CN102942454A - Preparation method of 1,1,1-tri(4-hydroxyphenyl)ethane - Google Patents
Preparation method of 1,1,1-tri(4-hydroxyphenyl)ethane Download PDFInfo
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- CN102942454A CN102942454A CN2012104985249A CN201210498524A CN102942454A CN 102942454 A CN102942454 A CN 102942454A CN 2012104985249 A CN2012104985249 A CN 2012104985249A CN 201210498524 A CN201210498524 A CN 201210498524A CN 102942454 A CN102942454 A CN 102942454A
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- CN
- China
- Prior art keywords
- ethane
- preparation
- hydroxybenzene
- phenol
- parahydroxyacet
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 title abstract 3
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims abstract description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 239000012043 crude product Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- RPHYLOMQFAGWCD-UHFFFAOYSA-N ethane;phenol Chemical compound CC.OC1=CC=CC=C1 RPHYLOMQFAGWCD-UHFFFAOYSA-N 0.000 claims description 18
- 229960003742 phenol Drugs 0.000 claims description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000009466 transformation Effects 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000005070 sampling Methods 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000003828 vacuum filtration Methods 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 mercaptan compound Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparation method of 1,1,1-tri(4-hydroxyphenyl)ethane, which comprises the following steps: adding phenol, p-hydroxyacetophenone and catalyst acetic acid into a reaction vessel, heating to 65-75 DEG C while stirring, introducing nitrogen, starting the reaction, removing water, analyzing samples until the conversion rate of p-hydroxyacetophenone is up to higher than 80%, and finishing the reaction; and adding a solvent, stirring, cooling to room temperature, and carrying out vacuum filtration to obtain the 1,1,1-tri(4-hydroxyphenyl)ethane crude product, wherein the mol ratio of the phenol to the p-hydroxyacetophenone is (5-10):1, and the catalyst acetic acid accounts for 0.1-1% of the total weight of the p-hydroxyacetophenone and phenol. In the reaction process for preparing the target product, the high-yield target product can be obtained by using no solvent and slight acetic acid as the catalyst; and in addition, the preparation method provided by the invention has the advantages of short period and low cost.
Description
Technical field
The present invention relates to a kind of 1,1,1-three (4-hydroxybenzene) alkane, particularly 1,1, the preparation method of 1-three (4-hydroxybenzene) ethane.
Background technology
– three (4 – hydroxy phenyl) ethane (THPE) is the trifunctional phenolic compound, can be used as linking agent or the branching agent of multiple polymers (such as polycarbonate, Resins, epoxy, polyarylester, tamanori and coating etc.), also can be used as the intermediate of preparation oxidation inhibitor.In polymer architecture, introduce THPE and can improve a lot of key propertys, such as hardness, thermotolerance, solvent resistance and agglutinating value(of coal) etc., in hyperbranched polymer, introduce THPE, can expand its Application Areas.
In the prior art, THPE normally take 4 – hydroxy acetophenones and phenol as raw material under the hydrogenchloride condition, adopting trichloromethane, methylene dichloride and ethylene dichloride etc. is solvent, make, but this method reaction times is longer, and the by product content of bisphenol A is higher, and solvent loss is large, the yield of products therefrom is lower, and cost is higher.United States Patent (USP) 5,756,781 disclose " making phenol and 4-hydroxyacetophenone in the presence of the ion-exchange catalyst of significant quantity and the mercaptan as co-accelerator " reaction, can obtain being substantially free of 1 of various reaction impurities, 1,1 – three (4 – hydroxy phenyl) ethane.United States Patent (USP) 5,756,781 disclose " making phenol and 2; the 4-diacetylmethane is in the presence of the mercaptan compound as promotor of acidic conditions and significant quantity " reaction, this patent further specifies, " described acidic conditions can obtain by adding any acidic substance, especially relative volatility material such as hydrogenchloride; and usually, hydrogen chloride gas during reaction passes through mixture ".Except other shortcoming, the deficiency of the above the whole bag of tricks is, needs the quantity of the catalyzer that uses higher, and the volatile acid of use such as hydrogen chloride gas are corrosive, and solvent loss is large, and product yield is generally not high.
Summary of the invention
Technical problem to be solved by this invention is to overcome the deficiencies in the prior art, provide a kind of reaction times short, yield is high, cost is low 1,1, the preparation method of 1-three (4-hydroxybenzene) ethane.
For solving above technical problem, the present invention takes following technical scheme:
A kind of 1, the preparation method of 1,1-three (4-hydroxybenzene) ethane, it is with phenol, parahydroxyacet-ophenone and catalyzer acetic acid join in the reaction vessel, stirring is warming up to 65 ~ 75 ℃, pass into nitrogen, begin reaction, remove water, sampling analysis, reach more than 80% to the parahydroxyacet-ophenone transformation efficiency, finish reaction, add stirring solvent, be cooled to room temperature, suction filtration gets 1,1, the crude product of 1-three (4-hydroxybenzene) ethane, wherein, the molar ratio of phenol and parahydroxyacet-ophenone is 5 ~ 10:1, the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.1% ~ 1%.
Further, the molar ratio of phenol and parahydroxyacet-ophenone is preferably 6 ~ 8:1.
Preferably, the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.15% ~ 0.5%.More preferably, the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.15% ~ 0.25%.
According to a concrete aspect, described solvent is dimethylbenzene.
Further, described preparation method comprises that also 1-three (4-hydroxybenzene) crude product of ethane carries out the step of purifying to described 1,1.Purification process can be taked known means of purification.For example, crude product can be contacted 0.5 ~ 2 hour with the methanol-water mixtures that contains at least 20% volumes methanol.Perhaps, when needed, can further, crude product be refluxed in the mixture of the alcohol that comprises discoloring agent; At last, visually colourless 1,1 to be settled out with the optional water treatment that comprises discoloring agent, 1-three (4-hydroxybenzene) ethane.In addition, crude product can also adopt the binding substances crystallization technique to carry out purifying.
Preferably, reach 80% ~ 82% to the parahydroxyacet-ophenone transformation efficiency, finish reaction.Usually, begin to reach 80% to transformation efficiency from reaction, need about 12 hours approximately.
Because the enforcement of above technical scheme, the present invention compared with prior art has following advantage:
The present invention does not use solvent in the reaction process of preparation target product, only adopt a small amount of acetic acid as catalyzer, just can obtain target product by high yield; In addition, preparation method's cycle of the present invention is short, and cost is lower.
Embodiment
The present invention will be further described in detail below in conjunction with specific embodiment.
Embodiment 1
In being housed, 2000 ml four-hole boiling flasks of reflux exchanger, water trap, thermometer, drying tube and stirring add phenol 800g (8.5mol), parahydroxyacet-ophenone 150g (1.1mol) and catalyzer acetic acid 2g, then stir and be warmed up to 70 ± 2 ℃, pass into N
2
Begin reaction, remove water, reacted about 12 hours, sampling analysis, reaction reach and namely finish reaction more than 80%, add solvent xylene 600 g and stir, cool to room temperature, suction filtration is drained, and gets 1,1, the crude product 310g of 1-three (4-hydroxybenzene) ethane, through take the first alcohol and water as solvent, heating for dissolving and decolorizing with activated carbon, filtration, crystallisation by cooling, filter, oven dry gets 1,1, about 1-three (4-hydroxybenzene) ethane 275g, HPLC content is 99.55%, in parahydroxyacet-ophenone, and molar yield about 81.6%.
Embodiment 2
In being housed, 2000 ml four-hole boiling flasks of reflux exchanger, water trap, thermometer, drying tube and stirring add phenol 620g (6.59mol), parahydroxyacet-ophenone 150g (1.1mol) and catalyzer acetic acid 2.3g, then stir and be warmed up to 70 ± 2 ℃, pass into N
2
Begin reaction, remove water, reacted sampling analysis about 12 hours, reaction reaches and namely finishes reaction more than 80%, adds solvent xylene 600 g and stirs cool to room temperature, suction filtration is drained, and gets 1, the crude product 305g of 1,1-three (4-hydroxybenzene) ethane, warp is take the first alcohol and water as solvent, heating for dissolving and decolorizing with activated carbon, filtration, crystallisation by cooling filter, oven dry, get about 1,1,1-three (4-hydroxybenzene) ethane 270g.HPLC content is 99.56%, in parahydroxyacet-ophenone, and molar yield about 80%.
Above-described embodiment only is explanation technical conceive of the present invention and characteristics; its purpose is to allow the personage who is familiar with technique can understand content of the present invention and according to this enforcement; can not limit protection scope of the present invention with this; all equivalences that spirit is done according to the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (7)
1. one kind 1, the preparation method of 1,1-three (4-hydroxybenzene) ethane, it is characterized in that: the method is with phenol, parahydroxyacet-ophenone and catalyzer acetic acid join in the reaction vessel, stirring is warming up to 65 ~ 75 ℃, pass into nitrogen, begin reaction, remove water, sampling analysis, reach more than 80% to the parahydroxyacet-ophenone transformation efficiency, finish reaction, add stirring solvent, be cooled to room temperature, suction filtration gets 1,1, the crude product of 1-three (4-hydroxybenzene) ethane, wherein, the molar ratio of phenol and parahydroxyacet-ophenone is 5 ~ 10:1, the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.1% ~ 1%.
2. according to claim 11,1, the preparation method of 1-three (4-hydroxybenzene) ethane, it is characterized in that: the molar ratio of phenol and parahydroxyacet-ophenone is 6 ~ 8:1.
3. according to claim 11,1, the preparation method of 1-three (4-hydroxybenzene) ethane is characterized in that: the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.15% ~ 0.5%.
4. according to claim 31,1, the preparation method of 1-three (4-hydroxybenzene) ethane is characterized in that: the weight that feeds intake of catalyzer acetic acid be parahydroxyacet-ophenone and phenol gross weight 0.15% ~ 0.25%.
5. according to claim 11,1, the preparation method of 1-three (4-hydroxybenzene) ethane, it is characterized in that: described solvent is dimethylbenzene.
6. according to claim 11,1, the preparation method of 1-three (4-hydroxybenzene) ethane is characterized in that: reach 80% ~ 82% to the parahydroxyacet-ophenone transformation efficiency, finish reaction.
7. according to claim 11,1, the preparation method of 1-three (4-hydroxybenzene) ethane is characterized in that: described preparation method comprises that also 1-three (4-hydroxybenzene) crude product of ethane carries out the step of purifying to described 1,1.
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| CN201210498524.9A CN102942454B (en) | 2012-11-29 | 2012-11-29 | Preparation method of 1,1,1-tri(4-hydroxyphenyl)ethane |
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| CN102942454B CN102942454B (en) | 2014-06-04 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105541561A (en) * | 2016-02-04 | 2016-05-04 | 常州市天华制药有限公司 | Method for synthesizing and purifying 1,1,1-tri(4-hydroxy phenyl) ethane |
| CN111574334A (en) * | 2020-04-16 | 2020-08-25 | 江汉大学 | Novel phenolic compound and preparation method and application thereof |
| CN112062657A (en) * | 2019-06-10 | 2020-12-11 | 太仓市茜泾化工有限公司 | Preparation method of 1,1, 1-tri (4-hydroxyphenyl) ethane |
| CN114573425A (en) * | 2022-03-16 | 2022-06-03 | 安徽觅拓材料科技有限公司 | Purification method and application of 1, 1, 1-tri (4-hydroxyphenyl) compound |
| CN115215734A (en) * | 2022-08-17 | 2022-10-21 | 辽宁靖帆新材料有限公司 | Preparation method of 1- [4- (4-hydroxyphenyl) phenyl ] -1, 1-bis (4-hydroxyphenyl) ethane |
| CN115959977A (en) * | 2022-12-28 | 2023-04-14 | 陕西泰合利华工业有限公司 | Preparation method of 1, 1-tri (3, 5-dimethoxymethyl-4-hydroxyphenyl) ethane |
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2012
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105541561A (en) * | 2016-02-04 | 2016-05-04 | 常州市天华制药有限公司 | Method for synthesizing and purifying 1,1,1-tri(4-hydroxy phenyl) ethane |
| CN105541561B (en) * | 2016-02-04 | 2017-08-15 | 常州市天华制药有限公司 | A kind of synthesis of 1,1,1 3 (4 hydroxy phenyl) ethane and purification process |
| CN112062657A (en) * | 2019-06-10 | 2020-12-11 | 太仓市茜泾化工有限公司 | Preparation method of 1,1, 1-tri (4-hydroxyphenyl) ethane |
| CN112062657B (en) * | 2019-06-10 | 2022-05-24 | 太仓市茜泾化工有限公司 | Preparation method of 1,1, 1-tri (4-hydroxyphenyl) ethane |
| CN111574334A (en) * | 2020-04-16 | 2020-08-25 | 江汉大学 | Novel phenolic compound and preparation method and application thereof |
| CN111574334B (en) * | 2020-04-16 | 2023-02-10 | 江汉大学 | Novel phenolic compound and preparation method and application thereof |
| CN114573425A (en) * | 2022-03-16 | 2022-06-03 | 安徽觅拓材料科技有限公司 | Purification method and application of 1, 1, 1-tri (4-hydroxyphenyl) compound |
| CN115215734A (en) * | 2022-08-17 | 2022-10-21 | 辽宁靖帆新材料有限公司 | Preparation method of 1- [4- (4-hydroxyphenyl) phenyl ] -1, 1-bis (4-hydroxyphenyl) ethane |
| CN115215734B (en) * | 2022-08-17 | 2024-01-05 | 辽宁靖帆新材料有限公司 | Preparation method of 1- [4- (4-hydroxyphenyl) phenyl ] -1, 1-bis (4-hydroxyphenyl) ethane |
| CN115959977A (en) * | 2022-12-28 | 2023-04-14 | 陕西泰合利华工业有限公司 | Preparation method of 1, 1-tri (3, 5-dimethoxymethyl-4-hydroxyphenyl) ethane |
| CN115959977B (en) * | 2022-12-28 | 2024-06-11 | 陕西泰合利华工业有限公司 | Preparation method of 1, 1-tris (3, 5-dimethoxy methyl-4-hydroxyphenyl) ethane |
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| CN102942454B (en) | 2014-06-04 |
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