CN106187714A - Alkylbenzene methanol polyoxyethylene ether and preparation method thereof - Google Patents
Alkylbenzene methanol polyoxyethylene ether and preparation method thereof Download PDFInfo
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- CN106187714A CN106187714A CN201610569768.XA CN201610569768A CN106187714A CN 106187714 A CN106187714 A CN 106187714A CN 201610569768 A CN201610569768 A CN 201610569768A CN 106187714 A CN106187714 A CN 106187714A
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- C—CHEMISTRY; METALLURGY
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- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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Abstract
This application discloses a kind of alkylbenzene methanol polyoxyethylene ether and preparation method thereof, the molecular structure of alkylbenzene methanol polyoxyethylene ether includes hydrophobic group and hydrophilic group, and molecular structural formula is as follows:
Description
Technical field
The disclosure relates generally to pluronic polymer synthesis technical field, is specifically related to emulsifying agent, particularly relates to alkylbenzene first
Polyoxyethylenated alcohol and preparation method thereof.
Background technology
Emulsifying agent containing alkylphenol polyoxyethylene compounds (be called for short APEO) structure has good moistening, oozes
Thoroughly, emulsifying, dispersion, solubilising and cleaning function, the emulsifying agent being mainly used as on pesticide, textile auxiliary, defoamer, detergent, point
Powder, emulsifying agent, softening agent, dyeing assistant, fibre finishing, crude oil demulsifier etc., be widely used in detergent, personal nursing
The industries such as article of everyday use, weaving, papermaking, oil, metallurgy, pesticide, pharmacy, printing, synthetic rubber, water-based emulsion, plastics.In APEO
Account for 80～85% including NPE (be called for short NPEO), OPEO (being called for short OPEO) account for 15% with
On, dodecyl phenol polyethenoxy ether (being called for short DPEO) and Dinonylphenol Polyoxyethylene Ether (being called for short DNPEO) respectively account for 1%.The whole world
The yield of emulsifying agent (calculating by 100% effective content) anion 3,600,000 tons, nonionic 3,650,000 tons, both sexes 180,000 tons, sun from
Son 760,000 tons, wherein alkylphenol polyoxyethylene yearly consumption is for reaching more than 1,000,000 tons, and wherein more than 80% is polyoxyethylene nonyl phenyl second
Alkene ether.
The harm of ecological environment is studied and is proved by APEO widely: mammal and aquatile are had biology
Toxicity and carcinogenecity；Biological degradability is slow, and its biological degradation rate is less than 9%；There is similar estrogen effect, people can be endangered
The chemical substance of the normal hormone secretion of body, i.e. " female effect " and physiological aberration；The by-product produced in process of manufacture
Product dioxanes is serious carcinogen.Due to presented above go out problem, more American-European-Japanese countries just system before 1976
Determine regulation to limit and produce and use APEO, made as European Union just limited in 1998 in the detergent of personal consumption, abluent
With APEO, within 2005, limit in clothing and textile and use APEO." environmental mark produces Chinese environmental protection standard HJ2537 2014
Product technology require water paint " in clear stipulaties: the material requirement that must not artificially add, including without seven class materials such as APEO.
For environmental protection and the disabling problem of APEO, universal best solution is that different purposes is used different substitute products,
These substitute products include AEO fatty alcohol-polyoxyethylene ether, isomeric alcohol polyethenoxy ether, AES, SAS, AOS, APG, poly alkyl alcohol
Oxygen vinyl Ether phosphate ester, succinate sodium salt etc. or its compound and substitute APEO product.
The most domestic technology without APEO is concentrated mainly on fatty alcohol-polyoxyethylene ether and derivant thereof, and representative products has the moon
Cinnamic alcohol polyoxyethylene ether, polyoxyethylene lauryl ether ammonium sulfate, polyoxyethylene lauryl ether ammonium phosphate, isomerous tridecanol polyoxy second
Alkene ether, isomerous tridecanol polyoxyethylene ether ammonium sulfate, isomerous tridecanol polyoxyethylene ether ammonium phosphate, lauryl alcohol or isomerous tridecanol
Polyoxyethylene ether disodium succinate salt etc..Although the polyoxyethylene ether system emulsifying agent of aliphatic alcohols overcomes the shortcoming of alkyl phenol,
But its emulsifying capacity, sound of taking a group photo polymeric colloidal polyurea are relatively big with differing of alkyl phenol, the performance of emulsion and alkyl phenol system
Emulsion ratio also differs bigger；This is because the carbon number of fatty alcohol is mostly more than 12 in fatty alcohol-polyoxyethylene ether, crystallinity
By force, critical micelle concentration improve, consumption improve, emulsifying capacity decline, and due to consumption improve, the resistance to water of emulsion film under
Fall；On the other hand, owing to the wettability of fatty alcohol-polyoxyethylene ether is not as alkylphenol polyoxyethylene, send out after emulsion paint
The color developing of existing film is substantially reduced.So, exploitation one is similar to alkyl phenol this band benzene ring structure and does not the most have alkyl phenol
The emulsifying agent of toxicity substitutes the emulsifying agent of alkyl phenol structure and has become as study hotspot and the difficult point of those skilled in the art.
Summary of the invention
In view of drawbacks described above of the prior art or deficiency, it is desirable to provide a kind of alkylbenzene methanol polyoxyethylene without APEO
Ether.
First aspect, the present invention provides a kind of alkylbenzene methanol polyoxyethylene ether, dividing of alkylbenzene methanol polyoxyethylene ether
Minor structure includes hydrophobic group and hydrophilic group, and molecular structural formula is as follows:
Wherein, the R in molecular formula is alkyl, n=3～50；Further n=4～40.
Second aspect, the present invention also provides for the preparation method of a kind of alkylbenzene methanol polyoxyethylene ether, comprises the following steps:
A, in a kettle., adds alkylbenzene, paraformaldehyde, sodium bromide, reacts 6 in 70 DEG C under acidic catalyst effect
～8h, it is subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains alkyl bromide
Benzyl；
B, in a kettle., adds alkyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, protects at this temperature
Hold back flow reaction 2h, obtain alkylbenzene methanol；
C, add alkylbenzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；It has been dehydrated
Finish, after being passed through nitrogen displacement, mol ratio 1:(3～50 by alkylbenzene methanol/oxirane) it is slowly introducing oxirane, control
Reaction temperature processed 120～140 DEG C, pressure is less than 0.2mPa；
D, detection, when stopping being passed through oxirane after the degree of polymerization that reaction reaches required, are reacted into termination phase, cold
But it is cooled to 120 DEG C, adds acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, filters and packages, obtain alkylbenzene
Methanol polyoxyethylene ether.
The alkylbenzene methanol polyoxyethylene ether that the present invention provides without APEO, have good moistening, infiltration, emulsifying, point
Dissipate, solubilising and cleaning function, can be used as emulsifying agent, textile auxiliary, detergent, dispersant, softening agent, crude oil demulsifier etc., complete
Complete substitute alkylphenol polyoxyethylene emulsifying agent, be widely used in detergent, personal care articles, weaving, papermaking, oil, pesticide,
The industries such as pharmacy, printing, synthetic rubber, water-based emulsion, coating, ink, glue, plastics.
Detailed description of the invention
Below in conjunction with embodiment, the application is described in further detail.It is understood that tool described herein
Body embodiment is used only for explaining related invention, rather than the restriction to this invention.
It should be noted that in the case of not conflicting, the embodiment in the application and the feature in embodiment can phases
Combination mutually.
The synthesis mechanism of the alkylbenzene methanol polyoxyethylene ether that the present invention provides is shown below:
Wherein, the R in molecular formula is alkyl, n=3～50.
Alkylbenzene methanol polyoxyethylene ether can be as a kind of novel anionic and nonionic type emulsifying agent without APEO.
It is illustrated the alkylbenzene methanol polyoxyethylene ether that the present invention provides below by following example, specific as follows:
Embodiment 1
A kind of nonyl benzene methanol polyoxyethylene ether-4 emulsifying agent without APEO, its preparation method is as follows:
Step a, in a kettle., adds nonyl benzene, paraformaldehyde, sodium bromide, anti-in 70 DEG C under acid catalyst effect
Answering 6～8h, be subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains nonyl
Bromobenzyl；
Step b, in a kettle., adds nonyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, in this temperature
Under maintain the reflux for react 2h, obtain nonyl benzene methanol；
Step c, put into nonyl benzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；De-
Water is complete, after being passed through nitrogen displacement, presses the mol ratio 1/ (4～5) to nonyl benzene methanol/oxirane and is slowly introducing epoxy second
Alkane, control reaction temperature 120～140 DEG C, pressure is less than 0.2MPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 4, stop being passed through oxirane, react into
Enter termination phase, cool to 120 DEG C, add acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, bag filter
Dress, obtains nonyl benzene methanol polyoxyethylene ether-4.
Embodiment 2
A kind of nonyl benzene methanol polyoxyethylene ether-10 emulsifying agent without APEO, its preparation method is as follows:
Step a, in a kettle., adds nonyl benzene, paraformaldehyde, sodium bromide, anti-in 70 DEG C under acid catalyst effect
Answering 6～8h, be subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains nonyl
Bromobenzyl；
Step b, in a kettle., adds nonyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, in this temperature
Under maintain the reflux for react 2h, obtain nonyl benzene methanol；
Step c, put into nonyl benzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；De-
Water is complete, after being passed through nitrogen displacement, presses the mol ratio 1/ (10～11) to nonyl benzene methanol/oxirane and is slowly introducing epoxy second
Alkane, control reaction temperature 120～140 DEG C, pressure is less than 0.2MPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 10, stop being passed through oxirane, react into
Enter termination phase, cool to 120 DEG C, add acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, bag filter
Dress, obtains nonyl benzene methanol polyoxyethylene ether-10.
Embodiment 3
A kind of nonyl benzene methanol polyoxyethylene ether-15 emulsifying agent without APEO, its preparation method is as follows:
Step a, in a kettle., adds nonyl benzene, paraformaldehyde, sodium bromide, anti-in 70 DEG C under acid catalyst effect
Answering 6～8h, be subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains nonyl
Bromobenzyl；
Step b, in a kettle., adds nonyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, in this temperature
Under maintain the reflux for react 2h, obtain nonyl benzene methanol；
Step c, put into nonyl benzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；De-
Water is complete, after being passed through nitrogen displacement, presses the mol ratio 1/ (15～17) to nonyl benzene methanol/oxirane and is slowly introducing epoxy second
Alkane, control reaction temperature 120～140 DEG C, pressure is less than 0.2MPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 15, stop being passed through oxirane, react into
Enter termination phase, cool to 120 DEG C, add acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, bag filter
Dress, obtains nonyl benzene methanol polyoxyethylene ether-15.
Embodiment 4
A kind of nonyl benzene methanol polyoxyethylene ether-20 emulsifying agent without APEO, its preparation method is as follows:
Step a, in a kettle., adds nonyl benzene, paraformaldehyde, sodium bromide, anti-in 70 DEG C under acid catalyst effect
Answering 6～8h, be subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains nonyl
Bromobenzyl；
Step b, in a kettle., adds nonyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, in this temperature
Under maintain the reflux for react 2h, obtain nonyl benzene methanol；
Step c, put into nonyl benzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；De-
Water is complete, after being passed through nitrogen displacement, presses the mol ratio 1/ (20～22) to nonyl benzene methanol/oxirane and is slowly introducing epoxy second
Alkane, control temperature of reactor 120～140 DEG C, pressure is less than 0.2MPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 20, stop being passed through oxirane, react into
Enter termination phase, cool to 120 DEG C, add acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, bag filter
Dress, obtains nonyl benzene methanol polyoxyethylene ether-20.
Embodiment 5
A kind of nonyl benzene methanol polyoxyethylene ether-40 emulsifying agent without APEO, its preparation method is as follows:
Step a, in a kettle., adds nonyl benzene, paraformaldehyde, sodium bromide, anti-in 70 DEG C under acid catalyst effect
Answering 6～8h, be subsequently poured in frozen water, successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains nonyl
Bromobenzyl, stand-by；
Step b, in a kettle., adds nonyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, in this temperature
Under maintain the reflux for react 2h, obtain nonyl benzene methanol, stand-by；
Step c, put into nonyl benzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；De-
Water is complete, after being passed through nitrogen displacement, presses the mol ratio 1/ (40～43) to nonyl benzene methanol/oxirane and is slowly introducing epoxy second
Alkane, control temperature of reactor 120～140 DEG C, pressure is less than 0.2MPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 40, stop being passed through oxirane, react into
Enter termination phase, cool to 120 DEG C, add acetic acid and neutralize；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, bag filter
Dress, obtains nonyl benzene methanol polyoxyethylene ether-40.
According to relevant criterion, the performance of the nonyl benzene methanol polyoxyethylene ether emulsifying agent prepared in the embodiment of the present invention is entered
Row detection, test result is as shown in table 1.
Table 1: nonyl benzene methanol polyoxyethylene ether emulsifying agent technical specification
Wherein HLB is hydrophilic-hydrophobic balance value.
Above description is only the preferred embodiment of the application and the explanation to institute's application technology principle.People in the art
Member should be appreciated that invention scope involved in the application, however it is not limited to the technology of the particular combination of above-mentioned technical characteristic
Scheme, also should contain in the case of without departing from described inventive concept simultaneously, above-mentioned technical characteristic or its equivalent feature carry out
Combination in any and other technical scheme of being formed.Such as features described above has similar merit with (but not limited to) disclosed herein
The technical scheme that the technical characteristic of energy is replaced mutually and formed.
Claims (5)
1. an alkylbenzene methanol polyoxyethylene ether, it is characterised in that the molecular structure of described alkylbenzene methanol polyoxyethylene ether
Including hydrophobic group and hydrophilic group, molecular structural formula is as follows:
Wherein, the R in molecular formula is alkyl, n=3～50.
Alkylbenzene methanol polyoxyethylene ether the most according to claim 1, it is characterised in that described n=4～40.
Alkylbenzene methanol polyoxyethylene ether the most according to claim 1, it is characterised in that described hydrophobic group is molecular formula
In alkylbenzene methanol segment, described hydrophilic group is polyoxyethylene ether segment in molecular formula；Described hydrophobic group is with hydrophilic
The mol ratio of group is 1:(3～50).
Alkylbenzene methanol polyoxyethylene ether the most according to claim 3, it is characterised in that described hydrophobic group is with hydrophilic
The mol ratio of group is 1:(4～40).
5. a preparation method for the alkylbenzene methanol polyoxyethylene ether as described in claim 1-4 any one, its feature exists
In, comprise the following steps:
A, in a kettle., adds alkylbenzene, paraformaldehyde, sodium bromide, under acidic catalyst effect in 70 DEG C of reactions 6～
8h, is subsequently poured in frozen water, and successively with water, saturated sodium bicarbonate solution washing organic layer, decompression distillation obtains alkyl bromobenzyl；
B, in a kettle., adds alkyl bromobenzyl, methanol, potassium hydroxide, is warmed up to reflux state, keeps back at this temperature
Stream reaction 2h, obtains alkylbenzene methanol；
C, add alkylbenzene methanol, catalyst potassium hydroxide in a kettle., then heat up and vacuum dehydration；It is dehydrated complete,
After being passed through nitrogen displacement, mol ratio 1:(3～50 by alkylbenzene methanol/oxirane) it is slowly introducing oxirane, control
Reaction temperature 120～140 DEG C, pressure is less than 0.2mPa；
D, detection, when stopping being passed through oxirane after the degree of polymerization that reaction reaches required, are reacted into termination phase, cooling fall
Temperature, to 120 DEG C, adds acetic acid and neutralizes；It is subsequently adding hydrogen peroxide for decoloration；It is cooled to 80 DEG C, filters and packages, obtain alkylbenzene methanol
Polyoxyethylene ether.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109400449A (en) * | 2018-09-29 | 2019-03-01 | 中国日用化学研究院有限公司 | A method of preparing alkyl phenyl alcohol polyoxyethylene ether |
| 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 |
| CN111492046A (en) * | 2017-12-20 | 2020-08-04 | 亨斯迈石油化学有限责任公司 | Aromatic-based polyetheramine alkoxylates |
| CN111511800A (en) * | 2017-10-30 | 2020-08-07 | 百深有限责任公司 | Environmentally compatible detergents for inactivation of lipoenveloped viruses |
-
2016
- 2016-07-19 CN CN201610569768.XA patent/CN106187714A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111511800A (en) * | 2017-10-30 | 2020-08-07 | 百深有限责任公司 | Environmentally compatible detergents for inactivation of lipoenveloped viruses |
| CN111511800B (en) * | 2017-10-30 | 2023-11-28 | 武田药品工业株式会社 | Environment-compatible detergent for inactivating lipid-enveloped viruses |
| CN111492046A (en) * | 2017-12-20 | 2020-08-04 | 亨斯迈石油化学有限责任公司 | Aromatic-based polyetheramine alkoxylates |
| CN109400449A (en) * | 2018-09-29 | 2019-03-01 | 中国日用化学研究院有限公司 | A method of preparing alkyl phenyl alcohol polyoxyethylene ether |
| CN109400449B (en) * | 2018-09-29 | 2022-06-10 | 中国日用化学研究院有限公司 | Method for preparing alkyl phenyl alcohol polyoxyethylene ether |
| 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 |
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