JPS6147822B2 - - Google Patents
Info
- Publication number
- JPS6147822B2 JPS6147822B2 JP53159270A JP15927078A JPS6147822B2 JP S6147822 B2 JPS6147822 B2 JP S6147822B2 JP 53159270 A JP53159270 A JP 53159270A JP 15927078 A JP15927078 A JP 15927078A JP S6147822 B2 JPS6147822 B2 JP S6147822B2
- Authority
- JP
- Japan
- Prior art keywords
- lactic acid
- manganese dioxide
- reaction
- acid nitrile
- nitrile
- 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
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 32
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 25
- 239000004310 lactic acid Substances 0.000 claims description 23
- 235000014655 lactic acid Nutrition 0.000 claims description 23
- -1 lactic acid nitrile Chemical class 0.000 claims description 21
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000036571 hydration Effects 0.000 description 10
- 238000006703 hydration reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000003541 multi-stage reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は、乳酸アミドの製造方法に関するもの
である。さらに詳細には、乳酸ニトリルを接触的
に水和して、乳酸アミドを製造する方法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing lactic acid amide. More specifically, the present invention relates to a method for producing lactic acid amide by catalytically hydrating lactic acid nitrile.
乳酸アミドは、従来、乳酸をアンモニアで中和
し乳酸アンモニウムとし、これを、例えば五酸化
リン等で脱水する方法で製造されており、多段の
反応操作と繁雑な分離方法が必要であつた。 Lactic acid amide has conventionally been produced by neutralizing lactic acid with ammonia to produce ammonium lactate, which is then dehydrated with, for example, phosphorus pentoxide, which requires multi-stage reaction operations and complicated separation methods.
本発明の目的とするところは、従来法のような
多段の反応操作と繁雑な分離操作を必要としな
い、新規な乳酸アミドの製造方法を提供すること
にある。 An object of the present invention is to provide a novel method for producing lactic acid amide, which does not require the multi-stage reaction operations and complicated separation operations required in conventional methods.
アミドを製造する一般的方法はニトリルの水和
である。近年、触媒を用いて接触的にニトリルの
水和を実施することが行なわれ、特に、アクリロ
ニトリルの水和によるアクリルアミドの製造が大
規模に工業化されている。 A common method for making amides is the hydration of nitriles. In recent years, catalytic hydration of nitriles has been carried out using catalysts, and in particular, the production of acrylamide by hydration of acrylonitrile has been industrialized on a large scale.
アクリルニトリルの水和には銅、特に、ラネー
銅のような金属銅触媒が極めて高い活性を示すこ
とがよく知られ工業的にも使用されている。 It is well known that copper, especially metallic copper catalysts such as Raney copper, exhibit extremely high activity in the hydration of acrylonitrile, and are also used industrially.
本発明者は、乳酸ニトリルの接触水和に用いる
触媒に関して種々研究した結果、アクリルニトリ
ルの水和に有効な銅触媒は、全く活性を示さず
に、二酸化マンガンが極めて有効であることを見
出し、本発明を完成するに至つた。 As a result of various studies on catalysts used for catalytic hydration of lactic acid nitrile, the present inventor found that copper catalysts that are effective in hydrating acrylonitrile show no activity at all, while manganese dioxide is extremely effective. The present invention has now been completed.
ニトリルの接触水和に二酸化マンガンが有効で
あることは古くから公知であるが、例えば
chemical communications121〜122（1966）、乳
酸ニトリルのように容易に酸化され易いアルコー
ル基を分子内に持つニトリルは、二酸化マンガン
により酸化を受けると考えられ、乳酸ニトリルの
二酸化マンガン触媒による水和は、行なわれてい
なかつた。すなわち、乳酸ニトリルはアルコール
の酸化剤として多用されているところの二酸化マ
ンガンによりピルボニトリルへ酸化され、生じた
ピルボニトリルは不安定であるため、アセトアル
デヒドと青酸に分解し、一方、二酸化マンガンは
低位のマンガン酸化物に還元され水和活性を消失
すると推定されていた。ところが、本発明者の研
究によれば、乳酸ニトリルの水溶液を30〜200℃
の温度で二酸化マンガンと接触させると、意外な
ことに、アルコールの酸化は実質的に進行せず、
ニトリルのアミドへの水和が選択的に進行するこ
と、さらに、アルコールの酸化が実質的に進行し
ないため、二酸化マンガンの還元も実質的に進行
せず、したがつて触媒活性の低下も認められない
ことを見出した。 It has been known for a long time that manganese dioxide is effective for catalytic hydration of nitriles, but for example,
Chemical Communications 121-122 (1966) Nitriles with easily oxidized alcohol groups in their molecules, such as lactic acid nitrile, are thought to be oxidized by manganese dioxide, and hydration of lactic acid nitrile with a manganese dioxide catalyst is not possible. It wasn't. In other words, lactic acid nitrile is oxidized to pyrvonitrile by manganese dioxide, which is often used as an oxidizing agent for alcohol, and the resulting pyrbonitrile is unstable, so it decomposes into acetaldehyde and hydrocyanic acid, while manganese dioxide is a low-level manganese oxidizer. It was presumed that the hydration activity would be lost by being reduced to other substances. However, according to the research of the present inventor, an aqueous solution of lactic acid nitrile was heated at 30 to 200°C.
Surprisingly, when brought into contact with manganese dioxide at a temperature of
Since the hydration of nitrile to amide proceeds selectively and the oxidation of alcohol does not substantially proceed, the reduction of manganese dioxide also does not substantially proceed, and therefore a decrease in catalytic activity is observed. I found out that there is no.
すなわち、本発明の要旨とするところは、乳酸
ニトリル水溶液を30〜200℃の温度で二酸化マン
ガンに接触させ選択的に乳酸アミドを製造するこ
とにある。 That is, the gist of the present invention is to selectively produce lactic acid amide by bringing an aqueous lactic acid nitrile solution into contact with manganese dioxide at a temperature of 30 to 200°C.
したがつて、本発明の方法によれば、乳酸ニト
リルの接触水和による一段の反応操作により、従
来法のような欠点もなく工業的に有利に乳酸アミ
ドを製造することができる。 Therefore, according to the method of the present invention, lactic acid amide can be industrially advantageously produced without the disadvantages of conventional methods by a one-step reaction operation involving catalytic hydration of lactic acid nitrile.
本発明の方法において原料物質として用いられ
る乳酸ニトリルは、アセトアルデヒドと青酸との
反応によつて、容易に製造でき、工業的に大量安
価に供給されている化合物である。 Lactic acid nitrile used as a raw material in the method of the present invention is a compound that can be easily produced by the reaction of acetaldehyde and hydrocyanic acid, and is supplied industrially in large quantities at low cost.
本発明の方法において用いる乳酸ニトリルの水
溶液は、乳酸ニトリルの濃度が１〜50wt％、好
ましくは５〜30wt％の範囲である。 The aqueous solution of lactic acid nitrile used in the method of the present invention has a lactic acid nitrile concentration in the range of 1 to 50 wt%, preferably 5 to 30 wt%.
乳酸ニトリル水溶液と触媒である二酸化マンガ
ンを接触させる反応温度は、30〜200℃、好まし
くは50〜130℃の範囲である。反応温度が上記し
た範囲より低いと、反応速度が遅く実質的でな
い、反応温度が上記範囲より高いと、乳酸ニトリ
ルの分解およびアルコール基の酸化反応が併発
し、収率が低下するので好ましくない。 The reaction temperature at which the lactic acid nitrile aqueous solution and the catalyst manganese dioxide are brought into contact is in the range of 30 to 200°C, preferably 50 to 130°C. If the reaction temperature is lower than the above range, the reaction rate is slow and not substantial, and if the reaction temperature is higher than the above range, the decomposition of lactic acid nitrile and the oxidation reaction of alcohol groups occur simultaneously, resulting in a decrease in yield, which is not preferable.
本発明の方法において用いる触媒は二酸化マン
ガンであつて、マンガン塩、例えば、硝酸マンガ
ン等の熱分解により製造するか、または、市販品
の二酸化マンガンをそのまま使用する。触媒の形
態は、粉末状、粒状または錠剤に整型したもので
あつて、懸濁床反応器に用いる場合は粉末、固定
床反応器に用いる場合には、粒状または錠剤を用
いる。二酸化マンガンを担体上に担持したものも
同様に使用できる。 The catalyst used in the process of the invention is manganese dioxide, which can be prepared by thermal decomposition of manganese salts, such as manganese nitrate, or commercially available manganese dioxide can be used as is. The catalyst may be in the form of powder, granules, or tablets; powder is used in a suspended bed reactor, and granules or tablets are used in a fixed bed reactor. A carrier in which manganese dioxide is supported can also be used.
触媒の使用量は特に制限はないが、他の触媒反
応の場合に比較して多量の触媒を用いる。例え
ば、固定床で反応を実施する際には、触媒床と乳
酸ニトリル水溶液との接触時間は２〜10時間の範
囲である。 Although there is no particular restriction on the amount of catalyst used, a larger amount of catalyst is used than in the case of other catalytic reactions. For example, when carrying out the reaction in a fixed bed, the contact time between the catalyst bed and the aqueous lactic acid nitrile solution ranges from 2 to 10 hours.
反応終了後、反応液から触媒を分離すれば、乳
酸アミド水溶液が得られ、これを減圧下に濃縮す
れば、固体状の乳酸アミドが白色粉末として析出
する。 After the reaction is completed, the catalyst is separated from the reaction solution to obtain an aqueous lactic acid amide solution, which is concentrated under reduced pressure to precipitate solid lactic acid amide as a white powder.
本発明の方法で得られる乳酸アミドは、乳酸、
乳酸エステル、および有機薬品の合成原料とし
て、有用な化合物である。 The lactic acid amide obtained by the method of the present invention includes lactic acid,
It is a useful compound as a raw material for the synthesis of lactic acid esters and organic drugs.
以下、実施例および比較例により、本発明を説
明する。 The present invention will be explained below with reference to Examples and Comparative Examples.
比較例 １
乳酸ニトリルの10wt％水溶液50ｇに、常法に
よつて展開したラネー銅触媒、〔アクリロニトリ
ルの水和に高活性を示す〕２ｇを添加し、還流冷
却器を付けた三角フラスコ中で、90〜95℃で５時
間撹拌した。反応液から触媒を分離し、ガスクロ
マトグラフイーで生成物を分析したところ、乳酸
アミドの生成は痕跡量であり、乳酸ニトリルから
乳酸アミドへの転化は、実質的に進行しない。Comparative Example 1 To 50 g of a 10 wt % aqueous solution of lactic acid nitrile, 2 g of Raney copper catalyst [which shows high activity in hydrating acrylonitrile] developed by a conventional method was added, and the mixture was placed in an Erlenmeyer flask equipped with a reflux condenser. Stirred at 90-95°C for 5 hours. When the catalyst was separated from the reaction solution and the product was analyzed by gas chromatography, it was found that only a trace amount of lactic acid amide was produced, and the conversion of lactic acid nitrile to lactic acid amide did not substantially proceed.
実施例 １
還流冷却器を付けた100c.c.三角フラスコ中に
10wt％の乳酸ニトリル水溶液50ｇ、市販特級試
薬の二酸化マンガン粉末８ｇを仕込み、80℃で５
時間撹拌しながら反応させた。反応液から触媒を
分離し、ガスクロマトグラフイーで生成物を分析
したところ、乳酸ニトリルの転化率92％、乳酸ア
ミドへの選択率81％であつた。副生物はアセトア
ルデヒドおよび微量の酢酸が認められた。反応液
を減圧下に蒸発乾固し、得られた白色粉末の赤外
吸収スペクトルを測定したところ、標品のそれと
よく一致した。Example 1 In a 100 c.c. Erlenmeyer flask equipped with a reflux condenser.
Prepare 50g of 10wt% lactic acid nitrile aqueous solution and 8g of manganese dioxide powder, a commercially available special reagent, and heat at 80℃ for 50 minutes.
The reaction was allowed to take place while stirring for hours. When the catalyst was separated from the reaction solution and the product was analyzed by gas chromatography, the conversion rate of lactic acid nitrile was 92% and the selectivity to lactic acid amide was 81%. Acetaldehyde and trace amounts of acetic acid were observed as by-products. The reaction solution was evaporated to dryness under reduced pressure, and the infrared absorption spectrum of the resulting white powder was measured, and it matched well with that of the standard product.
実施例 ２
内径12m/mφのガラス管の外側にジヤケツト
を付け、80℃の温水を循環させる固定床反応器と
した。上記反応器に粒径１〜２m/mφの粒状二
酸化マンガン９mlを充填（層高10cm）した。充填
塔の底部より上方に向けて10wt％の乳酸ニトリ
ル水溶液を、定量ポンプにより2.5ｇ／Hrの流速
で注入し、上部より流出する反応液を冷却補集し
た。補集液を分析したところ乳酸ニトリルの転化
率90％、乳酸アミドへの選択率82％であつた。Example 2 A jacket was attached to the outside of a glass tube with an inner diameter of 12 m/mφ to form a fixed bed reactor in which hot water at 80°C was circulated. The reactor was filled with 9 ml of granular manganese dioxide having a particle size of 1 to 2 m/mφ (bed height 10 cm). A 10 wt % lactic acid nitrile aqueous solution was injected upward from the bottom of the packed tower at a flow rate of 2.5 g/Hr using a metering pump, and the reaction liquid flowing out from the top was collected by cooling. Analysis of the collected solution revealed that the conversion rate of lactic acid nitrile was 90% and the selectivity to lactic acid amide was 82%.
Claims (1)
で、二酸化マンガンと接触させることを特徴とす
る乳酸アミドの製造方法。1. A method for producing lactic acid amide, which comprises bringing an aqueous solution of lactic acid nitrile into contact with manganese dioxide at a temperature of 30 to 200°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15927078A JPS5587749A (en) | 1978-12-26 | 1978-12-26 | Preparation of lactamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15927078A JPS5587749A (en) | 1978-12-26 | 1978-12-26 | Preparation of lactamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5587749A JPS5587749A (en) | 1980-07-02 |
| JPS6147822B2 true JPS6147822B2 (en) | 1986-10-21 |
Family
ID=15690095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15927078A Granted JPS5587749A (en) | 1978-12-26 | 1978-12-26 | Preparation of lactamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5587749A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8691130B2 (en) | 2003-06-19 | 2014-04-08 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US9598802B2 (en) | 2013-12-17 | 2017-03-21 | Eastman Chemical Company | Ultrafiltration process for producing a sulfopolyester concentrate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104543922A (en) * | 2014-12-31 | 2015-04-29 | 南通双和食品有限公司 | Food acidulant and preparing method thereof |
-
1978
- 1978-12-26 JP JP15927078A patent/JPS5587749A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8691130B2 (en) | 2003-06-19 | 2014-04-08 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US9598802B2 (en) | 2013-12-17 | 2017-03-21 | Eastman Chemical Company | Ultrafiltration process for producing a sulfopolyester concentrate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5587749A (en) | 1980-07-02 |
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