WO2001032666A1 - Procede de production de phosphites organiques - Google Patents
Procede de production de phosphites organiques Download PDFInfo
- Publication number
- WO2001032666A1 WO2001032666A1 PCT/EP2000/010520 EP0010520W WO0132666A1 WO 2001032666 A1 WO2001032666 A1 WO 2001032666A1 EP 0010520 W EP0010520 W EP 0010520W WO 0132666 A1 WO0132666 A1 WO 0132666A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- radicals
- alkyl radicals
- carry
- aromatic
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 150000008301 phosphite esters Chemical class 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 15
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 phosphorus compound Chemical class 0.000 description 111
- 125000000524 functional group Chemical group 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 14
- 229910052736 halogen Inorganic materials 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- HGLNEADZDZEOQO-UHFFFAOYSA-N 1,3,2-dioxaphosphole Chemical class O1POC=C1 HGLNEADZDZEOQO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IENJVSLDIJZRFU-UHFFFAOYSA-N chloro diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCl)OC1=CC=CC=C1 IENJVSLDIJZRFU-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JHNJGLVSPIMBLD-UHFFFAOYSA-N dichloro(ethyl)phosphane Chemical compound CCP(Cl)Cl JHNJGLVSPIMBLD-UHFFFAOYSA-N 0.000 description 1
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 1
- NJFYHZGHWCKUBI-UHFFFAOYSA-N dichloro(naphthalen-1-yl)phosphane Chemical compound C1=CC=C2C(P(Cl)Cl)=CC=CC2=C1 NJFYHZGHWCKUBI-UHFFFAOYSA-N 0.000 description 1
- LNWLQZZUUAHFRN-UHFFFAOYSA-N dichloro(naphthalen-2-yl)phosphane Chemical compound C1=CC=CC2=CC(P(Cl)Cl)=CC=C21 LNWLQZZUUAHFRN-UHFFFAOYSA-N 0.000 description 1
- REJUONUIORHCPY-UHFFFAOYSA-N dichloro-(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(Cl)Cl REJUONUIORHCPY-UHFFFAOYSA-N 0.000 description 1
- CQLLYGPVLZFSNM-UHFFFAOYSA-N dichloro-(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(Cl)Cl)=C1 CQLLYGPVLZFSNM-UHFFFAOYSA-N 0.000 description 1
- SQKDMSFZWCIFEZ-UHFFFAOYSA-N dichloro-(4-methylphenyl)phosphane Chemical compound CC1=CC=C(P(Cl)Cl)C=C1 SQKDMSFZWCIFEZ-UHFFFAOYSA-N 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical compound ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
-
- 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
- C07F9/141—Esters of phosphorous acids
-
- 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
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
Definitions
- Radicals X to compound IV is 1:10 to 10: 1, giving a mixture V comprising compound I and compound II,
- a compound III of the formula PX ( 3 _ a ) R 2 a is used in step a.
- alkyl radicals can carry further functional groups, such as alkoxy, aryloxy, disubstituted amino, mercapto groups or halogens, such as chlorine, bromine or iodine, preferably the alkyl radicals do not carry any functional groups.
- alkyl radicals linear or cyclic C ⁇ to Cia radicals can be used, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, n-pentyl radicals and their isomers , N-hexyl radicals and their isomers, cyclopentyl or cyclohexyl radicals, where the cyclic alkyl radicals can carry linear or further cyclic alkyl radicals or aromatic radicals and the alkyl radicals can carry cyclic alkyl radicals or aromatic radicals as substituents.
- Suitable aromatic substituents are heterocycles, preferably homocycles, such as naphthyl, preferably phenyl radicals. These aromatic substituents can carry further functional groups, such as alkoxy, aryloxy, disubstituted amino, mercapto groups or halogens, such as chlorine, bromine or iodine, preferably the aromatic radicals do not carry any functional groups.
- carbon atoms can be substituted by other atoms, such as oxygen, nitrogen, sulfur, preferably the alkyl radicals are not substituted.
- the residues of the mixture V remaining after the separation of the compounds I and II can advantageously be recycled in step a of the process according to the invention.
- the separation is carried out by distillation, a reduction in the pressure, preferably in the range from 10 to 10 5 Pa, in particular 5000 to 10 Pa, has proven advantageous.
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)
Abstract
L'invention concerne un procédé de production de composés de la formule X(1-a) R2a P (OR1)2 (I) ou X(2-a) R2a P (OR1) (II) où: X = Cl, Br, J; R1 représente un reste organique; R2 représente un reste organique; a vaut 0,1. L'invention est caractérisée en ce que a) l'on fait réagir un composé (III) de la formule PX¿(3-a)R?2a avec un composé (IV) de la formule R1OH à des températures comprises entre 10 et 200 °C pour obtenir un mélange (V) contenant le composé (I) et le composé (II), le rapport molaire Restes X utilisés/Composé (IV) étant de 1:10 à 10:1 ; b) on sépare les composés (I) et (II) du mélange (V) et c) on renvoie le composé (I) ou le composé (II) à l'étape (a).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU11449/01A AU1144901A (en) | 1999-11-03 | 2000-10-25 | Method for producing organophosphites |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19953048.3 | 1999-11-03 | ||
| DE1999153048 DE19953048A1 (de) | 1999-11-03 | 1999-11-03 | Verfahren zur Herstellung von Organophosphiten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001032666A1 true WO2001032666A1 (fr) | 2001-05-10 |
Family
ID=7927879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2000/010520 WO2001032666A1 (fr) | 1999-11-03 | 2000-10-25 | Procede de production de phosphites organiques |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU1144901A (fr) |
| DE (1) | DE19953048A1 (fr) |
| WO (1) | WO2001032666A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6852824B2 (en) | 2000-08-11 | 2005-02-08 | Basf Coatings Ag | Polyurethanes and graft copolymers based on polyurethane, and their use for producing coating materials, adhesives, and sealing compounds |
| WO2008006735A1 (fr) | 2006-07-12 | 2008-01-17 | Basf Se | Procédé de production de composés phosphore organiques halogénés |
| EP2239248A2 (fr) | 2002-12-02 | 2010-10-13 | INVISTA Technologies S.à.r.l. | Synthese selective d'organophosphite |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2408744A (en) * | 1945-04-11 | 1946-10-08 | Allied Chem & Dye Corp | Process of producing esters |
| US2866807A (en) * | 1954-04-15 | 1958-12-30 | Virginia Carolina Chem Corp | Aliphatic aryl phosphites |
| EP0032202A1 (fr) * | 1979-12-17 | 1981-07-22 | Bayer Ag | Procédé pour la préparation d'esters aryliques neutres de l'acide phosphoreux |
-
1999
- 1999-11-03 DE DE1999153048 patent/DE19953048A1/de not_active Withdrawn
-
2000
- 2000-10-25 WO PCT/EP2000/010520 patent/WO2001032666A1/fr active Application Filing
- 2000-10-25 AU AU11449/01A patent/AU1144901A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2408744A (en) * | 1945-04-11 | 1946-10-08 | Allied Chem & Dye Corp | Process of producing esters |
| US2866807A (en) * | 1954-04-15 | 1958-12-30 | Virginia Carolina Chem Corp | Aliphatic aryl phosphites |
| EP0032202A1 (fr) * | 1979-12-17 | 1981-07-22 | Bayer Ag | Procédé pour la préparation d'esters aryliques neutres de l'acide phosphoreux |
Non-Patent Citations (1)
| Title |
|---|
| KÖNIG T. ET AL.: "Synthesen und NMR- Spektren phosphororganischer Antioxi- dantien und verwandter Verbindungen", JOURNAL FÜR PRAKTISCHE CHEMIE, vol. 334, 1992, LEIPZIG, DE, pages 333 - 339, XP000982998, ISSN: 0021-8383 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6852824B2 (en) | 2000-08-11 | 2005-02-08 | Basf Coatings Ag | Polyurethanes and graft copolymers based on polyurethane, and their use for producing coating materials, adhesives, and sealing compounds |
| EP2239248A2 (fr) | 2002-12-02 | 2010-10-13 | INVISTA Technologies S.à.r.l. | Synthese selective d'organophosphite |
| EP2243763A2 (fr) | 2002-12-02 | 2010-10-27 | Invista Technologies S.à.r.l. | Synthese selective d'organophosphite |
| WO2008006735A1 (fr) | 2006-07-12 | 2008-01-17 | Basf Se | Procédé de production de composés phosphore organiques halogénés |
| US7851656B2 (en) | 2006-07-12 | 2010-12-14 | Basf Se | Method for producing organic phosphorous compounds containing halogens |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19953048A1 (de) | 2001-05-10 |
| AU1144901A (en) | 2001-05-14 |
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