Alkoxylated fatty esters and derivatives from natural oil metathesis
US-9506013-B2 · Nov 29, 2016 · US
US9540308B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9540308-B2 |
| Application number | US-201314420490-A |
| Country | US |
| Kind code | B2 |
| Filing date | Aug 2, 2013 |
| Priority date | Aug 24, 2012 |
| Publication date | Jan 10, 2017 |
| Grant date | Jan 10, 2017 |
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Method for producing an iron carboxylate, whereby it becomes possible to prevent the generation of hydrogen during the production of the iron carboxylate by the reaction of a carboxylic acid with metal iron. An embodiment of the present invention is a method for producing an iron carboxylate by reacting metal iron with a carboxylic acid in a reaction solution, wherein the reaction solution contains a non-iron metal having a standard electrode potential of −2.5 to 0.1 inclusive or a metal compound containing the metal, or the reaction solution contains at least one metal selected from the group consisting of Ag, Bi and Pd or a metal compound containing the metal.
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The invention claimed is: 1. A method for producing an iron carboxylate, the method comprising: reacting metal iron with at least one carboxylic acid selected from the group consisting of acrylic acid and methacrylic acid in a reaction liquid at a temperature of 110° C.-150° C., wherein: the reaction liquid comprises a metal other than iron having a standard electrode potential of from −2.5 to 0.1, or a metal compound comprising the relevant metal; or the reaction liquid comprises at least one metal selected from the group consisting of Ag, Bi and Pd, or a metal compound comprising the relevant metal. 2. The method according to claim 1 , wherein the reaction liquid comprises a metal other than iron having a standard electrode potential of from −2.5 to 0.1, or a metal compound comprising the relevant metal, and wherein a content of the metal other than iron having a standard electrode potential of −2.5 to 0.1 in the reaction liquid is from 0.00001 moles to 5 moles relative to 1 mole of the metal iron, or a content of the metal compound comprising the metal other than iron having a standard electrode potential of −2.5 to 0.1 in the reaction liquid is an amount such that the amount of the metal comprised in the metal compound is from 0.00001 moles to 5 moles relative to 1 mole of the metal iron. 3. The method according to claim 1 , wherein the reaction liquid comprises a metal other than iron having a standard electrode potential of from −2.5 to 0.1, or a metal compound comprising the relevant metal, and the standard electrode potential of the metal is from −0.44 to 0. 4. The method according to claim 2 , wherein the reaction liquid comprises a metal compound comprising a metal other than iron having a standard electrode potential of from −2.5 to 0.1; and wherein a total amount of an anion that is comprised in the reaction liquid and has a protonated form having a pKa, which is a negative common logarithm of an acid dissociation constant, in water at 25 ° C. of 2 or less is 10 moles or less relative to 1 mole of the metal iron in the reaction liquid. 5. The method according to claim 2 , wherein the reaction liquid comprises a metal compound comprising a metal other than iron having a standard electrode potential of from −2.5 to 0.1; and wherein the metal compound is an organometallic compound comprising the metal and an ionic ligand. 6. The method according to claim 1 , wherein the reaction liquid comprises at least one metal selected from the group consisting of Ag, Bi and Pd, or a metal compound comprising the relevant metal and wherein a content of the at least one metal selected from the group consisting of Ag, Bi and Pd in the reaction liquid is from 0.00001 moles to 5 moles relative to 1 mole of the metal iron, or a content of the metal compound comprising the at least one metal selected from the group consisting of Ag, Bi and Pd in the reaction liquid is an amount such that the amount of the metal comprised in the metal compound is from 0.00001 moles to 5 moles relative to 1 mole of the metal iron. 7. The method according to claim 6 , wherein the reaction liquid comprises at least one metal compound comprising a metal selected from the group consisting of Ag, Bi and Pd, and wherein a total amount of an anion that is comprised in the reaction liquid and has a protonated form having a pKa, which is a negative common logarithm of an acid dissociation constant, in water at 25° C. of 2 or less, is 10 moles or less relative to 1 mole of the metal iron in the reaction liquid. 8. The method according to claim 6 , wherein the reaction liquid comprises at least one metal compound comprising a metal selected from the group consisting of Ag, Bi and Pd, and the at least one metal compound is an organometallic compound comprising the metal and an ionic ligand. 9. A method for producing an iron carboxylate, the method comprising: reacting a metal iron with at least one carboxylic acid selected from the group consisting of acrylic acid and methacrylic acid in a reaction liquid at a temperature of 110° C.-150° C., wherein the reaction liquid comprises a Cu compound in an amount such that the amount of Cu comprised in the Cu compound is from 0.00001 moles to 5 moles relative to 1 mole of the metal iron; and the reaction liquid comprises an anion, whose protonated form has a pKa, which is a negative common logarithm of an acid dissociation constant, in water at 25° C. of 2 or less, in an amount f from 0.0001 moles to 10 moles relative to 1 mole of the metal iron. 10. The method according to claim 1 , wherein the iron carboxylate is an iron carboxylate comprising trivalent iron. 11. The method according to claim 1 , further comprising introducing an oxygen-comprising gas into the reaction liquid. 12. The method according to claim 1 , wherein: the reaction liquid comprises a metal other than iron having a standard electrode potential of from −2.5 to 0.1, or a metal compound comprising the relevant metal. 13. The method according to claim 1 , wherein: the reaction liquid comprises at least one metal selected from the group consisting of Ag, Bi and Pd, or a metal compound comprising the relevant metal. 14. The method according to claim 1 , comprising: reacting said metal iron with said at least one carboxylic acid selected from the group consisting of acrylic acid and methacrylic acid in a reaction liquid at a temperature of 120° C.-150° C. 15. The method according to claim 1 , comprising: reacting said metal iron with methacrylic acid in a reaction liquid at a temperature of 120° C.-150° C. 16. The method according to claim 9 , comprising: reacting said metal iron with said at least one carboxylic acid selected from the group consisting of acrylic acid and methacrylic acid in a reaction liquid at a temperature of 120° C.-150° C.
Acrylic acid esters; Methacrylic acid esters · CPC title
containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)} · CPC title
Acrylic acid; Methacrylic acid · CPC title
Ligands · CPC title
with an oxirane ring · CPC title
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