JPS63255247A - Production of malonic acid esters - Google Patents
Production of malonic acid estersInfo
- Publication number
- JPS63255247A JPS63255247A JP62088787A JP8878787A JPS63255247A JP S63255247 A JPS63255247 A JP S63255247A JP 62088787 A JP62088787 A JP 62088787A JP 8878787 A JP8878787 A JP 8878787A JP S63255247 A JPS63255247 A JP S63255247A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- malonic acid
- alkyl
- oxide
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000005406 washing Methods 0.000 abstract description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract 1
- -1 alkali metal alkoxides Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- JLHADLTXDDGZFX-UHFFFAOYSA-L [[acetyloxy(dibutyl)stannyl]oxy-dibutylstannyl] acetate Chemical compound CCCC[Sn](CCCC)(OC(C)=O)O[Sn](CCCC)(CCCC)OC(C)=O JLHADLTXDDGZFX-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 1
- IRCUSRKMPCOMRN-UHFFFAOYSA-M dioctyltin(1+);acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)CCCCCCCC IRCUSRKMPCOMRN-UHFFFAOYSA-M 0.000 description 1
- FHEQTPVGRGPNHS-UHFFFAOYSA-M dioctyltin(1+);dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)CCCCCCCC FHEQTPVGRGPNHS-UHFFFAOYSA-M 0.000 description 1
- DUHNMIFTUKLTJJ-UHFFFAOYSA-N ethyl-methyl-oxotin Chemical compound CC[Sn](C)=O DUHNMIFTUKLTJJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JHRUIJPOAATFRO-UHFFFAOYSA-N oxo(dipropyl)tin Chemical compound CCC[Sn](=O)CCC JHRUIJPOAATFRO-UHFFFAOYSA-N 0.000 description 1
- MUHCAXWYKVQBJV-UHFFFAOYSA-N oxo-di(propan-2-yl)tin Chemical compound CC(C)[Sn](=O)C(C)C MUHCAXWYKVQBJV-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- 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】
[産業上の利用分野]
本発明はエステル交換反応によりマロン酸ジアルキルエ
ステル類を製造する方法に関し、特にそれに用いるエス
テル交換触媒に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing malonic acid dialkyl esters by transesterification, and particularly to a transesterification catalyst used therein.
[従来の技術]
エステル交換触媒としては、硫酸、アルカリ金属アルコ
キシド、アルミニウムアルコキシド、チタンアルコキシ
ドなどが知られている。[Prior Art] Sulfuric acid, alkali metal alkoxides, aluminum alkoxides, titanium alkoxides, and the like are known as transesterification catalysts.
[発明が解決しようとする問題点]
しかしながら、これらの触媒は以下のような問題点を有
していた。[Problems to be Solved by the Invention] However, these catalysts had the following problems.
たとえば、硫酸を触媒に用いた場合に、第2級アルコー
ルを原料に使用すると、その一部が脱水されてオレフィ
ンを副生じたり、工業的に実施した場合、装置を腐食す
る。For example, if sulfuric acid is used as a catalyst and a secondary alcohol is used as a raw material, part of it will be dehydrated to produce olefins as a by-product, or if carried out industrially, it will corrode equipment.
アルカリ金属アルコキ′シトを触媒に用いた場合、触媒
活性が反応中に徐々に低下し、くり返し加えなければな
らないこと、触媒を添加する前に原料中の微量水分を除
去しておく必要があること、触媒の再利用が不可能であ
ること、また洗節工程が必要なことなどの問題があった
。When an alkali metal alkoxide is used as a catalyst, the catalytic activity gradually decreases during the reaction and it must be added repeatedly, and it is necessary to remove trace amounts of water from the raw material before adding the catalyst. However, there were problems such as the impossibility of reusing the catalyst and the necessity of a washing process.
また、アルミニウムアルコキシドや、チタンアルコキシ
ドを触媒に用いた場合には、触媒活性が低いので反応時
間がかかること、事前に原料中の微量水分を除去してお
かなければならないこと、洗浄工程が必要なことなどの
問題があった。Additionally, when aluminum alkoxide or titanium alkoxide is used as a catalyst, the reaction time is longer due to low catalytic activity, trace amounts of water in the raw materials must be removed in advance, and a cleaning process is required. There were other problems.
本発明は以上のような問題点の解決を目的とする。すな
わち、エステル交換反応によりマロン酸ジメチルエステ
ルよりマロン酸ジアルキルエステルを製造するに際し、
触媒として、反応系中の微量水分に影響されず、触媒活
性が低下せず、副反応を引き起こさず、洗浄工程が不要
で、また触媒として再使用の可能な物質を用いて高収率
で高純度の目的物を製造することを目的とする。The present invention aims to solve the above problems. That is, when producing malonic acid dialkyl ester from malonic acid dimethyl ester by transesterification reaction,
As a catalyst, it is not affected by trace amounts of moisture in the reaction system, does not reduce catalytic activity, does not cause side reactions, does not require a washing process, and uses a material that can be reused as a catalyst to achieve high yields. The purpose is to produce a target product of purity.
[問題点を解決するための手段および作用]本発明はア
ルコールとマロン酸ジメチルエステルをエステル交換さ
せ、マロン酸ジアルキルエステル酸(アルキル基の炭素
原子が2以上)を製造するに際し、触媒として一般式C
I)または(II)で表わされる有機スズ化合物を用い
ることを特徴とするマロン酸ジアルキルエステル類の製
造方法である。[Means and effects for solving the problems] The present invention is directed to transesterifying alcohol and malonic acid dimethyl ester to produce a malonic acid dialkyl ester acid (alkyl group has 2 or more carbon atoms) using the general formula as a catalyst. C
This is a method for producing malonic acid dialkyl esters, which is characterized by using an organic tin compound represented by I) or (II).
2゛、 Sn譚0 (1) 2、′ (註)但し。2゛、 Sn Tan 0 (1) 2,' (Note) However.
R1,R2: C,〜C8のアルキル基R3,R4,
R5,Rb: Ca−C8のアルキル基R7:C1−C
nのアルキル基
本発明に用いるエステル交換触媒(1)。R1, R2: C, ~C8 alkyl group R3, R4,
R5, Rb: Ca-C8 alkyl group R7: C1-C
Transesterification catalyst (1) used in the alkyl basic invention of n.
(II)は、塩化ビニルの安定剤や農薬原料として市販
されており、容易に入手できる。この触媒は反応系中の
微量水分に影響されないので事前の脱水工程が不要であ
ること、反応中触媒活性が低下しないので反応時間が短
かいこと、副反応を引き起こさないこと、洗浄工程が不
要であること、また、蒸留残渣を反応に再利用すると、
再び触媒として使用可能であることなどの特長を有する
。(II) is commercially available as a stabilizer for vinyl chloride and as a raw material for agricultural chemicals, and is easily available. This catalyst is not affected by trace amounts of moisture in the reaction system, so there is no need for a dehydration step in advance, the reaction time is short because the catalyst activity does not decrease during the reaction, it does not cause side reactions, and there is no need for a washing step. Also, if the distillation residue is reused in the reaction,
It has the advantage of being able to be used again as a catalyst.
本発明に用いるエステル交換触媒(I)としては、例え
ばジメチルスズオキシド、エチルメチルスズオキシド、
ジプロピルスズオキシド、ジイソプロピルスズオキシド
、ジブチルスズオキシド、ジオクチルスズオキシドなど
が挙げられるが、特にジブチルスズオキシド、ジオクチ
ルスズオキシドが好ましい、またエステル交換触媒(I
I)としては、例えばビス(ジブチルアセトキシスズ)
オキサイド、ビス(ジブチルオクタノイルオキシスズ)
オキサイド、ビス(ジブチルラウロイルオキシスズ)オ
キサイド、ビス(ジブチルステアロイルオキシスズ)オ
キサイド、ビス(ジオクチルアセトキシスズ)オキサイ
ド、ビス(ジオクチルオクタノイルオキシスズ)オキサ
イド、ビス(ジオクチルラウロイルオキシスズ)オキサ
イド、ビス(ジオクチルステアロイルオキシスズ)オキ
サイドなどが挙げられるが、特にビス(ジブチルオクタ
ノイルオキシスズ)オキサイド、ビス(ジブチルラウロ
イルオキシスズ)オキサイド、ビス(ジブチルステアロ
イルオキシスズ)オキサイドからなる群より少なくとも
1種を用いるのが好ましい。Examples of the transesterification catalyst (I) used in the present invention include dimethyltin oxide, ethylmethyltin oxide,
Examples include dipropyltin oxide, diisopropyltin oxide, dibutyltin oxide, and dioctyltin oxide, with dibutyltin oxide and dioctyltin oxide being particularly preferred.
As I), for example, bis(dibutylacetoxytin)
Oxide, bis(dibutyloctanoyloxytin)
oxide, bis(dibutyllauroyloxytin) oxide, bis(dibutylstearoyloxytin) oxide, bis(dioctyl acetoxytin) oxide, bis(dioctyl octanoyloxytin) oxide, bis(dioctyl lauroyloxytin) oxide, bis(dioctyl Examples include stearoyloxytin oxide, and in particular, it is preferable to use at least one member from the group consisting of bis(dibutyloctanoyloxytin) oxide, bis(dibutyllauroyloxytin) oxide, and bis(dibutylstearoyloxytin) oxide. preferable.
これらの触媒の使用量は、原料のマロン酸ジメチルに対
し0.1〜5.0モル%、好ましくは0.25〜2.5
モル%用いるのが良い。The amount of these catalysts used is 0.1 to 5.0 mol%, preferably 0.25 to 2.5 mol%, based on the raw material dimethyl malonate.
It is better to use mol%.
本発明の製造方法においては、原料のアルコールはマロ
ン酸ジメチル1モルに対し、1.2〜10モル、好まし
くは2.0〜5.0モル用いるのが良い。In the production method of the present invention, the alcohol used as a raw material is preferably used in an amount of 1.2 to 10 mol, preferably 2.0 to 5.0 mol, per 1 mol of dimethyl malonate.
また反応温度は80〜150℃の範囲内で行なうのが好
ましい、80℃以下では触媒活性が低く、150℃以上
では副生成物が多くなる。Further, the reaction temperature is preferably carried out within the range of 80 to 150°C; below 80°C the catalyst activity is low, and above 150°C the amount of by-products increases.
また、反応溶媒としてベンゼン、トルエン、ヘキサンな
どを必要に応じて使用することができる。Furthermore, benzene, toluene, hexane, etc. can be used as a reaction solvent, if necessary.
[実施例]
実施例1
攪拌機、温度計及びオールダシヨウ20段の蒸留塔を備
えたフラスコ中にマロン酸ジ/l チル264.2g(
2,0モル)、エタノール460.7g (10モル)
、触媒としてジブチルスズオキシド4.98gを入れ、
攪拌しつつ加熱した。生成してくるメタノールをエタノ
ールと分留し系外へ取り出すことにより反応を連続的に
進めた。[Example] Example 1 In a flask equipped with a stirrer, a thermometer, and a 20-stage distillation column, 264.2 g of di/l malonate (
2.0 mol), ethanol 460.7g (10 mol)
, 4.98 g of dibutyltin oxide was added as a catalyst,
Heat with stirring. The reaction proceeded continuously by fractionating the produced methanol with ethanol and taking it out of the system.
反応は15時間行い、この間の塔頂温度は63.0〜6
4.0、釜温は81.0〜86.0℃であった。The reaction was carried out for 15 hours, during which the tower top temperature was 63.0-6.
4.0, and the pot temperature was 81.0 to 86.0°C.
反応後、反応混合物をそのまま減圧蒸留し、65.0〜
67.0℃15.0■■Hgの留分304.4gを得た
。この留分をNMR,IRで分析した結果、マロン酸ジ
エチルであることが確認された。After the reaction, the reaction mixture was distilled under reduced pressure as it was, and the
304.4 g of a fraction with a temperature of 67.0°C and 15.0■■Hg was obtained. As a result of analyzing this fraction by NMR and IR, it was confirmed that it was diethyl malonate.
マロン酸ジエチルの原料マロン酸ジメチルに対する収率
は95.0%であった。The yield of diethyl malonate based on the raw material dimethyl malonate was 95.0%.
実施例2〜8
実施例1と同じ反応装置を使用し、触媒量を原料マロン
酸ジメチルに対し1モル%入れた他は、実施例1と同様
な方法で触媒の種類を変えて本発明を実施した場合の例
を表−1に示す。Examples 2 to 8 The present invention was carried out in the same manner as in Example 1, except that the same reaction apparatus as in Example 1 was used, and the catalyst was added in an amount of 1 mol % based on the raw material dimethyl malonate. Table 1 shows examples of implementation.
表−1
実施例9〜13
実施例1と同じ装置を使用し、実施例1と同様な方法で
アルコールの種をかえて本発明を実施した場合の例を表
−2に示す。Table 1 Examples 9 to 13 Table 2 shows examples in which the present invention was carried out using the same apparatus as in Example 1 and changing the type of alcohol in the same manner as in Example 1.
(以下余白)
[発明の効果]
以上に説明した様に1本発明によって繁雑な操作を行な
わずにマロン酸ジメチルエステルより高収率で高純度の
マロン酸ジアルキルエステルを製造すること力5可ta
になった。(The following is a blank space) [Effects of the Invention] As explained above, it is possible to produce dialkyl malonate with higher yield and purity than dimethyl malonate without complicated operations according to the present invention.
Became.
Claims (1)
反応させ、マロン酸ジアルキルエステル類(アルキル基
の炭素原子が2以上)を製造するに際し、触媒として一
般式( I )または(II)で表わされる有機スズ化合物
を用いることを特徴とするマロン酸ジアルキルエステル
類の製造方法。 ▲数式、化学式、表等があります▼( I ) ▲数式、化学式、表等があります▼(II) (註)但し、 R_1、R_2:C_1〜C_8のアルキル基 R_3、R_4、R_5、R_6:C_4〜C_8のア
ルキル基 R_7:C_1〜C_1_7のアルキル基[Scope of Claims] When alcohol and malonic acid dimethyl ester are transesterified to produce malonic acid dialkyl esters (alkyl group has 2 or more carbon atoms), general formula (I) or (II) is used as a catalyst. A method for producing malonic acid dialkyl esters, which comprises using the organotin compound represented by the formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (Note) However, R_1, R_2: Alkyl group of C_1 to C_8 R_3, R_4, R_5, R_6: C_4 ~C_8 alkyl group R_7: C_1 to C_1_7 alkyl group
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62088787A JPS63255247A (en) | 1987-04-13 | 1987-04-13 | Production of malonic acid esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62088787A JPS63255247A (en) | 1987-04-13 | 1987-04-13 | Production of malonic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63255247A true JPS63255247A (en) | 1988-10-21 |
Family
ID=13952553
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62088787A Pending JPS63255247A (en) | 1987-04-13 | 1987-04-13 | Production of malonic acid esters |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63255247A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995017377A1 (en) * | 1993-12-20 | 1995-06-29 | Nitto Chemical Industry Co. Ltd. | Process for producing higher cyanoacetic ester |
-
1987
- 1987-04-13 JP JP62088787A patent/JPS63255247A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995017377A1 (en) * | 1993-12-20 | 1995-06-29 | Nitto Chemical Industry Co. Ltd. | Process for producing higher cyanoacetic ester |
US5637752A (en) * | 1993-12-20 | 1997-06-10 | Nitto Chemical Industry Co., Ltd. | Method for preparing cyanoacetic acid higher ester |
US5698730A (en) * | 1993-12-20 | 1997-12-16 | Nitto Chemical Industry Co., Ltd. | Method for preparing cyanoacetic acid higher ester |
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