JP2943318B2 - Method for producing aliphatic dicarboxylic acid monoester - Google Patents
Method for producing aliphatic dicarboxylic acid monoesterInfo
- Publication number
- JP2943318B2 JP2943318B2 JP2314780A JP31478090A JP2943318B2 JP 2943318 B2 JP2943318 B2 JP 2943318B2 JP 2314780 A JP2314780 A JP 2314780A JP 31478090 A JP31478090 A JP 31478090A JP 2943318 B2 JP2943318 B2 JP 2943318B2
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- acid
- aliphatic dicarboxylic
- mol
- general formula
- 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.)
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Classifications
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- 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
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明は医農薬中間体あるいは化成品中間体として利
用される脂肪族ジカルボン酸モノエステルの製造方法に
関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing an aliphatic dicarboxylic acid monoester used as a pharmaceutical or agricultural chemical intermediate or a chemical intermediate.
＜従来の技術＞ 脂肪族ジカルボン酸とアルコールとを脱水縮合し、モ
ノエステル体を得る場合、目的のモノエステル体以外に
ジエステル体を副生することが知られている。<Prior Art> When an aliphatic dicarboxylic acid and an alcohol are dehydrated and condensed to obtain a monoester, it is known that a diester is produced as a by-product in addition to the intended monoester.
そこでジエステル体の副生をを抑える目的で、アルコ
ールの使用量を少なくすることが考えられるが、その場
合には未反応の脂肪族ジカルボン酸の回収が多くなり、
転化率の大幅な低下が避けられない。かかる方法の改良
的手段として特開昭54−22316においては、ジエステル
の生成を抑制する目的で、アジピン酸ジメチルエステル
を共存させるとともに、当モル以上の水を使用し、酸性
イオン交換樹脂に接触させて、アジピン酸モノメチルエ
ステルを得ている。しかしながら本方法において転化率
が低く、満足できる方法ではなかった。Therefore, in order to suppress the by-product of the diester, it is conceivable to reduce the amount of alcohol used, but in that case, the recovery of the unreacted aliphatic dicarboxylic acid increases,
A significant decrease in conversion is unavoidable. As an improved means of such a method, JP-A-54-22316 discloses that in order to suppress the formation of diester, dimethyl adipate is coexistent, and at least equimolar water is used to contact an acidic ion exchange resin. To obtain adipic acid monomethyl ester. However, in this method, the conversion was low and it was not a satisfactory method.
＜発明が解決しようとする課題＞ 本発明者らは、より効率的な脂肪族ジカルボン酸モノ
エステルの製造方法を検討し、原料である脂肪族ジカル
ボン酸の転化率を高め、副生する脂肪族ジカルボン酸ジ
エステル体の生成を抑え、しかも後の精製も有利に反応
を行う方法を見出し本発明を完成した。<Problems to be Solved by the Invention> The present inventors studied a more efficient method for producing an aliphatic dicarboxylic acid monoester, increased the conversion rate of the aliphatic dicarboxylic acid as a raw material, and produced an aliphatic by-product. The present inventors have found a method for suppressing the production of dicarboxylic acid diesters and performing the reaction in an advantageous manner for the subsequent purification, and completed the present invention.
＜解決するための手段＞ 即ち、本発明は、一般式［II］ HOOC（CH2）mX（CH2）nCOOH ［II］ （式中、ｍおよびｎは１〜４の整数を示し、Ｘは、−CH
2CH2−、−CH＝CH−または−Ｃ≡Ｃ−を示す。但し、Ｘ
が−CH＝CH−または−Ｃ≡Ｃ−であるときはｍ＝ｎであ
る。） で示される脂肪族ジカルボン酸と、一般式［III］ Ｒ−OH ［III］ （式中、Ｒは炭素数１〜６のアルキル基を示す。） で示されるアルコールとを、酸触媒存在下、一般式［I
V］ ROOC（CH2）mX（CH2）nCOOR ［IV］ （式中、ｍ、ｎ、ＸおよびＲは前記と同じ意味を表わ
す。） で示される脂肪族ジカルボン酸ジエステルを共存させ、
実質的に水を使用させずに反応させることを特徴とする
一般式［Ｉ］ ROOC（CH2）mX（CH2）nCOOH ［Ｉ］ （式中、ｍ、ｎ、ＸおよびＲは前記と同じ意味を表わ
す。） で示される脂肪族ジカルボン酸モノエステルの製造方法
に関するものである。<Means for Solving> That is, the present invention has the general formula [II] HOOC (CH 2) m X (CH 2) n COOH [II] ( wherein, m and n represents an integer of 1 to 4, X is -CH
2 CH 2 —, —CH ＝ CH— or —C≡C—. Where X
Is -CH = CH- or -C≡C-, then m = n. ) And an alcohol represented by the general formula [III] R-OH [III] (wherein R represents an alkyl group having 1 to 6 carbon atoms) in the presence of an acid catalyst. , The general formula [I
V] ROOC (CH 2) m X (CH 2) n COOR [IV] ( wherein, m, n, X and R represent. As defined above) are allowed to coexist aliphatic dicarboxylic acid diester represented by,
Formula which comprises reacting without using substantially water [I] ROOC (CH 2) m X (CH 2) n COOH [I] ( wherein, m, n, X and R are the The present invention relates to a method for producing an aliphatic dicarboxylic acid monoester represented by the formula:
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明で使用される一般式〔II〕で示される脂肪族ジ
カルボン酸としては、例えば、アジピン酸、ピメリン
酸、スベリン酸、アゼライン酸、セバシン酸、２−ブテ
ン−1,4−ジカルボン酸、３−ヘキセン−1,6−ジカルボ
ン酸、４−オクテン−1,8−ジカルボン酸、５−デセン
−1,10−ジカルボン酸、２−ブチン−1,4−ジカルボン
酸、３−ヘキシン−1,6−ジカルボン酸、４−オクチン
−1,8−ジカルボン酸、５−デシン−1,10−ジカルボン
酸等を例示することができる。Examples of the aliphatic dicarboxylic acid represented by the general formula [II] used in the present invention include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 2-butene-1,4-dicarboxylic acid, -Hexene-1,6-dicarboxylic acid, 4-octene-1,8-dicarboxylic acid, 5-decene-1,10-dicarboxylic acid, 2-butyne-1,4-dicarboxylic acid, 3-hexyne-1,6 -Dicarboxylic acid, 4-octyne-1,8-dicarboxylic acid, 5-decyne-1,10-dicarboxylic acid and the like.
もう一方の原料である一般式〔III〕で示されるアル
コールとしては、例えば、メタノール、エタノール、ｎ
−プロパノール、イソプロパノール、ｎ−ブタノール、
イソブタノール、ｔ−ブタノール、ｎ−オクタノール、
イソオクタノール、ｎ−ヘキサノール等を例示すること
ができる。The alcohol represented by the general formula [III] as the other raw material includes, for example, methanol, ethanol, n
-Propanol, isopropanol, n-butanol,
Isobutanol, t-butanol, n-octanol,
Examples include isooctanol, n-hexanol and the like.
該アルコール〔III〕の使用量は脂肪族ジカルボン酸
〔II〕１モルに対し、0.7モル以上、1.4モル以下が好ま
しい。The amount of the alcohol [III] used is preferably 0.7 mol or more and 1.4 mol or less per 1 mol of the aliphatic dicarboxylic acid [II].
共存させる一般式〔IV〕で示される脂肪族ジカルボン
酸ジエステルの量は、脂肪族ジカルボン酸〔II〕１モル
に対し、0.3モル以上、1.3モル以下が好ましい。The amount of the aliphatic dicarboxylic acid diester represented by the general formula [IV] to coexist is preferably 0.3 mol or more and 1.3 mol or less based on 1 mol of the aliphatic dicarboxylic acid [II].
本反応においては有機溶媒の使用が有効である。 In this reaction, the use of an organic solvent is effective.
かかる溶媒としては、例えば、トルエン、ベンゼン、
キシレン、クロルベンゼン、ジクロルベンゼン、メチル
エチルケトン、メチルイソブチルケトン、ジクロルエタ
ン、ジオキサン等の芳香族炭化水素、ハロゲン化炭化水
素、ケトン、エーテル類を挙げることができる。Such solvents include, for example, toluene, benzene,
Examples include aromatic hydrocarbons such as xylene, chlorobenzene, dichlorobenzene, methyl ethyl ketone, methyl isobutyl ketone, dichloroethane, and dioxane, halogenated hydrocarbons, ketones, and ethers.
なかでも後処理の点から、原料の脂肪族ジカルボン酸
〔II〕に対し、冷時溶解度の低いものが好ましく、かか
る意味からトルエン、ベンゼン、キシレン、クロルベン
ゼン等の芳香族炭化水素や、ジクロルエタン等のハロゲ
ン化炭化水素が好ましい。Above all, from the viewpoint of post-treatment, those having low solubility in the cold with respect to the aliphatic dicarboxylic acid [II] as the raw material are preferable, and in this sense, aromatic hydrocarbons such as toluene, benzene, xylene, and chlorobenzene, and dichloroethane and the like are preferable. Halogenated hydrocarbons are preferred.
かかる溶媒の使用量は特に制限されないが、通常、原
料の脂肪族ジカルボン酸に対し0.5〜５重量倍程度であ
る。The use amount of such a solvent is not particularly limited, but is usually about 0.5 to 5 times the weight of the raw material aliphatic dicarboxylic acid.
酸触媒としては、例えば、硫酸、トルエンスルホン
酸、メタンスルホン酸、リン酸、塩化水素、硝酸等の無
機または有機の酸が利用されるが、中でも、トルエンス
ルホン酸、硫酸、メタンスルホン酸が好ましい。As the acid catalyst, for example, an inorganic or organic acid such as sulfuric acid, toluenesulfonic acid, methanesulfonic acid, phosphoric acid, hydrogen chloride, or nitric acid is used. Among them, toluenesulfonic acid, sulfuric acid, and methanesulfonic acid are preferable. .
該酸触媒の使用量は通常、原料である脂肪族ジカルボ
ン酸〔II〕に対して0.5〜５重量％の範囲である。The amount of the acid catalyst used is usually in the range of 0.5 to 5% by weight based on the aliphatic dicarboxylic acid [II] as the raw material.
また本発明において、実質的に水を使用せずとは、水
を反応資材として用いないと言う意味であり、全く水が
存在してはならないということではない。従って、脂肪
族ジカルボン酸〔II〕、アルコール〔III〕、脂肪族ジ
カルボン酸ジエステル〔IV〕、酸触媒等中に含まれる比
較的少量の水分は十分許容されるのである。Further, in the present invention, substantially not using water means that water is not used as a reaction material, and does not mean that water must not be present at all. Therefore, a relatively small amount of water contained in the aliphatic dicarboxylic acid [II], the alcohol [III], the aliphatic dicarboxylic acid diester [IV], the acid catalyst and the like is well tolerated.
反応温度は通常、60〜120℃の範囲であり、溶媒の沸
点により適宜定めることができる。The reaction temperature is usually in the range of 60 to 120 ° C, and can be appropriately determined depending on the boiling point of the solvent.
反応時間は特に制限されないが、通常１〜８時間の範
囲である。The reaction time is not particularly limited, but is usually in the range of 1 to 8 hours.
反応終了後、反応混合物からの脂肪族ジカルボン酸モ
ノエステル〔Ｉ〕の単離は、例えば、反応液を冷却し、
未反応の脂肪族ジカルボン酸を結晶として除いたあと、
有機層を濃縮、蒸留してもよいし、有機層をアルカリを
用いて抽出し、水層を酸析後さらに溶媒にて抽出後、濃
縮、蒸留によっても精製できる。After completion of the reaction, the aliphatic dicarboxylic acid monoester [I] is isolated from the reaction mixture by, for example, cooling the reaction solution,
After removing unreacted aliphatic dicarboxylic acid as crystals,
The organic layer may be concentrated and distilled, or the organic layer may be extracted with an alkali, and the aqueous layer may be subjected to acid precipitation and then extracted with a solvent, and then purified by concentration and distillation.
かかる操作により、一般式〔Ｉ〕で示される脂肪族ジ
カルボン酸モノエステルが効率よく得られる。By such an operation, the aliphatic dicarboxylic acid monoester represented by the general formula [I] can be efficiently obtained.
＜発明の効果＞ 本発明により、原料である脂肪族ジカルボン酸〔II〕
の転化率を高め、脂肪族ジカルボン酸ジエステル〔IV〕
の副生を抑えることにより、一般式〔Ｉ〕で示される脂
肪族ジカルボン酸モノエステルが高い収率で、しかも工
業的にも有利に得られる。該脂肪族ジカルボン酸モノエ
ステルは医薬、農薬、添加剤、化成品等の中間体として
有用である。<Effect of the Invention> According to the present invention, aliphatic dicarboxylic acid [II] as a raw material
Of the dicarboxylic acid diester [IV]
By suppressing the by-products, the aliphatic dicarboxylic acid monoester represented by the general formula [I] can be obtained at a high yield and industrially advantageously. The aliphatic dicarboxylic acid monoester is useful as an intermediate for pharmaceuticals, agricultural chemicals, additives, chemical products and the like.
＜実施例＞ 以下、実施例により本発明を更に詳細に説明する。<Example> Hereinafter, the present invention will be described in more detail with reference to examples.
実施例１ ピメリン酸16.02g（0.1mol）、ピメリン酸ジエチルエ
ステル12.97g（0.06mol）、エタノール4.61g（0.1mo
l）、濃硫酸0.32g及びベンゼン32gを加え、撹拌下５時
間還流した。反応終了後、反応液を分析したところ、ピ
メリン酸の消費は86％であり、ピメリン酸モノエステル
の選択率は90％であった。Example 1 16.02 g (0.1 mol) of pimelic acid, 12.97 g (0.06 mol) of pimelic acid diethyl ester, 4.61 g (0.1 mol) of ethanol
l), 0.32 g of concentrated sulfuric acid and 32 g of benzene were added, and the mixture was refluxed for 5 hours with stirring. After the completion of the reaction, the reaction mixture was analyzed to find that the consumption of pimelic acid was 86% and the selectivity for pimelic acid monoester was 90%.
実施例２ スベリン酸17.42g（0.1mol）、スベリン酸ジメチルエ
ステル16.18g（0.08mol）、メタノール2.88g（0.09mo
l）、ｐ−トルエンスルホン酸0.26g及びトルエン40gを
加え、80〜85℃にて７時間加熱撹拌した。反応終了後、
反応液を分析したところ、スベリン酸の消費量は82％で
あり、スベリン酸モノメチルエステルの選択率は93％で
あった。反応液は０〜５℃に冷却し、未反応のスベリン
酸をろ別して除き、ろ液を蒸留にて精製し、後留とし
て、スベリン酸モノメチルエステルを得た。Example 2 Suberic acid 17.42 g (0.1 mol), suberic acid dimethyl ester 16.18 g (0.08 mol), methanol 2.88 g (0.09 mol)
l), 0.26 g of p-toluenesulfonic acid and 40 g of toluene were added, and the mixture was heated and stirred at 80 to 85 ° C for 7 hours. After the reaction,
Analysis of the reaction mixture revealed that the consumption of suberic acid was 82% and the selectivity for monomethyl suberate was 93%. The reaction solution was cooled to 0 to 5 ° C., unreacted suberic acid was removed by filtration, and the filtrate was purified by distillation to obtain suberic acid monomethyl ester as a last fraction.
b.p.133〜135℃/0.5mmHg 実施例３ ３−ヘキセン−1,6−ジカルボン酸17.22g（0.1mo
l）、３−ヘキセン−1,6−ジカルボン酸ジメチルエステ
ル24.03g（0.12mol）、メタノール2.56g（0.08mol）、
濃硫酸0.51g及びトルエン51gを70〜75℃にて８時間加熱
した。反応終了後、反液を分析したところ、３−ヘキセ
ン−1,6−ジカルボン酸の消費量は、73％であり、３−
ヘキセン−1,6−ジカルボン酸モノメチルエステルの選
択率は91％であった。bp 133 to 135 ° C./0.5 mmHg Example 3 17.22 g of 3-hexene-1,6-dicarboxylic acid (0.1 mol
l), 3-hexene-1,6-dicarboxylic acid dimethyl ester 24.03 g (0.12 mol), methanol 2.56 g (0.08 mol),
0.51 g of concentrated sulfuric acid and 51 g of toluene were heated at 70 to 75 ° C. for 8 hours. After the reaction was completed, the reaction solution was analyzed, and the consumption of 3-hexene-1,6-dicarboxylic acid was 73%.
The selectivity for hexene-1,6-dicarboxylic acid monomethyl ester was 91%.
実施例４ ３−ヘキシン−1,6−ジカルボン酸17.02g（0.1mo
l）、３−ヘキシン−1,6−ジカルボン酸ジｎ−プロピル
エステル12.71g（0.05mol）、ｎ−プロパノール8.41g
（0.14mol）、ｐ−トルエンスルホン酸0.34g及びメチル
イソブチルケトン35gを90℃にて６時間加熱した。反応
終了後、反応液を分析すると、３−ヘキシン−1,6−ジ
カルボン酸の消費は91％であり、３−ヘキシン−1,6−
ジカルボン酸モノｎ−プロピルエステルの選択率は80％
であった。Example 4 17.02 g of 3-hexyne-1,6-dicarboxylic acid (0.1 mol
l), 12.71 g (0.05 mol) of 3-hexyne-1,6-dicarboxylic acid di-n-propyl ester, 8.41 g of n-propanol
(0.14 mol), 0.34 g of p-toluenesulfonic acid and 35 g of methyl isobutyl ketone were heated at 90 ° C. for 6 hours. After the reaction was completed, the reaction mixture was analyzed to find that the consumption of 3-hexyne-1,6-dicarboxylic acid was 91%, and that the amount of 3-hexyne-1,6-dicarboxylic acid was 91%.
The selectivity of dicarboxylic mono-n-propyl ester is 80%
Met.
実施例５ セバシン酸20.22g（0.1mol）、セバシン酸ジメチルエ
ステル20.72g（0.09mol）、メタノール2.88g（0.09mo
l）、ｐ−トルエンスルホン酸0.20g及びジクロルエタン
40gを還流下に８時間反応した。反応混合物を分析した
ところ、セバシン酸の添加率は80％であり、セバシン酸
モノメチルエステルの選択率は83％であった。Example 5 Sebacic acid 20.22 g (0.1 mol), sebacic acid dimethyl ester 20.72 g (0.09 mol), methanol 2.88 g (0.09 mol)
l), 0.20 g of p-toluenesulfonic acid and dichloroethane
40 g were reacted under reflux for 8 hours. When the reaction mixture was analyzed, the addition rate of sebacic acid was 80%, and the selectivity for monomethyl sebacate was 83%.
比較例〔実施例２に水を10wt％（対ジカルボン酸）加え
た例〕 スベリン酸17.42g（0.1mol）、スベリン酸ジメチルエ
ステル16.18g（0.08mol）、メタノール2.88g（0.09mo
l）、ｐ−トルエンスルホン酸0.26g及びトルエン40g、
水1.74g（スベリン酸に対し10wt％、0.097mol）を加
え、80〜85℃にて７時間加熱撹拌した。反応終了後、反
応液を分析したところ、スベリン酸の消費量は68％であ
り、スベリン酸モノメチルエステルの選択率は91％であ
った。反応液は０〜５℃に冷却し、未反応のスベリン酸
をろ別して除き、ろ液を蒸留にて精製し、後留として、
スベリン酸モノメチルエステルを得た。Comparative Example [Example in which 10 wt% of water (based on dicarboxylic acid) was added to Example 2] 17.42 g (0.1 mol) of suberic acid, 16.18 g (0.08 mol) of suberic acid dimethyl ester, 2.88 g (0.09 mol) of methanol
l), 0.26 g of p-toluenesulfonic acid and 40 g of toluene,
1.74 g of water (10 wt% based on suberic acid, 0.097 mol) was added, and the mixture was heated and stirred at 80 to 85 ° C. for 7 hours. After the completion of the reaction, the reaction mixture was analyzed. As a result, the consumption of suberic acid was 68%, and the selectivity for suberic acid monomethyl ester was 91%. The reaction solution was cooled to 0 to 5 ° C., unreacted suberic acid was removed by filtration, and the filtrate was purified by distillation.
Suberic acid monomethyl ester was obtained.
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Claims (5)
2CH2−、−CH＝CH−または−Ｃ≡Ｃ−を示す。但し、Ｘ
が−CH＝CH−または−Ｃ≡Ｃ−であるときはｍ＝ｎであ
る。） で示される脂肪族ジカルボン酸と、一般式［III］ Ｒ−OH ［III］ （式中、Ｒは炭素数１〜６のアルキル基を示す。） で示されるアルコールとを、酸触媒存在下、一般式［I
V］ ROOC（CH2）mX（CH2）nCOOR ［IV］ （式中、ｍ、ｎ、ＸおよびＲは前記と同じ意味を表わ
す。） で示される脂肪族ジカルボン酸ジエステルを共存させ、
実質的に水を使用させずに反応させることを特徴とする
一般式［Ｉ］ ROOC（CH2）mX（CH2）nCOOH ［Ｉ］ （式中、ｍ、ｎ、ＸおよびＲは前記と同じ意味を表わ
す。） で示される脂肪族ジカルボン酸モノエステルの製造方法1. A compound of the general formula [II] HOOC (CH 2 ) m X (CH 2 ) n COOH [II] (wherein m and n are integers from 1 to 4, and X is —CH
2 CH 2 —, —CH ＝ CH— or —C≡C—. Where X
Is -CH = CH- or -C≡C-, then m = n. ) And an alcohol represented by the general formula [III] R-OH [III] (wherein R represents an alkyl group having 1 to 6 carbon atoms) in the presence of an acid catalyst. , The general formula [I
V] ROOC (CH 2) m X (CH 2) n COOR [IV] ( wherein, m, n, X and R represent. As defined above) are allowed to coexist aliphatic dicarboxylic acid diester represented by,
Formula which comprises reacting without using substantially water [I] ROOC (CH 2) m X (CH 2) n COOH [I] ( wherein, m, n, X and R are the The method for producing an aliphatic dicarboxylic acid monoester represented by the formula:
肪族ジカルボン酸［II］に対し0.7モル倍以上1.4モル倍
以下である請求項１記載の製造方法。2. The process according to claim 1, wherein the molar ratio of the alcohol [III] used is at least 0.7 mole times and no more than 1.4 mole times with respect to the aliphatic dicarboxylic acid [II].
［IV］のモル比が脂肪族ジカルボン酸［II］に対し0.3
モル倍以上1.3モル倍以下である請求項１または２に記
載の製造方法。3. The molar ratio of the coexisting aliphatic dicarboxylic acid diester [IV] is 0.3 to the aliphatic dicarboxylic acid [II].
3. The production method according to claim 1, wherein the molar ratio is not less than 1.3 times and not more than 1.3 times.
または３に記載の製造方法。4. The method according to claim 1, wherein the reaction is carried out in an organic solvent.
Or the production method according to 3.
ある請求項１、２、３、または４記載の製造方法。5. The method according to claim 1, wherein the acid catalyst is toluenesulfonic acid or sulfuric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314780A JP2943318B2 (en) | 1990-11-19 | 1990-11-19 | Method for producing aliphatic dicarboxylic acid monoester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314780A JP2943318B2 (en) | 1990-11-19 | 1990-11-19 | Method for producing aliphatic dicarboxylic acid monoester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04182452A JPH04182452A (en) | 1992-06-30 |
| JP2943318B2 true JP2943318B2 (en) | 1999-08-30 |
Family
ID=18057506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2314780A Expired - Fee Related JP2943318B2 (en) | 1990-11-19 | 1990-11-19 | Method for producing aliphatic dicarboxylic acid monoester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2943318B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1125808C (en) * | 1996-10-15 | 2003-10-29 | 三菱丽阳株式会社 | Process for preparation of dicarboxylic acid monoesters |
| CN102826998A (en) * | 2012-05-23 | 2012-12-19 | 四川西普化工股份有限公司 | Method for catalyzing synthesizing diisooctyl azelate through load type heteropolyacid |
| CN113880715B (en) * | 2021-10-08 | 2024-02-02 | 万华化学集团股份有限公司 | Purification method for electrochemical synthesis of dimethyl sebacate |
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1990
- 1990-11-19 JP JP2314780A patent/JP2943318B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04182452A (en) | 1992-06-30 |
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