CN106800648B - A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end - Google Patents
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end Download PDFInfo
- Publication number
- CN106800648B CN106800648B CN201611238274.XA CN201611238274A CN106800648B CN 106800648 B CN106800648 B CN 106800648B CN 201611238274 A CN201611238274 A CN 201611238274A CN 106800648 B CN106800648 B CN 106800648B
- Authority
- CN
- China
- Prior art keywords
- polyoxyethylene ether
- nonylphenol polyoxyethylene
- propylene oxide
- sealing end
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3328—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof heterocyclic
-
- 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
-
- 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
-
- 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
- C08G65/2612—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 aromatic or arylaliphatic hydroxyl groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of preparation methods of the nonylphenol polyoxyethylene ether by propylene oxide sealing end, it includes the following steps：1）Using nonyl phenol as initiator, under the action of basic catalyst and ethylene oxide carries out addition reaction, and nonylphenol polyoxyethylene ether is made；2）By step 1）Obtained nonylphenol polyoxyethylene ether cooling, adds in propene carbonate and is reacted, neutralized after reaction with acetic acid, and nonylphenol polyoxyethylene ether propylene oxide sealing end is made.The present invention uses traditional basic catalyst, and raw material is simple and easy to get, at low cost, simple production process, and production efficiency is high, and the foam blocked by nonylphenol polyoxyethylene ether propylene oxide prepared by this method is low, ending ratio is high.
Description
Technical field
The invention belongs to nonionic surfactant synthesis technical fields, and in particular to a kind of nonyl blocked by propylene oxide
The preparation method of base phenol polyethenoxy ether.
Background technology
Nonylphenol polyoxyethylene ether is a kind of highly important nonionic surfactant, has excellent decontamination, wetting
With emulsification etc. performances, gather in industry cleaning link, textile printing and dyeing, papermaking, leather chemical industry, preparation medium, oilfield additive, pesticide, lotion
The industrial circles such as conjunction have a wide range of applications.
Meanwhile nonylphenol polyoxyethylene ether is the high nonionic surfactant of a class A foam A, in industry cleaning link and weaving
The industrial circles such as printing and dyeing can generate a large amount of foam, make troubles to execute-in-place.The polyoxyethylene nonyl phenyl blocked by propylene oxide
Vinethene reduces sealing end product due to introducing the propylene oxide with branch in nonylphenol polyoxyethylene ether molecular end
Foam uses requiring low foaming industrial circle that can substitute nonylphenol polyoxyethylene ether, solves high foam to production operation
The inconvenience brought.
Invention content
For the above-mentioned problems in the prior art, the purpose of the present invention is to provide a kind of low foam, ending ratio are high
By propylene oxide sealing end nonylphenol polyoxyethylene ether preparation method.
A kind of preparation method of described nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that including with
Lower step：
1）Using nonyl phenol as initiator, under the action of basic catalyst and ethylene oxide carries out addition reaction, and nonyl is made
Base phenol polyethenoxy ether；
2）By step 1）Obtained nonylphenol polyoxyethylene ether cooling, adds in propene carbonate and is reacted, reaction terminates
It is neutralized afterwards with acetic acid, the nonylphenol polyoxyethylene ether blocked by propylene oxide is made,
Its synthetic route is as follows：
,
Wherein, m=1~15.
The preparation method of a kind of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that alkalinity is urged
Agent is any one or more than one mixtures in potassium hydroxide, sodium hydroxide, sodium methoxide.
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that step 1）
Reaction temperature for 100~180 DEG C, the reaction time is 2~5 hours.
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that step 1）
Reaction temperature for 100~180 DEG C, the reaction time is 2~5 hours.
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that step 1）
Nonyl phenol and ethylene oxide molar ratio be 1：1-15.
The preparation method of a kind of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that alkalinity is urged
The addition of agent is nonyl phenol and the 0.4~0.8% of ethylene oxide gross mass.
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that step 2）
Reaction temperature for 60~80 DEG C, the reaction time is 1~3 hour.
A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that nonyl phenol
Molar ratio with propene carbonate is 1：1.
Using the above method, has the following advantages the present invention：
1）The present invention is simple using traditional basic catalyst, such as potassium hydroxide, sodium hydroxide, sodium methoxide, raw material
It is easy to get, at low cost, simple production process, production efficiency height；
2）The present invention is prepared by using the preparation method of the nonylphenol polyoxyethylene ether by propylene oxide sealing end of restriction
The nonylphenol polyoxyethylene ether by propylene oxide sealing end foam is low, ending ratio is high.
Specific embodiment
1 Nonyl pheno of embodiment（7）The preparation of ether ring Ethylene Oxide sealing end
1.5mol is added in pressure reaction still（330g）Nonyl phenol and 4.75g sodium methoxide catalysts, by ethylene oxide meter
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 180 DEG C, is passed through 10.5mol (462g) ring
Oxidative ethane has led to for 2.5 hours, and the reaction was continued 0.5 hour.Then, slow cooling adds in 1.5mol to 70 DEG C（153g）Carbonic acid third
Enester, opens pressure-relief valve, and pressure-relief valve absorbs slot by pipeline and 40% sodium hydrate aqueous solution and connects, reacts 2 hours.Reaction
After, cooling adds in acetic acid and neutralizes, and blowing obtains Nonyl pheno（7）Ether ring Ethylene Oxide blocks.
2 Nonyl pheno of embodiment（11）The preparation of ether ring Ethylene Oxide sealing end
0.75mol is added in pressure reaction still（165g）Nonyl phenol and 4.22g potassium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 120 DEG C, is passed through 8.25mol (363g)
Ethylene oxide has led to for 3.5 hours, and the reaction was continued 0.5 hour.Then, slow cooling adds in 0.75mol to 60 DEG C（76.5g）Carbon
Acid propylene ester opens pressure-relief valve, and pressure-relief valve absorbs slot by pipeline and 40% sodium hydrate aqueous solution and connects, and reaction 1.5 is small
When.After completion of the reaction, it cools down, adds in acetic acid and neutralize, blowing obtains Nonyl pheno（11）Ether ring Ethylene Oxide blocks.
3 Nonyl pheno of embodiment（1）The preparation of ether ring Ethylene Oxide sealing end
1.0mol is added in pressure reaction still（220g）Nonyl phenol and 1.06g sodium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 100 DEG C, is passed through 1.0mol (44g) ring
Oxidative ethane has led to for 1.5 hours, and the reaction was continued 0.5 hour.Then, slow cooling adds in 1.0mol to 80 DEG C（102g）Carbonic acid third
Enester, opens pressure-relief valve, and pressure-relief valve absorbs slot by pipeline and 40% sodium hydrate aqueous solution and connects, reacts 3 hours.Reaction
After, cooling adds in acetic acid and neutralizes, and blowing obtains Nonyl pheno（1）Ether ring Ethylene Oxide blocks.
4 Nonyl pheno of embodiment（15）The preparation of ether ring Ethylene Oxide sealing end
0.5mol is added in pressure reaction still（110g）Nonyl phenol and 3.08g potassium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 140 DEG C, is passed through 7.5mol (330g) ring
Oxidative ethane has led to for 4.5 hours, and the reaction was continued 0.5 hour.Then, slow cooling adds in 0.5mol to 75 DEG C（51g）Carbonic acid third
Enester, opens pressure-relief valve, and pressure-relief valve absorbs slot by pipeline and 40% sodium hydrate aqueous solution and connects, reacts 1 hour.Reaction
After, cooling adds in acetic acid and neutralizes, and blowing obtains Nonyl pheno（15）Ether ring Ethylene Oxide blocks.
5 Nonyl pheno of embodiment（4）The preparation of ether ring Ethylene Oxide sealing end
1.25mol is added in pressure reaction still（275g）Nonyl phenol and 2.48g sodium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 160 DEG C, is passed through 5.0mol (220g) ring
Oxidative ethane has led to for 3.5 hours, and the reaction was continued 0.5 hour.Then, slow cooling adds in 1.25mol to 65 DEG C（127.5g）Carbon
Acid propylene ester opens pressure-relief valve, and pressure-relief valve absorbs slot by pipeline and 40% sodium hydrate aqueous solution and connects, and reaction 2.5 is small
When.After completion of the reaction, it cools down, adds in acetic acid and neutralize, blowing obtains Nonyl pheno（4）Ether ring Ethylene Oxide blocks.
1 Nonyl pheno of comparative example（15）The preparation of ether
0.5mol is added in pressure reaction still（110g）Nonyl phenol and 3.08g potassium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 140 DEG C, is passed through 7.5mol (330g) ring
Oxidative ethane has led to for 4.5 hours, and the reaction was continued 0.5 hour.After completion of the reaction, it cools down, release, adds in acetic acid and neutralize, blowing.
2 Nonyl pheno of comparative example（1）The preparation of ether
1.0mol is added in pressure reaction still（220g）Nonyl phenol and 1.06g sodium hydroxide catalysts, by ethylene oxide
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 100 DEG C, is passed through 1.0mol (44g) ring
Oxidative ethane has led to for 1.5 hours, and the reaction was continued 0.5 hour.After completion of the reaction, it cools down, release, adds in acetic acid and neutralize, blowing.
3 Nonyl pheno of comparative example（7）The preparation of ether
1.5mol is added in pressure reaction still（330g）Nonyl phenol and 4.75g sodium methoxide catalysts, by ethylene oxide meter
Measuring tank is connect with autoclave pressure.Air 3 times in kettle are replaced with nitrogen, treats that kettle temperature rises to 180 DEG C, is passed through 10.5mol (462g) ring
Oxidative ethane has led to for 2.5 hours, and the reaction was continued 0.5 hour.After completion of the reaction, it cools down, release, adds in acetic acid and neutralize, blowing.
The prepared nonylphenol polyoxyethylene ether and comparative example 1~3 by propylene oxide sealing end in above-described embodiment 1~5
In prepared nonylphenol polyoxyethylene ether after tested, the following table of specific targets：
| Serial number | Molecule ethylene oxide number | Molecule oxypropylene number | Foam height（mm） |
| Embodiment 1 | 7 | 1 | 13 |
| Embodiment 2 | 11 | 1 | 19 |
| Embodiment 3 | 1 | 1 | 4 |
| Embodiment 4 | 15 | 1 | 27 |
| Embodiment 5 | 4 | 1 | 9 |
| Comparative example 1 | 15 | 0 | 38 |
| Comparative example 2 | 1 | 0 | 9 |
| Comparative example 3 | 7 | 0 | 26 |
Foam test method（25 DEG C of test temperature）：Prepare mass ratio be 1% aqueous surfactant solution, take 10mL in
In the tool plug graduated cylinder of one 50mL.Cap acutely rocks 10 seconds up and down, stands, and reads foam height（The scale that foam reaches
Subtract the scale of liquid level）.
As can be drawn from Table 1, the nonylphenol polyoxyethylene ether through being blocked made from the method for the present invention by propylene oxide, it is and normal
Nonylphenol polyoxyethylene ether made from rule method is compared, and foam height is substantially reduced, and ending ratio is high.
Claims (7)
1. the preparation method of a kind of nonylphenol polyoxyethylene ether by propylene oxide sealing end, it is characterised in that include the following steps：
1）Using nonyl phenol as initiator, under the action of basic catalyst and ethylene oxide carries out addition reaction, and reaction temperature is
100~180 DEG C, nonylphenol polyoxyethylene ether is made；
2）By step 1）Obtained nonylphenol polyoxyethylene ether cooling, adds in propene carbonate and is reacted, reaction temperature 60
It~80 DEG C, is neutralized after reaction with acetic acid, the nonylphenol polyoxyethylene ether blocked by propylene oxide is made,
Its synthetic route is as follows：
,
Wherein, m=1~15.
2. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is basic catalyst for any one in potassium hydroxide, sodium hydroxide, sodium methoxide or more than one mixtures.
3. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is step 1）Reaction time be 2~5 hours.
4. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is step 1）Nonyl phenol and ethylene oxide molar ratio be 1：1-15.
5. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is that the addition of basic catalyst is the 0.4~0.8% of nonyl phenol and ethylene oxide gross mass.
6. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is step 2）Reaction time be 1~3 hour.
7. a kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end according to claim 1, special
Sign is that the molar ratio of nonyl phenol and propene carbonate is 1：1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611238274.XA CN106800648B (en) | 2016-12-28 | 2016-12-28 | A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611238274.XA CN106800648B (en) | 2016-12-28 | 2016-12-28 | A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106800648A CN106800648A (en) | 2017-06-06 |
| CN106800648B true CN106800648B (en) | 2018-06-08 |
Family
ID=58984200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611238274.XA Active CN106800648B (en) | 2016-12-28 | 2016-12-28 | A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106800648B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN109627149A (en) * | 2018-12-14 | 2019-04-16 | 药大制药有限公司 | A method of preparing the nonoxinol without ethylene oxide |
| CN114249636A (en) * | 2021-11-26 | 2022-03-29 | 泰兴市凌飞化学科技有限公司 | Preparation method of dinonylphenol polyoxyethylene ether as component of heavy-duty oil stain cleaning agent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0352838A (en) * | 1989-07-20 | 1991-03-07 | Mitsui Petrochem Ind Ltd | Production of beta-hydroxyalkyl aryl ether |
| CN1332712A (en) * | 1998-12-10 | 2002-01-23 | 卡尔多利特公司 | Cardanol derivative and method of making cardanol derivative |
| 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 |
| CN105793225A (en) * | 2013-12-10 | 2016-07-20 | 巴斯夫欧洲公司 | Alkylene oxide-free methods for producing polyetherols |
-
2016
- 2016-12-28 CN CN201611238274.XA patent/CN106800648B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0352838A (en) * | 1989-07-20 | 1991-03-07 | Mitsui Petrochem Ind Ltd | Production of beta-hydroxyalkyl aryl ether |
| CN1332712A (en) * | 1998-12-10 | 2002-01-23 | 卡尔多利特公司 | Cardanol derivative and method of making cardanol derivative |
| 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 |
| CN105793225A (en) * | 2013-12-10 | 2016-07-20 | 巴斯夫欧洲公司 | Alkylene oxide-free methods for producing polyetherols |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106800648A (en) | 2017-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106800648B (en) | A kind of preparation method of nonylphenol polyoxyethylene ether by propylene oxide sealing end | |
| CN103387486B (en) | A kind of preparation method of isomeric alcohol polyoxypropylene polyoxyethylene ether | |
| CN101690877B (en) | Pentadecyl phenol polyethenoxy ether strong biodegradable surfactant | |
| CN106590563A (en) | Salt-tolerant drainage gas recovery foam scrubbing agent composition and preparation method and application thereof | |
| CN105778076B (en) | A kind of polyether amine compound and preparation method and application | |
| AR069725A1 (en) | PROCESS TO PREPARE A COMPOSITION OF ALCOXYLATE AND A COMPOSITION OF ALCOXYLATE | |
| CN103145568A (en) | Cardanol cationoid quaternary ammonium salt and preparation method thereof | |
| CN107537185A (en) | A kind of self-emulsifying type defoamer and preparation method thereof | |
| CN106590583A (en) | Hypersalinity-resistant foam discharging agent composition for drainage gas production as well as preparation method and application thereof | |
| CN106590574A (en) | Hypersalinity resistant foam scrubbing agent composition used for drainage gas recovery and preparation method and application thereof | |
| CN105567205B (en) | A kind of synthetic method of oil displacement agent and mustard base oxidation amine surfactants | |
| CN1965014B (en) | Process of preparing odor-lean polyether polyol | |
| CN106750247B (en) | A kind of preparation method of low free alcohol AEO | |
| EP2928862A1 (en) | Process for preparing alkoxylated alcohols | |
| CN111087608B (en) | Oil-displacing surfactant and composition of alkyl phenol polyether bisbenzenesulfonate, and preparation method and application thereof | |
| CN114437335A (en) | Synthesis method of fatty alcohol polyether defoamer with wide molecular weight distribution | |
| JP2015044911A (en) | Crumb-dewatering-process biting-characteristic improver and method for producing rubber-like polymer | |
| JP2017504584A (en) | Process for liberating alkylene oxides to produce polyetherols | |
| CN106633026A (en) | Synthesis method of low-foam water-soluble high molecular polyether | |
| JP6492468B2 (en) | Polyalkylene oxide having excellent storage stability and process for producing the same | |
| CN115028826A (en) | Diamino polyether surfactant and preparation method thereof | |
| CN111087601A (en) | Surfactant and composition for oil extraction and preparation method thereof | |
| CN108440749A (en) | Flame retardant polyether polyol and preparation method thereof | |
| CN110776431B (en) | Efficient anti-swelling agent and preparation method thereof | |
| JP2013082854A (en) | Anionic surfactant composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |