GB853982A - Production of alkyl, aryl and aralkyl esters of acids of trivalent phosphorus - Google Patents
Production of alkyl, aryl and aralkyl esters of acids of trivalent phosphorusInfo
- Publication number
- GB853982A GB853982A GB8796/57A GB879657A GB853982A GB 853982 A GB853982 A GB 853982A GB 8796/57 A GB8796/57 A GB 8796/57A GB 879657 A GB879657 A GB 879657A GB 853982 A GB853982 A GB 853982A
- Authority
- GB
- United Kingdom
- Prior art keywords
- addition
- ammonia
- maintained
- aryl
- preparation
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 title abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 title abstract 3
- 125000003118 aryl group Chemical group 0.000 title abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 3
- 239000011574 phosphorus Substances 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 9
- 229910021529 ammonia Inorganic materials 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- -1 phosphorus halide Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- DWDIJHMTKXSZIJ-UHFFFAOYSA-N CCCCOP(CC)(CC)O Chemical compound CCCCOP(CC)(CC)O DWDIJHMTKXSZIJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- NSSMTQDEWVTEKN-UHFFFAOYSA-N diethoxy(methyl)phosphane Chemical compound CCOP(C)OCC NSSMTQDEWVTEKN-UHFFFAOYSA-N 0.000 abstract 1
- ILJTUHMTZJCBTM-UHFFFAOYSA-N diethoxy(octyl)phosphane Chemical compound C(CCCCCCC)P(OCC)OCC ILJTUHMTZJCBTM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- XIOCVTRMYXHGFQ-UHFFFAOYSA-N dihexoxy(phenyl)phosphane Chemical compound C1(=CC=CC=C1)P(OCCCCCC)OCCCCCC XIOCVTRMYXHGFQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical class CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 abstract 1
- QBMIXMIYIRKOME-UHFFFAOYSA-N ethyl(dioctoxy)phosphane Chemical compound C(C)P(OCCCCCCCC)OCCCCCCCC QBMIXMIYIRKOME-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 102220104176 rs1114167296 Human genes 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical class CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 abstract 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; 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
- C07F9/28—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)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Esters of acids of trivalent phosphorus having the formula P(OR)3, R1P(OR)2, R12P(OR), (HO)P(OR)2 or HOR1P(OR), wherein R is an aryl, aralkyl or alkyl group having at least 2 carbon atoms and R1 an aryl, aralkyl or alkyl group are prepared by the separate simultaneous addition of a phosphorus halide, R 3-he-n PX n, where X is chlorine, bromine or iodine and n is 2 or 3, and the calculated proportion of ammonia gas to at least the calculated proportion of an alcohol or phenol ROH, the addition being so regulated that the ammonia addition is completed in substantially the same time as the addition of the phosphorous halide, the reaction temperature being maintained at from-25 DEG C. to about 65 DEG C., with the limitation that for the preparation of neutral phosphites the temperture is maintained above 25 DEG C., and the pH at 7-8,5 for the preparation of neutral esters and 5,5-6,9 for acid esters. In a modification of this process for the production of acid esters, (HO)P (OR)2 and (HO)R1P(OR), the ammonia addition is completed in two-thirds or one-half, respectively of the time taken to add the phosphorous halide, the pH being maintained at 7-8,5 during the addition of the ammonia. An inert hydrocarbon solvent may be used. The required pH may be maintained by the use of proportioning pumps to add the reactants or by means of an electronic or chemical indicator, e.g. just basic to Methyl Red for pH7-8,5. The process may be operated in a continuous manner. The required amount of ammonia and the minimum required amount of hydroxy compound may be obtained from the following equations. <FORM:0853982/IV(b)/1> <FORM:0853982/IV(b)/2> <FORM:0853982/IV(b)/3> <FORM:0853982/IV(b)/4> <FORM:0853982/IV(b)/5> Examples describe the preparation of triethyl, triisopropyl, tributyl, triisooctyl, trioctyl, trinonyl and tridecyl phosphites, dimethyl, diethyl, dipropyl and diisopropyl hydrogen phosphites, diethyl methylphosphonite, dioctyl ethylphosphonite, dihexyl phenylphosphonite, diethyl octylphosphonite and butyl diethylphosphonite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US853982XA | 1956-04-16 | 1956-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB853982A true GB853982A (en) | 1960-11-16 |
Family
ID=22191349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8796/57A Expired GB853982A (en) | 1956-04-16 | 1957-03-18 | Production of alkyl, aryl and aralkyl esters of acids of trivalent phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB853982A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247448A (en) | 1978-11-02 | 1981-01-27 | General Electric Company | Thermally stable polycarbonate compositions comprising oxetane phosphonites |
| EP0787738A1 (en) * | 1996-02-01 | 1997-08-06 | Hoechst Aktiengesellschaft | Process for the preparation of 6-alkoxy-(6H)-dibenz(c,e)(1,2)-oxaphosphorines |
| EP0789027A1 (en) * | 1996-02-06 | 1997-08-13 | Hoechst Aktiengesellschaft | Process for preparing monoalkylesters of phosphonous acids |
-
1957
- 1957-03-18 GB GB8796/57A patent/GB853982A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247448A (en) | 1978-11-02 | 1981-01-27 | General Electric Company | Thermally stable polycarbonate compositions comprising oxetane phosphonites |
| EP0787738A1 (en) * | 1996-02-01 | 1997-08-06 | Hoechst Aktiengesellschaft | Process for the preparation of 6-alkoxy-(6H)-dibenz(c,e)(1,2)-oxaphosphorines |
| US5698729A (en) * | 1996-02-01 | 1997-12-16 | Hoechst Aktiengesellschaft | Process for preparing 6-alkoxy-(6H)-dibenzo C,E! 1,2!-oxaphosphorines |
| EP0789027A1 (en) * | 1996-02-06 | 1997-08-13 | Hoechst Aktiengesellschaft | Process for preparing monoalkylesters of phosphonous acids |
| US5734072A (en) * | 1996-02-06 | 1998-03-31 | Hoechst Aktiengesellschaft | Process for preparing monoalkyl phosphonites |
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