CA2657173A1 - Procede de preparation de cyanurate de triallyle - Google Patents
Procede de preparation de cyanurate de triallyle Download PDFInfo
- Publication number
- CA2657173A1 CA2657173A1 CA002657173A CA2657173A CA2657173A1 CA 2657173 A1 CA2657173 A1 CA 2657173A1 CA 002657173 A CA002657173 A CA 002657173A CA 2657173 A CA2657173 A CA 2657173A CA 2657173 A1 CA2657173 A1 CA 2657173A1
- Authority
- CA
- Canada
- Prior art keywords
- allyl alcohol
- cyanuric chloride
- reaction
- acid acceptor
- process according
- 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.)
- Abandoned
Links
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 122
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 30
- 241001550224 Apha Species 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 150000007973 cyanuric acids Chemical class 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000005191 phase separation Methods 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 230000000779 depleting effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- 239000000370 acceptor Substances 0.000 description 22
- 238000001816 cooling Methods 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006034257.7 | 2006-07-21 | ||
| DE102006034257.7A DE102006034257B4 (de) | 2006-07-21 | 2006-07-21 | Verfahren zur Herstellung von Triallylcyanurat |
| PCT/EP2007/056316 WO2008009540A1 (fr) | 2006-07-21 | 2007-06-25 | Procédé de préparation de cyanurate de triallyle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2657173A1 true CA2657173A1 (fr) | 2008-01-24 |
Family
ID=38788845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002657173A Abandoned CA2657173A1 (fr) | 2006-07-21 | 2007-06-25 | Procede de preparation de cyanurate de triallyle |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP2044039A1 (fr) |
| JP (1) | JP2009544642A (fr) |
| KR (1) | KR20090031583A (fr) |
| CN (1) | CN101490020A (fr) |
| AU (1) | AU2007276289A1 (fr) |
| BR (1) | BRPI0714504A2 (fr) |
| CA (1) | CA2657173A1 (fr) |
| DE (1) | DE102006034257B4 (fr) |
| IL (1) | IL194803A0 (fr) |
| MX (1) | MX2008015260A (fr) |
| RU (1) | RU2009105820A (fr) |
| WO (1) | WO2008009540A1 (fr) |
| ZA (1) | ZA200900459B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011066679A1 (fr) | 2009-12-01 | 2011-06-09 | Cytec Surface Specialties, S.A. | Revetements pour substrats en ceramique |
| ES2632783T3 (es) | 2014-12-19 | 2017-09-15 | Evonik Degussa Gmbh | Sistemas de redes de cubierta para láminas de encapsulación que comprenden compuestos de bis-(alquenilamidas) |
| ES2635260T3 (es) | 2014-12-19 | 2017-10-03 | Evonik Degussa Gmbh | Sistemas correticulantes para láminas de encapsulado que comprenden compuestos de urea |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2631148A (en) * | 1953-03-10 | Manufacture of triallyl cyanurate | ||
| US2510564A (en) * | 1946-10-02 | 1950-06-06 | American Cyanamid Co | Triallyl cyanurate and insecticidal compositions containing the same |
| US3635969A (en) * | 1969-04-26 | 1972-01-18 | Musashino Kagaku Kenkyujyo Kk | Process for the production of triallyl cyanurate |
| US3644410A (en) * | 1970-02-27 | 1972-02-22 | Ciba Geigy Corp | Preparation of triallyl cyanurate |
-
2006
- 2006-07-21 DE DE102006034257.7A patent/DE102006034257B4/de active Active
-
2007
- 2007-06-25 MX MX2008015260A patent/MX2008015260A/es not_active Application Discontinuation
- 2007-06-25 CN CNA2007800272305A patent/CN101490020A/zh active Pending
- 2007-06-25 RU RU2009105820/04A patent/RU2009105820A/ru not_active Application Discontinuation
- 2007-06-25 KR KR1020097001221A patent/KR20090031583A/ko not_active Application Discontinuation
- 2007-06-25 JP JP2009521181A patent/JP2009544642A/ja active Pending
- 2007-06-25 WO PCT/EP2007/056316 patent/WO2008009540A1/fr active Application Filing
- 2007-06-25 AU AU2007276289A patent/AU2007276289A1/en not_active Abandoned
- 2007-06-25 CA CA002657173A patent/CA2657173A1/fr not_active Abandoned
- 2007-06-25 EP EP07786835A patent/EP2044039A1/fr not_active Withdrawn
- 2007-06-25 BR BRPI0714504-7A patent/BRPI0714504A2/pt not_active IP Right Cessation
-
2008
- 2008-10-22 IL IL194803A patent/IL194803A0/en unknown
-
2009
- 2009-01-20 ZA ZA200900459A patent/ZA200900459B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE102006034257A1 (de) | 2008-01-31 |
| AU2007276289A1 (en) | 2008-01-24 |
| ZA200900459B (en) | 2010-01-27 |
| CN101490020A (zh) | 2009-07-22 |
| DE102006034257B4 (de) | 2014-11-27 |
| EP2044039A1 (fr) | 2009-04-08 |
| WO2008009540A1 (fr) | 2008-01-24 |
| MX2008015260A (es) | 2008-12-17 |
| BRPI0714504A2 (pt) | 2012-12-25 |
| IL194803A0 (en) | 2009-09-22 |
| JP2009544642A (ja) | 2009-12-17 |
| RU2009105820A (ru) | 2010-08-27 |
| KR20090031583A (ko) | 2009-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |