JP5851250B2 - 環状カーボネート構造を有する新規なホスフィン酸エステル化合物およびその製造方法 - Google Patents
環状カーボネート構造を有する新規なホスフィン酸エステル化合物およびその製造方法 Download PDFInfo
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- JP5851250B2 JP5851250B2 JP2012005428A JP2012005428A JP5851250B2 JP 5851250 B2 JP5851250 B2 JP 5851250B2 JP 2012005428 A JP2012005428 A JP 2012005428A JP 2012005428 A JP2012005428 A JP 2012005428A JP 5851250 B2 JP5851250 B2 JP 5851250B2
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- hetero atom
- cyclic carbonate
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- -1 ester compound Chemical class 0.000 title claims description 41
- 150000005676 cyclic carbonates Chemical group 0.000 title claims description 33
- 238000000034 method Methods 0.000 title description 3
- 230000008569 process Effects 0.000 title description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 35
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- 125000000732 arylene group Chemical group 0.000 claims description 22
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000002485 combustion reaction Methods 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 8
- 229920005668 polycarbonate resin Polymers 0.000 description 8
- 239000004431 polycarbonate resin Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 150000008040 ionic compounds Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- GLOYZWKUEDKTFX-UHFFFAOYSA-N CC(C)(c1cc(OCC2OC2)ccc1)c1cccc(OCC2OC2)c1 Chemical compound CC(C)(c1cc(OCC2OC2)ccc1)c1cccc(OCC2OC2)c1 GLOYZWKUEDKTFX-UHFFFAOYSA-N 0.000 description 1
- ZLQIECOKZQXHIT-UHFFFAOYSA-N CC(C)(c1cccc(OCC(COc(ccc(OCC(O)Oc2cccc(C(C)(C)c3cc(OCC(CO4)OC4=O)ccc3)c2)c2)c2P2(Oc(cccc3)c3-c3c2cccc3)=O)O)c1)c1cc(OCC(CO2)OC2=O)ccc1 Chemical compound CC(C)(c1cccc(OCC(COc(ccc(OCC(O)Oc2cccc(C(C)(C)c3cc(OCC(CO4)OC4=O)ccc3)c2)c2)c2P2(Oc(cccc3)c3-c3c2cccc3)=O)O)c1)c1cc(OCC(CO2)OC2=O)ccc1 ZLQIECOKZQXHIT-UHFFFAOYSA-N 0.000 description 1
- DZJJDVWJIDEDGX-UHFFFAOYSA-N CC(C)(c1cccc(OCC(COc(ccc(OCC(O)Oc2cccc(C(C)(C)c3cc(OCC4OC4)ccc3)c2)c2)c2P2(Oc(cccc3)c3-c3c2cccc3)=O)O)c1)c1cccc(OCC2OC2)c1 Chemical compound CC(C)(c1cccc(OCC(COc(ccc(OCC(O)Oc2cccc(C(C)(C)c3cc(OCC4OC4)ccc3)c2)c2)c2P2(Oc(cccc3)c3-c3c2cccc3)=O)O)c1)c1cccc(OCC2OC2)c1 DZJJDVWJIDEDGX-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- KMRIWYPVRWEWRG-UHFFFAOYSA-N Oc(cc1P2(Oc(cccc3)c3-c3c2cccc3)=O)ccc1O Chemical compound Oc(cc1P2(Oc(cccc3)c3-c3c2cccc3)=O)ccc1O KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- YJSXLGKPMXKZJR-UHFFFAOYSA-N ethoxy-oxo-phenylphosphanium Chemical compound CCO[P+](=O)C1=CC=CC=C1 YJSXLGKPMXKZJR-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KUQFDYRHDBNMSI-UHFFFAOYSA-M triethyl(2-hydroxyethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CCO KUQFDYRHDBNMSI-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012005428A JP5851250B2 (ja) | 2012-01-13 | 2012-01-13 | 環状カーボネート構造を有する新規なホスフィン酸エステル化合物およびその製造方法 |
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| JP2012005428A JP5851250B2 (ja) | 2012-01-13 | 2012-01-13 | 環状カーボネート構造を有する新規なホスフィン酸エステル化合物およびその製造方法 |
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| Publication Number | Publication Date |
|---|---|
| JP2013144653A JP2013144653A (ja) | 2013-07-25 |
| JP2013144653A5 JP2013144653A5 (enExample) | 2015-02-05 |
| JP5851250B2 true JP5851250B2 (ja) | 2016-02-03 |
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| JP2012005428A Expired - Fee Related JP5851250B2 (ja) | 2012-01-13 | 2012-01-13 | 環状カーボネート構造を有する新規なホスフィン酸エステル化合物およびその製造方法 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110475799A (zh) * | 2017-04-14 | 2019-11-19 | 沙特基础工业全球技术有限公司 | 含磷单体的合成及通过界面聚合将其并入到聚碳酸酯 |
| CN111793091A (zh) * | 2020-09-04 | 2020-10-20 | 中国科学院宁波材料技术与工程研究所 | 无卤阻燃环氧树脂前驱体、组合物、模塑料制品、制法及应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773070A (en) * | 1952-10-31 | 1956-12-04 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| DE2344197A1 (de) * | 1973-09-01 | 1975-03-27 | Dynamit Nobel Ag | Funktionelle organophosphonsaeureester als konservierende haftvermittler oder ueberzuege fuer metalle |
| DE19819586A1 (de) * | 1998-04-30 | 1999-11-04 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von 1,3-Dioxolan-2-onen |
| TWI449707B (zh) * | 2008-07-15 | 2014-08-21 | Univ Nat Chunghsing | 新穎磷系雙酚及其衍生物之製造方法 |
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| Publication number | Publication date |
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| JP2013144653A (ja) | 2013-07-25 |
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