CN1504445A - Novel process for preparing alkyl phenol - Google Patents
Novel process for preparing alkyl phenol Download PDFInfo
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- CN1504445A CN1504445A CNA021533407A CN02153340A CN1504445A CN 1504445 A CN1504445 A CN 1504445A CN A021533407 A CNA021533407 A CN A021533407A CN 02153340 A CN02153340 A CN 02153340A CN 1504445 A CN1504445 A CN 1504445A
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Abstract
The invention provides a novel process for preparing alkyl phenol, wherein acidic carclazyte is used as catalyst to be added by super strong acid for preparatory treatment for 10-120 minutes, and oxybenzene and olefin are added for reaction. After the hydrocarbon reaction ends, 0.1-15% (wt%) alkaline earth oxide or hydroxide and / or 0-5% (wt%) activated charcoal are added for continuance reaction for 10-120 minutes. Finally deslagging and decompression separation are proceeded to obtain alkyl phenol. The alkyl phenol making process according to the invention realizes high degree of purity and yield of reaction, shadow product color, and fine storage stability.
Description
Relate to the field
The present invention relates to a kind of novel method of alkylphenol preparation, specifically is a kind of acidifying carclazyte catalytic preparation alkylphenol novel method, belongs to field of fine chemical.
Background technology
Alkylphenol is mainly used in fields such as nonionogenic tenside, sanitas, resin improved agent, textile auxiliary agent and clean disperser for lubricating oil as a class important fine chemical material and intermediate.Alkylphenol normally carries out alkylated reaction by phenol and alkene and makes, but the method difference because of preparing, prepared alkylphenol product quality variance is bigger.Mass defects such as at present, mainly exist alkylphenol purity lower, yield is on the low side, and colorimetric is bigger, and the storage anti-oxidative stability is relatively poor, these problems especially show comparatively outstandingly in the preparation of high carbon number alkylphenol product.
Because of alkylphenol as a class important fine chemical material and intermediate, its quality product quality directly has influence on the quality height of the finished product of its application, so the purpose of this invention is to provide a kind of novel method for preparing the high-quality alkylphenol.The employing alkylphenol that the inventive method obtained is product purity height, reaction yield height not only, and product colour is light, stability in storage is also better.
Technology contents
The novel method of a kind of high-quality alkylphenol preparation of the present invention is as follows: install the there-necked flask that has electronic stirring, condensation water trap, solvent that input measures and acidic white earth catalyzer, stirring is warming up to 30～140 ℃, add super acids and carried out pre-treatment 10～120 minutes, add the phenol and the C of reacting weight then
6～C
40Alkene react.After treating that alkylation reaction finishes, add the oxide compound of alkaline-earth metal of its weight 0.1～15% or the gac of oxyhydroxide and/or 0～5%, continue reaction 10～120 minutes.Slagging-off, the unreacted phenol of decompression separation and alkene after filtration obtain the alkylphenol product at last.
Acidic white earth of the present invention is not less than 200 0.1NNaOHmL/100g for its activity degree, and moisture is not more than 8%.
Super acids of the present invention is the vitriol oil, hydrochloric acid, phosphoric acid etc.
Alkene of the present invention is C
6～C
40Alkene, especially be C
6～C
40Alpha-olefin and oligomerization of propene laurylene hydrocarbon.
The oxide compound of alkaline-earth metal of the present invention or oxyhydroxide are that purity is not less than 90% magnesium oxide, calcium oxide or magnesium hydroxide, calcium hydroxide.
Gac of the present invention is not less than 100% the special-purpose charcoal of grease for the caramel decolorizing ability.
Carclazyte acidification reaction temperature of the present invention is 30～140 ℃, is preferably 50～140 ℃.
The carclazyte acidification reaction time of the present invention is 10～120 minutes, is preferably 20～90 minutes.
The oxide compound of alkaline-earth metal of the present invention or the add-on of oxyhydroxide are 0.1～15% of reactant gross weight.
The add-on of gac of the present invention is 0～5%.
The temperature of reaction of the oxide compound of alkaline-earth metal of the present invention or oxyhydroxide and/or gac is 30～140 ℃.
The reaction times of the oxide compound of alkaline-earth metal of the present invention or oxyhydroxide and/or gac is 10～120 minutes.
The present invention is by introducing the pre-treatment of acidifying carclazyte, and having strengthened it provides the catalysis efficiency of proton hydrogen; The oxide compound or the oxyhydroxide of the alkaline-earth metal by adding doses utilize its physics chemical action, the acidic substance in the product are neutralized, and get rid of the superoxide and the gum asphalt of a part; By adding the gac of doses, removing remaining superoxide and gum asphalt, thereby improved the color of product, strengthened its antioxidative stabilizer.
Specific embodiment
Embodiment 1: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add super acids and carry out pre-treatment after 20 minutes, add 256 gram phenol and 360 gram C
6～C
30Alpha-olefin, 130 ℃ the reaction 4 hours.Then, add the calcium oxide of its weight 5% and 1% gac, continue reaction 40 minutes.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 495 grams after filtration, hydroxyl valency 5.0%, and GB/T 6540 surveys colorimetric less than 1.0.Product is placed after 1 month and is measured, and its colorimetric is 1.0.
Embodiment 2: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add super acids and carry out pre-treatment after 20 minutes, add 252 gram phenol and 360 gram C
14～C
18Alpha-olefin, 130 ℃ the reaction 4 hours.Then, add the magnesium oxide of its weight 9% and 0.6% gac, continue reaction 40 minutes.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 544.1 grams after filtration, hydroxyl valency 5.3%, and GB/T 6540 surveys colorimetric less than 1.0.Product is placed after 1 month and is measured, and its colorimetric is 1.0.
Embodiment 3: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add super acids and carry out pre-treatment after 20 minutes, add 252 gram phenol and 360 gram C
10～C
12Alpha-olefin, 140 ℃ the reaction 4 hours.Then, add the calcium hydroxide of its weight 3% and 3% gac, continue reaction 40 minutes.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 504 grams after filtration, hydroxyl valency 5.57%, and GB/T 6540 surveys colorimetric less than 1.0.Product is placed after 1 month and is measured, and its colorimetric is 1.0.
Comparative Examples 1: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add super acids and carry out pre-treatment after 20 minutes, add 256 gram phenol and 360 gram C
6～C
30Alpha-olefin, 140 ℃ the reaction 4 hours.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 477.5 grams after filtration, hydroxyl valency 5.3%, and GB/T 6540 surveys colorimetric 3.0.Product is placed after 1 month and is measured, and its colorimetric is greater than 3.5.
Comparative Examples 2: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add 252 gram phenol and 360 gram C
14～C
18Alpha-olefin, 140 ℃ the reaction 4 hours.Then, add the calcium hydroxide of its weight 0.8% and 3% gac, continue reaction 40 minutes.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 100.6 grams after filtration, hydroxyl valency 3.0%, and GB/T 6540 surveys colorimetric less than 2.0.Product is placed after 1 month and is measured, and its colorimetric is greater than 2.0.
Comparative Examples 3: in having 2000 milliliters of there-necked flasks of electronic stirring, condensation water trap, drop into 360 gram industrial napthas and 36 gram acidic white earths, stir and be warming up to 40 ℃, add 256 gram phenol and 360 gram C
10～C
12Alpha-olefin, 140 ℃ the reaction 4 hours.At last, slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol product 106.8 grams after filtration, hydroxyl valency 3.2%, and GB/T 6540 surveys colorimetric less than 2.0.Product is placed after 1 month and is measured, and its colorimetric is greater than 3.0.
Claims (12)
1. the novel method of an alkylphenol preparation is characterized in that: make catalyzer with acidic white earth, add super acids and after 10～120 minutes, add phenol and C 30～140 ℃ of pre-treatment again
6～C
40Alkene react, after treating that alkylation reaction finishes, add the oxide compound of alkaline-earth metal of its weight 0.1～15% or the gac of oxyhydroxide and/or 0～5%, continue reaction 10～120 minutes, after slagging-off, the unreacted phenol of decompression separation and alkene obtain alkylphenol.
2. in accordance with the method for claim 1, it is characterized in that: described acidic white earth is higher than 200 0.1NNaOHmL/100g for its activity degree, and moisture is less than 8%.
3. it is characterized in that in accordance with the method for claim 1: described super acids is the vitriol oil, hydrochloric acid, phosphoric acid etc.
4. it is characterized in that in accordance with the method for claim 1: described alkene is C
6～C
40Alkene, can be C
6～C
40Alpha-olefin and oligomerization of propene laurylene hydrocarbon.
5. it is characterized in that in accordance with the method for claim 1: the oxide compound of described alkaline-earth metal or oxyhydroxide are purity greater than 90% magnesium oxide, calcium oxide or magnesium hydroxide, calcium hydroxide.
6. it is characterized in that in accordance with the method for claim 1: described gac is higher than 100% the special-purpose charcoal of grease for the caramel decolorizing ability.
7. it is characterized in that in accordance with the method for claim 1: described carclazyte acidification reaction temperature is 30～140 ℃.
8. it is characterized in that in accordance with the method for claim 1: the described carclazyte acidification reaction time is 10～120 minutes.
9. it is characterized in that in accordance with the method for claim 1: the oxide compound of described alkaline-earth metal or the add-on of oxyhydroxide are 0.1～15% of reactant gross weight.
10. it is characterized in that in accordance with the method for claim 1: the add-on of described gac is 0～5%.
11. it is characterized in that in accordance with the method for claim 1: the temperature of reaction of the oxide compound of described alkaline-earth metal or oxyhydroxide and/or gac is 30～140 ℃.
12. it is characterized in that in accordance with the method for claim 1: the reaction times of the oxide compound of described alkaline-earth metal or oxyhydroxide and/or gac is 10～120 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021533407A CN1504445A (en) | 2002-11-29 | 2002-11-29 | Novel process for preparing alkyl phenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021533407A CN1504445A (en) | 2002-11-29 | 2002-11-29 | Novel process for preparing alkyl phenol |
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|---|---|
| CN1504445A true CN1504445A (en) | 2004-06-16 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101811945A (en) * | 2010-03-02 | 2010-08-25 | 中国日用化学工业研究院 | Process for preparing alkyl diphenyl ether from fatty alcohol and diphenyl ether |
| CN102658196A (en) * | 2012-04-26 | 2012-09-12 | 凯瑞化工股份有限公司 | Modified clay catalyst and preparation method thereof |
| CN101745423B (en) * | 2008-11-28 | 2012-11-14 | 中国石油化工股份有限公司 | Catalyst and diphenylamine alkylation method |
| CN107162879A (en) * | 2017-06-06 | 2017-09-15 | 常州大学 | A kind of alkali ionic liquid is used for the method for being catalyzed nonene and phenol synthesis nonyl phenol |
-
2002
- 2002-11-29 CN CNA021533407A patent/CN1504445A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101745423B (en) * | 2008-11-28 | 2012-11-14 | 中国石油化工股份有限公司 | Catalyst and diphenylamine alkylation method |
| CN101811945A (en) * | 2010-03-02 | 2010-08-25 | 中国日用化学工业研究院 | Process for preparing alkyl diphenyl ether from fatty alcohol and diphenyl ether |
| CN101811945B (en) * | 2010-03-02 | 2013-09-04 | 中国日用化学工业研究院 | Process for preparing alkyl diphenyl ether from fatty alcohol and diphenyl ether |
| CN102658196A (en) * | 2012-04-26 | 2012-09-12 | 凯瑞化工股份有限公司 | Modified clay catalyst and preparation method thereof |
| CN107162879A (en) * | 2017-06-06 | 2017-09-15 | 常州大学 | A kind of alkali ionic liquid is used for the method for being catalyzed nonene and phenol synthesis nonyl phenol |
| CN107162879B (en) * | 2017-06-06 | 2020-05-26 | 常州大学 | Method for synthesizing nonyl phenol by catalyzing nonene and phenol with alkaline ionic liquid |
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