KR20000047871A - A process for preparing high purity 2,6-diisopropylphenol - Google Patents
A process for preparing high purity 2,6-diisopropylphenol Download PDFInfo
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- KR20000047871A KR20000047871A KR1019990054574A KR19990054574A KR20000047871A KR 20000047871 A KR20000047871 A KR 20000047871A KR 1019990054574 A KR1019990054574 A KR 1019990054574A KR 19990054574 A KR19990054574 A KR 19990054574A KR 20000047871 A KR20000047871 A KR 20000047871A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C37/80—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
Abstract
Description
본 발명은 고순도 2,6-디이소프로필페놀의 정제방법에 관한 것으로서, 더욱 상세하게는 다음 화학식 1로 표시되는 2,6-디이소프로필페놀을 합성 후, 고순도로 정제하는 방법으로, 1차로 무기산을 사용하고 2차로 염기를 사용한 후, 추출용매로 추출하여 효과적으로 고순도 2,6-디이소프로필페놀을 정제할 수 있는 방법에 관한 것이다.The present invention relates to a method for purifying high purity 2,6-diisopropylphenol, and more particularly, to synthesize 2,6-diisopropylphenol represented by the following Chemical Formula 1, and then to purify it with high purity. The present invention relates to a method for effectively purifying high purity 2,6-diisopropylphenol by using an inorganic acid and using a base as a secondary, followed by extraction with an extraction solvent.
화학식 1Formula 1
상기 화학식 1로 표시되는 2,6-디이소프로필 페놀(이하, DIP이라 함)은 현재 마취제로 상용되고 있으며, 이러한 DIP의 정제방법으로 미국특허 제 5,591,311 호에는 NaOH용액에 DIP를 녹이고 온도를 가온하고, 황산, 인산등의 무기산으로 중화하여 유기층을 얻는 방법을 사용하여 정제하였으며, 미국특허 제 5,175,376 호에서는 석유 에테르나 헥산을 사용하여 정제하였으며, 미국특허 제 5,589,598 호에서는 2,6-디이소프로필페놀 벤조에이트 및 KOH를 사용 정제한다.2,6-diisopropyl phenol (hereinafter referred to as DIP) represented by the formula (1) is currently commercially used as an anesthetic, US Patent No. 5,591,311 in the purification method of the DIP in the NaOH solution and warmed the temperature DIP And neutralized with inorganic acids such as sulfuric acid and phosphoric acid to obtain an organic layer, and purified using US Pat. No. 5,175,376 using petroleum ether or hexane, and US Pat. No. 5,589,598 to 2,6-diisopropyl. Purify using phenol benzoate and KOH.
그러나, 상기한 기존의 정제방법들은 DIP 순도가 99.0% 이상 순도를 사용하여 정제를 통해 99.9% 이상을 만들고 있으며, 상기한 정제방법을 통하여 제거되는 물질은 대부분 다음 화학식 2로 표시되는 화합물과 다음 화학식 3으로 표시되는 화합물을 갖게된다.However, the aforementioned conventional purification methods make 99.9% or more through purification using DIP purity of 99.0% or more, and the material removed through the purification method is mostly represented by the following Chemical Formula 2 and the following Chemical Formula: You will have a compound represented by 3.
따라서, 본 발명은 본 발명이 합성한 DIP 90% 이상의 물질을 선행기술과는 달리 산업적으로 생산 가능하고, 고순도로 제조할 수 있는 기술적으로 진보된 발명을 함으로써, 기술적 과제를 해결하여 순도가 99.99% 이상의 DIP를 얻는데 그 목적이 있다.Accordingly, the present invention solves the technical problem by technically advanced invention that can be produced industrially and manufactured with high purity, unlike the prior art, DIP 90% or more material synthesized by the present invention, the purity is 99.99% The purpose is to obtain the above DIP.
본 발명은 90% 이상의 순도를 갖는 2,6-디이소프로필페놀의 정제방법에 있어서, 1차로 무기산을 사용하고 2차로 염기를 사용한 후, 추출용매로 추출한 다음에 다시 증류 또는 -20 ∼ -30℃에서 결정화하는 2,6-디이소프로필페놀의 정제방법을 그 특징으로 한다.The present invention is a method for purifying 2,6-diisopropylphenol having a purity of 90% or more, first using an inorganic acid and second using a base, followed by extraction with an extraction solvent and then distillation or -20 to -30 It is characterized by a method for purifying 2,6-diisopropylphenol crystallized at 占 폚.
또한, 본 발명은 99% 이상의 순도를 갖는 2,6-디이소프로필페놀의 정제방법에 있어서, 1차로 염기를 사용하고 2차로 무기산을 사용한 후, 유기용매로 추출한 다음에 다시 증류 또는 결정화하는 2,6-디이소프로필페놀의 정제방법을 또 다른 특징으로 한다.In addition, the present invention is a method for purifying 2,6-diisopropylphenol having a purity of 99% or more, using a base as the first, and an inorganic acid in the second, followed by extraction with an organic solvent and then distilled or crystallized again. Another characteristic is the method for purifying 6-diisopropylphenol.
이와 같은 본 발명을 더욱 상세히 설명하면 다음과 같다.Referring to the present invention in more detail as follows.
본 발명은 페놀과 프로필렌가스를 pH 1.0 이하의 산성 조건하에서, 200 ∼ 300℃의 고온에서 250 ∼ 450 psi의 압력으로 합성한 2,6-디이소프로필페놀(90% 이상)을 상기 화학식 2로 표시되는 2-이소프로필페놀과 상기 화학식 3으로 표시되는 2,4,6-트리이소프로필페놀로부터 정제하여 2,6-디이소프로필페놀이 99%이상의 순도를 지닌 제품을 얻을 수 있다.In the present invention, 2,6-diisopropylphenol (90% or more) obtained by synthesizing phenol and propylene gas at a pressure of 250 to 450 psi at a high temperature of 200 to 300 ° C under acidic conditions of pH 1.0 or less is represented by Formula 2 above. Purification from the 2-isopropylphenol represented and the 2,4,6-triisopropylphenol represented by the formula (3) can obtain a product having a purity of 99% or more 2,6-diisopropylphenol.
특히, 본 발명은 90%이상 2,4-디이소프로필페놀중에 존재하는 2-이소프로필페놀, 2,4,6-트리이소프로필페놀을 제거하기 위해 1 ∼ 10N 농도의 무기산(HCl, H2SO4, H3PO4중에서 선택된 것)을 가하여 상온에서 1 ∼ 3시간 동안 교반하고 층분리하여 유기층을 얻고 물층은 폐기한다. 이때 가끔 물로 1 ∼ 2회 세척할 수도 있다.In particular, the present invention is to remove the 2-isopropylphenol, 2,4,6-triisopropylphenol present in 2,4-diisopropylphenol of 90% or more inorganic acids (HCl, H 2 concentration of 1 ~ 10N) SO 4 , H 3 PO 4 ) is added, stirred at room temperature for 1 to 3 hours, layered to obtain an organic layer, and the water layer is discarded. At this time, sometimes it may be washed once or twice with water.
그 다음에 염기(NaOH, KOH, LiOH, Ca(OH)2, Mg(OH)2, Al(OH)3중에서 선택된 것)를 1 ∼ 10%로 만들어 pH를 9 ∼ 12로 조절한 후, 상온에서 1 ∼ 3시간 동안 교반한 다음에 층분리하여 물층은 제거하고 유기층을 취한 후, 추출용매(석유에테르, n-헥산, 사염화탄소, 클로로포름, 메틸렌클로라이드 중에서 선택된 것)를 가하여 녹인 다음에 다시 잔류 물층을 제거하고, Na2SO4로 건조한 후 다단계 증류를 하거나 -20 ∼ -30℃로 결정화하여 순도 99.99% 이상의 2,4-디이소프로필페놀을 얻는다.Then, the base (NaOH, KOH, LiOH, Ca (OH) 2 , Mg (OH) 2 , Al (OH) 3 ) to 1 to 10% to adjust the pH to 9 to 12, then room temperature After stirring for 1 to 3 hours, the layers were separated and the water layer was removed, and the organic layer was taken. Then, an extraction solvent (selected from petroleum ether, n-hexane, carbon tetrachloride, chloroform, and methylene chloride) was added to dissolve and the remaining water layer was again dissolved. The reaction mixture was removed, dried over Na 2 SO 4, and then subjected to multi-step distillation or crystallization at −20 to −30 ° C. to obtain 2,4-diisopropylphenol having a purity of 99.99% or more.
또한, 본 발명은 99% 이상의 순도를 갖는 2,6-디이소프로필페놀을 염기(KOH, LiOH, Ca(OH)2, Mg(OH)2중에서 선택된 것)에 녹이고 무기산(HCl, H2SO4, H3PO4중에서 선택된 것)으로 pH를 2 ∼ 7까지 내린 후, 층분리하여 물층은 폐기하고 유기층에 추출용매(석유에테르, n-헥산 중에서 선택된 것)를 가하여 증류 또는 결정화하여 정제한다.The present invention also dissolves 2,6-diisopropylphenol having a purity of 99% or more in a base (selected from KOH, LiOH, Ca (OH) 2 , Mg (OH) 2 ) and inorganic acids (HCl, H 2 SO 4 , H 3 PO 4 ) to lower the pH to 2-7, the layers are separated and the water layer is discarded, and an organic solvent is selected by distillation or crystallization by adding an extraction solvent (petroleum ether, n-hexane). .
이하 본 발명을 실시예에 의거 더욱 상세히 설명하겠는 바, 본 발명이 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited by Examples.
실시예 1Example 1
91.5% (v/v) 2,4-디이소프로필페놀, 2.5%(v/v) 2-이소프로필페놀, 1%(v/v) 페놀, 5%(v/v) 2,4,6-트리이소프로필페놀을 포함한 반응액 10ℓ에 2N 염산 10ℓ를 가하고 상온에서 1 시간 동안 교반후 층분리하여 유기층을 취하고, 다시 유기층에 1N-NaOH 용액을 가하면서 pH 10.0으로 맞춘다. 상온에서 1 시간 동안 교반하고 다시 유기층을 취한 후 노말 헥산 10ℓ을 가하여 잔유물층을 제거한 후 Na2SO4로 건조시킨후 증류하여 99.99% 이상의 2,4-디이소프로필페놀을 8.2ℓ(89.6%) 얻었다.91.5% (v / v) 2,4-diisopropylphenol, 2.5% (v / v) 2-isopropylphenol, 1% (v / v) phenol, 5% (v / v) 2,4,6 -10 L of 2N hydrochloric acid was added to 10 L of the reaction solution containing triisopropylphenol, stirred for 1 hour at room temperature, separated by layers, and the organic layer was taken. Then, 1N-NaOH solution was added to the organic layer and adjusted to pH 10.0. After stirring for 1 hour at room temperature, the organic layer was again taken up, 10 liters of normal hexane was added to remove the residue layer, dried over Na 2 SO 4 , and distilled to give 8.29.99 (89.6%) of 2,4-diisopropylphenol of 99.99% or more. Got it.
실시예 2Example 2
상기 실시예 1과 동일한 방법으로 건조제 Na2SO4로 건조시킨후 -25℃에서 하루동안 결정화하고, 여과후 얻은 2,4-디이소프로필페놀을 증류하여 99.99%이상의 2,4-디이소프로필페놀을 6.5ℓ(71%) 얻었다.After drying with the drying agent Na 2 SO 4 in the same manner as in Example 1 and crystallization at -25 ℃ for one day, distilled 2,4-diisopropylphenol obtained after filtration to more than 99.99% 2,4-diisopropyl 6.5 liters (71%) of phenol were obtained.
실시예 3Example 3
상기 실시예 1과 동일한 반응액에 2N 염산 10ℓ를 가하고 상온에서 1 시간 동안 교반후 층분리하여 유기층을 취하고, 다시 2N-KOH 용액으로 pH를 9.5로 맞춘 후 상온에서 1 시간 동안 교반하고 다시 유기층을 취한후, 석유에테르 10ℓ를 가하고 잔유물층은 폐기한 다음, MgSO4로 건조후 증류하여 99.99% 이상의 2,4-디이소프로필페놀을 7.95ℓ(86.9%) 얻었다.10 L of 2N hydrochloric acid was added to the same reaction solution as in Example 1, the mixture was stirred at room temperature for 1 hour, and the layers were separated. Then, the pH was adjusted to 9.5 with 2N-KOH solution, stirred at room temperature for 1 hour, and the organic layer was again After the addition, 10 l of petroleum ether was added, the residue layer was discarded, dried over MgSO 4 , and distilled to obtain 7.95 l (86.9%) of 2,4-diisopropylphenol of 99.99% or more.
실시예 4Example 4
상기 실시예 3에서 얻은 방법으로 석유에테르층을 MgSO4로 건조후 -25℃에서 하루동안 결정화한 다음, 여과하고 증류하여 순도 99.99%이상의 2,4-디이소프로필페놀을 6.20ℓ(67.8%) 얻었다.The petroleum ether layer was dried with MgSO 4 in the method obtained in Example 3, and then crystallized at -25 ° C. for one day, filtered and distilled to give 6.20 L (67.8%) of 2,4-diisopropylphenol having a purity of 99.99% or more. Got it.
실시예 5Example 5
상기 실시예 1과 동일한 반응액에 5N 염산 5ℓ를 가하여 상온에서 1 시간 동안 교반후 층분리하여 유기층을 취하고, 다시 2N-LiOH 용액으로 pH을 10.0으로 맞춘 후 상온에서 1 시간 동안 교반 후 다시 유기층을 취하여, n-헥산 10ℓ를 가한후 잔유물층을 폐기한다. Na2SO4로 건조한후 증류하여 99.99%이상의 2,4-디이소프로필페놀을 7.65ℓ(83.5%) 얻었다.5 L hydrochloric acid was added to the same reaction solution as in Example 1, stirred at room temperature for 1 hour, and then the layers were separated. The pH was adjusted to 10.0 with 2N-LiOH solution, and then stirred at room temperature for 1 hour, and then again the organic layer. 10 liters of n-hexane are added and the residue layer is discarded. Drying with Na 2 SO 4 and distillation gave more than 99.99% of 2,4-diisopropylphenol, 7.65 L (83.5%).
실시예 6Example 6
상기 실시예 5에서 얻은 n-헥산층을 Na2SO4로 건조후 증류하지 않고 -25℃에서 결정화하고, 결정을 녹인후 재증류하여 순도 99.99% 이상의 2,4-디이소프로필페놀을 5.75ℓ(62.8%) 얻었다.The n-hexane layer obtained in Example 5 was dried with Na 2 SO 4 and then crystallized at -25 ° C without distillation, and the crystals were dissolved and re-distilled to give 5.75 L of 2,4-diisopropylphenol having a purity of 99.99% or more. (62.8%).
실시예 7Example 7
상기 실시예 1과 동일한 방법으로 정제하고, 염기만 2N-NaOH 대신에 2N-Mg(OH)2를 사용하여 99.99% 이상의 2,4-디이소프로필페놀을 7.45ℓ(81.3%) 얻었다.Purification was carried out in the same manner as in Example 1, to obtain not less than 99.99% of 2,4-diisopropylphenol by using 2N-Mg (OH) 2 instead of 2N-NaOH as the base, and 7.45 L (81.3%).
실시예 8Example 8
상기 실시예 1과 동일한 방법으로 정제하고, 염기만 2N-NaOH 대신에 2N-Ca(OH)2를 사용하여 99.99% 이상의 2,4-디이소프로필페놀을 5.98ℓ(65.3%) 얻었다.Purification was carried out in the same manner as in Example 1, to obtain not less than 99.99% of 2,4-diisopropylphenol by using 2N-Ca (OH) 2 instead of 2N-NaOH as a base.
실시예 9Example 9
99%(v/v) 2,6-디이소프로필페놀 10ℓ을 5% LiOH에 녹여 pH를 11.0으로 맞추고 1시간 동안 교반후, 2N-HCl로 pH를 5.0으로 내린후 유기층을 층분리로 취하고, n-헥산 10ℓ를 가하여 잔유물층은 폐기한 후 Na2SO4로 건조시키고, -25℃에서 하루동안 결정화시켜 99.99% 이상의 2,6-디이소프로필페놀 8.5ℓ(85%)를 얻었다.Dissolve 10 l of 99% (v / v) 2,6-diisopropylphenol in 5% LiOH, adjust the pH to 11.0 and stir for 1 hour, lower the pH to 5.0 with 2N-HCl, and take the organic layer by layer separation. After adding 10 L of n-hexane, the residue layer was discarded, dried over Na 2 SO 4 , and crystallized at -25 ° C. for one day to obtain 8.5 L (85%) of 2,6-diisopropylphenol of 99.99% or more.
실시예 10Example 10
상기 실시예 9와 동일한 방법에서 염기를 KOH를 사용하여 99.99% 이상의 2,6-디이소프로필페놀 8.7ℓ(87%)를 얻었다.In the same manner as in Example 9, 8.7 L (87%) of 2,6-diisopropylphenol of 99.99% or more was obtained using KOH as a base.
따라서, 본 발명은 지금까지 알려진 2,6-디이소프로필페놀의 정제방법과는 달리 산업적으로 생산이 가능하게 하여 고순도로 제조함으로써 그 어느기술보다도 경쟁력을 갖고 대량 생산을 가능케하는 장점이 있다.Therefore, the present invention, unlike the purification method of 2,6-diisopropylphenol, which has been known so far, can be industrially produced and manufactured with high purity, thereby having a competitive advantage over any technology and enabling mass production.
Claims (8)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019990054574A KR20000047871A (en) | 1998-12-04 | 1999-12-02 | A process for preparing high purity 2,6-diisopropylphenol |
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| KR1019980053200 | 1998-12-04 | ||
| KR1019990054574A KR20000047871A (en) | 1998-12-04 | 1999-12-02 | A process for preparing high purity 2,6-diisopropylphenol |
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| Publication Number | Publication Date |
|---|---|
| KR20000047871A true KR20000047871A (en) | 2000-07-25 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019990054574A KR20000047871A (en) | 1998-12-04 | 1999-12-02 | A process for preparing high purity 2,6-diisopropylphenol |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5589598A (en) * | 1994-09-28 | 1996-12-31 | Zambon Group S.P.A. | Process of purification of 2,6-diisopropylphenol |
| US5591311A (en) * | 1995-10-26 | 1997-01-07 | Albemarle Corporation | Process for purifying a 2,6-dialkylphenol |
| US5696300A (en) * | 1994-07-01 | 1997-12-09 | Archimica Spa | Propofol purification |
| KR19990080228A (en) * | 1998-04-14 | 1999-11-05 | 김권 | New Purification Method of 2, 6-dialkyl Phenolic Compounds |
| WO2000034218A1 (en) * | 1998-12-04 | 2000-06-15 | Dong Kook Pharmaceutical Co., Ltd. | Process for purification of 2,6-diisopropyl phenol |
-
1999
- 1999-12-02 KR KR1019990054574A patent/KR20000047871A/en not_active Application Discontinuation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696300A (en) * | 1994-07-01 | 1997-12-09 | Archimica Spa | Propofol purification |
| US5589598A (en) * | 1994-09-28 | 1996-12-31 | Zambon Group S.P.A. | Process of purification of 2,6-diisopropylphenol |
| US5591311A (en) * | 1995-10-26 | 1997-01-07 | Albemarle Corporation | Process for purifying a 2,6-dialkylphenol |
| KR19990080228A (en) * | 1998-04-14 | 1999-11-05 | 김권 | New Purification Method of 2, 6-dialkyl Phenolic Compounds |
| WO2000034218A1 (en) * | 1998-12-04 | 2000-06-15 | Dong Kook Pharmaceutical Co., Ltd. | Process for purification of 2,6-diisopropyl phenol |
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