DE19828861C1 - Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung - Google Patents
Verfahren zur Herstellung von Phosphonigsäureestern und deren VerwendungInfo
- Publication number
- DE19828861C1 DE19828861C1 DE19828861A DE19828861A DE19828861C1 DE 19828861 C1 DE19828861 C1 DE 19828861C1 DE 19828861 A DE19828861 A DE 19828861A DE 19828861 A DE19828861 A DE 19828861A DE 19828861 C1 DE19828861 C1 DE 19828861C1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- halides
- reaction
- yellow phosphorus
- reactive flame
- 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 - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title claims description 11
- 239000003063 flame retardant Substances 0.000 title claims description 8
- 238000003786 synthesis reaction Methods 0.000 title claims description 5
- 230000015572 biosynthetic process Effects 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 title claims description 3
- 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 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 15
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims abstract description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 alkaline earth metal salts Chemical class 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- PMVVRSKJCGEFIY-UHFFFAOYSA-N methylphosphonous acid Chemical compound CP(O)O PMVVRSKJCGEFIY-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims 1
- 229920001225 polyester resin Polymers 0.000 claims 1
- 239000004645 polyester resin Substances 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 150000002924 oxiranes Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
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)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19828861A DE19828861C1 (de) | 1998-06-29 | 1998-06-29 | Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung |
| EP99110829A EP0969009B1 (de) | 1998-06-29 | 1999-06-05 | Verfahren zur Herstellung von Phosphonigsäureestern |
| ES99110829T ES2207067T3 (es) | 1998-06-29 | 1999-06-05 | Procedimiento para la preparacion de esteres de acidos fosfonosos. |
| DE59906740T DE59906740D1 (de) | 1998-06-29 | 1999-06-05 | Verfahren zur Herstellung von Phosphonigsäureestern |
| AT99110829T ATE248180T1 (de) | 1998-06-29 | 1999-06-05 | Verfahren zur herstellung von phosphonigsäureestern |
| JP11182425A JP2000038399A (ja) | 1998-06-29 | 1999-06-28 | 亜ホスホン酸エステルの製造方法 |
| US09/342,771 US6090967A (en) | 1998-06-29 | 1999-06-29 | Process for preparing phosphonous esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19828861A DE19828861C1 (de) | 1998-06-29 | 1998-06-29 | Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19828861C1 true DE19828861C1 (de) | 1999-12-02 |
Family
ID=7872317
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19828861A Expired - Fee Related DE19828861C1 (de) | 1998-06-29 | 1998-06-29 | Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung |
| DE59906740T Expired - Fee Related DE59906740D1 (de) | 1998-06-29 | 1999-06-05 | Verfahren zur Herstellung von Phosphonigsäureestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59906740T Expired - Fee Related DE59906740D1 (de) | 1998-06-29 | 1999-06-05 | Verfahren zur Herstellung von Phosphonigsäureestern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6090967A (enExample) |
| EP (1) | EP0969009B1 (enExample) |
| JP (1) | JP2000038399A (enExample) |
| AT (1) | ATE248180T1 (enExample) |
| DE (2) | DE19828861C1 (enExample) |
| ES (1) | ES2207067T3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19923617A1 (de) * | 1999-05-25 | 2000-11-30 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern |
| DE102007032669A1 (de) * | 2007-07-13 | 2009-01-15 | Clariant International Limited | Alkylphosphonigsäuren, -salze und -ester, Verfahren zu deren Herstellung und ihre Verwendung |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19923830C1 (de) * | 1999-05-25 | 2001-02-01 | Clariant Gmbh | Verfahren zur Herstellung von Metallsalzen von Alkylphosphonigen Säuren I |
| DE19923615C1 (de) * | 1999-05-25 | 2000-12-14 | Clariant Gmbh | Verfahren zur Herstellung von Alkylphosphonigsäureestern |
| DE19923619C2 (de) * | 1999-05-25 | 2001-08-23 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäuren und deren Salzen |
| DE19923743C2 (de) * | 1999-05-25 | 2002-03-07 | Clariant Gmbh | Verfahren zur Herstellung von (Metall)salzen von Alkylphosphonigen Säuren II |
| DE10153780C1 (de) | 2001-11-02 | 2002-11-28 | Clariant Gmbh | Verfahren zur Herstellung von Carboxyethylmethylphosphinsäureglykolester und ihre Verwendung |
| DE102006010361A1 (de) * | 2006-03-07 | 2007-09-13 | Clariant International Limited | Mischungen aus Mono-Carboxylfunktionalisierten Dialkylphosphinsäureestern und weiteren Komponenten |
| DE102008063627A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
| CN115069246B (zh) * | 2021-03-15 | 2023-08-15 | 中国石油化工股份有限公司 | 一种负载型银催化剂及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2120779A1 (de) * | 1971-04-28 | 1973-07-19 | Diehl Fa | Tastatur |
| DE2540283A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Carboxylgruppenhaltige organische phosphorverbindungen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3579576A (en) * | 1964-02-25 | 1971-05-18 | Sun Oil Co | Organophosphorus compounds and a process for the making thereof |
| US3316293A (en) * | 1965-07-26 | 1967-04-25 | Hooker Chemical Corp | Organic phosphorus compounds |
| DE19604195C1 (de) * | 1996-02-06 | 1997-04-17 | Hoechst Ag | Verfahren zur Herstellung von Phosphonigsäuremonoalkylestern |
| EP1036079B1 (de) * | 1997-11-28 | 2002-07-31 | Clariant GmbH | Verfahren zur alkylierung von elementarem phosphor |
-
1998
- 1998-06-29 DE DE19828861A patent/DE19828861C1/de not_active Expired - Fee Related
-
1999
- 1999-06-05 EP EP99110829A patent/EP0969009B1/de not_active Expired - Lifetime
- 1999-06-05 ES ES99110829T patent/ES2207067T3/es not_active Expired - Lifetime
- 1999-06-05 AT AT99110829T patent/ATE248180T1/de not_active IP Right Cessation
- 1999-06-05 DE DE59906740T patent/DE59906740D1/de not_active Expired - Fee Related
- 1999-06-28 JP JP11182425A patent/JP2000038399A/ja active Pending
- 1999-06-29 US US09/342,771 patent/US6090967A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2120779A1 (de) * | 1971-04-28 | 1973-07-19 | Diehl Fa | Tastatur |
| DE2540283A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Carboxylgruppenhaltige organische phosphorverbindungen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19923617A1 (de) * | 1999-05-25 | 2000-11-30 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern |
| DE19923617C2 (de) * | 1999-05-25 | 2001-10-31 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern |
| DE102007032669A1 (de) * | 2007-07-13 | 2009-01-15 | Clariant International Limited | Alkylphosphonigsäuren, -salze und -ester, Verfahren zu deren Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2207067T3 (es) | 2004-05-16 |
| EP0969009A2 (de) | 2000-01-05 |
| EP0969009B1 (de) | 2003-08-27 |
| EP0969009A3 (de) | 2000-10-18 |
| DE59906740D1 (de) | 2003-10-02 |
| JP2000038399A (ja) | 2000-02-08 |
| ATE248180T1 (de) | 2003-09-15 |
| US6090967A (en) | 2000-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, 65929 FRANKF |
|
| 8339 | Ceased/non-payment of the annual fee |