Process for the preparation of fluoroformates
First Claim
1. A process for the preparation of fluoroformates of formula:
- ##STR10## wherein R1 is an unsubstituted saturated or unsaturated, aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms, a saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms substituted by an hydrocarbon radical or by at least one halogen atom, araliphatic radical of up to 24 carbon atoms which is unsubstituted or substituted by an hydrocarbon radical or by at least one halogen atom, or an aromatic radical of up to 24 carbon atoms, which consists of reacting a carbonate of formula;
##STR11## wherein R1 has the same meaning as hereinabove and R2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R2 is aryl, unsubstituted or substituted by one or more halogen atoms, with 1-5 equivalents of an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride of formula FNR3 R4 R5 R6, wherein R3, R4, R5 and R6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is a member selected from the group consisting of KHF2, NH4 HF2 or KSO2 F, said fluoride being activated by 1-10% by weight of a complexing agent for the cation in the fluoride which is a cryptate, a cyclic or linear polyether or being activated by a polar aprotic compound, at a temperature between 20° and
120°
C., whereby said carbonate is split to give a reaction mixture containing an aldehyde of formula R2 CHO and said fluoroformate, separating from the reaction mixture at least one of said fluoroformate and said aldehyde as soon as formed and recovering said fluoroformate.
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Abstract
A process for the preparation of fluoroformates of formula: ##STR1## in which R1 is a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical, or substituted or unsubstituted araliphatic radical or an aromatic radical, which consists of reacting a carbonate of formula: ##STR2## in which R1 has the same meaning as hereinabove and R2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R2 is aryl, unsubstituted or substituted by one or more halogen atoms, with an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride, of formula FNR3 R4 R5 R6, wherein R3, R4, R5, R6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is KHF2, NH4 HF2 or KSO2 F. The fluoride is activated by a complexing agent for the cation which is a cryptate, a cyclic or linear polyether or by means of a polar aprotic compound. The carbonate is split to give a reaction mixture containing an aldehyde and the fluoroformate which is removed from the reaction mixture.
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Citations
17 Claims
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1. A process for the preparation of fluoroformates of formula:
- ##STR10## wherein R1 is an unsubstituted saturated or unsaturated, aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms, a saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms substituted by an hydrocarbon radical or by at least one halogen atom, araliphatic radical of up to 24 carbon atoms which is unsubstituted or substituted by an hydrocarbon radical or by at least one halogen atom, or an aromatic radical of up to 24 carbon atoms, which consists of reacting a carbonate of formula;
##STR11## wherein R1 has the same meaning as hereinabove and R2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R2 is aryl, unsubstituted or substituted by one or more halogen atoms, with 1-5 equivalents of an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride of formula FNR3 R4 R5 R6, wherein R3, R4, R5 and R6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is a member selected from the group consisting of KHF2, NH4 HF2 or KSO2 F, said fluoride being activated by 1-10% by weight of a complexing agent for the cation in the fluoride which is a cryptate, a cyclic or linear polyether or being activated by a polar aprotic compound, at a temperature between 20° and
120°
C., whereby said carbonate is split to give a reaction mixture containing an aldehyde of formula R2 CHO and said fluoroformate, separating from the reaction mixture at least one of said fluoroformate and said aldehyde as soon as formed and recovering said fluoroformate. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
- ##STR10## wherein R1 is an unsubstituted saturated or unsaturated, aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms, a saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical of up to 24 carbon atoms substituted by an hydrocarbon radical or by at least one halogen atom, araliphatic radical of up to 24 carbon atoms which is unsubstituted or substituted by an hydrocarbon radical or by at least one halogen atom, or an aromatic radical of up to 24 carbon atoms, which consists of reacting a carbonate of formula;
Specification
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- Resources
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Current AssigneeSociete Nationale Des Poudres Et Explosifs (Government of France)
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Original AssigneeSociete Nationale Des Poudres Et Explosifs (Government of France)
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InventorsSenet, Jean-Pierre, Piteau, Marc, Olofson, Roy A., Dang, Vu A., Wolf, Patrick
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Primary Examiner(s)NOT, DEFINED
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Assistant Examiner(s)Kapner, Stephen M.
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Application NumberUS06/651,661Time in Patent Office729 DaysField of Search260/463US Class Current558/282CPC Class CodesC07C 68/06 from organic carbonatesC07C 69/96 Esters of carbonic or halof...
