WO1998039340A1 - Process for preparing alkyl-1-alkoxyethylphosphinous acids - Google Patents
Process for preparing alkyl-1-alkoxyethylphosphinous acids Download PDFInfo
- Publication number
- WO1998039340A1 WO1998039340A1 PCT/EP1998/000985 EP9800985W WO9839340A1 WO 1998039340 A1 WO1998039340 A1 WO 1998039340A1 EP 9800985 W EP9800985 W EP 9800985W WO 9839340 A1 WO9839340 A1 WO 9839340A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- acetaldehyde
- acids
- general formula
- alkoxyethylphosphinous
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 14
- 150000007513 acids Chemical class 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- -1 alkyl dichlorophosphanes Chemical class 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
- 150000001241 acetals Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- JHNJGLVSPIMBLD-UHFFFAOYSA-N dichloro(ethyl)phosphane Chemical compound CCP(Cl)Cl JHNJGLVSPIMBLD-UHFFFAOYSA-N 0.000 claims description 3
- LSMMTQDEKKQXAG-UHFFFAOYSA-N dichloro(propan-2-yl)phosphane Chemical compound CC(C)P(Cl)Cl LSMMTQDEKKQXAG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- HVFIQVINDMYLRU-UHFFFAOYSA-N 1-ethoxyethyl(methyl)phosphinic acid Chemical compound CCOC(C)P(C)(O)=O HVFIQVINDMYLRU-UHFFFAOYSA-N 0.000 description 1
- IACYCGGYWPYWFH-UHFFFAOYSA-N 1-methoxyethyl(methyl)phosphinic acid Chemical compound COC(C)P(C)(O)=O IACYCGGYWPYWFH-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CJYWQTOGKMPYEW-UHFFFAOYSA-N ethyl(1-methoxyethyl)phosphinic acid Chemical compound CCP(O)(=O)C(C)OC CJYWQTOGKMPYEW-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
Definitions
- the invention relates to a process for the preparation of alkyl-1-alkoxyethylphosphinic acids.
- Alkyl 1-alkoxyethylphosphinic acids are valuable intermediates for the production of flame retardants. These acids are usually prepared by hydrolysis of the corresponding acid chlorides, which are prepared by reacting alkyldichlorophosphanes with acetaldehyde acetals (Tsivunin et al., Zh. Obshch. Khim. 40 (102) 1970, 12, 2560). The unsatisfactory yields are disadvantageous in this process, since the acid chlorides are obtained in yields of 60-70% of theory. Technically simple production processes for alkyl-1-alkoxyethylphosphinic acids are therefore sought.
- the invention relates to a process for the preparation of alkyl-1-alkoxyethylphosphinic acids of the general formula (I)
- R 1 represents a straight-chain or branched alkyl radical having 1 to 6 carbon atoms, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl and R 2 represents a straight-chain or branched alkyl radical having 1 to 4 carbon - Atoms, preferably methyl or ethyl, characterized in that alkyl dichlorophosphanes of the general formula (II)
- Suitable starting materials of the general formula (II) are, for example, dichloromethylphosphine, dichloroethylphosphane and dichloroisopropylphosphine. Dichloromethylphosphine is preferred.
- Suitable starting materials of the general formula (III) are in particular acetaldehyde dimethyl acetal and acetaldehyde diethylacetyl.
- the reactants are used in a molar ratio of alkyl dichlorophosphane to acetaldehyde dialkyl acetal from 1: 1 to 1: 2, preferably from 1: 1 to 1: 1, 2.
- the components are mixed slowly with cooling.
- the reaction temperatures are -20 to 150 ° C, preferably -15 to 60 ° C.
- the resulting reaction mixture can, if appropriate, be freed of low boilers and water is then added without further purification measures.
- the molar ratio of alkyl di chlorophosphine to water must be at least 1: 1. Excesses are possible and especially useful if the crude acid is to be processed directly without further purification.
- the method of the present invention can also be designed continuously.
- a distillation process can in particular be carried out as a cleaning operation for the acids according to the invention.
- Transition temperature of 146-151 ° C gave 140 g of 1-methoxyethyl-ethylphosphinic acid. This corresponds to a yield of 89% of theory.
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
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP53810698A JP2001513787A (en) | 1997-03-04 | 1998-02-20 | Method for producing alkyl- (1-alkoxyethyl) phosphinic acid |
EP98910711A EP0971937A1 (en) | 1997-03-04 | 1998-02-20 | Process for preparing alkyl-1-alkoxyethylphosphinous acids |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19708722.1 | 1997-03-04 | ||
DE19708722A DE19708722A1 (en) | 1997-03-04 | 1997-03-04 | Process for the preparation of alkyl-1-alkoxyethylphosphinic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998039340A1 true WO1998039340A1 (en) | 1998-09-11 |
Family
ID=7822164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/000985 WO1998039340A1 (en) | 1997-03-04 | 1998-02-20 | Process for preparing alkyl-1-alkoxyethylphosphinous acids |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0971937A1 (en) |
JP (1) | JP2001513787A (en) |
DE (1) | DE19708722A1 (en) |
WO (1) | WO1998039340A1 (en) |
ZA (1) | ZA981771B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2736914B1 (en) | 2011-07-29 | 2016-07-06 | Straitmark Holding AG | Method for the manufacture of compounds containing an alpha-oxy phosphorus group by using p-x components |
EP2567961A1 (en) * | 2011-09-08 | 2013-03-13 | Straitmark Holding AG | Method for the manufacture of compounds containing an alpha-oxyphosphorus group by using an activator |
-
1997
- 1997-03-04 DE DE19708722A patent/DE19708722A1/en not_active Withdrawn
-
1998
- 1998-02-20 EP EP98910711A patent/EP0971937A1/en not_active Withdrawn
- 1998-02-20 JP JP53810698A patent/JP2001513787A/en active Pending
- 1998-02-20 WO PCT/EP1998/000985 patent/WO1998039340A1/en not_active Application Discontinuation
- 1998-03-03 ZA ZA981771A patent/ZA981771B/en unknown
Non-Patent Citations (3)
Title |
---|
CHEMICAL ABSTRACTS, vol. 075, no. 3, 19 July 1971, Columbus, Ohio, US; abstract no. 020518, TSIVUNIN V S ET AL: "Reaction of the diethylamido acid chloride of ethylphosphinous acid and ethyldichlorophosphine with orthoformic ester and the diethylacetal of acetaldehyde" XP002067161 * |
PETROV K.A.: "Alkoxymethylation of phenylphosphonous dichloride and diphenylphosphinous chloride with dialkoxymethanes", JOURNAL OF GENERAL CHEMISTRY USSR., vol. 50, no. 7, December 1980 (1980-12-01), NEW YORK US, pages 1220 - 1224, XP002067160 * |
ZH. OBSHCH. KHIM. (ZOKHA4);70; VOL.40 (12); PP.2560-3, USSR * |
Also Published As
Publication number | Publication date |
---|---|
ZA981771B (en) | 1998-09-04 |
EP0971937A1 (en) | 2000-01-19 |
JP2001513787A (en) | 2001-09-04 |
DE19708722A1 (en) | 1998-09-10 |
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