JPH04149149A - Method for separating and purifying tetracarboxylic acid - Google Patents
Method for separating and purifying tetracarboxylic acidInfo
- Publication number
- JPH04149149A JPH04149149A JP27482890A JP27482890A JPH04149149A JP H04149149 A JPH04149149 A JP H04149149A JP 27482890 A JP27482890 A JP 27482890A JP 27482890 A JP27482890 A JP 27482890A JP H04149149 A JPH04149149 A JP H04149149A
- Authority
- JP
- Japan
- Prior art keywords
- naphthalenetetracarboxylic acid
- solvent
- acid
- mixture
- propanol
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 150000000000 tetracarboxylic acids Chemical class 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 17
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 6
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical compound [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 claims 1
- 229940044613 1-propanol Drugs 0.000 claims 1
- 238000010923 batch production Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract description 9
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000004642 Polyimide Substances 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920001721 polyimide Polymers 0.000 abstract description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- -1 naphthalenetetracarboxylic acid alkali salts Chemical class 0.000 description 4
- 238000006462 rearrangement reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003916 acid precipitation Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 2
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YNEALOKCGKJTAX-UHFFFAOYSA-L disodium;naphthalene-1,2-dicarboxylate Chemical compound [Na+].[Na+].C1=CC=CC2=C(C([O-])=O)C(C(=O)[O-])=CC=C21 YNEALOKCGKJTAX-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、２，３．６．７−ナフタレンテトラカルボン
酸を各種ナフタレンカルボン酸の混合物より分離・精製
する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for separating and purifying 2,3,6,7-naphthalenetetracarboxylic acid from a mixture of various naphthalenecarboxylic acids.
ナフタレンを基本骨格とし、ナフタレンの２．３゜６．
７−位にカルボキシル基の置換した２、３，６．７−ナ
フタレンテトラカルボン酸は、高機能性ポ゛リエステル
、高機能性ポリイミド等の高機能性有機材Ｈの原料とし
て注目されるものである。本出願人も、ナフタレンモノ
カルボン酸塩等を原料とし、２，３゜６．７−ナフタレ
ンテトラカルボン酸及びそのテトラナトリウム塩、テト
ラカリウム塩などをヘンケル転位反応により合成する方
法について特許を出願している（特開平２−６９４３３
号公報、特開平２−６９４３４号公報）。Naphthalene is the basic skeleton, and naphthalene's 2.3°6.
2,3,6,7-naphthalenetetracarboxylic acid substituted with a carboxyl group at the 7-position is attracting attention as a raw material for highly functional organic materials H such as highly functional polyesters and highly functional polyimides. be. The applicant has also applied for a patent on a method for synthesizing 2,3゜6,7-naphthalenetetracarboxylic acid and its tetrasodium salt, tetrapotassium salt, etc. by Henkel rearrangement reaction using naphthalene monocarboxylate as a raw material. (Unexamined Japanese Patent Publication No. 2-69433)
(Japanese Patent Application Laid-open No. 2-69434).
上述したヘンケル転位反応で２．３，６．７−ナフタレ
ンテトラカルボン酸を合成する方法は、生成物中にナフ
タレンテトラカルボン酸の他、ナフタレンモノカルボン
酸、ナフタレンジカルボン酸およびナフタレントリカル
ボン酸などのアルカリ塩が多く含まれ、ナフタレンテト
ラカルボン酸の含有量が必ずしも高くない場合もある。The method of synthesizing 2,3,6,7-naphthalenetetracarboxylic acid by the above-mentioned Henkel rearrangement reaction is based on the method of synthesizing 2,3,6,7-naphthalenetetracarboxylic acid in the product. It may contain a lot of salt and the content of naphthalenetetracarboxylic acid may not necessarily be high.
したがって、２，３，６．７−ナフタレンテトラカルボ
ン酸を各種のナフタレンカルボン酸より選択的ニ分翻す
る必要があったが、従来の再結晶法等では高収率かつ高
純度に精製することができなかった。Therefore, it was necessary to selectively split 2,3,6.7-naphthalenetetracarboxylic acid from various naphthalenecarboxylic acids, but conventional recrystallization methods cannot purify it to high yield and high purity. I couldn't do it.
ところで、２，６−ナフタレンジカルボン酸、２，７ナ
フタレンジカルボン酸をはじめとするナフタレンポリカ
ルボン酸類は、高機能性樹脂等の原料とじて注目される
ものであり、芳香環中の互いに５員環酸無水物を形成で
きる位置に４個のカルボキシル基を有する化合物では、
ヘンゼン環を含むピロメリット酸が主としてデュレンよ
り合成されており、その分離・精製法はずでＱこ確立さ
れている。By the way, naphthalene polycarboxylic acids such as 2,6-naphthalene dicarboxylic acid and 2,7-naphthalene dicarboxylic acid are attracting attention as raw materials for high-performance resins, etc., and they have five-membered rings in their aromatic rings. In compounds having four carboxyl groups at positions where acid anhydrides can be formed,
Pyromellitic acid containing a Hensen ring is mainly synthesized from Durene, and a method for its separation and purification has been established.
しかし、２，３，６．７−ナフタレンテトラカルボン酸
の分離・生成法に関しては、現在までのところ何ら有効
な提案はなされていなかった。However, no effective proposal has been made so far regarding a method for separating and producing 2,3,6,7-naphthalenetetracarboxylic acid.
本発明は、以上の点に鑑みてなされたもので、２．３，
６．７−ナフタレンテトラカルボン酸を高収率かつ高純
度に精製できる分離・精製法を提供することを目的とす
る。The present invention has been made in view of the above points, and includes 2.3.
An object of the present invention is to provide a separation/purification method that can purify 6.7-naphthalenetetracarboxylic acid in high yield and purity.
本発明者らは、上記目的を達成するために鋭意研究し、
２．３，６．７−ナフタレンテトラカルボン酸が、他の
カルボン酸異性体に比べ、特定の溶媒に対する溶解度が
極めて大きいことを見出し、本発明を完成させたもので
ある。The present inventors have conducted extensive research to achieve the above objectives,
The present invention was completed based on the discovery that 2.3,6.7-naphthalenetetracarboxylic acid has extremely high solubility in a specific solvent compared to other carboxylic acid isomers.
すなわち、２，３，６．７−ナフタレンテトラカルボン
酸の水、メタノール、エタノール、１−プロパノール、
２−プロパノール、１−ブタノール、２−ブタノール、
エチレングリコールに対する溶解度は他のカルボン酸異
性体の溶解度に比べると極めて大きいものであった。し
たがって、各種ナフタレンカルボン酸混合物から、２，
３，６．７−ナツタレンチ）・ラカルボン酸を、所定の
溶媒を用いて高選択的に抽出できることになる。That is, water, methanol, ethanol, 1-propanol, 2,3,6.7-naphthalenetetracarboxylic acid,
2-propanol, 1-butanol, 2-butanol,
The solubility in ethylene glycol was extremely high compared to the solubility of other carboxylic acid isomers. Therefore, from various naphthalene carboxylic acid mixtures, 2,
This means that 3,6.7-Natsutalenti)·racarboxylic acid can be extracted with high selectivity using a predetermined solvent.
つまり、本発明のナフタレンテトラカルボン酸の分前・
精製法は、２，３，６．７−ナフタレンテトラカルボン
酸を含む各種ナフタレンカルボン酸混合物より、２．３
．６．７−ナフタレンテトラカルボン酸を、溶媒により
抽出することを特徴として構成されている。In other words, the amount of naphthalenetetracarboxylic acid of the present invention
The purification method is based on a mixture of various naphthalenecarboxylic acids including 2,3,6.7-naphthalenetetracarboxylic acid.
．． 6.7-Naphthalenetetracarboxylic acid is extracted with a solvent.
抽出に用いる溶媒は、極性溶媒、例えば、水、メタノー
ル、エタノール、１−プロパノール、２−プロパノール
、１−ブタノール、２−ブタノール、エチレングリコー
ルおよびこれらの混合液等が好ましく、特に水、メタノ
ール、エタノール、１−プロパノール、２−プロパノー
ルが好ましい。The solvent used for extraction is preferably a polar solvent, such as water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, ethylene glycol, or a mixture thereof, particularly water, methanol, or ethanol. , 1-propanol and 2-propanol are preferred.
溶媒による抽出方法は、ソックスレー（Ｓｏｘｌｅｔ）
抽出等の連続的抽出方法、抽出溶媒中に混合物を分散さ
せ、加熱・撹拌した後濾液を分離するハツチ式抽出方法
、混合物中を溶媒を通過させる方法等、従来行われてい
る各種抽出方法を用いることができる。The extraction method using a solvent is Soxlet
Various conventional extraction methods are used, including continuous extraction methods such as extraction, hatch-type extraction methods in which the mixture is dispersed in an extraction solvent, heated and stirred, and then the filtrate is separated, and methods in which the solvent is passed through the mixture. Can be used.
抽出温度については、特に制限はないが、−２０“０〜
４０°Ｃが好ましい。There are no particular restrictions on the extraction temperature, but from -20"0 to
40°C is preferred.
〔作用］
本発明のナフタレンテトラカルボン酸の分離・精製法で
は、溶媒にナフタレンカルボン酸混合物中の主として２
．３．６．７−ナフタレンテトラカルボン酸のみを溶解
させ、そしてこの熔解した２、３，６．７ナフタレンテ
トラカルボン酸を抽出する。[Function] In the method for separating and purifying naphthalenetetracarboxylic acid of the present invention, the solvent mainly contains 2
．． 3. Dissolve only 6.7-naphthalenetetracarboxylic acid and extract the dissolved 2,3,6.7naphthalenetetracarboxylic acid.
［実施例］ 以下、本発明の実施例を図面に基づいて説明する。[Example] Embodiments of the present invention will be described below based on the drawings.
第１図は本発明のナフタレンテトラカルボン酸の分離・
精製法の手順を示す流れ図である。Figure 1 shows the separation and separation of naphthalenetetracarboxylic acid of the present invention.
1 is a flowchart showing the steps of a purification method.
ヘンケル転位反応工程Ａ：
ナフタレン−モノ、ジ、トリカルボン酸のアルカリ塩を
原料として、炭酸ガスによる加圧のもとに、酸化カドミ
ウム（ＣｄＯ）及びヨウ化ナトリウム（Ｎａｌ）の触媒
の存在下で加熱して反応させ、ナフタレンテトラカルボ
ン酸アルカリ塩のほか、ナフタレンモノカルボン酸塩、
ナフタレンジカルボン酸塩、ナフタレントリカルボン酸
塩等が含まれたナフタレンカルボン酸アルカリ塩混合物
を生成する。Henkel rearrangement reaction step A: Naphthalene - alkali salts of mono-, di-, and tricarboxylic acids are used as raw materials and heated in the presence of catalysts of cadmium oxide (CdO) and sodium iodide (Nal) under pressure with carbon dioxide gas. In addition to naphthalenetetracarboxylic acid alkali salts, naphthalene monocarboxylic acid salts,
A naphthalene carboxylic acid alkali salt mixture containing naphthalene dicarboxylate, naphthalene tricarboxylate, etc. is produced.
酸析工程Ｂ：
ナフタレンカルボン酸アルカリ塩混合物を酸析し、２，
３，６．７−ナフタレンテトラカルボン酸を含むナフタ
レンカルボン酸混合物を生成する。Acid precipitation step B: Acid precipitation of the naphthalene carboxylic acid alkali salt mixture, 2,
A naphthalene carboxylic acid mixture containing 3,6.7-naphthalene tetracarboxylic acid is produced.
溶媒抽出工程Ｃ；
ナフタレンカルボン酸混合物を原料とし、水、メタノー
ル、エタノール、１−プロパノール、２−プロパノール
、１−ブタノール、２−フタノール、エチレングリコー
ルの極性溶媒で２．３，６．７−ナフタレンテトラカル
ボン酸を抽出する。Solvent extraction step C: Using a naphthalene carboxylic acid mixture as a raw material, 2.3,6.7-naphthalene is extracted with a polar solvent of water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-phthanol, and ethylene glycol. Extract the tetracarboxylic acid.
次に、本発明の実施例と従来例を比較した実験結果につ
いて説明するが、本発明は以下の実施例にのみ限定され
るものではない。Next, the results of an experiment comparing an example of the present invention and a conventional example will be described, but the present invention is not limited to the following examples.
実施例１
ヘンケル転位反応工程Ａ・酸析工程Ｂ：１！オートクレ
ーブに、ナフタレンジカルボン酸二ナトリウム塩２４０
ｇ、触媒としてＣｄ０１２ｇ、Ｎａ １１８０ｇを入れ
、炭酸ガスを初圧３０ｋｇ／ｃｄ Ｇで仕込み加熱して
反応温度４６０’Ｃ１反応圧力１１０ｋｇ／ｄＧに到達
させた。この状態で、３時間反応を継続した後冷却した
。内容固形物を取り出し、これをアセトンで洗浄した後
、水に溶解させて不溶分を除き、１０％ＨＣＩあるいは
硫酸で酸性とした。生した固形物を集めて水で洗浄後乾
燥させ、１３５ｇのカルボン酸混合物を得た。得られた
混合物の組成は、表１に示す通りである。Example 1 Henkel rearrangement reaction step A/acid precipitation step B: 1! In the autoclave, naphthalene dicarboxylic acid disodium salt 240
g, 12 g of Cd and 1180 g of Na as catalysts were charged, and carbon dioxide gas was charged at an initial pressure of 30 kg/cdG and heated to reach a reaction temperature of 460'C1 and a reaction pressure of 110 kg/dG. In this state, the reaction was continued for 3 hours and then cooled. The solid content was taken out, washed with acetone, dissolved in water to remove insoluble matter, and acidified with 10% HCI or sulfuric acid. The resulting solid was collected, washed with water, and dried to obtain 135 g of a carboxylic acid mixture. The composition of the obtained mixture is as shown in Table 1.
表１
溶媒抽出工程Ｃ：
表１に示す組成のナフタレンカルボン酸混合物１００ｇ
に、溶媒としてメタノール７９０ｇを加え、室温で約３
０分間撹拌後、濾過を行った。濾液からメタノールを除
去し、３２．４ｇの固形物を得た。得られた固形物中の
２．３，６．７−ナフタレンテトラカルボン酸純度は９
８．６％、抽出による２、３，６．７−ナフタレンテト
ラカルボン酸の収率は８３，９％であった。Table 1 Solvent extraction step C: 100 g of naphthalene carboxylic acid mixture having the composition shown in Table 1
790g of methanol was added as a solvent, and the mixture was heated at room temperature for about 3
After stirring for 0 minutes, filtration was performed. Methanol was removed from the filtrate to obtain 32.4 g of solid. The purity of 2.3,6.7-naphthalenetetracarboxylic acid in the obtained solid was 9.
The yield of 2,3,6,7-naphthalenetetracarboxylic acid by extraction was 83.9%.
実施例２〜６
溶媒抽出工程における使用溶媒の種類及び量を変えたほ
かは、実施例１と同一の条件で同一の操作を行った。Examples 2 to 6 The same operation was performed under the same conditions as in Example 1, except that the type and amount of the solvent used in the solvent extraction step were changed.
比較例１〜２
溶媒抽出工程における使用溶媒の種類及び量を変えたほ
かは、実施例１と同一の条件で同一の操作を行った。Comparative Examples 1 and 2 The same operation was performed under the same conditions as in Example 1, except that the type and amount of the solvent used in the solvent extraction step were changed.
実施例および比較例の結果を表２に示す。Table 2 shows the results of Examples and Comparative Examples.
（以下余白）
表２
＊：含有する２、 ３．６．７−ナフタレンテトラカル
ボン酸に対する理論Ｙｉｅｌｄ１１１１：未計算（選択
的抽出でないため）〔発明の効果〕
本発明は、２，３，６．７−ナフタレンテトラカルボン
酸を高収率かつ高純度に分離・精製することができる。(Leaving space below) Table 2 *: Theoretical Yield 1111 for contained 2, 3, 6, 7-naphthalene tetracarboxylic acid: Not calculated (because it is not selective extraction) [Effects of the invention] The present invention provides 2, 3, 6. 7-Naphthalenetetracarboxylic acid can be separated and purified with high yield and high purity.
第１図は本発明のナフタレンテトラカルボン酸の分離・
精製法の一実施例の流れ図である。Figure 1 shows the separation and separation of naphthalenetetracarboxylic acid of the present invention.
1 is a flowchart of one embodiment of a purification method.
Claims (5)
含む各種ナフタレンカルボン酸混合物より、２，３，６
，７−ナフタレンテトラカルボン酸を、溶媒により抽出
することを特徴とする２，３，６，７−ナフタレンテト
ラカルボン酸の分離・精製法(1) From various naphthalenecarboxylic acid mixtures including 2,3,6,7-naphthalenetetracarboxylic acid, 2,3,6
, 7-naphthalenetetracarboxylic acid is extracted with a solvent.
，３，６，７−ナフタレンテトラカルボン酸の分離・精
製法(2) 2 according to claim (1), wherein the solvent is a polar solvent.
, 3,6,7-naphthalenetetracarboxylic acid separation and purification method
プロパノール、２−プロパノール、１−ブタノール、２
−ブタノール、エチレングリコールのうち１種または２
種以上の混合液である請求項（２）に記載の２，３，６
，７−ナフタレンテトラカルボン酸の分離・精製法(3) The polar solvent is water, methanol, ethanol, 1-
Propanol, 2-propanol, 1-butanol, 2
-One or two of butanol and ethylene glycol
2, 3, 6 according to claim (2), which is a mixed liquid of more than one species.
, 7-naphthalenetetracarboxylic acid separation and purification method
ロセスである請求項（１）に記載の２，３，６，７−ナ
フタレンテトラカルボン酸の分離・精製法(4) The method for separating and purifying 2,3,6,7-naphthalenetetracarboxylic acid according to claim (1), wherein the solvent extraction method is a continuous extraction method or a batch process.
過法である請求項（４）に記載の２，３，６，７−ナフ
タレンテトラカルボン酸の分離・精製法(5) The method for separating and purifying 2,3,6,7-naphthalenetetracarboxylic acid according to claim (4), wherein the solvent extraction method is a Soxhlet method or a washing/filtration method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2274828A JP2513530B2 (en) | 1990-10-12 | 1990-10-12 | Separation and purification method of tetracarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2274828A JP2513530B2 (en) | 1990-10-12 | 1990-10-12 | Separation and purification method of tetracarboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04149149A true JPH04149149A (en) | 1992-05-22 |
| JP2513530B2 JP2513530B2 (en) | 1996-07-03 |
Family
ID=17547143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2274828A Expired - Fee Related JP2513530B2 (en) | 1990-10-12 | 1990-10-12 | Separation and purification method of tetracarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2513530B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5770766A (en) * | 1995-11-13 | 1998-06-23 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method for separating and purifying hydroxynaphtalenecarboxylic acids |
| WO2020160201A1 (en) * | 2019-01-31 | 2020-08-06 | Sabic Global Technologies B.V. | Method for purification of a biphenol tetraacid composition and a biphenol tetraacid composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0269434A (en) * | 1988-09-05 | 1990-03-08 | Nkk Corp | Separation of 2,3,6,7-naphthalene-tetracarboxylic acid |
| JPH0269433A (en) * | 1988-09-05 | 1990-03-08 | Nkk Corp | Preparation of 2,3,6,7-naphthalene-tetracarboxylic acid alkali salt |
-
1990
- 1990-10-12 JP JP2274828A patent/JP2513530B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0269434A (en) * | 1988-09-05 | 1990-03-08 | Nkk Corp | Separation of 2,3,6,7-naphthalene-tetracarboxylic acid |
| JPH0269433A (en) * | 1988-09-05 | 1990-03-08 | Nkk Corp | Preparation of 2,3,6,7-naphthalene-tetracarboxylic acid alkali salt |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5770766A (en) * | 1995-11-13 | 1998-06-23 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method for separating and purifying hydroxynaphtalenecarboxylic acids |
| WO2020160201A1 (en) * | 2019-01-31 | 2020-08-06 | Sabic Global Technologies B.V. | Method for purification of a biphenol tetraacid composition and a biphenol tetraacid composition |
| US11623908B2 (en) | 2019-01-31 | 2023-04-11 | Shpp Global Technologies B.V. | Method for purification of a biphenol tetraacid composition and a biphenol tetraacid composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2513530B2 (en) | 1996-07-03 |
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