JPS61171452A - Production method of metabromobenzoic acid - Google Patents
Production method of metabromobenzoic acidInfo
- Publication number
- JPS61171452A JPS61171452A JP60012193A JP1219385A JPS61171452A JP S61171452 A JPS61171452 A JP S61171452A JP 60012193 A JP60012193 A JP 60012193A JP 1219385 A JP1219385 A JP 1219385A JP S61171452 A JPS61171452 A JP S61171452A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- sulfuric acid
- hydrogen peroxide
- reaction
- metabromobenzoic
- 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 6
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 title claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 36
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 32
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 15
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 27
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052742 iron Inorganic materials 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 239000011701 zinc Substances 0.000 abstract description 2
- 229910052725 zinc Inorganic materials 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- -1 iron or zinc Chemical compound 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000283986 Lepus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004972 metal peroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
【発明の詳細な説明】
（技術分野）
本発明はメタブロモ安息香１！ｉ！（以下、ＭＢＢＡと
言う）の製法に関するものである。[Detailed Description of the Invention] (Technical Field) The present invention provides metabromobenzoin 1! i! (hereinafter referred to as MBBA).
（従来の技術と発明が解決しようとする問題点）ＭＢＢ
Ａは例えば、ピレスロイド系農薬の中間体として有用な
ものであシ、従来、安息香酸を触媒の存在下、硫酸中で
分子状臭素と反応させることによ〕製造する方法が知ら
れている。(Problems to be solved by conventional technology and invention) MBB
A is useful, for example, as an intermediate for pyrethroid pesticides, and it has been conventionally produced by reacting benzoic acid with molecular bromine in sulfuric acid in the presence of a catalyst.
ところが、この反応においては分子状臭素の利用率が低
いため安息香酸の転換率が低く、また、ＭＢＢＡの選択
率も高いものとは言えなかった。However, in this reaction, the conversion rate of benzoic acid was low due to the low utilization rate of molecular bromine, and the selectivity of MBBA could not be said to be high.
そこで、この欠点を改良し高収率でＭＢＢＡを得るため
の方法として、例えば、硝酸及び塩酸を混合した硫酸溶
媒中でブーム化反応を実施する方法（特開昭！ぶ−３０
．り４ｔ７号）が提案されている。また、一般的に芳香
族化合物をブロム化する際にプロふ化剤の利用効率を高
める方法として、反応系に分子状塩素を供給しながら反
応を行なう方法も知られている。しかしながら、前者の
方法では反応系が腐食性の強い混酸系となるため、特に
、工業的には反応混合物の処理が面倒となる欠点があシ
、また、後者の方法でも塩酸が副生ずるばかシか、目的
生成物の収率面から安息香酸を硫酸中でブロム化する場
合には不十分な方法であった。Therefore, as a method to improve this drawback and obtain MBBA in a high yield, for example, a method of carrying out a booming reaction in a sulfuric acid solvent containing a mixture of nitric acid and hydrochloric acid (Japanese Patent Application Laid-Open No. 2002-120002)
．． 4t No. 7) has been proposed. Furthermore, as a method of generally increasing the utilization efficiency of a profurating agent when brominating an aromatic compound, a method of carrying out the reaction while supplying molecular chlorine to the reaction system is also known. However, in the former method, the reaction system becomes a highly corrosive mixed acid system, which has the drawback that the treatment of the reaction mixture is troublesome, especially in industrial applications.Also, even in the latter method, hydrochloric acid is produced as a by-product. However, in view of the yield of the desired product, this method was insufficient when brominating benzoic acid in sulfuric acid.
（問題点を解決するための手段）
すなわち、本発明は、安息香酸を触媒の存在下、硫酸又
は発ａ硫酸中で分子状臭素と反応させＭＢＢＡ′ｆｌ：
ｆｉ造するに際し、反応系に過酸化水素を存在させるこ
とを特徴とするＭｇ３ムの製法を要旨とする。(Means for Solving the Problems) That is, the present invention involves reacting benzoic acid with molecular bromine in sulfuric acid or aqueous sulfuric acid in the presence of a catalyst to produce MBBA'fl:
The gist of this invention is a method for producing Mg3, which is characterized by the presence of hydrogen peroxide in the reaction system when producing fi.
本発明は、安息香酸と分子状臭素とを触媒の存在下、硫
酸又は発煙硫酸中で反応させるものであるが、分子状臭
素の使用量は通常、安息香酸に対して、０．７〜１モル
倍、好ましくはＯ０！〜０．７モル倍である。In the present invention, benzoic acid and molecular bromine are reacted in sulfuric acid or fuming sulfuric acid in the presence of a catalyst, and the amount of molecular bromine used is usually 0.7 to 1% per benzoic acid. Mol times, preferably O0! ~0.7 mole times.
本発明で溶媒として用いる硫酸又は発煙硫酸は通常、硫
酸の場合には、１０〜ｉｏｏ重量％、また、発煙硫酸の
場合には、８０８濃度が／ −２０重量％のものが使用
される。硫酸を用いる場合忙、あまシ濃度が低いと常圧
下で原料の安息香酸を十分に溶解することができないの
で好ましくない。硫酸又は発煙硫酸の使用量は通常、安
息香酸に対して／〜１０重量倍である。The sulfuric acid or fuming sulfuric acid used as a solvent in the present invention is usually 10 to 100% by weight in the case of sulfuric acid, and one having an 808 concentration of /-20% by weight in the case of fuming sulfuric acid. When using sulfuric acid, it is not preferable to use sulfuric acid because if the concentration of sulfuric acid is low, the raw material benzoic acid cannot be sufficiently dissolved under normal pressure. The amount of sulfuric acid or fuming sulfuric acid used is usually 10 times the weight of benzoic acid.
触媒としては通常、ブロム化反応の触媒として公知のも
のが挙げられ、代表的には例えば、分子状ヨード、鉄又
は亜鉛の金属もしくはそのハロゲン化物などが挙げられ
る。これらの触媒の使用量は通常、安息香酸に対して、
０．０ ／〜ｏ、ｉモル倍、好ましくは０．０−〜０．
０！モル倍であシ、この使用量があまシ少ないとプロふ
化反応が良好に進行せず、逆にあまシ多くても効果に変
）はなく経済的でない。The catalyst usually includes those known as catalysts for bromination reactions, and typical examples include molecular iodine, metals such as iron or zinc, or halides thereof. The amount of these catalysts used is usually based on benzoic acid.
0.0/~o, i mole times, preferably 0.0-~0.
0! If the amount used is too small, the pro-hatching reaction will not proceed well, and on the other hand, even if it is too large, the effect will not change and it is not economical.
木兄ＢＡにおいては、反応系に過酸化水素を存在させる
ことを必須の要件とするものである。Kinoe BA requires the presence of hydrogen peroxide in the reaction system.
この過酸化水素の添加によ〕、分子状臭素の利 ）
周率が高まシ安息香酸の転換率が上昇すると共に、Ｍｇ
３ムの選択率も向上し、その結果、高収率でＭｇ３ムを
回収することができる。過酸化水素の使用量は分子状臭
素に対して通常、０．３〜３モル倍、好ましくけＯＪ
Ｎ２Ｊモル倍であ）、この使用量があまシ少ないと十分
忙期待する効果が得られず、逆に、６１り多くても著し
い効果の向上はないので経済的でない。過酸化水素は通
常、３〜７０１ｔＪ１％の水溶液として使用される。ま
た、本発明では例えば、過硫酸、ヨウ素酸、過ヨウ素酸
、塩素酸又はバリウム、錫、鉛もしくはナトリウムなど
の金属過酸化物等の反応系内で過酸化水素を容易に生成
する化合物を用いても差し支えない。本発明の添加剤の
反応系への供給は反応開始時に一括して加えてもよく、
また、反応途中に分割して加えてもよい。By adding this hydrogen peroxide, the benefit of molecular bromine is increased.
As the frequency increases and the conversion rate of cybenzoic acid increases, Mg
The selectivity of Mg3M is also improved, and as a result, Mg3M can be recovered with a high yield. The amount of hydrogen peroxide used is usually 0.3 to 3 times the molecular bromine, preferably OJ.
If the amount used is too small, the desired effect will not be obtained; on the other hand, even if it is more than 61, there will be no significant improvement in the effect, which is not economical. Hydrogen peroxide is typically used as a 3-701 tJ1% aqueous solution. Furthermore, in the present invention, compounds that easily generate hydrogen peroxide in the reaction system, such as persulfuric acid, iodic acid, periodic acid, chloric acid, or metal peroxides such as barium, tin, lead, or sodium, are used. There is no problem. The additives of the present invention may be supplied to the reaction system all at once at the start of the reaction.
Alternatively, it may be added in portions during the reaction.
本発明の反応温度は例えは、４ｔθ〜−００℃の温度で
実施できるが、一般的には常圧下で反応を行なうのが好
ましいので、通常、ご０〜１００℃の温度で実施される
。この温度があまシ低すぎると、ブロム化反応が良好に
進行せず、逆に、あｔｂ高すぎると、目的とするＭＢＢ
ム以外の例えば、オルトブロム体、パラブロム体、ジブ
ロム体などのプ筒ム化物の副生量が多くなるので好まし
くない。また、反応時間は通常、θ・！〜！時間程度で
ある。The reaction temperature of the present invention can be, for example, 4tθ to -00°C, but since it is generally preferable to carry out the reaction under normal pressure, the reaction is usually carried out at a temperature of 0 to 100°C. If this temperature is too low, the bromination reaction will not proceed well, and conversely, if the ATB is too high, the desired MBB
This is not preferable because it increases the amount of by-products other than hydrogen, such as orthobromine, parabromine, and dibromine. Also, the reaction time is usually θ・! ~! It takes about an hour.
本発明を実施するＫは通常、所定濃度の硫酸又は発煙硫
酸中忙安息香酸及び触媒を溶解又は懸濁させ、次いで、
反応系に分子状臭素と過酸化水素とをそれぞれ滴下しな
からプ党ム化反応を実施することができる。また、この
場合、分子状臭素又は過酸化水素の一部又は全部を予め
、反応系忙加えておいても差し支えない。In carrying out the present invention, normally the benzoic acid and catalyst are dissolved or suspended in sulfuric acid or oleum at a predetermined concentration, and then
The polymerization reaction can be carried out by dropping molecular bromine and hydrogen peroxide into the reaction system. In this case, part or all of molecular bromine or hydrogen peroxide may be added to the reaction system in advance.
反応後の混合物は通常、水を加えることｋよｆｉＭＢＢ
ムの結晶を析出させ、次すで、これをＦ遇するととＫよ
Ｊ）Ｍｇ３ムを回収することができる。そして、とのＭ
ｇ３ムの結晶は必要に応じて、洗浄した後、蒸留するこ
とｋよシ精製される。After the reaction, the mixture is usually mixed with water.
If crystals of Mg are precipitated and then treated with F, Mg3 can be recovered. And the M
If necessary, the g3m crystals are purified by washing and distillation.
（実施例）
以下、本発明を実施例によシ更に詳細に説明するが、本
発明は以下の実施例に＠定されるものではない。(Examples) Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples.
実施例７〜３
撹拌機及び温度調節器を備えたｊ００ｄガラヌ製反応器
に、安息香Ｈ２ｚ、ｏｔ（０，６７３モル）及び分子状
ヨード３．７１ ＃ （０，０／ｊモル）を溶解したり
Ｊ’ ｗｔチ硫酸／４ｔ０−を仕込み、撹拌下、４ｔＱ
℃の温度で分子状臭素ダタ、Ｊ Ｐ（ｏ、ｉｏｒモｈ’
）と第１表に示す割合の３！ｗｔ％過酸化水素水溶液と
をそれぞれ３時間かけて滴下し、更番Ｃ１その後３０分
間、撹拌を続はブロム化反応を行なった。Examples 7-3 In a j00d Galanu reactor equipped with a stirrer and a temperature controller, benzoin H2z,ot (0,673 mol) and molecular iodine 3.71 # (0,0/j mol) were dissolved. Add J' wt sulfuric acid/4t0-, and add 4tQ under stirring.
Molecular bromine data, J P (o, ior moh'
) and 3 of the proportions shown in Table 1! Wt% hydrogen peroxide aqueous solution was added dropwise over 3 hours, and the mixture was stirred for 30 minutes, followed by a bromination reaction.
反応終了後、混合物を高速液体クロマトグラフィーにて
分析し、安息香酸の転換率とＭＨＤムの選択率を求めた
ところ、第７表忙示す結果を得た。After the reaction was completed, the mixture was analyzed by high performance liquid chromatography to determine the conversion rate of benzoic acid and the selectivity of MHD, and the results shown in Table 7 were obtained.
比較例／
実施例／の方法において、過酸化水素水溶液の添加を省
略して実施例／と同様な反応を行なった場合の結果を第
７表に示す。Comparative Example/Example/The results are shown in Table 7 when the same reaction as in Example/ was carried out by omitting the addition of the hydrogen peroxide aqueous solution.
参考例
実施例／の方法において、過酸化水素水溶液の添加を省
略し、代シ忙、分子状塩素ガスを０、／ Ｊ ｆ ／
ｍｉｎの割合で供給（全供給量０．３０２モル）しなが
ら反応を行なった場合の結果を第７表忙示す。Reference Example In the method of Example /, the addition of the hydrogen peroxide aqueous solution was omitted, and the molecular chlorine gas was added to 0.
Table 7 shows the results when the reaction was carried out while feeding at a rate of min (total feed amount: 0.302 mol).
第１表
（発明の効果）
本発明によれば安息香酸を硫酸又は発煙硫酸中で分子状
臭素によジブロム化する際の転換率が向上するとともに
、目的とするＭＨＤ人の選択率も向上するので、高収率
でＭＨＤムを回収することができる。Table 1 (Effects of the Invention) According to the present invention, the conversion rate when benzoic acid is dibrominated with molecular bromine in sulfuric acid or oleum is improved, and the selectivity of the target MHD person is also improved. Therefore, MHDM can be recovered in high yield.
出 願 人 三菱化敢工業株式会社 代 理 人 弁理士 長谷用 − （はか７名）Sender: Mitsubishi Kagen Industries, Ltd. Representative Patent Attorney Hase - (7 people)
Claims (4)
分子状臭素と反応させメタブロモ安息香酸を製造するに
際し、反応系に過酸化水素を存在させることを特徴とす
るメタブロモ安息香酸の製法。(1) A method for producing metabromobenzoic acid, which is characterized in that hydrogen peroxide is present in the reaction system when producing metabromobenzoic acid by reacting benzoic acid with molecular bromine in sulfuric acid or oleum in the presence of a catalyst. .
〜３モル倍であることを特徴とする特許請求の範囲第（
１）項記載のメタブロモ安息香酸の製法。(2) The amount of hydrogen peroxide present is 0.3 relative to molecular bromine
Claim No. 3 (
1) The method for producing metabromobenzoic acid described in section 1).
請求の範囲第（１）項記載のメタブロモ安息香酸の製法
。(3) The method for producing metabromobenzoic acid according to claim (1), wherein the catalyst is molecular iodine.
る特許請求の範囲第（１）項記載のメタブロモ安息香酸
の製法。(4) The method for producing metabromobenzoic acid according to claim (1), wherein the reaction temperature is 60 to 100°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60012193A JPS61171452A (en) | 1985-01-25 | 1985-01-25 | Production method of metabromobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60012193A JPS61171452A (en) | 1985-01-25 | 1985-01-25 | Production method of metabromobenzoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61171452A true JPS61171452A (en) | 1986-08-02 |
| JPH0583533B2 JPH0583533B2 (en) | 1993-11-26 |
Family
ID=11798566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60012193A Granted JPS61171452A (en) | 1985-01-25 | 1985-01-25 | Production method of metabromobenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61171452A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0627405A1 (en) * | 1993-06-01 | 1994-12-07 | Hoechst Aktiengesellschaft | Process for the preparation of methyle 5-bromo-6-methoxy-1-naphthoate |
| WO2001094289A1 (en) * | 2000-06-05 | 2001-12-13 | Nissan Chemical Industries, Ltd. | Process for the preparation of bromoisophthalic acid compounds |
| JP2008069122A (en) * | 2006-09-15 | 2008-03-27 | Konica Minolta Holdings Inc | Manufacturing method of nitrogen-containing polycyclic heterocyclic compound |
| JP2021127332A (en) * | 2020-02-17 | 2021-09-02 | 株式会社トクヤマ | Method for Producing 5-Bromo-2-alkylbenzoic Acid |
-
1985
- 1985-01-25 JP JP60012193A patent/JPS61171452A/en active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0627405A1 (en) * | 1993-06-01 | 1994-12-07 | Hoechst Aktiengesellschaft | Process for the preparation of methyle 5-bromo-6-methoxy-1-naphthoate |
| US5412150A (en) * | 1993-06-01 | 1995-05-02 | Cassella Ag | Process for the preparation of methyl 5-bromo-6-methoxy-1-naphthoate |
| WO2001094289A1 (en) * | 2000-06-05 | 2001-12-13 | Nissan Chemical Industries, Ltd. | Process for the preparation of bromoisophthalic acid compounds |
| US6855845B2 (en) | 2000-06-05 | 2005-02-15 | Nissan Chemical Industries, Ltd. | Process for the preparing bromoisophithalic acid compound |
| KR100787277B1 (en) * | 2000-06-05 | 2007-12-20 | 닛산 가가쿠 고교 가부시키 가이샤 | Method for preparing 5-bromoisophthalic acid compound |
| JP2008069122A (en) * | 2006-09-15 | 2008-03-27 | Konica Minolta Holdings Inc | Manufacturing method of nitrogen-containing polycyclic heterocyclic compound |
| JP2021127332A (en) * | 2020-02-17 | 2021-09-02 | 株式会社トクヤマ | Method for Producing 5-Bromo-2-alkylbenzoic Acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0583533B2 (en) | 1993-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |