JPS59219241A - Oxyiodination of aromatic compound - Google Patents
Oxyiodination of aromatic compoundInfo
- Publication number
- JPS59219241A JPS59219241A JP58094098A JP9409883A JPS59219241A JP S59219241 A JPS59219241 A JP S59219241A JP 58094098 A JP58094098 A JP 58094098A JP 9409883 A JP9409883 A JP 9409883A JP S59219241 A JPS59219241 A JP S59219241A
- Authority
- JP
- Japan
- Prior art keywords
- benzene
- oxyiodination
- reaction
- group
- monoiodobenzene
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
本発明ハ、ベンゼン、モノヨードベンゼン又はその両者
をオキシヨウ素化法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for oxyiodinating benzene, monoiodobenzene, or both.
さらに詳しくは、ベンゼン、モノヨードベンゼン又はそ
の両者を、ヨウ素、ヨウ化水素又はその両者と酸素を用
いてオキシヨウ素化する際に、触媒として、シリカ／ア
ルミナ比が１０以上で、カチオンとしてプロトン、Ｉｂ
族、ｙｂ族、■ｂ１１１ｃ。More specifically, when benzene, monoiodobenzene, or both are oxyiodinated using iodine, hydrogen iodide, or both and oxygen, a silica/alumina ratio of 10 or more is used as a catalyst, protons are used as cations, Ib
family, yb family, ■b111c.
■族の金属イオンの少くとも一種を含む結晶性アルミノ
クリケートを用いる小を特徴とするベンゼン、モノヨー
ドベンゼン又はその両者のオキシヨウ素化法に関するも
のである。The present invention relates to a method for oxyiodination of benzene, monoiodobenzene, or both, characterized by the use of a crystalline aluminosilicate containing at least one type of group metal ion.
ヨードベンゼン類は、各種アミン類の中間原料として有
用なものであシ、特に、ノぞ２シヨートベンゼンは、ア
ラミド系繊維の原料である。ｅラフエニレンジアミンの
中間原料として有用なものである。Iodobenzenes are useful as intermediate raw materials for various amines, and in particular, 2-shotobenzene is a raw material for aramid fibers. e It is useful as an intermediate raw material for rough phenylenediamine.
この／ぞラジョードベンゼンは、現在、ベンゼン又はヨ
ードベンゼンを、酸触媒の存在下、液相でヨワ素化する
事によって製造されている。しかしながらこの方法では
、ショートベンゼン中のノソラ体の割合は、８０〜９０
％であシ、必ずオルソ体が混入するとい９欠点と、反応
によって原料のヨウ素の半分がヨウ化水素になるため、
ヨウ素基準で５０％でしかショートベンゼンが得られな
いという欠点がおった。又、ベンゼン又はヨードベンゼ
ンを液相において、酸触媒と酸化融媒を用いて、ヨウ素
と酸素から酸化的に・ショートベンゼンにする方法４提
案されているがこの方法もノξう体の割合は８０〜９０
％で、オルソ体の混入という欠点を有している。Lajodobenzene is currently produced by iodination of benzene or iodobenzene in the liquid phase in the presence of an acid catalyst. However, in this method, the proportion of nosola forms in short benzene is 80 to 90
%, the 9 drawbacks are that the ortho isomer is always mixed in, and half of the iodine in the raw material becomes hydrogen iodide during the reaction.
The drawback was that short benzene could only be obtained at 50% iodine. In addition, a method has been proposed in which benzene or iodobenzene is oxidatively converted to short benzene from iodine and oxygen using an acid catalyst and an oxidizing solvent in the liquid phase, but this method also has a 80-90
%, which has the disadvantage of contamination with ortho forms.
そこで、本発明者らは、これらの問題を解決すべく鋭意
検討を重ねた結果、シリカ／アルミナ比が１０以上で、
カチオンとして、プロトン、Ｉｂ族、■ｂ族、■ｂ族、
■ｂ族、■族の金属イオンの少くとも一種を含む結晶性
アルミノシリケートを触媒として用いる場合にノクラジ
ョードベンー１シンが高収率で得られる事を見い出し本
発明を完成するに至った。Therefore, as a result of intensive studies to solve these problems, the present inventors found that when the silica/alumina ratio is 10 or more,
As a cation, proton, Ib group, ■b group, ■b group,
The present inventors have discovered that noclajodoben-1-sine can be obtained in high yield when a crystalline aluminosilicate containing at least one of the metal ions of Groups 2b and 2 is used as a catalyst, and the present invention has been completed.
すなわち、本発明は、ベンゼン、モノヨードベンゼン又
はその両者をヨウ素、ヨウ化水素又はその両者と酸素を
用いてオキンヨウ素化する際に、触媒としてシリカ／ア
ルミナ比が１０以上で、カチオンとしてプロトン、Ｉｂ
族、■ｂ族、Ｖｌｂ族、■ｂ族、■族の金属イオンの少
くとも一種を含む結晶性アルミ／シリケートを用いる事
を特徴とするベンゼン、モノヨードベンゼン又はその両
者のオキシヨウ素化法である。That is, the present invention provides for the oxidation of benzene, monoiodobenzene, or both using iodine, hydrogen iodide, or both and oxygen, with a silica/alumina ratio of 10 or more as a catalyst, and protons, Ib
A method for the oxyiodination of benzene, monoiodobenzene, or both, which is characterized by using crystalline aluminum/silicate containing at least one metal ion of the group III, III group, Vlb group, III group, or III group. be.
本発明の特徴は、ショートベンゼン中の・ぞう体の割合
が、９８％以上と非常に高い事である。この事は、本発
明に用いる結晶性アルミノシＩＪケートがパラショート
ベンゼンに文ｔしてＩト常に筒いノ杉状選択性を有する
ためと考えられる。A feature of the present invention is that the proportion of elephants in short benzene is extremely high, at 98% or more. This is considered to be because the crystalline aluminosilicate used in the present invention always has a cylindrical selectivity toward parachotobenzene.
本発明に用いられる７１ツ力／アルミナ比力Ｅ１０以上
の結晶性アルミノシ１）ケートとは、Ｘ線回折図におい
て、表１の回折、Ｒターンを有″ｊ−るＡＺ−１と呼ば
れるゼオライト（％許出願昭５７−２２８２８３参照）
モーピルオイル社の開発したＺ８Ｍ−ｓ（０８Ｐこれら
の中でも特ＫＡＺ−１、Ｚ８Ｍ−５、Ｚ８Ｍ−１１力五
好ましい。これらの結晶性アルミノ７１）ケートはゾロ
トン、Ｉｂ族、ｙｂ族、■ｂ族、■ｂ族、■族の金属イ
オンの少くとも一種のカチオンでイオン交換し７て触媒
として用いらｉする。これらカチオンの具体例としては
、プロトン又は、Ｏｕ ＋ Ａｇ ＋ ｖｔ ”Ｒｅ
、Ｆｅ 、Ｃｏ 、Ｎｉ 、Ｒｕ 、Ｒｈ 、Ｐｄ 、
Ｏｓ 、 Ｉｒ 、Ｐｔ等の金属イオンがあげられる。The crystalline aluminosilicate used in the present invention with 71 strength/alumina specific strength E10 or more 1) cate is a zeolite called AZ-1 which has the diffraction shown in Table 1 and an R turn in the X-ray diffraction diagram. (See patent application No. 57-228283)
Z8M-s (08P) developed by Mopil Oil Co., Ltd. Among these, KAZ-1, Z8M-5, and Z8M-11 are particularly preferred. (2) Ion-exchange with at least one cation of group B or group (2) metal ions and use as a catalyst. Specific examples of these cations include protons, Ou + Ag + vt ”Re
, Fe, Co, Ni, Ru, Rh, Pd,
Examples include metal ions such as Os, Ir, and Pt.
特にＯｕイオンを含む触媒が好ましい。またこれらのカ
チオンは結晶性アルミノシリケートのイオン交換容量の
１〜１００％、好ましくは１０〜１００％の範囲で含ま
れる。In particular, catalysts containing Ou ions are preferred. Further, these cations are contained in an amount of 1 to 100%, preferably 10 to 100%, of the ion exchange capacity of the crystalline aluminosilicate.
本発明におけるヨウ素化剤としてはヨウ素、ヨウ化水素
が用いられる。Iodine and hydrogen iodide are used as the iodinating agent in the present invention.
本発明における原料のベンゼン類／ｈ又はＨｌのモル比
は、０．０１〜５０の範囲、好ま１− ＜は０．１〜１
０の範囲で行なわれる。、また酸素は、ベンゼン類の爆
発範囲に応じて安全な濃度が選ばれる。これらの原料ガ
スは、そのまま導入しても、不活性ガスで希釈導入し７
てもよい。The molar ratio of benzenes/h or Hl of the raw materials in the present invention is in the range of 0.01 to 50, preferably 1-<0.1 to 1
This is done in the range of 0. Also, a safe concentration of oxygen is selected depending on the explosive range of benzenes. These raw material gases can be introduced as is or diluted with an inert gas.
It's okay.
本発明における反応温度は、一般的に２００〜４００℃
、好ましくは２００〜３００℃の温度範囲で行なわれる
。The reaction temperature in the present invention is generally 200 to 400°C.
, preferably at a temperature range of 200 to 300°C.
本発明は、常圧または加圧で行なわれ、反応方式は固定
床、流動床等を用いた流通反応方式が好ましい。The present invention is carried out under normal pressure or increased pressure, and the reaction method is preferably a flow reaction method using a fixed bed, a fluidized bed, or the like.
次に、本発明を実施例を用いて説明する。Next, the present invention will be explained using examples.
実施例１
シリカゲル（３０ｗｔ％８ｉ０２）、硫酸アルミニウム
（Ａ／ 鵞（８０ａ ）ｓ ・１８ Ｈ２Ｏ） ＊ Ｎ
ａ ＯＨ＊ １ ｖ ８−ジアミノー４−アミノメチ
ルオクタン及び水から特許出願昭５７−２２８２８３号
の実施例に従ってゼオライ） ＡＺ−１を合成した。得
られたＡＺ−１のシリカ／アルミナ比は５０であった。Example 1 Silica gel (30wt%8i02), aluminum sulfate (A/ 80a s ・18 H2O) *N
Zeolite AZ-1 was synthesized from a OH* 1 v 8-diamino-4-aminomethyloctane and water according to the example of patent application No. 57-228283. The silica/alumina ratio of the obtained AZ-1 was 50.
このＡＺ−１を１０ｗｔ％０ｕＯ１ｚ水溶液中で、６０
′ｃ。This AZ-1 was dissolved in a 10wt% 0uO1z aqueous solution for 60
'c.
２４時間イオン交換を行β、ベンゼンのオキシヨウ素化
反応の触媒に用いた。After 24 hours of ion exchange, β was used as a catalyst for the oxyiodination reaction of benzene.
反応条件は、１． ： ０＠Ｈ６：０．＝ １ ： ８
： ０．５ 、５Ｖ＝２０００ ｈｒ−”、反応温度
： ２５０ｔｌ：、常圧固定床流通反応で行った。The reaction conditions are 1. : 0@H6:0. = 1 : 8
: 0.5, 5V=2000 hr-'', reaction temperature: 250 tl: The reaction was carried out in a normal pressure fixed bed flow reaction.
反工６開始後２〜３時間の成績は、ベンゼン転化率＝ｔ
Ｓ％、ヨウ素化ぺ／ゼン選択率＝９６％、ヨウ素化ベン
ゼン中の生成物の分布は次の通シであった。The results for 2 to 3 hours after starting the process 6 are benzene conversion rate = t
S%, iodinated p/zene selectivity = 96%, the distribution of products in the iodinated benzene was as follows:
実施例２
実施例１と同じ触媒を用いて、モノヨード４ンゼンのオ
キシヨウ素化反応を行った。Example 2 Using the same catalyst as in Example 1, an oxyiodination reaction of monoiodo-4-benzene was carried out.
反応条件は、Ｉ、 ： ０＠Ｈ５Ｌ ： Ｏ，＝１ ：
４ ： ０．６．８ｖ＝ ５０００ ｈｒ ’、反応
温度＝２８０℃、常圧固定床流通反応で行った。The reaction conditions are I,: 0@H5L: O,=1:
4: 0.6.8v=5000 hr', reaction temperature=280°C, normal pressure fixed bed flow reaction.
反応開始後３〜４時間の成績は、モノヨードベンゼン転
化率＝４５％、ジョーＰベンゼン選択率＝９５％、ショ
ートベンゼン中のＡう体の割合＝１００％であった。The results 3 to 4 hours after the start of the reaction were as follows: monoiodobenzene conversion rate = 45%, Joe P benzene selectivity = 95%, and proportion of A caries in short benzene = 100%.
比較例
Ｙ型ゼオライトを１０ｗｔ％０ｕＯ４２水溶液中で６０
℃、３０時間イオン交換してモノヨードベンゼンのオキ
シヨウ素化を、実施例２と同じ条件で行った。Comparative Example Y-type zeolite was dissolved in a 10wt% 0uO
Oxyiodination of monoiodobenzene was carried out under the same conditions as in Example 2 by ion exchange at ℃ for 30 hours.
反応開始後３〜４時間の成績は、モノヨードベンゼン転
化率＝４０％、ショートベンゼン選択率＝９０％、ショ
ートベンゼン中のノｅ２体の割合９０％、オルソ体の割
合１０％であった。The results 3 to 4 hours after the start of the reaction were as follows: monoiodobenzene conversion rate = 40%, short benzene selectivity = 90%, proportion of noe2 form in short benzene was 90%, and proportion of ortho form was 10%.
実施例３
Ｑｂｒａｎｄケイ酸塩水溶液（Ｎａ２０ ： ８．９ｗ
ｔ％、Ｓｉｎｇ：２８．９ｗｔ％）、硫酸アルミニウム
（Ａｌｔ （８０＜）ｓ ’１８Ｈ１０）、 ｆ ド
ラフロビルアンモニウムブロマイド及び水から、ＵＳＰ
３７０２８８６号に従ツーＣＺＳＭ−５を合成した。Example 3 Qbrand silicate aqueous solution (Na20: 8.9w
t%, Sing: 28.9wt%), aluminum sulfate (Alt(80<)s'18H10), f from draflobylammonium bromide and water, USP
Two CZSM-5 was synthesized according to No. 3702886.
得られた７８Ｍ−５のシリカ／アルミナ比は４５であっ
た。The silica/alumina ratio of the obtained 78M-5 was 45.
この７８Ｍ−５を、２０ ｗｔ ％ ０ｕ０１４水溶液
中で室温で２４時間イオン交換してモノヨード（ンゼン
のオキシヨウ素化反応の触媒として用いた。This 78M-5 was ion-exchanged in a 20 wt % 0u014 aqueous solution at room temperature for 24 hours and used as a catalyst for the oxyiodination reaction of monoiodo.
反応条件は、ＩｔＩｔ： ＵｓＨｓｌ ： 馬＝１ ：
１ ： １．８ｖ＝３０００ ｈｒ−”、反応温度＝
２６０℃、常圧固定床流通反応で行った。The reaction conditions are ItIt: UsHsl: Horse=1:
1: 1.8v=3000 hr-”, reaction temperature=
The reaction was carried out in a fixed bed flow reaction at 260° C. and normal pressure.
反応開始後％ ４〜５時間の成績は、モノヨードベンセ
ン転化率＝４ｇ％、ショートベンゼン選択率＝９５％、
ショートベンゼン中の）ｅう体の割合＝９８％であった
。% After the start of the reaction, the results for 4 to 5 hours were: monoiodobenzene conversion rate = 4g%, short benzene selectivity = 95%,
The proportion of caries (in short benzene) was 98%.
実施例４
シ１７カゲｋ （３０ｗｉ ９／、 ８ｉ０２）、硫酸
アルミニウム（Ａ／鵞（８０ａ）ｓ ・１８ ＨｔＯ）
、Ｎａ０Ｈｓ オクタメチレンｄアミン及び水から特
開昭５４−５２６９９号の実施例に従いＺＳＭ−１１を
合成した。得られたＺＳＭ−１１のシリカ／アルミナ比
は３０であった。Example 4 Shi17 Kagek (30wi 9/, 8i02), aluminum sulfate (A/Rose (80a)s ・18 HtO)
, Na0Hs, octamethylene d amine and water according to the example of JP-A No. 54-52699. The silica/alumina ratio of the obtained ZSM-11 was 30.
この７８Ｍ−１１を、２０ｗｔ％０ｕＯｊ’２水溶液中
で６０℃、２４時間イオン交換してベンゼンのオキシヨ
ウ素化反応の触媒として用いた。This 78M-11 was ion-exchanged in a 20 wt% 0uOj'2 aqueous solution at 60°C for 24 hours and used as a catalyst for the benzene oxyiodination reaction.
反応条件は、Ｉ！： （３，Ｈ＠：Ｏ，＝１ ： ４
： ０．５、８ｖ＝３０００ ｈｒ−’、反応温度：２
３０℃、常圧固定床流通反応で行った。The reaction conditions were I! : (3,H@:O,=1:4
: 0.5, 8v=3000 hr-', reaction temperature: 2
The reaction was carried out in a fixed bed flow reaction at 30° C. and normal pressure.
反応開始後、２〜３時間の成績は、ベンゼン転化率＝３
０％、ヨウ素化ベンゼン選択率＝９５％、ヨウ素化ベン
ゼン中の生成物の分布は次の通シであった。The results for 2 to 3 hours after the start of the reaction were as follows: benzene conversion rate = 3
0%, iodinated benzene selectivity = 95%, the distribution of products in the iodinated benzene was as follows.
実施例５
シリカゲル（ａｏｗｔ％８ｉ０ｉ）、硫酸アルミニウム
（Ａｌｚ （ＳＯ４）３・１８ Ｈ２Ｏ）、ＮａＯＨ１
１，８−、，７７ミ／−４−アミノメチルオクタン及び
水から特許出願昭５７−２２８２８３号の実施例に従っ
てゼオライ） ＡＺ−１を合成した。得られたＡＺ−１
のシリカ／アルミナ比は６０であった。Example 5 Silica gel (aowt% 8i0i), aluminum sulfate (Alz (SO4)3.18 H2O), NaOH1
Zeolite AZ-1 was synthesized from 1,8-, ,77mi/-4-aminomethyloctane and water according to the example of patent application No. 57-228283. Obtained AZ-1
The silica/alumina ratio was 60.
このＡＺ−１を１０ｗｔ％ＮＨ４ｃｌ水溶液中で、６０
℃、２４時間イオン交換して濾過、洗浄後４００’Ｃ８
時間空気焼成して、プロトン型のＡＺ−１を得た。This AZ-1 was dissolved in a 10 wt% NH4Cl aqueous solution for 60 min.
℃, 400'C8 after 24 hours ion exchange, filtration and washing
Air calcination was performed for a period of time to obtain proton type AZ-1.
これを触媒に用いて４ンゼンのオキシヨウ素化反応を行
った。Using this as a catalyst, an oxyiodination reaction of 4-benzene was carried out.
反応条件は、実施何重と同じで行った。The reaction conditions were the same as those used in multiple experiments.
反応開始後２〜３時間の成績はベンセン転化率＝１０％
、ヨウ素化ベンゼン選ツ〈率＝９６％、ヨウ素化ベンゼ
ン中の生成物の分布は次の辿シであった。The results for 2 to 3 hours after the start of the reaction were benzene conversion rate = 10%.
The distribution of products in the iodinated benzene was as follows.
実施例６
実施例１で得られたＡＺ−１を各種金属カチオンで交換
シてモノヨードベンゼンのオキシヨウ素化反応を行った
。Example 6 AZ-1 obtained in Example 1 was exchanged with various metal cations to carry out an oxyiodination reaction of monoiodobenzene.
反応条件は、実施例２と同じである。The reaction conditions are the same as in Example 2.
反応開始後、３〜４時間の成績を次の表に示す。The results obtained 3 to 4 hours after the start of the reaction are shown in the following table.
、手続補正書（自発）
昭和５９年４月７０日
特許庁長官 若 杉 和 夫 殿
１、事件の表示 昭和５８年特許願第 ９４０９８
号ａ 発明の名称
芳香族化合物のオキシヨウ素化法
ａ 補正をする者
事件との関係 特許出願人
大阪府大阪市北区堂島浜１丁目２番６号４、補正の対象
明細書の「特許請求の範囲」の欄
＆ 補正の内容
別紙の通り
特許請求の範囲
（１） ベンゼン、モノヨードベンゼン又はその両者
ヲヨウ素、ヨウ化水素又はその両者と酸素を用いてオキ
シヨウ素化する際に、触媒としてシリカ／アルミナ比が
１０以上でカチオンとして、プロトン、ｌｂ族、ｖｂ族
、■ｂ族、■ｂ族、■族の金属イオンの少くとも一種を
含む結晶性アルミノシリケートを用いる事を特徴とする
ベンゼン、モノヨードヘンセン又はその両者のオキシヨ
ウ素化法（２）前記結晶性アルミノシリケートがＸ線回
折図において１表１の回折パターンを有する事’ｃ ％
徴とする特許請求の範囲第１項記載の方法
ただし、Ｘ線回折分析に用いるＸ線はＣｕ Ｋα線であ
る。, Procedural amendment (voluntary) April 70, 1980 Director-General of the Patent Office Kazuo Wakasugi 1, Indication of case Patent application No. 94098 of 1982
No. a Name of the invention Method for oxyiodination of aromatic compounds a Relationship to the case of the person making the amendment Patent applicant 1-2-6-4 Dojimahama, Kita-ku, Osaka-shi, Osaka Prefecture Scope of Claims (1) Claims (1) oxyiodination of benzene, monoiodobenzene, or both using iodine, hydrogen iodide, or both and oxygen, using silica as a catalyst / alumina ratio of 10 or more and a benzene characterized by using a crystalline aluminosilicate containing at least one of protons, LB group, VB group, ■B group, ■B group, and ■ group metal ions as cations, Oxyiodination method of monoiodohensen or both (2) The crystalline aluminosilicate has a diffraction pattern shown in Table 1 in an X-ray diffraction diagram.
The method according to claim 1, characterized in that the X-rays used in the X-ray diffraction analysis are Cu Kα rays.
（３）前記結晶性アルミノシリケートが、Ｚ８Ｍ−ｓＺ
ＳＮ−１１である事を特徴とする特許請求の範囲第１項
記載の方法(3) The crystalline aluminosilicate is Z8M-sZ
The method according to claim 1, characterized in that the method is SN-11.
Claims (1)
者をヨウ素、ヨウ化水素又はその両者と酸素を用いてオ
キシヨウ素化する際に、触媒としてシリカ／アルミナ比
が１０以上でカチオンとして、プロトン、′Ｉｂ族、ｙ
ｂ族、■ｂ族、■ｂ族、■族の金属イオンの少くとも一
種を含む結晶性アルミノシリケートを用いる事を特徴と
するベンゼン、モノヨードベンゼン又はその両者のオキ
７ヨウ素化法（２） 前記結晶性アルミノシリケート
がＸ線回折図において、表１の回折／（’ターンを有す
る事を特徴とする特許請求の範囲第１項記載の方法以下
余白 ただし、Ｘ線回折分析に用いるＸ線はＯｕ Ｋａ線でお
る。 （３） 前記結晶性アルミノシリケートが、Ｚ８Ｍ−
５Ｚ８Ｎ−１１である事を特徴とする特許請求の範囲第
１項記載の方法[Claims] (i)! , "When oxyiodinating benzene, monoiodobenzene, or both using iodine, hydrogen iodide, or both and oxygen, a silica/alumina ratio of 10 or more is used as a catalyst, and as a cation, protons, 'Ib group ,y
A method for the oxy7-iodination of benzene, monoiodobenzene, or both, characterized by using a crystalline aluminosilicate containing at least one type of metal ion of group b, group ■b, group ■b, or group ■ (2) The method according to claim 1, wherein the crystalline aluminosilicate has a diffraction/(' turn in Table 1 in an X-ray diffraction diagram. (3) The crystalline aluminosilicate is Z8M-
5Z8N-11, the method according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58094098A JPS59219241A (en) | 1983-05-30 | 1983-05-30 | Oxyiodination of aromatic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58094098A JPS59219241A (en) | 1983-05-30 | 1983-05-30 | Oxyiodination of aromatic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59219241A true JPS59219241A (en) | 1984-12-10 |
Family
ID=14100967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58094098A Pending JPS59219241A (en) | 1983-05-30 | 1983-05-30 | Oxyiodination of aromatic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59219241A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6191142A (en) * | 1984-10-05 | 1986-05-09 | モンテデイペ・ソチエタ・ペル・アツイオニ | Synthesis of iodobenzene |
| JPS61106527A (en) * | 1984-10-16 | 1986-05-24 | モンテデイペ・ソチエタ・ペル・アツイオニ | Synthesis of iodobenzene |
| EP0256479A2 (en) * | 1986-08-11 | 1988-02-24 | ECP ENICHEM POLIMERI S.r.l. | Process for the catalytic transhalogenation of a poly-iodo-benzene |
| EP0256480A2 (en) * | 1986-08-11 | 1988-02-24 | ECP ENICHEM POLIMERI S.r.l. | Process for the catalytic trans-halogenation of a polyiodo-benzene and, in particular, of a di-iodo-benzene |
| WO1988007509A1 (en) * | 1987-03-25 | 1988-10-06 | Eastman Kodak Company | Process for preparing iodinated substituted aromatic compounds |
| US4788356A (en) * | 1987-10-16 | 1988-11-29 | Eastman Kodak Company | Novel method for oxyiodination product partial purification |
| US4788355A (en) * | 1987-10-16 | 1988-11-29 | Eastman Kodak Company | Oxyiodination catalyst |
| US4810826A (en) * | 1988-03-17 | 1989-03-07 | Eastman Kodak Company | Liquid-phase process for the oxyiodination of naphthalene |
| WO2004069772A1 (en) * | 2003-02-10 | 2004-08-19 | Mitsubishi Gas Chemical Company, Inc. | Process for production of iodine compounds and process for production of high-purity 5-iodo-2-methylbenzoic acid |
| WO2005003073A1 (en) * | 2003-07-03 | 2005-01-13 | Mitsubishi Gas Chemical Company, Inc. | Process for producing 5-iodo-2-methylbenzoic acid |
| WO2008082082A1 (en) | 2006-12-29 | 2008-07-10 | Sk Chemicals Co., Ltd. | Method of preparing mono-iodo benzene through transiodination |
| WO2010077026A2 (en) | 2008-12-31 | 2010-07-08 | 에스케이케미칼주식회사 | Cation exchange zeolite catalyst, and method for producing mono-iodo benzene through a transiodination reaction using same |
-
1983
- 1983-05-30 JP JP58094098A patent/JPS59219241A/en active Pending
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0248530B2 (en) * | 1984-10-05 | 1990-10-25 | Montedipe Spa | |
| JPS6191142A (en) * | 1984-10-05 | 1986-05-09 | モンテデイペ・ソチエタ・ペル・アツイオニ | Synthesis of iodobenzene |
| JPS61106527A (en) * | 1984-10-16 | 1986-05-24 | モンテデイペ・ソチエタ・ペル・アツイオニ | Synthesis of iodobenzene |
| EP0183579A1 (en) * | 1984-10-16 | 1986-06-04 | MONTEDIPE S.r.l. | Method for the synthesis of iodobenzene |
| JPH0251534B2 (en) * | 1984-10-16 | 1990-11-07 | Montedipe Spa | |
| EP0256479A2 (en) * | 1986-08-11 | 1988-02-24 | ECP ENICHEM POLIMERI S.r.l. | Process for the catalytic transhalogenation of a poly-iodo-benzene |
| EP0256480A2 (en) * | 1986-08-11 | 1988-02-24 | ECP ENICHEM POLIMERI S.r.l. | Process for the catalytic trans-halogenation of a polyiodo-benzene and, in particular, of a di-iodo-benzene |
| WO1988007509A1 (en) * | 1987-03-25 | 1988-10-06 | Eastman Kodak Company | Process for preparing iodinated substituted aromatic compounds |
| US4788355A (en) * | 1987-10-16 | 1988-11-29 | Eastman Kodak Company | Oxyiodination catalyst |
| US4788356A (en) * | 1987-10-16 | 1988-11-29 | Eastman Kodak Company | Novel method for oxyiodination product partial purification |
| US4810826A (en) * | 1988-03-17 | 1989-03-07 | Eastman Kodak Company | Liquid-phase process for the oxyiodination of naphthalene |
| WO2004069772A1 (en) * | 2003-02-10 | 2004-08-19 | Mitsubishi Gas Chemical Company, Inc. | Process for production of iodine compounds and process for production of high-purity 5-iodo-2-methylbenzoic acid |
| US7750182B2 (en) | 2003-02-10 | 2010-07-06 | Mitsubishi Gas Chemical Company, Inc. | Process for production of iodine compounds and process for production of high-purity 5-iodo-2-methylbenzoic acid |
| US7642374B2 (en) | 2003-07-03 | 2010-01-05 | Mitsubishi Gas Chemical Company, Inc. | Process for producing 5-iodo-2-methylbenzoic acid |
| WO2005003073A1 (en) * | 2003-07-03 | 2005-01-13 | Mitsubishi Gas Chemical Company, Inc. | Process for producing 5-iodo-2-methylbenzoic acid |
| WO2008082082A1 (en) | 2006-12-29 | 2008-07-10 | Sk Chemicals Co., Ltd. | Method of preparing mono-iodo benzene through transiodination |
| US7906694B2 (en) | 2006-12-29 | 2011-03-15 | Sk Chemicals Co., Ltd. | Method of preparing mono-iodo benzene through transiodination |
| KR101112173B1 (en) * | 2006-12-29 | 2012-02-24 | 에스케이케미칼주식회사 | Method of preparing mono-iodo benzene through transiodination |
| WO2010077026A2 (en) | 2008-12-31 | 2010-07-08 | 에스케이케미칼주식회사 | Cation exchange zeolite catalyst, and method for producing mono-iodo benzene through a transiodination reaction using same |
| US9108180B2 (en) | 2008-12-31 | 2015-08-18 | Sk Chemicals Co., Ltd. | Cation-exchanged zeolite catalyst and process for producing mono-iodo benzene through transiodination by using it |
| US9138730B2 (en) | 2008-12-31 | 2015-09-22 | Sk Chemicals Co., Ltd. | Cation-exchanged zeolite catalyst and process for producing mono-iodo benzene through transiodination by using it |
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