JPH04202148A - Production of 3,5-di-t butyl-2,6-dichlorotoluene - Google Patents
Production of 3,5-di-t butyl-2,6-dichlorotolueneInfo
- Publication number
- JPH04202148A JPH04202148A JP2329648A JP32964890A JPH04202148A JP H04202148 A JPH04202148 A JP H04202148A JP 2329648 A JP2329648 A JP 2329648A JP 32964890 A JP32964890 A JP 32964890A JP H04202148 A JPH04202148 A JP H04202148A
- Authority
- JP
- Japan
- Prior art keywords
- lewis acid
- tert
- dichlorotoluene
- butyl
- butyltoluene
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- FDODNRONTOKBNF-UHFFFAOYSA-N 1,3-dichloro-2-pentylbenzene Chemical compound CCCCCC1=C(Cl)C=CC=C1Cl FDODNRONTOKBNF-UHFFFAOYSA-N 0.000 title 1
- 239000002841 Lewis acid Substances 0.000 claims abstract description 22
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 20
- WIXDSJRJFDWTNY-UHFFFAOYSA-N 1,3-ditert-butyl-5-methylbenzene Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 WIXDSJRJFDWTNY-UHFFFAOYSA-N 0.000 claims abstract description 14
- CXRPXFZFGODPFD-UHFFFAOYSA-N 1,5-ditert-butyl-2,4-dichloro-3-methylbenzene Chemical compound CC1=C(Cl)C(C(C)(C)C)=CC(C(C)(C)C)=C1Cl CXRPXFZFGODPFD-UHFFFAOYSA-N 0.000 claims abstract description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 10
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 abstract description 4
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000011593 sulfur Substances 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明は、３，５−ジ−第３ブチル−２，６−ジクロロ
トルエンの改良された製造方法に関する。The present invention relates to an improved method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene.
従来、農薬或いは医薬の合成中間体として有用な２，６
−ジクロロトルエンは、トルエンを原料として３，５−
ジ−第３ブチル−２，６−ジクロロトルエンを経由して
製造することが知られており、その中間体である、３，
５−ジ−第３ブチル−２，６−ジクロロトルエンは、ト
ルエンの第３ブチル化によって得られる３、５−ジ−第
３ブチルトルエンを塩素化することによって得られるも
のである。
３．５−ジ−第３ブチルトルエンの塩素化法としては、
例えば、特開昭６２−５９３０号公報に、スルフリルク
ロライドによって塩素化する方法と共に、ルイス酸及び
５２Ｃ１２、Ｆｅｓなどの硫黄化合物の存在下に、塩素
ガスによって塩素化する方法が開示されている。また、
特開平２−５３７４３号公報には、上記特開昭公報に記
載の技術の改良方法として、ルイス酸及び単体硫黄の存
在下、単体硫黄をルイス酸に対して５０〜１５０モル％
使用して、塩素ガスによって塩素化する方法が開示され
ている。
これら従来の方法においては、目的物以外の副生を抑制
するために反応温度が低いほど好ましいが、３．５−ジ
−第３ブチル−２，６−トルエンの融点が６８℃であり
、低温では反応中に結晶が・ 析出してくることから、
副反応を抑制し、かつ、結晶の析出を避けるため、極性
溶媒が使用されている。Conventionally, 2,6 which is useful as a synthetic intermediate for agricultural chemicals or medicines.
-Dichlorotoluene is made from 3,5-
It is known to be produced via di-tert-butyl-2,6-dichlorotoluene, and its intermediate, 3,
5-di-tert-butyl-2,6-dichlorotoluene is obtained by chlorinating 3,5-di-tert-butyltoluene obtained by tertiary-butylation of toluene. As a chlorination method for 3.5-di-tert-butyltoluene,
For example, JP-A-62-5930 discloses a method of chlorination with sulfuryl chloride and a method of chlorination with chlorine gas in the presence of a Lewis acid and a sulfur compound such as 52C12 or Fes. Also,
JP-A-2-53743 discloses a method for improving the technique described in JP-A-2-53743, in which in the presence of a Lewis acid and elemental sulfur, elemental sulfur is added in an amount of 50 to 150 mol % based on the Lewis acid.
A method of chlorination with chlorine gas is disclosed. In these conventional methods, the lower the reaction temperature is, the better in order to suppress by-products other than the target product, but the melting point of 3,5-di-tert-butyl-2,6-toluene is 68°C, and the low temperature Since crystals will precipitate during the reaction,
Polar solvents are used to suppress side reactions and avoid crystal precipitation.
しかしながら、上記従来の方法は、３．５−ジ−第３ブ
チル−２，６−ジクロロトルエンの収率が７０％前後で
あり、満足できるものではない。
上記したように、３．５−ジ−第３ブチル−２゜６−ジ
クロロトルエンは、２，６−ジクロロトルエンの製造中
間体として使用されるものであって、トルエンを出発原
料としてブチル化して得られる３、５−ジ−第３ブチル
トルエンを塩素化して得られ、このものはさらに脱ブチ
ル化されて２，６−ジクロロトルエンに導かれるが、３
．５−ジ−第３ブチルトルエンの塩素化収率の低さが、
２゜６−ジクロロトルエンの製造上のネックになってい
る。
本発明は、上記のような現状に鑑みてなされたものであ
って、その目的は、３．５−ジ−第３ブチルトルエンよ
り、３，５−ジ−第３ブチル−２゜６−ジクロロトルエ
ンを高収率で得ることができる方法を提供することにあ
る。However, the above conventional method has a yield of 3,5-di-tert-butyl-2,6-dichlorotoluene of around 70%, which is not satisfactory. As mentioned above, 3,5-di-tert-butyl-2゜6-dichlorotoluene is used as an intermediate in the production of 2,6-dichlorotoluene, and is produced by butylating toluene as a starting material. It is obtained by chlorinating the obtained 3,5-di-tert-butyltoluene, which is further debutylated to lead to 2,6-dichlorotoluene.
．． The low chlorination yield of 5-di-tert-butyltoluene is due to
This is a bottleneck in the production of 2゜6-dichlorotoluene. The present invention was made in view of the above-mentioned current situation, and its purpose is to produce 3,5-di-tert-butyl-2゜6-dichloro from 3,5-di-tert-butyltoluene. The object of the present invention is to provide a method capable of obtaining toluene in high yield.
本発明者等は、塩素ガスによる３、５−ジ−第３ブチル
トルエンの塩素化について、鋭意研究した結果、ルイス
酸及び単体硫黄を触媒とし、単体硫黄／ルイス酸のモル
比を８〜２５とするとき、３．５−ジ−第３ブチル−２
，６−ジクロロトルエンの収率が著しく向上することを
見いだし、本発明を完成するに至った。
すなわち、本発明の構成上の特徴は、３． ５−ジ−第
３ブチルトルエンをルイス酸及び単体硫黄の存在下、塩
素ガスによって塩素化することがらなる３、５−ジ−第
３ブチル−２，６−ジクロロトルエンの製造方法におい
て、単体硫黄／ルイス酸のモル比を８〜２５の範囲にお
いて塩素化を行うことにある。
以下、本発明について詳細に説明する。
本発明における原料物質である３、５−ジ−第３ブチル
トルエンは、公知の方法により製造される。例えば、ト
ルエンを第３ブチルクロリドと反応させて得られる第３
ブチルトルエンを、塩化アルミニウムの存在下、不均化
反応させることにより、容易に得ることができる。
本発明において、塩素化反応は、触媒としてルイス酸及
び単体硫黄を併用して行われる。ルイス酸としては、例
えば、Ａ Ｉ ＣＬ 、Ｆ ｅ Ｃｌ ３、５ｂＣＩ
５ｎＣ１４、およびＴ ｉＣ１ｉ、など３ ゝ
をあげることができる。ルイス酸の使用量は、原料物質
の３，５−ジ−第３ブチルトルエンに対して、０．０１
〜５モル％、好ましくは、０．０５〜５モル％の範囲に
設定される。本発明において、ルイス酸と単体硫黄の使
用割合は、単体硫黄／ルイス酸のモル比を８〜２５の範
囲にすることが必要であり、好ましくは１０〜２０の範
囲である。
単体硫黄のルイス酸に対するモル比が８未満の場合は、
反応収率が低く、一方、単体硫黄の量をそれ以上増やし
ても反応収率の向上は微増に止まるので、２５よりも多
く使用するのは経済的ではない。
本発明の実施に当たっては、反応温度は４５〜７０℃、
好ましくは５０〜６０℃に設定する。本発明では、多量
の単体硫黄を用いることから、３．５−ジ−第３ブチル
トルエンから第３ブチル基の脱離を抑制し得るため、従
来好ましいとされていた０〜３０℃より高温での反応が
可能で、しかも目的物を高い収率で得ることができる。
従来の方法に比べ高温で反応させ得ることから反応溶媒
を必要としない。しかし、反応温度が４５℃より低くな
ると、反応中に生成物が析出してくることが避けられず
、７０℃を超える温度で反応させると、副反応が急激に
増加することから、反応温度は上記のように設定される
。As a result of extensive research into the chlorination of 3,5-di-tert-butyltoluene with chlorine gas, the present inventors discovered that using Lewis acid and elemental sulfur as catalysts, the molar ratio of elemental sulfur/Lewis acid was 8 to 25. 3.5-di-tert-butyl-2
, 6-dichlorotoluene was found to be significantly improved, and the present invention was completed. That is, the structural features of the present invention are 3. A method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene, which comprises chlorinating 5-di-tert-butyltoluene with chlorine gas in the presence of a Lewis acid and elemental sulfur. The purpose is to carry out chlorination at a molar ratio of Lewis acid/Lewis acid in the range of 8 to 25. The present invention will be explained in detail below. 3,5-di-tert-butyltoluene, which is a raw material in the present invention, is produced by a known method. For example, tertiary butyl chloride obtained by reacting toluene with tertiary butyl chloride
Butyltoluene can be easily obtained by subjecting it to a disproportionation reaction in the presence of aluminum chloride. In the present invention, the chlorination reaction is carried out using a Lewis acid and elemental sulfur together as a catalyst. Examples of Lewis acids include AI CL , Fe Cl 3 , 5bCI
5nC14, and TiC1i, among others. The amount of Lewis acid used is 0.01 per 3,5-di-tert-butyltoluene as the raw material.
It is set in the range of 5 mol% to 5 mol%, preferably 0.05 to 5 mol%. In the present invention, the ratio of Lewis acid to elemental sulfur used is such that the molar ratio of elemental sulfur/Lewis acid is in the range of 8 to 25, preferably in the range of 10 to 20. If the molar ratio of elemental sulfur to Lewis acid is less than 8,
The reaction yield is low, and on the other hand, even if the amount of elemental sulfur is increased further, the reaction yield will only increase slightly, so it is not economical to use more than 25. In carrying out the present invention, the reaction temperature is 45 to 70°C,
Preferably it is set at 50 to 60°C. In the present invention, since a large amount of elemental sulfur is used, it is possible to suppress the elimination of the tert-butyl group from 3,5-di-tert-butyltoluene, so it is possible to suppress the elimination of the tertiary-butyl group from 3,5-di-tert-butyltoluene. reaction, and the desired product can be obtained in high yield. Since the reaction can be carried out at a higher temperature than conventional methods, no reaction solvent is required. However, if the reaction temperature is lower than 45°C, it is inevitable that the product will precipitate during the reaction, and if the reaction is carried out at a temperature higher than 70°C, side reactions will rapidly increase. Set as above.
以下、本発明を実施例及び比較例によって説明する。
実施例１
攪拌装置、還流冷却器、温度計を備えた３００リツトル
の反応器に、３．５−ジ−第３ブチルトルエン１５０ｋ
ｇ（７４０モル）、無水塩化鉄労（ＩＩ＋） ０．
１２ｋｇ （０，７４モル）、単体硫黄０．２４ｋｇ
（７，４モル）を仕込み、攪拌しながら６０℃で塩素ガ
スを１４７モル／時間の導入速度で吹き込み、１０時間
反応させた。発生する塩化水素ガスは、水酸化ナトリウ
ム水溶液に導いた。次いで、反応混合物を水洗し、得ら
れた反応液をガスクロマトグラフィーにより組成分析し
た。
その結果、３，５−ジ−第３ブチル−２，６−ジクロロ
トルエンの収率は８３％であることが確認された。
実施例２
攪拌装置、還流冷却器、温度計を備えた６００リツトル
の反応器に、３．５−ジ−第３ブチルトルエン２９０ｋ
ｇ （１，４２キロモル）、無水塩化アルミニウム（Ｉ
Ｉ＋）０． １９ｋｇ （１，４２モル）、単体硫黄０
．９１ｋｇ （２８，４モル）を仕込み、攪拌しながら
５０°Ｃで塩素ガスを２３７モル／時間の導入速度で吹
き込み、１２時間反応させた。発生する塩化水素ガスは
、水酸化ナトリウム水溶液に導いた。次いで、反応混合
物を水洗し、得られた反応液をガスクロマトグラフィー
により組成分析した。その結果、３，５−ジ−第３ブチ
ル−２，６−ジクロロトルエンの収率は８５゜１％であ
ることが確認された。
比較例１〜４
実施例２における無水塩化アルミニウム（ＩＩ＋）及び
単体硫黄の使用量を表１に示す割合に変えて、実施例２
と同様に反応させ、得られた反応液をガスクロマトグラ
フィーにより組成分析した。３゜５−ジ−第３ブチル−
２，６−ジクロロトルエンの収率を表１に示す。
表１The present invention will be explained below with reference to Examples and Comparative Examples. Example 1 150 k of 3,5-di-tert-butyltoluene was added to a 300 liter reactor equipped with a stirrer, reflux condenser and thermometer.
g (740 mol), anhydrous iron chloride (II+) 0.
12 kg (0.74 mol), elemental sulfur 0.24 kg
(7.4 mol) was charged, and while stirring, chlorine gas was blown in at an introduction rate of 147 mol/hour at 60°C, and the reaction was allowed to proceed for 10 hours. The generated hydrogen chloride gas was led to an aqueous sodium hydroxide solution. Next, the reaction mixture was washed with water, and the composition of the resulting reaction solution was analyzed by gas chromatography. As a result, it was confirmed that the yield of 3,5-di-tert-butyl-2,6-dichlorotoluene was 83%. Example 2 In a 600 liter reactor equipped with a stirrer, reflux condenser and thermometer, 290 k of 3,5-di-tert-butyltoluene was added.
g (1,42 kmol), anhydrous aluminum chloride (I
I+)0. 19kg (1.42 mol), elemental sulfur 0
．． 91 kg (28.4 mol) was charged, and while stirring, chlorine gas was blown in at a rate of 237 mol/hour at 50°C, and the reaction was allowed to proceed for 12 hours. The generated hydrogen chloride gas was led to an aqueous sodium hydroxide solution. Next, the reaction mixture was washed with water, and the composition of the resulting reaction solution was analyzed by gas chromatography. As a result, it was confirmed that the yield of 3,5-di-tert-butyl-2,6-dichlorotoluene was 85.1%. Comparative Examples 1 to 4 Example 2 was prepared by changing the amounts of anhydrous aluminum chloride (II+) and elemental sulfur in Example 2 to the proportions shown in Table 1.
The reaction solution was reacted in the same manner as above, and the composition of the resulting reaction solution was analyzed by gas chromatography. 3゜5-di-tert-butyl-
Table 1 shows the yield of 2,6-dichlorotoluene. Table 1
本発明は、従来、極性溶剤の存在下で行われて □い
た塩素ガスによる３、５−ジ−第３ブチルトルエンの塩
素化反応を、単体硫黄とスイス酸を上記のモル比で使用
することにより、３，５−ジ−第３ブチル−２，６−ジ
クロロトルエンを８０％以上の高収率で製造することが
可能になる。しかも、ルイス酸の使用量は、従来知られ
ている方法に比して著しく少なくてよく、また溶媒を使
用しなくてもよいため、その製造は工業的に極めて有利
に実施することができる。The present invention improves the chlorination reaction of 3,5-di-tert-butyltoluene with chlorine gas, which has conventionally been carried out in the presence of a polar solvent, by using elemental sulfur and Swiss acid in the above molar ratio. This makes it possible to produce 3,5-di-tert-butyl-2,6-dichlorotoluene with a high yield of 80% or more. In addition, the amount of Lewis acid used can be significantly smaller than in conventionally known methods, and since no solvent is required, the production can be carried out industrially with great advantage.
Claims (2)
単体硫黄の存在下、塩素ガスによって塩素化することか
らなる３，５−ジ−第３ブチル−２，６−ジクロロトル
エンの製造方法において、単体硫黄／ルイス酸のモル比
を８〜２５の範囲において塩素化を行うことを特徴とす
る３，５−ジ−第３ブチル−２，６−ジクロロトルエン
の製造方法。(1) Production of 3,5-di-tert-butyl-2,6-dichlorotoluene by chlorinating 3,5-di-tert-butyltoluene with chlorine gas in the presence of a Lewis acid and elemental sulfur. A method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene, characterized in that chlorination is carried out at a molar ratio of elemental sulfur/Lewis acid in the range of 8 to 25.
（１）に記載の３，５−ジ−第３ブチル−２，６−ジク
ロロトルエンの製造方法。(2) The method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene according to claim (1), wherein the chlorination is carried out without a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2329648A JP2815698B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2329648A JP2815698B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04202148A true JPH04202148A (en) | 1992-07-22 |
| JP2815698B2 JP2815698B2 (en) | 1998-10-27 |
Family
ID=18223694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2329648A Expired - Fee Related JP2815698B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2815698B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6271426B1 (en) | 1995-06-13 | 2001-08-07 | Kureha Kagaku Kogyo K.K. | Process for the production of 2,6-dichloro-3,5-di(secondary or tertiary alkyl)toluene |
-
1990
- 1990-11-30 JP JP2329648A patent/JP2815698B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6271426B1 (en) | 1995-06-13 | 2001-08-07 | Kureha Kagaku Kogyo K.K. | Process for the production of 2,6-dichloro-3,5-di(secondary or tertiary alkyl)toluene |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2815698B2 (en) | 1998-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH04202148A (en) | Production of 3,5-di-t butyl-2,6-dichlorotoluene | |
| JPH02196747A (en) | Production of tetrabromobisphenol a | |
| JP3620221B2 (en) | Method for producing homocystin | |
| EP0070467B1 (en) | Process for synthesising n-isopropyl-n'-o-carbomethoxyphenylsulphamide | |
| JPS59106438A (en) | Manufacture of 1,3-diacetoxy-2-methylenepropane | |
| JPS58208265A (en) | Preparation of chloroalkylphenylsulfones | |
| US3989715A (en) | Process for manufacturing chlorothianthrenes | |
| EP0151835B1 (en) | Process for producing pentachloronitrobenzene from hexachlorobenzene | |
| US4388251A (en) | Method for preparing 2-chlorobenzoyl chloride | |
| JP2001058968A (en) | Production of 1,3-di(2-parahydroxyphenyl-2-propyl)benzene | |
| JPS5948818B2 (en) | Production method of α-chloroethyl ethyl carbonate | |
| JPS62263142A (en) | Manufacture of high purity 5-chloroisophthaloyl chloride | |
| JP3214923B2 (en) | Method for producing tertiary hydroperoxide | |
| JPS621382B2 (en) | ||
| JP3148484B2 (en) | Method for producing 1-amino-5-benzoylaminoanthraquinone | |
| JPS6256848B2 (en) | ||
| JPS62185082A (en) | Production of tetrachlorophthalic anhydride | |
| JPS59227844A (en) | Production of aminomalonamide | |
| JPS6317060B2 (en) | ||
| JPH09157238A (en) | Production of t-butylhyrazine hydrogen halide salt | |
| JPH05320126A (en) | Production of 2-amino-5-nitrothiobenzamide | |
| JPH0623146B2 (en) | Process for producing N, N-diethylanilines | |
| JPH10139699A (en) | Production of 4,4'-bischloromethylbiphenyl | |
| JPH08208586A (en) | Production of 4'-cyanobiphenyl-4-ol | |
| JPS6028976A (en) | Production of quaternary salt of piperidylidenemethane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |