SE424639B - Sett att framstella fosforhaltiga estrar - Google Patents
Sett att framstella fosforhaltiga estrarInfo
- Publication number
- SE424639B SE424639B SE7602715A SE7602715A SE424639B SE 424639 B SE424639 B SE 424639B SE 7602715 A SE7602715 A SE 7602715A SE 7602715 A SE7602715 A SE 7602715A SE 424639 B SE424639 B SE 424639B
- Authority
- SE
- Sweden
- Prior art keywords
- phosphorus
- carbon atoms
- reaction mixture
- alcohol
- alkyl group
- Prior art date
Links
- 150000003017 phosphorus Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 claims description 28
- 239000011574 phosphorus Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- -1 phosphorus halogen compounds Chemical class 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000003574 free electron Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 5
- ZNGLGLXWTVMUCL-UHFFFAOYSA-N methyl(2-methylpropoxy)phosphinic acid Chemical compound CC(C)COP(C)(O)=O ZNGLGLXWTVMUCL-UHFFFAOYSA-N 0.000 description 5
- IGNFYWATZHBYFJ-UHFFFAOYSA-N 2-methyl-1-[methyl(2-methylpropoxy)phosphoryl]oxypropane Chemical compound CC(C)COP(C)(=O)OCC(C)C IGNFYWATZHBYFJ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XAZJFCQCYNQNBH-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methylpropane Chemical compound CC(C)COP(C)(C)=O XAZJFCQCYNQNBH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QPKOILOWXGLVJS-UHFFFAOYSA-N bis(2-methylpropoxy)-oxophosphanium Chemical compound CC(C)CO[P+](=O)OCC(C)C QPKOILOWXGLVJS-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- KJKWGCTWYJCDHP-UHFFFAOYSA-N 1-[chloro(methyl)phosphoryl]ethane Chemical compound CCP(C)(Cl)=O KJKWGCTWYJCDHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- CVNMBKFJYRAHPO-UHFFFAOYSA-N [chloro(methyl)phosphoryl]methane Chemical compound CP(C)(Cl)=O CVNMBKFJYRAHPO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008719 thickening Effects 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
-
- 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
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519192 DE2519192C2 (de) | 1975-04-30 | 1975-04-30 | Verfahren zur Herstellung phosphorhaltiger Ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7602715L SE7602715L (sv) | 1976-10-31 |
| SE424639B true SE424639B (sv) | 1982-08-02 |
Family
ID=5945377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7602715A SE424639B (sv) | 1975-04-30 | 1976-02-27 | Sett att framstella fosforhaltiga estrar |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5926633B2 (da) |
| AT (1) | AT340949B (da) |
| BE (1) | BE841273A (da) |
| CA (1) | CA1050562A (da) |
| CH (1) | CH612944A5 (da) |
| DD (1) | DD125691A5 (da) |
| DE (1) | DE2519192C2 (da) |
| DK (1) | DK191976A (da) |
| FR (1) | FR2309563A1 (da) |
| GB (1) | GB1490835A (da) |
| IT (1) | IT1061688B (da) |
| NL (1) | NL183401C (da) |
| SE (1) | SE424639B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3245365A1 (de) * | 1982-12-08 | 1984-06-14 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von alkanphosphonigsaeureestern |
| BR112018006414B1 (pt) | 2015-09-29 | 2020-11-24 | Bayer Cropscience Aktiengesellschaft | processo para produzir fosfinatos |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2631161A (en) * | 1949-02-26 | 1953-03-10 | Universal Oil Prod Co | Manufacture of dimethyl hydrogen phosphite |
| DE1078558B (de) * | 1958-08-25 | 1960-03-31 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von Dialkylphosphiten mit ungleichen Alkylresten |
| US3042697A (en) * | 1958-10-28 | 1962-07-03 | Gulf Research Development Co | Process for making phosphorus acid esters |
| DE2415757C2 (de) * | 1974-04-01 | 1982-10-14 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung phosphorhaltiger Ester |
-
1975
- 1975-04-30 DE DE19752519192 patent/DE2519192C2/de not_active Expired
-
1976
- 1976-02-27 SE SE7602715A patent/SE424639B/sv not_active IP Right Cessation
- 1976-03-23 CH CH361476A patent/CH612944A5/xx not_active IP Right Cessation
- 1976-04-09 CA CA249,987A patent/CA1050562A/en not_active Expired
- 1976-04-13 GB GB1505876A patent/GB1490835A/en not_active Expired
- 1976-04-23 NL NL7604373A patent/NL183401C/xx not_active IP Right Cessation
- 1976-04-26 IT IT4917376A patent/IT1061688B/it active
- 1976-04-28 DD DD19256876A patent/DD125691A5/xx unknown
- 1976-04-28 AT AT310776A patent/AT340949B/de not_active IP Right Cessation
- 1976-04-29 DK DK191976A patent/DK191976A/da unknown
- 1976-04-29 BE BE166564A patent/BE841273A/xx not_active IP Right Cessation
- 1976-04-30 FR FR7613031A patent/FR2309563A1/fr active Granted
- 1976-04-30 JP JP4978976A patent/JPS5926633B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2519192A1 (de) | 1976-11-11 |
| DE2519192C2 (de) | 1983-08-04 |
| ATA310776A (de) | 1977-05-15 |
| BE841273A (fr) | 1976-10-29 |
| JPS51136624A (en) | 1976-11-26 |
| CH612944A5 (en) | 1979-08-31 |
| AT340949B (de) | 1978-01-10 |
| CA1050562A (en) | 1979-03-13 |
| IT1061688B (it) | 1983-04-30 |
| NL183401C (nl) | 1988-10-17 |
| DD125691A5 (da) | 1977-05-11 |
| SE7602715L (sv) | 1976-10-31 |
| FR2309563B1 (da) | 1982-11-12 |
| JPS5926633B2 (ja) | 1984-06-29 |
| FR2309563A1 (fr) | 1976-11-26 |
| DK191976A (da) | 1976-10-31 |
| GB1490835A (en) | 1977-11-02 |
| NL7604373A (nl) | 1976-11-02 |
| NL183401B (nl) | 1988-05-16 |
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