JPH03167181A - Purification of carboxylic acid anhydride - Google Patents
Purification of carboxylic acid anhydrideInfo
- Publication number
- JPH03167181A JPH03167181A JP30640389A JP30640389A JPH03167181A JP H03167181 A JPH03167181 A JP H03167181A JP 30640389 A JP30640389 A JP 30640389A JP 30640389 A JP30640389 A JP 30640389A JP H03167181 A JPH03167181 A JP H03167181A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- acid anhydride
- anhydride
- filtrate
- 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
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- HTXWSYPMOXEWQV-UHFFFAOYSA-N naphtho[3,2-e][2]benzofuran-1,3,6,11-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2)=C1C1=C2C(=O)OC1=O HTXWSYPMOXEWQV-UHFFFAOYSA-N 0.000 abstract description 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- -1 1,4- Diamino-5-hydroxyanthraquinone-2,3-dicarboxylic anhydride Chemical compound 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- JLSLIROFCPAEGA-UHFFFAOYSA-N 4,11-diaminonaphtho[2,3-f][2]benzofuran-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C1C(=O)OC(=O)C1=C2N JLSLIROFCPAEGA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FUZYYLWVPAGQHG-UHFFFAOYSA-N 11-amino-4-hydroxynaphtho[2,3-f][2]benzofuran-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C1C(=O)OC(=O)C1=C2O FUZYYLWVPAGQHG-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UGOABQVUDBNSOX-UHFFFAOYSA-N 9,10-dioxoanthracene-2,3-dicarbonitrile Chemical compound N#CC1=C(C#N)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 UGOABQVUDBNSOX-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- KHSQVAWUVKIOOT-UHFFFAOYSA-N O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(=O)OC(=O)C1=C2O Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(=O)OC(=O)C1=C2O KHSQVAWUVKIOOT-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VGEMYWDUTPQWBN-UHFFFAOYSA-N n-ethyl-2-methoxyethanamine Chemical compound CCNCCOC VGEMYWDUTPQWBN-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、色素の中間体であるアントラキノンジカルボ
ン酸無水物の精製法に関する.〔従来の技術及び発明が
解決しようとする課題〕1.4−ジアミノアントラキノ
ン−2.3−ジカルポン酸無水物の製造方法として、1
.4−ジアくノー2.3−ジシアノアントラキノンを加
水分解する下式(A)の方法が” The Chemi
stry of SyntheticDyes+ V
olumel[I ″ K. Venkatara
san著; ^cademicPress
刊の
414頁に記載されている,
(a)
しかしながら、
弐(A)
の方法には副反応とし
て下記式(B)
の反応がおこり、
(Bノ
(b)
r11無水物(a)
中に、
イミド(b)が必ず共存す
るという欠点があった。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for purifying anthraquinone dicarboxylic acid anhydride, which is an intermediate for dyes. [Prior art and problems to be solved by the invention] As a method for producing 1,4-diaminoanthraquinone-2,3-dicarboxylic acid anhydride, 1
.. The method of the following formula (A) for hydrolyzing 4-diaquinone and 2,3-dicyanoanthraquinone is "The Chemi
Try of Synthetic Dyes + V
olumel [I ″ K. Venkatara
(a) However, in method 2 (A), the reaction of the following formula (B) occurs as a side reaction, and (B no (b) r11 anhydride. There was a drawback that imide (b) always coexisted in (a).
又、酸無水物(a)、イミド(b)、いずれの化合物と
も溶媒に難溶なため、tit製が出来なかった。Furthermore, since both the acid anhydride (a) and the imide (b) are poorly soluble in solvents, tit products could not be produced.
本発明者らは、一般式(1)
(式(1)中、Yl, Y!、Y3、およびY4は各々
独立に水素原子、アミノ基、水酸基を表わす.)で示さ
れる酸無水物を溶媒中、下記一般式(II)(式(U)
中、R+及びR2は各々独立に炭素数l〜10のアルキ
ル基、アルコキシアルキル基、又はヒドロキシアルキル
基を表わす.)
で示される2級アミンにてア旦ツク酸として溶媒可溶化
し、これを精製して高純度アミソク酸とした後、酸処理
をすることにより高純度の酸無水物(I)を得る方法を
提案した.
しかしこの方法では、アミンク酸を一度単離し、酸で加
水分解を行なっているため減圧濃縮工程を必要とし、工
業的に利用する一般的合或法としては問題があった。そ
のため、より高収率で簡便な新しい方法を検討する必要
があった。The present inventors used an acid anhydride represented by the general formula (1) (in formula (1), Yl, Y!, Y3, and Y4 each independently represents a hydrogen atom, an amino group, and a hydroxyl group) in a solvent. Among them, the following general formula (II) (formula (U)
In the formula, R+ and R2 each independently represent an alkyl group, an alkoxyalkyl group, or a hydroxyalkyl group having 1 to 10 carbon atoms. ) A method of obtaining high purity acid anhydride (I) by solubilizing amisocic acid in a solvent with a secondary amine represented by the formula, refining this to obtain high purity amisocic acid, and then treating with an acid. proposed. However, in this method, since the aminucic acid is once isolated and hydrolyzed with an acid, a vacuum concentration step is required, which is problematic as a general synthesis method for industrial use. Therefore, it was necessary to consider a new method with higher yield and ease of use.
本発明者らは、一般式(1)
(弐(1)中、Y1、Y2、Y3、およびY4は各々独
立に水素原子、アミノ基、水酸基を表わす。)で示され
る酸無水物を溶媒中、下記一般式(n)(式(II)中
、Rl及びR2は各々独立に炭素数1〜10のアルキル
基、アルコキシアルキル基、又はヒドロキシアルキル基
を表わす。)
で示される2級アミンと反応して製造される下記一般式
(Ill)
(式(I[l) − y’, yz, y’及ヒy4
ハ、式( 1 ) (Dyl, yffi, y3、Y
4と同一であり、R+及びR2は式(II)のRl,
Rtと同一である。)
で示される化合物として溶媒可溶化し、不溶性のイミド
体及びその他の不溶物を濾別し、続いて濾液から溶媒を
を留去することなく、そのまま濾液に酸を加えて、加水
分解処理して酸無水物とすることにより、高純度の酸無
水物(1)が得られることを見出した.
式(1)で示される化合物の具体例としては、1.4−
ジア旦ノアントラキノン−2.3−ジカルボン酸無水物
、 1.4−ジヒドロキシアントラキノン2.3−ジカ
ルポン酸無水物、l−アミノ−4ヒドロキシアントラキ
ノン−2.3−ジカルボン酸無水物、1.4−ジアミノ
ー5−ヒドロキシアントラキノン−2.3−ジカルボン
酸無水物、184−ジア旦ノー5,8−ジヒドロキシア
ントラキノン2.3−ジカルボン酸無水物、1,4.5
−トリアもノアントラキノン−2.3−ジカルポン酸無
水物、1.4,5.8−テトラアミノアントラキノン−
2.3ージカルボン酸無水物、1.5−ジアくノー4,
8−ジヒドロキシアントラキノン−2.3−ジカルボン
酸無水物、 1,8−ジアミノー4.5−ジヒドロキシ
アントラキノン−2.3−ジカルボン酸無水物などが挙
げられる。The present inventors prepared an acid anhydride represented by the general formula (1) (in (1), Y1, Y2, Y3, and Y4 each independently represent a hydrogen atom, an amino group, and a hydroxyl group) in a solvent. , reacts with a secondary amine represented by the following general formula (n) (in formula (II), R1 and R2 each independently represent an alkyl group, an alkoxyalkyl group, or a hydroxyalkyl group having 1 to 10 carbon atoms). The following general formula (Ill) (formula (I[l) - y', yz, y' and hy4
C, Formula (1) (Dyl, yffi, y3, Y
4, and R+ and R2 are Rl of formula (II),
Same as Rt. ) The compound represented by is solubilized in a solvent, the insoluble imide form and other insoluble substances are filtered out, and then an acid is added to the filtrate without distilling off the solvent from the filtrate, and hydrolyzed. It has been found that highly pure acid anhydride (1) can be obtained by converting it into an acid anhydride. Specific examples of the compound represented by formula (1) include 1.4-
Diatannoanthraquinone-2,3-dicarboxylic anhydride, 1,4-dihydroxyanthraquinone-2,3-dicarboxylic anhydride, l-amino-4-hydroxyanthraquinone-2,3-dicarboxylic anhydride, 1,4- Diamino-5-hydroxyanthraquinone-2,3-dicarboxylic anhydride, 184-diamino-5,8-dihydroxyanthraquinone-2,3-dicarboxylic anhydride, 1,4.5
-Triaminoanthraquinone-2,3-dicarboxylic anhydride, 1.4,5.8-tetraaminoanthraquinone-
2.3-dicarboxylic anhydride, 1.5-diaquinone 4,
Examples include 8-dihydroxyanthraquinone-2,3-dicarboxylic anhydride, 1,8-diamino-4,5-dihydroxyanthraquinone-2,3-dicarboxylic anhydride, and the like.
式(It)で示される2級アミンの例としては、ジメチ
ルアミン、ジエチルアミン、ジブチルアミン、ジオクチ
ルアミン、ジシクロヘキシルアミン、ジエタノールアミ
ン、N−ヒドロキシエチルーNエチルアξン、N−メト
キシエチルーN一エチルアミンなどが挙げられる。Examples of the secondary amine represented by formula (It) include dimethylamine, diethylamine, dibutylamine, dioctylamine, dicyclohexylamine, diethanolamine, N-hydroxyethyl-N-ethylamine, N-methoxyethyl-N-ethylamine, etc. can be mentioned.
式(It)で示される2級ア旦ンの使用量は、式(1)
で示される酸無水物の1.0〜2.0モル比である.
又、溶媒としては、反応系中で生或するアミック酸を溶
解し、イミド体を溶解しない溶媒ならば何でもよいが、
好ましくはメタノール、エタノール、プロバノール、ブ
タノールなどのアルコール類、メチルセロソルブ、エチ
ルセロソルブ、ブチルセロソルブなどのセロソルプ類が
特に好ましく、その使用量は、式(1)の粗製物の10
〜30倍、好ましくは15〜25倍量である.
酸処理に用いる酸としては、無機系の酸ならばいずれで
もよいが、好ましくは塩酸、臭化水素酸、硫酸、硝酸、
リン酸などである。The usage amount of 2nd class Adan shown by the formula (It) is as shown in the formula (1)
The molar ratio of the acid anhydride is 1.0 to 2.0. In addition, any solvent may be used as long as it dissolves the amic acid produced in the reaction system but does not dissolve the imide form.
Preferably, alcohols such as methanol, ethanol, probanol, and butanol, and cellosolves such as methyl cellosolve, ethyl cellosolve, and butyl cellosolve are particularly preferable, and the amount used is 10% of the crude product of formula (1).
~30 times, preferably 15 to 25 times the amount. The acid used in the acid treatment may be any inorganic acid, but preferably hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid,
Such as phosphoric acid.
反応に用いられる酸の割合は特に限定されるものではな
く、通常は、−C式(I[l)の化合物lモルに対し、
1モル程度用いるのが好ましい。The ratio of acid used in the reaction is not particularly limited, and is usually 1 mole of the compound of formula -C (I[l)].
It is preferable to use about 1 mol.
式(1)と式(n)で示される化合物の反応温度は、1
0〜300゜Cであるが、好ましくは室温から200゜
Cである.反応時間は、0.5〜30時間、好ましくは
l〜10時間である.
また、式(I[l)の化合物を加水分解する反応温度は
、10〜300”C,好ましくは室温から100’Cで
ある.反応時間は、0.5〜30時間、好ましくは1〜
5時間である.
〔実施例〕
以下、実施例により本発明を詳しく説明する.実施例l
1 1.4−ジアミノーアントラキノン−2.3−ジカ
ルボン酸無水物(純度60%)200 g , n−ジ
ブチルアミン125gをエチルセロソルブ2 f 中、
120’Cに昇温し、6時間反応した.反応後、反応液
を冷却し、濾過した後、濾液にlO%塩酸水溶液142
gを加え、90゜Cに昇温し、3時間加水分解した後、
析出した結晶を濾過し、水洗、乾燥して、1.4=ジア
ミノアントラキノン−2.3−ジカルボン酸無水物11
4gを得た。純度は99%であった。The reaction temperature of the compounds represented by formula (1) and formula (n) is 1
0 to 300°C, preferably room temperature to 200°C. The reaction time is 0.5 to 30 hours, preferably 1 to 10 hours. The reaction temperature for hydrolyzing the compound of formula (I[l) is 10 to 300''C, preferably room temperature to 100'C. The reaction time is 0.5 to 30 hours, preferably 1 to 300''C.
It is 5 hours. [Example] Hereinafter, the present invention will be explained in detail with reference to Examples. Example l 1 200 g of 1,4-diamino-anthraquinone-2,3-dicarboxylic anhydride (purity 60%), 125 g of n-dibutylamine in ethyl cellosolve 2 f.
The temperature was raised to 120'C and the reaction was continued for 6 hours. After the reaction, the reaction solution was cooled and filtered, and the filtrate was added with 10% hydrochloric acid aqueous solution 142
g, heated to 90°C and hydrolyzed for 3 hours,
The precipitated crystals were filtered, washed with water, and dried to obtain 1.4=diaminoanthraquinone-2.3-dicarboxylic acid anhydride 11.
4g was obtained. Purity was 99%.
実施例2
粗1−アミノー4−ヒドロキシアントラキノン−2.3
−ジカルボン酸無水物(純度50%)200g、ジー(
n−プロビル)アミン120gをメチルセロソルブ2I
!.中、還流下6時間反応した。反応液を室温に冷却し
、不溶物を濾別後、濾液に10%塩酸水溶液118gを
加え、90゜Cに昇温し、3時間加水分解した後、析出
した結晶を濾過、水洗、乾燥して、l−アミノー4−ヒ
ドロキシアントラキノン−2.3−ジカルボン酸無水物
95gを得た.純度は98%であった。Example 2 Crude 1-amino-4-hydroxyanthraquinone-2.3
-Dicarboxylic anhydride (purity 50%) 200g, G(
120 g of n-proyl)amine was added to methyl cellosolve 2I.
! .. The mixture was reacted under reflux for 6 hours. After cooling the reaction solution to room temperature and filtering off insoluble matter, 118 g of a 10% aqueous hydrochloric acid solution was added to the filtrate, and the temperature was raised to 90°C and hydrolyzed for 3 hours. The precipitated crystals were filtered, washed with water, and dried. Thus, 95 g of l-amino-4-hydroxyanthraquinone-2,3-dicarboxylic anhydride was obtained. Purity was 98%.
実施例3Example 3
Claims (1)
4は各々独立に水素原子、アミノ基、水酸基を表わす。 )で示される酸無水物を溶媒中、下記一般式(II)▲数
式、化学式、表等があります▼(II) (式(II)中、R^1及びR^2は各々独立に炭素数1
〜10のアルキル基、アルコキシアルキル基、又はヒド
ロキシアルキル基を表わす。) で示される2級アミンと反応させて、下記 一般式(III) ▲数式、化学式、表等があります▼(III) (式(III)中、Y^1、Y^2、Y^3及びY^4は
、式( I )のY^1、Y^2、Y^3、Y^4と同一
であり、R^1及びR^2は式(II)のR^1、R^2
と同一である。) で表される化合物とし、反応液を濾過して不溶物を除き
、濾液に酸を加えて加水分解することを特徴とする式(
1)で示される酸無水物の精製法。[Claims] 1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In formula (I), T^1, Y^2, Y^3, and Y^
Each of 4 independently represents a hydrogen atom, an amino group, or a hydroxyl group. ) in a solvent, the following general formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (In formula (II), R^1 and R^2 each independently represent the number of carbon atoms. 1
~10 alkyl, alkoxyalkyl, or hydroxyalkyl groups. ) by reacting with a secondary amine represented by the following general formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) (In formula (III), Y^1, Y^2, Y^3 and Y^4 is the same as Y^1, Y^2, Y^3, Y^4 in formula (I), and R^1 and R^2 are R^1, R^2 in formula (II)
is the same as ), the reaction solution is filtered to remove insoluble matter, and the filtrate is hydrolyzed by adding an acid to the formula (
A method for purifying the acid anhydride shown in 1).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30640389A JPH03167181A (en) | 1989-11-28 | 1989-11-28 | Purification of carboxylic acid anhydride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30640389A JPH03167181A (en) | 1989-11-28 | 1989-11-28 | Purification of carboxylic acid anhydride |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03167181A true JPH03167181A (en) | 1991-07-19 |
JPH0575751B2 JPH0575751B2 (en) | 1993-10-21 |
Family
ID=17956598
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30640389A Granted JPH03167181A (en) | 1989-11-28 | 1989-11-28 | Purification of carboxylic acid anhydride |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03167181A (en) |
-
1989
- 1989-11-28 JP JP30640389A patent/JPH03167181A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPH0575751B2 (en) | 1993-10-21 |
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