CN101486658B - Preparation of 3-(N-ethyl-N-isoamyl) amino phenol - Google Patents
Preparation of 3-(N-ethyl-N-isoamyl) amino phenol Download PDFInfo
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- CN101486658B CN101486658B CN2009100143998A CN200910014399A CN101486658B CN 101486658 B CN101486658 B CN 101486658B CN 2009100143998 A CN2009100143998 A CN 2009100143998A CN 200910014399 A CN200910014399 A CN 200910014399A CN 101486658 B CN101486658 B CN 101486658B
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- Prior art keywords
- phenol
- sodium hydroxide
- ethyl
- monoethylamine
- aqueous solution
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- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims abstract description 28
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- TVKZDKSHNITMRZ-UHFFFAOYSA-N 3-(ethylamino)phenol Chemical compound CCNC1=CC=CC(O)=C1 TVKZDKSHNITMRZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 229960001755 resorcinol Drugs 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- JXSJOLURQPNJKW-UHFFFAOYSA-N [Na].C(C)NC=1C=C(C=CC1)O Chemical compound [Na].C(C)NC=1C=C(C=CC1)O JXSJOLURQPNJKW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- -1 bromo iso-pentane Chemical compound 0.000 claims description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 5
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000013067 intermediate product Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 238000009413 insulation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CYHHXZCPTKEZMC-UHFFFAOYSA-N 3-(3-methylbutylamino)phenol Chemical compound CC(C)CCNC1=CC=CC(O)=C1 CYHHXZCPTKEZMC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for 3-(N-ethyl-N-isoamyl) aminophenol. An ethylamine aqueous solution is used for reacting with resorcinol to obtain 3-ethylamino phenol; the obtained 3-ethylamino phenol is added with industrial 30% sodium hydroxide aqueous solution and industrial solid sodium hydroxide to produce a sodium salt, and then added with industrial hydrochloric acid for acidification in order to obtain pure 3-ethylamino phenol; and the purified 3-ethylamino phenol reacts with isoamyl bromide to obtain 3-(N-ethyl-N-isoamyl) aminophenol. The preparation method is characterized by reaction raw materials with low prices, requiring no catalyst, intermediate product adopting the method of purifying by salt, simple operation, good crystallization state, high purity and being easy for industrialized production.
Description
Technical field
The invention belongs to the fine chemical technology field, especially relate to the preparation method of a kind of 3-(N-ethyl-N-isopentyl) amino-phenol.
Background technology
3-(N-ethyl-N-isopentyl) amino-phenol is the key intermediate that is used for synthetic Material of Fluoran heat sensitive dye S205, the traditional synthesis of this intermediate is reacted in the presence of catalyzer with Resorcinol and isobutylcarbylamine, reaction after product 3-isoamylamino phenol ethylizes again, obtains 3-(N-ethyl-N-isopentyl) amino-phenol.But this production technique cost is higher, needs to add catalyzer in reaction process, complicated operation, and the EPA purity that obtains is not high, is unfavorable for suitability for industrialized production.
Summary of the invention
The objective of the invention is to improve the deficiency of prior art and provide a kind of reaction raw materials cheap, do not need catalyzer, intermediate product adopt the salify purifying method, simple to operate, crystal habit good, purity is high, be easy to the preparation method of 3-(N-ethyl-N-isopentyl) amino-phenol of suitability for industrialized production.
The object of the present invention is achieved like this, the preparation method of 3-(N-ethyl-N-isopentyl) amino-phenol, be characterized in obtaining 3-ethylamino phenol with the monoethylamine aqueous solution and resorcin reaction, after adding industrial 30% aqueous sodium hydroxide solution and industrial solid sodium hydroxide generation sodium salt in the 3-ethylamino phenol that obtains, and then adding the 3-ethylamino phenol that the technical hydrochloric acid acidifying obtains purifying, the 3-ethylamino phenol behind the purifying obtains 3-(N-ethyl-N-isopentyl) amino-phenol with the reaction of bromo iso-pentane again.
In order further to realize purpose of the present invention need not to add catalyzer in the time of can being Resorcinol and monoethylamine reactant aqueous solution, temperature of reaction is 160～200 ℃.
In order further to realize purpose of the present invention, can be that raw materials used ratio of components is: the ratio of the mole number of the monoethylamine in Resorcinol, the monoethylamine aqueous solution, industrial 30% aqueous sodium hydroxide solution, industrial solid sodium hydroxide be 1: 0.5～2.0: 0.5～4.0: 0.5～4.0.
In order further to realize purpose of the present invention, can be that material after Resorcinol and monoethylamine reactant aqueous solution are finished is reduced to below 50 ℃, add industrial 30% aqueous sodium hydroxide solution and industrial solid sodium hydroxide, continue to be cooled to 0～10 ℃, filter, get 3-ethylamino phenol sodium salt.
In order further to realize purpose of the present invention, it can be 3-ethylamino phenol sodium salt with prepared in reaction, need not branch water after transferring PH=6～7 with technical hydrochloric acid, with the bromo iso-pentane 80～90 ℃ of reactions down, after minute water, vacuum hydro-extraction, obtain product 3-(N-ethyl-N-isopentyl) amino-phenol.
Compared with the prior art the present invention has following distinguishing feature and positively effect: the diverse synthetic route of employing of the present invention and prior art, and the monoethylamine aqueous solution and resorcin reaction cheap and easy to get are selected in the first step reaction for use, need not to add catalyzer; The first step reaction product 3-ethylamino phenol purifying adopts salifiable method, and is simple to operate; 3-ethylamino sodium phenylate salt refining post crystallization form is good, and the purity height is easy to industrialization.Its synthetic route is as follows:
Adopt the inventive method have reaction raw materials cheap, do not need catalyzer, intermediate product adopt the salify purifying method, simple to operate, crystal habit good, purity is high, be easy to the characteristics of suitability for industrialized production.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail.
Embodiment 1, the preparation method of 3-(N-ethyl-N-isopentyl) amino-phenol, be at room temperature, be that 65% the monoethylamine aqueous solution adds in the 250ml autoclave in turn with 77g Resorcinol and 53g content, be warming up to 165～175 ℃, insulation to reaction finishes, when material is cooled to 40 ℃ behind the question response, it is transferred in the beaker, slowly adds 80ml content 30% liquid caustic soda under stirring, promptly contain sodium hydroxide 0.8mol, add the back and add 25g sheet alkali, continue to be cooled to 0～10 ℃, filter, get about the about 160g of 3-ethylamino phenol sodium salt; Under the room temperature 50ml water is added the 1000ml flask, stir and add 3-ethylamino phenol sodium salt 160g down, be warming up to 80 ℃ after transferring PH=6～7 with technical hydrochloric acid, drip 95g bromo iso-pentane, insulation reaction, after reaction finishes, divide the sub-cloud water layer, wash once, the underpressure distillation dehydration, get product 3-(N-ethyl-N-isopentyl) the about 100g of amino-phenol, content is more than 95.0%.
Embodiment 2, and the preparation method of 3-(N-ethyl-N-isopentyl) amino-phenol is at room temperature, be that 60% ethylamine solution adds in the 250ml autoclave in turn with 77g Resorcinol and 58g content, be warming up to 180 ℃, insulation to reaction finishes, when material is cooled to 30 ℃ behind the question response, it is transferred in the beaker, slowly add 100ml content 30% liquid caustic soda under stirring, add the back and add 30g sheet alkali, continue to be cooled to 0～10 ℃, filter, get about the about 160g of 3-ethylamino phenol sodium salt; Under the room temperature 50ml water is added the 1000ml flask, stir and add anterior reaction product 3-ethylamino phenol sodium salt 160g down, be warming up to 80 ℃ after transferring PH=6～7 with technical hydrochloric acid, drip 150g bromo iso-pentane, insulation reaction, after reaction finishes, divide the sub-cloud water layer, wash once, the underpressure distillation dehydration, get product 3-(N-ethyl-N-isopentyl) the about 100g of amino-phenol, content is more than 95.0%.
Claims (1)
- The preparation method of (1.3-N-ethyl-N-isopentyl) amino-phenol, it is characterized in that obtaining 3-ethylamino phenol with the monoethylamine aqueous solution and resorcin reaction, need not to add catalyzer when Resorcinol and monoethylamine reactant aqueous solution, temperature of reaction is 160～200 ℃, material after Resorcinol and monoethylamine reactant aqueous solution are finished is reduced to below 50 ℃, add industrial 30% aqueous sodium hydroxide solution and industrial solid sodium hydroxide, continue to be cooled to 0～10 ℃, filter, get 3-ethylamino phenol sodium salt, need not branch water after transferring pH=6～7 with technical hydrochloric acid, obtain the 3-ethylamino phenol of purifying, react down at 80～90 ℃ with the bromo iso-pentane, through minute water, washing, obtain product 3-(N-ethyl-N-isopentyl) amino-phenol after the underpressure distillation dehydration, wherein raw materials used ratio of components is: Resorcinol, monoethylamine in the monoethylamine aqueous solution, sodium hydroxide in industry 30% aqueous sodium hydroxide solution, the ratio of the mole number of industrial solid sodium hydroxide is 1: 0.5～2.0: 0.5～4.0: 0.5～4.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100143998A CN101486658B (en) | 2009-02-27 | 2009-02-27 | Preparation of 3-(N-ethyl-N-isoamyl) amino phenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100143998A CN101486658B (en) | 2009-02-27 | 2009-02-27 | Preparation of 3-(N-ethyl-N-isoamyl) amino phenol |
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| Publication Number | Publication Date |
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| CN101486658A CN101486658A (en) | 2009-07-22 |
| CN101486658B true CN101486658B (en) | 2011-11-16 |
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| CN2009100143998A Active CN101486658B (en) | 2009-02-27 | 2009-02-27 | Preparation of 3-(N-ethyl-N-isoamyl) amino phenol |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102199097A (en) * | 2011-04-12 | 2011-09-28 | 烟台大学 | Method for preparing 3-(N-ethyl-N-isoamyl) aminophenol |
| CN102381993A (en) * | 2011-12-02 | 2012-03-21 | 青岛俪徕精细化工有限公司 | Preparation method of 3-(N,N-dimethylamino)phenol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0402935A2 (en) * | 1989-06-16 | 1990-12-19 | Mitsui Petrochemical Industries, Ltd. | Method of producing N-alkylaminophenols |
| US5245081A (en) * | 1991-05-23 | 1993-09-14 | Basf Aktiengesellschaft | Preparation of n,n-disubstituted m-aminophenols |
| US5442121A (en) * | 1993-03-19 | 1995-08-15 | Mitsui Petrochemical Industries Ltd. | Process for producing N,N-disubstituted aminophenol |
| US5710335A (en) * | 1995-10-16 | 1998-01-20 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 3-(N,N-disubstituted amino)phenol |
-
2009
- 2009-02-27 CN CN2009100143998A patent/CN101486658B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0402935A2 (en) * | 1989-06-16 | 1990-12-19 | Mitsui Petrochemical Industries, Ltd. | Method of producing N-alkylaminophenols |
| US5245081A (en) * | 1991-05-23 | 1993-09-14 | Basf Aktiengesellschaft | Preparation of n,n-disubstituted m-aminophenols |
| US5442121A (en) * | 1993-03-19 | 1995-08-15 | Mitsui Petrochemical Industries Ltd. | Process for producing N,N-disubstituted aminophenol |
| US5710335A (en) * | 1995-10-16 | 1998-01-20 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 3-(N,N-disubstituted amino)phenol |
Non-Patent Citations (1)
| Title |
|---|
| 陈厚凯等.热敏染料3-(N-乙基-N-异戊基)氨基-6-甲基-7-苯胺基荧烷的制备.《染料工业》.1997,第34卷(第6期),19-24,47. * |
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| CN101486658A (en) | 2009-07-22 |
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Denomination of invention: Preparation of 3 - (N-ethyl-N-isopentyl) aminophenol Effective date of registration: 20221104 Granted publication date: 20111116 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: Connect Wilson (Penglai) Chemical Co.,Ltd. Registration number: Y2022980020747 |
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Date of cancellation: 20231212 Granted publication date: 20111116 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: Connect Wilson (Penglai) Chemical Co.,Ltd. Registration number: Y2022980020747 |