GB810642A - A process for the preparation of esters of acylphosphorous acids - Google Patents
A process for the preparation of esters of acylphosphorous acidsInfo
- Publication number
- GB810642A GB810642A GB14121/57A GB1412157A GB810642A GB 810642 A GB810642 A GB 810642A GB 14121/57 A GB14121/57 A GB 14121/57A GB 1412157 A GB1412157 A GB 1412157A GB 810642 A GB810642 A GB 810642A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- acid
- give
- chloride
- phosphite
- 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 9
- 150000007513 acids Chemical class 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 3
- -1 carboxylic acid halide Chemical class 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WQCRMVOOMCEJJY-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)P(O)(O)O Chemical compound C(CCCCCCCCCCC)(=O)P(O)(O)O WQCRMVOOMCEJJY-UHFFFAOYSA-N 0.000 abstract 1
- GEQZNVRUHDONAP-UHFFFAOYSA-N CCCCC(CC)C(P(O)(O)OCC)=O Chemical compound CCCCC(CC)C(P(O)(O)OCC)=O GEQZNVRUHDONAP-UHFFFAOYSA-N 0.000 abstract 1
- UJAPIHXXMFVWEE-UHFFFAOYSA-N CCCCC(CC)COP(C(C(CC)CCCC)=O)(O)O Chemical compound CCCCC(CC)COP(C(C(CC)CCCC)=O)(O)O UJAPIHXXMFVWEE-UHFFFAOYSA-N 0.000 abstract 1
- TZROXHVFGCUOES-UHFFFAOYSA-N CCCCCCCCCCCC(P(O)(O)OCCCC)=O Chemical compound CCCCCCCCCCCC(P(O)(O)OCCCC)=O TZROXHVFGCUOES-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- GGCXLVWDCPTFMN-UHFFFAOYSA-N bis(2-chloroethyl) hydrogen phosphite Chemical compound ClCCOP(O)OCCCl GGCXLVWDCPTFMN-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 abstract 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000003977 halocarboxylic acids Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000009884 interesterification Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 238000005292 vacuum distillation Methods 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
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Acid esters of acylphosphorous acids are prepared by heating halides of mono- or poly-basic carboxylic acids with saturated dialiphatic or dicycloaliphatic phosphites. The hydrocarbon residues of the phosphite preferably contain less than 8 carbon atoms and may be substituted, e.g. by halogen. Specified phosphites include dialkyl phosphites and di-(2-chloroethyl) phosphite. The carboxylic acid halide is preferably a chloride or bromide and may be derived from an aliphatic, cycloaliphatic or aromatic mono-, di- or polycarboxylic acid, the hydrocarbon residue(s) of which may carry substituents or be interrupted by hetero atoms. Specified halides include those of lower and higher fatty acids, halocarboxylic acids, e.g. chloracetic acids, ethercarboxylic acids, thioethercarboxylic acids, aminocarboxylic acids, cyclohexane carboxylic acid, benzoic acid, aliphatic and aromatic polycarboxylic acids and tetrachlorophthallic acid. Stoichiometric proportions are preferably used. Preferred reaction temperatures are 50-150 DEG C. An organic solvent may be present, e.g. CCl4 or benzene. The alkyl halide formed as by-product may be distilled off continuously during the reaction or removed subsequently by vacuum distillation according to its molecular weight. The products may be converted into their salts, e.g. alkali metal salts, which may be surface-active agents or may be subjected to interesterification, preferably with high molecular weight alcohols or may be converted to the neutral esters. The products derived from poly carboxylic acids may be reacted with polyhydric alcohols to give acid or neutral polyesters. In example: (1) lauroyl chloride is heated with diethyl phosphite to give the monoethyl ester of lauroylphosphorous acid which is converted to the sodium salt; (2) to (4) diethyl phosphite is similarly reacted with adipic acid dichloride, benzoyl chloride and capric acid chloride respectively; (5) diethyl phosphite is heated with 2-ethylhexanoic acid chloride to give monoethyl 2-ethylhexanoylphosphite which is interesterified with 2-ethylhexanol to give mono-2-ethylhexyl 2-ethylhexanoylphosphite; (6) lauroyl chloride and dibutyl phosphite are heated in a stream of nitrogen to give monobutyl lauroylphosphite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH26995A DE1010965B (en) | 1956-05-08 | 1956-05-08 | Process for the preparation of acidic esters of acylphosphonic acids or their salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB810642A true GB810642A (en) | 1959-03-18 |
Family
ID=7150451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14121/57A Expired GB810642A (en) | 1956-05-08 | 1957-05-03 | A process for the preparation of esters of acylphosphorous acids |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2900408A (en) |
| DE (1) | DE1010965B (en) |
| GB (1) | GB810642A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774262A (en) * | 1980-04-21 | 1988-09-27 | Minemet Recherche | Application of diphosphonic derivatives to cation exchange, new diphosphonic derivatives, and production process therefor |
| US5407969A (en) * | 1990-10-19 | 1995-04-18 | Kleiner; Hans-Jerg | Acyl-(2'-hydroxybiphenyl-2-yl)-phosphinic acid salts, their preparation and use |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118876A (en) * | 1958-07-26 | 1964-01-21 | Takeda Pharmaceutical | Process for preparing glycoside phosphates |
| NL242785A (en) * | 1958-09-06 | 1900-01-01 | ||
| US3012054A (en) * | 1960-03-18 | 1961-12-05 | Dow Chemical Co | Tetraalkyl esters of diphosphonates |
| NL132418C (en) * | 1962-04-13 | |||
| US3324202A (en) * | 1963-07-09 | 1967-06-06 | Fmc Corp | Phosphorus-containing polyols |
| US3382060A (en) * | 1964-11-18 | 1968-05-07 | Chemagro Corp | Dialkyl and diphenyl esters of aryloxyacetyl-phosphonic acid as herbicides |
| US3400148A (en) * | 1965-09-23 | 1968-09-03 | Procter & Gamble | Phosphonate compounds |
| US3676532A (en) * | 1969-11-21 | 1972-07-11 | Olin Corp | Alpha-(dialkoxyphosphinyl)aryl methyl dialkyl phosphates |
| US3957858A (en) * | 1970-04-13 | 1976-05-18 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3940436A (en) * | 1970-04-13 | 1976-02-24 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3944599A (en) * | 1970-04-13 | 1976-03-16 | Monsanto Company | Substituted ethane diphosphonic acids and salts |
| US3899496A (en) * | 1970-10-06 | 1975-08-12 | Henkel & Cie Gmbh | Production of 1-aminoalkane-1,1-diphosphonic acids |
| DE2965566D1 (en) * | 1978-07-14 | 1983-07-07 | Basf Ag | Acylphosphinoxide compounds, their preparation and their use |
| US4339443A (en) * | 1978-09-22 | 1982-07-13 | Fbc Limited | Compounds and compositions |
| DE3039998A1 (en) * | 1980-10-23 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | PHOSPHONOFORMALDEHYDE, A METHOD FOR THE PRODUCTION THEREOF AND ITS USE AS AN INTERMEDIATE PRODUCT FOR THE PRODUCTION OF MEDICINAL PRODUCTS |
| US4911887A (en) * | 1988-11-09 | 1990-03-27 | W. R. Grace & Co.-Conn. | Phosphonic acid compounds and the preparation and use thereof |
| US5017306A (en) * | 1988-11-09 | 1991-05-21 | W. R. Grace & Co.-Conn. | Corrosion inhibitor |
| US5266722A (en) * | 1988-11-09 | 1993-11-30 | W. R. Grace & Co.-Conn. | Polyether bis-phosphonic acid compounds |
| US4981648A (en) * | 1988-11-09 | 1991-01-01 | W. R. Grace & Co.-Conn. | Inhibiting corrosion in aqueous systems |
| US5196409A (en) * | 1989-08-20 | 1993-03-23 | Yissum, Research Development Company Of The Hebrew University Of Jerusalem | Bisphosphonates, pharmaceutical compositions, and process for the treatment of irregularities in calcium metabolism |
| IL91362A0 (en) * | 1989-08-20 | 1990-03-19 | Yissum Res Dev Co | Bisphosphonates,process for preparing them and pharmaceutical compositions containing them |
| DE4240964A1 (en) * | 1992-12-05 | 1994-06-09 | Basf Ag | Arenebisphosphine oxides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2491920A (en) * | 1946-05-16 | 1949-12-20 | Du Pont | Diesters of 1-ketophosphonic acids |
| US2629731A (en) * | 1951-03-07 | 1953-02-24 | Shell Dev | Esters of phosphonoformic acids and polyhydric alcohols |
| US2719167A (en) * | 1953-04-13 | 1955-09-27 | Ciba Ltd | Compounds containing phosphorus and process therefor |
-
1956
- 1956-05-08 DE DEH26995A patent/DE1010965B/en active Pending
-
1957
- 1957-05-03 GB GB14121/57A patent/GB810642A/en not_active Expired
- 1957-05-07 US US657496A patent/US2900408A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774262A (en) * | 1980-04-21 | 1988-09-27 | Minemet Recherche | Application of diphosphonic derivatives to cation exchange, new diphosphonic derivatives, and production process therefor |
| US5156824A (en) * | 1980-04-21 | 1992-10-20 | Compagnie Francaise De Mokta | Application of diphosphonic derivatives to cation exchange, new diphosphonic derivatives and production process therefor |
| US5407969A (en) * | 1990-10-19 | 1995-04-18 | Kleiner; Hans-Jerg | Acyl-(2'-hydroxybiphenyl-2-yl)-phosphinic acid salts, their preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| US2900408A (en) | 1959-08-18 |
| DE1010965B (en) | 1957-06-27 |
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