DE2100779A1 - Verfahren zur Herstellung von Dialkylphosphinsäureestern - Google Patents
Verfahren zur Herstellung von DialkylphosphinsäureesternInfo
- Publication number
- DE2100779A1 DE2100779A1 DE19712100779 DE2100779A DE2100779A1 DE 2100779 A1 DE2100779 A1 DE 2100779A1 DE 19712100779 DE19712100779 DE 19712100779 DE 2100779 A DE2100779 A DE 2100779A DE 2100779 A1 DE2100779 A1 DE 2100779A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- preparation
- acid esters
- dialkylphosphinic acid
- yield
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- -1 phosphorus compound Chemical class 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- PMVVRSKJCGEFIY-UHFFFAOYSA-N methylphosphonous acid Chemical compound CP(O)O PMVVRSKJCGEFIY-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UWBDLYIXZYOPJX-UHFFFAOYSA-N 1-[butoxy(methyl)phosphoryl]dodecane Chemical compound C(CCC)OP(=O)(CCCCCCCCCCCC)C UWBDLYIXZYOPJX-UHFFFAOYSA-N 0.000 description 1
- HFZNAKHLQWAGSB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]dodecane Chemical compound C(C)OP(=O)(CCCCCCCCCCCC)C HFZNAKHLQWAGSB-UHFFFAOYSA-N 0.000 description 1
- FYBPQGGQSQAMMZ-UHFFFAOYSA-N 1-[methyl(2-methylpropoxy)phosphoryl]dodecane Chemical compound C(C(C)C)OP(=O)(CCCCCCCCCCCC)C FYBPQGGQSQAMMZ-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- NFJDFXLCWHYUOU-UHFFFAOYSA-N 2-ethylhexoxy(methyl)phosphinous acid Chemical compound CCCCC(CC)COP(C)O NFJDFXLCWHYUOU-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- UZCGXBVROJZPSY-UHFFFAOYSA-N CCCCCCCCCCCCCCCC.P(O)(O)=O Chemical compound CCCCCCCCCCCCCCCC.P(O)(O)=O UZCGXBVROJZPSY-UHFFFAOYSA-N 0.000 description 1
- AFMVDAAQNQSISB-UHFFFAOYSA-N CCP(=O)(CC)OCC(C)C Chemical compound CCP(=O)(CC)OCC(C)C AFMVDAAQNQSISB-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- GZUFHXSFPZCNJA-UHFFFAOYSA-N butoxy(methyl)phosphinic acid Chemical compound CCCCOP(C)(O)=O GZUFHXSFPZCNJA-UHFFFAOYSA-N 0.000 description 1
- PKVYRMYNUBUIJI-UHFFFAOYSA-N butoxy(methyl)phosphinous acid Chemical compound CCCCOP(C)O PKVYRMYNUBUIJI-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 1
- GZBQGSURWYXEQF-UHFFFAOYSA-N ethoxy(methyl)phosphinous acid Chemical compound CCOP(C)O GZBQGSURWYXEQF-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- PRZXMHGSSBGFKS-UHFFFAOYSA-N hexadecyl(methyl)phosphinic acid Chemical compound CCCCCCCCCCCCCCCCP(C)(O)=O PRZXMHGSSBGFKS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- MFBYDXODTSGNNM-UHFFFAOYSA-N methoxy(methyl)phosphinous acid Chemical compound COP(C)O MFBYDXODTSGNNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZNGLGLXWTVMUCL-UHFFFAOYSA-N methyl(2-methylpropoxy)phosphinic acid Chemical compound CC(C)COP(C)(O)=O ZNGLGLXWTVMUCL-UHFFFAOYSA-N 0.000 description 1
- GPGCPVFGIJFFAO-UHFFFAOYSA-N methyl(octoxy)phosphinic acid Chemical compound CCCCCCCCOP(C)(O)=O GPGCPVFGIJFFAO-UHFFFAOYSA-N 0.000 description 1
- YIZNYMADIRZRAL-UHFFFAOYSA-N methyl(propan-2-yloxy)phosphinous acid Chemical compound CC(C)OP(C)O YIZNYMADIRZRAL-UHFFFAOYSA-N 0.000 description 1
- WPEAFCGWTBGVNU-UHFFFAOYSA-N methyl(propoxy)phosphinic acid Chemical compound CCCOP(C)(O)=O WPEAFCGWTBGVNU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712100779 DE2100779A1 (de) | 1971-01-08 | 1971-01-08 | Verfahren zur Herstellung von Dialkylphosphinsäureestern |
| NL7200014A NL7200014A (xx) | 1971-01-08 | 1972-01-03 | |
| IT1907972A IT1006010B (it) | 1971-01-08 | 1972-01-05 | Processo per la preparazione di esteri di acidi dialchilfosfinici |
| CH19972A CH572064A5 (xx) | 1971-01-08 | 1972-01-06 | |
| CA131,888A CA963912A (en) | 1971-01-08 | 1972-01-07 | Process for the manufacture of dialkyl-phosphinic acid esters |
| GB104772A GB1375049A (xx) | 1971-01-08 | 1972-01-10 | |
| FR7200612A FR2121694B2 (xx) | 1971-01-08 | 1972-01-10 | |
| BE777878A BE777878A (fr) | 1971-01-08 | 1972-01-10 | Procede de preparation d'esters d'acides di-alkyl- phosphimiques |
| US427253A US3914345A (en) | 1971-01-08 | 1973-12-21 | Process for the manufacture of dialkyl-phosphinic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712100779 DE2100779A1 (de) | 1971-01-08 | 1971-01-08 | Verfahren zur Herstellung von Dialkylphosphinsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2100779A1 true DE2100779A1 (de) | 1972-07-20 |
Family
ID=5795438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712100779 Withdrawn DE2100779A1 (de) | 1971-01-08 | 1971-01-08 | Verfahren zur Herstellung von Dialkylphosphinsäureestern |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE777878A (xx) |
| CA (1) | CA963912A (xx) |
| CH (1) | CH572064A5 (xx) |
| DE (1) | DE2100779A1 (xx) |
| FR (1) | FR2121694B2 (xx) |
| GB (1) | GB1375049A (xx) |
| IT (1) | IT1006010B (xx) |
| NL (1) | NL7200014A (xx) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2540283A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Carboxylgruppenhaltige organische phosphorverbindungen |
| DE19752735A1 (de) * | 1997-11-28 | 1999-07-01 | Clariant Gmbh | Verfahren zur Herstellung von Salzen der Dialkylphosphinsäure |
| DE19851768C2 (de) * | 1997-11-28 | 2000-03-23 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäuresalzen |
| EP1958950A1 (de) | 2003-12-19 | 2008-08-20 | Clariant Produkte (Deutschland) GmbH | Verwendung von Dialkylphosphinsäuresalzen |
| US7420007B2 (en) | 2003-12-19 | 2008-09-02 | Clariant Produkte (Deutschland) Gmbh | Dialkylphosphinic salts |
| WO2009010188A3 (de) * | 2007-07-13 | 2009-11-26 | Clariant Finance (Bvi) Limited | Phosphonigsäuren, -salze und - ester, verfahren zu deren herstellung und ihre verwendung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL145897B (nl) * | 1948-04-12 | Union Carbide Corp | Werkwijze voor het bereiden van korrelvormige wasmiddelen. |
-
1971
- 1971-01-08 DE DE19712100779 patent/DE2100779A1/de not_active Withdrawn
-
1972
- 1972-01-03 NL NL7200014A patent/NL7200014A/xx not_active Application Discontinuation
- 1972-01-05 IT IT1907972A patent/IT1006010B/it active
- 1972-01-06 CH CH19972A patent/CH572064A5/xx not_active IP Right Cessation
- 1972-01-07 CA CA131,888A patent/CA963912A/en not_active Expired
- 1972-01-10 FR FR7200612A patent/FR2121694B2/fr not_active Expired
- 1972-01-10 BE BE777878A patent/BE777878A/xx unknown
- 1972-01-10 GB GB104772A patent/GB1375049A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2540283A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Carboxylgruppenhaltige organische phosphorverbindungen |
| DE19752735A1 (de) * | 1997-11-28 | 1999-07-01 | Clariant Gmbh | Verfahren zur Herstellung von Salzen der Dialkylphosphinsäure |
| DE19752735C2 (de) * | 1997-11-28 | 2000-01-20 | Clariant Gmbh | Verfahren zur Herstellung von Salzen der Dialkylphosphinsäure |
| DE19851768C2 (de) * | 1997-11-28 | 2000-03-23 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäuresalzen |
| EP1958950A1 (de) | 2003-12-19 | 2008-08-20 | Clariant Produkte (Deutschland) GmbH | Verwendung von Dialkylphosphinsäuresalzen |
| US7420007B2 (en) | 2003-12-19 | 2008-09-02 | Clariant Produkte (Deutschland) Gmbh | Dialkylphosphinic salts |
| US7635785B2 (en) | 2003-12-19 | 2009-12-22 | Clariant Deutschland GmbH | Process for preparation of dialkylphosphinic salts |
| WO2009010188A3 (de) * | 2007-07-13 | 2009-11-26 | Clariant Finance (Bvi) Limited | Phosphonigsäuren, -salze und - ester, verfahren zu deren herstellung und ihre verwendung |
| US8293938B2 (en) | 2007-07-13 | 2012-10-23 | Clariant Finance (Bvi) Limited | Alkylphosphonous acids, salts and esters, methods for the production thereof, and use of the same |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7200014A (xx) | 1972-07-11 |
| FR2121694A2 (xx) | 1972-08-25 |
| FR2121694B2 (xx) | 1978-08-04 |
| GB1375049A (xx) | 1974-11-27 |
| IT1006010B (it) | 1976-09-30 |
| BE777878A (fr) | 1972-07-10 |
| CA963912A (en) | 1975-03-04 |
| CH572064A5 (xx) | 1976-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| 8130 | Withdrawal |