JP4371416B2 - High purity 2,4-dichloro-3-alkyl-6-tert-butylphenol and process for producing the same - Google Patents
High purity 2,4-dichloro-3-alkyl-6-tert-butylphenol and process for producing the same Download PDFInfo
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- JP4371416B2 JP4371416B2 JP2004089386A JP2004089386A JP4371416B2 JP 4371416 B2 JP4371416 B2 JP 4371416B2 JP 2004089386 A JP2004089386 A JP 2004089386A JP 2004089386 A JP2004089386 A JP 2004089386A JP 4371416 B2 JP4371416 B2 JP 4371416B2
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- 238000000034 method Methods 0.000 title description 9
- 238000006243 chemical reaction Methods 0.000 claims description 53
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 25
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 9
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 8
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000003905 agrochemical Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QTAATZDGGZYBDC-UHFFFAOYSA-N 2,4,6-trichloro-3-methylphenol Chemical compound CC1=C(Cl)C=C(Cl)C(O)=C1Cl QTAATZDGGZYBDC-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- MXNRALZQWPSLPB-UHFFFAOYSA-N 6-tert-butyl-2,4-dichloro-3-methylphenol Chemical compound CC1=C(Cl)C=C(C(C)(C)C)C(O)=C1Cl MXNRALZQWPSLPB-UHFFFAOYSA-N 0.000 description 1
- QGAHQHUSBPWRMV-UHFFFAOYSA-N 6-tert-butyl-2-chloro-3-methylphenol Chemical compound C(C)(C)(C)C=1C=CC(=C(C=1O)Cl)C QGAHQHUSBPWRMV-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は、写真薬、医薬、農薬用原料中間体として有用な２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類の製造方法に関し、詳しくは、過酸化水素存在下に３−アルキル−６−ｔｅｒｔ−ブチルフェノール類と塩化水素を反応させることを特徴とする２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類の製造方法に関するものである。 The present invention relates to a process for producing 2,4-dichloro-3-alkyl-6-tert-butylphenols useful as a raw material intermediate for photographic drugs, pharmaceuticals, and agricultural chemicals, and more specifically, 3-alkyl in the presence of hydrogen peroxide. The present invention relates to a process for producing 2,4-dichloro-3-alkyl-6-tert-butylphenol, which comprises reacting -6-tert-butylphenol with hydrogen chloride.
２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類は、６位のｔｅｒｔ−ブチル基を脱ｔｅｒｔ−ブチル化することにより、写真薬、医薬、農薬用原料中間体として有用な２，４−ジクロロ−３−アルキルフェノール類を容易に得られるため非常に有用な化合物である。 2,4-Dichloro-3-alkyl-6-tert-butylphenol is useful as a raw material intermediate for photographic drugs, pharmaceuticals, and agricultural chemicals by detert-butylation of the 6-position tert-butyl group. Since 4-dichloro-3-alkylphenols can be easily obtained, it is a very useful compound.
２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類を製造する公知の方法としては、３−アルキル−６−ｔｅｒｔ−ブチルフェノール類と塩素ガスとを反応させる方法（特許文献１、２）が公知である。しかし、これらの方法では、塩素化に際して塩素ガスを用いるため、式（３）で示されるトリクロロ体の副生を抑制することが困難であり、写真薬、医薬、農薬用原料中間体として用いるのに適した高純度品を得ることは困難であった。 また塩素ガスを用いる製造方法は、塩素ガスの性質上、特殊な安全設備を必要とするため、工業的規模での実施には不利である。
式（３）
Formula (3)
本発明は写真薬、医薬、農薬用原料中間体として有用な、トリクロロ体の低減された２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類を塩素ガスを用いることなく、高純度で、かつ工業的に有利に製造する方法を提供するものである。 The present invention provides 2,4-dichloro-3-alkyl-6-tert-butylphenols having a reduced trichloro form, which is useful as a raw material intermediate for photographic drugs, pharmaceuticals, and agricultural chemicals, with high purity without using chlorine gas. And an industrially advantageous production method.
本発明者らは、上記課題を解決するため、３−アルキル−６−ｔｅｒｔ−ブチルフェノール類から塩素ガスを用いることなく、トリクロロ体の低減された高純度の２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類を工業的に有利に製造する方法につき、鋭意検討した結果、
式（１）
（Ｒ１は、炭素数１〜４のアルキル基を表わす）で示される３−アルキル−６−ｔｅｒｔ−ブチルフェノール類と塩化水素を過酸化水素存在下、特定の反応条件のもとに反応することによりトリクロロ体（前記式（３））が０．５ｗｔ％以下に低減された
式（２）
Formula (1)
(R1 represents an alkyl group having 1 to 4 carbon atoms) by reacting 3-alkyl-6-tert-butylphenol with hydrogen chloride in the presence of hydrogen peroxide under specific reaction conditions. Formula (2) in which the trichloro form (formula (3)) is reduced to 0.5 wt% or less
以下、本発明について更に詳細に説明する。
本発明において、式（１）
In the present invention, the formula (1)
本発明における反応は通常、反応開始時には塩酸および過酸化水素水溶液が用いられるため、水層と油層（３−アルキル−６−ｔｅｒｔ−ブチルフェノール類含有層）との２層系での反応となる。 Since the reaction in the present invention usually uses hydrochloric acid and an aqueous hydrogen peroxide solution at the start of the reaction, the reaction is a two-layer reaction of an aqueous layer and an oil layer (3-alkyl-6-tert-butylphenols-containing layer).
本発明における過酸化水素の使用量は、式（1）で示される３−アルキル−６−ｔｅｒｔ−ブチルフェノール類１モルに対し、通常、過酸化水素２モル以上であり、好ましくは、２．２〜４．０モルである。 The amount of hydrogen peroxide used in the present invention is usually 2 mol or more of hydrogen peroxide per mol of 3-alkyl-6-tert-butylphenol represented by the formula (1), preferably 2.2. -4.0 moles.
本発明において反応開始時の反応系における水層中の過酸化水素濃度は、２０ｗｔ％以下であり、かつ、反応終了時の反応系における水層中の過酸化水素濃度は、４ｗｔ％以上であり、好ましくは１０ｗｔ％〜２０ｗｔ％である。水層中の過酸化水素濃度が２０ｗｔ％より高い場合は、式（３）で示されるトリクロロ体が増加する傾向があり、反応終了時の水層中の過酸化水素濃度が４ｗｔ％より低い場合は、反応率が低下する傾向がある。 In the present invention, the hydrogen peroxide concentration in the aqueous layer in the reaction system at the start of the reaction is 20 wt% or less, and the hydrogen peroxide concentration in the aqueous layer in the reaction system at the end of the reaction is 4 wt% or more. It is preferably 10 wt% to 20 wt%. When the hydrogen peroxide concentration in the aqueous layer is higher than 20 wt%, the trichloro form represented by the formula (3) tends to increase, and when the hydrogen peroxide concentration in the aqueous layer at the end of the reaction is lower than 4 wt% Tends to decrease the reaction rate.
本発明において反応開始時の反応系における水層中の過酸化水素濃度が、２０ｗｔ％以下であり、かつ、反応終了時の反応系における水層中の過酸化水素濃度が、４ｗｔ％以上でおこなう方法としては、例えば、反応途中で一旦反応を中断して水層を分離し、過酸化水素水溶液を再添加して反応する方法等が挙げられる。 In the present invention, the hydrogen peroxide concentration in the aqueous layer in the reaction system at the start of the reaction is 20 wt% or less, and the hydrogen peroxide concentration in the aqueous layer in the reaction system at the end of the reaction is 4 wt% or more. Examples of the method include a method in which the reaction is temporarily interrupted during the reaction, the aqueous layer is separated, and a hydrogen peroxide aqueous solution is added again to react.
本発明に使用される過酸化水素水溶液の濃度について、特に制限はなく、７０ｗｔ％の濃度のものも使用できるが、通常は、４ｗｔ％〜２０ｗｔ％の過酸化水素水溶液が用いられる。 There is no restriction | limiting in particular about the density | concentration of the hydrogen peroxide solution used for this invention, Although the thing of a 70 wt% density | concentration can be used, Usually, 4 wt%-20 wt% hydrogen peroxide aqueous solution is used.
本発明における塩化水素の使用量は、式（1）で示される３−アルキル−６−ｔｅｒｔ−ブチルフェノール類１モルに対し、通常、塩化水素２モル以上であり、好ましくは、２．２〜６．０モルであり、さらに好ましくは、３．０〜４．０モルである。 The amount of hydrogen chloride used in the present invention is usually 2 mol or more of hydrogen chloride with respect to 1 mol of 3-alkyl-6-tert-butylphenol represented by the formula (1), preferably 2.2 to 6 The amount is 0.0 mol, and more preferably 3.0 to 4.0 mol.
本発明において使用される塩化水素の形態は、塩酸であっても、塩化水素ガスを反応系に添加する方法であってもよい。 The form of hydrogen chloride used in the present invention may be hydrochloric acid or a method of adding hydrogen chloride gas to the reaction system.
本発明において反応開始時の反応系における水層中の塩化水素濃度は、３０ｗｔ％以下であり、かつ、反応終了時の反応系における水層中の塩化水素濃度が、５ｗｔ％以上であり、好ましくは、１０ｗｔ％〜２５ｗｔ％である。 反応開始時の水層中の塩化水素濃度が３０ｗｔ％より高い場合は、式（３）で示されるトリクロロ体が増加する傾向があり、反応終了時の水層中の塩化水素濃度が５ｗｔ％より低い場合は、反応率が低下する傾向がある。 In the present invention, the hydrogen chloride concentration in the aqueous layer in the reaction system at the start of the reaction is 30 wt% or less, and the hydrogen chloride concentration in the aqueous layer in the reaction system at the end of the reaction is 5 wt% or more, preferably Is 10 wt% to 25 wt%. When the hydrogen chloride concentration in the aqueous layer at the start of the reaction is higher than 30 wt%, the trichloro form represented by the formula (3) tends to increase, and the hydrogen chloride concentration in the aqueous layer at the end of the reaction is more than 5 wt%. When it is low, the reaction rate tends to decrease.
本発明において反応開始時の反応系における水層中の塩化水素濃度が、３０ｗｔ％以下であり、かつ、反応終了時の反応系における水層中の塩化水素濃度が、５ｗｔ％以上でおこなう方法としては、例えば、反応開始後、塩化水素の濃度低下分を補う目的で反応系に塩化水素ガスを添加する方法、あるいは反応途中で一旦反応を中断して水層を分離し、塩酸を再添加して反応する方法等が挙げられる。 In the present invention, the hydrogen chloride concentration in the aqueous layer in the reaction system at the start of the reaction is 30 wt% or less, and the hydrogen chloride concentration in the aqueous layer in the reaction system at the end of the reaction is 5 wt% or more. For example, after the start of the reaction, hydrogen chloride gas is added to the reaction system for the purpose of compensating for the decrease in hydrogen chloride concentration, or the reaction is temporarily stopped during the reaction, the aqueous layer is separated, and hydrochloric acid is added again. And the like.
本発明における反応温度は、通常、０℃から８０℃の範囲であり、好ましくは、３０〜８０℃である。 The reaction temperature in the present invention is usually in the range of 0 to 80 ° C, preferably 30 to 80 ° C.
本発明の塩素化反応は、高純度の目的物が得られることに加えて、塩素ガスを使用せず、
副生ガスの発生もない２層系での反応であるため、特殊な安全設備を必要とせず、目的物の単離が容易であるため、特に工業的にすぐれた製造方法である。
The chlorination reaction of the present invention, in addition to obtaining a high-purity target product, does not use chlorine gas,
Since it is a reaction in a two-layer system with no by-product gas generation, it does not require special safety equipment, and it is easy to isolate the target product.
本発明の方法によれば、写真薬、医薬、農薬用原料中間体として有用な、トリクロロ体の低減された２，４−ジクロロ−３−アルキル−６−ｔｅｒｔ−ブチルフェノール類を塩素ガスを用いることなく、安全に高純度、高収率で工業的に有利に製造することができる。 According to the method of the present invention, 2,4-dichloro-3-alkyl-6-tert-butylphenol reduced in trichloro form, which is useful as a raw material intermediate for photographic drugs, pharmaceuticals, and agricultural chemicals, is used with chlorine gas. Therefore, it can be produced advantageously industrially with high purity and high yield safely.
次に、本発明の詳細を以下の実施例にて示すが、本発明はこれらに限定されるものではない。 Next, although the detail of this invention is shown in the following examples, this invention is not limited to these.
３−メチル−６−ｔｅｒｔ−ブチルフェノール１６４．３ｇ（１ｍｏｌ）と２０ｗｔ％過酸化水素水溶液５１０ｇ（３ｍｏｌ）を１ｌフラスコに仕込み、液温を２５〜３０℃に保ちながら攪拌下、導入管より塩化水素ガス１０４ｇ（２．８５ｍｏｌ）を３時間かけて吹き込む。次に昇温し、５０℃〜５５℃で５時間保温した後に水層と油層を分離し、油層を脱水することにより純度９７．８ｗｔ％の２，４−ジクロロ−３−メチル−６−ｔｅｒｔ−ブチルフェノール２３１．０ｇ（２，４，６−トリクロロ−３−メチルフェノール：０．４ｗｔ％）を得た。 本実施例における反応開始時の水層中の塩化水素濃度は０ｗｔ％、過酸化水素濃度は２０ｗｔ％であり、反応終了時の反応系における水層中の塩化水素濃度は６ｗｔ％であり、過酸化水素濃度は６ｗｔ％であった。 Charge 164.3 g (1 mol) of 3-methyl-6-tert-butylphenol and 510 g (3 mol) of a 20 wt% hydrogen peroxide aqueous solution to a 1 l flask, and maintain the liquid temperature at 25-30 ° C. while stirring, hydrogen chloride from the introduction tube. Gas 104 g (2.85 mol) is blown in over 3 hours. Next, the temperature was raised and the temperature was kept at 50 ° C. to 55 ° C. for 5 hours. The aqueous layer and the oil layer were separated, and the oil layer was dehydrated, thereby purifying 97.8 wt% of 2,4-dichloro-3-methyl-6-tert. -231.0 g (2,4,6-trichloro-3-methylphenol: 0.4 wt%) of butylphenol was obtained. In this example, the hydrogen chloride concentration in the aqueous layer at the start of the reaction was 0 wt% and the hydrogen peroxide concentration was 20 wt%. The hydrogen chloride concentration in the aqueous layer in the reaction system at the end of the reaction was 6 wt%. The hydrogen oxide concentration was 6 wt%.
３−メチル−６−ｔｅｒｔ−ブチルフェノール１６４．３ｇ（１ｍｏｌ）と３０ｗｔ％塩酸２４４ｇ（２ｍｏｌ）を１ｌフラスコに仕込み、液温を２５〜３０℃に保ちながら攪拌下、３５ｗｔ％過酸化水素水溶液１９４．３ｇ（２ｍｏｌ）を３時間かけて滴下する。次に昇温し、５０℃〜５５℃で５時間保温した後に水層と油層を分離し、油層と３０ｗｔ％塩酸１２２ｇ（１ｍｏｌ）をフラスコに仕込み、液温を２５〜３０℃に保ちながら攪拌下、３５ｗｔ％過酸化水素水溶液９７．２ｇ（１ｍｏｌ）を３時間かけて滴下する。次に昇温し、５０℃〜５５℃で５時間保温した後に水層と油層を分離し、油層を脱水することにより純度９８．０ｗｔ％の２，４−ジクロロ−３−メチル−６−ｔｅｒｔ−ブチルフェノール２３０．５ｇ（２，４，６−トリクロロ−３−メチルフェノール：０．３ｗｔ％）を得た。 本実施例における反応開始時の水層中の塩化水素濃度は３０ｗｔ％、過酸化水素濃度は０ｗｔ％であり、反応終了時の反応系における水層中の塩化水素濃度は６ｗｔ％であり、過酸化水素濃度は４ｗｔ％であった。 164.3 g (1 mol) of 3-methyl-6-tert-butylphenol and 244 g (2 mol) of 30 wt% hydrochloric acid were charged into a 1 l flask, and a 35 wt% aqueous hydrogen peroxide solution 194. was stirred while maintaining the liquid temperature at 25 to 30 ° C. 3 g (2 mol) is added dropwise over 3 hours. Next, the temperature was raised and kept at 50 ° C. to 55 ° C. for 5 hours, and then the aqueous layer and the oil layer were separated. The oil layer and 122 g (1 mol) of 30 wt% hydrochloric acid were charged into the flask and stirred while keeping the liquid temperature at 25 to 30 ° C. Then, 97.2 g (1 mol) of 35 wt% aqueous hydrogen peroxide solution is added dropwise over 3 hours. Next, the temperature was raised and the temperature was maintained at 50 ° C. to 55 ° C. for 5 hours, and then the aqueous layer and the oil layer were separated, and the oil layer was dehydrated to obtain 2,4-dichloro-3-methyl-6-tert having a purity of 98.0 wt%. -230.5 g (2,4,6-trichloro-3-methylphenol: 0.3 wt%) of butylphenol was obtained. In this example, the hydrogen chloride concentration in the aqueous layer at the start of the reaction was 30 wt%, the hydrogen peroxide concentration was 0 wt%, and the hydrogen chloride concentration in the aqueous layer in the reaction system at the end of the reaction was 6 wt%. The hydrogen oxide concentration was 4 wt%.
（比較例１）
３−メチル−６−ｔｅｒｔ−ブチルフェノール１６４．３ｇ（１ｍｏｌ）を１ｌフラスコに仕込み、液温を２５〜３０℃に保ちながら攪拌下、導入管より塩素ガス１４９ｇ（２．１０ｍｏｌ）を８時間かけて吹き込む。反応後、窒素ガスを通して液中に溶存する塩化水素を除去し、純度９２．３ｗｔ％の２，４−ジクロロ−３−メチル−６−ｔｅｒｔ−ブチルフェノール２２８．５ｇ（２，４，６−トリクロロ−３−メチルフェノール３．６ｗｔ％）を得た。
(Comparative Example 1)
Charge 164.3 g (1 mol) of 3-methyl-6-tert-butylphenol to a 1 l flask, and stir while maintaining the liquid temperature at 25-30 ° C., 149 g (2.10 mol) of chlorine gas from the introduction tube over 8 hours. Infuse. After the reaction, hydrogen chloride dissolved in the liquid was removed through nitrogen gas, and 228.5 g of 2,4-dichloro-3-methyl-6-tert-butylphenol having a purity of 92.3 wt% (2,4,6-trichloro- 3-methylphenol 3.6 wt%) was obtained.
（比較例２）
３−メチル−６−ｔｅｒｔ−ブチルフェノール１６４．３ｇ（１ｍｏｌ）と３５ｗｔ％塩酸４１８ｇ（４ｍｏｌ）を１ｌフラスコに仕込み、液温を２５〜３０℃に保ちながら攪拌下、３５ｗｔ％過酸化水素水溶液３１０．９ｇ（２ｍｏｌ）を３時間かけて滴下する。次に昇温し、５０℃〜５５℃で５時間保温した後に水層と油層を分離し、油層を脱水することにより純度８１．０ｗｔ％の２，４−ジクロロ−３−メチル−６−ｔｅｒｔ−ブチルフェノール２２６．０ｇ（２，４，６−トリクロロ−３−メチルフェノール：１．６ｗｔ％、２−クロロ−３−メチル−６−ｔｅｒｔ−ブチルフェノール：１７．１ｗｔ％）を得た。 本比較例における反応開始時の水層中の塩化水素濃度は３５ｗｔ％、過酸化水素濃度は０ｗｔ％であり、反応終了時の反応系における水層中の塩化水素濃度は６ｗｔ％であり、過酸化水素濃度は２ｗｔ％であった。
(Comparative Example 2)
Into a 1 l flask was charged 164.3 g (1 mol) of 3-methyl-6-tert-butylphenol and 418 g (4 mol) of 35 wt% hydrochloric acid, and the 35 wt% aqueous hydrogen peroxide solution 310. 9 g (2 mol) is added dropwise over 3 hours. Next, the temperature was raised and the temperature was maintained at 50 ° C. to 55 ° C. for 5 hours, and then the water layer and the oil layer were separated. There was obtained 226.0 g of butylphenol (2,4,6-trichloro-3-methylphenol: 1.6 wt%, 2-chloro-3-methyl-6-tert-butylphenol: 17.1 wt%). In this comparative example, the hydrogen chloride concentration in the aqueous layer at the start of the reaction was 35 wt%, the hydrogen peroxide concentration was 0 wt%, and the hydrogen chloride concentration in the aqueous layer in the reaction system at the end of the reaction was 6 wt%. The hydrogen oxide concentration was 2 wt%.
Claims (2)
（Ｒ１は、炭素数１〜４のアルキル基を表わす）で示される３−アルキル−６−ｔｅｒｔ−ブチルフェノール類と塩化水素を、過酸化水素存在下に反応する際の反応開始時の反応系における水層中の過酸化水素濃度が、２０ｗｔ％以下であり、かつ、反応終了時の反応系における水層中の過酸化水素濃度が、４ｗｔ％以上であることを特徴とする式（２）
(R1 represents an alkyl group having 1 to 4 carbon atoms) In the reaction system at the start of the reaction when reacting 3-alkyl-6-tert-butylphenol and hydrogen chloride in the presence of hydrogen peroxide. Formula (2), wherein the hydrogen peroxide concentration in the aqueous layer is 20 wt% or less, and the hydrogen peroxide concentration in the aqueous layer in the reaction system at the end of the reaction is 4 wt% or more.
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