JPS6334130B2 - - Google Patents
Info
- Publication number
- JPS6334130B2 JPS6334130B2 JP58082282A JP8228283A JPS6334130B2 JP S6334130 B2 JPS6334130 B2 JP S6334130B2 JP 58082282 A JP58082282 A JP 58082282A JP 8228283 A JP8228283 A JP 8228283A JP S6334130 B2 JPS6334130 B2 JP S6334130B2
- Authority
- JP
- Japan
- Prior art keywords
- toluene
- reaction
- catalyst
- dichlorotoluene
- dihalogenated
- 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.)
- Expired
Links
- 150000003613 toluenes Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910021536 Zeolite Inorganic materials 0.000 claims description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 12
- 239000010457 zeolite Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 description 13
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 7
- KFAKZJUYBOYVKA-UHFFFAOYSA-N 1,4-dichloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Cl KFAKZJUYBOYVKA-UHFFFAOYSA-N 0.000 description 6
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- GWLKCPXYBLCEKC-UHFFFAOYSA-N 1,2-dichloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1Cl GWLKCPXYBLCEKC-UHFFFAOYSA-N 0.000 description 2
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 description 2
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 2
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NHYCGSASNAIGLD-UHFFFAOYSA-N Chlorine monoxide Chemical compound Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- WCUPMUYJNRBENK-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(trichloromethyl)benzene Chemical compound ClC1=C(Cl)C(Cl)=C(C(Cl)(Cl)Cl)C(Cl)=C1Cl WCUPMUYJNRBENK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- Physical Or Chemical Processes And Apparatus (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、２，５−ジハロゲン化トルエンの製
造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2,5-dihalogenated toluene.
ジハロゲン化トルエン類は、医薬、農薬をはじ
め各種有機合成化学の原料として有用であり、特
に２，５−ジハロゲン化トルエン、例えば２，５
−ジクロロトルエンの需要が多い。 Dihalogenated toluenes are useful as raw materials for various organic synthetic chemicals including medicines and agricultural chemicals, and in particular, 2,5-dihalogenated toluenes, such as 2,5
-Dichlorotoluene is in high demand.
従来、触媒の存在下２−ハロゲン化トルエンを
ハロゲン化し２，５−ジクロロトルエンを製造す
る方法としては、共触媒として硫黄化合物が加え
られているような金属触媒の存在下１モルの２−
クロロトルエン当り0.5〜0.9グラム原子の塩素を
反応させる方法が知られている（米国特許第
4031146号明細書）。 Conventionally, as a method for producing 2,5-dichlorotoluene by halogenating 2-halogenated toluene in the presence of a catalyst, 1 mole of 2-dichlorotoluene is produced in the presence of a metal catalyst to which a sulfur compound is added as a cocatalyst.
It is known to react 0.5 to 0.9 gram atoms of chlorine per chlorotoluene (U.S. Pat.
4031146 specification).
しかしながら、この方法は副生するトリクロロ
トルエンの生成を６％以下に抑えるために２−ク
ロロトルエンの反応率を50〜70％に抑えなければ
ならず、その結果として２，５−ジクロロトルエ
ンの収率が30〜42％と低いという欠点があつた。 However, in this method, the reaction rate of 2-chlorotoluene must be suppressed to 50-70% in order to suppress the production of trichlorotoluene as a by-product to 6% or less, and as a result, the yield of 2,5-dichlorotoluene is The disadvantage was that the rate was low at 30-42%.
さらに、また触媒として硫黄及び／または硫黄
化合物の存在下２−クロロトルエン１モル当り
0.9〜1.1モルの塩素を反応させる方法が知られて
いる（特開昭51−143627号公報）。しかしながら、
この方法は２−クロロトルエンの収率が50％と向
上するが、前記の方法に比べ副生物のトリクロロ
トルエンの生成が８％に増えるという欠点があつ
た。 Additionally, also in the presence of sulfur and/or sulfur compounds as a catalyst per mole of 2-chlorotoluene.
A method of reacting with 0.9 to 1.1 moles of chlorine is known (Japanese Patent Application Laid-open No. 143627/1983). however,
Although this method improves the yield of 2-chlorotoluene to 50%, it has the disadvantage that the production of by-product trichlorotoluene increases to 8% compared to the above method.
さらにまた、ヨウ素を触媒として２−クロロト
ルエン１モル当り1.0〜1.6モルの塩素を反応させ
る方法が知られている（特開昭57−91934号公
報）。この方法は２，５−ジクロロトルエンが53
％と高収率で得られているが、副生物のトリクロ
ロトルエンが14〜22％と増加するという欠点があ
る。 Furthermore, a method is known in which 1.0 to 1.6 mol of chlorine is reacted with 1 mol of 2-chlorotoluene using iodine as a catalyst (Japanese Patent Application Laid-Open No. 57-91934). This method uses 53
%, but the drawback is that the by-product trichlorotoluene increases to 14-22%.
このように、いづれの方法においても高選択
率、高収率で２，５−ジクロロトルエンを製造す
るには未だ充分なものではなかつた。 As described above, none of the methods was sufficient to produce 2,5-dichlorotoluene with high selectivity and high yield.
本発明者らは、このような現状に鑑み、鋭意研
究を重ねた結果、意外にも触媒としてＬ型ゼオラ
イトを使用し、液相中で反応を行うことにより、
従来の問題点が解決できるばかりでなく従来の方
法に比べ優れた選択率で２，５−ジハロゲン化ト
ルエンが製造できることを見出しこの知見に基づ
いて本発明を完成するに至つた。 In view of the current situation, the present inventors have conducted extensive research and have unexpectedly found that by using L-type zeolite as a catalyst and carrying out the reaction in the liquid phase,
It was discovered that not only the conventional problems could be solved, but also 2,5-dihalogenated toluene could be produced with superior selectivity compared to conventional methods, and based on this knowledge, the present invention was completed.
すなわち、本発明は、触媒の存在下、２−ハロ
ゲン化トルエンをハロゲン化し２，５−ジハロゲ
ン化トルエンを製造する方法において、触媒とし
てＬ型ゼオライトを用い、液相中で反応を行うこ
とを特徴とする２，５−ジハロゲン化トルエンの
製造法である。 That is, the present invention is a method for producing 2,5-dihalogenated toluene by halogenating 2-halogenated toluene in the presence of a catalyst, which is characterized in that L-type zeolite is used as a catalyst and the reaction is carried out in a liquid phase. This is a method for producing 2,5-dihalogenated toluene.
本発明においてハロゲン化される２−ハロゲン
化トルエンとしては、ベンゼン核の２位がハロゲ
ン原子たとえば、フツ素、塩素、臭素等により置
換した、２−ハロゲン化トルエンをあげることが
できる。 Examples of the 2-halogenated toluene to be halogenated in the present invention include 2-halogenated toluene in which the 2-position of the benzene nucleus is substituted with a halogen atom, such as fluorine, chlorine, bromine, or the like.
また、本発明の方法において使用されるＬ型ゼ
オライトは、酸化ケイ素（SiO2）／酸化アルミ
ニウム（Al2O3）モル比が４〜８の結晶性アルミ
ナシリケイトであり、一般的には、それと同一の
Ｘ線回折スペクトルを有する合成ゼオライト、天
然ゼオライトであればよい。またイオン交換可能
なカチオンとしては、通常これがカリウムである
Ｌ型ゼオライトが入手される。この場合カリウム
をナトリウムでイオン交換することも可能であ
る。このイオン交換は公知のイオン交換方法が適
宜採用される。通常はナトリウムの硝酸塩、塩化
物等の水溶液で前記カリウム含有Ｌ型ゼオライト
を処理することにより容易にイオン交換される。
本発明のＬ型ゼオライトは、カリウムイオン以外
に勿論他のカチオン成分を含んでもよく、例えば
ナトリウム以外のＡ族、Ａ族、Ａ族、Ａ
族、Ａ族、の金属、遷移金属またはプロトン等
で交換したものが好ましく用いられる。またこれ
らのカチオンは、１種でも２種以上でもよく、触
媒は未焼成でも焼成してもよい。 Furthermore, the L-type zeolite used in the method of the present invention is a crystalline alumina silicate with a silicon oxide (SiO 2 )/aluminum oxide (Al 2 O 3 ) molar ratio of 4 to 8, and generally Any synthetic zeolite or natural zeolite having the same X-ray diffraction spectrum may be used. Further, as the ion-exchangeable cation, L-type zeolite, in which potassium is usually used, is available. In this case, it is also possible to ion-exchange potassium with sodium. For this ion exchange, a known ion exchange method is appropriately employed. Usually, the potassium-containing L-type zeolite is easily ion-exchanged by treating it with an aqueous solution of sodium nitrate, chloride, or the like.
The L-type zeolite of the present invention may of course contain other cation components other than potassium ions, such as A group other than sodium, A group, A group,
Those exchanged with Group A, Group A metals, transition metals, protons, etc. are preferably used. Further, the number of these cations may be one or two or more, and the catalyst may be uncalcined or calcined.
本発明の方法により２−ハロゲン化トルエンの
ハロゲン化を行なうには、２−ハロゲン化トルエ
ン１モル当り、Ｌ型ゼオライトを0.01ｇ以上、好
ましくは0.1ｇ以上、撹拌できる程度に混合して
沸点以下の温度でハロゲン化剤を導入する。反応
溶媒は所望により使用してもさしつかえない。ま
た反応温度は工業的には０℃〜沸点以下の温度で
行うのが適切である。この際のハロゲン化剤とし
ては、通常慣用されているハロゲン化剤を用いる
ことができる。たとえば塩素ガス、臭素、塩化ス
ルフリル、Ｎ−クロロサクシイミド、五塩化リ
ン、一酸化塩素等であるが、慣用されているハロ
ゲン化剤なら特に限定されることなく用いること
ができるが、好ましいのは、塩素ガスまたは臭素
である。また反応に際し窒素等の不活性ガスを使
用してもさしつかえない。上記反応においては減
圧、加圧のいづれでもよいが通常は常圧で行う。 In order to halogenate 2-halogenated toluene by the method of the present invention, 0.01 g or more, preferably 0.1 g or more of L-type zeolite is mixed per mole of 2-halogenated toluene to the extent that it can be stirred and the mixture is mixed to a level below the boiling point. Introduce the halogenating agent at a temperature of . The reaction solvent may be used as desired. Moreover, it is appropriate for the reaction temperature to be industrially carried out at a temperature of 0° C. to a temperature below the boiling point. As the halogenating agent in this case, a commonly used halogenating agent can be used. For example, chlorine gas, bromine, sulfuryl chloride, N-chlorosuccinimide, phosphorus pentachloride, chlorine monoxide, etc. Any commonly used halogenating agent can be used without particular limitation, but preferred are , chlorine gas or bromine. Furthermore, an inert gas such as nitrogen may be used during the reaction. The above reaction may be carried out under reduced pressure or increased pressure, but is usually carried out at normal pressure.
本発明の方法によれば、２−ハロゲン化トルエ
ンの５位を選択的に効率よくハロゲン化すること
により２，５−ジハロゲン化トルエンの生成が向
上するばかりでなく、反応率を95〜96％にあげて
も、トリハロゲン化トルエンの生成を、４〜５％
と低くおさえられるため、２，５−ジハロゲン化
トルエンの収量が向上する利点がある。さらに
は、反応、後処理操作が簡単であり、触媒の再使
用も可能であるなど、２，５−ジハロゲン化トル
エンを製造するのに適しており、その効果は、極
めて高いものである。 According to the method of the present invention, by selectively and efficiently halogenating the 5-position of 2-halogenated toluene, the production of 2,5-dihalogenated toluene is not only improved, but also the reaction rate is increased by 95 to 96%. However, the production of trihalogenated toluene was reduced by 4 to 5%.
This has the advantage of improving the yield of 2,5-dihalogenated toluene. Furthermore, the reaction and post-treatment operations are simple, and the catalyst can be reused, making it suitable for producing 2,5-dihalogenated toluene, and its effects are extremely high.
以下、実施例により本発明の方法を具体的に説
明する。 Hereinafter, the method of the present invention will be specifically explained with reference to Examples.
実施例 １
２−クロロトルエン126.6ｇ（１モル）及びＬ
型ゼオライト粉末（商品名；TSZ−502，東洋曹
達工業株式会社製）5.0ｇを反応器中で、加熱し
液温90℃になつたところで約30分間撹拌し、次に
塩素ガスを約0.22モル／時間の導入速度で吹き込
みながら4.5時間反応させた。反応液組成をガス
クロマトグラフイーにより分析したところ以下の
とおりであつた。Example 1 126.6 g (1 mol) of 2-chlorotoluene and L
5.0 g of type zeolite powder (trade name: TSZ-502, manufactured by Toyo Soda Kogyo Co., Ltd.) was heated in a reactor and stirred for about 30 minutes when the liquid temperature reached 90°C, and then about 0.22 mol of chlorine gas was added. The reaction was carried out for 4.5 hours while blowing at an introduction rate of /hour. The composition of the reaction solution was analyzed by gas chromatography and found to be as follows.
２−クロロトルエン 4.7％
２，３−ジクロロトルエン 7.3％
２，４−ジクロロトルエン 19.0％
２，５−ジクロロトルエン 55.8％
２，６−ジクロロトルエン 8.3％
トリクロロトルエン 4.9％
また反応に使用したＬ型ゼオライトは、次の化
学組成（原子吸光法）のものを使用した。2-chlorotoluene 4.7% 2,3-dichlorotoluene 7.3% 2,4-dichlorotoluene 19.0% 2,5-dichlorotoluene 55.8% 2,6-dichlorotoluene 8.3% Trichlorotoluene 4.9% L-type zeolite used in the reaction The following chemical composition (atomic absorption method) was used.
SiO2（wt％） ドライベース 64.6
％
Al2O3（wt％） 〃 17.8
％
Na2O（wt％） 〃 0.15
％
SiO2／Al2O3（モル比） 〃 6.2
K2O（wt％） 〃 15.9
％
実施例 ２
実施例１と同様の方法で反応を行い、触媒は繰
りかえし使用した。その結果、反応は正常に進み
反応生成物の組成は以下に示す。SiO 2 (wt%) dry base 64.6
% Al 2 O 3 (wt%) 〃 17.8
% Na 2 O (wt%) 〃 0.15
% SiO 2 /Al 2 O 3 (molar ratio) 〃 6.2
K2O (wt%) 〃 15.9
% Example 2 The reaction was carried out in the same manner as in Example 1, and the catalyst was used repeatedly. As a result, the reaction proceeded normally and the composition of the reaction product is shown below.
２−クロロトルエン 2.2％ ２，３−ジクロロトルエン 7.5％ ２，４−ジクロロトルエン 19.5％ ２，５−ジクロロトルエン 57.3％ ２，６−ジクロロトルエン 8.5％ トリクロロトルエン 5.0％ さらに触媒の再使用は可能であつた。2-chlorotoluene 2.2% 2,3-dichlorotoluene 7.5% 2,4-dichlorotoluene 19.5% 2,5-dichlorotoluene 57.3% 2,6-dichlorotoluene 8.5% Trichlorotoluene 5.0% Furthermore, it was possible to reuse the catalyst.
Claims (1)
ロゲン化し、２，５−ジハロゲン化トルエンを製
造する方法において、触媒としてＬ型ゼオライト
を用い、液相中で反応を行うことを特徴とする
２，５−ジハロゲン化トルエンの製造法。1. A method for producing 2,5-dihalogenated toluene by halogenating 2-halogenated toluene in the presence of a catalyst, characterized in that the reaction is carried out in a liquid phase using L-type zeolite as a catalyst. Method for producing 5-dihalogenated toluene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58082282A JPS59206322A (en) | 1983-05-11 | 1983-05-11 | Production of 2,5-dihalogenated toluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58082282A JPS59206322A (en) | 1983-05-11 | 1983-05-11 | Production of 2,5-dihalogenated toluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59206322A JPS59206322A (en) | 1984-11-22 |
| JPS6334130B2 true JPS6334130B2 (en) | 1988-07-08 |
Family
ID=13770155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58082282A Granted JPS59206322A (en) | 1983-05-11 | 1983-05-11 | Production of 2,5-dihalogenated toluene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59206322A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02153835A (en) * | 1988-12-05 | 1990-06-13 | Sumitomo Electric Ind Ltd | Production of preform for optical fiber |
-
1983
- 1983-05-11 JP JP58082282A patent/JPS59206322A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02153835A (en) * | 1988-12-05 | 1990-06-13 | Sumitomo Electric Ind Ltd | Production of preform for optical fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59206322A (en) | 1984-11-22 |
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