CN100447121C - Production process of antioxidant 2,6-di-tert-butyl-4-methy phenol - Google Patents
Production process of antioxidant 2,6-di-tert-butyl-4-methy phenol Download PDFInfo
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- CN100447121C CN100447121C CNB2006100472188A CN200610047218A CN100447121C CN 100447121 C CN100447121 C CN 100447121C CN B2006100472188 A CNB2006100472188 A CN B2006100472188A CN 200610047218 A CN200610047218 A CN 200610047218A CN 100447121 C CN100447121 C CN 100447121C
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Abstract
The production process of 2, 6-di-tert-butyl -4-methyl phenol includes the following steps: the first alkylation reaction of paracresol, isobutene and solid catalyst; leading the reaction product to the crystallizing kettle while leaving the catalyst for further use and lowering temperature slowly to separate out crystal; repeating the foregoing steps; washing the initial crystal with water solution of sodium hydroxide and separating oily matter from the washed alkali solution for reuse; recovering ethanol from the mother liquid in a rectifying tower for reuse and separating out inferior 2, 6-di-tert-butyl -4-methyl phenol product from the residue; drying the re-crystallized product and packing. The present invention has the advantages of no drained waste water, no environmental pollution, high product quality, etc.
Description
Technical field
The present invention relates to a kind of oxidation inhibitor 2,6 di tert butyl 4 methyl phenol production technique.
Background technology
2,6-di-tert-butyl-4-methy phenol (being called for short T501) is a kind of good oxidation inhibitor, be widely used, and be non-polluting oxidation inhibitor, can be used as the oxidation inhibitor of rubber such as polyvinyl chloride, polyethylene, polypropylene, polyester, polystyrene, ABS resin, isoprene-isobutylene rubber and latex, can suppress atmospheric oxidation, thermal destruction and copper evil etc. effectively, have do not pollute, not painted, fusing point is low, easily mixing, no blooming, do not influence the vulcanization of rubber, be applicable to white, light goods, foam article.Its production method is for p-cresol and iso-butylene being the raw material mixing, add sulfuric acid and carry out chemical reaction, generate 2,6 di tert butyl 4 methyl phenol, add soda ash and sulfuric acid again and carry out neutralization reaction, generate sodium sulfate, carbonic acid gas and water, through secondary water washing Ex-all sodium sulfate, produce 2-3 ton waste water, adopt aqueous ethanolic solution behind primary crystal and recrystallization, isolate the crystalline 2,6 di tert butyl 4 methyl phenol and enter next procedure.Mother liquor reclaims ethanol for production usefulness through rectifying tower, and remainder is told curved thing and substandard products T501 as production marketing, contains pure raffinate on a small quantity and delivers coal to mix with coal and burn, and after two subcrystalline product dryings are qualified, after analytical test is qualified, packs.The problem that above-mentioned technology exists is: add sulfuric acid when 1, feeding intake as catalyzer, must neutralize with alkali, in order to prevent line clogging, must be warmed up to 70-80 ℃ (one ton of water) to buck; But also to wash (each two tons of water) twice, qualified to guarantee ash.Therefore, both consumed heat energy, and must discharge 3 tons of left and right sides sulfur-containing waste waters again, polluted the environment after the discharging.2, adopt aqueous ethanolic solution to make the product secondary crystal, waste ethanol, the product that dissolves simultaneously in the ethanol can't be regained, and causes product yield to reduce.3, must be subjected to atmospheric oxidation through three pyritous products and pollute, the quality guaranteed period of product must be affected like this, and validity period can shorten.
Summary of the invention
The objective of the invention is to solve the problems referred to above that prior art exists, a kind of release discharge of wastewater is provided, free from environmental pollution, conservation reduces ethanol consumption and wastewater discharge, can improve the quality of products, the 2,6 di tert butyl 4 methyl phenol production technique that extends the shelf life.
The present invention is achieved in that
1, at first carries out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst are according to weight ratio 0.6～1: 1: 1.030～1.045: 0.016～0.075 gets material, described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.01～0.03, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down, reaction formula is:
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates;
3, carry out oil removing, according to washing the primary crystal thing down with 0.3: 1～0.5: 1 usefulness aqueous sodium hydroxide solution of crystallisate weight ratio normal temperature, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by;
4, according to weight ratio 0.8: 1～1: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Above-mentioned oxidation inhibitor 2, the production technique of 6-di-tert-butyl-4-methy phenol, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2,6 di t butyl phenol.
The invention has the beneficial effects as follows:
1, adopting can be with 2, solvent that the 6-di-tert-butyl-4-methy phenol mixes and the curing catalysts of forming by the mixture of the silico-aluminate and the vitriol oil, catalyzer and solvent can be recycled, saved the catalyzer usage quantity, remove neutralization and secondary high temperature water washing process from, solved 5～10 tons the problem that effluxes sour water environmental pollution every day.
2, because the change of reaction conditions makes reaction more complete, can save the usage quantity of iso-butylene, every still can be saved about 120kg, has avoided the Diisobutylene generation, the raw material and finished product dissolved of avoiding waste;
3, cut down the consumption of energy, improve the quality of products, need not three times and heat, save 160,000 kilocalorie heats, prolong the quality guaranteed period of product, make product reach the SH0015-90 standard fully.
Embodiment
Embodiment 1:
1, at first carries out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst are according to weight ratio 0.6～1: 1: 1.030～1.045: 0.016～0.075 gets material, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2,6 di t butyl phenol.Described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.01～1: 0.03, and solid catalyst is added in the alkylation still, adds p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down, reaction formula is:
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates;
3, carry out oil removing, according to washing the primary crystal thing down with 0.3: 1～0.5: 1 usefulness 0.5～5% aqueous sodium hydroxide solution normal temperature of crystallisate weight ratio, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by;
4, according to weight ratio 0.8: 1～1: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after the oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Embodiment 2:
1, at first carry out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst were according to weight ratio 0.6: 1: 1.03: 0.016 gets material, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene, solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.01, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down.
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates.
3, carry out oil removing, according to washing the primary crystal thing down with 0.3: 1 usefulness 0.5～5% aqueous sodium hydroxide solution normal temperature of crystallisate weight ratio, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by.
4, recrystallization, according to weight ratio 1: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after the oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Embodiment 3:
1, at first carry out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst were according to weight ratio 1: 1: 1.045: 0.075 gets material, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2, the 6-DI-tert-butylphenol compounds, described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.03, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down.
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates.
3, carry out oil removing, according to washing the primary crystal thing down with 0.5: 1 usefulness 0.5-5% of crystallisate weight ratio aqueous sodium hydroxide solution normal temperature, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by.
4, recrystallization, according to weight ratio 0.8: 1 with 60～65%% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after the oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Embodiment 4
1, at first carry out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst were according to weight ratio 0.8: 1: 1.038: 0.073 or get material at 1: 1.043: 0.017, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2, the 6-DI-tert-butylphenol compounds, described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.01 or 1: 0.02 or 1: 0.03, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down.
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates;
3, carry out oil removing, according to washing the primary crystal thing under the usefulness 0.5-5% aqueous sodium hydroxide solution normal temperature in 0.3: 1 or 0.4: 1 or 0.5: 1 with the crystallisate weight ratio, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by;
4, recrystallization, according to weight ratio 1: 1 or 0.8: 1 or 0.9: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after the oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Embodiment 5:
1, at first carry out alkylated reaction, can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst were according to weight ratio 0.8: 1: 1.039: 0.046 gets material, described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2, the 6-DI-tert-butylphenol compounds, described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.02, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down.
2, primary crystal reacts completely the back guide in crystallization kettle, and solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates;
3, carry out oil removing, according to washing the primary crystal thing down with 0.4: 1 usefulness 0.5-5% of crystallisate weight ratio aqueous sodium hydroxide solution normal temperature, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by;
4, recrystallization, according to weight ratio 0.9: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after the oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
Claims (2)
1, a kind of oxidation inhibitor 2,6 di tert butyl 4 methyl phenol production technique is characterized in that:
1.1. at first carry out alkylated reaction, according to weight ratio 0.6～1: 1: 1.030～1.045: 0.016～0.075 get can be with 2, the solvent that the 6-di-tert-butyl-4-methy phenol mixes, p-cresol, iso-butylene and solid catalyst, described solid catalyst is the mixture of the silico-aluminate and the vitriol oil, wherein the weight ratio of the silico-aluminate and the vitriol oil is 1: 0.01～1: 0.03, solid catalyst is added in the alkylation still, add p-cresol and iso-butylene again, in 65 ℃～71 ℃ reactions down, reaction formula is:
1.2. primary crystal reacts completely the back guide in crystallization kettle, solid catalyst is stayed in the alkylation still for using next time, slowly cool to 25 ℃ then, crystallization is separated out fully, isolate crystallisate with whizzer, solvent returns the alkylation still, and above process constantly circulates;
1.3. carry out oil removing, according to washing the primary crystal thing down with 0.3: 1～0.5: 1 usefulness aqueous sodium hydroxide solution of crystallisate weight ratio normal temperature, crystallisate surface is cleaned, and the buck of telling is removed alkali lye behind the oily matter of suspension for recycling, and the oily matter of being removed is stand-by;
1.4 according to weight ratio 0.8: 1～1: 1 with 60～65% aqueous ethanolic solutions with after the primary crystal thing mixes, through recrystallization, isolated product enters next procedure, mother liquor reclaims ethanol through rectifying tower and uses for producing, remainder is told oily matter and substandard products 2, the 6-di-tert-butyl-4-methy phenol, the oily matter of telling after oily matter that mother liquor is told after rectifying tower reclaims ethanol and the oil removing mixes and substandard products 2, the 6-di-tert-butyl-4-methy phenol, go out as the product pin respectively, contain pure raffinate on a small quantity and deliver coal to mix with coal and burn; Product behind recrystallization enters the drying machine drying, the qualified back of analytical test packing.
2, oxidation inhibitor 2 according to claim 1, the production technique of 6-di-tert-butyl-4-methy phenol, it is characterized in that: described solvent is edible soybean oil or lubricant base or sesame oil or whiteruss or single tert-butyl phenol or iso-butylene dimer or low molecular polyisobutylene or single tertiary butyl tetramethyl phenol or 2,6 di t butyl phenol.
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102311318A (en) * | 2010-06-29 | 2012-01-11 | 如皋市金陵化工有限公司 | Processing technique of 2,6-ditbutyl-4-methylphenol |
| CN103990475B (en) * | 2014-05-30 | 2016-04-13 | 湖南利洁科技有限公司 | A kind of composite solid-acid catalyst and its preparation method and application |
| CN110256207B (en) * | 2019-06-26 | 2020-07-10 | 太原理工大学 | Method for extracting cresol and tert-butylated product thereof from coal-based liquid derivative |
| CN110759815A (en) * | 2019-10-31 | 2020-02-07 | 安徽海华科技有限公司 | Processing method of BHT (butylated hydroxytoluene) competitive product |
| CN111233634B (en) * | 2020-02-29 | 2022-10-18 | 陕西宝塔山新材料有限公司 | Method for controlling antioxidant BHT crystallization by program forced cooling |
| CN112225644A (en) * | 2020-10-15 | 2021-01-15 | 南京晶典抗氧化技术研究院有限公司 | Production method of alkylphenol liquid antioxidant |
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| US4418223A (en) * | 1982-03-29 | 1983-11-29 | Uop Inc. | Preparation of 2,4,6-trialkylphenols |
| CN1215042A (en) * | 1998-08-25 | 1999-04-28 | 义县精细化工总厂 | Process for pressing preparation of 2,6-di-tert-butyl-p-cresol |
| CN1313270A (en) * | 2000-03-13 | 2001-09-19 | 锦州石化天元集团公司 | Process for preparing 2,6-di-tear-butyl p-cresol |
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- 2006-07-15 CN CNB2006100472188A patent/CN100447121C/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2684359A (en) * | 1952-01-08 | 1954-07-20 | Allied Chem & Dye Corp | Reduction of aromatic nitrolgen compounds |
| US3933928A (en) * | 1973-08-27 | 1976-01-20 | Mitsui Toatsu Chemicals, Incorporated | Method for producing 2,6-di-tert.-butyl-4-cumyl phenol |
| US4380667A (en) * | 1978-09-25 | 1983-04-19 | Pierre Fabre S.A. | 2'-(Orthochlorobenzoyl)-4'-chloroglycylanilides, compositions thereof, and use as medicaments |
| US4418223A (en) * | 1982-03-29 | 1983-11-29 | Uop Inc. | Preparation of 2,4,6-trialkylphenols |
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