US2003083530A1PendingUtilityA1
Metal salts of hindered aromatic phenols
Est. expirySep 29, 2020(expired)· nominal 20-yr term from priority
C07C 37/66C07C 37/64
42
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Claims
Abstract
Reaction of a phenol with a metal salt of an alcohol produces a metal phenolate salt of a phenol. When a hindered phenol is used a hindered metal phenolate is produced. Such hindered metal phenolate salts are useful in driving the synthesis reaction of hindered phenol esters and phosphite esters to completion.
Claims
exact text as granted — not AI-modifiedHaving described the invention, that which is claimed is:
1 . A process for the preparation of a metal phenolate comprising reacting a phenol having the formula:
wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, t-hexyl, cyclohexyl, cumyl, t-pentyl, and t-octyl with a metal alcoholate having the formula (R 4 O) x Q where R 4 O is derived from the corresponding alcohol R 4 OH, Q is a metal cation having a valence x, to produce a metal phenolate and an alcohol R 4 OH wherein said metal phenolate has the formula:
wherein Q, x and each R 1 , R 2 , and R 3 are as previously defined and removing the alcohol R 4 OH from the metal phenolate.
2 . The process of claim 1 . A process for the preparation of a metal phenolate comprising reacting a phenol having the formula:
wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, t-hexyl, cyclohexyl, cumyl, t-pentyl, and t-octyl with a metal alcoholate having the formula (R 4 O) x Q where R 4 O is derived from the corresponding alcohol R 4 OH, Q is a metal cation having a valence x, to produce a metal phenolate and an alcohol R 4 OH wherein said metal phenolate has the formula:
wherein Q, x and each R 1 , R 2 , and R 3 are as previously defined and removing the alcohol R 4 OH from the metal phenolate.
3 . The process of claim 1 wherein R 4 is a monovalent organic radical having from one to twenty carbon atoms.
4 . The process of claim 2 wherein R 4 is a monovalent organic radical having from one to twenty carbon atoms.
5 . The process of claim 1 wherein R 4 is selected from the group consisting of methyl, ethanyl, n-propyl, iso-propyl, n-butyl, 2-butyl, 2-methyl-propyl and tertiary butyl.
6 . The process of claim 2 wherein R 4 is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, 2-methyl-propyl and tertiary butyl.
7 . The process of claim 1 where Q is selected from the group consisting of the alkali metals, the alkaline earth metals, the transition metals and the non-transition metals of Groups III, IV and V subject to the limitation that the halides of these metals are ionic salts.
8 . The process of claim 2 where Q is selected from the group consisting of the alkali metals, the alkaline earth metals, the transition metals and the non-transition metals of Groups III, IV and V subject to the limitation that the halides of these metals are ionic salts.
9 . The process of claim 1 wherein wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, and t-hexyl.
10 . The process of claim 2 wherein wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, and t-hexyl.
11 . The process of claim 2 wherein the solvent is selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, halogentated aliphatic hydrocarbons, halogenated aromatic hydrocarbons, esters, ketones, ethers, glycolethers, nitrogen compounds, carbon disulfide, dimethyl sulfoxide; phosphorus compounds such as hexamethylphosphoramide; and combinations thereof.
12 . The process of claim 11 where the nitrogen compounds are amines.
13 . The process of claim 12 where the amine is tri-n-propyl amine.
14 . The process of claim 13 where each R 1 , R 2 , and R 3 is t-butyl.
15 . The process of claim 14 where Q is an alkali metal.
16 . The process of claim 15 where the alkali metal is sodium.
17 . The process of claim 16 where R 4 is methyl.
18 . A process for the preparation of a metal phenolate consisting essentially of reacting a phenol having the formula:
wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, t-hexyl, cyclohexyl, cumyl, t-pentyl, and t-octyl with a metal alcoholate having the formula (R 4 O) x Q where R 4 O is derived from the corresponding alcohol R 4 OH, Q is a metal cation having a valence x, to produce a metal phenolate and an alcohol R 4 0H wherein said metal phenolate has the formula:
wherein Q, x and each R 1 , R 2 , and R 3 are as previously defined and removing the alcohol R 4 OH from the metal phenolate.
19 . The process of claim 18 conducted in the presence of a solvent.
20 . A process for the preparation of a metal phenolate consisting of reacting a phenol having the formula:
wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, t-amyl, t-hexyl, cyclohexyl, cumyl, t-pentyl, and t-octyl with a metal alcoholate having the formula (R 4 O) x Q where R 4 O is derived from the corresponding alcohol R 4 OH, Q is a metal cation having a valence x, to produce a metal phenolate and an alcohol R 4 OH wherein said metal phenolate has the formula:
wherein Q, x and each R 1 , R 2 , and R 3 are as previously defined and removing the alcohol R 4 OH from the metal phenolate.Join the waitlist — get patent alerts
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