JPH01186839A - Recovery of aromatic acid anhydride - Google Patents
Recovery of aromatic acid anhydrideInfo
- Publication number
- JPH01186839A JPH01186839A JP626888A JP626888A JPH01186839A JP H01186839 A JPH01186839 A JP H01186839A JP 626888 A JP626888 A JP 626888A JP 626888 A JP626888 A JP 626888A JP H01186839 A JPH01186839 A JP H01186839A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- acid anhydride
- anhydride
- acid
- residue
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000011084 recovery Methods 0.000 title description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 238000004040 coloring Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 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 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005406 washing Methods 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）
本発明は芳香族酸無水物の製造時に生ずる残渣等から芳
香族多価カルメン酸を回収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 recovering aromatic polycarmenic acid from residues etc. generated during the production of aromatic acid anhydrides.
（従来技術）
例えば芳香族酸無水物を、芳香族多価カルがン酸と無水
酢酸とを反応させて得る場合（特許６２−２３４０８６
等）、無水化反応後、反応液を冷却し、固液分離工程に
移るが、この時に得られたＰ液は加熱、濃縮され、未反
応の無水酢酸、副生酢酸等の回収がなされる。(Prior art) For example, when aromatic acid anhydride is obtained by reacting aromatic polycarboxylic acid and acetic anhydride (Patent No. 62-234086
etc.) After the anhydration reaction, the reaction solution is cooled and moved to the solid-liquid separation step. The P solution obtained at this time is heated and concentrated, and unreacted acetic anhydride, by-product acetic acid, etc. are recovered. .
この時、生じた回収後の残渣は、通常、更にＦ液が加え
られた後、同様の操作で上記２種の酸回収を繰秒返すだ
けであり、最終的にタール化し九残渣は、その着色のた
め、廃棄せざるをえなかった。At this time, the resulting recovered residue is usually simply added with liquid F, and then the above two types of acid recovery are repeated over and over again in the same manner, and the residue is finally turned into tar. Due to the coloring, I had to throw it away.
（発明が解決しようとする問題点）
ところがこの残渣は多量の着色し念芳香族酸無水物で構
成されており、廃棄という操作は製品収車上、又、省資
源という意味から極めて好ましくない。(Problems to be Solved by the Invention) However, this residue is composed of a large amount of colored aromatic acid anhydride, and the operation of discarding it is extremely undesirable from the standpoint of product collection and resource conservation.
また、この廃棄作業は大きな手間と労力を必要としてい
た。Moreover, this disposal work required a great deal of time and effort.
本発明はこのような廃棄物から低コストで容易に有価物
を回収することを目的とするものである。The present invention aims to easily recover valuable materials from such waste at low cost.
（問題点を解決するための手段）
本発明は、著しい着色のために再利用不可能とされてい
た芳香族酸無水物に水を添加し、該無水物を芳香族多価
カルボン酸に分解した後、晶析することで該無水物を芳
香族多価カルボン酸として回収する方法である。(Means for Solving the Problems) The present invention adds water to aromatic acid anhydrides, which have been considered unrecyclable due to severe coloring, and decomposes the anhydrides into aromatic polycarboxylic acids. After that, the anhydride is recovered as an aromatic polycarboxylic acid by crystallization.
本発明に適用される芳秀族多価カルゼ／酸としては、ご
タル酸、トリメリット酸、ピロメリット酸、３．４．３
’、４’−ベンゾフェノンテトラカルボン酸、３．３′
、４，４′−ジフェニルテトラカルがン酸、２．３，６
．７−ナフタレンチトラカルゲン酸、２．２−ビス（３
，４−シカルはキシフェニル）ｆロノヤン、ビス（３，
４−ノカル、ゲキシフェニル）スルホン等力する。
”本発明における着色した芳香族酸無水物とは、例え
ば次の様にして得られるものである。Examples of the aromatic polycarboxylic acid/acid applicable to the present invention include tartaric acid, trimellitic acid, pyromellitic acid, 3.4.3
',4'-benzophenonetetracarboxylic acid, 3.3'
, 4,4'-diphenyltetracarboxylic acid, 2.3,6
．． 7-naphthalentitracargenic acid, 2,2-bis(3
, 4-cycal is xyphenyl) f Lonoyan, bis(3,
4-nocal, gexyphenyl) sulfone, etc.
``The colored aromatic acid anhydride in the present invention is obtained, for example, in the following manner.
前述した様な芳香族多価カルゲン酸と無水酢酸とを反応
させて芳香族酸無水物を得る場合、無水化反応後の反応
液を冷却して、生成した酸無水物の大部分を晶析させ、
これを固液分離する。この“Ｆｆｆｌより未反応の無水
酢酸および副生酢酸あるいは、反応溶媒を使用した場合
には更にこの反応溶媒を蒸留等罠より回収する。この残
渣が本発明の着色した芳香族酸無水物を含むものであり
、タール分等の不純物を含有する着色物である。When an aromatic acid anhydride is obtained by reacting an aromatic polycargenic acid with acetic anhydride as described above, the reaction solution after the anhydration reaction is cooled and most of the generated acid anhydride is crystallized. let me,
This is separated into solid and liquid. From this Fffl, unreacted acetic anhydride and by-product acetic acid, or if a reaction solvent is used, the reaction solvent is further recovered from a trap such as distillation. This residue contains the colored aromatic acid anhydride of the present invention. It is a colored material that contains impurities such as tar.
この残渣を通常はアセトン等の溶媒により洗浄する。洗
浄後の湿芳香族酸無水物に水を添加し、加熱溶解（加水
分解）させ、冷却忙より晶析して、芳香族多価カルＲン
酸結晶を取りだす。This residue is usually washed with a solvent such as acetone. Water is added to the washed wet aromatic acid anhydride, heated to dissolve (hydrolyzed), and crystallized while cooling to take out aromatic polycarboxylic acid crystals.
この水による再結晶は数回繰り返せばそれだけ純度の高
い回収芳香族多価カルダン酸を得ることができるが、合
計２回同操作を行うだけでも比較的高純度の回収物を得
ることが可能である。If this recrystallization with water is repeated several times, it is possible to obtain recovered aromatic polyhydric cardanic acid with a higher purity, but it is also possible to obtain a recovered product with relatively high purity by repeating the same operation only twice in total. be.
なお、Ｆ液からの反応溶媒等の回収は、通常、残渣の量
が、ＷｇＦ液容量の８〜１５チになるまで行う事が、前
述の晶析操作を行うのに効果的である。Note that it is usually effective to recover the reaction solvent etc. from the F solution until the amount of the residue reaches 8 to 15 times the volume of the WgF solution in order to carry out the above-mentioned crystallization operation.
本発明の回収方法は、上記の具体的に示した残渣のみで
なく、各種のグロセスにおいて生成する芳香族酸無水物
を含有するものに適用できる。The recovery method of the present invention can be applied not only to the residues specifically shown above, but also to those containing aromatic acid anhydrides produced in various types of grosses.
（発明の効果）
本発明の方法により、これまで廃棄していた残ることが
できる。(Effects of the Invention) By the method of the present invention, it is possible to use the remaining materials that were previously discarded.
実施例１
ｔｏｎ
ピロメリット酸２９ と無水酢酸４ Ｂ ｔｏｎの反
応により無水ピロメリット酸を製造した反応液を冷却し
て生成した無水ピロメリット酸の大部分を晶析させ固液
分離した。得られたＦ液より未反応の無水酢酸および副
生酢酸を回収した。これにより着色した残渣１１１８に
９が得られた。Example 1 Pyromellitic anhydride was produced by a reaction between 29 tons of pyromellitic acid and 4 B tons of acetic anhydride. A reaction solution was cooled, and most of the produced pyromellitic anhydride was crystallized and separated into solid and liquid. Unreacted acetic anhydride and by-product acetic acid were recovered from the obtained solution F. This gave a colored residue 1118 to 9.
これＶＣ７４００に９の水を仕込み、１００℃まで加熱
し、１時間かけ完全に溶解させたあと２０ｃ１で冷却し
、晶析させ念。This VC7400 was charged with 9 water, heated to 100°C, completely dissolved over 1 hour, and then cooled to 20ml to allow crystallization.
固液分離後、同様の操作で再結晶を行った結果、純度９
８％のピロメリット酸が１０８９に９回収できた。After solid-liquid separation, recrystallization was performed in the same manner, and the purity was 9.
8% pyromellitic acid was recovered 9 out of 1089 times.
実施例２
実施例１と同様の反応により得られた反応液を晶析して
得られた無水ピロメリット酸湿粉をアセトンで洗浄し、
この洗浄液よりアセトンを回収した残渣６４８−を得念
。Example 2 Pyromellitic anhydride wet powder obtained by crystallizing the reaction liquid obtained by the same reaction as in Example 1 was washed with acetone,
Acetone was recovered from this washing solution to form a residue 648-.
これに３４００ｋｇの水を添加し、１００℃に加熱し、
１時間で完全に溶解させ友。次にこれヲ２０℃に冷却し
ピロメリット酸を晶析した。Add 3400kg of water to this and heat it to 100℃,
It dissolves completely in 1 hour. Next, this was cooled to 20°C to crystallize pyromellitic acid.
固液分離後、同様の操作で再結晶を行り九結果、純度９
０％のピロメリット酸６８３ｋｌ？が得られた。After solid-liquid separation, recrystallization was performed using the same procedure and the purity was 9.
0% pyromellitic acid 683kl? was gotten.
Claims (1)
族多価カルボン酸に分解した後、晶析することを特徴と
する該無水物を芳香族多価カルボン酸として回収する方
法。A method for recovering the anhydride as an aromatic polycarboxylic acid, which comprises adding water to a colored aromatic acid anhydride, decomposing the anhydride into an aromatic polycarboxylic acid, and then crystallizing the anhydride. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP626888A JPH01186839A (en) | 1988-01-14 | 1988-01-14 | Recovery of aromatic acid anhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP626888A JPH01186839A (en) | 1988-01-14 | 1988-01-14 | Recovery of aromatic acid anhydride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01186839A true JPH01186839A (en) | 1989-07-26 |
Family
ID=11633687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP626888A Pending JPH01186839A (en) | 1988-01-14 | 1988-01-14 | Recovery of aromatic acid anhydride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01186839A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017149709A (en) * | 2016-02-24 | 2017-08-31 | 三洋化成工業株式会社 | Method for producing dibasic acid |
| CN108663246A (en) * | 2018-05-18 | 2018-10-16 | 中国烟草总公司郑州烟草研究院 | Benzophenone purity rubric substance and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61134342A (en) * | 1984-12-04 | 1986-06-21 | Nippon Jiyouriyuu Kogyo Kk | Production of organic acid from solid organic acid anhydride |
| JPS62212340A (en) * | 1986-03-14 | 1987-09-18 | Kureha Chem Ind Co Ltd | Simultaneous production of 2,6-naphthalene-dicarboxylic acid and trimellitic acid |
| JPS62270548A (en) * | 1986-05-16 | 1987-11-24 | Mitsubishi Chem Ind Ltd | Production of high-purity terephthalic acid |
-
1988
- 1988-01-14 JP JP626888A patent/JPH01186839A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61134342A (en) * | 1984-12-04 | 1986-06-21 | Nippon Jiyouriyuu Kogyo Kk | Production of organic acid from solid organic acid anhydride |
| JPS62212340A (en) * | 1986-03-14 | 1987-09-18 | Kureha Chem Ind Co Ltd | Simultaneous production of 2,6-naphthalene-dicarboxylic acid and trimellitic acid |
| JPS62270548A (en) * | 1986-05-16 | 1987-11-24 | Mitsubishi Chem Ind Ltd | Production of high-purity terephthalic acid |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017149709A (en) * | 2016-02-24 | 2017-08-31 | 三洋化成工業株式会社 | Method for producing dibasic acid |
| CN108663246A (en) * | 2018-05-18 | 2018-10-16 | 中国烟草总公司郑州烟草研究院 | Benzophenone purity rubric substance and preparation method thereof |
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