GB1064509A – Process for the manufacture of monofluorophosphoric acid and its monoesters
– Google Patents
GB1064509A – Process for the manufacture of monofluorophosphoric acid and its monoesters
– Google Patents
Process for the manufacture of monofluorophosphoric acid and its monoesters
Info
Publication number
GB1064509A
GB1064509A
GB53025/65A
GB5302565A
GB1064509A
GB 1064509 A
GB1064509 A
GB 1064509A
GB 53025/65 A
GB53025/65 A
GB 53025/65A
GB 5302565 A
GB5302565 A
GB 5302565A
GB 1064509 A
GB1064509 A
GB 1064509A
Authority
GB
United Kingdom
Prior art keywords
salt
h3po4
acid
reaction
pyridine
Prior art date
1965-01-27
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
Application number
GB53025/65A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck KGaA
Original Assignee
E Merck AG
Priority date (The priority date 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 date listed.)
1965-01-27
Filing date
1965-12-14
Publication date
1967-04-05
1965-12-14
Application filed by E Merck AG
filed
Critical
E Merck AG
1967-04-05
Publication of GB1064509A
publication
Critical
patent/GB1064509A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C01—INORGANIC CHEMISTRY
C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
C01B25/00—Phosphorus; Compounds thereof
C—CHEMISTRY; METALLURGY
C01—INORGANIC CHEMISTRY
C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
C01B25/00—Phosphorus; Compounds thereof
C01B25/10—Halides or oxyhalides of phosphorus
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 System
C07F9/02—Phosphorus compounds
C07F9/06—Phosphorus compounds without P—C bonds
C07F9/08—Esters of oxyacids of phosphorus
C07F9/09—Esters of phosphoric acids
C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
C07H19/06—Pyrimidine radicals
C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
C07H19/16—Purine radicals
C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
Abstract
Monofluorophosphoric acid esters are prepared by reacting a monoester of H3PO4 or a monoester salt of H3PO4 with HF in the presence of trichloroacetonitrile and/or dicyclohexyl-carbodiimide and a tertiary aliphatic amine and/or a heterocyclic base containing tertiary N as acid binding agent. The product may be hydrolysed and isolated as an alkli metal, e.g. Na, K, Li or NH4+, salt or cyclohexylammonium salt. The reaction temperature may be -10 DEG to +150 DEG C. Binding agents specified are pyridine, collidine, lutidine, trimethyl, triethyl or tributyl amine. The ester group may be alkyl, aryl or aralkyl, normally containing not more than 25 C atoms, e.g. nucleosides. The reaction may be performed in a solvent, e.g. acetonitrile pyridine or dimethylformamide and the HF may be in aqueous solution. The product may be purified by ion exchange. When ribo-nucleotides are reacted with HF and trichloroacetonitrile, 21,31-O-(1-trichloro-2-amino) – ethylidene – nucleotides are formed along with the monofluorophosphate. The former compounds, with dilute acid at room temperature form nucleoside-51-monoflourophosphate in quantitative yield. Under alkaline conditions the reaction is slower, further hydrolysis with stronger bases yields nucleosides and nucleobases. Specified nucleotides are adenosine-, uridine- and guanosine-51-phosphates.ALSO:Monofluorophosphoric acid and its esters and salts, e.g. alkali metal or NH4+, are prepared by reacting H3PO4, a mono ester of H3PO4 or a salt of phosphoric acid or an ester thereof with HF in the presence of trichloroacetonitrile and/or dicyclohexylcarbodiimide and a tertiary aliphatic amine and/or a heterocyclic base containing tertiary N as acid binding agent. The product may be hydrolysed and isolated as an alkali metal, e.g. Na, K, Li or NH4+ salt or cyclohexylammonium salt. The reaction temp. may be – 10 DEG to + 150 DEG C. The binding agent may be a tertiary amine, e.g. pyridine, collidine, lutidine, trimethyl, triethyl or tributyl amine. The ester group may be alkyl, aryl or aralkyl, normally containing not more than 25 C atoms, e.g. nucleotides. The reaction may be performed in a solvent, e.g. acetonitrile, pyridine or dimethylformamide, and the HF may be in aqueous solution. The product may be purified by ion exchange. Using free H3PO4 and excess HF and condensing agent polyfluorinated, e.g. difluorophosphoric, acids are obtained and may be hydrolysed, preferably in weak alkaline medium, to the monofluorophosphoric acid salt.
GB53025/65A
1965-01-27
1965-12-14
Process for the manufacture of monofluorophosphoric acid and its monoesters
Expired
GB1064509A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
DEM63945A
DE1264423B
(en)
1965-01-27
1965-01-27
Process for the preparation of monofluorophosphoric acid and its monoesters
Publications (1)
Publication Number
Publication Date
GB1064509A
true
GB1064509A
(en)
1967-04-05
Family
ID=7310968
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB53025/65A
Expired
GB1064509A
(en)
1965-01-27
1965-12-14
Process for the manufacture of monofluorophosphoric acid and its monoesters
Country Status (7)
Country
Link
US
(1)
US3424550A
(en)
BR
(1)
BR6676263D0
(en)
CH
(1)
CH498047A
(en)
DE
(1)
DE1264423B
(en)
FR
(1)
FR1464472A
(en)
GB
(1)
GB1064509A
(en)
NL
(1)
NL6516242A
(en)
Families Citing this family (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4108950A
(en)
*
1977-04-29
1978-08-22
The United States Of America As Represented By The Secretary Of The Army
Process for preparing organophosphorus and organophosphono fluorines
DE3714051A1
(en)
*
1987-04-28
1988-11-17
Desowag Materialschutz Gmbh
AGENTS FOR THE PRESERVATION OF WOOD AND WOOD MATERIAL
US5659060A
(en)
*
1996-11-07
1997-08-19
Witco Corporation
Process for making aryl fluorophosphites useful as stabilizers
Family Cites Families (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US2408784A
(en)
*
1943-03-11
1946-10-08
Ozark Chemical Company
Anhydrous monofluorophosphoric acid and method of producing it
US2481807A
(en)
*
1947-11-28
1949-09-13
Ozark Mahoning Co
Method of producing monofluorophosphates
1965
1965-01-27
DE
DEM63945A
patent/DE1264423B/en
active
Pending
1965-10-27
CH
CH1482265A
patent/CH498047A/en
not_active
IP Right Cessation
1965-12-14
NL
NL6516242A
patent/NL6516242A/xx
unknown
1965-12-14
GB
GB53025/65A
patent/GB1064509A/en
not_active
Expired
1966
1966-01-06
BR
BR176263/66A
patent/BR6676263D0/en
unknown
1966-01-19
FR
FR46419A
patent/FR1464472A/en
not_active
Expired
1966-01-20
US
US521804A
patent/US3424550A/en
not_active
Expired – Lifetime
Also Published As
Publication number
Publication date
CH498047A
(en)
1970-10-31
DE1264423B
(en)
1968-03-28
NL6516242A
(en)
1966-07-28
BR6676263D0
(en)
1973-08-28
FR1464472A
(en)
1966-12-30
US3424550A
(en)
1969-01-28
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