JPS63246343A - Purification of higher alcohol - Google Patents
Purification of higher alcoholInfo
- Publication number
- JPS63246343A JPS63246343A JP8027887A JP8027887A JPS63246343A JP S63246343 A JPS63246343 A JP S63246343A JP 8027887 A JP8027887 A JP 8027887A JP 8027887 A JP8027887 A JP 8027887A JP S63246343 A JPS63246343 A JP S63246343A
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- acid
- aqueous solution
- distillation
- distilling
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000000746 purification Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000001298 alcohols Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 238000009835 boiling Methods 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 abstract description 18
- 239000002994 raw material Substances 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 8
- 239000000047 product Substances 0.000 abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007769 metal material Substances 0.000 abstract description 3
- 239000004711 α-olefin Substances 0.000 abstract description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001630 malic acid Substances 0.000 abstract description 2
- 235000011090 malic acid Nutrition 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000007037 hydroformylation reaction Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は高級アルコールの精製方法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a method for purifying higher alcohols.
詳しくは、本発明は炭素数6以上の粗製アルコールを蒸
留精製するにあたり、副生物の生成を抑制する方法に関
するものである。Specifically, the present invention relates to a method for suppressing the production of by-products when distilling and purifying crude alcohols having 6 or more carbon atoms.
剤
可塑剤、洗1等の原料として用いられる高級アルコール
は主としてチーグラー法、オキソ法及びパラフィン酸化
法の3種の方法で工業的に製造されている。これらの高
級アルコールのうち、炭素数io以下のものは可塑剤原
料に、また炭素数io以上のものは洗剤原料に、主な用
途がある。これら高級アルコールの製造工程においては
通常、蒸留による分離精製が行なわれる。Higher alcohols used as raw materials for plasticizers, detergents, etc. are industrially produced mainly by three methods: the Ziegler method, the oxo method, and the paraffin oxidation method. Among these higher alcohols, those having less than io carbon atoms are mainly used as plasticizer raw materials, and those having more than io carbon atoms are mainly used as detergent raw materials. In the production process of these higher alcohols, separation and purification by distillation is usually performed.
例えばオキン法アルコールの場合には、オキソ反応の段
階で直鎖型及び分岐型のものが、反応条件によるが、通
常/:0.I−/の範囲の比率で生成する。用途にもよ
るが、通常直鎖型の方が需要が大きいので、減圧蒸留に
よって直鎖型と分岐型とを分離することがよく行なわれ
ている。For example, in the case of oxine process alcohols, linear and branched types are separated at the oxo reaction stage depending on the reaction conditions, but usually /:0. It is produced at a ratio in the range of I-/. Although it depends on the application, the linear type is usually in greater demand, so it is common practice to separate the linear type and the branched type by vacuum distillation.
また上記以外にも、第一級アルコールを脱水縮合して分
岐型の三量化アルコールを得るゲルベ法において、生成
アルコールを水洗処理した後、減圧蒸留して三量化アル
コールを分離取得することが行なわれる。In addition to the above, in the Guerbet process for obtaining branched trimerized alcohols by dehydration condensation of primary alcohols, the produced alcohol is washed with water and then distilled under reduced pressure to separate and obtain the trimerized alcohols. .
上記オキン法アルコールまたは三量化アルコール等を蒸
留精製するに際し、特に炭素数が6以上の高級アルコー
ルの場合には、蒸留中に高級アルコールが副反応を起こ
し、副生物、例えばアルデヒド、オレフィン、高沸点副
生物などの生成が著しく増加し、製品アルコールの純度
の低下をきたすばかりでなく、収得率が著しく減少する
という問題点があった。When distilling and refining the above-mentioned Okin method alcohol or trimerized alcohol, etc., especially in the case of higher alcohols having 6 or more carbon atoms, the higher alcohols undergo side reactions during distillation, resulting in by-products such as aldehydes, olefins, and high-boiling point alcohols. There is a problem in that the production of by-products and the like increases significantly, which not only causes a decrease in the purity of the product alcohol, but also significantly reduces the yield.
〔問題点を解決するための手段〕
本発明者らは上記高級アルコールの蒸留時の問題点を解
決すべく鋭意検討を重ねた結果、上記蒸留時の副反応は
高級アルコール中の微量の不純物の作用に基づくもので
あり、原料高級アルコールを特定の態様で酸と接触させ
て蒸留精製することによシ上記不純物の作用が有効に抑
制され、蒸留時の上記副生物の生成量が著しく減少する
ことを見出して本発明を完成した。[Means for Solving the Problems] The present inventors have made extensive studies to solve the problems during distillation of higher alcohols, and have found that the side reactions during distillation are due to trace amounts of impurities in higher alcohols. By bringing the raw material higher alcohol into contact with acid in a specific manner and purifying it by distillation, the effects of the above impurities can be effectively suppressed, and the amount of by-products produced during distillation can be significantly reduced. They discovered this and completed the present invention.
即ち本発明の要旨は、炭素数を以上の粗製アルコールを
蒸留によって精製するに当り、該アルコールを酸水溶液
で洗浄した後又は酸の存在下に蒸留することを特徴とす
る高級アルコールの精製方法、に存する。That is, the gist of the present invention is to provide a method for purifying higher alcohols, which is characterized in that, in purifying crude alcohols having a carbon number or more by distillation, the alcohols are washed with an aqueous acid solution or distilled in the presence of an acid; exists in
以下、本発明について詳細に説明する。The present invention will be explained in detail below.
本発明の精製方法の対象とする高級アルコール(以下、
原料アルコールという)は炭素数6以上のアルコールで
あり、好ましくは炭素数り〜30のアルコール、より好
ましくは炭素数7〜20のアルコールである。原料アル
コールの由来(製法)は特に限定されず、チーグラー法
アルコール、オキソ法アルコール、パラフィン酸化法ア
ルコール或いはゲルベ法アルコールのいずれも用いるこ
とができる。実用的には特にチーグラー法エチレン低重
合によって得られるα−オレフィン、あるいはワックス
分解により得られるα−オレフィンをヒドロホルミル化
反応及び水添反応して得られるオキソ法アルコール、或
いは第1級アルコールをアルカリまたはアルカリと助触
媒との共存下に脱水縮合反応させ、得られる分岐型の三
量化アルコールを水洗して触媒を除去して得られるゲル
ベ法アルコール等に本発明方法を適用するのが好適であ
る。Higher alcohols (hereinafter referred to as
The raw material alcohol) is an alcohol having 6 or more carbon atoms, preferably an alcohol having 3 to 30 carbon atoms, and more preferably an alcohol having 7 to 20 carbon atoms. The origin (manufacturing method) of the raw material alcohol is not particularly limited, and any of Ziegler process alcohol, oxo process alcohol, paraffin oxidation process alcohol, or Guerbet process alcohol can be used. Practically, in particular, alpha-olefins obtained by Ziegler method ethylene low polymerization, or alpha-olefins obtained by wax decomposition, are hydroformylated and hydrogenated to produce oxo-method alcohols, or primary alcohols are treated with alkali or It is suitable to apply the method of the present invention to Guerbet process alcohols, etc., which are obtained by carrying out a dehydration condensation reaction in the presence of an alkali and a co-catalyst, and washing the resulting branched trimerized alcohol with water to remove the catalyst.
本発明方法においては原料アルコールを酸水溶液で洗浄
した後に蒸留するか又は酸の存在下に蒸留する。In the method of the present invention, raw alcohol is washed with an aqueous acid solution and then distilled, or distilled in the presence of an acid.
上記酸水溶液としては無機酸又は有機酸の水溶液が用い
られる。上記無機酸としては通常、硫酸、塩酸、硝酸等
の強酸が用いられる。無機酸水溶液としては通常、pH
が2〜6、好ましくは3〜!のものが用いられる。上記
有機酸としては通常、 pKa1〜6、好ましくはλ
〜!のものが用いられ、例えば酢酸、リンゴ酸、クエン
酸等があげられる。有機酸水溶液としても通常、pHが
λ〜乙の範囲のものを用いるのが好ましい。上記pH又
はpKaが小さ過ぎる場合には処理装置の金属材質の腐
食が増大し、また逆に大き過ぎる場合には酸洗浄の効果
が小さくなるO
酸水溶液による洗浄処理の方式は特に限定されず、連続
式、半連続式、バッチ式のいずれでもよい。As the acid aqueous solution, an inorganic or organic acid aqueous solution is used. As the inorganic acid, strong acids such as sulfuric acid, hydrochloric acid, and nitric acid are usually used. As an inorganic acid aqueous solution, the pH is usually
is 2-6, preferably 3-! are used. The above organic acid usually has a pKa of 1 to 6, preferably λ
~! For example, acetic acid, malic acid, citric acid, etc. are used. It is usually preferable to use an organic acid aqueous solution having a pH in the range of λ to B. If the above pH or pKa is too small, the corrosion of the metal material of the processing equipment will increase, and if it is too large, the acid cleaning effect will be reduced. It may be a continuous type, a semi-continuous type, or a batch type.
酸水溶液/原料アルコールの容量比は通常、1)、//
1〜to/i、好ましくは0.5// P−ra/ の
範囲とする。The volume ratio of acid aqueous solution/raw alcohol is usually 1), //
The range is 1 to/i, preferably 0.5//P-ra/.
酸水溶液で洗浄した原料アルコールは次いで蒸留するこ
とによって精製する。The raw alcohol washed with the acid aqueous solution is then purified by distillation.
本発明方法においては原料アルコールを酸の存在下に蒸
留することによっても同様に前記副反応を抑制すること
ができる。核酸としては原料アルコールと共に留出して
製品を汚染せず、また蒸留釜の金属材質を腐食しないよ
うな高沸点の酸を用いることができる。In the method of the present invention, the side reactions can be similarly suppressed by distilling the raw alcohol in the presence of an acid. As the nucleic acid, an acid with a high boiling point that does not contaminate the product by distilling out together with the raw alcohol and does not corrode the metal material of the distillation pot can be used.
蒸留は目的とする成分が分離可能な理論段数を有する蒸
留塔を用いて、釜温が通常、2!0°C以下、望ましく
は2θO℃以下となるように減圧度を調節して行なう。Distillation is carried out using a distillation column having a number of theoretical plates capable of separating the target components, and by adjusting the degree of vacuum so that the pot temperature is usually 2!0°C or less, preferably 2θ0°C or less.
釜温が2jtO℃以上では副生成物(アルデヒド、オレ
フィン及び高沸点副生物)の生成量が増加する。When the pot temperature is 200° C. or higher, the amount of byproducts (aldehydes, olefins, and high-boiling point byproducts) increases.
次に本発明の実施の態様を実施例によってさらに具体的
に説明するが、本発明はその要旨を越えない限り、以下
の実施例によって限定されるものではない。Next, embodiments of the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless the gist thereof is exceeded.
比較例/
攪拌器、温度計、窒素導入管及びサンプリング口を持つ
容積300rttlの四ツロフラスコに、炭素数りの直
鎖状アルコールをアルカリ触媒の存在下に脱水縮合して
得られたイソステアリルアルコールを水洗処理したもの
を/jOrttl仕込み、230′Cまで昇温し、到達
した時点から、逐次サンプリングを行ないガスクロマト
グラフィー分析によって、アルデヒド、オレフィン、高
沸物の含有量の変化を調べた。Comparative Example / Isostearyl alcohol obtained by dehydration condensation of a linear alcohol with the same number of carbon atoms in the presence of an alkali catalyst was placed in a 300 rttl four-tube flask equipped with a stirrer, a thermometer, a nitrogen inlet tube, and a sampling port. The water-washed product was charged to /jOrttl, heated to 230'C, and from that point on, sampling was performed successively and changes in the contents of aldehydes, olefins, and high-boiling substances were investigated by gas chromatography analysis.
その結果は第1図に実線で示した。いずれも時間に対し
指数関数で増加減していることから、生成物に対し1次
であることが判る。そして、特に、加熱処理r時間後に
極立った増加現象が現われその後は反応でつぶれて行く
パターンを示した。特に高沸物については大幅に増加し
、かかる条件で蒸留すれば製品取得率が減少することが
判る。The results are shown in FIG. 1 as a solid line. Since both increase and decrease exponentially with respect to time, it can be seen that they are linear with respect to the product. In particular, a pattern was shown in which a remarkable increase occurred after r hours of heat treatment, and thereafter it collapsed due to the reaction. In particular, high-boiling substances significantly increase, and it can be seen that the product yield rate decreases if distilled under such conditions.
実施例1
比較例1と同様の装置を用い、クエン酸の0.2%水溶
液で比較例1で用いた原料イソステアリルアルコールと
同一のものを容量比i /lの割合で洗浄した後に、比
較例1と同様の実験を行なった結果を第1図に破線で示
した。Example 1 Using the same apparatus as in Comparative Example 1, the same raw material isostearyl alcohol used in Comparative Example 1 was washed with a 0.2% aqueous solution of citric acid at a volume ratio of i/l. The results of an experiment similar to Example 1 are shown in FIG. 1 by broken lines.
アルデヒド、オレフィン、高沸物ともに生成が抑制され
ており、高沸物の生成量も小さくかかる条件で蒸留を行
なった場合の製品取得率も向上することが明らかである
。It is clear that the production of aldehydes, olefins, and high-boiling substances is suppressed, and the amount of high-boiling substances produced is also small, and the product yield is improved when distillation is carried out under such conditions.
実施例2
C,アルコールから ゲルベ反応によって合成したイン
ステアリルアルコールを触媒であるアルカリを除去する
ため水洗を2回実施し、その後クエン酸(O0S%)水
溶液でl:lの容積比で洗浄したものを、充填塔付きの
回分蒸留器で圧力J(7WHg の条件で蒸留した結
果を第2図に示す。釜温度は第2図に示す通9220℃
〜210℃の範囲である。Example 2 Instearyl alcohol synthesized from C, alcohol by Guerbet reaction was washed twice with water to remove the alkali catalyst, and then washed with a citric acid (00S%) aqueous solution at a volume ratio of 1:1. is distilled in a batch distiller equipped with a packed column under the conditions of pressure J (7 WHg).The results of the distillation are shown in Figure 2.
It is in the range of ~210°C.
比較例コ
実施例2と同条件であるが、クエン酸洗浄の代りに、更
に水洗浄を実施したときのものの結果を第2図に示す。Comparative Example The results were shown in FIG. 2 under the same conditions as Example 2, but with water washing instead of citric acid washing.
〔発明の効果〕
本発明方法によシ蒸留時の副反応による副生物の生成を
効果的に抑制しつつ高級アルコールを精製することがで
きる。[Effects of the Invention] According to the method of the present invention, higher alcohols can be purified while effectively suppressing the production of byproducts due to side reactions during distillation.
第1図は実施例1及び比較例1における加熱処理試験の
結果を示す。(縦軸の不純物濃度は対数目盛である。)
第2図は実施例コ及び比較例コにおける蒸留試験の結果
を示す。(左側縦軸の不純物濃度は対数目盛である。)
特許出願人 三菱化成工業株式会社
代 理 人 弁理士 長谷用 −
ほか1名
あ 1 図
10熱%理埒間(時間)
あ2品
ctX、i18李(z)FIG. 1 shows the results of heat treatment tests in Example 1 and Comparative Example 1. (The impurity concentration on the vertical axis is on a logarithmic scale.) FIG. 2 shows the results of the distillation test in Example C and Comparative Example C. (The impurity concentration on the left vertical axis is on a logarithmic scale.) Patent applicant: Mitsubishi Chemical Industries, Ltd. Agent: Patent attorney: Hase - 1 other person 1 Figure 10 Heat % Rikenma (time) A 2 items ctX, i18 Lee (z)
Claims (4)
製するに当り、該アルコールを酸水溶液で洗浄した後又
は酸の存在下に蒸留することを特徴とする高級アルコー
ルの精製方法。(1) A method for purifying higher alcohols, which comprises distilling a crude alcohol having 6 or more carbon atoms by washing the alcohol with an aqueous acid solution or in the presence of an acid.
精製方法において、上記アルコールをpH2〜6の無機
酸水溶液で洗浄した後に蒸留することを特徴とする方法
。(2) A method for purifying a higher alcohol according to claim 1, which comprises washing the alcohol with an aqueous inorganic acid solution having a pH of 2 to 6 and then distilling it.
精製方法において、上記アルコールをpKa1〜6の有
機酸の水溶液で洗浄したのちに蒸留することを特徴とす
る方法。(3) A method for purifying a higher alcohol according to claim 1, characterized in that the alcohol is washed with an aqueous solution of an organic acid having a pKa of 1 to 6 and then distilled.
精製方法において、上記アルコールを高沸点の酸の存在
下に蒸留することを特徴とする方法。(4) A method for purifying a higher alcohol according to claim 1, which comprises distilling the alcohol in the presence of a high-boiling acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8027887A JPH0753676B2 (en) | 1987-04-01 | 1987-04-01 | Purification method for high-grade alcohol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8027887A JPH0753676B2 (en) | 1987-04-01 | 1987-04-01 | Purification method for high-grade alcohol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63246343A true JPS63246343A (en) | 1988-10-13 |
JPH0753676B2 JPH0753676B2 (en) | 1995-06-07 |
Family
ID=13713806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8027887A Expired - Lifetime JPH0753676B2 (en) | 1987-04-01 | 1987-04-01 | Purification method for high-grade alcohol |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0753676B2 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9447018B2 (en) | 2009-10-20 | 2016-09-20 | Greenyug, Llc | Ethyl acetate production |
WO2014130465A1 (en) * | 2013-02-19 | 2014-08-28 | Greenyug, Llc | Production of higher alcohols |
-
1987
- 1987-04-01 JP JP8027887A patent/JPH0753676B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH0753676B2 (en) | 1995-06-07 |
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Legal Events
Date | Code | Title | Description |
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EXPY | Cancellation because of completion of term |