CN109970963A - A kind of synthetic method of allyl alkylphenol ethoxylate - Google Patents
A kind of synthetic method of allyl alkylphenol ethoxylate Download PDFInfo
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- CN109970963A CN109970963A CN201910232709.7A CN201910232709A CN109970963A CN 109970963 A CN109970963 A CN 109970963A CN 201910232709 A CN201910232709 A CN 201910232709A CN 109970963 A CN109970963 A CN 109970963A
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- allyl
- alkylphenol ethoxylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
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Abstract
A kind of synthetic method of allyl alkylphenol ethoxylate is related to organic compound synthesis technical field.Under load-type solid acid catalyst catalysis and oxygen free condition, allyl glycidyl ether and alkylphenol are mixed and carry out ring-opening reaction, obtains allyl alkyl phenol；Then allyl alkyl phenol is mixed again with ethylene oxide, under conditions of base catalyst exists with anaerobic, carries out polymerization reaction；After polymerization reaction, through aging, obtain into allyl alkylphenol ethoxylate.The product of synthesis have the advantages that allyl be present in branch, ethylene oxide chain link are adjustable, allyl it is active it is good, allyl content is high, good with preferable heat-resistant salt-resistant performance and biodegradability.
Description
Technical field
The invention belongs to organic compound synthesis technical fields.
Background technique
Allyl alkylphenol ethoxylate is a kind of surfactant haveing excellent performance, due to branch and containing polymerization
Groups allyl is compared with straight chained alkyl phenol polyethenoxy ether, have excellent characteristic, such as good wetting, emulsification, decontamination,
The performances such as detergency, solubilising, blistering, antistatic, dispersion, antirust and lubrication, and be easy to use with other additive compatibilities, it is nontoxic
With the characteristics such as irritation is small, biological degradability, lower dynamic surface tension and heat-resistant salt-resistant.It can be applied to response type emulsification
All conglomeraties such as agent, daily use chemicals, washing, weaving, leather, plating, papermaking, chemical fibre and the oil field displacement of reservoir oil.
Xi'an stone is reported in " Speciality Petrochemicals " (preparation of different polymerization degree polyether sulfonate and interface performance research)
With fatty alcohol polyoxyethylene ether and chloropropene nucleophilic substitution, terminal hydroxyl occur under alkaline condition for the Li Yongtai of oily university
Allylation reaction occurs and generates allyl aliphatic alcohol polyether.
" polymer material science and engineering " (Salt treatment of the quadripolymer containing polymeric monomer viscosifies and association behavior) reports
The Zhong Chuanrong of road Chengdu University of Technology is reacted 56h and synthesizes alkene as under solvent and metallic sodium effect in THF using OP-20 with allyl chloride
Propyl alkyl phenol polyethers.
The peaceful of University of Science & Technology, Beijing is reported in " chemical industry " (research of alkene addition process synthetic fatty alcohol ether sulfonate)
Zhang Lei with fatty alcohol polyoxypropylene ether and chloropropene under sodium hydroxide and phase transfer catalyst effect, at 110-130 DEG C and
0.35MPa reacts 3~5h.Cooling plus water stratification wash organic phase with appropriate dilute hydrochloric acid and hot water, washing 2-3 times up to
Crude product is transferred in rotation swallow bottle by the pH of water phase for 7 or so, is purified allyl deriv through rotary evaporation, is used high-efficient liquid phase color
Spectrum measurement reaction conversion ratio is 88 9%.
The method that above method is all made of etherified sealed end prepares allyl alkyl alcohol (or phenol) polyoxyethylene ether, has reaction
Ending ratio is low, generates side product chlorinated sodium and the environmental issues such as excessive allyl chloride is difficult to recycle.
A kind of α-phenylalkyl alcohol polyoxyethylene ether hydroxypropyl ether is described in patent document CN105968338A and its is spread out
The preparation method of biology, is used excessive benzene to be reacted using alchlor as catalyst with alkyl acyl chloride, removed by hydrolyzing, neutralizing
The benzene of amount obtains α-phenyl alkyl ketone；α-phenyl alkyl ketone again palladium-carbon catalyst effect under 130~170 DEG C, pressure 2~
3MPa and hydrogen carry out hydrogenating reduction, obtain α-phenylalkyl alcohol；α-phenylalkyl alcohol synthesizes α-phenyl with reacting ethylene oxide
Alkyl alcohol ethoxylates；Last α-phenylalkyl alcohol polyoxyethylene ether under Louis acid catalysis with allyl glycidyl ether
In 110~120 DEG C of reaction 4h, α-phenylalkyl alcohol polyoxyethylene ether hydroxypropyl allyl ether is made.But this method is more numerous
It is trivial, and the shortcomings that need high temperature and reaction with pressure, it is often more important that lewis acid remains in final product, it is difficult to handle, make
The acid value of product is high, has the shortcomings that the shelf-life is short.
Summary of the invention
In view of the above-mentioned problems in the prior art, it is an object of the present invention to provide simple process, load-type solid acid catalysts to recycle
Using, allyl activity is good, allyl content is high, the allyl alkylphenol ethoxylate with preferable heat-resistant salt-resistant performance
Synthetic method.
The technical scheme is that: it is under load-type solid acid catalyst catalysis and oxygen free condition, allyl glycidyl is sweet
Oily ether and alkylphenol mixing carry out ring-opening reaction, obtain allyl alkyl phenol；Then again by allyl alkyl phenol and epoxy second
Alkane mixing carries out polymerization reaction under conditions of base catalyst exists with anaerobic；After polymerization reaction, through aging, obtain at
Allyl alkylphenol ethoxylate.
The reaction equation of the above ring-opening reaction is as follows:
The reaction equation of polymerization reaction is as follows:
The allyl alkylphenol ethoxylate of acquirement has a structure that
M=8 or 9 in the above various formula, n=4~40.
There is the product that the present invention synthesizes allyl to be present in, and branch, ethylene oxide chain link is adjustable, allyl is active
Well, allyl content is high, has the advantages that preferable heat-resistant salt-resistant performance and biodegradability are good；And due in the first step
Load-type solid acid catalyst is used in reaction, has that mild condition, narrowly distributing, reaction speed be fast, catalyst noresidue, not shadow
The advantages that reaction and load-type solid acid catalyst for ringing next step ethylene oxide can be recycled.
Further, alkylphenol of the present invention is nonyl phenol or octyl phenol.Alkylphenol class polyethers is in detergent, print
Dye, chemical industry have been widely used, and have good infiltration, emulsification, dispersion, antiacid, alkali resistant, hard water resistance, anti-reduction, anti-oxidant energy
Power.
The ring-opening reaction temperature is 35~60 DEG C, the reaction time is 0.5~1h, the low, reaction time with reaction temperature
The advantages that short, side reaction is lacked.
The mixing molar ratio of the allyl glycidyl ether and nonyl phenol or octyl phenol is 1: 1, can avoid other techniques
Middle allyl glycidyl ether needs the shortcomings that excessive ability fully reacting, and avoids excessive allyl glycidyl ether
Caused by recycling the problem of environmental pollution, production cost is reduced.
The load-type solid acid catalyst is using aluminium oxide or silica as carrier, and load phosphotungstic acid or phosphomolybdic acid are described
The load quality of phosphotungstic acid or phosphomolybdic acid accounts for the 20~40% of load-type solid acid catalyst.The supported solid acid catalyst has
The advantages that surface area is big, loading good, and selectivity is good, and preferable reaction rate, reaction speed is fast, easily separated.
The molar ratio of the allyl alkyl phenol and ethylene oxide is 1: 4~40.Different ethylene oxide polymerization numbers
Product have different purposes.Ethylene oxide polymerization number is more, and the oxygen in product on molecule hydrophilic group is more, can shape with water
It is water-soluble better at more hydrogen bonds, it is commonly used for detergent and grease emulsifier and emulsifier etc..Ethylene oxide polymerization number is got over
Few, the oxygen in product on molecule hydrophilic group is fewer, and product can be dissolved in oil and not soluble in water, often as preparing sulfuric acid ester anion
The raw material of surfactant.
The base catalyst is KOH, NaOH, CH3OK or CH3ONa.Use caustic alkali for the ring opening catalyst of ethylene oxide,
Have the advantages that the advantages of narrow molecular weight distribution and polymerizable molecular amount are big.
The polymeric reaction temperature is 110~140 DEG C.The ring-opening polymerization of ethylene oxide needs to undergo chain initiation, chain
The links such as growth, need induction slowly that could react, and at a suitable temperature, be conducive to the polymerization reaction with ethylene oxide
It carries out, shortens the induction period of reaction, shorten the time of reaction.
When the polymerization reaction, the base catalyst account for allyl alkyl pure and mild ethylene oxide mixing gross mass 1~
3‰.The catalyst amount can guarantee going on smoothly for epoxyethane ring-expansion polymerization；If amount is very little, ethylene oxide is not easy instead
Should completely, the yield decline of product；If amount is too many, the acid amount for needing to neutralize also increases, to neutralize the amount of the salt of generation
Also it will increase, the solid waste amount of generation increases, and easily deepens the color of product.
In short, beneficial effects of the present invention are as follows:
(1) ring-opening reaction of the present invention is using load-type solid acid as catalyst, and selectivity is high, and by-product is few, mild condition,
Its catalytic capability is gradually discharging during ring-opening reaction, can preferably make nonyl phenol, octyl phenol and allyl glycidyl sweet
Oily ether is reacted, and the generation of the multi-epoxy object of high polymerization degree is reduced, and not needing allyl glycidyl ether excessively can
Carry out reaction with same mole.
(2) load-type solid acid catalyst is filled on the fixation device of reaction kettle, has the big reaction speed of catalytic amount
Fastly, it in material the advantages of basic noresidue, and can be recycled, save the cost of production.
(3) using load-type solid acid as catalyst, allyl glycidyl ether ring-opening reaction temperature is low, and allyl is protected
Stay rate high, product color is shallow.
Specific embodiment
Embodiment 1
1, the synthesis of allyl alkyl phenol:
The support type phosphomolybdic acid catalyst for accounting for fixed 1/3 volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphotungstic acid account for loaded catalyst 40%), nonyl phenol and the 114kg allyl glycidyl for being pumped into 220kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 55~60 DEG C of reaction 0.5h；Then 30 DEG C are cooled to
Hereinafter, filtering and discharging, obtains 334kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
The 334kg allyl alkyl phenol of step (1) is squeezed into polymerization reaction kettle, 3.2kgCH is added3OK, nitrogen displace sky
After gas, vacuumize after 110 DEG C of dehydration 1h, be passed through 1760kg reacting ethylene oxide under oxygen free condition, keep reaction temperature 130~
135 DEG C, after quantitative ethylene oxide has led to, aging is cooled to 80 DEG C and obtains 2094 kg crude products after 1 hour.
Crude product is moved into refining kettle, after being added water stirring 30 minutes of 60kg, adds phosphoric acid to be neutralized to neutrality, adds
Adsorbent dehydration, using filter, obtains 2080 kg allyl alkylphenol ethoxylates.
Embodiment 2
1, the synthesis of allyl alkyl phenol:
The support type phosphomolybdic acid catalyst for accounting for fixed 60% volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphomolybdic acid account for loaded catalyst 20%), octyl phenol and the 114kg allyl glycidyl for being pumped into 206kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 50~55 DEG C of reaction 1h；Then be cooled to 30 DEG C with
Under, filtering and discharging obtains 320kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
320kg allyl alkyl phenol is squeezed into polymerization reaction kettle, 2.4kg or CH is added3ONa after nitrogen displaces air, takes out
Vacuum is passed through 880kg reacting ethylene oxide after 110 DEG C of dehydration 1h under oxygen free condition, kept for 115~120 DEG C of reaction temperature, determines
After the ethylene oxide of amount has led to, aging is cooled to 80 DEG C and obtains 1200kg crude product after 1 hour.
Crude product is moved into refining kettle, after being added water stirring 30 minutes of 40kg, adds phosphoric acid to be neutralized to neutrality, adds
Adsorbent dehydration, using filter, obtains 1187kg allyl alkylphenol ethoxylate.
Embodiment 3
1, the synthesis of allyl alkyl phenol:
The support type phosphomolybdic acid catalyst for accounting for fixed 2/3 volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphomolybdic acid account for loaded catalyst 30%), nonyl phenol and the 114kg allyl glycidyl for being pumped into 220kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 35~40 DEG C of reaction 0.5h；Then 30 DEG C are cooled to
Hereinafter, filtering and discharging, obtains 334kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
The 334kg allyl alkyl phenol of step (1) is squeezed into polymerization reaction kettle, 5.1kgKOH is added, nitrogen displaces air
Afterwards, it vacuumizes after 110 DEG C of dehydration 1h, 176kg reacting ethylene oxide is passed through under oxygen free condition, keep reaction temperature 110~115
DEG C, after quantitative ethylene oxide has led to, aging is cooled to 80 DEG C and obtains 510 kg crude products after 1 hour.
Crude product is moved into refining kettle, after being added water stirring 30 minutes of 15kg, adds phosphoric acid to be neutralized to neutrality, adds
Adsorbent dehydration, using filter, obtains 501 kg allyl alkylphenol ethoxylates.
Embodiment 4
1, the synthesis of allyl alkyl phenol:
The carried phospho-tungstic acid catalyst for accounting for fixed 2/3 volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphotungstic acid account for loaded catalyst 20%), octyl phenol and the 114kg allyl glycidyl for being pumped into 206kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 40~45 DEG C of reaction 1h；Then be cooled to 30 DEG C with
Under, filtering and discharging obtains 320kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
320kg allyl alkyl phenol is squeezed into polymerization reaction kettle, 2.9kg or NaOH is added, after nitrogen displaces air, is taken out true
Sky is passed through 660kg reacting ethylene oxide after 110 DEG C of dehydration 1h under oxygen free condition, kept for 120~125 DEG C of reaction temperature, quantitatively
Ethylene oxide led to after, aging is cooled to 80 DEG C and obtains 980kg crude product after 1 hour.
Crude product is moved into refining kettle, be added 40 kg water stir 30 minutes after, add phosphoric acid to be neutralized to neutrality, then plus
Enter adsorbent dehydration, using filter, obtains 958 kg allyl alkylphenol ethoxylates.
Embodiment 5
1, the synthesis of allyl alkyl phenol:
The carried phospho-tungstic acid catalyst for accounting for fixed 1/3 volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphotungstic acid account for loaded catalyst 35%), octyl phenol and the 114kg allyl glycidyl for being pumped into 206kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 45~50 DEG C of reaction 45min；Then 30 are cooled to
DEG C hereinafter, filtering and discharging, obtains 320kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
320kg allyl alkyl phenol is squeezed into polymerization reaction kettle, 1kg or NaOH is added, after nitrogen displaces air, vacuumizes
After 110 DEG C of dehydration 1h, 440kg reacting ethylene oxide is passed through under oxygen free condition, 135~140 DEG C of reaction temperature of holding is quantitative
After ethylene oxide has led to, aging is cooled to 80 DEG C and obtains 760 kg crude products after 1 hour.
Crude product is moved into refining kettle, after being added water stirring 30 minutes of 30kg, adds phosphoric acid to be neutralized to neutrality, adds
Adsorbent dehydration, using filter, obtains 751kg allyl alkylphenol ethoxylate.
Embodiment 6
1, the synthesis of allyl alkyl phenol:
The carried phospho-tungstic acid catalyst for accounting for fixed 1/2 volume of device is packed into the fixation device in external circulation stirring open loop kettle
After (load quality of phosphotungstic acid account for loaded catalyst 40%), nonyl phenol and the 114kg allyl glycidyl for being pumped into 220kg are sweet
Oily ether, N2After displacement, stirring and circulating pump, snare drum N are opened2Side heating, in 45~50 DEG C of reaction 1h；Then be cooled to 30 DEG C with
Under, filtering and discharging obtains 334kg allyl alkyl phenol.
2, the synthesis of allyl alkylphenol ethoxylate:
The 334kg allyl alkyl phenol of step (1) is squeezed into polymerization reaction kettle, 3kgKOH is added, after nitrogen displaces air,
It vacuumizes after 110 DEG C of dehydration 1h, 1100kg reacting ethylene oxide is passed through under oxygen free condition, keep reaction temperature 125~130
DEG C, after quantitative ethylene oxide has led to, aging is cooled to 80 DEG C and obtains 1434 kg crude products after 1 hour.
Crude product is moved into refining kettle, be added 50 kg water stir 30 minutes after, add phosphoric acid to be neutralized to neutrality, then plus
Enter adsorbent dehydration, using filter, obtains 1420 kg allyl alkylphenol ethoxylates.
Material explanation: in above each example carried phospho-tungstic acid catalyst or support type phosphomolybdic acid catalyst be with aluminium oxide or
Silica is carrier, load phosphotungstic acid or phosphomolybdic acid, and the load quality of phosphotungstic acid or phosphomolybdic acid accounts for load-type solid acid catalyst
20~40%.
Claims (9)
1. a kind of synthetic method of allyl alkylphenol ethoxylate, it is characterised in that: urged in load-type solid acid catalyst
Change under oxygen free condition, allyl glycidyl ether and alkylphenol are mixed and carry out ring-opening reaction, obtains allyl alkyl phenol；
Then allyl alkyl phenol is mixed again with ethylene oxide, under conditions of base catalyst exists with anaerobic, carries out polymerization reaction；
After polymerization reaction, through aging, obtain into allyl alkylphenol ethoxylate.
2. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the alkylbenzene
Phenol is nonyl phenol or octyl phenol.
3. the synthetic method of allyl alkylphenol ethoxylate according to claim 1 or claim 2, it is characterised in that the allyl
The mixing molar ratio of base glycidol ether and alkylphenol is 1: 1.
4. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the open loop is anti-
Answer that temperature is 35~60 DEG C, the reaction time is 0.5~1h.
5. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the support type
Solid acid catalyst is using aluminium oxide or silica as carrier, load phosphotungstic acid or phosphomolybdic acid, the phosphotungstic acid or phosphomolybdic acid it is negative
Mounted mass accounts for the 20~40% of load-type solid acid catalyst.
6. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the allyl
The molar ratio of alkyl phenol and ethylene oxide is 1: 4~40.
7. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the base catalysis
Agent is KOH, NaOH, CH3OK or CH3ONa。
8. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the polymerization is anti-
Answering temperature is 110~140 DEG C.
9. the synthetic method of allyl alkylphenol ethoxylate according to claim 1, it is characterised in that the polymerization is anti-
At once, the base catalyst accounts for 1~the 3 ‰ of the pure and mild ethylene oxide mixing gross mass of allyl alkyl.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62104802A (en) * | 1985-07-24 | 1987-05-15 | Asahi Denka Kogyo Kk | Emulsifier for emulsion polymerization |
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- 2019-03-26 CN CN201910232709.7A patent/CN109970963A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62104802A (en) * | 1985-07-24 | 1987-05-15 | Asahi Denka Kogyo Kk | Emulsifier for emulsion polymerization |
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Application publication date: 20190705 |