JPH0437078B2 - - Google Patents
Info
- Publication number
- JPH0437078B2 JPH0437078B2 JP60090877A JP9087785A JPH0437078B2 JP H0437078 B2 JPH0437078 B2 JP H0437078B2 JP 60090877 A JP60090877 A JP 60090877A JP 9087785 A JP9087785 A JP 9087785A JP H0437078 B2 JPH0437078 B2 JP H0437078B2
- Authority
- JP
- Japan
- Prior art keywords
- biphenyltetracarboxylic dianhydride
- biphenyltetracarboxylic
- dianhydride
- crystals
- reduced pressure
- 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.)
- Expired - Lifetime
Links
- 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 claims description 68
- 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 55
- 239000013078 crystal Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 37
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012535 impurity Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 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 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 230000006837 decompression Effects 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 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 Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 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 JPS61249977A (ja) | 1986-11-07 |
JPH0437078B2 true JPH0437078B2 (US07582779-20090901-C00044.png) | 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 (US07582779-20090901-C00044.png) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0762013B2 (ja) * | 1987-06-25 | 1995-07-05 | 宇部興産株式会社 | 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 |
JP2503079B2 (ja) * | 1989-08-14 | 1996-06-05 | 三菱化学株式会社 | ビフェニルテトラカルボン酸二無水物の製造法 |
JP2735314B2 (ja) * | 1989-10-06 | 1998-04-02 | 株式会社日立製作所 | 高純度の3,3’,4,4’―ビフェニルテトラカルボン酸又はその酸二無水物の製造方法 |
JP2003335768A (ja) | 2002-03-13 | 2003-11-28 | Mitsubishi Chemicals 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方法 |
JP4665431B2 (ja) * | 2004-04-28 | 2011-04-06 | 三菱化学株式会社 | 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 |
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 |
WO2006001443A1 (ja) | 2004-06-28 | 2006-01-05 | Mitsubishi Chemical Corporation | 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 |
JP7083793B2 (ja) * | 2019-09-10 | 2022-06-13 | 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 (US07582779-20090901-C00044.png) * | 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 (US07582779-20090901-C00044.png) * | 1972-05-19 | 1974-02-01 |
Also Published As
Publication number | Publication date |
---|---|
JPS61249977A (ja) | 1986-11-07 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EXPY | Cancellation because of completion of term |