JPH03291255A - Production of alkoxypronionic acid alkyl esters - Google Patents
Production of alkoxypronionic acid alkyl estersInfo
- Publication number
- JPH03291255A JPH03291255A JP2091197A JP9119790A JPH03291255A JP H03291255 A JPH03291255 A JP H03291255A JP 2091197 A JP2091197 A JP 2091197A JP 9119790 A JP9119790 A JP 9119790A JP H03291255 A JPH03291255 A JP H03291255A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- equivalent
- substance
- melting point
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title 1
- 125000005907 alkyl ester group Chemical group 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 239000000126 substance Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000011734 sodium Substances 0.000 claims abstract description 11
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 11
- 239000010409 thin film Substances 0.000 claims abstract description 11
- 238000002844 melting Methods 0.000 claims abstract description 10
- 230000008018 melting Effects 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 8
- 238000001704 evaporation Methods 0.000 abstract description 5
- 230000008020 evaporation Effects 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- -1 U.S. Pat. No. 3 Chemical compound 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LQNHLKOBKGLWSH-UHFFFAOYSA-M sodium;3-ethoxypropanoate Chemical compound [Na+].CCOCCC([O-])=O LQNHLKOBKGLWSH-UHFFFAOYSA-M 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 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
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- 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〕
本発明はアルフキジプロピオン酸アルキル類の製造方法
に関し、さらに詳しくはアクリル酸アルキル類とアルコ
ール類とを触媒の存在下に効率良く反応させ、それぞれ
の原料に対応するアルコキシプロピオン酸アルキル類を
製造する方法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing alkyl alphkyl dipropionates, and more specifically, a method for efficiently reacting an alkyl acrylate and an alcohol in the presence of a catalyst, The present invention relates to a method for producing alkyl alkoxypropionates corresponding to each raw material.
従来アルコキシプロピオン酸アルキル類を製造するには
■アルコール類とアクリル酸アルキル類の反応（例えば
、Ｊ、４ｍ、 Ｃｈｅｗ、 Ｓｏｃ、 ６８ ＠ ５４
４頁１９４６年）、■エチレンとアルコール類と一酸化
炭素の反応（例えば、米国特許３，７５５，４２１）、
■アクロレンとアルコール類の反応（例えば、特開昭５
０−４６．６１４） 、■ケテン出発の反応（例えば、
米国特許８２８，３７１）等による方法がある。Conventionally, to produce alkyl alkoxypropionates, ■Reaction of alcohol and alkyl acrylate (for example, J, 4m, Chew, Soc, 68 @ 54
4 p. 1946), ■ Reaction of ethylene, alcohols, and carbon monoxide (e.g., U.S. Pat. No. 3,755,421),
■Reaction of acrolene and alcohols (for example, JP-A-5
0-46.614), ■ Reaction starting from ketene (e.g.
There are methods such as those disclosed in US Pat. No. 828,371).
これらの製造法のうちアルコキシプロピオン酸アルキル
類の生成選択性、原料入手の容易さ等の点で■のアルコ
ール類とアクリル酸アル牛ル類トの反応による方法が優
れている。この■の方法はアクリル酸アルキル類にアル
コール類を付加させる方法であり、通常塩基性物質が触
媒として用いられ、塩基性触媒としては、例えば金属ア
ルコラード、水酸化アルカリ、塩基性金属塩等があげら
れる。塩基性触媒以外には、金属錯体を触媒とする方法
も知られているが、これら塩基性触媒、金属錯体触媒は
いずれも均一系触媒であり、反応後の触媒分離が必須で
ある。Among these production methods, the method (2), which involves the reaction of alcohols and alkylate acrylates, is superior in terms of selectivity for producing alkoxypropionates, ease of obtaining raw materials, and the like. This method (2) is a method of adding alcohols to alkyl acrylates, and a basic substance is usually used as a catalyst. Examples of basic catalysts include metal alcoholades, alkali hydroxides, and basic metal salts. It will be done. In addition to basic catalysts, methods using metal complexes as catalysts are also known, but these basic catalysts and metal complex catalysts are both homogeneous catalysts, and catalyst separation after the reaction is essential.
また、固体触媒については、イオン交換樹脂を用いる方
法（特開昭６３−１０７９４９）が提案されているが、
触媒寿命が短く、生産ζこ使用するには、満足できる技
術ではない。Regarding solid catalysts, a method using an ion exchange resin has been proposed (Japanese Patent Application Laid-open No. 63-107949).
The catalyst life is short and the technology is not satisfactory for production use.
従って、アルコキシプロピオン酸アルキル類の生産は上
記均一系触媒を使用する方法、特に上記の■のアルコー
ル類とアクリル酸アルキル類との反応によって行なわれ
ており、反応生成液からの触媒分離操作を行なうことは
避けられない。Therefore, alkyl alkoxypropionates are produced by the method using the above-mentioned homogeneous catalyst, especially by the reaction of alcohols and alkyl acrylates mentioned in (1) above, and the catalyst is separated from the reaction product liquid. That is inevitable.
通常、上記触媒分離操作は、中和或いは濃縮によって、
触媒を固体化した後、濾過機によって分離したり、或い
は目的生成物を含有する液体成分を蒸発缶で加熱蒸発さ
せて触媒と分離する方法が行なわれている。Usually, the above catalyst separation operation involves neutralization or concentration.
After the catalyst is solidified, it is separated using a filter, or a liquid component containing the target product is heated and evaporated in an evaporator to separate it from the catalyst.
しかしながら、ナトリウム系塩基性触媒を使用してアル
コキシプロピオン酸アルキル類を製造するに際し、反応
後の触媒は大部分有機酸のナトリウム塩になり、濃縮す
ると白濁しゾル状になる。However, when producing alkyl alkoxypropionates using a sodium-based basic catalyst, most of the catalyst after the reaction becomes a sodium salt of an organic acid, and when concentrated, it becomes cloudy and forms a sol.
そのため、これを濾過機によって分離する場合、粒子が
微細であるため、メツシュの細かい濾過材が必要になり
、しかも目づまりの頻度も高く、多大の困難を伴い、実
用性が低い。また蒸発缶を用いて加熱蒸発して触媒と分
離する方法は、蒸発濃縮後半期にゾル状物質濃度が上昇
し、流動性が極度に悪化するため、機械撹拌、不活性ガ
スによる撹拌等が非常に困難になり濾過法同様、実用性
が低い。Therefore, when this is separated using a filter, since the particles are fine, a fine mesh filter material is required, and moreover, the filter material frequently gets clogged, which is very difficult and has low practicality. In addition, in the method of heating and evaporating using an evaporator and separating it from the catalyst, the concentration of sol-like substances increases in the latter half of the evaporative concentration, and the fluidity deteriorates extremely, so mechanical stirring, stirring with inert gas, etc. are extremely difficult. As with the filtration method, it is less practical.
さらに、塩基性触媒は反応後、触媒分離操作の前工程と
して中和操作が必要である。Furthermore, after the reaction of the basic catalyst, a neutralization operation is required as a pre-step of the catalyst separation operation.
したがって、アクリル酸アルキル類とアルコール類から
アルコキシプロピオン酸アルキル類を製造するにあたり
、生起する触媒の劣化現象、必要となる廃触媒処理操作
等の困難な問題があり、これらを解決する技術が見当ら
ないのが現状である。Therefore, when producing alkyl alkoxypropionates from alkyl acrylates and alcohols, there are difficult problems such as the deterioration of the catalyst that occurs and the necessary waste catalyst treatment operations, and no technology has been found to solve these problems. is the current situation.
本発明者らは、均一系触媒の宿命である反応後の触媒分
離操作の煩雑さを解決すべく、鋭意研究を行なった結果
、触媒であるナトリウム系塩基性物質は、生成したアル
コキシプロピオン酸アルキル類と反応して容易にアルコ
キシプロピオン酸ナトリウムになこと、そのため、反応
終了時に触媒はナトリウム塩となり、中和操作が不要に
なること、また中和生成物であるアルコキシプロピオン
酸ナトリウムはプロピオン酸ナトリウムに比べて融点が
大幅に低いこと等を知見した。例えば３−エトキシプロ
ピオン酸ナトリウム（触媒相当物質）の融点は１６８℃
、３−エトキシプロピオン酸ナトリウム（触媒相当物質
）の融点は２０６℃である。これら°の温度は通常使用
される加熱蒸発器により容易に得られる温度である。さ
らにこの特性を生かす触媒分離形式を検討し、薄膜式蒸
発機が有効であることを知見した。The present inventors conducted extensive research in order to resolve the complexity of the catalyst separation operation after the reaction, which is the fate of homogeneous catalysts. As a result, the sodium-based basic substance that is the catalyst is Therefore, at the end of the reaction, the catalyst becomes a sodium salt, eliminating the need for neutralization, and the neutralization product, sodium alkoxypropionate, is easily converted into sodium alkoxypropionate. It was found that the melting point was significantly lower than that of For example, the melting point of sodium 3-ethoxypropionate (catalyst equivalent material) is 168℃
, the melting point of sodium 3-ethoxypropionate (catalyst equivalent material) is 206°C. These temperatures are easily obtained by a commonly used heating evaporator. Furthermore, we investigated a catalyst separation method that takes advantage of this characteristic, and found that a thin film evaporator is effective.
本発明は上記の知見に基づいてなされたもので、操作が
容易で、生産効率の高いアルコキシプロピオン酸アルキ
ル類の製造方法を提供することを目的とする。The present invention was made based on the above findings, and an object of the present invention is to provide a method for producing alkyl alkoxypropionates that is easy to operate and has high production efficiency.
上記の目的を達成するため本発明の方法においては、
触媒としてナトリウム系塩基性物質を用い、反応系内の
水分量の当量と使用触媒量の当量との比が０．５〜２．
５の範囲の条件で反応させ、生成液中の触媒相当物質を
、薄膜式蒸発機を用い、触媒相当物質の融点以上の温度
で、蒸発気液分離操作によって反応生成液から分離する
か、或いは、触媒相当物質の融点以下の温度で、蒸発気
固分離操作により反応生成物から分離する。In order to achieve the above object, in the method of the present invention, a sodium-based basic substance is used as a catalyst, and the ratio of the equivalent amount of water in the reaction system to the equivalent amount of the amount of catalyst used is 0.5 to 2.
5, and the catalyst-equivalent substance in the product liquid is separated from the reaction product liquid by vapor-liquid separation operation using a thin-film evaporator at a temperature higher than the melting point of the catalyst-equivalent substance, or , and is separated from the reaction product by evaporation vapor solid separation operation at a temperature below the melting point of the catalyst equivalent material.
アクリル酸アルキル類とアルコール類とを反応させる反
応温度は０〜２００ ”Ｃ１特に５０−１５０℃が好ま
しい。反応圧力は、常圧、加圧、減圧のいずれでもよい
。The reaction temperature for reacting the alkyl acrylates with the alcohol is preferably 0 to 200°C, particularly 50 to 150°C.The reaction pressure may be normal pressure, increased pressure, or reduced pressure.
また、原料アルコール類と、アクリル酸アルキル類の混
合割合は、モル比でｌ：１から１０＝１、特に２：１〜
５：１が好ましい。アルコール類の量が少ないと生成エ
ステル遺択性が下がり、多すぎると未反応アルコールが
増大し共に経済的でない。In addition, the mixing ratio of raw material alcohol and alkyl acrylate is from 1:1 to 10=1 in molar ratio, especially from 2:1 to 1:1.
5:1 is preferred. If the amount of alcohol is too small, the selectivity of the produced ester will be reduced, and if it is too large, the amount of unreacted alcohol will increase, both of which are uneconomical.
触媒として用いられるナトリウム系塩基性物質としては
、公知のナトリウムアルコラード類、水酸化ナトリウム
、酸化ナトリウム等が用いられる。As the sodium-based basic substance used as a catalyst, known sodium alcoholades, sodium hydroxide, sodium oxide, etc. are used.
また反応液中に水分があると、水分によるエステルの加
水分解によって触媒が中和され、活性が低下するので反
応が進まなくなるが、全く水分が存在しなくても反応が
進まないことが判明した。Furthermore, if there is water in the reaction solution, the catalyst is neutralized due to the hydrolysis of the ester by water, reducing its activity and preventing the reaction from proceeding, but it was also found that the reaction did not proceed even in the absence of any water. .
実際の生産においては原料アルコール類、およびアクリ
ル酸アルキル類中には微量の水分は存在するので、水分
が存在する範囲で少ない方が好ましい。In actual production, a trace amount of water is present in raw material alcohols and alkyl acrylates, so it is preferable that the water content be as small as possible.
添加する触媒量は、反応系内の水分当量と添加する触媒
当量の比が０．５〜２．５となるように添加するのが、
分離する触媒量が少なく、かつ反応をスムースに進行さ
せる上から好ましいことが実験的に確認されている。The amount of catalyst to be added is such that the ratio of water equivalent in the reaction system to catalyst equivalent to be added is 0.5 to 2.5.
It has been experimentally confirmed that this method is preferable because the amount of catalyst to be separated is small and the reaction proceeds smoothly.
また、薄膜式蒸発機を用い、廃触媒の融点以上、或いは
融点以下の温度で運転することにより容易かつ連続的に
分離することが可能となる。Furthermore, by using a thin film evaporator and operating at a temperature above or below the melting point of the waste catalyst, it becomes possible to easily and continuously separate the spent catalyst.
反応は、回分式、連続式いずれでもよい。例えば、回分
式ではジャケット付き撹拌槽等、連続式では管式反応器
等が用いられる。The reaction may be carried out either batchwise or continuously. For example, a jacketed stirring tank or the like is used in a batch system, and a tubular reactor or the like is used in a continuous system.
次に実施例、比較例を示して本発明の詳細な説明する。 Next, the present invention will be explained in detail by showing Examples and Comparative Examples.
実施例１
撹拌機および還流冷却器のついた容量５００ｍ１のフラ
スコに、メタノール１６０ｇ、アクリル酸メチル８６ｇ
の混合液を入れた。この混合液の水分は３３０ｐｐｍで
あった。これにナトリウムメチラートの２８％メタノー
ル溶液０．８８ｇを入れ、撹拌しながら昇温し、沸騰温
度で１．０時間反応させた。反応液を分析するとアクリ
ル酸メチルの反応率は９８％、３−メトキシプロピオン
酸メチルの選択率は９８％であり、ナトリウムメチラー
トは存在しなかった。Example 1 In a 500 ml flask equipped with a stirrer and a reflux condenser, 160 g of methanol and 86 g of methyl acrylate were added.
A mixture of these was added. The water content of this liquid mixture was 330 ppm. 0.88 g of a 28% methanol solution of sodium methylate was added to this, the temperature was raised while stirring, and the mixture was reacted at boiling temperature for 1.0 hour. Analysis of the reaction solution revealed that the reaction rate of methyl acrylate was 98%, the selectivity of methyl 3-methoxypropionate was 98%, and no sodium methylate was present.
上記反応をスケールアップして得られた反応液５０ｋｇ
を、伝熱面積が０．３ｍ″の薄膜蒸発機（日立製作新製
、セブコン）を用いて蒸発濃縮した。50 kg of reaction solution obtained by scaling up the above reaction
was evaporated and concentrated using a thin film evaporator (manufactured by Hitachi Seisakusho, Sebcon) with a heat transfer area of 0.3 m''.
薄膜蒸発機の操作条件を第１表に、得られた結果を第２
表に示す。The operating conditions of the thin film evaporator are shown in Table 1, and the obtained results are shown in Table 2.
Shown in the table.
第１表
第２表
実施例２
実施例１と同じ反応液および薄膜蒸発機を用いて、蒸発
濃縮を行なった。廃触媒は底部より固体状で排出された
。Table 1 Table 2 Example 2 Evaporation concentration was carried out using the same reaction solution and thin film evaporator as in Example 1. The spent catalyst was discharged from the bottom in solid form.
薄膜蒸発機の操作条件を第３表に、得られた結果を第４
表に示す
第３表
第４表
比較例１
実施例１にて得られた反応液を、加熱コイル入り蒸発缶
により触媒分離を試みたところ、５０％を留去した時点
で液が白濁ゾル状となり、著しく流動状態が悪化した。The operating conditions of the thin film evaporator are shown in Table 3, and the results obtained are shown in Table 4.
Comparative Example 1 The reaction solution obtained in Example 1 was tried to separate the catalyst using an evaporator equipped with a heating coil, and when 50% of the reaction solution was distilled off, the solution turned into a cloudy sol. As a result, the fluidity deteriorated significantly.
さらに留去を進め、６０％を留去した時点で、突沸現象
が起こり濃縮が不可能になった。Distillation was further continued, and when 60% of the residue was distilled off, a bumping phenomenon occurred and concentration became impossible.
また、撹拌機付きの缶にて同様の操作を行ったが、留去
のスピードを上げると上記と同様の突沸現象が起き、留
去速度を遅くし処理時間を長くする必要が生じ触媒の分
離効率が上がらなかった。In addition, the same operation was performed in a can with a stirrer, but when the speed of distillation was increased, the same bumping phenomenon as above occurred, and it was necessary to slow down the speed of distillation and lengthen the treatment time, resulting in the separation of the catalyst. Efficiency did not increase.
比較例２
実施例１にて得られた反応液を、１ミクロン径の濾紙に
より濾過したところ、ケーキ中に含まれる固形物は２０
％であり残りは分離すべきエステルであった。このため
、ケーキの嵩が太きく（１００ｋｇ反応液あたり１．７
ｋｇ）、またケーキ中に含まれるエステルは廃棄される
ため、経済性が失われた。Comparative Example 2 When the reaction solution obtained in Example 1 was filtered through a filter paper with a diameter of 1 micron, the solid matter contained in the cake was 20
% and the remainder was the ester to be separated. For this reason, the bulk of the cake is large (1.7 kg per 100 kg of reaction liquid).
kg), and the ester contained in the cake was discarded, resulting in loss of economic efficiency.
以上説明したように、本発明のアルコキシプロピオン酸
アルキル類の製造方法は、触媒としてナトリウム系塩基
性物質の適正量を用いて反応させ、薄膜式蒸発機によっ
て生成物を蒸発せしめて廃触媒を分離するので、容易か
つ効率よくアルコキシプロピオン酸アルキル類が得られ
る優れた方法である。As explained above, in the method for producing alkyl alkoxypropionates of the present invention, the reaction is carried out using an appropriate amount of a sodium-based basic substance as a catalyst, the product is evaporated using a thin film evaporator, and the waste catalyst is separated. Therefore, it is an excellent method for obtaining alkyl alkoxypropionates easily and efficiently.
Claims (1)
４）とアルコール類（炭素数は１〜４）とを反応させて
アルコキシプロピオン酸アルキル類を製造するに際し、 触媒としてナトリウム系塩基性物質を用い、反応系内の
水分量の当量と使用触媒量の当量との比が０．５〜２．
５の範囲の条件で反応させ、生成液中の触媒相当物質を
、薄膜式蒸発機を用い、触媒相当物質の融点以上の温度
で、蒸発気液分離操作によって反応生成液から分離する
か、或いは触媒相当物質の融点以下の温度で、蒸発気固
分離操作により反応生成液から分離することを特徴とす
るアルコキシプロピオン酸アルキル類の製造方法。(1) Alkyl acrylates (alkyl has 1 to 1 carbon atoms)
4) and an alcohol (carbon number is 1 to 4) to produce alkyl alkoxypropionates, a sodium-based basic substance is used as a catalyst, and the equivalent amount of water in the reaction system and the amount of catalyst used are The ratio to the equivalent of 0.5 to 2.
5, and the catalyst-equivalent substance in the product liquid is separated from the reaction product liquid by vapor-liquid separation operation using a thin-film evaporator at a temperature higher than the melting point of the catalyst-equivalent substance, or 1. A method for producing alkyl alkoxypropionates, which comprises separating them from a reaction product liquid by an evaporative vapor solid separation operation at a temperature below the melting point of a substance equivalent to a catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2091197A JPH0710805B2 (en) | 1990-04-05 | 1990-04-05 | Method for producing alkyl alkoxypropionate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2091197A JPH0710805B2 (en) | 1990-04-05 | 1990-04-05 | Method for producing alkyl alkoxypropionate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03291255A true JPH03291255A (en) | 1991-12-20 |
| JPH0710805B2 JPH0710805B2 (en) | 1995-02-08 |
Family
ID=14019721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2091197A Expired - Lifetime JPH0710805B2 (en) | 1990-04-05 | 1990-04-05 | Method for producing alkyl alkoxypropionate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0710805B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008260699A (en) * | 2007-04-10 | 2008-10-30 | Hitachi Chem Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONIC ACID ESTER |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102033356B1 (en) * | 2019-07-15 | 2019-10-17 | 재원산업 주식회사 | Method for Refining Alkyl 3-Alkoxy Propionate |
-
1990
- 1990-04-05 JP JP2091197A patent/JPH0710805B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008260699A (en) * | 2007-04-10 | 2008-10-30 | Hitachi Chem Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONIC ACID ESTER |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0710805B2 (en) | 1995-02-08 |
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