JPS61249977A - 高純度ビフエニルテトラカルボン酸二無水物の製法 - Google Patents
高純度ビフエニルテトラカルボン酸二無水物の製法Info
- Publication number
- JPS61249977A JPS61249977A JP9087785A JP9087785A JPS61249977A JP S61249977 A JPS61249977 A JP S61249977A JP 9087785 A JP9087785 A JP 9087785A JP 9087785 A JP9087785 A JP 9087785A JP S61249977 A JPS61249977 A JP S61249977A
- Authority
- JP
- Japan
- Prior art keywords
- dianhydride
- acid
- reduced pressure
- crystals
- heating
- 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
- 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 title claims description 56
- 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 21
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims description 37
- 239000013078 crystal Substances 0.000 claims description 34
- 238000010438 heat treatment Methods 0.000 claims description 22
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- -1 phosphoric acid Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GDVVYWWFZVDULK-UHFFFAOYSA-N tetracene-1-carbaldehyde Chemical compound C1=CC=C2C=C(C=C3C(C=O)=CC=CC3=C3)C3=CC2=C1 GDVVYWWFZVDULK-UHFFFAOYSA-N 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
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9087785A JPS61249977A (ja) | 1985-04-30 | 1985-04-30 | 高純度ビフエニルテトラカルボン酸二無水物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9087785A JPS61249977A (ja) | 1985-04-30 | 1985-04-30 | 高純度ビフエニルテトラカルボン酸二無水物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61249977A true JPS61249977A (ja) | 1986-11-07 |
| JPH0437078B2 JPH0437078B2 (enrdf_load_stackoverflow) | 1992-06-18 |
Family
ID=14010702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9087785A Granted JPS61249977A (ja) | 1985-04-30 | 1985-04-30 | 高純度ビフエニルテトラカルボン酸二無水物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61249977A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6450876A (en) * | 1987-08-21 | 1989-02-27 | Ube Industries | Production of high-purity biphenyltetracarboxylic acid dianhydride |
| JPH01104063A (ja) * | 1987-06-25 | 1989-04-21 | Ube Ind Ltd | 高純度ビフェニルテトラカルボン酸二無水物の製法 |
| JPH0374379A (ja) * | 1989-08-14 | 1991-03-28 | Mitsubishi Kasei Corp | ビフェニルテトラカルボン酸二無水物の製造法 |
| US5047560A (en) * | 1989-10-06 | 1991-09-10 | Hitachi, Ltd. | Process for producing highly pure 3,3',4,4'-biphenyltetracarboxylic acid or dianhydride thereof |
| JP2005314296A (ja) * | 2004-04-28 | 2005-11-10 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸加熱無水化生成物結晶 |
| JP2005314297A (ja) * | 2004-04-28 | 2005-11-10 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸加熱無水化生成物結晶 |
| JP2006045198A (ja) * | 2004-06-28 | 2006-02-16 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸二無水物及びその製造方法、並びにこれを用いたポリイミド及びその製造方法 |
| US7459570B2 (en) | 2002-03-13 | 2008-12-02 | Mitsubishi Chemical Corporation | High-purity biphenyltetracarboxylic dianhydride and process for producing the same |
| JP2012017339A (ja) * | 2004-06-28 | 2012-01-26 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸二無水物及びその製造方法、並びにこれを用いたポリイミド及びその製造方法 |
| JP2021042153A (ja) * | 2019-09-10 | 2021-03-18 | Ｊｆｅケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911862A (enrdf_load_stackoverflow) * | 1972-05-19 | 1974-02-01 |
-
1985
- 1985-04-30 JP JP9087785A patent/JPS61249977A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911862A (enrdf_load_stackoverflow) * | 1972-05-19 | 1974-02-01 |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01104063A (ja) * | 1987-06-25 | 1989-04-21 | Ube Ind Ltd | 高純度ビフェニルテトラカルボン酸二無水物の製法 |
| JPS6450876A (en) * | 1987-08-21 | 1989-02-27 | Ube Industries | Production of high-purity biphenyltetracarboxylic acid dianhydride |
| JPH0374379A (ja) * | 1989-08-14 | 1991-03-28 | Mitsubishi Kasei Corp | ビフェニルテトラカルボン酸二無水物の製造法 |
| US5047560A (en) * | 1989-10-06 | 1991-09-10 | Hitachi, Ltd. | Process for producing highly pure 3,3',4,4'-biphenyltetracarboxylic acid or dianhydride thereof |
| US7459570B2 (en) | 2002-03-13 | 2008-12-02 | Mitsubishi Chemical Corporation | High-purity biphenyltetracarboxylic dianhydride and process for producing the same |
| JP2005314296A (ja) * | 2004-04-28 | 2005-11-10 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸加熱無水化生成物結晶 |
| JP2005314297A (ja) * | 2004-04-28 | 2005-11-10 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸加熱無水化生成物結晶 |
| JP2006045198A (ja) * | 2004-06-28 | 2006-02-16 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸二無水物及びその製造方法、並びにこれを用いたポリイミド及びその製造方法 |
| JP2012017339A (ja) * | 2004-06-28 | 2012-01-26 | Mitsubishi Chemicals Corp | ビフェニルテトラカルボン酸二無水物及びその製造方法、並びにこれを用いたポリイミド及びその製造方法 |
| US8299273B2 (en) | 2004-06-28 | 2012-10-30 | Mitsubishi Chemical Corporation | Biphenyltetracarboxylic acid dianhydride and process for producing the same, and polyimide formed from the same and process for producing the same |
| US8492565B2 (en) | 2004-06-28 | 2013-07-23 | Mitsubishi Chemical Corporation | Biphenyltetracarboxylic acid dianhydride and process for producing the same, and polyimide formed from the same and process for producing the same |
| JP2021042153A (ja) * | 2019-09-10 | 2021-03-18 | Ｊｆｅケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0437078B2 (enrdf_load_stackoverflow) | 1992-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |