JPH02233636A - Purification of 2-ethylhexylaldehyde - Google Patents
Purification of 2-ethylhexylaldehydeInfo
- Publication number
- JPH02233636A JPH02233636A JP5340489A JP5340489A JPH02233636A JP H02233636 A JPH02233636 A JP H02233636A JP 5340489 A JP5340489 A JP 5340489A JP 5340489 A JP5340489 A JP 5340489A JP H02233636 A JPH02233636 A JP H02233636A
- Authority
- JP
- Japan
- Prior art keywords
- ethylhexylaldehyde
- ethylbutanol
- hexanol
- mixture containing
- raw material
- 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
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000746 purification Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 21
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims abstract description 16
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims abstract description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006359 acetalization reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 9
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract description 3
- -1 alkenyl ether Chemical compound 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 6
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical group C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- BRMDATNYMUMZLN-UHFFFAOYSA-N Piloty's Acid Chemical compound ONS(=O)(=O)C1=CC=CC=C1 BRMDATNYMUMZLN-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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、２−エチルヘキシルアルデヒドの精製法Ｋ関
する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method K for purifying 2-ethylhexylaldehyde.
更Ｋ詳しくは、本発明は、アセトアルデヒド（以下「Ａ
Ａ」と記す。）とｎ−ブチルアルデヒド（以下「ＢＡ」
と記す。）とのアルドール縮合物の脱水、水添生放物の
一つである、２−エチルヘキシルアルデヒド（以下［２
ＥＨＡＪと記す。）の精製Ｋ関するものである。More specifically, the present invention relates to acetaldehyde (hereinafter referred to as "A").
It is written as "A". ) and n-butyraldehyde (hereinafter referred to as “BA”)
It is written as ) with 2-ethylhexyl aldehyde (hereinafter referred to as [2
It is written as EHAJ. ) is concerned with the purification of K.
２ ｇ ＩＩ Ａを酸化することにより生成するオクチ
ル酸は、可塑剤の原料として、多いＫ用途のあるもので
ある。Octylic acid produced by oxidizing 2 g II A has many uses as a raw material for plasticizers.
ところで、アルカリ存在下ＡＡとＢＡとのアルドール縮
合物の脱水、水添反応を行うと、アルカリの種類、ＡＡ
対ＢＡとのモル比等の違いκより、撞々の割合のアルデ
ヒド類及びアルコール類が生成することが知られている
。主な生成物は、クロトンアルデヒド（ｂｐ：１０４℃
）、２−エチルブチルアルデヒド（ｂｐ：１１フ℃）、
ヘキシルアルデヒド（ｂｐ：１３１℃）、２ＥＨＡ（ｂ
ｐ：１６３℃）、及び水添時、一部副生ずるヘキシルア
ルデヒド、２−エチルプチルアルデヒドの還元物、ヘキ
サノール、２一二チルブタノール（以下それぞれ「ＨＯ
」、「２ Ｅ Ｂ ＯＪと記す。）である。これらの混
合物から、クロトンアルデヒド、ヘキシルアルデヒド、
２−エチルプチルアルデヒドは低沸留分として分離でき
る。しかしＨＯ１２ＥＢＯを分離しようとする時、ＨＯ
と２ＫＢＯは２ＥＩ｛Ａとほとんど沸点差がなく、蒸留
Ｋよって２ＫＨＡｔ高純度化することができない。また
故化工程でこのＩ｛Ｏ、２ＥＢＯが混入したままｇＲＨ
Ａを酸化するとオクチル酸とＨＯ、２ＥＢＯがエステル
を生成し、このエステルがまたオクチル酸と沸点差がな
く、蒸留によってオクチル酸を高純度化できない。By the way, when the aldol condensate of AA and BA is dehydrated and hydrogenated in the presence of an alkali, the type of alkali, AA
It is known that aldehydes and alcohols are produced in different proportions due to the difference in molar ratio κ with BA. The main product is crotonaldehyde (bp: 104℃
), 2-ethylbutyraldehyde (bp: 11°C),
Hexylaldehyde (bp: 131℃), 2EHA (b
p: 163°C), and reduced products of hexylaldehyde and 2-ethylbutyraldehyde, which are partially produced as by-products during hydrogenation, hexanol, and 2-ethylbutanol (hereinafter referred to as "HO
", "2 E B OJ." From these mixtures, crotonaldehyde, hexylaldehyde,
2-Ethylbutyraldehyde can be separated as a low boiling fraction. However, when trying to separate HO12EBO, HO
and 2KBO have almost no difference in boiling point from 2EI{A, and 2KHAt cannot be highly purified by distillation K. In addition, during the aging process, gRH remains mixed with I{O and 2EBO.
When A is oxidized, octylic acid, HO, and 2EBO form an ester, and this ester also has no difference in boiling point from octylic acid, so octylic acid cannot be highly purified by distillation.
本発明は充分ｋ多量の２Ｅ｝ＩＡを含みかつ２ＥＢＯ及
びＨＯを含む混合物から２ＥＨＡを高純度で取得する方
法を提供することである。The present invention provides a method for obtaining 2EHA in high purity from a mixture containing a sufficiently large amount of 2E}IA and also containing 2EBO and HO.
すなわち本発明は充分Ｋ多量の２ＥＨＡを含みかつＨＯ
及び２ＥＢＯを含む混合物にアセタール化触媒を添加し
、前記ＨＯ、２ＥＢＯを２ＥＨＡと反応させ、傅られた
混合物を蒸留することＫより，２ＢＨＡを精製する方法
を要旨とするものである。That is, the present invention contains 2EHA in a sufficiently large amount of K and HO
The gist of the present invention is a method for purifying 2BHA by adding an acetalization catalyst to a mixture containing HO and 2EBO, reacting the HO and 2EBO with 2EHA, and distilling the resulting mixture.
前記２ＥＨＡは、その一部がＨＯ及び２ＥＢＯと反応し
て消費されるのであるから、その消費後？なお残留する
程度に多量でなければならない。Since a part of the 2EHA is consumed by reacting with HO and 2EBO, what happens after its consumption? The amount must be large enough to remain.
前記「充分ｋ多量の」とはその意味を表わす。The phrase "sufficiently large amount" refers to that meaning.
前記２１１ＣＨＡ１１｛０及び２ＥＢＯを含む混合物は
、通常ＡＡとＢＡとのアルドール縮合物を脱■水、水添
することを含む工程を経て得られるものである。The mixture containing 211CHA11{0 and 2EBO is usually obtained through a process including dehydration and hydrogenation of an aldol condensate of AA and BA.
好ましくはＡＡとＢ ．Ａとの７ルドール縮合物を脱水
、水添して得られる混合物を分留して得られる２−エチ
ルヘキシルアルデヒドＫ富んだ留分であ縮合し、アセタ
ール及びアルケ二ルエーテルを生成することである。ま
たその生成物はＧＣ−ＭＳ及びＮＭＲ （プロトン、カ
ーボン１３）Ｋより確認された。Preferably AA and B. A mixture obtained by dehydrating and hydrogenating a 7-rudol condensate with A is condensed with a 2-ethylhexylaldehyde K-rich fraction obtained by fractional distillation to produce an acetal and an alkenyl ether. The product was also confirmed by GC-MS and NMR (proton, carbon-13)K.
前記アセタール化触媒の例としては、硫酸、塩酸、硝酸
、塩化第二鉄、塩化アルｉ＝ウム、塩化亜鉛、塩化カル
シウム、塩化ニッケル、塩化コバルト、陽イオン交換樹
脂、活性白土、モレキュラーシープ、パラトルエンスル
フオン酸、Ｎ−ヒドロキシベンゼンスルフオンアミド、
ナフイオンＮＲ−５０（商標ＤＵＰＯＮＴ製）などを挙
けることができる。またその添加量は、混合物に対して
０．０１〜２０重量チがよい。この添加量より少ないと
活性を示さず、多すぎると２．ＥＨＡの縮合及び積化を
促進し、収率を下げてしま′う。Examples of the acetalization catalyst include sulfuric acid, hydrochloric acid, nitric acid, ferric chloride, aluminum chloride, zinc chloride, calcium chloride, nickel chloride, cobalt chloride, cation exchange resin, activated clay, molecular sheep, and parachloride. Toluenesulfonic acid, N-hydroxybenzenesulfonamide,
Examples include Nafion NR-50 (trademark manufactured by DUPONT). The amount added is preferably 0.01 to 20% by weight relative to the mixture. If the amount added is less than this, no activity will be shown, and if it is too much, 2. This promotes the condensation and accumulation of EHA and lowers the yield.
前記アセタール化反応は−１０〜２００℃で行なうこと
ができる。The acetalization reaction can be carried out at -10 to 200°C.
本発明Ｋおいて、２ＥＨＡとＨＯ及び２ＥＢＯとの反応
と、得られた混合物の蒸留は同時に行なうことが好まし
い。In the present invention K, it is preferable that the reaction of 2EHA with HO and 2EBO and the distillation of the resulting mixture are carried out simultaneously.
以下Ｋ実施例を掲げて本発明を具体的Ｋ説明する。 The present invention will be specifically explained below with reference to Examples.
尚、以下の例Ｋおいて組成はすべてガスクロマトダラム
の面積一で表わす。このガスクロマトグラフィーの条件
は次のとおりである。In Example K below, all compositions are expressed in terms of the area of the gas chromatograph. The conditions for this gas chromatography are as follows.
カラム： Ｓｉｌｉｃｏｎｅ − ＫＦ ９６ （商標
）（２０％）、カラム長＝２罵、温度：７０〜１５０℃
（８℃／ｍｉｎ ）、キャリアーガス： Ｈｅ （ １
＃ ／ ” ） 、検出器： Ｆ Ｉ Ｄ ｏ
夾施例１
粗２ＥＨＡ （組成、２ＩＣＨＡ：９２，０％、２ＥＢ
Ｏ：５．０％、ＨＯ：３．０％）、５００ｆＫ塩化第二
鉄０．５ Ｆ （粗２ＥＨＡＫ対し−（ ０．１重量％
）を加えて、５ｗｌＨｆの減圧下、で、単蒸留を行い、
ＺＥＨＡを留出した結果、液組成が２ＥＨＡ ：９８．
５チ、ＨＯ：０．４チ、２ＥＢＯ：０，６％の留分４４
５ｆが得られた。２Ｅ｝｛Ａの回収率は９５一であった
。Column: Silicone-KF 96 (trademark) (20%), column length = 2 mm, temperature: 70-150°C
(8℃/min), carrier gas: He (1
# / ” ), Detector: F I D o Example 1 Crude 2EHA (Composition, 2ICHA: 92.0%, 2EB
O: 5.0%, HO: 3.0%), 500 fK ferric chloride 0.5 F (relative to crude 2EHAK - (0.1% by weight)
) and perform simple distillation under reduced pressure of 5 wlHf.
As a result of distilling ZEHA, the liquid composition was 2EHA:98.
5chi, HO: 0.4chi, 2EBO: 0.6% fraction 44
5f was obtained. 2E}{The recovery rate of A was 95-1.
比較例１
粗２ＥＨＡ（組成、２Ｅ｝ＩＡ：９２．０％、２ＥＢＯ
：５．０チ、｝ＩＱ：３，０％）、５００Ｆを、５ｍｍ
｝ｉｆの減圧下で、単蒸留を行い、初留ｌＯ−をカット
した結果、液組成が２ＥＨＡ：９２．５％、２ＥＢＯ：
４．８％、ＨＯ：２．７＄１７）留分４３８ｔが得られ
た。Comparative Example 1 Crude 2EHA (composition, 2E}IA: 92.0%, 2EBO
:5.0chi, }IQ:3.0%), 500F, 5mm
}If, simple distillation was performed under reduced pressure and the initial distillate 1O- was cut, the liquid composition was 2EHA:92.5%, 2EBO:
4.8%, HO: 2.7$17) 438t of fraction was obtained.
本発明によれば、充分Ｋ多量の２１｝ＩＡを含みかつ２
ＥＢＯ及びＨＯを含む混合物から２ＥＨＡを高純度で得
ることができる。According to the present invention, it contains a sufficiently large amount of 21}IA and 2
2EHA can be obtained in high purity from a mixture containing EBO and HO.
Claims (4)
みかつ２−エチルブタノール及びヘキサノールを含む混
合物に、アセタール化触媒を混合し、前記２−エチルブ
タノール及びヘキサノールを２−エチルヘキシルアルデ
ヒドと反応させ、得られた混合物を蒸留することを特徴
とする２−エチルヘキシルアルデヒドの精製方法。(1) An acetalization catalyst is mixed with a mixture containing a sufficiently large amount of 2-ethylhexylaldehyde and 2-ethylbutanol and hexanol, and the 2-ethylbutanol and hexanol are reacted with 2-ethylhexylaldehyde. 1. A method for purifying 2-ethylhexylaldehyde, which comprises distilling a mixture of 2-ethylhexylaldehyde.
ブタノール及びヘキサノールを含む混合物が、アセトア
ルデヒドとｎ−ブチルアルデヒドとのアルドール縮合物
を脱水、水添することを含む工程を経て得られる混合物
であることを特徴とする請求項（１）に記載の方法。(2) The mixture containing 2-ethylhexylaldehyde, 2-ethylbutanol and hexanol is a mixture obtained through a process including dehydrating and hydrogenating an aldol condensate of acetaldehyde and n-butyraldehyde. The method according to claim (1), characterized in that:
ブタノール及びヘキサノールを含む混合物がアセトアル
デヒドとｎ−ブチルアルデヒドとのアルドール縮合を脱
水、水添して得られる混合物を分留して得られる２−エ
チルヘキシルアルデヒドに富んだ留分であることを特徴
とする請求項（２）に記載の方法。(3) 2-ethylhexylaldehyde obtained by fractionating the mixture containing 2-ethylhexylaldehyde, 2-ethylbutanol and hexanol obtained by dehydrating and hydrogenating aldol condensation of acetaldehyde and n-butyraldehyde. The method according to claim 2, characterized in that the fraction is enriched in .
ルヘキシルアルデヒド、２−エチルブタノール及びヘキ
サノールを含む混合物に対して０．０１〜２０重量％と
することを特徴とする、請求項（１）ないし（３）のい
ずれかに記載の方法。(4) Claim (1) characterized in that the amount of the acetalization catalyst added is 0.01 to 20% by weight based on the mixture containing 2-ethylhexylaldehyde, 2-ethylbutanol, and hexanol. The method described in any one of to (3).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5340489A JPH02233636A (en) | 1989-03-06 | 1989-03-06 | Purification of 2-ethylhexylaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5340489A JPH02233636A (en) | 1989-03-06 | 1989-03-06 | Purification of 2-ethylhexylaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02233636A true JPH02233636A (en) | 1990-09-17 |
Family
ID=12941892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5340489A Pending JPH02233636A (en) | 1989-03-06 | 1989-03-06 | Purification of 2-ethylhexylaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02233636A (en) |
-
1989
- 1989-03-06 JP JP5340489A patent/JPH02233636A/en active Pending
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