CN106220679A - α phenylalkyl polyoxyethylenated alcohol phosphate ester and preparation method - Google Patents
α phenylalkyl polyoxyethylenated alcohol phosphate ester and preparation method Download PDFInfo
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- CN106220679A CN106220679A CN201610571398.3A CN201610571398A CN106220679A CN 106220679 A CN106220679 A CN 106220679A CN 201610571398 A CN201610571398 A CN 201610571398A CN 106220679 A CN106220679 A CN 106220679A
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- polyoxyethylenated alcohol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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Abstract
This application discloses a kind of α phenylalkyl polyoxyethylenated alcohol phosphate ester and preparation method, for nonionic, its molecular structure includes hydrophobic group and hydrophilic group, wherein, hydrophobic group is α phenylalkyl segment, hydrophilic group is polyoxyethylene ether segment, and hydrophobic group is 1:3～50 with the mol ratio of hydrophilic group.The emulsifying agent α phenylalkyl polyoxyethylenated alcohol phosphate ester without APEO of the present invention, there is good moistening, infiltration, emulsifying, dispersion, solubilising and cleaning function, can be used as emulsifying agent, textile auxiliary, detergent, dispersant, softening agent, crude oil demulsifier etc., substitute alkylphenol polyoxyethylene emulsifying agent completely, be widely used in the industries such as detergent, personal care articles, weaving, papermaking, oil, pesticide, pharmacy, printing, synthetic rubber, water-based emulsion, coating, ink, glue, plastics.
Description
Technical field
The disclosure relates generally to pluronic polymer synthesis technical field, is specifically related to emulsifying agent, particularly relates to α-octadecyloxy phenyl
Base polyoxyethylenated alcohol phosphate ester and preparation method.
Background technology
Emulsifying agent containing APEO (alkylphenol polyoxyethylene compounds) structure has good moistening, infiltration, breast
Change, dispersion, solubilising and cleaning function, the emulsifying agent being mainly used as on pesticide, textile auxiliary, defoamer, detergent, dispersant,
Emulsifying agent, softening agent, dyeing assistant, fibre finishing, crude oil demulsifier etc., be widely used in detergent, personal nursing daily
The industries such as product, weaving, papermaking, oil, metallurgy, pesticide, pharmacy, printing, synthetic rubber, water-based emulsion, plastics.APEO class emulsifying
Agent is the abbreviation of alkylphenol polyoxyethylene compounds, APEO include NPE (NPEO) account for 80～
85%, OPEO (OPEO) accounts for more than 15%, and dodecyl phenol polyethenoxy ether (DPEO) and binonylphenol gather
Oxygen vinyl Ether (DNPEO) respectively accounts for 1%.Yield (calculating by the 100% effective content) anion 3,600,000 tons of whole world emulsifying agent, non-
3,650,000 tons of ion, both sexes 180,000 tons, cation 760,000 tons, wherein alkylphenol polyoxyethylene (APEO) yearly consumption is for reaching 1,000,000
More than Dun, wherein more than 80% is NPE (NPEO).
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 formulated before 1976 regulation limit produce and
Use APEO, as European Union 1998 just at the detergent, abluent of personal consumption in limit use APEO, 2005 at clothing
And textile limits use APEO.
Clear stipulaties in Chinese environmental protection standard HJ 2,537 2014 " environmental labelling product technology requires water paint ": no
Obtain the material requirement artificially added, 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 replacing
For product, these substitute products include AEO (fatty alcohol-polyoxyethylene ether), isomeric alcohol polyethenoxy ether, AES (fatty alcohol polyoxy
Vinyl Ether sodium sulfate), SAS (alkylsulfonate), AOS (α sodium olefin sulfonate), APG (alkyl polyglucoside), fatty alcohol-polyoxyethylene 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.
Develop a kind of alkyl phenol this band benzene ring structure that is similar to and the most not there is the emulsifying agent of alkyl phenol toxicity to substitute alkane
The emulsifying agent of base phenol structure is necessary.
Summary of the invention
In view of drawbacks described above of the prior art or deficiency, it is desirable to provide a kind of emulsifying agent without APEO, α-phenylalkyl
Polyoxyethylenated alcohol phosphate ester.
First aspect, it is provided that a kind of α-phenylalkyl polyoxyethylenated alcohol phosphate ester, described α-phenylalkyl alcohol polyoxy second
Alkene ether phosphate molecular structure includes hydrophobic group and hydrophilic group, and molecular structural formula is as follows:
Wherein, n=5～18, m=3～50.
Second aspect, it is provided that a kind of α-phenylalkyl polyoxyethylenated alcohol phosphate preparations, comprises the following steps:
A, in a kettle., with excessive benzene as solvent, adds aluminum trichloride catalyst, drips alkane at temperature 40～70 DEG C
Base acyl chlorides, hydrolyzes after reaction, neutralizes, decompression distillation removing benzene, obtains α-phenyl alkyl ketone, stand-by；
B, hydrogenation autoclave in, in palladium carbon catalyst, temperature 130～170 DEG C, the condition of pressure 2.0～3.0mPa
Under, α-phenyl alkyl ketone hydrogenating reduction, obtain α-phenylalkyl alcohol, stand-by；
C, putting into α-phenylalkyl alcohol, catalyst KOH in a kettle., then heat up vacuum dehydration；It is dehydrated complete, is passed through
After nitrogen displacement, by α-phenyl capryl alcohol/oxirane 1:(3～50) mol ratio be slowly introducing oxirane and react, control
Make described reaction temperature 120～140 DEG C, pressure is less than 0.2mPa；
D, detection stop being passed through oxirane after reaction reaches the corresponding degree of polymerization, 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, discharging, filter and package, obtain α-phenyl
Alkyl alcohol ethoxylates, stand-by；
E, in a kettle., adds phosphorus pentoxide and carries out esterification, be warming up to 60 DEG C, and then insulation reaction 3h adds
Enter water, after being warmed up to 70 DEG C of reaction 1h, cool to 40 DEG C and add moisture content dilution, filter and package, prepare α-phenylalkyl alcohol polyoxy second
Alkene ether phosphate.
α-phenylalkyl polyoxyethylenated alcohol phosphate ester that the embodiment of the present application provides has good moistening, infiltration, breast
Change, dispersion, solubilising and cleaning function, can be used as emulsifying agent, textile auxiliary, detergent, dispersant, softening agent, crude oil demulsifier
Deng, completely substitute alkylphenol polyoxyethylene emulsifying agent, be widely used in detergent, personal care articles, weaving, papermaking, oil,
The industries such as pesticide, 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 embodiment of the present invention provides a kind of α-phenylalkyl polyoxyethylenated alcohol phosphate ester, and its molecular structure includes hydrophobic group
Group and hydrophilic group, molecular structural formula is as follows:
Wherein, n=5～18, m=3～50, R is H or Na or K or NH4。
Further, n=7～12, m=4～40.
Further, hydrophobic group is the α in molecular formula-phenylalkyl segment, and hydrophilic group is polyoxy second in molecular formula
Alkene ether phosphate segment；Hydrophobic group is 1:(3～50 with the mol ratio of hydrophilic group).
Further, mol ratio is 1:(4～40).
Wherein, α-phenylalkyl polyoxyethylenated alcohol phosphate synthesis mechanism that the embodiment of the present invention provides, such as following formula
Shown in:
Wherein, the n=5 in reaction equation～18, preferably n=7～12；M=3～50, preferably m=4～40.
α-phenylalkyl polyoxyethylenated alcohol phosphate ester that the present invention provides 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.
Preparation to α-phenylalkyl polyoxyethylenated alcohol phosphate ester is described further with the following Examples, if α-benzene
Base capryl alcohol code name is BO-, and ethoxymer distribution is (EO) m, and product designation is BO-(EO) m, and phosphate ester code name is PH-, phosphoric acid
Ammonium code name is PNH4-, and potassium phosphate code name is PK-；α-phenylalkyl polyoxyethylenated alcohol phosphate ester code name be BO-EO (m) PH, α-
Phenylalkyl polyoxyethylenated alcohol ammonium phosphate code name is BO-EO (m) PNH4, α-phenylalkyl polyoxyethylenated alcohol potassium phosphate code name
For BO-EO (m) PK.
Embodiment one:
A kind of α without APEO-phenyl capryl alcohol polyoxyethylene ether (10) phosphate ester emulsifying agent, product designation is BO-EO (10)
PH, its preparation technology is as follows:
Step a, in a kettle., with excessive benzene as solvent, adds aluminum trichloride catalyst, drips at temperature 40～70 DEG C
Add caprylyl chloride, hydrolyze after reaction, neutralize, decompression distillation removing benzene, prepare intermediate α-phenyl octanone, stand-by；
Step b, hydrogenation autoclave in, at palladium carbon catalyst, temperature 130～170 DEG C, the bar of pressure 2.0～3.0mPa
Under part, α-phenyl octanone hydrogenating reduction, prepare α-phenyl capryl alcohol, stand-by；
Step c, putting into α-phenyl capryl alcohol, catalyst KOH in a kettle., then heat up vacuum dehydration；It is dehydrated complete, logical
After entering nitrogen displacement, by mol ratio 1:(10～12 of α-phenyl capryl alcohol/oxirane) it is slowly introducing oxirane, control reaction
Temperature 120～140 DEG C, pressure is less than 0.2mPa；
Step d, detection are when reaction reaches the required degree of polymerization (EO) ≈ 10, and stopping is 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, prepares α-phenyl capryl alcohol polyoxy
Vinyl Ether-10, stand-by；
Step e, in aforesaid reaction vessel, add phosphorus pentoxide carry out esterification, be warming up to 60 DEG C, insulation reaction
3h, is subsequently adding water, after being warmed up to 70 DEG C of reaction 1h, cools to 40 DEG C and adds moisture content dilution, filter and package, prepare α-phenyl capryl alcohol
Polyoxyethylene ether (10) phosphate ester.
Embodiment two:
A kind of α without APEO-phenyl octyl group polyoxyethylenated alcohol (5) ammonium phosphate emulsifying agent, product designation is BO-EO (5)
PNH4, its preparation technology is as follows:
Step a, in a kettle., with excessive benzene as solvent, adds aluminum trichloride catalyst, drips at temperature 40～70 DEG C
Add caprylyl chloride, hydrolyze after reaction, neutralize, decompression distillation removing benzene, prepare intermediate α-phenyl octanone, stand-by；
Step b, hydrogenation autoclave in, at palladium carbon catalyst, temperature 130～170 DEG C, the bar of pressure 2.0～3.0mPa
Under part, α-phenyl octanone hydrogenating reduction, prepare α-phenyl capryl alcohol, stand-by；
Step c, putting into α-phenyl capryl alcohol, catalyst KOH in a kettle., then heat up vacuum dehydration；It is dehydrated complete, logical
After entering nitrogen displacement, by mol ratio 1:(5～6 of α-phenyl capryl alcohol/oxirane) it is slowly introducing oxirane, control reaction temperature
Spend 120～140 DEG C, pressure is less than 0.2mPa；
Step d, detection, when reaction reaches the required degree of polymerization (EO) ≈ 5, stop being passed through oxirane, are reacted into
Termination phase, cools to 120 DEG C, adds acetic acid and neutralizes；It is subsequently adding hydrogen peroxide for decoloration, prepares α-phenyl capryl alcohol polyoxy second
Alkene ether-5, stand-by；
Step e, in aforesaid reaction vessel, add phosphorus pentoxide carry out esterification, be warming up to 60 DEG C, insulation reaction
3h, is subsequently adding water, after being warmed up to 70 DEG C of reaction 1h, cools to 40 DEG C and adds ammonia neutralization, dilute, filter and package, system
Obtain α-phenyl capryl alcohol polyoxyethylene ether (5) ammonium phosphate.
Embodiment three:, hydrolyze after reaction, neutralize, decompression distillation removing benzene, prepare intermediate α-phenyl different nonyl ketone, treat
With；
Step b, hydrogenation autoclave in, at palladium carbon catalyst, temperature 130～170 DEG C, the bar of pressure 2.0～3.0mPa
Under part, α-phenyl different nonyl ketone hydrogenating reduction, prepare α-phenyl different nonyl alcohol, stand-by；
Step c, putting into α-phenyl different nonanoyl alcohol, catalyst KOH in a kettle., then heat up vacuum dehydration；It has been dehydrated
Finish, after being passed through nitrogen displacement, by mol ratio 1:(4～5 of α-phenyl different nonyl alcohol/oxirane) it is slowly introducing oxirane,
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, are reacted into
Termination phase, cools to 120 DEG C, adds acetic acid and neutralizes；It is subsequently adding hydrogen peroxide for decoloration, prepares α-phenyl different nonyl alcohol and gather
Oxygen vinyl Ether-15, stand-by；
Step e, in aforesaid reaction vessel, add phosphorus pentoxide carry out esterification, be warming up to 60 DEG C, insulation reaction
3h, is subsequently adding water, after being warmed up to 70 DEG C of reaction 1h, cools to 40 DEG C and adds KOH neutralization, dilute, filter and package, prepare
α-phenyl different nonyl polyoxyethylenated alcohol (4) potassium phosphate.
According to relevant criterion, to the α-phenylalkyl polyoxyethylenated alcohol phosphate ester emulsifying agent prepared in the embodiment of the present invention
Performance detect, test result is as shown in table 1.
Table 1: α-phenylalkyl polyoxyethylenated alcohol phosphate ester emulsifying agent technical specification
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. α-phenylalkyl polyoxyethylenated alcohol phosphate ester, it is characterised in that described α-phenylalkyl polyoxyethylenated alcohol
Phosphate ester molecular structure includes hydrophobic group and hydrophilic group, and molecular structural formula is as follows:
Wherein, n=5～18, m=3～50, R is H or Na or K or NH4。
α the most according to claim 1-phenylalkyl polyoxyethylenated alcohol phosphate ester, it is characterised in that described n=7～
12, m=4～40.
α the most according to claim 1-phenylalkyl polyoxyethylenated alcohol phosphate ester, it is characterised in that described hydrophobic group
For the α in molecular formula-phenylalkyl segment, described hydrophilic group is polyoxyethylene ether phosphate segment in molecular formula；Described thin
Water base group is 1:(3～50 with the mol ratio of described hydrophilic group).
α the most according to claim 3-phenylalkyl polyoxyethylenated alcohol phosphate ester, it is characterised in that described mol ratio is
1:(4～40).
5. the α as described in claim 1-4 is arbitrary-phenylalkyl polyoxyethylenated alcohol phosphate preparations, its feature
It is, comprises the following steps:
A, in a kettle., with excessive benzene as solvent, adds aluminum trichloride catalyst, drips alkyl acyl at temperature 40～70 DEG C
Chlorine, hydrolyzes after reaction, neutralizes, decompression distillation removing benzene, obtains α-phenyl alkyl ketone, stand-by；
B, hydrogenation autoclave in, under conditions of palladium carbon catalyst, temperature 130～170 DEG C, pressure 2.0～3.0mPa, α-
Phenyl alkyl ketone hydrogenating reduction, obtains α-phenylalkyl alcohol, stand-by；
C, putting into α-phenylalkyl alcohol, catalyst KOH in a kettle., then heat up vacuum dehydration；It is dehydrated complete, is passed through nitrogen
After displacement, by α-phenyl capryl alcohol/oxirane 1:(3～50) mol ratio be slowly introducing oxirane and react, control institute
State reaction temperature 120～140 DEG C, pressure is less than 0.2mPa；
D, detection when reaction reaches the corresponding degree of polymerization after stopping be passed through oxirane, be reacted into 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, discharging, filter and package, obtain α-phenylalkyl
Polyoxyethylenated alcohol, stand-by；
E, in a kettle., adds phosphorus pentoxide and carries out esterification, be warming up to 60 DEG C, and insulation reaction 3h is subsequently adding water,
After being warmed up to 70 DEG C of reaction 1h, cool to 40 DEG C and add moisture content dilution, filter and package, prepare α-phenylalkyl polyoxyethylenated alcohol phosphorus
Acid esters.
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