JPS63206489A - Production of m-hydroxybenzyl alcohol by electrolysis - Google Patents
Production of m-hydroxybenzyl alcohol by electrolysisInfo
- Publication number
- JPS63206489A JPS63206489A JP62039130A JP3913087A JPS63206489A JP S63206489 A JPS63206489 A JP S63206489A JP 62039130 A JP62039130 A JP 62039130A JP 3913087 A JP3913087 A JP 3913087A JP S63206489 A JPS63206489 A JP S63206489A
- Authority
- JP
- Japan
- Prior art keywords
- hydrochloric acid
- cathode
- anode
- soln
- acidic
- 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
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000005868 electrolysis reaction Methods 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 9
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003792 electrolyte Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 description 13
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000003014 ion exchange membrane Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001023 sodium amalgam Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- LLTOPKQGFAAMKH-UHFFFAOYSA-N siderin Chemical compound COC1=CC(=O)OC2=CC(OC)=CC(C)=C21 LLTOPKQGFAAMKH-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Description
【発明の詳細な説明】
童呈上夙机■分立
本発明は、ｍ−ヒドロキシベンジルアルコール（以下ｍ
−Ｈ８０Ｈと略記する）の製造方法に関するものである
。[Detailed description of the invention] The present invention provides m-hydroxybenzyl alcohol (hereinafter m-hydroxybenzyl alcohol).
-H80H).
ｍ−１１８（ＩＮは工薬、あるいはａｍの中間体として
任用な化合物であるが、現状ではこれの安価な製造方法
による工業的供給には至っていない。m-118 (IN is a compound that is used as a chemical agent or an intermediate for am, but at present it has not been industrially supplied by an inexpensive manufacturing method.
丈米ｐ用玉
５−ＩＩＢＯＨの合成法として、ｍ−クレゾールを原料
とする発酵法、ｍ−ヒドロキシベンズアルデヒドを原料
とするナトリウム・アマルガム、＃ａ８Ｌ、ＬｉＡ Ｉ
Ｈａ等による還元及び水素添加反応等があるが、収率
的に不十分であったりして、実用化には至っていない、
また水素添加反応は高温、高圧下の反応であり工業的製
法には種々問題がある。As a synthesis method of Tama5-IIBOH for long rice p, fermentation method using m-cresol as raw material, sodium amalgam using m-hydroxybenzaldehyde as raw material, #a8L, LiA I
There are reduction and hydrogenation reactions using Ha, etc., but they have not been put into practical use due to insufficient yields.
Furthermore, the hydrogenation reaction is a reaction at high temperature and high pressure, and there are various problems with industrial production methods.
また、トヒドロキシ安息香酸（以下、ａ＋−１１８Ａと
略記する）を原料とする方法については、ナトリウム・
アマルガム及び電解還元法が提案（Ｂｅｒｉｃｔ＋ｔｅ
３８１７５２（１９０５））されているが収率的にも
低く工業的方法にはなり得なかった。In addition, regarding the method using hydroxybenzoic acid (hereinafter abbreviated as a+-118A) as a raw material, sodium
Amalgam and electrolytic reduction method proposed (Beric+te
381752 (1905)), but the yield was low and it could not be used as an industrial method.
本発明者らは、先にａ＋−１１８０８の製造方法につい
て検討し、５−ＩＩＢＡの電解還元を水溶液、あるいは
水可溶性有機溶媒中で行う方法、更に陰極液中に支持電
解質を添加する方法で高収率でｍ−８８０１１をうる方
法も既に見出している。（特開昭６０−２３４９８７、
Ｕが”ンしようとする間 Ｉさ
本発明者らは、更にｏ＋−８８０１１の工業的製法につ
いて、鋭意検討を行い、ｍＪＩ８Ａを酸性水溶液中で電
解還元を行い高収率で高純度の−１１８０８を得る方法
を先に提案した（特願昭６０−２６３８５８ 、特願昭
６０−２７２４６７ ）。The present inventors have previously investigated the production method of a+-11808, and found that the electrolytic reduction of 5-IIBA is carried out in an aqueous solution or a water-soluble organic solvent, and that a supporting electrolyte is added to the catholyte. A method for obtaining m-88011 in high yield has already been found. (Unexamined Japanese Patent Publication No. 60-234987,
The present inventors further conducted intensive studies on the industrial production method of o+-88011, and conducted electrolytic reduction of mJI8A in an acidic aqueous solution to produce -11808 with high yield and high purity. We have previously proposed a method for obtaining (Japanese Patent Applications No. 60-263858 and No. 60-272467).
本電解反応は通常、陽陰極を分離した電解槽を用い、陰
極側で反応を行う。しかし反応中、陽極側は水の電気分
解による酸素発生が起こるのみで有効に利用されていな
い。すなわち、本電解還元反応をより効果的に実施する
ためには、陽極側を有効に利用することが重要である。This electrolytic reaction usually uses an electrolytic cell with separate anodes and cathodes, and the reaction is carried out on the cathode side. However, during the reaction, the anode side is not used effectively, as oxygen is only generated by electrolysis of water. That is, in order to carry out the present electrolytic reduction reaction more effectively, it is important to effectively utilize the anode side.
本発明の課題は、陽陰極を分離した陰極側で−ＨＢＡの
還元反応を行うと同時に、陽極側で起こる酸化反応を利
用して、陽極でも付加価値のある製品を生産する方法を
提供することである。An object of the present invention is to provide a method for producing value-added products at the anode by performing a -HBA reduction reaction on the cathode side separated from the anode and at the same time utilizing an oxidation reaction occurring on the anode side. It is.
ｒｏ 占をｌｌするだめの
本発明者らは、上記課題を解決するために鋭意検討を行
い、塩酸水溶液を陽極液に用いることで陽極側で塩酸の
酸化が効率よく起こり、塩素が製造できることを見出し
、本発明を完成させた。In order to solve the above problem, the inventors of the present invention, who have no choice but to solve the above problem, conducted intensive studies and found that by using an aqueous solution of hydrochloric acid as the anolyte, the oxidation of hydrochloric acid occurs efficiently on the anode side, and chlorine can be produced. The present invention has been completed.
即ち、本発明はトヒドロキシ安息香酸を陽、陰極を分離
した電解槽を用いて、陰極室で酸性水溶液中２０〜７０
゛Ｃで電解還元するに際し陽極液には塩酸水溶液を用い
、陰極還元と同時に陽極室では塩素を製造することを特
徴とするｍ−ヒドロキシヘンシルアルコールの電解によ
る製造法である。That is, the present invention uses an electrolytic cell with separated anode and cathode for tohydroxybenzoic acid, and injects 20 to 70 g
This is a method for producing m-hydroxyhensyl alcohol by electrolysis, which is characterized in that an aqueous hydrochloric acid solution is used as the anolyte during electrolytic reduction at C, and chlorine is produced in the anode chamber at the same time as the cathode reduction.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明において、陰極液に用いる酸性水溶液としては、
陰極での電解反応に不活性な酸性物質であれば、特に限
定するものではないが、コスト的に通常鉱酸を用いるの
が望ましく、特に材質及び収率の点から硫酸、あるいは
塩酸が好ましい鉱酸であり、通常１〜３０重量％の水溶
液が用いられる。In the present invention, the acidic aqueous solution used for the catholyte is
Although there are no particular limitations on acidic substances as long as they are inert to the electrolytic reaction at the cathode, it is usually desirable to use mineral acids in terms of cost, and in particular sulfuric acid or hydrochloric acid is preferred in terms of material quality and yield. It is an acid, and an aqueous solution of 1 to 30% by weight is usually used.
陽極に塩酸を用いる場合は塩酸水の塩酸濃度は任意であ
るが酸化反応を電流効率良く行うために３〜３０重量％
、好ましくは５〜２５重世％の範囲で行うのが良い。When using hydrochloric acid for the anode, the concentration of hydrochloric acid in the hydrochloric acid water is arbitrary, but it is 3 to 30% by weight in order to carry out the oxidation reaction with high current efficiency.
, preferably in the range of 5-25%.
また塩素発生にともない、塩酸濃度が低下するため、上
記塩酸濃度を保つために、反応中適時濃塩酸水、あるい
は塩酸ガスを陽極中に加えても良い。Further, as the hydrochloric acid concentration decreases as chlorine is generated, concentrated hydrochloric acid water or hydrochloric acid gas may be added to the anode at appropriate times during the reaction in order to maintain the above-mentioned hydrochloric acid concentration.
ｍ−ヒドロキシ安息香酸の酸性水溶液中の濃度は通常５
〜２０重量％である。The concentration of m-hydroxybenzoic acid in acidic aqueous solution is usually 5
~20% by weight.
本発明方法において、電解還元反応は２０〜７０℃の温
度範囲で実施する。又、電解に用いる電極のうち特に陰
極材料は水素過電圧の高いもの、具体的には亜鉛、鉛、
カドミウム、水銀を用いる。対する陽極については、通
常の電極材料であれば特に限定しない。In the method of the present invention, the electrolytic reduction reaction is carried out at a temperature range of 20 to 70°C. In addition, among the electrodes used for electrolysis, the cathode material is one with a high hydrogen overvoltage, specifically zinc, lead,
Uses cadmium and mercury. The anode, on the other hand, is not particularly limited as long as it is made of a normal electrode material.
電解槽はイオン交換隔膜により、陽極室、陰極室を隔離
することが必要である。その他の隔ｎｇ！の材質として
は、アスベスト、セラミックス、シンタードグラス等も
使用できる。The electrolytic cell requires an ion exchange membrane to separate the anode chamber and cathode chamber. Other gaps! As the material, asbestos, ceramics, sintered glass, etc. can also be used.
本発明の電解還元において、電流密度は好ましくは５〜
３０Ａ／ｄ ｒｒｌである。理論的には４電子還元であ
り、４ Ｆｒ／ｍｏｌｅ通電世である通電流効率は５０
〜７０％である為、反応を完結させるには５〜８Ｐｒ／
ｍｏｌｅ電気量を通す必要がある。In the electrolytic reduction of the present invention, the current density is preferably 5 to
30A/drrl. Theoretically, it is a 4-electron reduction, and the current efficiency at 4 Fr/mole current flow is 50
~70%, so to complete the reaction 5~8Pr/
It is necessary to pass mole electricity.
務■反グ四果
本発明方法は陽陰極を分離した電解槽を用いて、陰極側
でｍ４１８Ａを酸性液中電解還元反応を行うと同時に陽
極液には、塩酸水を用い塩酸を電解酸化し、塩素を製造
することにより、従来、陽極側では無駄に使われていた
電気を有効に利用できるようになり、工業的に極めて価
値ある発明であるる。The method of the present invention uses an electrolytic cell with separate anodes and cathodes, and performs an electrolytic reduction reaction of m418A in an acidic solution on the cathode side, and at the same time electrolytically oxidizes the hydrochloric acid using hydrochloric acid water as the anolyte. By producing chlorine, it is now possible to effectively utilize electricity that was previously wasted on the anode side, making it an extremely valuable invention from an industrial perspective.
実施例１
両極室とも３００−の容量を有し、隔膜としてセレミオ
ンＣＭＶ （旭硝子（株）の商品名のイオン交換膜）
で隔離されたト■型の電解セルを使用して、陰極室に１
０％硫酸水、陽極室に２０％の塩酸水をそれぞれ２００
ｔｔｄｌづつ仕込む。陰極として５０ｃｆｆｌの鉛板
、陽極として５０ｃｄの・白金板を用いた。さらに陽極
側は発生する塩素ガスが逃げないようにフタをし、ガラ
ス配管を設けて０．２Ｎヨウ化カリ水？ｆＩ液の１−ラ
ップをつけた。Example 1 Both electrode chambers had a capacity of 300-, and the diaphragm was Selemion CMV (ion exchange membrane under the trade name of Asahi Glass Co., Ltd.).
Using a T-type electrolytic cell isolated with
0% sulfuric acid water and 20% hydrochloric acid water in the anode chamber, respectively.
Prepare ttdl one by one. A 50 cffl lead plate was used as the cathode, and a 50 cd platinum plate was used as the anode. Furthermore, the anode side is covered with a lid to prevent the generated chlorine gas from escaping, and a glass pipe is installed to prepare 0.2N potassium iodide water. A 1-wrap of fI solution was applied.
電解セルを５０″Ｃに保ちつつ、６Ａの直流定電流を通
電しつつ、５−ＮＢＡ ２５ｇをマイクロフィーダーを
用いて６ｇ／時間の割合で陰極液中に添加し、４，２時
間でｓ＋−ＩＩＢＡを全量添加した。この後更に電解を
０．８時間継続した（６．２Ｆｒ／ｓ＋ｏｌｅ） 、電
解終了後陰極液は抜取った後、エーテル抽出し、エーテ
ルを留出し、２１．８ ｇの結晶を得た。鋼−１１８０
１１の純度９８％、単離収率９５％であった。さらに陽
極側の塩素をトラップしたヨウ化カリ水溶液のヨウ素を
チオ硫酸ナトリウムで滴定した結果、陽極側からの塩素
の発生量３６．８ｇ 、酸化反応の電流効率９０％であ
った。While maintaining the electrolytic cell at 50"C and applying a constant DC current of 6A, 25g of 5-NBA was added to the catholyte at a rate of 6g/hour using a microfeeder, and s+- The entire amount of IIBA was added. After this, electrolysis was further continued for 0.8 hours (6.2 Fr/s + ole). After the electrolysis was completed, the catholyte was drained, extracted with ether, and the ether was distilled off. Crystals were obtained. Steel-1180
The purity of 11 was 98%, and the isolation yield was 95%. Further, the iodine in the potassium iodide aqueous solution that had trapped chlorine on the anode side was titrated with sodium thiosulfate, and the result was that the amount of chlorine generated from the anode side was 36.8 g, and the current efficiency of the oxidation reaction was 90%.
実施例２
陽陰極液とも１０％の塩酸水を仕込、陽極液中には塩酸
ガスを１時間ごとに０．２５モルづつ添加（０゜２５モ
ル×４回、合計１モル）した以外は実施例１と同様の反
応を行った。 ｍ−ＨＢＯＨの単離収率９４％、塩素発
生量３９．３ｇ 、酸化反応の電流効率９６％であった
。Example 2 10% hydrochloric acid water was added to both the anode and catholyte solutions, and 0.25 mol of hydrochloric acid gas was added to the anolyte every hour (0°25 mol x 4 times, total 1 mol). A reaction similar to Example 1 was carried out. The isolated yield of m-HBOH was 94%, the amount of chlorine generated was 39.3 g, and the current efficiency of the oxidation reaction was 96%.
光肌見処果
実施例の結果から明らかな通り、ｓ−）ＩＢＭの電解還
元によるａ＋−）１８０Ｈの製造において、陽極液とじ
て塩酸水を用いると、電流効率良く塩素ガスが得られ、
陽極側が有効に利用できるようになった。As is clear from the results of the Examples, when hydrochloric acid water is used as the anolyte in the production of s-) IBM's a+-) 180H by electrolytic reduction, chlorine gas can be obtained with high current efficiency.
The anode side can now be used effectively.
Claims (1)
を用い陰極室で酸性水溶液中２０〜７０℃で電解還元す
るに際し、陽極液には塩酸水溶液を用い、陰極還元と同
時に陽極室では塩素を製造することを特徴とするｍ−ヒ
ドロキシベンジルアルコールの電解による製造法。When m-hydroxybenzoic acid is electrolytically reduced at 20 to 70°C in an acidic aqueous solution in the cathode chamber using an electrolytic cell with separate anode and cathode chambers, a hydrochloric acid aqueous solution is used as the anolyte, and chlorine is added in the anode chamber at the same time as the cathode reduction. A method for producing m-hydroxybenzyl alcohol by electrolysis, the method comprising: producing m-hydroxybenzyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62039130A JPS63206489A (en) | 1987-02-24 | 1987-02-24 | Production of m-hydroxybenzyl alcohol by electrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62039130A JPS63206489A (en) | 1987-02-24 | 1987-02-24 | Production of m-hydroxybenzyl alcohol by electrolysis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63206489A true JPS63206489A (en) | 1988-08-25 |
Family
ID=12544519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62039130A Pending JPS63206489A (en) | 1987-02-24 | 1987-02-24 | Production of m-hydroxybenzyl alcohol by electrolysis |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63206489A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855577A (en) * | 1981-09-25 | 1983-04-01 | Yuasa Battery Co Ltd | Preparation of amino acid |
| JPS60243293A (en) * | 1984-05-16 | 1985-12-03 | Mitsui Toatsu Chem Inc | Manufacture of m-hydroxybenzyl alcohol |
-
1987
- 1987-02-24 JP JP62039130A patent/JPS63206489A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855577A (en) * | 1981-09-25 | 1983-04-01 | Yuasa Battery Co Ltd | Preparation of amino acid |
| JPS60243293A (en) * | 1984-05-16 | 1985-12-03 | Mitsui Toatsu Chem Inc | Manufacture of m-hydroxybenzyl alcohol |
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