CN1280994A - Process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde - Google Patents
Process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde Download PDFInfo
- Publication number
- CN1280994A CN1280994A CN00112451.XA CN00112451A CN1280994A CN 1280994 A CN1280994 A CN 1280994A CN 00112451 A CN00112451 A CN 00112451A CN 1280994 A CN1280994 A CN 1280994A
- Authority
- CN
- China
- Prior art keywords
- phenol
- vinylbenzene
- formaldehyde
- acid
- condenses
- 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.)
- Granted
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000007524 organic acids Chemical class 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 5
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 15
- 229920001568 phenolic resin Polymers 0.000 claims description 15
- DNIKXCUKOGVNIO-UHFFFAOYSA-N formaldehyde;phenol;styrene Chemical compound O=C.OC1=CC=CC=C1.C=CC1=CC=CC=C1 DNIKXCUKOGVNIO-UHFFFAOYSA-N 0.000 claims description 13
- 230000029936 alkylation Effects 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 10
- 238000006266 etherification reaction Methods 0.000 claims description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 238000007037 hydroformylation reaction Methods 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UZRCGISJYYLJMA-UHFFFAOYSA-N phenol;styrene Chemical compound OC1=CC=CC=C1.C=CC1=CC=CC=C1 UZRCGISJYYLJMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 claims 1
- -1 organic acid salt Chemical class 0.000 abstract description 17
- 239000003995 emulsifying agent Substances 0.000 abstract description 4
- 239000003945 anionic surfactant Substances 0.000 abstract description 2
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 238000010792 warming Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 208000005156 Dehydration Diseases 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 241000723353 Chrysanthemum Species 0.000 description 3
- 235000007516 Chrysanthemum Nutrition 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- PRPOTJIXCAUJHU-UHFFFAOYSA-N C1(=CC=CC=C1)O.C=C.C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)O.C=C.C1=CC=CC=C1 PRPOTJIXCAUJHU-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RYSNDQDGZQEOAL-UHFFFAOYSA-N calcium;phenol Chemical compound [Ca].OC1=CC=CC=C1 RYSNDQDGZQEOAL-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007785 strong electrolyte Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Abstract
A process for preparing polyoxyvinethene as the condensate of styrene, phenol and formaldehyde is disclosed. It features that the organic acid or its mixed acid is used as the catalyst for the alkylating reaction of styrene or phenol to produce by one-step the primary, secondary and tertiary alkylphenols; as the catlyst for the aldehydizing reaction of alkylated product directly with formaldehyde; and as the neutralizer for alkali contained in etherified product. The organic acid salt generated by neutralization is a anionic surfactant used for agricultural emulsifier.
Description
Alkylphenol is a class important chemical product, is widely used as the intermediate of resin; Oxidation inhibitor as plastics such as polypropylene, polyethylene, polyvinyl chloride and Mierocrystalline celluloses; As butylbenzene, along the thermal oxidation stabilizer of synthetic rubber such as fourth, neoprene and natural rubber; Also can be used for intermediate of dyestuff and tensio-active agent or the like.
The catalyzer that synthesizing alkyl phenol is used can be classified as two big classes at present basically, and a class is a mineral acid: sulfuric acid, hydrochloric acid, phosphoric acid etc. and Louis mud acid: boron trifluoride, aluminum chloride etc. is made catalyzer.The main drawback of this class catalyzer is that 1. corrodibility is strong; 2. catalyzer is difficult to remove in material, removes and then generates inorganic acid salt, makes troubles to subsequent production; 3. boron trifluoride, aluminum chloride etc. easily cause environmental pollution, and to the water content in the raw material strict (generally should be controlled at 100-200ppm).
Another kind ofly make catalyzer with solid acid, patents such as Japan, Britain and USSR (Union of Soviet Socialist Republics) report is used Zeo-karb, faujusite, β, γ zeolite or sealumination modified Y zeolite; Phenol aluminium, phenol calcium or poly phenol aluminium etc. are made catalyzer, produce mono-substituted alkylphenol.The patent that catalyzer synthesizes one, two, three substituted alkyl phenol of different ratios, suitability for industrialized production are done with heteropolyacid and salt thereof by Nanjing Normal University.Though this class catalyzer has overcome the various shortcoming of the first kind, it exists catalyzer price height, makes difficulty; A part of catalyzer easily is deposited in the bottom of reactor in the production, and catalytic efficiency is reduced, and stirs and easily causes catalyst breakage, forms mechanical impurity; It is few that catalyzer is reused number of times, and production cost is increased; Catalyzer uses the back to form deficiencies such as waste products.
The objective of the invention is to avoid above-mentioned the deficiencies in the prior art part and provide a kind of organic acid or its mixing acid both can make catalyzer in alkylation, the aldehyde reaction process, can behind etherification reaction, do the process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde of the neutralizing agent of alkali again.
Purpose of the present invention can reach by following measure:
Vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 new synthetic process is characterized in that:
A, carry out the catalyzer of alkylated reaction as vinylbenzene, phenol with organic acid or its mixing acid, vinylbenzene is that 2.0-3.0 is than 1 with the feed ratio of phenol, catalyst levels is the 3-20 ‰ of vinylbenzene phenol total amount, under the normal pressure, temperature of reaction 100-160 ℃, the time 3-5 of drip styrene hour, be incubated 1.0-1.5 hour;
Product after b, the alkylation and formaldehyde carry out aldehyde reaction, and the formaldehyde consumption is 6-12%, generate vinylbenzene phenol formaldehyde (PF) condenses;
The vinylbenzene phenol formaldehyde (PF) condenses of c, generation, neutralize with 0.3-1.2% alkali, transfer pH value to 8-12, temperature of reaction 140-170 ℃ with epoxy second in alkane (EO), propylene oxide (PO) carry out etherification reaction, EO (or PO) is 1.8～3.2 to 1 with the feed ratio of hydroformylation intermediate, the etherificate time is 4-8 hour, be incubated 0.5-1.0 hour, product after the etherificate carries out the alkali neutralization with organic acid or its mixing acid of a, transfer pH value 5-6 to be as the criterion, can produce nonionic surface active agent-vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7.
Purpose of the present invention can also reach by following measure:
Organic acid can adopt phenylformic acid
R
1: H or-COOH; Phenylsulfonic acid
R
2:-CH
3,-C
12H
25,-NH
2Naphthene sulfonic acid
Or its mixing acid;
Also can be used for C
3-C
16The alkylation of alkene and phenols.
The present invention has following advantage compared to existing technology:
The present invention is as catalyzer with organic acid or its mixing acid, its topmost characteristics are that organic acid or its mixing acid both can have been made the catalyzer in alkylation, the aldehyde reaction process, can behind etherification reaction, make the neutralizing agent of alkali again, the organic acid salt that forms is a kind of aniorfic surfactant, and is good with the intermiscibility of vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7; Because the synergy of nonionic and anion surfactant can make stability of emulsion increase, and the generation of old technology is inorganic salt, is a kind of strong electrolyte when forming water miscible liquid, bigger to the stability influence of emulsion.Organic acid salt becomes unfavorable factor and is favorable factor.
Secondly, organic acid or its mixing acid are made catalyzer, can dissolve each other with material, form homogeneous system and help reaction.What generate when alkylation, hydroformylation and etherificate post neutralization is organic acid salt, is aniorfic surfactant, therefore need not filter.Shortened the production cycle, can reduce investment, reduced production costs.
Organic acid acidity, oxidisability and volatility are all little than mineral acid, and be also less to the influence of the corrosion of equipment and environment.Become waste, shortcomings such as the three-waste pollution of formation after having avoided the generation of inorganic acid salt and solid acid catalyst to use.
Embodiment 1:
1, add phenol 100 grams in the four-necked bottle, catalyzer phenylformic acid 3.1 grams, oil bath is warming up to 100 ℃, under agitation drip styrene 210 restrains, rate of addition 2.5-3.0 Grams Per Minute, temperature maintenance be at 150 ℃-155 ℃, dropwised insulation 1.0 hours in 2.5 hours.
Use the gas chromatographic analysis product: benzoic acid transformation efficiency～100%
One substituted alkyl phenol: 23%, two substituted alkyl phenol, 51%, three substituted alkyl phenol 26%
2, above alkylation intermediate 310 grams change over to and are cooled to 60 ℃ in the autoclave, under agitation add 31 gram formaldehyde, are warming up to 95 ℃, and keep backflow to carry out aldehyde reaction in one hour.
The lining average molecular weight is: 483
3, the intermediate of hydroformylation is cooled to 70 ℃, adds 3.5 gram NaOH and neutralizes, and pH value is about 12, insulated and stirred 20 minutes, and oil bath is warming up to 140 ℃ of dehydrations one hour.
4,150-170 ℃, stir the 651 gram oxyethane (EO) of adding down and carry out etherification reaction, 4.5 hours etherificate time, be incubated 0.5 hour.The EO add-on is as the criterion with its cloud point, and the prediction cloud point is 70-75 ℃.Neutralize with 24 gram sulfonic acid, survey pH value, pH value is 6.0, reaches the requirement dehydration that can heat up, and dehydration is complete to be cooled to 80 ℃ of blowings.
Survey cloud point: 70 ℃
5, the horizontal sour calcium (500 of vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 and dodecylbenzene
#), organic solvent, solubility promoter carry out composite generation agricultural emulsifier 2201, are applicable to chrysanthemum ester class highly effective pesticide, its emulsifying property, dispersiveness still can, good stability.
Embodiment 2
1, add phenol 100 grams, vinylbenzene 220 grams in the four-necked bottle, catalyzer tosic acid 4.8 grams, other is with embodiment 1 gas chromatographic analysis result: phenol conversion～100%
One substituted alkyl phenol 16%; Two substituted alkyl phenol 58%; Three substituted alkyl phenol 26%
2, above alkylation intermediate 310 grams change in the autoclave, are cooled to 60 ℃ and under agitation add 35 gram formaldehyde, are warming up to 95 ℃, keep backflow to carry out aldehyde reaction in one hour.
Lining average molecular weight: 492
3, the intermediate of hydroformylation is cooled to 70 ℃, adds 3.5 gram NaOH and neutralizes, and pH value is about 12, insulated and stirred 20 minutes, and oil bath is warming up to 140 ℃, dewaters one hour.
4, under 155-170 ℃ of stirring, add 775 gram EO and carry out etherification reaction, 4 hours etherificate time, be incubated 1 hour, predict that cloud point is about 85 ℃.Neutralize with the horizontal acid of 24 grams, surveying pH value is 6.Heat up and dewater, be cooled to 70 ℃ of blowings.
Survey cloud point: 84 ℃
5, the horizontal sour calcium (500 of vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 and dodecylbenzene
#), organic solvent, solubility promoter carry out composite generation agricultural emulsifier 2201, are applicable to chrysanthemum ester class highly effective pesticide, and its emulsification, dispersion and stability are all good.
Embodiment 3
1, add phenol 100 grams in the four-necked bottle, mixing acid 5.4 grams of catalyzer tosic acid, Witco 1298 Soft Acid, oil bath is warming up to 120 ℃, drip styrene 260 grams, rate of addition 2.5-3.0 gram/mlh, holding temperature 150-160 ℃, 2.5 hour dropwise, be incubated 1.0 hours.
The above product of gas chromatographic analysis: phenol conversion～100%
One substituted phenylethylene phenol: 10%; Disubstituted benzenes phenol ethylene 45%; Trisubstituted benzene phenol ethylene 45%
2, above alkylation intermediate 310 grams change in the autoclave, are cooled to 60 ℃, under agitation add 30 gram formaldehyde, are warming up to 95 ℃, and keep backflow to carry out aldehyde reaction in one hour.Lining average molecular weight: 495
3, the intermediate of above hydroformylation is cooled to 70 ℃ and adds 3.5 gram KOH and neutralize, and pH value is 12, is incubated and stirs 15 minutes.Oil bath heats up and dewaters, and keeps dehydration in a hour during to 140 ℃.
4, under 150-170 ℃, adding 866 gram EO carry out etherification reaction, and the etherificate time is 5.0 hours, and EO finishes continuation and stirred 0.5 hour, carries out neutralization reaction with 24 gram sulfonic acid, and survey pH value 5.5 heats up and dewaters.Dehydration finishes and is cooled to 70 ℃ of blowings.
The survey cloud point is: 92 ℃
5, the horizontal sour calcium (500 of vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 and dodecylbenzene
#), organic solvent, solubility promoter carry out composite generation agricultural emulsifier 2201, are applicable to chrysanthemum ester class highly effective pesticide, its dispersiveness still can, emulsifying property and stability are all good.
Claims (3)
1, vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 new synthetic process is characterized in that:
A, carry out the catalyzer of alkylated reaction as vinylbenzene, phenol with organic acid or its mixing acid, vinylbenzene is that 2.0-3.0 is than 1 with the feed ratio of phenol, catalyst levels is the 3-20 ‰ of vinylbenzene phenol total amount, under the normal pressure, temperature of reaction 100-160 ℃, the time 3-5 of drip styrene hour, be incubated 1.0-1.5 hour;
Product after b, the alkylation and formaldehyde carry out aldehyde reaction, and the formaldehyde consumption is 6-12%, generate vinylbenzene phenol formaldehyde (PF) condenses;
The vinylbenzene phenol formaldehyde (PF) condenses of c, generation, neutralize with 0.3-1.2% alkali, transfer pH value to 8-12, temperature of reaction 140-170 ℃ with epoxy second in alkane (EO), propylene oxide (PO) carry out etherification reaction, EO (or PO) is 1.8～3.2 to 1 with the feed ratio of hydroformylation intermediate, the etherificate time is 4-8 hour, be incubated 0.5-1.0 hour, product after the etherificate carries out the alkali neutralization with organic acid or its mixing acid of a, transfer pH value to be as the criterion to 5-6, can produce nonionic surface active agent one vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7.
2, vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 new synthetic process according to claim 1 is characterized in that organic acid can adopt phenylformic acid
H or-COOH; Benzene sulphur
R
2:-CH
3,-C
12H
25,-NH
2Naphthene sulfonic acid
Or its mixing acid.
3, vinylbenzene phenol formaldehyde (PF) condenses Soxylat A 25-7 new synthetic process according to claim 1 is characterized in that also can be used for C
3-C
16The alkylation of alkene and phenols.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB00112451XA CN1152075C (en) | 2000-08-09 | 2000-08-09 | Process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB00112451XA CN1152075C (en) | 2000-08-09 | 2000-08-09 | Process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1280994A true CN1280994A (en) | 2001-01-24 |
| CN1152075C CN1152075C (en) | 2004-06-02 |
Family
ID=4582311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB00112451XA Expired - Fee Related CN1152075C (en) | 2000-08-09 | 2000-08-09 | Process for preparing polyoxyvinethene as condensate of styrene, phenol and formaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1152075C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101953820A (en) * | 2010-07-16 | 2011-01-26 | 暨南大学 | Application of styrene phenol compounds to preparing insulin sensitizer |
| CN104109555A (en) * | 2013-04-16 | 2014-10-22 | 中国石油化工股份有限公司 | Alkylation product treatment method |
| CN109627146A (en) * | 2018-12-07 | 2019-04-16 | 浙江皇马科技股份有限公司 | A kind of preparation method of styrylphenol |
-
2000
- 2000-08-09 CN CNB00112451XA patent/CN1152075C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101953820A (en) * | 2010-07-16 | 2011-01-26 | 暨南大学 | Application of styrene phenol compounds to preparing insulin sensitizer |
| CN101953820B (en) * | 2010-07-16 | 2012-05-30 | 暨南大学 | Application of styrene phenol compounds to preparing insulin sensitizer |
| CN104109555A (en) * | 2013-04-16 | 2014-10-22 | 中国石油化工股份有限公司 | Alkylation product treatment method |
| CN109627146A (en) * | 2018-12-07 | 2019-04-16 | 浙江皇马科技股份有限公司 | A kind of preparation method of styrylphenol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1152075C (en) | 2004-06-02 |
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