JPS63135347A - Method of reducing content of crude hydroxypivaline aldehyde salt - Google Patents
Method of reducing content of crude hydroxypivaline aldehyde saltInfo
- Publication number
- JPS63135347A JPS63135347A JP62279452A JP27945287A JPS63135347A JP S63135347 A JPS63135347 A JP S63135347A JP 62279452 A JP62279452 A JP 62279452A JP 27945287 A JP27945287 A JP 27945287A JP S63135347 A JPS63135347 A JP S63135347A
- Authority
- JP
- Japan
- Prior art keywords
- water
- crude
- aldolization
- weight
- aqueous phase
- 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
- 238000000034 method Methods 0.000 title claims description 19
- -1 aldehyde salt Chemical class 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
びホルムアルデヒドから塩基を接触的に影響せしめるこ
とによって得られるヒドロキシビバリンアルデヒドから
脱塩する方法に関する。純２、２−ジメチル−１．３−
プロパンジオールまで更に処理するためには、このアル
デヒドをまず水素化しそして得られた水素化バッチを分
留する。２つのその後の処理段階において、塩の存在は
、悪影響を及ぼす。第１の場合には、触媒の被覆および
従って脱活性化を招くことがあり、一方蒸留的操作の場
合にはそれらの存在によって多かれ少なかれ強い生成物
の分解が確認される。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for desalting hydroxybivalaldehyde obtained by catalytically influencing a base from formaldehyde and hydroxybivalaldehyde. Pure 2,2-dimethyl-1,3-
For further processing to propanediol, this aldehyde is first hydrogenated and the resulting hydrogenated batch is fractionated. In the two subsequent processing steps, the presence of salt has an adverse effect. In the first case, this can lead to coating and therefore deactivation of the catalyst, whereas in distillative operations their presence confirms a more or less strong decomposition of the product.
そのような厄介な化合物として、アルドール化触媒自体
ならびに例えば、それらのホルミエート、インブチレー
トまたはヒドロキシピバレートもまた生ずる。後者は、
なかんず（カニツアーロ反応の結果として、または反応
混合物への酸素の作用によって生成する。Aldolization catalysts themselves and, for example, their formate, imbutyrate or hydroxypivalate also occur as such troublesome compounds. The latter is
inter alia (formed as a result of the Cannitzaro reaction or by the action of oxygen on the reaction mixture).
粗製ヒドロキシピバリンアルデヒドの不安定性のゆえに
、文献中では特に、脱塩が粗製２．２−シメチルプロパ
ン−１，３−ジオールの実質的に安定な系に限られてい
る方法が記載されていた。この過程の実質的な欠点は、
水素化触媒の塩被覆によって惹起された活性の変化がそ
のま分離は、ドイツ特許第９６７．５５２号に記載され
ている。ドイツ特許第１，４９８，０４８号の方法によ
れば、薄層蒸発器を用いる前置されたＮＰＣ−粗生成物
の処理が提案される。米国特許
第２，８９５，９９６号の明細書においてそしてドイツ
特許第１，０７６．６５５号の修正された方法によれば
、水素化バッチが塩含有残渣の水蒸気蒸留によって分離
され、そして水性留出物が後続する処理工程において分
離される。粗生成物の共沸蒸留および後続する蒸留は、
米国特許第２，８６５，８１９号に記載されている。特
開昭４４−１０７６７号によれば、水素化バッチは、ま
ず抽出段階において例えばエーテルを用いて前処理され
る。Due to the instability of crude hydroxypivalaldehyde, methods have been described in the literature, in particular, in which desalting is limited to the substantially stable system of crude 2,2-dimethylpropane-1,3-diol. . The practical drawback of this process is that
The isolation of changes in activity caused by salt coating of hydrogenation catalysts is described in German Patent No. 967.552. According to the method of German Patent No. 1,498,048, the treatment of the pretreated NPC crude product using a thin-layer evaporator is proposed. In the specification of US Pat. No. 2,895,996 and according to the modified process of German Patent No. 1,076,655, the hydrogenation batch is separated by steam distillation of the salt-containing residue and the aqueous distillate The materials are separated in subsequent processing steps. The azeotropic distillation of the crude product and the subsequent distillation are
Described in US Pat. No. 2,865,819. According to JP-A-44-10767, the hydrogenation batch is first pretreated in an extraction stage, for example with ether.
これらの方法の欠点は、それらがヒドロキシピバリンア
ルデヒドの不安定性のゆえにネオペンチルグリコールま
で水素化された後に初めて有意義に使用されることがで
き、そして大部分はエネルギーを多用する多段階装置系
を使用した場合に系の外部からの助剤が必要とされる。The disadvantage of these methods is that they can only be meaningfully used after hydrogenation to neopentyl glycol due to the instability of hydroxypivalaldehyde, and most use energy-intensive multi-stage equipment systems. In these cases, auxiliary agents from outside the system are required.
従って、イソブチルアルデヒドおよびホルムアルデヒド
のアルカリ性触媒によるアルドール化の際に得られるも
ののようなヒドロキシピバリンアルデヒドの塩含量の減
少が、系外からの補助物質の添加なしに可能になるよう
な方法に対する関心があった。There is therefore an interest in a process by which a reduction in the salt content of hydroxypivalaldehyde, such as that obtained during the alkaline-catalyzed aldolization of isobutyraldehyde and formaldehyde, is possible without the addition of extraneous auxiliary substances. Ta.
本発明によれば、上記のような課題は、特許請求の範囲
に記載された方法に従って解決される。According to the present invention, the above problems are solved according to the method described in the claims.
イソブチルアルデヒドおよびホルムアルデヒドのアルカ
リ性接触アルドール化の際に得られるもののような約５
ないし１０％の溶解された水含量を有する粗製ヒドロキ
シピバリンアルデヒドの塩含量の減少は、驚くべきこと
には０．５ないし２０重量％、好ましくは２ないし８重
量％の水で処理することによって可能になる。より多量
の水の使用は、なる程可能であるが、同時に望ましくな
い高い生成物の損失を伴なう。About 5
A reduction in the salt content of crude hydroxypivalaldehyde with a dissolved water content of from 1 to 10% is surprisingly possible by treatment with 0.5 to 20% by weight, preferably 2 to 8% by weight of water. become. The use of larger amounts of water is certainly possible, but at the same time is accompanied by undesirably high product losses.
水の添加は、アルドール化に由来する水性相の分離後に
有効に行なわれ、その際配量は１工程で行なうことがで
きる。しかしながら、全部の水の量をいくつかの部分に
細分するのが有利である。それぞれ強力な混合を行なっ
た後にそれぞれの水性相の分離を行なうならば、上記の
方法で同じ水の使用量において明らかにより高い脱塩度
が達成される。The addition of water is advantageously carried out after separation of the aqueous phase resulting from the aldolization, the metering being able to be carried out in one step. However, it is advantageous to subdivide the total amount of water into several parts. If the separation of the respective aqueous phases is carried out after the respective intensive mixing, a clearly higher degree of desalination can be achieved with the above method and with the same amount of water used.
水性相の分離は、従来技術に従って、例えば適当な分離
器内であるいは分離装置の使用によって行なわれる。Separation of the aqueous phase is carried out according to conventional techniques, for example in suitable separators or by the use of separation devices.
これらの分離方法において必要な有機相と水性相との間
の密度の差に基づいて、適当な反応操作により、有機相
の密度が例えば５０℃において１．１ ｇ／ｍｌ、好ま
しくは１．０ ｇ／ｍｌの値を超えないように注意が払
われる。これは、簡単な方法で、例えば、アルドール化
の際の反応の操作によって、例えばイソブチルアルデヒ
ドの反応率の限定あるいはよシ高い過剰量のイソブチル
アルデヒドの添加によりまたは反応バッチに僅かに水溶
性の有機物質、例えば、インブチルアルデヒドおよび／
またはインブタノールを混合することによって行なうこ
とができる。Based on the difference in density between the organic and aqueous phases required in these separation methods, suitable reaction procedures can be used to achieve a density of the organic phase of, for example, 1.1 g/ml at 50° C., preferably 1.0. Care is taken not to exceed the value of g/ml. This can be achieved in simple ways, for example by manipulation of the reaction during the aldolization, e.g. by limiting the conversion of isobutyraldehyde or by adding a higher excess of isobutyraldehyde or by adding slightly water-soluble organic substances, such as inbutyraldehyde and/or
Alternatively, it can be carried out by mixing inbutanol.
反応水から分離されたアルドール化物の混合の際に、一
般に２０ないし７０℃の温度が保たれる。アルドール化
物中に存在する塩の溶解度の減少と共に２０℃以下の低
い温度に調節するための、冷却の形のエネルギーを不必
要にする。During mixing of the aldolide separated from the water of reaction, a temperature of 20 to 70° C. is generally maintained. With the reduction in the solubility of the salts present in the aldolide, energy in the form of cooling is unnecessary to adjust the temperature to lower temperatures below 20°C.
７０℃よシ高い温度に調節する場合には、費用の高い圧
力装置を使用しないならば、例えばイソブチルアルデヒ
ドの高い損失を計算に入れなければならない。When setting temperatures higher than 70.degree. C., high losses of isobutyraldehyde, for example, must be taken into account unless expensive pressure equipment is used.
試験例
０、９６ ｇ／ｍｌの密度および５４０ｐｐｍの塩含量
（Ｎａ０ＯＣＨとして算出）を有する粗製ヒドロキシピ
バリンアルデヒドを室温において下記の表に記載された
量の水と強力に混合する。分離してくる有機相において
、表に記載されている塩含量がギ酸す） ＩＪウムとし
て算出された。Test Example 0 Crude hydroxypivalaldehyde with a density of 96 g/ml and a salt content of 540 ppm (calculated as Na0OCH) is mixed intensively at room temperature with the amount of water specified in the table below. In the organic phase that separates out, the salt content listed in the table is calculated as IJum formic acid.
水の割合（％） 塩含量（ｐｐｍ）
それぞれ比較的少量の水を用いて反復して洗滌し、そし
て水性相を分離することによって上記と同じ生成物から
出発して下記の値が得られた：
２×２％ ４０（ｐｐｒｎ）
３×１％ ９Water percentage (%) Salt content (ppm) The following values were obtained starting from the same product as above by repeated washing with relatively small amounts of water in each case and separation of the aqueous phase. : 2 x 2% 40 (pprn) 3 x 1% 9
Claims (1)
ルカリ性接触アルドール化の際に得られるもののような
粗製ヒドロキシピバリンアルデヒドの塩含量を減少させ
る方法において、アルドール化の後にアルドール化に起
因する水性相を分離し、粗製ヒドロキシピバリンアルデ
ヒドに水０．５ないし２０重量％を添加し、十分に混合
しそして次いで水性相を再度分離することを特徴とする
上記粗製ヒドロキシピバリンアルデヒドの塩含量の減少
方法。 ２、水２ないし８重量％を添加する特許請求の範囲第１
項記載の方法。 ３、水０．５ないし２０重量％または２ないし８重量％
の量を数個の部分に再区分して配合量し、そしてそれぞ
れの添加後に混合しそして次いで水性相を分離する特許
請求の範囲第１項または第２項に記載の方法。 ４、十分な混合を２０ないし７０℃の温度において行な
う特許請求の範囲第１項〜第３項のいずれかに記載の方
法。 ５、アルドール化の際の反応操作によりまたは僅かに水
溶性の有機物質を有機相に添加することによって密度を
最高５０℃において １．１ｇ／ｍｌ、好ましくは最高５０℃において１．０
ｇ／ｍｌに調整する特許請求の範囲第１項〜第４項のい
ずれかに記載の方法。 ６、僅かに水溶性の有機物質としてイソブチルアルデヒ
ドおよび／またはイソブタノールを添加する特許請求の
範囲第１項記載の方法。[Claims] 1. A process for reducing the salt content of crude hydroxypivalaldehyde, such as that obtained during the alkaline catalytic aldolization of isobutyraldehyde and formaldehyde, in which the aqueous phase resulting from the aldolization is removed after the aldolization. The method for reducing the salt content of crude hydroxypivalaldehyde as described above, characterized in that 0.5 to 20% by weight of water is added to the crude hydroxypivalaldehyde, mixed thoroughly and then the aqueous phase is separated off again. 2. Claim 1 in which 2 to 8% by weight of water is added
The method described in section. 3. Water 0.5 to 20% by weight or 2 to 8% by weight
3. A process as claimed in claim 1 or 2, in which the amount is subdivided into several parts and mixed after each addition and then the aqueous phase is separated. 4. The method according to any one of claims 1 to 3, wherein sufficient mixing is carried out at a temperature of 20 to 70°C. 5. By the reaction procedure during the aldolization or by adding slightly water-soluble organic substances to the organic phase, the density is reduced to 1.1 g/ml at max. 50°C, preferably 1.0 at max. 50°C.
The method according to any one of claims 1 to 4, wherein the amount is adjusted to g/ml. 6. The method according to claim 1, wherein isobutyraldehyde and/or isobutanol are added as slightly water-soluble organic substances.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3638168.3 | 1986-11-08 | ||
| DE19863638168 DE3638168A1 (en) | 1986-11-08 | 1986-11-08 | Process for the reduction of the salt content of crude hydroxypivalaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63135347A true JPS63135347A (en) | 1988-06-07 |
Family
ID=6313515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62279452A Pending JPS63135347A (en) | 1986-11-08 | 1987-11-06 | Method of reducing content of crude hydroxypivaline aldehyde salt |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS63135347A (en) |
| DE (1) | DE3638168A1 (en) |
| IT (1) | IT1212045B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017119458A1 (en) * | 2016-01-07 | 2017-07-13 | 三菱瓦斯化学株式会社 | Hydroxypivalaldehyde production method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1793512C3 (en) * | 1968-09-27 | 1987-05-07 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of 2,2-dimethyl-3-hydroxypropanal |
| FR2289478A1 (en) * | 1974-10-30 | 1976-05-28 | Charbonnages Ste Chimique | HYDROXYPIVALDEHYDE PREPARATION PROCESS |
-
1986
- 1986-11-08 DE DE19863638168 patent/DE3638168A1/en active Granted
-
1987
- 1987-11-06 IT IT8748587A patent/IT1212045B/en active
- 1987-11-06 JP JP62279452A patent/JPS63135347A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017119458A1 (en) * | 2016-01-07 | 2017-07-13 | 三菱瓦斯化学株式会社 | Hydroxypivalaldehyde production method |
| CN108463451A (en) * | 2016-01-07 | 2018-08-28 | 三菱瓦斯化学株式会社 | The manufacturing method of hydroxy pivalin aldehyde |
| US10392335B2 (en) | 2016-01-07 | 2019-08-27 | Mitsubishi Gas Chemical Company, Inc. | Method for producing hydroxypivalaldehyde |
| CN108463451B (en) * | 2016-01-07 | 2021-08-13 | 三菱瓦斯化学株式会社 | Method for producing hydroxypivalaldehyde |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3638168A1 (en) | 1988-05-19 |
| IT8748587A0 (en) | 1987-11-06 |
| IT1212045B (en) | 1989-11-08 |
| DE3638168C2 (en) | 1989-01-19 |
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