JPH0585978A - Production of 2-substituted 6-isopropylnaphthalene - Google Patents
Production of 2-substituted 6-isopropylnaphthaleneInfo
- Publication number
- JPH0585978A JPH0585978A JP3251992A JP25199291A JPH0585978A JP H0585978 A JPH0585978 A JP H0585978A JP 3251992 A JP3251992 A JP 3251992A JP 25199291 A JP25199291 A JP 25199291A JP H0585978 A JPH0585978 A JP H0585978A
- Authority
- JP
- Japan
- Prior art keywords
- naphthol
- isopropylnaphthalene
- reaction
- substituted
- type zeolite
- 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.)
- Pending
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は２位置換６−イソプロピ
ルナフタレン、特に、６−イソプロピル−２−ナフトー
ル又は２−メトキシ−６−イソプロピルナフタレンの製
造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing 2-substituted 6-isopropylnaphthalene, particularly 6-isopropyl-2-naphthol or 2-methoxy-6-isopropylnaphthalene.
【０００２】[0002]
【従来の技術】６−イソプロピル−２−ナフトールや２
−メトキシ−６−イソプロピルナフタレンは、解熱鎮痛
消炎剤であるナプロキセンの重要な前駆体である。従
来、ナフタレンやアルキルナフタレンをゼオライトの存
在下にプロピレンにてイソプロピル化してジアルキルナ
フタレンを得ることは、例えば、特開昭６３−２３０６
４５号公報に記載されているように、既に知られてい
る。また、イソプロピル化剤としてイソプロピルアルコ
ールを用いる方法も、例えば、特開昭６３−１４７３８
号公報に記載されているように、既に知られている。2. Description of the Related Art 6-isopropyl-2-naphthol and 2
-Methoxy-6-isopropylnaphthalene is an important precursor of naproxen, an antipyretic analgesic and anti-inflammatory agent. Conventionally, naphthylation of naphthalene or alkylnaphthalene with propylene in the presence of zeolite to obtain dialkylnaphthalene is described, for example, in JP-A-63-2306.
It is already known as described in Japanese Patent Publication No. 45-45. A method using isopropyl alcohol as an isopropylating agent is also disclosed in, for example, JP-A-63-14738.
It is already known as described in the publication.
【０００３】しかし、上記したような２位置換６−イソ
プロピルナフタレンの工業的に有利な製造方法は知られ
ていない。However, an industrially advantageous method for producing the 2-substituted 6-isopropylnaphthalene as described above is not known.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、２−ナフト
ール又は２−メトキシナフタレンを温和な条件下にイソ
プロピル化して、それぞれ６−イソプロピル−２−ナフ
トール又は２−メトキシ−６−イソプロピルナフタレン
を製造する方法を提供することを目的とする。DISCLOSURE OF THE INVENTION In the present invention, 2-naphthol or 2-methoxynaphthalene is isopropylated under mild conditions to produce 6-isopropyl-2-naphthol or 2-methoxy-6-isopropylnaphthalene, respectively. The purpose is to provide a method of doing.
【０００５】[0005]
【課題を解決するための手段】本発明による２位置換６
−イソプロピルナフタレンの製造方法は一般式（Ｉ）2-position substitution 6 according to the present invention
-Isopropylnaphthalene is produced by the general formula (I)
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】（式中、Ｒは水素原子又はメチル基を示
す。）で表わされる２位置換ナフタレンをＹ型ゼオライ
トの存在下にプロピレンにてイソプロピル化することを
特徴とする。本発明の方法において用いる原料物質は、
前記一般式（Ｉ）で表わされる２位置換ナフタレン、即
ち、２−ナフトール又は２−メトキシナフタレンであ
る。A 2-position-substituted naphthalene represented by the formula (wherein R represents a hydrogen atom or a methyl group) is isopropylated with propylene in the presence of a Y-type zeolite. The raw material used in the method of the present invention is
It is a 2-substituted naphthalene represented by the general formula (I), that is, 2-naphthol or 2-methoxynaphthalene.
【０００８】本発明の方法においては、触媒の存在下に
プロピレンをイソプロピル化剤として用いてかかる原料
物質がイソプロピル化される。プロピレンは、上記原料
物質に対して、モル比にて0.３以上の範囲で用いられ
る。上限は特に限定されるものではないが、実用上、８
０程度である。また、前記触媒としては、Ｙ型ゼオライ
ト又は超安定Ｙ型ゼオライトが用いられる。特に後者が
好ましい。かかる触媒は、上記原料物質に対して、通
常、0.００１〜２００重量％、好ましくは0.１〜６０重
量％の範囲で用いられる。In the process of the present invention, such a raw material is isopropylated using propylene as an isopropylating agent in the presence of a catalyst. Propylene is used in a molar ratio of 0.3 or more with respect to the raw material. Although the upper limit is not particularly limited, it is practically 8
It is about 0. Further, as the catalyst, Y-type zeolite or ultra-stable Y-type zeolite is used. The latter is particularly preferable. Such a catalyst is usually used in the range of 0.001 to 200% by weight, preferably 0.1 to 60% by weight, based on the above raw material.
【０００９】反応は、通常、液相にて１〜１５０気圧の
圧力下に、通常、４０〜２５０℃、好ましくは８０〜１
６０℃の範囲で５分乃至２４時間、好ましくは３０分乃
至１０時間行なわれる。反応には、必要に応じて、反応
溶剤が用いられる。反応溶剤としては、例えば、ペンタ
ン、ヘキサン、ヘプタン、オクタン、ノナン、デカン、
デカリン等の脂肪族炭化水素が好適に用いられる。The reaction is usually carried out in the liquid phase under a pressure of 1 to 150 atm, usually 40 to 250 ° C., preferably 80 to 1
It is carried out at 60 ° C. for 5 minutes to 24 hours, preferably 30 minutes to 10 hours. A reaction solvent is used for the reaction, if necessary. Examples of the reaction solvent include pentane, hexane, heptane, octane, nonane, decane,
Aliphatic hydrocarbons such as decalin are preferably used.
【００１０】[0010]
【実施例】以下に実施例を挙げて本発明を説明するが、
本発明はこれら実施例により何ら限定されるものではな
い。 実施例１ ２−ナフトール1.５ｇ、ｎ−ヘキサン６ml及び超安定Ｙ
型ゼオライト（東ソー（株）製Ｈ−ＵＳＹ（ＴＳＺ３３
０）0.３０ｇからなる混合物を５０ml容量のオートクレ
ーブに仕込み、これにプロピレンを２０Kg／cm2 Ｇにな
るまで封入した後、１２０℃で２時間加熱攪拌した。The present invention will be described below with reference to examples.
The present invention is not limited to these examples. Example 1 1.5 g of 2-naphthol, 6 ml of n-hexane and ultra stable Y
Type zeolite (H-USY (TSZ33 manufactured by Tosoh Corporation)
0) A mixture of 0.30 g was charged into an autoclave having a volume of 50 ml, and propylene was charged therein to 20 kg / cm 2 G, and then heated and stirred at 120 ° C. for 2 hours.
【００１１】反応成績は、２−ナフトール転化率７２
％、モノイソプロピル−２−ナフトール選択率８４％、
そのうち、６−イソプロピル−２−ナフトール選択率８
１％であつた。 比較例１ 実施例１において、超安定Ｙ型ゼオライトに代えて、Ｈ
−ＺＳＭ５（バイエル社製）0.３０ｇを用いた以外は、
実施例１と同様に反応を行なつた。The reaction results are 2-naphthol conversion 72
%, Monoisopropyl-2-naphthol selectivity 84%,
Among them, 6-isopropyl-2-naphthol selectivity 8
It was 1%. Comparative Example 1 In Example 1, in place of the ultra stable Y-type zeolite, H
-ZSM5 (manufactured by Bayer) except that 0.30 g was used,
The reaction was carried out in the same manner as in Example 1.
【００１２】反応成績は、２−ナフトール転化率１２
％、モノイソプロピル−２−ナフトール選択率９２％、
そのうち、６−イソプロピル−２−ナフトール選択率４
３％であつた。 比較例２ 実施例１において、超安定Ｙ型ゼオライトに代えて、塩
化アルミニウム0.３０ｇを用いると共に、反応温度を４
０℃とした以外は、実施例１と同様に反応を行なつた。The reaction results are as follows: 2-naphthol conversion 12
%, Monoisopropyl-2-naphthol selectivity 92%,
Among them, 6-isopropyl-2-naphthol selectivity 4
It was 3%. Comparative Example 2 In Example 1, 0.30 g of aluminum chloride was used in place of the ultrastable Y-type zeolite, and the reaction temperature was 4
The reaction was performed in the same manner as in Example 1 except that the temperature was 0 ° C.
【００１３】反応成績は、２−ナフトール転化率６７
％、モノイソプロピル−２−ナフトール選択率４１％、
そのうち、６−イソプロピル−２−ナフトール選択率３
３％であつた。 比較例３ 実施例１において、超安定Ｙ型ゼオライトに代えて、モ
ルデナイト（ＴＳＺ−６２０）0.３０ｇを用いた以外
は、実施例１と同様に反応を行なつた。The reaction results are as follows: 2-naphthol conversion of 67
%, Monoisopropyl-2-naphthol selectivity 41%,
Among them, 6-isopropyl-2-naphthol selectivity 3
It was 3%. Comparative Example 3 The reaction was performed in the same manner as in Example 1 except that 0.30 g of mordenite (TSZ-620) was used in place of the ultra stable Y-type zeolite.
【００１４】反応成績は、２−ナフトール転化率２６
％、モノイソプロピル−２−ナフトール選択率８１％、
そのうち、６−イソプロピル−２−ナフトール選択率４
１％であつた。 実施例２ 実施例１において、２−ナフトールに代えて、２−メト
キシナフタレン1.５ｇを用いた以外は、実施例１と同様
に反応を行なつた。The reaction results are as follows: 2-naphthol conversion 26
%, Monoisopropyl-2-naphthol selectivity 81%,
Among them, 6-isopropyl-2-naphthol selectivity 4
It was 1%. Example 2 The reaction was performed in the same manner as in Example 1 except that 1.5 g of 2-methoxynaphthalene was used instead of 2-naphthol.
【００１５】反応成績は、２−メトキシナフタレン転化
率７５％、モノイソプロピル−２−メトキシナフタレン
選択率８１％、そのうち、６−イソプロピル−２−メト
キシナフタレン選択率８３％であつた。The reaction results were a conversion of 2-methoxynaphthalene of 75%, a selectivity of monoisopropyl-2-methoxynaphthalene of 81%, and a selectivity of 6-isopropyl-2-methoxynaphthalene of 83%.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location // C07B 61/00 300
Claims (1)
れる２位置換ナフタレンをＹ型ゼオライトの存在下にプ
ロピレンにてイソプロピル化することを特徴とする２位
置換６−イソプロピルナフタレンの製造方法。1. A compound represented by the general formula (I): (In the formula, R represents a hydrogen atom or a methyl group.) 2-position-substituted naphthalene is isopropylated with propylene in the presence of Y-type zeolite to produce 2-position-substituted 6-isopropylnaphthalene. Method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3251992A JPH0585978A (en) | 1991-09-30 | 1991-09-30 | Production of 2-substituted 6-isopropylnaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3251992A JPH0585978A (en) | 1991-09-30 | 1991-09-30 | Production of 2-substituted 6-isopropylnaphthalene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0585978A true JPH0585978A (en) | 1993-04-06 |
Family
ID=17231039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3251992A Pending JPH0585978A (en) | 1991-09-30 | 1991-09-30 | Production of 2-substituted 6-isopropylnaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0585978A (en) |
-
1991
- 1991-09-30 JP JP3251992A patent/JPH0585978A/en active Pending
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