JPH0261956B2 - - Google Patents
Info
- Publication number
- JPH0261956B2 JPH0261956B2 JP58088096A JP8809683A JPH0261956B2 JP H0261956 B2 JPH0261956 B2 JP H0261956B2 JP 58088096 A JP58088096 A JP 58088096A JP 8809683 A JP8809683 A JP 8809683A JP H0261956 B2 JPH0261956 B2 JP H0261956B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- cbda
- maleic anhydride
- solvent
- carried out
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 3
- 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 1
- DKXPPORBGHZJHX-UHFFFAOYSA-N cyclobutane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1(C(O)=O)C(O)=O DKXPPORBGHZJHX-UHFFFAOYSA-N 0.000 claims 1
- 238000011907 photodimerization Methods 0.000 claims 1
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 20
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 description 20
- 238000000034 method Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- -1 aromatic tetracarboxylic acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8809683A JPS59212495A (ja) | 1983-05-19 | 1983-05-19 | １，２，３，４−シクロブタンテトラカルボン酸−１，２「い」３，４−ジ無水物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8809683A JPS59212495A (ja) | 1983-05-19 | 1983-05-19 | １，２，３，４−シクロブタンテトラカルボン酸−１，２「い」３，４−ジ無水物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59212495A JPS59212495A (ja) | 1984-12-01 |
| JPH0261956B2 true JPH0261956B2 (de) | 1990-12-21 |
Family
ID=13933336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8809683A Granted JPS59212495A (ja) | 1983-05-19 | 1983-05-19 | １，２，３，４−シクロブタンテトラカルボン酸−１，２「い」３，４−ジ無水物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59212495A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008273876A (ja) * | 2007-04-27 | 2008-11-13 | Nof Corp | １，２，３，４−シクロブタンテトラカルボン酸の製造方法 |
| WO2009104685A1 (ja) | 2008-02-21 | 2009-08-27 | 日産化学工業株式会社 | レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH085891B2 (ja) * | 1986-08-29 | 1996-01-24 | 大日本インキ化学工業株式会社 | ビシクロ〔２．２．１〕ヘプタン−２，３，５，６−テトラカルボン酸２無水物類およびその製法 |
| JP2775493B2 (ja) * | 1989-10-23 | 1998-07-16 | チッソ株式会社 | アルキル置換シクロブタンテトラカルボン酸二無水物含有組成物、ポリイミド前駆体、硬化膜及びこれらの製造方法 |
| US7374857B2 (en) | 2001-11-30 | 2008-05-20 | Wako Pure Chemical Industries Ltd. | Bismide compound, acid generator and resist composition each containing the same, and method of forming pattern from the composition |
| JP4852206B2 (ja) * | 2001-12-26 | 2012-01-11 | 日産化学工業株式会社 | シクロブタンテトラカルボン酸二無水物化合物の製造法 |
| JP2006347931A (ja) * | 2005-06-15 | 2006-12-28 | Nissan Chem Ind Ltd | ジアルキルシクロブタン酸二無水物及びその製造法 |
| CN102977112A (zh) * | 2012-12-05 | 2013-03-20 | 陕西省石油化工研究设计院 | 一种合成环丁烷四甲酸二酐的工艺方法 |
| KR20210100756A (ko) * | 2014-01-17 | 2021-08-17 | 닛산 가가쿠 가부시키가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
| WO2015108166A1 (ja) | 2014-01-17 | 2015-07-23 | 日産化学工業株式会社 | シクロブタンテトラカルボン酸誘導体の製造方法 |
| WO2015108169A1 (ja) | 2014-01-17 | 2015-07-23 | 日産化学工業株式会社 | シクロブタンテトラカルボン酸誘導体の製造方法 |
| JP6939263B2 (ja) * | 2017-08-29 | 2021-09-22 | Jsr株式会社 | シクロブタン誘導体の製造方法 |
-
1983
- 1983-05-19 JP JP8809683A patent/JPS59212495A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| TETRAHEDRON LETTERS * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008273876A (ja) * | 2007-04-27 | 2008-11-13 | Nof Corp | １，２，３，４−シクロブタンテトラカルボン酸の製造方法 |
| WO2009104685A1 (ja) | 2008-02-21 | 2009-08-27 | 日産化学工業株式会社 | レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59212495A (ja) | 1984-12-01 |
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