JPH0585547B2 - - Google Patents
Info
- Publication number
- JPH0585547B2 JPH0585547B2 JP59144534A JP14453484A JPH0585547B2 JP H0585547 B2 JPH0585547 B2 JP H0585547B2 JP 59144534 A JP59144534 A JP 59144534A JP 14453484 A JP14453484 A JP 14453484A JP H0585547 B2 JPH0585547 B2 JP H0585547B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dichlorophenyl
- formula
- oxazolidine
- dione
- 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
- 239000012452 mother liquor Substances 0.000 claims abstract description 35
- MHXGWLFBKYHUAF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1,3-oxazolidine-2,4-dione Chemical class ClC1=CC(Cl)=CC(N2C(OCC2=O)=O)=C1 MHXGWLFBKYHUAF-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000007514 bases Chemical class 0.000 claims abstract 2
- -1 glycolic acid ester Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 15
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 238000010923 batch production Methods 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract description 2
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- PQTSIDUQCMERIC-UHFFFAOYSA-N 2-[(3,5-dichlorophenyl)carbamoyloxy]acetic acid Chemical compound OC(=O)COC(=O)NC1=CC(Cl)=CC(Cl)=C1 PQTSIDUQCMERIC-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002893 slag Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- CSBPGCNNCFKIHE-UHFFFAOYSA-N 2-methylpropyl 2-hydroxy-2-methylbut-3-enoate Chemical compound CC(C)COC(=O)C(C)(O)C=C CSBPGCNNCFKIHE-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
- FTCOKXNKPOUEFH-UHFFFAOYSA-N Myclozolin Chemical compound O=C1C(COC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FTCOKXNKPOUEFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- IRASIIUXVCHHAC-UHFFFAOYSA-N 2-carbamoyloxyacetic acid Chemical compound NC(=O)OCC(O)=O IRASIIUXVCHHAC-UHFFFAOYSA-N 0.000 description 1
- LNYCRXIGNQFREW-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-1,3-oxazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(C(C=C)OC2=O)=O)=C1 LNYCRXIGNQFREW-UHFFFAOYSA-N 0.000 description 1
- QTUFXYHGZCQEGG-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidine-2,4-dione Chemical compound C=CN1C(=O)COC1=O QTUFXYHGZCQEGG-UHFFFAOYSA-N 0.000 description 1
- DJSVMPNEEYAXEY-UHFFFAOYSA-N 5-ethenyl-1,3-oxazolidine-2,4-dione Chemical compound C=CC1OC(=O)NC1=O DJSVMPNEEYAXEY-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NRXAIHXPAWGHMH-UHFFFAOYSA-N butyl 2-hydroxy-2-methylbut-3-enoate Chemical compound CCCCOC(=O)C(C)(O)C=C NRXAIHXPAWGHMH-UHFFFAOYSA-N 0.000 description 1
- FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
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| DE19833325734 DE3325734A1 (de) | 1983-07-16 | 1983-07-16 | Verfahren zur herstellung von n-(3,5-dichlorphenyl)-oxazolidin-2,4-dionen |
| DE3325734.5 | 1983-07-16 |
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| JPS6064973A JPS6064973A (ja) | 1985-04-13 |
| JPH0585547B2 true JPH0585547B2 (ja) | 1993-12-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP59144534A Granted JPS6064973A (ja) | 1983-07-16 | 1984-07-13 | âïŒïŒïŒïŒâãžã¯ãã«ããšãã«ïŒâãªããµãŸãªãžã³âïŒïŒïŒâãžãªã³ã®è£œé æ³ |
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| EP (1) | EP0131903B1 (ja) |
| JP (1) | JPS6064973A (ja) |
| AT (1) | ATE37542T1 (ja) |
| DE (2) | DE3325734A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07308915A (ja) * | 1994-05-19 | 1995-11-28 | Goei Seisakusho:Kk | æ¶é³ã«ãã¿ãŒ |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6160122A (en) * | 1996-06-28 | 2000-12-12 | Abbott Laboratories | Process for the preparation of a disubstituted thiazole |
| FR2751965B1 (fr) * | 1996-08-01 | 1998-11-27 | Oreal | Nouveaux composes de la famille des aryl-2,4-dioxo-oxazolidines |
| ES2218026T3 (es) * | 1997-12-11 | 2004-11-16 | Bayer Materialscience Ag | Dispersion acuosa que contiene un poliisocianato de superficie desactivada. |
| DE19924138A1 (de) | 1999-05-26 | 2000-11-30 | Henkel Kgaa | Lösbare Klebeverbindungen |
| DE19951599A1 (de) | 1999-10-27 | 2001-05-23 | Henkel Kgaa | Verfahren zur adhesiven Trennung von Klebeverbunden |
| DE10037884A1 (de) | 2000-08-03 | 2002-02-21 | Henkel Kgaa | Verfahren zur beschleunigten KlebstoffaushÀrtung |
| GB2400104B (en) | 2003-04-03 | 2007-10-10 | Bostik Findley Ltd | Storage stable adhesive paste compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL123189C (ja) * | 1963-09-18 | |||
| DE2324591C2 (de) * | 1973-05-16 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Oxazolidin-Derivate |
| DE2813873A1 (de) * | 1978-03-31 | 1979-10-11 | Basf Ag | Verfahren zur herstellung von oxazolidin-2,4-dionen |
| DE3014119A1 (de) * | 1980-04-12 | 1981-10-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von n-(3,5-dichlorphenyl)-oxazolidin-2,4-dionen |
-
1983
- 1983-07-16 DE DE19833325734 patent/DE3325734A1/de not_active Withdrawn
-
1984
- 1984-07-11 DE DE8484108131T patent/DE3474302D1/de not_active Expired
- 1984-07-11 EP EP84108131A patent/EP0131903B1/de not_active Expired
- 1984-07-11 AT AT84108131T patent/ATE37542T1/de not_active IP Right Cessation
- 1984-07-13 JP JP59144534A patent/JPS6064973A/ja active Granted
- 1984-07-16 US US06/631,183 patent/US4810799A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07308915A (ja) * | 1994-05-19 | 1995-11-28 | Goei Seisakusho:Kk | æ¶é³ã«ãã¿ãŒ |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3474302D1 (en) | 1988-11-03 |
| ATE37542T1 (de) | 1988-10-15 |
| EP0131903B1 (de) | 1988-09-28 |
| EP0131903A2 (de) | 1985-01-23 |
| EP0131903A3 (en) | 1986-03-05 |
| DE3325734A1 (de) | 1985-01-24 |
| JPS6064973A (ja) | 1985-04-13 |
| US4810799A (en) | 1989-03-07 |
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Legal Events
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| EXPY | Cancellation because of completion of term |