CN102381993A - Preparation method of 3-(N,N-dimethylamino)phenol - Google Patents
Preparation method of 3-(N,N-dimethylamino)phenol Download PDFInfo
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- CN102381993A CN102381993A CN201110397395XA CN201110397395A CN102381993A CN 102381993 A CN102381993 A CN 102381993A CN 201110397395X A CN201110397395X A CN 201110397395XA CN 201110397395 A CN201110397395 A CN 201110397395A CN 102381993 A CN102381993 A CN 102381993A
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- dimethylamino
- phenol
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- resorcinol
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Abstract
The invention relates to a preparation method of 3-(N,N-dimethylamino)phenol, and belongs to the technical field of fine chemical industry. The method comprises the following steps: reacting dimethylamine aqueous solution and resorcinol to obtain crude 3-(N,N-dimethylamino)phenol, then adding industrial liquid alkali in the crude product, adding toluene to extract by-products, neutralizing the aqueous phase, washing to remove unreacted resorcinol, and performing vacuum distillation to obtain 3-(N,N-dimethylamino)phenol. The method is simple for operations and has high product purity; and the storage and transportation of the raw materials are easy and the industrialized safety production can be performed easily.
Description
Technical field
The present invention relates to the preparation method of a kind of 3-(N, N-dimethylamino) phenol, belong to the fine chemical technology field.
Background technology
3-(N; The N-dimethylamino) phenol is used for synthetic dyestuff and medicine intermediate, and the traditional processing technology of this compound obtains 3-(N through the multistep purifying with Metha Amino Phenon and methyl-sulfate reaction after the reaction again; The N-dimethylamino) phenol; Production technique need be used the methyl-sulfate of severe toxicity, and is very high to safety in production and raw material movement requirement, is unfavorable for suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide the preparation method of a kind of 3-(N, N-dimethylamino) phenol, simple to operate, product purity is high, and raw material is easy to store and transportation, is easy to the industriallization safety in production.
The preparation method of 3-of the present invention (N, N-dimethylamino) phenol at first obtains 3-(N with dimethylamine agueous solution and resorcin reaction; The N-dimethylamino) phenol bullion adds industrial lye then in bullion, add the extracted in toluene by product again; Aqueous phase and after; The intact Resorcinol of unreacted is removed in washing, obtains 3-(N, N-dimethylamino) phenol through underpressure distillation again.
The building-up reactions formula is following:
Wherein:
The mole ratio of Resorcinol and n n dimetylaniline preferably is controlled at 1.0: 1.0～1.5, and temperature of reaction is 160～210 ℃.
The dimethylamine agueous solution mass percentage concentration is preferably 30～50%.
The industrial lye mass percentage concentration is preferably 20～40% aqueous sodium hydroxide solution.
Preferably the material after Resorcinol and the dimethylamine agueous solution reaction completion is cooled to 10～30 ℃, uses the extracted in toluene by product.
Preferably will extract the material behind the by product,, use 50～80 ℃ of hot washes then, underpressure distillation after dividing water with acid for adjusting pH=6～7.
Used acid can be technical hydrochloric acid or dilute sulphuric acid etc.
The present invention compared with prior art has following beneficial effect:
The diverse synthetic route of employing of the present invention and prior art, dimethylamine agueous solution and resorcin reaction are selected in reaction for use, thus the methyl-sulfate that avoids the use of severe toxicity is done raw material; Raw material is easy to store and transportation, is easy to the industriallization safety in production, and bullion is successively removed byproduct of reaction and the intact raw material of unreacted through extracted in toluene and hot wash; Get 3-(N through underpressure distillation again; The N-dimethylamino) phenol, product purity reaches more than 98.0%, reaches more than 40% in the Resorcinol total recovery.Simple to operate, product purity is high.
Embodiment
Below in conjunction with embodiment the present invention is described further.
Embodiment 1
Under the room temperature, be that 36% dimethylamine agueous solution adds in the 2L autoclave with 354g Resorcinol and 450g mass percent concentration in order, be warming up to 175 ℃, insulation to reaction finishes; When material is cooled to 30 ℃ behind the question response, it is transferred to the 5L four-hole bottle, stirs the industrial lye that slowly adds 1142g mass percent concentration concentration 30% down; Be cooled to 20 ℃, 500ml toluene is extracting impurities at twice, and water is transferred PH=6～7 with technical hydrochloric acid; Standing demix, water layer discarded, it is 80 ℃ twice of hot wash that oil reservoir uses the 500ml water temperature; Underpressure distillation is then collected main distillate fraction and is 3-(N, N-dimethylamino) phenol.
Embodiment 2
Under the room temperature, be that 40% dimethylamine agueous solution adds in the 2L autoclave with 354g Resorcinol and 430g mass percent concentration in order, be warming up to 180 ℃, insulation to reaction finishes; When material is cooled to 25 ℃ behind the question response, it is transferred to the 5L four-hole bottle, stirs that slowly to add the 1100g mass percent concentration down be 35% industrial lye; Be cooled to 15 ℃, 600ml toluene is extracting impurities at twice, and water is transferred PH=6～7 with 20% dilute sulphuric acid; Standing demix, water layer discarded, it is 70 ℃ twice of hot wash that oil reservoir uses the 550ml water temperature; Underpressure distillation is then collected main distillate fraction and is 3-(N, N-dimethylamino) phenol.
Embodiment 3
Under the room temperature, be that 45% dimethylamine agueous solution adds in the 2L autoclave with 354g Resorcinol and 420g mass percent concentration in order, be warming up to 190 ℃, insulation to reaction finishes; When material is cooled to 20 ℃ behind the question response, it is transferred to the 5L four-hole bottle, stirs the industrial lye that slowly adds 1120g mass percent concentration concentration 36% down; Be cooled to 30 ℃, 500ml toluene is extracting impurities at twice, and water is transferred PH=6～7 with 30% dilute sulphuric acid; Standing demix, water layer discarded, it is 60 ℃ twice of hot wash that oil reservoir uses the 600ml water temperature; Underpressure distillation is then collected main distillate fraction and is 3-(N, N-dimethylamino) phenol.
Embodiment 4
Under the room temperature, be that 48% dimethylamine agueous solution adds in the 2L autoclave with 354g Resorcinol and 400g mass percent concentration in order, be warming up to 200 ℃, insulation to reaction finishes; When material is cooled to 10 ℃ behind the question response, it is transferred to the 5L four-hole bottle, stirs that slowly to add the 1150g mass percent concentration down be 26% industrial lye; Be cooled to 10 ℃, 600ml toluene is extracting impurities at twice, and water is transferred PH=6～7 with 50% dilute sulphuric acid; Standing demix, water layer discarded, oil reservoir is with twice of the hot wash of 50 ℃ of 700ml water temperatures; Underpressure distillation is then collected main distillate fraction and is 3-(N, N-dimethylamino) phenol.
Claims (6)
1. the preparation method of a 3-(N, N-dimethylamino) phenol is characterized in that at first obtaining 3-(N with dimethylamine agueous solution and resorcin reaction; The N-dimethylamino) phenol bullion adds industrial lye then in bullion, add the extracted in toluene by product again; Aqueous phase and after; The intact Resorcinol of unreacted is removed in washing, obtains 3-(N, N-dimethylamino) phenol through underpressure distillation again.
2. the preparation method of 3-according to claim 1 (N, N-dimethylamino) phenol, the mole ratio that it is characterized in that Resorcinol and n n dimetylaniline is 1.0: 1.0～1.5, temperature of reaction is 160～210 ℃.
3. the preparation method of 3-according to claim 2 (N, N-dimethylamino) phenol is characterized in that the dimethylamine agueous solution mass percentage concentration is 30～50%.
4. the preparation method of 3-according to claim 1 (N, N-dimethylamino) phenol is characterized in that industrial lye is the aqueous sodium hydroxide solution of mass percentage concentration 20～40%.
5. according to the preparation method of claim 1,2,3 or 4 described 3-(N, N-dimethylamino) phenol, it is characterized in that the material after the reaction of Resorcinol and dimethylamine agueous solution is accomplished is cooled to 10～30 ℃, use the extracted in toluene by product.
6. the preparation method of 3-according to claim 5 (N, N-dimethylamino) phenol is characterized in that the material behind the extraction by product with acid for adjusting pH=6～7, is used 50～80 ℃ of hot washes, underpressure distillation after dividing water then.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201110397395XA CN102381993A (en) | 2011-12-02 | 2011-12-02 | Preparation method of 3-(N,N-dimethylamino)phenol |
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| CN201110397395XA CN102381993A (en) | 2011-12-02 | 2011-12-02 | Preparation method of 3-(N,N-dimethylamino)phenol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924304A (en) * | 2012-10-26 | 2013-02-13 | 大连市旅顺口区江西化工工业总公司 | Preparation method of m-dimethylaminophenol |
Citations (5)
| 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 |
| US5710335A (en) * | 1995-10-16 | 1998-01-20 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 3-(N,N-disubstituted amino)phenol |
| JP3311372B2 (en) * | 1992-01-10 | 2002-08-05 | 三井化学株式会社 | Method for producing 3-N, N-dialkylaminophenol derivative |
| CN101486658A (en) * | 2009-02-27 | 2009-07-22 | 康爱特维迅（蓬莱）化学有限公司 | Preparation of 3-(N-ethyl-N-isoamyl) amino phenol |
| CN101671261A (en) * | 2009-10-09 | 2010-03-17 | 寿光富康制药有限公司 | Preparation method of N-alkyl m-aminophenol |
-
2011
- 2011-12-02 CN CN201110397395XA patent/CN102381993A/en active Pending
Patent Citations (5)
| 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 |
| JP3311372B2 (en) * | 1992-01-10 | 2002-08-05 | 三井化学株式会社 | Method for producing 3-N, N-dialkylaminophenol derivative |
| US5710335A (en) * | 1995-10-16 | 1998-01-20 | Mitsui Toatsu Chemicals, Inc. | Process for preparing 3-(N,N-disubstituted amino)phenol |
| CN101486658A (en) * | 2009-02-27 | 2009-07-22 | 康爱特维迅（蓬莱）化学有限公司 | Preparation of 3-(N-ethyl-N-isoamyl) amino phenol |
| CN101671261A (en) * | 2009-10-09 | 2010-03-17 | 寿光富康制药有限公司 | Preparation method of N-alkyl m-aminophenol |
Non-Patent Citations (1)
| Title |
|---|
| 李春波 等: "热敏染料中间体间N ,N -二烷基氨基苯酚的催化合成", 《精细石油化工》, no. 4, 30 April 2002 (2002-04-30), pages 14 - 16 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924304A (en) * | 2012-10-26 | 2013-02-13 | 大连市旅顺口区江西化工工业总公司 | Preparation method of m-dimethylaminophenol |
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Application publication date: 20120321 |