JP4665431B2 - ビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法 - Google Patents
ビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法 Download PDFInfo
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- JP4665431B2 JP4665431B2 JP2004134390A JP2004134390A JP4665431B2 JP 4665431 B2 JP4665431 B2 JP 4665431B2 JP 2004134390 A JP2004134390 A JP 2004134390A JP 2004134390 A JP2004134390 A JP 2004134390A JP 4665431 B2 JP4665431 B2 JP 4665431B2
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- Prior art keywords
- bpda
- dehydrated product
- biphenyltetracarboxylic acid
- acid heat
- producing
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- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 title claims description 29
- 239000013078 crystal Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000002834 transmittance Methods 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 72
- 238000000034 method Methods 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 238000004040 coloring Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 229920001721 polyimide Polymers 0.000 description 9
- 239000009719 polyimide resin Substances 0.000 description 9
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JSBBGWWJLQNXNQ-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 JSBBGWWJLQNXNQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- -1 biphenyltricarboxylic anhydride Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- KBJBEBLYDFKOFE-UHFFFAOYSA-N tetramethyl 5-phenylbenzene-1,2,3,4-tetracarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)C(C(=O)OC)=CC(C=2C=CC=CC=2)=C1C(=O)OC KBJBEBLYDFKOFE-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Description
ダブルヘリカルリボン翼、ジャケット、不活性ガス供給口を備えた円筒縦型の反応器に、100重量部のBTCを仕込み、攪拌しつつ、常圧下、215℃の温度に加熱し、2m3/hrの速度で窒素ガスを流通し、生成する水をパージしながら脱水閉環反応を10時間行った。
実施例1において、蒸発時の温度を307℃、圧力400Pa、蒸気線速0.4m/秒とした以外は、実施例1と同様の操作を行いBPDAフレークを得た。得られたBPDAの光透過率は98%であった。また、このBPDAのPd含有量を測定すると0.05ppmであった。
実施例1において、脱水閉環反応後、蒸発操作を行わずBPDAを取り出した。得られたBPDAの透過率は78%であり、Pd含有量は0.5ppmであった。
Claims (4)
- ビフェニルテトラカルボン酸加熱無水化生成物を加熱溶融させた後、減圧下、系内の酸素濃度を5ppm以下に保ちながら蒸発させ、高純度ビフェニルテトラカルボン酸二無水物の蒸気を冷却し結晶化することにより、2規定のNaOH水溶液にビフェニルテトラカルボン酸加熱無水化生成物を0.05g/mlの濃度に溶解して得られた溶液に対する波長400nmの光透過率が90%以上であるビフェニルテトラカルボン酸加熱無水化生成物結晶を得ることを特徴とするビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法。
- 波長400nmの光透過率が95%以上である請求項1に記載のビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法。
- 0.5kPa以下の減圧下で蒸発させる請求項1又は2に記載のビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法。
- 307℃以上330℃以下の温度で蒸発させる請求項1〜3の何れかに記載のビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法。
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JP2004134390A JP4665431B2 (ja) | 2004-04-28 | 2004-04-28 | ビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法 |
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JP2004134390A JP4665431B2 (ja) | 2004-04-28 | 2004-04-28 | ビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法 |
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JP2005314296A JP2005314296A (ja) | 2005-11-10 |
JP4665431B2 true JP4665431B2 (ja) | 2011-04-06 |
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JP2004134390A Expired - Lifetime JP4665431B2 (ja) | 2004-04-28 | 2004-04-28 | ビフェニルテトラカルボン酸加熱無水化生成物結晶の製造方法 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR102361736B1 (ko) | 2010-07-22 | 2022-02-14 | 우베 고산 가부시키가이샤 | 폴리이미드 전구체, 폴리이미드 및 그 제조에 사용되는 재료 |
JP7254469B2 (ja) * | 2018-09-12 | 2023-04-10 | Ube株式会社 | ポリイミド及びポリイミド前駆体 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61249977A (ja) * | 1985-04-30 | 1986-11-07 | Mitsubishi Chem Ind Ltd | 高純度ビフエニルテトラカルボン酸二無水物の製法 |
JPH01299282A (ja) * | 1988-05-25 | 1989-12-04 | Mitsubishi Kasei Corp | ビフェニルテトラカルボン酸二無水物の安定化方法 |
JPH08134056A (ja) * | 1994-11-11 | 1996-05-28 | Mitsubishi Chem Corp | 高純度ビフェニルテトラカルボン酸二無水物およびその製造法 |
JPH08143480A (ja) * | 1994-11-16 | 1996-06-04 | Mitsubishi Chem Corp | 高融点有機化合物の精製方法 |
-
2004
- 2004-04-28 JP JP2004134390A patent/JP4665431B2/ja not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61249977A (ja) * | 1985-04-30 | 1986-11-07 | Mitsubishi Chem Ind Ltd | 高純度ビフエニルテトラカルボン酸二無水物の製法 |
JPH01299282A (ja) * | 1988-05-25 | 1989-12-04 | Mitsubishi Kasei Corp | ビフェニルテトラカルボン酸二無水物の安定化方法 |
JPH08134056A (ja) * | 1994-11-11 | 1996-05-28 | Mitsubishi Chem Corp | 高純度ビフェニルテトラカルボン酸二無水物およびその製造法 |
JPH08143480A (ja) * | 1994-11-16 | 1996-06-04 | Mitsubishi Chem Corp | 高融点有機化合物の精製方法 |
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