JPH0319225B2 - - Google Patents
Info
- Publication number
- JPH0319225B2 JPH0319225B2 JP61078169A JP7816986A JPH0319225B2 JP H0319225 B2 JPH0319225 B2 JP H0319225B2 JP 61078169 A JP61078169 A JP 61078169A JP 7816986 A JP7816986 A JP 7816986A JP H0319225 B2 JPH0319225 B2 JP H0319225B2
- Authority
- JP
- Japan
- Prior art keywords
- maleimide
- weight
- carbon dioxide
- pressure
- temperature
- 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 82
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 66
- 239000001569 carbon dioxide Substances 0.000 claims description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 26
- 239000012043 crude product Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 21
- -1 amine compound Chemical class 0.000 description 16
- MFBWWGXSZLGPRU-UHFFFAOYSA-N 1-octadec-1-enylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CN1C(=O)C=CC1=O MFBWWGXSZLGPRU-UHFFFAOYSA-N 0.000 description 15
- 239000000539 dimer Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- KIKBJYQCJJXCBZ-UHFFFAOYSA-N 1-octylpyrrole-2,5-dione Chemical compound CCCCCCCCN1C(=O)C=CC1=O KIKBJYQCJJXCBZ-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- PZQWVKKXPIZFHC-UHFFFAOYSA-N 1-decylpyrrole-2,5-dione Chemical compound CCCCCCCCCCN1C(=O)C=CC1=O PZQWVKKXPIZFHC-UHFFFAOYSA-N 0.000 description 1
- GHPSXHPCIXRTFW-UHFFFAOYSA-N 1-dodec-1-enylpyrrole-2,5-dione Chemical compound CCCCCCCCCCC=CN1C(=O)C=CC1=O GHPSXHPCIXRTFW-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- KZCSJWFLPQFDNW-UHFFFAOYSA-N 1-ethenylpyrrole-2,5-dione Chemical compound C=CN1C(=O)C=CC1=O KZCSJWFLPQFDNW-UHFFFAOYSA-N 0.000 description 1
- UMUNOXKIUHCIIR-UHFFFAOYSA-N 1-heptadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O UMUNOXKIUHCIIR-UHFFFAOYSA-N 0.000 description 1
- COEKMFUFXAWJGI-UHFFFAOYSA-N 1-heptylpyrrole-2,5-dione Chemical compound CCCCCCCN1C(=O)C=CC1=O COEKMFUFXAWJGI-UHFFFAOYSA-N 0.000 description 1
- QKMBVFKXQWIKOZ-UHFFFAOYSA-N 1-hexadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCN1C(=O)C=CC1=O QKMBVFKXQWIKOZ-UHFFFAOYSA-N 0.000 description 1
- FBPVUBVZRPURIU-UHFFFAOYSA-N 1-hexylpyrrole-2,5-dione Chemical compound CCCCCCN1C(=O)C=CC1=O FBPVUBVZRPURIU-UHFFFAOYSA-N 0.000 description 1
- NXPHNRSAYBXVMF-UHFFFAOYSA-N 1-icosylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O NXPHNRSAYBXVMF-UHFFFAOYSA-N 0.000 description 1
- ROEZFSDXTWGAQU-UHFFFAOYSA-N 1-nonadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O ROEZFSDXTWGAQU-UHFFFAOYSA-N 0.000 description 1
- UNJAMUMWPRRGHF-UHFFFAOYSA-N 1-nonylpyrrole-2,5-dione Chemical compound CCCCCCCCCN1C(=O)C=CC1=O UNJAMUMWPRRGHF-UHFFFAOYSA-N 0.000 description 1
- HOLZCMFSCBLOLX-UHFFFAOYSA-N 1-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O HOLZCMFSCBLOLX-UHFFFAOYSA-N 0.000 description 1
- JHKVBRBZDVWQOE-UHFFFAOYSA-N 1-pentadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCN1C(=O)C=CC1=O JHKVBRBZDVWQOE-UHFFFAOYSA-N 0.000 description 1
- CZUQOPAKOZMIPQ-UHFFFAOYSA-N 1-pentylpyrrole-2,5-dione Chemical compound CCCCCN1C(=O)C=CC1=O CZUQOPAKOZMIPQ-UHFFFAOYSA-N 0.000 description 1
- XJVXUUFIBPLYFK-UHFFFAOYSA-N 1-prop-1-enylpyrrole-2,5-dione Chemical compound CC=CN1C(=O)C=CC1=O XJVXUUFIBPLYFK-UHFFFAOYSA-N 0.000 description 1
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 1
- FDQMDCGTDRRHJO-UHFFFAOYSA-N 1-tetradecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCN1C(=O)C=CC1=O FDQMDCGTDRRHJO-UHFFFAOYSA-N 0.000 description 1
- AACVWGWQMWGCFL-UHFFFAOYSA-N 1-tridecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCN1C(=O)C=CC1=O AACVWGWQMWGCFL-UHFFFAOYSA-N 0.000 description 1
- SGWFSFTYSPSADW-UHFFFAOYSA-N 1-undecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCN1C(=O)C=CC1=O SGWFSFTYSPSADW-UHFFFAOYSA-N 0.000 description 1
- VOYQCFMGTRPFKT-UHFFFAOYSA-N 3-octylpyrrole-2,5-dione Chemical compound CCCCCCCCC1=CC(=O)NC1=O VOYQCFMGTRPFKT-UHFFFAOYSA-N 0.000 description 1
- OCKONLRSFDLRRU-UHFFFAOYSA-N C(=CCCC)N1C(C=CC1=O)=O Chemical compound C(=CCCC)N1C(C=CC1=O)=O OCKONLRSFDLRRU-UHFFFAOYSA-N 0.000 description 1
- RSBQNXCLOVEWFN-UHFFFAOYSA-N CCC=CN1C(=O)C=CC1=O Chemical compound CCC=CN1C(=O)C=CC1=O RSBQNXCLOVEWFN-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61078169A JPS62238262A (ja) | 1986-04-07 | 1986-04-07 | マレイミドの精製方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61078169A JPS62238262A (ja) | 1986-04-07 | 1986-04-07 | マレイミドの精製方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62238262A JPS62238262A (ja) | 1987-10-19 |
| JPH0319225B2 true JPH0319225B2 (enrdf_load_stackoverflow) | 1991-03-14 |
Family
ID=13654434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61078169A Granted JPS62238262A (ja) | 1986-04-07 | 1986-04-07 | マレイミドの精製方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62238262A (enrdf_load_stackoverflow) |
-
1986
- 1986-04-07 JP JP61078169A patent/JPS62238262A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62238262A (ja) | 1987-10-19 |
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