JPH03167153A - Production of 3,5-diiodosalicylic acid - Google Patents
Production of 3,5-diiodosalicylic acidInfo
- Publication number
- JPH03167153A JPH03167153A JP1306400A JP30640089A JPH03167153A JP H03167153 A JPH03167153 A JP H03167153A JP 1306400 A JP1306400 A JP 1306400A JP 30640089 A JP30640089 A JP 30640089A JP H03167153 A JPH03167153 A JP H03167153A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- chloride
- salicylic acid
- mol
- reaction
- 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
- DHZVWQPHNWDCFS-UHFFFAOYSA-N 2-hydroxy-3,5-diiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1O DHZVWQPHNWDCFS-UHFFFAOYSA-N 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 7
- 239000011592 zinc chloride Substances 0.000 claims abstract description 5
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 4
- ORVCATCRRUXRCE-UHFFFAOYSA-N 2-iodooxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OI ORVCATCRRUXRCE-UHFFFAOYSA-N 0.000 claims description 9
- 229910000831 Steel Inorganic materials 0.000 claims description 4
- 239000010959 steel Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 26
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 abstract description 13
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract description 13
- 229960004889 salicylic acid Drugs 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 229910001868 water Inorganic materials 0.000 abstract description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 239000011630 iodine Substances 0.000 abstract description 4
- 229910052740 iodine Inorganic materials 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 2
- 229940124339 anthelmintic agent Drugs 0.000 abstract description 2
- 239000000921 anthelmintic agent Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000011780 sodium chloride Substances 0.000 abstract description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 5
- 229940063656 aluminum chloride Drugs 0.000 description 5
- 229940009861 aluminum chloride hexahydrate Drugs 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SWDNKOFGNPGRPI-UHFFFAOYSA-N 2-hydroxy-5-iodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC=C1O SWDNKOFGNPGRPI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LFGVUBNSHXWLSE-UHFFFAOYSA-N ICl.Cl Chemical compound ICl.Cl LFGVUBNSHXWLSE-UHFFFAOYSA-N 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CAYKLJBSARHIDI-UHFFFAOYSA-K trichloroalumane;hydrate Chemical compound O.Cl[Al](Cl)Cl CAYKLJBSARHIDI-UHFFFAOYSA-K 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
Abstract
Description
【発明の詳細な説明】 Ｅａ業上の利用分野］ ３．５−ジヨードサリチル酸の製造方法に関する。[Detailed description of the invention] Field of use in Ea industry] The present invention relates to a method for producing 3.5-diiodosalicylic acid.
３．５−ジヨードサリチル酸は動物用の駆虫剤の原料と
して用いられる。3.5-diiodosalicylic acid is used as a raw material for anthelmintics for animals.
［従来の技術］
一塩化沃素を用いた３、５−ジヨードサリチル酸の製造
方法として０ＲＧＡＮＩＣ５ＹＮＴＩＩＥＳＥＳ Ｃ０
ＬＬＥＣＴＩＯＮ ＶＯＬＵＭＥ ｐ３４３に酢酸を溶
媒とした方法がある。[Prior art] 0RGANIC5YNTIIIESES C0 as a method for producing 3,5-diiodosalicylic acid using iodine monochloride
There is a method using acetic acid as a solvent in LLECTION VOLUME p343.
しかし、この方法では、酢酸を用いるために臭気がひど
く、実際の製造に際して除外設備等が必要となり経済性
が良くない、また、廃液中に高価な沃素が含まれており
、回収するためには溶媒除去等の処理を行なわなければ
ならず操作上煩雑になる。また、酢酸等の溶媒に目的物
である３、５−ジヨードサリチル酸が溶解するため収率
が低（なる。However, since this method uses acetic acid, it has a bad odor, requires equipment to exclude it during actual production, and is not economical.Also, the waste liquid contains expensive iodine, and it is difficult to recover it. Processing such as solvent removal must be carried out, making the operation complicated. In addition, the yield is low because the target product, 3,5-diiodosalicylic acid, is dissolved in a solvent such as acetic acid.
さらに、酢酸等の溶媒を用いない場合、すなわら、水中
でサリチル酸と一塩化沃素とにより３．５〜シヨートサ
リチル酸を製造した場合も、反応時間が長く、また中間
体である３−ヨードサリチル酸や５−ヨードサリチル酸
のモノヨードサリチル酸が多く残存する。このモノヨー
ド体は３．５−ジヨードサリチル酸の結晶品質を特に純
度を著しく低下させるために極力減少させる必要がある
。Furthermore, when a solvent such as acetic acid is not used, that is, when 3.5-syotosalicylic acid is produced from salicylic acid and iodine monochloride in water, the reaction time is long, and the intermediate 3-iodo A large amount of monoiodosalicylic acid such as salicylic acid and 5-iodosalicylic acid remains. This monoiodo compound must be reduced as much as possible because it significantly reduces the crystal quality of 3,5-diiodosalicylic acid, especially its purity.
［発明が解決しようとする課題］
そこで、本発明は水溶液中で高収率でかつ高品質の３．
５−ジヨードサリチル酸を製造する方法を提供すること
を課題とする。[Problems to be Solved by the Invention] Therefore, the present invention provides 3. high yield and high quality in an aqueous solution.
An object of the present invention is to provide a method for producing 5-diiodosalicylic acid.
［課題を解決するための手段］
本発明者らは、上記の課題を解決するために鋭意検討し
た結果、有機溶剤を用いない水溶液中で一塩化沃素とサ
リチル酸を反応させる方法において塩化第二鉄や塩化ア
ルミニウム等の化合物を添加することにより、これらの
課題が解決することを見いだし、本発明を完成するに至
った。[Means for Solving the Problems] As a result of intensive studies to solve the above problems, the present inventors have discovered that ferric chloride can be used in a method of reacting iodine monochloride and salicylic acid in an aqueous solution without using an organic solvent. It has been discovered that these problems can be solved by adding compounds such as aluminum chloride and aluminum chloride, and the present invention has been completed.
すなわち、水存在下一塩化沃素とサリチル酸を反応させ
て３．５−ジヨードサリチル酸を製造する方法において
、塩化第二鉄、塩化アルミニウム、塩化亜鉛、塩化鋼、
硫酸及びリン酸のうち選ばれた１種類以上の化合物を添
加することを特徴とする３゜５−ジヨードサリチル酸の
製造方法である。That is, in a method for producing 3,5-diiodosalicylic acid by reacting iodine monochloride and salicylic acid in the presence of water, ferric chloride, aluminum chloride, zinc chloride, steel chloride,
This is a method for producing 3°5-diiodosalicylic acid, which is characterized by adding one or more compounds selected from sulfuric acid and phosphoric acid.
−ａに、塩素化、臭素化および沃素化で分子状の塩素、
臭素及び沃素を用いた場合に塩化アルミニウムや塩化鋼
等を添加する方法が、知られている。しかし、沃素化剤
として広く用いられている一塩化沃素は均一系の反応に
おいては触媒を必要としない場合が多い、不均一系では
純度的な問題を起こす場合があるが、これに応用された
例は報告されていない。-a, molecular chlorine by chlorination, bromination and iodination,
A method is known in which aluminum chloride, chlorinated steel, etc. are added when bromine and iodine are used. However, iodine monochloride, which is widely used as an iodizing agent, often does not require a catalyst in homogeneous reactions, and may cause purity problems in heterogeneous reactions; No cases have been reported.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明に用いられる化合物は塩化第二鉄、塩化アルミニ
ウム、塩化鋼、塩化亜鉛、硫酸、リン酸等であり、水和
物もしくは水溶液でも使うことができる。これらの化合
物は１種類添加すれば充分であるが２種以上混合して添
加しても差し支えない、添加量としてはサリチル酸に対
して０．１〜２０モル、特に１〜１０モルが望ましい、
２０モルを戦火ては効果に差がなく、０．１モル未満で
は触媒添加効果が低い、触媒の添加は反応開始前に行な
うことが望ましいが、−塩化沃素の添加中に行なっても
差し支えなく、また、−塩化沃素の添加後に行なっても
反応時間が若干長くなる程度で差し支えない。The compounds used in the present invention include ferric chloride, aluminum chloride, steel chloride, zinc chloride, sulfuric acid, phosphoric acid, etc., and can also be used in hydrate form or aqueous solution. It is sufficient to add one type of these compounds, but it is also possible to add a mixture of two or more types, and the amount added is preferably 0.1 to 20 mol, particularly 1 to 10 mol, based on salicylic acid.
If the amount is 20 mol, there is no difference in the effect, and if it is less than 0.1 mol, the effect of adding the catalyst is low.It is preferable to add the catalyst before the start of the reaction, but it may be done during the addition of iodine chloride. Furthermore, even if the reaction is carried out after the addition of -iodine chloride, the reaction time may be slightly longer.
本発明により、３．５−ジヨードサリチル酸を製造する
場合の初期のサリチル酸の濃度は１．０〜１５重量％が
望ましく、さらに好ましくは２．０〜１０重１％である
。１５重量％越える濃度になると反応中に析出してくる
３、５−ジヨードサリチル酸の結晶のために撹拌効率が
低下し反応性が悪くなり、上記化合物の添加効果がみら
れない、また、１．０重量％未満では製造効率が低下し
、経済的に好ましくない。According to the present invention, when producing 3.5-diiodosalicylic acid, the initial concentration of salicylic acid is preferably 1.0 to 15% by weight, more preferably 2.0 to 10% by weight. When the concentration exceeds 15% by weight, crystals of 3,5-diiodosalicylic acid precipitate during the reaction, resulting in lower stirring efficiency and poor reactivity, and no effect of the addition of the above compound is observed. If it is less than 0.0% by weight, manufacturing efficiency decreases, which is economically unfavorable.
反応に用いる一塩化沃素は、サリチル酸１モルに対して
２．０〜２．６モルが望ましく、好ましくは２．０〜２
．４モルである。２．０モル未満では充分に反応が進ま
ず、未反応のモノヨードサリチル酸により、得られた３
、５−ジヨードサリチル酸の品質低下を起こすため好ま
しくない、また、２．６モルを越えると収率および結晶
品質の向上はみられない。The amount of iodine monochloride used in the reaction is desirably 2.0 to 2.6 mol, preferably 2.0 to 2 mol, per 1 mol of salicylic acid.
．． It is 4 moles. If the amount is less than 2.0 mol, the reaction will not proceed sufficiently, and the unreacted monoiodosalicylic acid will cause the resulting 3
, 5-diiodosalicylic acid, which is undesirable because it causes a deterioration in quality, and if it exceeds 2.6 mol, no improvement in yield or crystal quality is observed.
−塩化沃素を添加する場合の溶媒は、塩化ナトリウム、
塩化カリウム及び塩酸等の水冷液を用いるが、無溶媒で
添加することもできる。−塩化沃素の添加時間は一括添
加〜３．０時間が望ましく、好ましくは０．２５〜１．
５時間である。これ以上長い時間で添加しても反応時間
が長くなるだけで好ましいとは言えない０反応温度は５
０〜１００″Ｃが好ましいが、加圧で反応する場合には
１００°Ｃ以上の温度で行なうこともできる。５０’Ｃ
以下の温度でも反応は進行するが反応時間が長くなるた
め好ましくはない０反応時間は、反応温度により異なる
が、大体１〜５時間である。- When adding iodine chloride, the solvent is sodium chloride,
Water-cooled liquids such as potassium chloride and hydrochloric acid are used, but they can also be added without solvent. - The addition time of iodine chloride is preferably from batch addition to 3.0 hours, preferably from 0.25 to 1.0 hours.
It is 5 hours. If it is added for a longer time than this, the reaction time will only become longer and it cannot be said to be preferable.The reaction temperature is 5.
The temperature is preferably 0 to 100"C, but when the reaction is carried out under pressure, it can also be carried out at a temperature of 100"C or higher. 50"C
Although the reaction proceeds even at the following temperatures, the reaction time becomes longer, which is not preferable. The zero reaction time varies depending on the reaction temperature, but is approximately 1 to 5 hours.
本発明による３、５−ジヨードサリチル酸の製造方法は
溶媒を用いることがないために、廃液中に残存している
沃素を有ａ溶媒の除去等の操作を行なう事なく、還元剤
添加程度でイオン交換樹脂等で容易に回収することがで
きる。Since the method for producing 3,5-diiodosalicylic acid according to the present invention does not use a solvent, the iodine remaining in the waste liquid can be removed by adding a reducing agent without performing operations such as removing the a-containing solvent. It can be easily recovered using ion exchange resin or the like.
［実施例］ 以下本発明を実施例により具体的に説明する。[Example] The present invention will be specifically explained below using examples.
分析は全て液体クロマトグラフィーによる。All analyzes were performed by liquid chromatography.
実施例１
撹拌機付き５００■１四つロフラスコに水３０ｂ、サリ
チル酸１３．８ｇ（０，１モル）及び塩化アルミニウム
六水和物０．４８ｇ（０，００２モル）を入れ、７０°
Ｃに昇温し、５０重量％−塩化沃素塩酸水溶液７１．５
ｇ（０，２２モル）を１時間かけて導入した。さらに、
２時間、同温度で反応させた。これを３０°Ｃまで冷却
し、析出している結晶を濾過し、乾燥したところ、３，
５シヨートサリチル酸の結晶３７．５ｇ （収率９６
．２χ）を得た。結晶の分析を行なったところモノヨー
ドサリチル酸の含有率は２．４１！ｌｉＨであった。Example 1 30 b of water, 13.8 g (0.1 mol) of salicylic acid, and 0.48 g (0,002 mol) of aluminum chloride hexahydrate were placed in a 500 x 1 four-loaf flask equipped with a stirrer, and heated at 70°.
C. and 50% by weight aqueous iodine chloride hydrochloric acid solution 71.5
g (0.22 mol) were introduced over the course of 1 hour. moreover,
The reaction was continued at the same temperature for 2 hours. When this was cooled to 30°C, the precipitated crystals were filtered and dried, 3.
37.5 g of crystals of 5-syotosalicylic acid (yield: 96
．． 2χ) was obtained. When the crystals were analyzed, the content of monoiodosalicylic acid was 2.41! It was liH.
実施例２
塩化アルミニウム六水和物の代わりに塩化第二鉄を０．
３３ｇ（０，００２モル）用いた以外は実施例１と同様
に行なった。その結果、３．５−ジヨードサリチル酸の
結晶３７．３ｇ（収率９５．６χ）を得た。モノヨード
サリチル酸の含有率は２．３１重量％であった。Example 2 Ferric chloride was added in place of aluminum chloride hexahydrate.
The same procedure as in Example 1 was conducted except that 33 g (0,002 mol) was used. As a result, 37.3 g of crystals of 3.5-diiodosalicylic acid (yield: 95.6χ) were obtained. The content of monoiodosalicylic acid was 2.31% by weight.
実施例３
塩化アルミニウム穴水和物の代わりに塩化亜鉛を０．２
７ｇ（０，００２モル）用いた以外は実施例１と同様に
行なった。その結果、３，５−ジヨードサリチル酸の結
晶３７．５ｇ（収率９６．１χ）を得た。モノヨードサ
リチル酸の含有率は２．４８重量％であった。Example 3 0.2% zinc chloride instead of aluminum chloride hydrate
The same procedure as in Example 1 was carried out except that 7 g (0,002 mol) was used. As a result, 37.5 g of crystals of 3,5-diiodosalicylic acid (yield: 96.1χ) were obtained. The content of monoiodosalicylic acid was 2.48% by weight.
実施例４
塩化アルミニウム六水和物の代わりに塩化第二洞二水和
物０．３４ｇ（０，００２モル）用いた以外は実施例１
と同様に行なった。その結果、３．５−ジヨードサリチ
ル酸の結晶３７．０ｇ（収率９４．９χ）を得た。モノ
ヨードサリチル酸の含有率は３．０３重量％であった。Example 4 Example 1 except that 0.34 g (0,002 mol) of dihydrochloride dihydrate was used instead of aluminum chloride hexahydrate.
I did the same thing. As a result, 37.0 g of crystals of 3.5-diiodosalicylic acid (yield: 94.9χ) were obtained. The content of monoiodosalicylic acid was 3.03% by weight.
実施例５
塩化アルミニウム六水和物の代わりに硫酸を０゜４９ｇ
（０，００５モル）用いた以外は実施例１と同様に行な
った。その結果、３．５−ジヨードサリチル酸の結晶３
８．１ｇ（収率９７．６χ）を得た。モノヨードサリチ
ル酸の含有率は１．３６重量％であった。Example 5 0°49g of sulfuric acid instead of aluminum chloride hexahydrate
The same procedure as in Example 1 was conducted except that (0,005 mol) was used. As a result, crystal 3 of 3,5-diiodosalicylic acid was obtained.
8.1 g (yield 97.6x) was obtained. The content of monoiodosalicylic acid was 1.36% by weight.
比較例１
塩化アルミニウム六水和物を用いなかった以外は実施例
１と同様に行なった。その結果、３．５−ジヨードサリ
チル酸の結晶３５．２ｇ（収率９０．３χ）を得た。Comparative Example 1 The same procedure as Example 1 was carried out except that aluminum chloride hexahydrate was not used. As a result, 35.2 g of crystals of 3.5-diiodosalicylic acid (yield: 90.3χ) were obtained.
モノヨードサリチル酸の含有率は１０．６５重量％であ
った。The content of monoiodosalicylic acid was 10.65% by weight.
［発明の効果］
本発明によれば、有機溶媒を用いる事なく水中で高収率
かつ高純度の３．５−ジヨードサリチル酸を得ることが
でき、廃液からの沃素回収も溶媒除去等の操作を行なう
事なく容品にできるため、３，５シヨートサリチル酸の
有用な製造法である。[Effects of the Invention] According to the present invention, high yield and high purity 3,5-diiodosalicylic acid can be obtained in water without using an organic solvent, and iodine recovery from waste liquid can be performed by operations such as solvent removal. This is a useful method for producing 3,5-syotosalicylic acid because it can be made into a package without any further steps.
Claims (1)
ジヨードサリチル酸を製造する方法において、塩化第二
鉄、塩化アルミニウム、塩化亜鉛、塩化鋼、硫酸及びリ
ン酸のうち選ばれた１種類以上の化合物を添加すること
を特徴とする３，５−ジヨードサリチル酸の製造方法。3,5-
A method for producing diiodosalicylic acid, characterized in that one or more compounds selected from ferric chloride, aluminum chloride, zinc chloride, steel chloride, sulfuric acid and phosphoric acid are added. Method for producing iodosalicylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1306400A JP2677687B2 (en) | 1989-11-28 | 1989-11-28 | Method for producing 3,5-diiodosalicylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1306400A JP2677687B2 (en) | 1989-11-28 | 1989-11-28 | Method for producing 3,5-diiodosalicylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03167153A true JPH03167153A (en) | 1991-07-19 |
| JP2677687B2 JP2677687B2 (en) | 1997-11-17 |
Family
ID=17956561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1306400A Expired - Fee Related JP2677687B2 (en) | 1989-11-28 | 1989-11-28 | Method for producing 3,5-diiodosalicylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2677687B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995035122A1 (en) * | 1994-06-21 | 1995-12-28 | Mallinckrodt Medical, Inc. | Improved synthesis of ioversol using phosphoric acid modified co-addition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108033429A (en) * | 2017-11-17 | 2018-05-15 | 贵阳开磷化肥有限公司 | A kind of method that iodine deep purifying is recycled in phosphoric acid by wet process and fluosilicic acid |
-
1989
- 1989-11-28 JP JP1306400A patent/JP2677687B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995035122A1 (en) * | 1994-06-21 | 1995-12-28 | Mallinckrodt Medical, Inc. | Improved synthesis of ioversol using phosphoric acid modified co-addition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2677687B2 (en) | 1997-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1777215B1 (en) | Method for producing 2-amino-5-iodobenzoic acid | |
| KR100269079B1 (en) | Process for the preparation of a halosubstituted aromatic acid | |
| JPH05500812A (en) | Continuous production method of 3,3'-dichloro-benzidine-dihydrochloride | |
| US3215736A (en) | Preparation of amino acids | |
| JPH03167153A (en) | Production of 3,5-diiodosalicylic acid | |
| JP3011493B2 (en) | Method for producing 4-alkyl-3-thiosemicarbazide | |
| JP5652008B2 (en) | Method for producing o-tolidine sulfone | |
| JPH0564940B2 (en) | ||
| JP3938222B2 (en) | Process for producing diiodomethyl-p-tolylsulfone | |
| JPS5917104B2 (en) | Method for producing hydroxyphenylglycine compounds | |
| JPS5951234A (en) | Preparation of 2-acetyl-6-methoxynaphthalene | |
| JP2541882B2 (en) | Method for producing anthranilic acids | |
| JP3042122B2 (en) | Method for producing N-cyanoacetamidine derivative | |
| JPH0478638B2 (en) | ||
| JP4493805B2 (en) | Method for producing high-purity benzoic acid derivative | |
| JPS60218383A (en) | Manufacture of 4-halogen-naphthalic acid anhydride | |
| JPH11140045A (en) | Production of thiosalicylic acid | |
| EP0416602A2 (en) | Bis(4-halo-phthalic acid)quarter salts, process for their preparation and their use | |
| JPH10218832A (en) | Purification of acrylic acid | |
| JPH03284648A (en) | Method for industrially producing naphthalene-2,6-dicarboxylic acid | |
| JPS62164660A (en) | Production of methyl 2-sulfamidobenzoate | |
| JPH08165279A (en) | Production of 5-hydroxyisoquinoline | |
| JPH08157444A (en) | Production of aminoethanesulfonic acid | |
| JPH0662498B2 (en) | Method for producing 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid | |
| JPH05320093A (en) | Production of biphenyldicarboxylic acid dichloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |