Articles comprising copolyesters produced with germanium catalyst
US-2024376258-A1 · Nov 14, 2024 · US
US12031107B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12031107-B2 |
| Application number | US-202117917514-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 30, 2021 |
| Priority date | Apr 7, 2020 |
| Publication date | Jul 9, 2024 |
| Grant date | Jul 9, 2024 |
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A method of producing fatty acid alkyl ester from an organic oil source containing at least one free fatty acid, wherein the vegetable and/or animal waste oil has an acid number of at least 30 mg KOH/g and wherein the method comprises the steps of a) reacting the oil source with glycerol at a temperature, which is at least 110° C. and does not exceed 180° C. during the reaction, in the presence of a catalyst comprising at least methane sulfonic acid or the homo anhydride thereof; and b) acidic transesterification at a temperature, which is at least 110° C. and does not exceed 160° C. during the reaction of the reaction product from step a) with an alkanol; and c) isolating the fatty acid alkyl ester from the reaction product of step b).
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The invention claimed is: 1. A method of producing fatty acid alkyl ester from an organic oil source comprising at least one free fatty acid, wherein the organic oil source has an acid number of at least 30 mg KOH/g and wherein the method comprises the steps of a) reacting the oil source with glycerol at a temperature, which is at least 110° C. and does not exceed 180° C. during the reaction, in the presence of a catalyst comprising at least methane sulfonic acid or the homo anhydride thereof; b) acidic transesterification at a temperature, which is at least 110° C. and does not exceed 160° C. during the reaction of the reaction product from step a) with an alkanol; and c) isolating the fatty acid alkyl ester from the reaction product of step b). 2. The method of claim 1 , wherein the fatty acid alkyl ester is fatty acid methyl ester. 3. The method of claim 1 , wherein the organic oil source is from used vegetable and/or animal oil and/or fat, by-products of the chemical and physical refining of vegetable and/or animal oil and/or fat, by-products of the refining of glycerol from biodiesel, fatty acids from distillation and non-distillation, trap grease, hydrolytically cleaved fatty substances distilled and non-distilled fatty acids resulting from the cleaving of soap or mixtures thereof. 4. The method of claim 1 , wherein the organic oil source has an acid number of at least 40 mg KOH/g oil source. 5. The method of claim 1 , wherein in step a) the temperature does not exceed 170° C. 6. The method of claim 1 , wherein in step a) the temperature is at least 120° C. 7. The method of claim 1 , wherein in step b) the temperature does not exceed 160° C. 8. The method of claim 1 , wherein in step b) the temperature is at least 115° C. 9. The method of claim 1 , wherein in step a) the initial molar ratio of glycerol to free fatty acid calculated on the basis of the acid number of the oil is from 1:2 to 1.2:1. 10. The method of claim 1 , wherein in step a), step b) or step a) and b) the amount of the methane sulfonic acid or anhydride thereof is from 0.5 to 1.5 weight-% based on the total amount of the oil source. 11. The method of claim 1 , wherein in step c) the isolation comprises a neutralization step. 12. The method of claim 1 , wherein in step c) the isolation comprises a distillation step. 13. The method of claim 12 , wherein the distillation in step c) is carried out under reduced pressure. 14. The method of claim 1 , wherein between step a) and step b) no phase separation is carried out. 15. The method of claim 1 , wherein step a) and step b) are carried out in the same reactor vessel. 16. The method of claim 1 , wherein after step b) and before step c) a step b′) of removing at least partly the alkanol by using the reaction temperature is introduced. 17. The method of claim 16 , wherein step b′) comprises lowering pressure of the reaction. 18. The method of claim 16 , wherein step b′) comprises lowering atmospheric pressure of the reaction.
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