CN1315314A - Process for preparing alkylphenol - Google Patents
Process for preparing alkylphenol Download PDFInfo
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- CN1315314A CN1315314A CN 00103285 CN00103285A CN1315314A CN 1315314 A CN1315314 A CN 1315314A CN 00103285 CN00103285 CN 00103285 CN 00103285 A CN00103285 A CN 00103285A CN 1315314 A CN1315314 A CN 1315314A
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- alkene
- phenol
- alkylphenol
- calcium oxide
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing alkylphenol includes such steps as reaction of C8-C16 olefin with phenol under the action of cationic exchange resin catalyst, removing catalyst, adding calcium oxide (0.1-5 wt.%), optional reaction at 50-150 deg.C for 10-120 min, removing dregs and separating out the olefin and phenol which did not take part in reaction. The resultant alkylphenol features light colour (ASTM 1500 chromaticity is less than or equal to 1), and high chromaticity stability.
Description
The present invention relates to the preparation method of alkylphenol, exactly, is the preparation method of light alkylphenol.
Alkylphenol is a class important chemical material, and for example, 4-dodecylphenol is a raw material of producing calcium sulfenyl phenolate, and calcium sulfenyl phenolate is a kind of important I. C. engine oil purification agent.In the process of preparation alkylphenol, owing to reasons such as the source of alkene, catalyst type, there are the problem of the dark and chromaticity stability difference of color in the alkylphenol product of gained, particularly high carbon number alkylphenol product.And the colourity of alkylphenol and quality directly have influence on the colourity and the quality of the finished product.
It is that raw material, Zeo-karb are the method for Catalyst Production alkylphenol that United States Patent (USP) 4198531 has been reported with oligomerization of propene thing and phenol, and products obtained therefrom is alkylphenol of light color of Catalyst Production than with the carclazyte, but still has the problem of chromaticity stability difference.
The preparation method who the purpose of this invention is to provide two kinds of simple and easy to do light alkylphenols, of light color with the alkylphenol of these two kinds of method preparations, its ASTM 1500 colourities≤1, and store nondiscoloration, chromaticity stability is good.
First method provided by the invention comprises: with C
8～C
16Alkene and phenol are removed catalyzer after reacting under the effect of cation exchange resin catalyst, add the calcium oxide of its weight 0.1～5% in product, separate unreacted alkene and phenol, slagging-off.
Specifically, first method of the present invention can be carried out in the following manner;
1. according to ordinary method, or with reference to United States Patent (USP) 4198531, with C
8～C
16Alkene, preferred C
9～C
14Alkene and phenol react under the effect of cation exchange resin catalyst, remove catalyzer after having reacted, and obtain containing the reaction product of alkylphenol;
2. in the alkylphenol product, add its weight 0.1～5%, preferred 0.3～2% calcium oxide, unreacted alkene and phenol are reclaimed in underpressure distillation;
3. distillation residue are filtered or centrifugal slagging-off, can obtain light alkylphenol product.
Second method provided by the invention comprises: with C
8～C
16Alkene and phenol are removed catalyzer after reacting under the effect of cation exchange resin catalyst, add the calcium oxide of its weight 0.1～5% in product, react 10～120 minutes down at 50～150 ℃, and slagging-off separates unreacted alkene and phenol.
Specifically, second method of the present invention can be carried out in the following manner:
1. according to ordinary method, or with reference to United States Patent (USP) 4198531, with C
8～C
16Alkene, preferred C
9～C
14Alkene and phenol react under the effect of cation exchange resin catalyst, remove catalyzer after having reacted, and obtain containing the reaction product of alkylphenol;
2. in the alkylphenol product, add its weight 0.1～5%, preferred 0.3～2% calcium oxide, under 50～150 ℃, preferred 80～120 ℃ of following stirring reactions 10～120 minutes, preferred 30～60 minutes;
3. filter or centrifugal slagging-off, obtain containing the clear liquid of alkylphenol;
4. with the clear liquid underpressure distillation, reclaim unreacted alkene and phenol, can obtain light alkylphenol product.
Calcium oxide of the present invention, its purity is best 〉=95%, and water content is best≤0.5%, and granularity is best≤80 orders.
The invention has the advantages that: by the chemistry and the physical action of calcium oxide, the impurity that adds lustre in the alkylphenol is removed effectively, improved the discoloration problem and the problems of stability in storage of alkylphenol greatly.The inventive method is simple and easy to do, and is with low cost, and the exhausted calcium oxide is easy to remove by centrifugal or filtering way, can not influence the quality of the finished product.
Further specify characteristics of the present invention below by example.
Example 1
Phenol and tetrapropylene are reacted under the cation exchange resin catalyst effect.Reaction finishes, remove catalyzer after, obtain containing the reaction product of 4-dodecylphenol.The 500g reaction product is put into the 1000mL matrass, add the 1.5g calcium oxide, unreacted phenol and tetrapropylene are reclaimed in decompression distillation down, and the centrifugal slagging-off of residuum obtains weak yellow liquid and is the dodecyl phenolic product.Measuring its chrominance levels with the ASTM1500 method is＜0.5.Product is placed after 6 months and is measured, and its chrominance levels is 0.5.
Example 2
Phenol and tetrapropylene are reacted under the cation exchange resin catalyst effect.Reaction finishes, remove catalyzer after, obtain containing the reaction product of 4-dodecylphenol.The 500g reaction product is put into the 1000mL there-necked flask, add the 2.5g calcium oxide, react 1hr down in 100～110 ℃, then with the reaction product filter cleaner, filtrate places the 1000mL matrass, unreacted phenol and tetrapropylene are reclaimed in decompression distillation down, obtain weak yellow liquid and are the dodecyl phenolic product.Measuring its chrominance levels with the ASTM1500 method is＜1.Product is placed after 6 months and is measured, and its chrominance levels is 1.
Example 3
Phenol and laurylene-1 are reacted under the cation exchange resin catalyst effect.Reaction finishes, remove catalyzer after, obtain containing the reaction product of 4-dodecylphenol.The 500g reaction product is put into the 1000mL matrass, add the 5g calcium oxide, unreacted phenol and tetrapropylene are reclaimed in decompression distillation down, and the centrifugal slagging-off of residuum obtains weak yellow liquid and is the dodecyl phenolic product.Measuring its chrominance levels with the ASTM1500 method is＜1.Product is placed after 6 months and is measured, and its chrominance levels still is＜1.
Comparative Examples
Phenol and tetrapropylene are reacted under the cation exchange resin catalyst effect, obtain containing the reaction product of 4-dodecylphenol.After removing catalyzer, obtain containing the reaction product of 4-dodecylphenol.The 500g reaction product is placed the 1000mL matrass, and unreacted phenol and tetrapropylene are reclaimed in decompression distillation down, obtain yellow liquid and are the dodecyl phenolic product.Measuring its chrominance levels with ASTM 1500 methods is 1.5.Product is placed after 6 months and is measured, and its chrominance levels is＜3.5.
Claims (10)
1. the preparation method of an alkylphenol comprises: with C
8～C
16Alkene and phenol are removed catalyzer after reacting under the effect of cation exchange resin catalyst, add the calcium oxide of its weight 0.1～5% in product, separate unreacted alkene and phenol, slagging-off.
2. in accordance with the method for claim 1, it is characterized in that described alkene is selected from C
9～C
14Alkene.
3. in accordance with the method for claim 1, it is characterized in that the add-on of calcium oxide is 0.3～2%.
4. according to claim 1 or 3 described methods, it is characterized in that described calcium oxide purity 〉=95%, water content≤0.5%, granularity≤80 orders.
5. the preparation method of an alkylphenol comprises: with C
8～C
16Alkene and phenol are removed catalyzer after reacting under the effect of cation exchange resin catalyst, add the calcium oxide of its weight 0.1～5% in product, react 10～120 minutes down at 50～150 ℃, and slagging-off separates unreacted alkene and phenol.
6. in accordance with the method for claim 5, it is characterized in that the add-on of calcium oxide is 0.3～2%.
7. in accordance with the method for claim 5, it is characterized in that temperature of reaction is 80～120 ℃.
8. in accordance with the method for claim 5, it is characterized in that the reaction times is 30～60 minutes.
9. according to claim 5 or 6 described methods, it is characterized in that described calcium oxide purity 〉=95%, water content≤0.5%, granularity≤80 orders.
10. in accordance with the method for claim 5, it is characterized in that described alkene is selected from C
9～C
14Alkene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00103285A CN1102564C (en) | 2000-03-23 | 2000-03-23 | Process for preparing alkylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00103285A CN1102564C (en) | 2000-03-23 | 2000-03-23 | Process for preparing alkylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1315314A true CN1315314A (en) | 2001-10-03 |
| CN1102564C CN1102564C (en) | 2003-03-05 |
Family
ID=4576872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00103285A Expired - Lifetime CN1102564C (en) | 2000-03-23 | 2000-03-23 | Process for preparing alkylphenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1102564C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103725354A (en) * | 2012-10-15 | 2014-04-16 | 中国石油化工股份有限公司 | Preparation method of high-base number sulfurized alkylphenol salt |
| CN112574005A (en) * | 2020-12-23 | 2021-03-30 | 广东新华粤石化集团股份公司 | Preparation method for producing branched-chain dodecylphenol |
| CN116410063A (en) * | 2021-12-31 | 2023-07-11 | 广东锦昱材料科技有限公司 | Heavy component decoloring method in alkylphenol production |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5325526A (en) * | 1976-08-20 | 1978-03-09 | Goi Kasei Kk | Process for preparing alkyl phenol difficultly decolored or free from decoloration with lapse of time |
-
2000
- 2000-03-23 CN CN00103285A patent/CN1102564C/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103725354A (en) * | 2012-10-15 | 2014-04-16 | 中国石油化工股份有限公司 | Preparation method of high-base number sulfurized alkylphenol salt |
| CN103725354B (en) * | 2012-10-15 | 2015-07-01 | 中国石油化工股份有限公司 | Preparation method of high-base number sulfurized alkylphenol salt |
| CN112574005A (en) * | 2020-12-23 | 2021-03-30 | 广东新华粤石化集团股份公司 | Preparation method for producing branched-chain dodecylphenol |
| CN116410063A (en) * | 2021-12-31 | 2023-07-11 | 广东锦昱材料科技有限公司 | Heavy component decoloring method in alkylphenol production |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1102564C (en) | 2003-03-05 |
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Applicant after: China Petrochemical Group Corp. Applicant after: Sinopec Research Institute of Petroleum Processing Applicant before: China Petrochemical Group Corp. Applicant before: Chinese petrochemical industry Research Institute of Petro-Chemical Engineering of group company |
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| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: CHINA PETROCHEMICAL CORPORATION; CHINA PETROLEUM + CHEMICAL CORPORATION, PETROLEUM CHEMICAL ENGINEERING INSTITUTE TO: CHINA PETROCHEMICAL CORPORATION; CHINA PETROCHEMICAL GROUP PETROCHEMICAL SINCE INSTITUTE |
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| C14 | Grant of patent or utility model | ||
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Granted publication date: 20030305 |
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