DE2522693C2 - Verfahren zur Herstellung von Bromarylphosphaten - Google Patents
Verfahren zur Herstellung von BromarylphosphatenInfo
- Publication number
- DE2522693C2 DE2522693C2 DE19752522693 DE2522693A DE2522693C2 DE 2522693 C2 DE2522693 C2 DE 2522693C2 DE 19752522693 DE19752522693 DE 19752522693 DE 2522693 A DE2522693 A DE 2522693A DE 2522693 C2 DE2522693 C2 DE 2522693C2
- Authority
- DE
- Germany
- Prior art keywords
- phosphates
- bromine
- phosphate
- preparation
- triaryl
- 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
- 229910019142 PO4 Inorganic materials 0.000 title claims description 28
- 235000021317 phosphate Nutrition 0.000 title claims description 28
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000031709 bromination Effects 0.000 description 8
- 238000005893 bromination reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- -1 low-brominated aryl phosphates Chemical class 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 5
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000013028 medium composition Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- UWIPPHXVRZCFHT-UHFFFAOYSA-N (2-butylphenyl) dihydrogen phosphate Chemical class CCCCC1=CC=CC=C1OP(O)(O)=O UWIPPHXVRZCFHT-UHFFFAOYSA-N 0.000 description 1
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
- NPKXGASKBARKGM-UHFFFAOYSA-N (2-propylphenyl) dihydrogen phosphate Chemical compound CCCC1=CC=CC=C1OP(O)(O)=O NPKXGASKBARKGM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- NVMHZSCMWYZDCC-UHFFFAOYSA-N bis(4-methylphenyl) phenyl phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=CC=C1 NVMHZSCMWYZDCC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YDICVVYPXSZSFA-UHFFFAOYSA-N diphenyl propan-2-yl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC(C)C)OC1=CC=CC=C1 YDICVVYPXSZSFA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- BMPBPTNLNBRGOT-UHFFFAOYSA-N tris(4-ethylphenyl) phosphate Chemical compound C1=CC(CC)=CC=C1OP(=O)(OC=1C=CC(CC)=CC=1)OC1=CC=C(CC)C=C1 BMPBPTNLNBRGOT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752522693 DE2522693C2 (de) | 1975-05-22 | 1975-05-22 | Verfahren zur Herstellung von Bromarylphosphaten |
| GB2025576A GB1527028A (en) | 1975-05-22 | 1976-05-17 | Process for the production of bromoaryl phosphates |
| CH619976A CH601327A5 (enExample) | 1975-05-22 | 1976-05-18 | |
| NL7605345A NL7605345A (nl) | 1975-05-22 | 1976-05-19 | Werkwijze ter bereiding van broomarylfosfaten. |
| IT4957676A IT1061298B (it) | 1975-05-22 | 1976-05-20 | Procedimento per produrre arilfosfati bromurati e prodotti cosi ottenuti |
| FR7615547A FR2311780A1 (fr) | 1975-05-22 | 1976-05-21 | Procede de preparation de phosphates de bromoaryle |
| BE2055047A BE842048A (fr) | 1975-05-22 | 1976-05-21 | Procede de preparation de phosphates de bromoaryle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752522693 DE2522693C2 (de) | 1975-05-22 | 1975-05-22 | Verfahren zur Herstellung von Bromarylphosphaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2522693A1 DE2522693A1 (de) | 1976-12-09 |
| DE2522693C2 true DE2522693C2 (de) | 1982-10-14 |
Family
ID=5947173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752522693 Expired DE2522693C2 (de) | 1975-05-22 | 1975-05-22 | Verfahren zur Herstellung von Bromarylphosphaten |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE842048A (enExample) |
| CH (1) | CH601327A5 (enExample) |
| DE (1) | DE2522693C2 (enExample) |
| FR (1) | FR2311780A1 (enExample) |
| GB (1) | GB1527028A (enExample) |
| IT (1) | IT1061298B (enExample) |
| NL (1) | NL7605345A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653095A1 (de) * | 1976-11-23 | 1978-05-24 | Bayer Ag | Verfahren zur herstellung von bromarylchlorphosphaten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB874906A (en) * | 1956-09-14 | 1961-08-16 | Dux Chemical Solutions Company | Bromine-containing tricresyl phosphate |
-
1975
- 1975-05-22 DE DE19752522693 patent/DE2522693C2/de not_active Expired
-
1976
- 1976-05-17 GB GB2025576A patent/GB1527028A/en not_active Expired
- 1976-05-18 CH CH619976A patent/CH601327A5/xx not_active IP Right Cessation
- 1976-05-19 NL NL7605345A patent/NL7605345A/xx not_active Application Discontinuation
- 1976-05-20 IT IT4957676A patent/IT1061298B/it active
- 1976-05-21 BE BE2055047A patent/BE842048A/xx unknown
- 1976-05-21 FR FR7615547A patent/FR2311780A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE842048A (fr) | 1976-11-22 |
| DE2522693A1 (de) | 1976-12-09 |
| NL7605345A (nl) | 1976-11-24 |
| FR2311780A1 (fr) | 1976-12-17 |
| IT1061298B (it) | 1983-02-28 |
| FR2311780B1 (enExample) | 1979-09-07 |
| GB1527028A (en) | 1978-10-04 |
| CH601327A5 (enExample) | 1978-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |