HU222807B1 - Eljárás DOP előállítására és az eljárással előállított, csökkentett OPP-tartalmú DOP - Google Patents
Eljárás DOP előállítására és az eljárással előállított, csökkentett OPP-tartalmú DOP Download PDFInfo
- Publication number
- HU222807B1 HU222807B1 HU0002801A HUP0002801A HU222807B1 HU 222807 B1 HU222807 B1 HU 222807B1 HU 0002801 A HU0002801 A HU 0002801A HU P0002801 A HUP0002801 A HU P0002801A HU 222807 B1 HU222807 B1 HU 222807B1
- Authority
- HU
- Hungary
- Prior art keywords
- process according
- opp
- mixture
- dop
- oxa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims abstract description 66
- 235000010292 orthophenyl phenol Nutrition 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 16
- 239000007858 starting material Substances 0.000 claims abstract description 12
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000001256 steam distillation Methods 0.000 claims abstract description 10
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 7
- -1 P 4 O 6 Chemical compound 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000000746 purification Methods 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19933932A DE19933932B4 (de) | 1999-07-20 | 1999-07-20 | Verfahren zur Herstellung von DOP und danach hergestelltes DOP mit reduziertem OPP-Gehalt |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HU0002801D0 HU0002801D0 (en) | 2000-09-28 |
| HUP0002801A2 HUP0002801A2 (hu) | 2001-12-28 |
| HUP0002801A3 HUP0002801A3 (en) | 2002-04-29 |
| HU222807B1 true HU222807B1 (hu) | 2003-10-28 |
Family
ID=7915379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0002801A HU222807B1 (hu) | 1999-07-20 | 2000-07-20 | Eljárás DOP előállítására és az eljárással előállított, csökkentett OPP-tartalmú DOP |
Country Status (4)
| Country | Link |
|---|---|
| CZ (1) | CZ298599B6 (cs) |
| DE (1) | DE19933932B4 (cs) |
| HU (1) | HU222807B1 (cs) |
| PL (1) | PL201069B1 (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004113355A1 (de) * | 2003-06-18 | 2004-12-29 | Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. | Verfahren zur herstellung mehrfach dopo-haltiger organischer verbindungen und ihre verwendung |
| CN105949242B (zh) * | 2016-05-18 | 2018-10-30 | 衡阳师范学院 | 一种9,10-二氢-9-氧-10-磷杂菲-10-氧化物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127590A (en) * | 1975-10-14 | 1978-11-28 | Toyo Boseki Kabushiki Kaisha | Phosphorus-containing compounds |
| DE19505352A1 (de) * | 1994-09-19 | 1996-03-21 | Bayer Ag | Verfahren zur Herstellung von 6-Oxo-(6H)-dibenz-[c,e] [1,2]-oxaphosphorinen (ODOP) |
-
1999
- 1999-07-20 DE DE19933932A patent/DE19933932B4/de not_active Expired - Fee Related
-
2000
- 2000-07-19 PL PL341550A patent/PL201069B1/pl unknown
- 2000-07-20 CZ CZ20002674A patent/CZ298599B6/cs not_active IP Right Cessation
- 2000-07-20 HU HU0002801A patent/HU222807B1/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20002674A3 (cs) | 2001-04-11 |
| DE19933932A1 (de) | 2001-01-25 |
| PL201069B1 (pl) | 2009-03-31 |
| CZ298599B6 (cs) | 2007-11-21 |
| HUP0002801A2 (hu) | 2001-12-28 |
| HU0002801D0 (en) | 2000-09-28 |
| DE19933932B4 (de) | 2006-06-14 |
| PL341550A1 (en) | 2001-01-29 |
| HUP0002801A3 (en) | 2002-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HFG4 | Patent granted, date of granting |
Effective date: 20030916 |
|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |