JPH0133099B2 - - Google Patents
Info
- Publication number
- JPH0133099B2 JPH0133099B2 JP56145230A JP14523081A JPH0133099B2 JP H0133099 B2 JPH0133099 B2 JP H0133099B2 JP 56145230 A JP56145230 A JP 56145230A JP 14523081 A JP14523081 A JP 14523081A JP H0133099 B2 JPH0133099 B2 JP H0133099B2
- Authority
- JP
- Japan
- Prior art keywords
- glyoxal
- acid
- glyoxylic acid
- aqueous
- glyoxylic
- 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
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 40
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 28
- 229940015043 glyoxal Drugs 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000005708 Sodium hypochlorite Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
この発明はグリオキザールの酸化法によるグリ
オキシル酸の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing glyoxylic acid by an oxidation method of glyoxal.
アセトアルデヒド、ブチルアルデヒドなど普通
の脂肪族アルデヒドは金属、例えばマンガン塩の
存在下に空気などの酸素含有ガスで酸化して対応
するカルボン酸に変えることができる。しかしグ
リオキザールの場合は酸素と反応せずグリオキシ
ル酸を得ることができない。他の酸化剤、例えば
過酸化水素を用いた場合はグリオキザールはギ酸
に酸化され、グリオキシル酸は得られない。更に
次亜塩素酸ナトリウムによつてもグリオキザール
は酸化されるが、グリオキシル酸は全く得られな
い。 Common aliphatic aldehydes such as acetaldehyde and butyraldehyde can be oxidized to the corresponding carboxylic acids with an oxygen-containing gas such as air in the presence of a metal, such as a manganese salt. However, glyoxal does not react with oxygen and cannot yield glyoxylic acid. When using other oxidizing agents, such as hydrogen peroxide, glyoxal is oxidized to formic acid and glyoxylic acid is not obtained. Furthermore, although glyoxal is oxidized by sodium hypochlorite, no glyoxylic acid is obtained.
かくてグリオキザールの酸化によるグリオキシ
ル酸の製法としては長い間硝酸酸化法が唯一の方
法として知られており、他の酸化法としては最近
電解酸化法（特開昭55−79884）が知られただけ
である。 Thus, the nitric acid oxidation method has long been known as the only method for producing glyoxylic acid by oxidizing glyoxal, and the electrolytic oxidation method (Japanese Patent Application Laid-open No. 79884-1983) has only recently become known as another oxidation method. It is.
しかし今や次亜塩素酸を用いてグリオキザール
水溶液を酸化してグリオキシル酸を得る方法が見
出された。アルカリ性の次亜塩素酸ナトリウムで
はグリオキシル酸が得られなかつたことを考えれ
ば酸性条件下で反応させることにより全く反応の
様相が異なり、グリオキシル酸が得られることは
予想外のことである。 However, a method has now been found to obtain glyoxylic acid by oxidizing an aqueous glyoxal solution using hypochlorous acid. Considering that glyoxylic acid could not be obtained with alkaline sodium hypochlorite, it was unexpected that the reaction was completely different and glyoxylic acid was obtained by reacting under acidic conditions.
次亜塩素酸は通常ナトリウム塩やカルシウム塩
の形で入手できるので酸性条件下でグリオキザー
ル水溶液と反応させるためには酸を添加するのが
普通である。普通には塩酸、硫酸などの鉱酸が用
いられるが、所望によつてはリン酸、酢酸など次
亜塩素酸より強い他の酸を用いてもよい。 Since hypochlorous acid is usually available in the form of sodium salt or calcium salt, an acid is usually added in order to react with an aqueous glyoxal solution under acidic conditions. Mineral acids such as hydrochloric acid and sulfuric acid are usually used, but other acids stronger than hypochlorous acid such as phosphoric acid and acetic acid may be used if desired.
反応は、例えば次亜塩素酸ナトリウム水溶液を
グリオキザールと塩酸とを含む酸性の水溶液中に
滴下することによつておこなわれる。滴下された
酸化剤は酸性水溶液中で次亜塩素酸に変つてグリ
オキザールと反応する。酸性条件下でおこなえる
限り他のいかなる反応方法をとることもできる。
例えば硫酸水溶液中にグリオキザール水溶液と次
亜塩素酸ナトリウム水溶液とを別々に滴下しても
よい。 The reaction is carried out, for example, by dropping an aqueous solution of sodium hypochlorite into an acidic aqueous solution containing glyoxal and hydrochloric acid. The dropped oxidizing agent changes into hypochlorous acid in the acidic aqueous solution and reacts with glyoxal. Any other reaction method can be used as long as it can be carried out under acidic conditions.
For example, an aqueous glyoxal solution and an aqueous sodium hypochlorite solution may be separately dropped into an aqueous sulfuric acid solution.
実施例
グリオキザール7.52％および塩酸9.47％を含む
グリオキザール水溶液385.7ｇに8.40％の次亜塩
素酸ナトリウム水溶液443.1ｇを30℃で３時間で
滴下し、グリオキザール1.05％およびグリオキシ
ル酸1.40％を含む反応液828.5ｇを得た。この時
グリオキザール変化化率は70.0％、グリオキシル
酸選択率は44.6％であつた。Example: To 385.7 g of glyoxal aqueous solution containing 7.52% glyoxal and 9.47% hydrochloric acid, 443.1 g of 8.40% sodium hypochlorite aqueous solution was added dropwise at 30°C for 3 hours, and 828.5 g of the reaction solution containing glyoxal 1.05% and glyoxylic acid 1.40% was added dropwise. I got g. At this time, the glyoxal conversion rate was 70.0% and the glyoxylic acid selectivity was 44.6%.
比較例
グリオキザール10.29％およびグリオキシル酸
0.87％を含むグリオキザール水溶液282.0ｇに8.40
％の次亜塩素酸ナトリウム水溶液443.1ｇを30℃
で３時間で滴下し、グリオキザール3.25％および
グリオキシル酸0.11％を含む反応液721.3ｇを得
た。Comparative example glyoxal 10.29% and glyoxylic acid
8.40 in 282.0g of glyoxal aqueous solution containing 0.87%
% sodium hypochlorite aqueous solution at 30℃
The mixture was added dropwise over 3 hours to obtain 721.3 g of a reaction solution containing 3.25% glyoxal and 0.11% glyoxylic acid.
この時のグリオキザール変化率は19.2％である
がグリオキシル酸の増加量はなかつた。 The glyoxal change rate at this time was 19.2%, but there was no increase in glyoxylic acid.
Claims (1)
酸の製法において酸化剤として次亜塩素酸を用
い、これとグリオキザール水溶液とを酸性条件下
で処理することを特徴とするグリオキシル酸の製
造法。1. A method for producing glyoxylic acid using a glyoxal oxidation method, which comprises using hypochlorous acid as an oxidizing agent and treating this and an aqueous glyoxal solution under acidic conditions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14523081A JPS5846037A (en) | 1981-09-14 | 1981-09-14 | Preparation of glyoxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14523081A JPS5846037A (en) | 1981-09-14 | 1981-09-14 | Preparation of glyoxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5846037A JPS5846037A (en) | 1983-03-17 |
| JPH0133099B2 true JPH0133099B2 (en) | 1989-07-11 |
Family
ID=15380342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14523081A Granted JPS5846037A (en) | 1981-09-14 | 1981-09-14 | Preparation of glyoxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5846037A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1169697B (en) * | 1983-12-16 | 1987-06-03 | Montedison Spa | PROCESS FOR THE OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5750969A (en) * | 1980-09-11 | 1982-03-25 | Paamakemu Asia:Kk | Preparation of 5-ureidohydantoin |
-
1981
- 1981-09-14 JP JP14523081A patent/JPS5846037A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5750969A (en) * | 1980-09-11 | 1982-03-25 | Paamakemu Asia:Kk | Preparation of 5-ureidohydantoin |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5846037A (en) | 1983-03-17 |
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