acetic acid neutralization.3) in step 2) add 15 parts of atlapulgites to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 1.5 hours, makes cardanol polyoxyethylene ether.
The cardanol polyoxyethylene ether odorless made by the present embodiment.
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present invention has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present embodiment, have the characteristics such as odorless;
2. by the present embodiment, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Embodiment 3
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment: 1) 330 parts of cardanols are dropped in reactor, controlling temperature is 20～30 ℃, adds 4.0 parts, catalyst metal potassium in 30min, after catalyzer adds, then reacts 30min.2) after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), be warming up to 90 ℃, pass into 673 parts of oxyethane, controlling temperature of reaction is 90～95 ℃; Reaction pressure is 0.35MPa, and the reaction times is 10h, adds after completion of the reaction the acetic acid neutralization.3) in step 2) add 20 parts of atlapulgites to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 1.5 hours, makes cardanol polyoxyethylene ether.
The cardanol polyoxyethylene ether odorless made by the present embodiment.
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present embodiment has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present embodiment, have the characteristics such as odorless;
2. by the present embodiment, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Embodiment 4
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment: 1) 250 parts of cardanols are dropped in reactor, controlling temperature is 20～30 ℃, add 2.5 parts of catalyst metal potassium and potassium metals (weight ratio of sodium Metal 99.5 and potassium metal is 1:1) in 30min, after catalyzer adds, then react 30min.2) after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), be warming up to 95 ℃, pass into 740 parts of oxyethane, controlling temperature of reaction is 95～100 ℃; Reaction pressure is 0.30MPa, and the reaction times is 9h, adds after completion of the reaction the acetic acid neutralization.3) in step 2) add 30 parts of atlapulgites to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 1 hour, makes cardanol polyoxyethylene ether.
The cardanol polyoxyethylene ether odorless made by the present embodiment.
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present embodiment has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present embodiment, have the characteristics such as odorless;
2. by the present embodiment, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Embodiment 5
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment: 1) 220 parts of cardanols are dropped in reactor, controlling temperature is 20～30 ℃, adds 3.5 parts, catalyst metal sodium in 30min, after catalyzer adds, then reacts 30min.2) after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), be warming up to 105 ℃, pass into 800 parts of oxyethane, controlling temperature of reaction is 105～110 ℃; Reaction pressure is 0.4MPa, and the reaction times is 6h, adds after completion of the reaction the acetic acid neutralization.3) in step 2) add 23 parts of atlapulgites to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, filters after being incubated 1 hour, makes cardanol polyoxyethylene ether.
The cardanol polyoxyethylene ether odorless made by the present embodiment.
The preparation method of a kind of cardanol polyoxyethylene ether of the present embodiment, the stink of use atlapulgite adsorption treatment cardanol polyoxyethylene ether.Simultaneously, the add-on by the temperature of reaction to cardanol polyoxyethylene ether and reaction pressure, catalyzer is in optimized selection, and technique is reasonable, simple to operate.
Compared with prior art, the present embodiment has following outstanding advantages and positively effect:
1. the cardanol polyoxyethylene ether obtained by the present embodiment, have the characteristics such as odorless;
2. by the present embodiment, obtain cardanol polyoxyethylene ether to have quality good, the characteristics that application performance is stable, and can control the hydrophilic hydrophobic balance value of nonionogenic tenside HLB according to the adduct number of processing requirement adjustment ring oxidative ethane, thereby can be used as emulsifying agent, wetting agent, washing composition, solubilizing agent etc.
Claims (7)
1. the preparation method of a cardanol polyoxyethylene ether, is characterized in that: take cardanol as raw material, under catalyst action, after the oxyethane polymerization reaction take place, then, after the atlapulgite adsorption treatment, obtain cardanol polyoxyethylene ether; The structural formula of described cardanol polyoxyethylene ether is:
,
R=C
15H
31 ，
R=C
15H
29 ，
R=C
15H
27 ，
R=C
15H
25 
，
n=3～25。
2. the preparation method of cardanol polyoxyethylene ether as claimed in claim 1, is characterized in that comprising the steps: 1) cardanol is dropped in reactor, add catalyst reaction; 2) after step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), control temperature of reaction and pressure, pass into reacting ethylene oxide, add after completion of the reaction the acetic acid neutralization; 3) in step 2) filter after adding the atlapulgite adsorption treatment in the material that obtains after finishing of reaction, make cardanol polyoxyethylene ether.
3. the preparation method of cardanol polyoxyethylene ether as claimed in claim 2, it is characterized in that: described step 1) is specially cardanol is dropped in reactor, and controlling temperature is 20～30 ℃, adds catalyzer in 30min, after catalyzer adds, then react 30min.
4. as the preparation method of claim 1 or 2 or 3 described cardanol polyoxyethylene ethers, it is characterized in that: described catalyzer adopts one or both in potassium, sodium; The add-on of described catalyzer and the weight percent of cardanol polyoxyethylene ether are 0.2～0.4%.
5. the preparation method of cardanol polyoxyethylene ether as claimed in claim 2, it is characterized in that: described step 2) be specially after the step 1) reaction finishes, after adopting nitrogen replacement to go out the air in the reactor of step 1), controlling temperature of reaction is 90～110 ℃; Reaction pressure is 0.2～0.4MPa, passes into oxyethane, and the reaction times is 5～10h, adds after completion of the reaction the acetic acid neutralization.
6. the preparation method of cardanol polyoxyethylene ether as claimed in claim 2, it is characterized in that: described step 3) is specially in step 2) add atlapulgite to carry out adsorption treatment in the material that obtains after finishing of reaction, controlling temperature is 80 ℃～100 ℃, be incubated after 1～2 hour and filter, make cardanol polyoxyethylene ether.
7. as the preparation method of claim 1 or 2 or 6 described cardanol polyoxyethylene ethers, it is characterized in that: the add-on of described atlapulgite and the weight percent of cardanol polyoxyethylene ether are 1.0～3.0%.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106750247A (en) * | 2016-12-28 | 2017-05-31 | 三江化工有限公司 | A kind of preparation method of low free alcohol AEO |
| CN106800648A (en) * | 2016-12-28 | 2017-06-06 | 三江化工有限公司 | A kind of preparation method of NPE expoxy propane end-blocking |
| CN108707406A (en) * | 2018-06-15 | 2018-10-26 | 成都澳贝龙科技发展有限公司 | A kind of baking-type aqueous double-component polyurethane varnish and its application method and purposes |
| CN109158050A (en) * | 2018-09-10 | 2019-01-08 | 上海邦高化学有限公司 | Cashew nut phenolic anion-nonionic surfactant and the preparation method and application thereof |
| CN110483300A (en) * | 2019-09-12 | 2019-11-22 | 陕西科技大学 | A kind of acrylic acid anacardol polyoxyethylene ester and preparation method thereof |
| CN110982060A (en) * | 2019-12-24 | 2020-04-10 | 上海拓径新材料科技股份有限公司 | Amine-terminated polyether compound containing cardanol derivative, and preparation method and application thereof |
| CN111777740A (en) * | 2020-07-23 | 2020-10-16 | 南通星辰合成材料有限公司 | Cardanol polyether modified ABA type waterborne epoxy resin and preparation method thereof |
| CN113087894A (en) * | 2021-04-01 | 2021-07-09 | 上海邦高化学有限公司 | Cardanol polyoxyethylene ether, preparation method and application thereof |
| CN114349632A (en) * | 2022-01-17 | 2022-04-15 | 艾茵化学(深圳)有限公司 | Cardanol ether rosin carboxylic acid anionic surfactant and preparation method thereof |
| CN114805784A (en) * | 2022-02-24 | 2022-07-29 | 南京林业大学 | Preparation method of high-plasticization and anti-migration cardanol-based plasticizer |
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| CN106750247A (en) * | 2016-12-28 | 2017-05-31 | 三江化工有限公司 | A kind of preparation method of low free alcohol AEO |
| CN106800648A (en) * | 2016-12-28 | 2017-06-06 | 三江化工有限公司 | A kind of preparation method of NPE expoxy propane end-blocking |
| CN106750247B (en) * | 2016-12-28 | 2018-03-06 | 三江化工有限公司 | A kind of preparation method of low free alcohol AEO |
| CN106800648B (en) * | 2016-12-28 | 2018-06-08 | 三江化工有限公司 | A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end |
| CN108707406A (en) * | 2018-06-15 | 2018-10-26 | 成都澳贝龙科技发展有限公司 | A kind of baking-type aqueous double-component polyurethane varnish and its application method and purposes |
| CN109158050A (en) * | 2018-09-10 | 2019-01-08 | 上海邦高化学有限公司 | Cashew nut phenolic anion-nonionic surfactant and the preparation method and application thereof |
| CN110483300A (en) * | 2019-09-12 | 2019-11-22 | 陕西科技大学 | A kind of acrylic acid anacardol polyoxyethylene ester and preparation method thereof |
| CN110982060A (en) * | 2019-12-24 | 2020-04-10 | 上海拓径新材料科技股份有限公司 | Amine-terminated polyether compound containing cardanol derivative, and preparation method and application thereof |
| CN111777740A (en) * | 2020-07-23 | 2020-10-16 | 南通星辰合成材料有限公司 | Cardanol polyether modified ABA type waterborne epoxy resin and preparation method thereof |
| CN111777740B (en) * | 2020-07-23 | 2023-02-28 | 南通星辰合成材料有限公司 | Cardanol polyether modified ABA type waterborne epoxy resin and preparation method thereof |
| CN113087894A (en) * | 2021-04-01 | 2021-07-09 | 上海邦高化学有限公司 | Cardanol polyoxyethylene ether, preparation method and application thereof |
| CN113087894B (en) * | 2021-04-01 | 2022-10-21 | 上海邦高化学有限公司 | Cardanol polyoxyethylene ether, preparation method and application thereof |
| CN114349632A (en) * | 2022-01-17 | 2022-04-15 | 艾茵化学(深圳)有限公司 | Cardanol ether rosin carboxylic acid anionic surfactant and preparation method thereof |
| CN114805784A (en) * | 2022-02-24 | 2022-07-29 | 南京林业大学 | Preparation method of high-plasticization and anti-migration cardanol-based plasticizer |
| CN114805784B (en) * | 2022-02-24 | 2023-09-12 | 南京林业大学 | Preparation method of high-plasticization and migration-resistant cardanol-based plasticizer |
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