JPH06107599A - Production of aromatic dicarboxlic acid monoester compounds - Google Patents
Production of aromatic dicarboxlic acid monoester compoundsInfo
- Publication number
- JPH06107599A JPH06107599A JP28668692A JP28668692A JPH06107599A JP H06107599 A JPH06107599 A JP H06107599A JP 28668692 A JP28668692 A JP 28668692A JP 28668692 A JP28668692 A JP 28668692A JP H06107599 A JPH06107599 A JP H06107599A
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- aromatic dicarboxylic
- acid monoester
- alkali metal
- producing
- 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
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 title abstract description 8
- 239000002253 acid Substances 0.000 title description 6
- -1 aromatic dicarboxylic acid diester compound Chemical class 0.000 claims abstract description 46
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 12
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- SCTKUAQEXBPGKY-UHFFFAOYSA-N diethyl naphthalene-2,7-dicarboxylate Chemical compound C1=CC(C(=O)OCC)=CC2=CC(C(=O)OCC)=CC=C21 SCTKUAQEXBPGKY-UHFFFAOYSA-N 0.000 claims description 2
- WYIBAMPRACRCOM-UHFFFAOYSA-N dimethyl naphthalene-2,7-dicarboxylate Chemical compound C1=CC(C(=O)OC)=CC2=CC(C(=O)OC)=CC=C21 WYIBAMPRACRCOM-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000009434 installation Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- JGJWEXOAAXEJMW-UHFFFAOYSA-N dimethyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JGJWEXOAAXEJMW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000010992 reflux Methods 0.000 description 3
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000003916 acid precipitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- CSNCOKSAYUDNIE-UHFFFAOYSA-N diethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=CC2=CC(C(=O)OCC)=CC=C21 CSNCOKSAYUDNIE-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- UISIYYCJKZNXDU-UHFFFAOYSA-L disodium;naphthalene-2,6-dicarboxylate Chemical compound [Na+].[Na+].C1=C(C([O-])=O)C=CC2=CC(C(=O)[O-])=CC=C21 UISIYYCJKZNXDU-UHFFFAOYSA-L 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- DVFQIAPMVGKBIN-UHFFFAOYSA-M sodium;7-methoxycarbonylnaphthalene-2-carboxylate Chemical compound [Na+].C1=CC(C([O-])=O)=CC2=CC(C(=O)OC)=CC=C21 DVFQIAPMVGKBIN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GSYIVQLTSZFJRV-UHFFFAOYSA-N 3-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1 GSYIVQLTSZFJRV-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- LIKHRLCRYVOFEK-UHFFFAOYSA-N 4-(4-methoxycarbonylphenyl)benzoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(O)=O)C=C1 LIKHRLCRYVOFEK-UHFFFAOYSA-N 0.000 description 1
- QLHYQXZUBDTQCJ-UHFFFAOYSA-N 6-ethoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)OCC)=CC=C21 QLHYQXZUBDTQCJ-UHFFFAOYSA-N 0.000 description 1
- SKTKMAWOMQFTNS-UHFFFAOYSA-N 6-methoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)OC)=CC=C21 SKTKMAWOMQFTNS-UHFFFAOYSA-N 0.000 description 1
- GFUSLUJZIDIKSK-UHFFFAOYSA-N 7-methoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)OC)=CC=C21 GFUSLUJZIDIKSK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- BKRIRZXWWALTPU-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)OC)C=C1 BKRIRZXWWALTPU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-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
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【産業上の利用分野】本発明は、各種中間体として有用
な芳香族ジカルボン酸モノエステル類を製造する方法の
改良に関する。FIELD OF THE INVENTION The present invention relates to an improvement in a method for producing aromatic dicarboxylic acid monoesters useful as various intermediates.
【０００２】[0002]
【従来の技術】一般に、ジカルボン酸モノエステル類の
製造方法としては、該ジカルボン酸を酸触媒を用いてア
ルコール類でエステル化するか又はジアルキル硫酸また
はスルホン酸アルキルエステル類でエステル化する方
法、ジカルボン酸ジエステル類を水酸化カリウム等のア
ルカリ水酸化物やナトリウムメチラート等のアルコラー
ト類と反応させて加水分解する方法等が知られ（例えば
特開平３−２２３２３１号公報等に記載の従来技術）、
又、ナフタレンジカルボン酸モノエステル類の製造方法
としてはメチルナフタレンモノカルボン酸アルキルエス
テル類の核メチル基を酸化してナフタレンジカルボン酸
モノエステル類を得る方法が知られている。2. Description of the Related Art Generally, a dicarboxylic acid monoester is produced by esterifying the dicarboxylic acid with an alcohol using an acid catalyst or with a dialkyl sulfuric acid or an alkyl sulfonate. Known is a method of reacting an acid diester with an alkali hydroxide such as potassium hydroxide or an alcoholate such as sodium methylate to hydrolyze the same (for example, a conventional technique described in JP-A-3-223231),
As a method for producing naphthalenedicarboxylic acid monoesters, a method is known in which a naphthalenedicarboxylic acid monoester is obtained by oxidizing a nucleus methyl group of methylnaphthalene monocarboxylic acid alkyl ester.
【０００３】しかしながら、該エステル化により芳香族
ジカルボン酸モノエステル類を製造する場合には一般に
選択率が悪く、工業的、実用的でない。また該芳香族ジ
カルボン酸ジエステル類を加水分解して芳香族ジカルボ
ン酸モノエステル類を製造する従来の方法では目的とす
るモノエステルの選択率が低く、かつ精製しても高純度
の目的物を得ることは容易でない等の問題があった。更
に、前記メチルナフタレンモノカルボン酸アルキルエス
テル類の酸化による方法は比較的高純度のモノエステル
類を得る事が出来るが、特殊な専用の設備を必要とする
等、工業的に有利ではない等の問題がある。However, when the aromatic dicarboxylic acid monoesters are produced by the esterification, the selectivity is generally poor and it is not industrially or practically used. Further, in the conventional method of producing aromatic dicarboxylic acid monoesters by hydrolyzing the aromatic dicarboxylic acid diesters, the selectivity of the desired monoester is low, and a highly pure target product is obtained even after purification. There were problems such as not being easy. Furthermore, the method by oxidation of the methylnaphthalene monocarboxylic acid alkyl ester can obtain a relatively high purity monoester, but it requires a special dedicated equipment, which is not industrially advantageous. There's a problem.
【０００４】[0004]
【発明が解決しようとする課題】本発明者らは上記の問
題点に鑑み、入手容易な化合物を出発物質として用い、
特殊な製造設備を必要としないで工業的に有利に芳香族
ジカルボン酸モノエステル類を高収率、高純度で製造す
る方法について鋭意研究、検討の結果、特定の有機溶媒
中で、特定の試剤を用いて加水分解反応を行うことによ
り所期の目的を都合良く達成することを見出し、本発明
を完成するに至った。In view of the above problems, the present inventors have used a readily available compound as a starting material,
As a result of diligent research and study on a method for industrially producing aromatic dicarboxylic acid monoesters in high yield and high purity without requiring special production equipment, as a result, a specific reagent was used in a specific organic solvent. The inventors have found that the intended purpose can be conveniently achieved by carrying out a hydrolysis reaction using, and have completed the present invention.
【０００５】[0005]
【課題を解決するための手段】本発明は、芳香族ジカル
ボン酸ジエステル類を加水分解して芳香族ジカルボン酸
モノエステル類を製造するに際し、該芳香族ジカルボン
酸ジエステル類を溶解し、芳香族ジカルボン酸モノエス
テル類のアルカリ金属塩を実質的に溶解しない有機溶媒
中で、アルカリ金属アルコラートと水を用いて加水分解
することを特徴とする芳香族ジカルボン酸モノエステル
類の製造方法である。DISCLOSURE OF THE INVENTION In the present invention, when an aromatic dicarboxylic acid diester is hydrolyzed to produce an aromatic dicarboxylic acid monoester, the aromatic dicarboxylic acid diester is dissolved to obtain an aromatic dicarboxylic acid diester. A method for producing an aromatic dicarboxylic acid monoester, which comprises hydrolyzing an alkali metal salt of an acid monoester with an alkali metal alcoholate and water in an organic solvent that does not substantially dissolve the salt.
【０００６】本発明の方法の特徴は、加水分解反応によ
って、選択的に該芳香族ジカルボン酸モノエステル類の
アルカリ金属塩を得ることにある。芳香族ジカルボン酸
ジエステル類を従来の方法で加水分解する場合、途中で
得られる該ジカルボン酸モノエステル類は、該ジエステ
ル類よりも水への溶解度が大きくなり、該ジエステル類
よりも先に加水分解を受けてフリーのジカルボン酸とな
り易く、モノカルボン酸類を選択的に得ることは困難で
あった。A feature of the method of the present invention is that the alkali metal salt of the aromatic dicarboxylic acid monoester is selectively obtained by a hydrolysis reaction. When an aromatic dicarboxylic acid diester is hydrolyzed by a conventional method, the dicarboxylic acid monoester obtained in the middle has a higher solubility in water than the diester and is hydrolyzed prior to the diester. Accordingly, free dicarboxylic acid is easily obtained, and it has been difficult to selectively obtain monocarboxylic acids.
【０００７】しかるに、本発明者等は、該加水分解反応
を、該芳香族ジカルボン酸ジエステル類を溶解し、芳香
族ジカルボン酸モノエステル類のアルカリ金属塩を実質
的に溶解しない有機溶媒中で行うことにより、芳香族ジ
カルボン酸モノエステル類のアルカリ金属塩が選択的に
結晶として析出させることができ、これがフリーのジカ
ルボン酸への副反応を抑制し、目的とする芳香族ジカル
ボン酸モノエステル類が選択的に高収率、高純度で得ら
れることを見出した。However, the present inventors carry out the hydrolysis reaction in an organic solvent which dissolves the aromatic dicarboxylic acid diesters and does not substantially dissolve the alkali metal salt of the aromatic dicarboxylic acid monoester. As a result, the alkali metal salt of the aromatic dicarboxylic acid monoester can be selectively precipitated as crystals, which suppresses the side reaction to the free dicarboxylic acid, and the target aromatic dicarboxylic acid monoester is It was found that high yield and high purity can be selectively obtained.
【０００８】本発明の方法に用いられる芳香族ジカルボ
ン酸ジエステル類としては、具体的にはフタル酸、イソ
フタル酸、テレフタル酸、1,4-ナフタレンジカルボン
酸、1,5-ナフタレンジカルボン酸、1,8-ナフタレンジカ
ルボン酸、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、4,4'- ビフェニルジカルボン酸、3,3'
- ビフェニルジカルボン酸、3,4'- ビフェニルジカルボ
ン酸等の芳香族ジカルボン酸の脂肪族または芳香族アル
コールのエステル類が挙げられる。また、これらのエス
テル類の芳香環は更に他の置換基で置換されていてもよ
い。Specific examples of the aromatic dicarboxylic acid diesters used in the method of the present invention include phthalic acid, isophthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1, 8-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 4,4'-biphenyldicarboxylic acid, 3,3 '
— Esters of aliphatic or aromatic alcohols of aromatic dicarboxylic acids such as biphenyldicarboxylic acid and 3,4′-biphenyldicarboxylic acid. The aromatic ring of these esters may be further substituted with other substituents.
【０００９】これらの中でも、2,6-ナフタレンジカルボ
ン酸ジメチルエステル、2,6-ナフタレンジカルボン酸ジ
エチルエステル、2,7-ナフタレンジカルボン酸ジメチル
エステル又は2,7-ナフタレンジカルボン酸ジエチルエス
テル等のナフタレンジカルボン酸ジエステル類又はフタ
ル酸、イソフタル酸又はテレフタル酸等のベンゼンジカ
ルボン酸ジエステル類が本発明の方法に特に好ましく適
用される。Among these, naphthalenedicarboxylic acid such as 2,6-naphthalenedicarboxylic acid dimethyl ester, 2,6-naphthalenedicarboxylic acid diethyl ester, 2,7-naphthalenedicarboxylic acid dimethyl ester or 2,7-naphthalenedicarboxylic acid diethyl ester. Acid diesters or benzenedicarboxylic acid diesters such as phthalic acid, isophthalic acid or terephthalic acid are particularly preferably applied to the process according to the invention.
【００１０】本発明の方法に用いられる芳香族ジカルボ
ン酸ジエステル類を溶解し、かつ芳香族ジカルボン酸モ
ノエステル類のアルカリ金属塩を実質的に溶解しない有
機溶媒としては、具体的には次のような有機溶媒が挙げ
られる。Specific examples of the organic solvent used in the method of the present invention, which dissolves the aromatic dicarboxylic acid diesters and does not substantially dissolve the alkali metal salt of the aromatic dicarboxylic acid monoester, are as follows. Organic solvents.
【００１１】ベンゼン、トルエン、キシレン等の芳香族
炭化水素類、クロルベンゼン、ジクロルエタン、トリク
ロルエタン等のハロゲン化炭化水素類、ジブチルエーテ
ル、プロピルエーテル等のエーテル類、メチルエチルケ
トン、メチルイソブチルケトン等のケトン類又はニトロ
ベンゼン類等。これらの中でも、芳香族炭化水素類、ハ
ロゲン化炭化水素類が本発明の方法に好ましく適用され
る。Aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chlorobenzene, dichloroethane and trichloroethane, ethers such as dibutyl ether and propyl ether, ketones such as methyl ethyl ketone and methyl isobutyl ketone. Or nitrobenzenes etc. Among these, aromatic hydrocarbons and halogenated hydrocarbons are preferably applied to the method of the present invention.
【００１２】これらの有機溶媒の使用量は、特に制限的
ではないが、その量が少なすぎると芳香族ジカルボン酸
ジエステル類が完全に溶解せず、また生成したモノエス
テル類のスラリー濃度が高くなり攪拌が困難になる等の
問題が生じ、一方あまり多すぎると工業的に製造のため
の容積効率が低下する等、いずれも好ましくない。有機
溶媒の使用量の適切な範囲は、実験的に容易に決めるこ
とが出来る。The amount of these organic solvents used is not particularly limited, but if the amount is too small, the aromatic dicarboxylic acid diesters are not completely dissolved, and the slurry concentration of the produced monoesters becomes high. Problems such as difficulty in stirring occur, and too much amount is not preferable because the volumetric efficiency for manufacturing industrially decreases. The appropriate range of the amount of the organic solvent used can be easily determined experimentally.
【００１３】本発明の方法に用いられるアルカリ金属ア
ルコラートとしては、通常炭素数１〜４の低級アルコー
ルのアルカリ金属アルコラートが用いられる。具体的に
はソジウムメチラート、カリウムメチラート、ソジウム
エチラート、カリウムエチラート、ソジウムブチラート
等である。これらのアルカリ金属アルコラートは、メタ
ノール、エタノール等の有機溶剤に溶解した溶液の形で
用いることができる。As the alkali metal alcoholate used in the method of the present invention, an alkali metal alcoholate of a lower alcohol having 1 to 4 carbon atoms is usually used. Specific examples include sodium methylate, potassium methylate, sodium ethylate, potassium ethylate, sodium butyrate, and the like. These alkali metal alcoholates can be used in the form of a solution dissolved in an organic solvent such as methanol or ethanol.
【００１４】本発明の方法において、アルカリ金属アル
コラートの使用量は特に制限的ではないが、通常、芳香
族ジカルボン酸ジエステル類１モルに対して０．５〜
１．５モルの範囲、好ましくは０．９〜１．１モルの範
囲で行われる。In the method of the present invention, the amount of the alkali metal alcoholate used is not particularly limited, but is usually 0.5 to 1 mol per 1 mol of the aromatic dicarboxylic acid diester.
It is carried out in the range of 1.5 mol, preferably in the range of 0.9 to 1.1 mol.
【００１５】本発明の方法において用いる水は反応系に
均一に分散されていることが好ましく、アルコール等の
水溶性の有機溶媒に希釈して用いたり、時には界面活性
剤を併用添加することができる。The water used in the method of the present invention is preferably uniformly dispersed in the reaction system, and may be diluted with a water-soluble organic solvent such as alcohol or used in combination with a surfactant. .
【００１６】本発明の加水分解反応における水は、水単
独又はアルコール等の水溶性溶剤の水溶液の形で用いら
れ、その量は、加水分解の程度に影響するが、通常、芳
香族ジカルボン酸ジエステル類１モルに対して０．５〜
１．５モルの範囲、好ましくは０．９〜１．１モルの範
囲で行われる。水の量が少なすぎると使用した芳香族ジ
カルボン酸ジエステル類の一部しか転換できないため反
応効率が悪くなり、逆に多すぎるとジカルボン酸塩類の
生成量が多くなり、モノエステル類の純度が低下する傾
向を示す。Water in the hydrolysis reaction of the present invention is used in the form of water alone or an aqueous solution of a water-soluble solvent such as alcohol, and the amount thereof usually affects the degree of hydrolysis, but is usually an aromatic dicarboxylic acid diester. 0.5 to 1 mol
It is carried out in the range of 1.5 mol, preferably in the range of 0.9 to 1.1 mol. If the amount of water is too small, only a part of the used aromatic dicarboxylic acid diesters can be converted, resulting in poor reaction efficiency.On the other hand, if the amount of water is too large, the amount of dicarboxylic acid salts produced increases and the purity of monoesters decreases. Shows the tendency to
【００１７】本発明の方法における反応温度についても
特に制限的ではないが、通常、２０〜１５０℃の範囲、
好ましくは５０〜１００℃で行われる。また、反応時間
は通常、０．５〜８時間で終了する。The reaction temperature in the method of the present invention is not particularly limited, but is usually in the range of 20 to 150 ° C.,
It is preferably carried out at 50 to 100 ° C. The reaction time is usually 0.5 to 8 hours.
【００１８】本発明の方法の好ましい実施態様は、出発
原料の芳香族ジカルボン酸ジエステル類を芳香族炭化水
素又はハロゲン化炭化水素類に溶解し、これにアルカリ
金属アルコラートを好ましくはアルコール溶液の形で加
え、次いで必要な水をアルコール水溶液の形で除々に添
加し、所定時間加温攪拌して加水分解反応を完結させる
ことにより行われる。かくして芳香族ジカルボン酸モノ
エステル類のアルカリ金属塩が結晶として析出される。A preferred embodiment of the process according to the invention is to dissolve the starting aromatic dicarboxylic acid diesters in aromatic hydrocarbons or halogenated hydrocarbons, to which the alkali metal alcoholate, preferably in the form of an alcoholic solution. Then, the necessary water is gradually added in the form of an aqueous alcohol solution, and the mixture is heated and stirred for a predetermined time to complete the hydrolysis reaction. Thus, the alkali metal salt of an aromatic dicarboxylic acid monoester is precipitated as crystals.
【００１９】本発明の方法によって得られる芳香族ジカ
ルボン酸モノエステルのアルカリ金属塩は、反応液を濾
過して反応に用いた有機溶媒及び反応で生じたアルコー
ル類から分離したり、反応液に温水を加えて抽出分離
し、晶析、濾過することにより容易に得られる。The alkali metal salt of the aromatic dicarboxylic acid monoester obtained by the method of the present invention is separated from the organic solvent used in the reaction and the alcohols generated in the reaction by filtering the reaction solution, or in the reaction solution with warm water. It can be easily obtained by adding and separating and separating, crystallization and filtration.
【００２０】以上、本発明の方法によって得られる芳香
族ジカルボン酸モノエステルのアルカリ金属塩はそのま
までも充分高い純度を保持しているが、必要に応じて水
又は水と水溶性のアルコール類、エーテル類、ケトン
類、ニトリル化合物等との混合溶媒中で再結晶精製する
ことにより精製することが出来る。As described above, the alkali metal salt of the aromatic dicarboxylic acid monoester obtained by the method of the present invention retains sufficiently high purity as it is, but if necessary, water or water-soluble alcohols and ethers are used. It can be purified by recrystallization purification in a mixed solvent with a compound, a ketone, a nitrile compound and the like.
【００２１】本発明の方法によって得られた芳族ジカル
ボン酸モノエステルのアルカリ金属塩は、通常の方法に
よってこれを塩酸や硫酸などの酸を用いて酸析すること
により、極めて高純度のフリー酸の形の芳香族ジカルボ
ン酸モノエステル類に転換することが出来る。The alkali metal salt of an aromatic dicarboxylic acid monoester obtained by the method of the present invention is an extremely high-purity free acid obtained by acidifying it with an acid such as hydrochloric acid or sulfuric acid by a conventional method. It can be converted to aromatic dicarboxylic acid monoesters of the form:
【００２２】[0022]
【発明の効果】本発明の方法によれば、入手容易な化合
物を出発物質として用い、特殊な製造設備を必要としな
いで工業的に有利に芳香族ジカルボン酸モノエステル類
を高収率、高純度で製造することができ、その工業的利
用価値は極めて大きいものがある。Industrial Applicability According to the method of the present invention, an easily obtainable compound is used as a starting material, and an aromatic dicarboxylic acid monoester is industrially advantageous in a high yield and a high yield without requiring special production equipment. It can be produced with a high degree of purity and its industrial utility value is extremely high.
【００２３】[0023]
【実施例】以下に実施例を挙げ、本発明を具体的に説明
するが、これ等の例は本発明を限定するものではない。
なお、比較の為に、本発明に特定する有機溶媒を用いな
い場合、或いは本発明に特定するアルカリ試剤を用いな
い場合について、比較例として示した。EXAMPLES The present invention will be specifically described below with reference to examples, but these examples do not limit the present invention.
For comparison, the case where the organic solvent specified in the present invention is not used or the alkali reagent specified in the present invention is not used is shown as a comparative example.
【００２４】実施例１ 攪拌器及び還流冷却器を備えた 500mlフラスコに、 2,7
- ナフタレンジカルボン酸ジメチルエステル 15.7g と
トルエン 165mlを仕込み溶解する。28％ソジウムメチラ
ート 12.5gを加えた後、70％メタノール水 3.9g を滴下
し、60〜68℃で１時間保温攪拌した。室温まで冷却後、
濾過し、2,7-ナフタレンジカルボン酸モノメチルエステ
ルソジウム塩 16g を得た。この物を液体クロマトグラ
フィーで分析した結果、純度 95 ％であった。更に、90
mlの水で再結晶して、純度 99.8％の 2,7- ナフタレン
ジカルボン酸モノメチルエステルソジウム塩が 13g得ら
れた。次いで、2 ％塩酸水 100g 中で酸析し、2,7-ナフ
タレンジカルボン酸モノメチルエステル 11.8g を得
た。この物の純度は 99.8 ％で、収率は 78.9 ％であっ
た。Example 1 A 500 ml flask equipped with a stirrer and a reflux condenser was charged with 2,7
-Charge and dissolve 15.7g of naphthalenedicarboxylic acid dimethyl ester and 165ml of toluene. After adding 12.5 g of 28% sodium methylate, 3.9 g of 70% methanol water was added dropwise, and the mixture was heated and stirred at 60 to 68 ° C for 1 hour. After cooling to room temperature,
After filtration, 16 g of 2,7-naphthalenedicarboxylic acid monomethyl ester sodium salt was obtained. As a result of analyzing the product by liquid chromatography, the purity was 95%. Furthermore, 90
The crystals were recrystallized from ml of water to obtain 13 g of 2,7-naphthalenedicarboxylic acid monomethyl ester sodium salt having a purity of 99.8%. Then, acid precipitation was carried out in 100 g of 2% hydrochloric acid water to obtain 11.8 g of 2,7-naphthalenedicarboxylic acid monomethyl ester. The purity of this product was 99.8%, and the yield was 78.9%.
【００２５】実施例２ 実施例１と同様の反応器に 2,6- ナフタレンジカルボン
酸ジメチルエステル 15.7gとトルエン165ml を仕込み溶
解する。28％ソジウムメチラート 12.5gを加えた後、90
％メタノール水を11.7g 滴下し、60〜68℃で３時間保温
攪拌した。室温まで冷却後、濾過し、2,6-ナフタレンジ
カルボン酸モノメチルエステルソジウム塩 16g を得
た。この物を液体クロマトグラフィーで分析した結果、
純度95 ％であった。更に、90ml の水で再結晶して、
純度 99.8 ％の 2,6- ナフタレンジカルボン酸モノメチ
ルエステルソジウム塩が 14.5g 得られた。次いで、2.
5 ％塩酸水 100g 中で酸析し、2,6-ナフタレンジカルボ
ン酸モノメチルエステル 13.2g を得た。この物の純度
は99.8％で、収率は 88.0 ％であった。Example 2 In a reactor similar to that of Example 1, 15.7 g of 2,6-naphthalenedicarboxylic acid dimethyl ester and 165 ml of toluene were charged and dissolved. After adding 12.5 g of 28% sodium methylate, 90
11.7 g of% methanol water was added dropwise, and the mixture was heated and stirred at 60 to 68 ° C for 3 hours. After cooling to room temperature, filtration was performed to obtain 16 g of 2,6-naphthalenedicarboxylic acid monomethyl ester sodium salt. As a result of analyzing this product by liquid chromatography,
The purity was 95%. Furthermore, recrystallize with 90 ml of water,
14.5 g of 2,6-naphthalenedicarboxylic acid monomethyl ester sodium salt having a purity of 99.8% was obtained. Then 2.
Acid precipitation was performed in 100 g of 5% hydrochloric acid water to obtain 13.2 g of 2,6-naphthalenedicarboxylic acid monomethyl ester. The purity of this product was 99.8%, and the yield was 88.0%.
【００２６】実施例３ 実施例１と同様の反応器に 2,6- ナフタレンジカルボン
酸ジエチルエステル 27.0g とクロルベンゼン 200ml
を仕込み溶解する。ソジウムエチラート 4.4gを加えた
後、70％エタノール水を3.9g 滴下し、60〜65℃で４時
間保温攪拌した。以下、実施例１と同様の操作により、
2,6-ナフタレンジカルボン酸モノエチルエステル 11.9g
を得た。この物の純度は 99.0 ％で、収率は 75 ％であ
った。Example 3 A reactor similar to that used in Example 1 was charged with 27.0 g of 2,6-naphthalenedicarboxylic acid diethyl ester and 200 ml of chlorobenzene.
Charge and dissolve. After adding 4.4 g of sodium ethylate, 3.9 g of 70% aqueous ethanol was added dropwise, and the mixture was heated and stirred at 60 to 65 ° C for 4 hours. Hereinafter, by the same operation as in Example 1,
2,6-Naphthalenedicarboxylic acid monoethyl ester 11.9g
Got The purity of this product was 99.0%, and the yield was 75%.
【００２７】実施例４ 実施例１と同様にして、テレフタル酸ジメチルエステル
より、テレフタル酸モノメチルエステルを得た。純度は
99.5 ％で、収率は 70 ％であった。Example 4 In the same manner as in Example 1, terephthalic acid monomethyl ester was obtained from terephthalic acid dimethyl ester. Purity is
It was 99.5% and the yield was 70%.
【００２８】実施例５ 実施例１と同様にして、4,4'- ビフェニルジカルボン酸
ジメチルエステルより、4,4'- ビフェニルジカルボン酸
モノメチルエステルを得た。純度は 99.4 ％で、収率は
81 ％であった。Example 5 In the same manner as in Example 1, 4,4′-biphenyldicarboxylic acid monomethyl ester was obtained from 4,4′-biphenyldicarboxylic acid dimethyl ester. The purity is 99.4% and the yield is
It was 81%.
【００２９】比較例１ 攪拌器及び還流冷却器を備えた 500mlフラスコに 2,6-
ナフタレンジカルボン酸ジメチルエステル 15.7gとジメ
チルスルホキサイド 100g を仕込み溶解する。98％苛性
曹達 2.65g を加えた後、100 ℃で２時間保温攪拌した
反応物を分析したところ、2,6-ナフタレンジカルボン酸
モノメチルエステルソジウム塩の転換率は 38.7 ％で、
未反応 2,6- ナフタレンジカルボン酸ジメチルエステル
が 51.0％、 2,6- ナフタレンジカルボン酸ジソジウム
塩が 9.6％であった。Comparative Example 1 2,6-in a 500 ml flask equipped with a stirrer and a reflux condenser.
Charge 15.7 g of naphthalenedicarboxylic acid dimethyl ester and 100 g of dimethyl sulfoxide and dissolve. After adding 2.65 g of 98% caustic soda, and then analyzing the reaction product which was stirred at 100 ° C. for 2 hours, the conversion of 2,6-naphthalenedicarboxylic acid monomethyl ester sodium salt was 38.7%.
Unreacted 2,6-naphthalenedicarboxylic acid dimethyl ester was 51.0% and 2,6-naphthalenedicarboxylic acid disodium salt was 9.6%.
【００３０】比較例２ 攪拌器及び還流冷却器を備えた 1000ml フラスコに 2,6
- ナフタレンジカルボン酸ジメチルエステル 15.7g と
メタノール 600g を仕込み溶解する。28％ソジウムメチ
ラート 12.5g を加えた後、65℃で９時間保温攪拌した
反応物を分析したところ、2,6-ナフタレンジカルボン酸
モノメチルエステルソジウム塩の転換率は 39.3 ％で、
未反応 2,6- ナフタレンジカルボン酸ジメチルエステル
が 40.2％、 2,6- ナフタレンジカルボン酸ジソジウム
塩が 19.8 ％であった。Comparative Example 2 2,6 in a 1000 ml flask equipped with stirrer and reflux condenser.
-Charge and dissolve 15.7g of naphthalenedicarboxylic acid dimethyl ester and 600g of methanol. After adding 12.5 g of 28% sodium methylate and analyzing the reaction product which was heated and stirred at 65 ° C. for 9 hours, the conversion of 2,6-naphthalenedicarboxylic acid monomethyl ester sodium salt was 39.3%.
Unreacted 2,6-naphthalenedicarboxylic acid dimethyl ester was 40.2% and 2,6-naphthalenedicarboxylic acid disodium salt was 19.8%.
Claims (8)
分解して芳香族ジカルボン酸モノエステル類を製造する
に際し、該芳香族ジカルボン酸ジエステル類を溶解し、
芳香族ジカルボン酸モノエステル類のアルカリ金属塩を
実質的に溶解しない有機溶媒中で、アルカリ金属アルコ
ラートと水を用いて加水分解することを特徴とする芳香
族ジカルボン酸モノエステル類の製造方法。1. When hydrolyzing an aromatic dicarboxylic acid diester to produce an aromatic dicarboxylic acid monoester, the aromatic dicarboxylic acid diester is dissolved,
1. A method for producing an aromatic dicarboxylic acid monoester, which comprises hydrolyzing an alkali metal salt of an aromatic dicarboxylic acid monoester with an alkali metal alcoholate and water in a substantially insoluble organic solvent.
し、芳香族ジカルボン酸モノエステル類のアルカリ金属
塩を実質的に溶解しない有機溶媒が、芳香族炭化水素
類、ハロゲン化炭化水素類から選ばれる請求項１に記載
の芳香族ジカルボン酸モノエステル類の製造方法。2. The organic solvent that dissolves the aromatic dicarboxylic acid diesters and does not substantially dissolve the alkali metal salt of the aromatic dicarboxylic acid monoester is selected from aromatic hydrocarbons and halogenated hydrocarbons. The method for producing an aromatic dicarboxylic acid monoester according to claim 1.
〜４の低級脂肪族アルコールのアルカリ金属アルコラー
トである請求項１又は請求項２のいずれかに記載の芳香
族ジカルボン酸モノエステル類の製造方法。3. The alkali metal alcoholate has 1 carbon atom.
4. The method for producing an aromatic dicarboxylic acid monoester according to claim 1, which is an alkali metal alcoholate of a lower aliphatic alcohol according to claim 4.
ムから選ばれる請求項１に記載の芳香族ジカルボン酸モ
ノエステル類の製造方法。4. The method for producing an aromatic dicarboxylic acid monoester according to claim 1, wherein the alkali metal is selected from sodium and potassium.
ンゼンジカルボン酸ジエステル類又はナフタレンジカル
ボン酸ジエステル類である請求項１〜請求項４のいずれ
かに記載の芳香族ジカルボン酸モノエステル類の製造方
法。5. The method for producing an aromatic dicarboxylic acid monoester according to claim 1, wherein the aromatic dicarboxylic acid diester is benzene dicarboxylic acid diester or naphthalene dicarboxylic acid diester.
が、2,6-ナフタレンジカルボン酸ジメチルエステル、2,
6-ナフタレンジカルボン酸ジエチルエステル、2,7-ナフ
タレンジカルボン酸ジメチルエステル及び2,7-ナフタレ
ンジカルボン酸ジエチルエステルから選ばれる請求項５
に記載の芳香族ジカルボン酸モノエステル類の製造方
法。6. The naphthalene dicarboxylic acid diesters are 2,6-naphthalene dicarboxylic acid dimethyl ester, 2,
6. A selected from 6-naphthalenedicarboxylic acid diethyl ester, 2,7-naphthalenedicarboxylic acid dimethyl ester and 2,7-naphthalenedicarboxylic acid diethyl ester.
The method for producing an aromatic dicarboxylic acid monoester according to 1.
分解して芳香族ジカルボン酸モノエステル類を製造する
に際し、該芳香族ジカルボン酸ジエステル類を溶解し、
芳香族ジカルボン酸モノエステル類のアルカリ金属塩を
実質的に溶解しない有機溶媒中で、アルカリ金属アルコ
ラートと水を用いて加水分解し、芳香族ジカルボン酸モ
ノエステル類のアルカリ金属塩として得ることを特徴と
する芳香族ジカルボン酸モノエステル類の製造方法。7. When producing an aromatic dicarboxylic acid monoester by hydrolyzing an aromatic dicarboxylic acid diester, the aromatic dicarboxylic acid diester is dissolved,
Characterized by obtaining an alkali metal salt of an aromatic dicarboxylic acid monoester by hydrolysis using an alkali metal alcoholate and water in an organic solvent that does not substantially dissolve the aromatic dicarboxylic acid monoester. And a method for producing an aromatic dicarboxylic acid monoester.
ルカリ金属塩を、水又は水と有機溶剤との混合溶媒中で
再結晶精製する請求項７に記載の芳香族ジカルボン酸モ
ノエステル類の製造方法。 【０００１】8. The method for producing an aromatic dicarboxylic acid monoester according to claim 7, wherein the alkali metal salt of the aromatic dicarboxylic acid monoester is purified by recrystallization in water or a mixed solvent of water and an organic solvent. . [0001]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28668692A JPH06107599A (en) | 1992-09-30 | 1992-09-30 | Production of aromatic dicarboxlic acid monoester compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28668692A JPH06107599A (en) | 1992-09-30 | 1992-09-30 | Production of aromatic dicarboxlic acid monoester compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06107599A true JPH06107599A (en) | 1994-04-19 |
Family
ID=17707665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28668692A Pending JPH06107599A (en) | 1992-09-30 | 1992-09-30 | Production of aromatic dicarboxlic acid monoester compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06107599A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008526781A (en) * | 2005-02-22 | 2008-07-24 | テバ ファーマシューティカル インダストリーズ リミティド | Manufacture of rosuvastatin |
| EP3521269A1 (en) | 2018-02-06 | 2019-08-07 | Clariant Plastics & Coatings Ltd | Process for preparation of 1-nitrobenzene-2-alkyloxycarbonyl-5-carboxylic acid |
| CN114773192A (en) * | 2022-05-23 | 2022-07-22 | 煤炭科学技术研究院有限公司 | Method for continuously preparing 2, 6-dimethyl naphthalenedicarboxylate slices |
-
1992
- 1992-09-30 JP JP28668692A patent/JPH06107599A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008526781A (en) * | 2005-02-22 | 2008-07-24 | テバ ファーマシューティカル インダストリーズ リミティド | Manufacture of rosuvastatin |
| EP3521269A1 (en) | 2018-02-06 | 2019-08-07 | Clariant Plastics & Coatings Ltd | Process for preparation of 1-nitrobenzene-2-alkyloxycarbonyl-5-carboxylic acid |
| WO2019154728A1 (en) | 2018-02-06 | 2019-08-15 | Clariant Plastics & Coatings Ltd | Process for preparation of 1-nitrobenzene-2-alkyloxycarbonyl-5-carboxylic acid |
| CN114773192A (en) * | 2022-05-23 | 2022-07-22 | 煤炭科学技术研究院有限公司 | Method for continuously preparing 2, 6-dimethyl naphthalenedicarboxylate slices |
| CN114773192B (en) * | 2022-05-23 | 2023-09-26 | 煤炭科学技术研究院有限公司 | Method for continuously preparing 2, 6-dimethyl naphthalene dicarboxylate slices |
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