DE2511932C2 - Verfahren zur Herstellung von tert.-Hydroxyalkylphosphinoxiden - Google Patents
Verfahren zur Herstellung von tert.-HydroxyalkylphosphinoxidenInfo
- Publication number
- DE2511932C2 DE2511932C2 DE2511932A DE2511932A DE2511932C2 DE 2511932 C2 DE2511932 C2 DE 2511932C2 DE 2511932 A DE2511932 A DE 2511932A DE 2511932 A DE2511932 A DE 2511932A DE 2511932 C2 DE2511932 C2 DE 2511932C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- hydroxymethyl
- water
- tertiary
- oxide
- 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 30
- 238000002360 preparation method Methods 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- -1 hydroxyl ions Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 6
- 150000003003 phosphines Chemical class 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- XWSQLOKESIKBIA-UHFFFAOYSA-N [hydroxymethyl(methyl)phosphoryl]methanol Chemical compound OCP(=O)(C)CO XWSQLOKESIKBIA-UHFFFAOYSA-N 0.000 description 5
- MRVZORUPSXTRHD-UHFFFAOYSA-N bis(hydroxymethyl)phosphorylmethanol Chemical compound OCP(=O)(CO)CO MRVZORUPSXTRHD-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 description 1
- AZHWLYZFKMFDSO-UHFFFAOYSA-M C[P+](CO)(CO)CO.[OH-] Chemical compound C[P+](CO)(CO)CO.[OH-] AZHWLYZFKMFDSO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RQOKIVVUNQCMJS-UHFFFAOYSA-N dimethylphosphorylmethanol Chemical compound CP(C)(=O)CO RQOKIVVUNQCMJS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HXZSFRJGDPGVNY-UHFFFAOYSA-N methyl(oxido)phosphanium Chemical compound C[PH2]=O HXZSFRJGDPGVNY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- IOIHFHNPXJFODN-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;hydroxide Chemical compound [OH-].OC[P+](CO)(CO)CO IOIHFHNPXJFODN-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2511932A DE2511932C2 (de) | 1975-03-19 | 1975-03-19 | Verfahren zur Herstellung von tert.-Hydroxyalkylphosphinoxiden |
| SU7602317695A SU581871A3 (ru) | 1975-03-19 | 1976-02-02 | Способ получени третичных оксиалкилфосфиноксидов |
| CA245,971A CA1073470A (en) | 1975-03-19 | 1976-02-17 | Production of hydroxyalkylphosphine oxides |
| GB6165/76A GB1503074A (en) | 1975-03-19 | 1976-02-17 | Production of hydroxyalkylphosphine oxides |
| DD191333A DD123097A5 (OSRAM) | 1975-03-19 | 1976-02-19 | |
| US05/666,699 US4076755A (en) | 1975-03-19 | 1976-03-15 | Production of hydroxyalkylphosphine oxides |
| IT48583/76A IT1058003B (it) | 1975-03-19 | 1976-03-16 | Procedimento per produrre ossidi idrossi alchil fosfinici |
| BE165243A BE839655A (fr) | 1975-03-19 | 1976-03-17 | Procede de preparation d'oxydes d'hydroxyalkylphosphines |
| NL7602786A NL7602786A (nl) | 1975-03-19 | 1976-03-17 | Werkwijze voor de bereiding van hydroxyalkyl- fosfinoxyden. |
| CH349676A CH606062A5 (OSRAM) | 1975-03-19 | 1976-03-19 | |
| JP51030714A JPS51115424A (en) | 1975-03-19 | 1976-03-19 | Process for manufacturing hydroxyalkyll phosphineoxide |
| FR7608077A FR2304618A1 (fr) | 1975-03-19 | 1976-03-19 | Procede de preparation d'oxydes d'hydroxyalkylphosphines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2511932A DE2511932C2 (de) | 1975-03-19 | 1975-03-19 | Verfahren zur Herstellung von tert.-Hydroxyalkylphosphinoxiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2511932A1 DE2511932A1 (de) | 1976-09-30 |
| DE2511932C2 true DE2511932C2 (de) | 1984-01-26 |
Family
ID=5941747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2511932A Expired DE2511932C2 (de) | 1975-03-19 | 1975-03-19 | Verfahren zur Herstellung von tert.-Hydroxyalkylphosphinoxiden |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4076755A (OSRAM) |
| JP (1) | JPS51115424A (OSRAM) |
| BE (1) | BE839655A (OSRAM) |
| CA (1) | CA1073470A (OSRAM) |
| CH (1) | CH606062A5 (OSRAM) |
| DD (1) | DD123097A5 (OSRAM) |
| DE (1) | DE2511932C2 (OSRAM) |
| FR (1) | FR2304618A1 (OSRAM) |
| GB (1) | GB1503074A (OSRAM) |
| IT (1) | IT1058003B (OSRAM) |
| NL (1) | NL7602786A (OSRAM) |
| SU (1) | SU581871A3 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346236A (en) * | 1981-02-09 | 1982-08-24 | Fmc Corporation | Method of oxidizing tertiary-alkyl phosphines |
| CA2752474C (en) * | 2009-02-12 | 2017-06-20 | Rhodia Operations | Methods for controlling depolymerization of polymer compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL107986C (OSRAM) * | 1957-01-23 | |||
| NL262953A (OSRAM) * | 1960-04-06 | 1900-01-01 | ||
| DE1930521C3 (de) * | 1969-06-16 | 1980-05-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Trishydroxymethylphosphinoxid |
| US3660495A (en) * | 1969-12-10 | 1972-05-02 | Hooker Chemical Corp | Process for preparing hydroxymethylated phosphines |
| US3852362A (en) * | 1969-12-24 | 1974-12-03 | Polaroid Corp | Preparation of tertiary organophosphine oxides |
| US3636160A (en) * | 1970-07-13 | 1972-01-18 | Hooker Chemical Corp | Trishydroxymethyl phosphine oxide from phosphine and formaldehyde |
-
1975
- 1975-03-19 DE DE2511932A patent/DE2511932C2/de not_active Expired
-
1976
- 1976-02-02 SU SU7602317695A patent/SU581871A3/ru active
- 1976-02-17 CA CA245,971A patent/CA1073470A/en not_active Expired
- 1976-02-17 GB GB6165/76A patent/GB1503074A/en not_active Expired
- 1976-02-19 DD DD191333A patent/DD123097A5/xx unknown
- 1976-03-15 US US05/666,699 patent/US4076755A/en not_active Expired - Lifetime
- 1976-03-16 IT IT48583/76A patent/IT1058003B/it active
- 1976-03-17 NL NL7602786A patent/NL7602786A/xx not_active Application Discontinuation
- 1976-03-17 BE BE165243A patent/BE839655A/xx not_active IP Right Cessation
- 1976-03-19 CH CH349676A patent/CH606062A5/xx not_active IP Right Cessation
- 1976-03-19 FR FR7608077A patent/FR2304618A1/fr active Granted
- 1976-03-19 JP JP51030714A patent/JPS51115424A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1058003B (it) | 1982-04-10 |
| FR2304618A1 (fr) | 1976-10-15 |
| DE2511932A1 (de) | 1976-09-30 |
| NL7602786A (nl) | 1976-09-21 |
| SU581871A3 (ru) | 1977-11-25 |
| BE839655A (fr) | 1976-09-17 |
| US4076755A (en) | 1978-02-28 |
| JPS51115424A (en) | 1976-10-12 |
| CH606062A5 (OSRAM) | 1978-10-13 |
| DD123097A5 (OSRAM) | 1976-11-20 |
| CA1073470A (en) | 1980-03-11 |
| FR2304618B1 (OSRAM) | 1982-11-12 |
| GB1503074A (en) | 1978-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |