JPS5865245A - Preparation of glycol monoester - Google Patents
Preparation of glycol monoesterInfo
- Publication number
- JPS5865245A JPS5865245A JP56163908A JP16390881A JPS5865245A JP S5865245 A JPS5865245 A JP S5865245A JP 56163908 A JP56163908 A JP 56163908A JP 16390881 A JP16390881 A JP 16390881A JP S5865245 A JPS5865245 A JP S5865245A
- Authority
- JP
- Japan
- Prior art keywords
- aldehyde
- alkaline earth
- oxide
- glycol monoester
- isobutyraldehyde
- 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
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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明はグリコールモノエステルの製造の改良方法に関
する。さらに詳しくは本発明はアルカリ土類金属酸化物
の存在下に、
一般式（ｒ）
（式中、Ｒ８およびＲ８は同−又は異なって炭素数１−
５のアルキル基を表わす。）で表わされるアルデヒドか
ら
一般式（Ｉｔ）
ＯＨＲ＊
（式中、Ｒ１およびＲ２は前記と同意義を表わす。）で
表わされるグリコールモノエステルを製造する方法に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an improved process for the production of glycol monoesters. More specifically, in the presence of an alkaline earth metal oxide, the present invention provides a compound having the general formula (r) (wherein R8 and R8 are the same or different and have a carbon number of 1-
5 represents an alkyl group. ) The present invention relates to a method for producing a glycol monoester represented by the general formula (It) OHR* (wherein R1 and R2 have the same meanings as above) from an aldehyde represented by the formula (It).
従来、触媒を使用するアルデヒドからグリコールモノエ
ステルの製法としては槙々の方法が知られている。例え
ばアルカリ又はアルカリ土類水酸化物触媒を用いる方法
（ＵＳＦ、 ３２９１８２１、ＵＳＦ、３７１８６８９
．特開昭５４−５９２１５号公報等）、アルコール又は
酸共存下にアルカリ又はアルカリ土類水酸化物触媒を用
いる方法（特公昭５２−１５５８１号公報、特公昭５２
−１５５８２号公報、特開昭５４−１４８７１６号公報
等）、アルコラード系、触媒を用いる方法（特公昭３８
−２２８５７号公報、特公昭５２−１５５８０９号公報
、特公昭５２−１５５８１号公報、特公昭４７−３７６
０９号公報等）等が知られている。BACKGROUND ART Conventionally, Maki's method is known as a method for producing glycol monoester from an aldehyde using a catalyst. For example, methods using alkali or alkaline earth hydroxide catalysts (USF, 3291821, USF, 3718689
．． JP-A-54-59215, etc.), a method using an alkali or alkaline earth hydroxide catalyst in the coexistence of alcohol or acid (Japanese Patent Publication No. 52-15581, JP-B-Sho 52)
-15582, JP-A-54-148716, etc.), Alcolade system, method using a catalyst (Japanese Patent Publication No. 1987-148716, etc.)
-22857 Publication, Japanese Patent Publication No. 52-155809, Japanese Patent Publication No. 52-15581, Japanese Patent Publication No. 47-376
No. 09, etc.) are known.
しかしながら、アルデヒドからグリコールモノエステル
を製造する際にアルカリ又はアルカリ土類水酸化物触媒
を用いた場合には、一般的に反応率が低くなる。又、ア
ルコール又は酸共存下にアルカリ又はアルカリ土類水酸
化物触媒を用いた場合には、次の様な問題が起る。However, when an alkali or alkaline earth hydroxide catalyst is used when producing a glycol monoester from an aldehyde, the reaction rate is generally low. Further, when an alkali or alkaline earth hydroxide catalyst is used in the coexistence of alcohol or acid, the following problems occur.
即ち、アルコールを添加する場合には反応後未反応アル
デヒドを分離した後、アルコールを蒸留又は水蒸気蒸留
により分離回収しなければならない。酸を用いる場合に
は１反応後、アルカリによる中和、水洗によって塩を分
離するか、又は蒸留によって分離しなければならずかつ
酸濃度、温度によっては高価な耐食性材料を要する。That is, when adding alcohol, it is necessary to separate unreacted aldehyde after the reaction and then separate and recover the alcohol by distillation or steam distillation. When an acid is used, after one reaction, the salt must be separated by neutralization with an alkali, washing with water, or distillation, and depending on the acid concentration and temperature, expensive corrosion-resistant materials are required.
さらに、又、アルコラード系触媒を用いた場合には、水
分が多いアルデヒドを原料とすると反応率が低下する欠
点がある。Furthermore, when an alcoholade catalyst is used, there is a drawback that the reaction rate decreases if an aldehyde containing a large amount of water is used as a raw material.
本発明者らは、アルデヒドから高収率、高選択率でグリ
コールモノエステルを製造する方法について種々検討し
た結果、アルカリ土類金属酸化物の存在下に、一般式（
１）で表わされるアルデヒドから一般式（ＩＩ）で表わ
されるグリコールモノエステルを高収率、高選択率で製
造できることを孔い出し、本発明を完成ｌ〜だ。The present inventors conducted various studies on methods for producing glycol monoester from aldehydes in high yield and high selectivity.
The present invention was completed by discovering that the glycol monoester represented by the general formula (II) can be produced from the aldehyde represented by 1) in high yield and high selectivity.
以下に、本発明の詳細な説明する。The present invention will be explained in detail below.
一般式（１）で表わされるアルデヒドとしては、例えば
、イソブチルアルデヒド、２−メチルブチルアルデヒド
、２−エチルブチルアルデヒド、２−メチルペンタナー
ル、２−エチルペンタナールなどがあげられる。Examples of the aldehyde represented by the general formula (1) include isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, 2-methylpentanal, and 2-ethylpentanal.
アルデヒドとしては、アルデヒド中の酸、水含量の少な
いもの程好ましいが、水分含量５重量−以下、酸含量２
重量−以下のアルデヒドであれば充分、本発明の原料ア
ルデヒドとして使用できる。As for the aldehyde, the lower the acid and water content in the aldehyde, the more preferable the aldehyde is.
Any aldehyde having a weight of less than - can be used as the raw material aldehyde of the present invention.
アルカリ土類金属酸化物としては酸化バリウム、酸化マ
グネシウム等が用いられる。Barium oxide, magnesium oxide, etc. are used as the alkaline earth metal oxide.
アルカリ土類金属酸化物の量としては、アルデヒドに対
して０．５−１０重量−の範囲が好ましい。接触反応は
５０−１５０℃で０．５−４時間行かう。反応後、反応
液から目的物を得るには、反応液から濾過によ！ｌｌま
ず触媒を分離した後、そのＦ液を通常の蒸留方法で蒸留
することによシ、目的物を分離、精製することができる
。The amount of alkaline earth metal oxide is preferably in the range of 0.5-10% by weight relative to the aldehyde. The catalytic reaction is carried out at 50-150°C for 0.5-4 hours. After the reaction, to obtain the target product from the reaction solution, filter the reaction solution! After first separating the catalyst, the target product can be separated and purified by distilling the F liquid using a conventional distillation method.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例１゜
反応器に無水イソブチルアルデヒド（イソブチルアルデ
ヒド： ９９．８５重ｔ％、水分：０．０３重量％、イ
ソ酪酸： ０．１２重量％）を１００＃入れ、触媒とし
て酸化バリウム（ＢａＯ） （和光純系製）を対アルデ
ヒド１重量％添加し、撹拌しながら８５℃で２−５時間
反応する。Example 1゜ 100 # of anhydrous isobutyraldehyde (isobutyraldehyde: 99.85% by weight, water: 0.03% by weight, isobutyric acid: 0.12% by weight) was placed in a reactor, and barium oxide (BaO) was added as a catalyst. (manufactured by Wako Junkei Co., Ltd.) was added in an amount of 1% by weight based on the aldehyde, and the mixture was reacted at 85° C. for 2 to 5 hours with stirring.
反応後、反応液を室温まで冷却し、ついで反応液からｐ
過によシ触媒を分離したのち、Ｆ液を（５）
ガスクロマトグラフィーにより分析した結果は次の通シ
。After the reaction, the reaction solution was cooled to room temperature, and then p was removed from the reaction solution.
After separating the peroxide catalyst, the F solution was analyzed by gas chromatography (5).The results are as follows.
イソブチルアルデヒドの反応率：ｓ２．３％２、２．４
− ）ジメチル−１，３−ベンタンジオールモノインブ
チレートへの選択率：９４．９％実施例２゜
反応器に含水イソブチルアルデヒド（イソブチルアルデ
ヒド７９４．４８重量％、水分：２重量％、イソ酪酸：
１．５２２重量％を１００ｇ入れ、触媒としてＢａ、ｏ
（和光紬薬Ｍ）を対アルデヒド３重量％添加し、攪拌
しながら１２０℃で１．５時間反応する。以下実施例１
と同様にして次の結果を得た。Reaction rate of isobutyraldehyde: s2.3%2, 2.4
- ) Selectivity to dimethyl-1,3-bentanediol monoimbutyrate: 94.9% Example 2 In a reactor, hydrated isobutyraldehyde (794.48% by weight of isobutyraldehyde, water: 2% by weight, isobutyric acid :
Add 100g of 1.522% by weight, and use Ba, O as a catalyst.
(Wako Tsumugi Yaku M) was added in an amount of 3% by weight based on the aldehyde, and the mixture was reacted at 120° C. for 1.5 hours with stirring. Example 1 below
In the same way, we obtained the following results.
イソブチルアルデヒドの反応率：８０％２．２．４−）
サメチル−１，３−ベンタンジオールモノイソブチレー
トへの選択率：９０．０％（６）Reaction rate of isobutyraldehyde: 80% 2.2.4-)
Selectivity to samethyl-1,3-bentanediol monoisobutyrate: 90.0% (6)
Claims (1)
５のアルキル基を表わす。）で表わされるアルデヒドか
ら 一般式（Ｉｆ） ＯＨＲ。 （式中、Ｒ１およびＲ２は前記と同意義全表わｔ。）で
表わされるグリコールモノエステルを製造する方法。[Claims] In the presence of an alkaline earth metal oxide,
5 represents an alkyl group. ) from the aldehyde represented by the general formula (If) OHR. A method for producing a glycol monoester represented by the formula (wherein R1 and R2 have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56163908A JPS5865245A (en) | 1981-10-14 | 1981-10-14 | Preparation of glycol monoester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56163908A JPS5865245A (en) | 1981-10-14 | 1981-10-14 | Preparation of glycol monoester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5865245A true JPS5865245A (en) | 1983-04-18 |
Family
ID=15783106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56163908A Pending JPS5865245A (en) | 1981-10-14 | 1981-10-14 | Preparation of glycol monoester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5865245A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6215020B1 (en) | 1998-06-30 | 2001-04-10 | Eastman Chemical Company | Basic clay catalyst for the production of pentylglycol monoesters |
| US6632959B2 (en) | 1997-08-07 | 2003-10-14 | Chisso Corporation | Basic catalysts and process for producing carbonyl compound derivatives |
-
1981
- 1981-10-14 JP JP56163908A patent/JPS5865245A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632959B2 (en) | 1997-08-07 | 2003-10-14 | Chisso Corporation | Basic catalysts and process for producing carbonyl compound derivatives |
| US6215020B1 (en) | 1998-06-30 | 2001-04-10 | Eastman Chemical Company | Basic clay catalyst for the production of pentylglycol monoesters |
| US6794325B1 (en) | 1998-06-30 | 2004-09-21 | Eastman Chemical Company | Basic clay catalyst for the production of glycol monoester |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
| US3342858A (en) | Preparation of alkoxy-alkanoic acids by the oxidation of alkoxy-alkanols | |
| JPS58159432A (en) | Preparation of branched dimerized alcohol | |
| JP2001190954A (en) | Palladium catalyst and manufacturing method of ether | |
| JPS5929180B2 (en) | Method for producing glycolic acid | |
| JPS5865245A (en) | Preparation of glycol monoester | |
| US3972943A (en) | Process for preparing alkaliacetylacetonates | |
| JPH0315619B2 (en) | ||
| US3238261A (en) | Piperitenone process | |
| JP4048578B2 (en) | Base catalyst and method for producing carbonyl compound derivative | |
| JP3237541B2 (en) | Reduction method of aldehyde or ketone | |
| SU1567565A1 (en) | Method of obtaining 1-chlor-4-methylpentan 2-ol | |
| JPH062716B2 (en) | Method for producing aromatic secondary amino compound | |
| JPH0228583B2 (en) | ||
| JPH0546253B2 (en) | ||
| JPS59157039A (en) | Production of xylylene glycol | |
| JPS647977B2 (en) | ||
| JPS60139634A (en) | Production of thymol | |
| JPS6087281A (en) | Preparation of dioxanetriol | |
| JPH08119904A (en) | Production of lactic acid ester | |
| JPS5933569B2 (en) | Method for producing O-alkoxy-P-allylphenol | |
| JP2005060371A (en) | Method for producing pyridylethylthio compound, method for producing modified ion-exchanger and bisphenol comound | |
| JPH0791253B2 (en) | Method for producing ethylene cyanohydrin | |
| JPH0153273B2 (en) | ||
| SU620472A1 (en) | Method of obtaining allylvinyl ester |