DE2552713C3 - Verfahren zur Herstellung von AUyläthern von Phenolen bzw. halogenierten Phenolen - Google Patents
Verfahren zur Herstellung von AUyläthern von Phenolen bzw. halogenierten PhenolenInfo
- Publication number
- DE2552713C3 DE2552713C3 DE19752552713 DE2552713A DE2552713C3 DE 2552713 C3 DE2552713 C3 DE 2552713C3 DE 19752552713 DE19752552713 DE 19752552713 DE 2552713 A DE2552713 A DE 2552713A DE 2552713 C3 DE2552713 C3 DE 2552713C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- reaction
- parts
- phenols
- allyl
- 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
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000002989 phenols Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 allyl ethers Chemical class 0.000 claims description 13
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 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 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VCNJVIWFSMCZPE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-prop-2-enoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(OCC=C)C(Br)=C1Br VCNJVIWFSMCZPE-UHFFFAOYSA-N 0.000 description 1
- CGNVPUNQXISZNA-UHFFFAOYSA-N 1,2,3-tribromo-4-(3,3-dibromopropoxy)benzene Chemical compound BrC(Br)CCOC1=CC=C(Br)C(Br)=C1Br CGNVPUNQXISZNA-UHFFFAOYSA-N 0.000 description 1
- FJNNYLPBIOZVIQ-UHFFFAOYSA-N 1,2,3-tribromo-4-prop-2-enoxybenzene Chemical compound BrC1=CC=C(OCC=C)C(Br)=C1Br FJNNYLPBIOZVIQ-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Chemical class 0.000 description 1
- DILDHOCPBKVXHR-UHFFFAOYSA-N ClC(C(C1=CC=CC=C1)(Br)Br)C(OC(C(C(C1=CC=CC=C1)(Br)Br)Cl)(Br)Br)(Br)Br Chemical compound ClC(C(C1=CC=CC=C1)(Br)Br)C(OC(C(C(C1=CC=CC=C1)(Br)Br)Cl)(Br)Br)(Br)Br DILDHOCPBKVXHR-UHFFFAOYSA-N 0.000 description 1
- PBFQJWQGDRTCLU-UHFFFAOYSA-N ClC(CCOC(C(Br)=C(C(Br)=C1Br)Br)=C1Br)Cl Chemical compound ClC(CCOC(C(Br)=C(C(Br)=C1Br)Br)=C1Br)Cl PBFQJWQGDRTCLU-UHFFFAOYSA-N 0.000 description 1
- MMBVUVNQTGGVJS-UHFFFAOYSA-N [1,1,2,3,3-pentabromo-3-(1,1,2,3,3-pentabromo-3-phenylpropoxy)propyl]benzene Chemical compound C=1C=CC=CC=1C(Br)(Br)C(Br)C(Br)(Br)OC(Br)(Br)C(Br)C(Br)(Br)C1=CC=CC=C1 MMBVUVNQTGGVJS-UHFFFAOYSA-N 0.000 description 1
- GWBWGPRZOYDADH-UHFFFAOYSA-N [C].[Na] Chemical compound [C].[Na] GWBWGPRZOYDADH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DSARFWXDKCYNNI-UHFFFAOYSA-N methanol;phenol Chemical class OC.OC1=CC=CC=C1 DSARFWXDKCYNNI-UHFFFAOYSA-N 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752552713 DE2552713C3 (de) | 1975-11-25 | 1975-11-25 | Verfahren zur Herstellung von AUyläthern von Phenolen bzw. halogenierten Phenolen |
| FR7615129A FR2332970A1 (fr) | 1975-11-25 | 1976-05-19 | Procede de preparation d'ethers allyliques de phenols et de phenols halogenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752552713 DE2552713C3 (de) | 1975-11-25 | 1975-11-25 | Verfahren zur Herstellung von AUyläthern von Phenolen bzw. halogenierten Phenolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2552713A1 DE2552713A1 (de) | 1977-05-26 |
| DE2552713B2 DE2552713B2 (de) | 1978-10-12 |
| DE2552713C3 true DE2552713C3 (de) | 1979-06-07 |
Family
ID=5962515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752552713 Expired DE2552713C3 (de) | 1975-11-25 | 1975-11-25 | Verfahren zur Herstellung von AUyläthern von Phenolen bzw. halogenierten Phenolen |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2552713C3 (enExample) |
| FR (1) | FR2332970A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060563A (en) * | 1976-10-18 | 1977-11-29 | The Firestone Tire & Rubber Company | Process for preparing 2-allyl phenol |
| IT1140948B (it) * | 1980-05-16 | 1986-10-10 | Montedison Spa | Processo per la preparazione del mono-metallil-etere della pirocatechina |
| DE3120556C1 (de) * | 1981-05-23 | 1982-10-28 | Chemische Fabrik Kalk GmbH, 5000 Köln | Verfahren zur Herstellung von Allylaethern bromierter Phenole |
-
1975
- 1975-11-25 DE DE19752552713 patent/DE2552713C3/de not_active Expired
-
1976
- 1976-05-19 FR FR7615129A patent/FR2332970A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2552713A1 (de) | 1977-05-26 |
| FR2332970B3 (enExample) | 1979-02-16 |
| FR2332970A1 (fr) | 1977-06-24 |
| DE2552713B2 (de) | 1978-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |