Method of production of fatty acid alkyl esters and/or glycerine and fatty acid alkyl ester-containing composition

• US 7,605,281 B2
• Filed: 08/30/2004
• Issued: 10/20/2009
• Est. Priority Date: 08/29/2003
• Status: Expired due to Fees

• Current Assignee: Nippon Shokubai Company Limited
• Original Assignee: Nippon Shokubai Company Limited
• Inventors: Moriguchi, Toshimitsu, Oku, Tomoharu, Nonoguchi, Masanori
• Primary Examiner(s): Nazario-Gonzalez; Porfirio
• Assistant Examiner(s): Cutliff; Yate′ K
• Application Number:
  US10/569,979
• Publication Number:
  US 20070167642A1
• Time in Patent Office: 1,877 Days
• Field of Search: 554/30, 554/77, 554/165, 554/167, 554/169, 554/170
• US Class Current: 554/170
• CPC Class Codes: B01J 21/063 Titanium; Oxides or hydroxides thereof
• CPC Class Codes: B01J 21/066 Zirconium or hafnium; Oxides or hydroxides thereof
• CPC Class Codes: B01J 23/20 Vanadium, niobium or tantalum
• CPC Class Codes: B01J 23/22 Vanadium
• CPC Class Codes: B01J 23/8472 Vanadium
• CPC Class Codes: B01J 35/30 characterised by their physical properties
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

The method of producing fatty acid alkyl esters and/or glycerine of the present invention is a method of producing high-purity fatty acid alkyl esters and/or glycerine advantageously from the energy viewpoint while reducing the energy consumption of the production, and the products can be used in various fields of application, for example in biodiesel fuels, foods, cosmetics and pharmaceuticals.

The above-mentioned method of producing fatty acid alkyl esters and/or glycerine by reacting a fat or oil with an alcohol using an insoluble solid catalyst in a reaction apparatus comprising at least one reactor, comprises (a) a step of obtaining low-boiling components removed liquid by removing low-boiling components or fraction from an effluent liquid of a reactor and (b) a step of separating the fatty acid alkyl esters and glycerine from the low-boiling components removed liquid, wherein an eluted active metal component of the insoluble solid catalyst in the effluent liquid of a reactor amounts to a level not higher than 1,000 ppm.

Claims

1. A method of producing fatty acid alkyl esters and/or glycerine by reacting a fat or oil with an alcohol using an insoluble solid catalyst in a reaction apparatus comprising at least one reactor, comprising:

(a) obtaining low-boiling components removed liquid by removing low-boiling components or fraction from an effluent liquid of a reactor and

(b) separating the fatty acid alkyl esters and glycerine from the low-boiling components removed liquid,

wherein an eluted active metal component of the insoluble solid catalyst in the effluent liquid of a reactor amounts to a level not higher than 1,000 ppm;

wherein the insoluble solid catalyst comprises a mixed oxide catalyst, which contains;

as an essential component thereof, at least one metal element selected from the group consisting of the elements belonging to the Group 5 in the periodic table, and

as a second component thereof, at least one element selected from the elements belonging to the Group 3, 6, 8, 9, 10, 11, 12, 14, 15 and the Group 16 in the periodic table and lanthanoid.

2. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein obtaining the low-boiling components removed liquid by removing the low-boiling components or fraction from the effluent liquid of a last reactor is carried out in the absence of the catalyst.

3. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein separating the fatty acid alkyl esters and glycerine from the low-boiling components removed liquid comprises phase separation of the low-boiling components removed liquid into an ester phase and a glycerine phase.

4. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

which comprises reacting an ester phase separated from an effluent of a reactor with an alcohol in the next reactor in the presence of the insoluble solid catalyst.

5. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 3,

wherein the glycerine phase obtained in the phase separation of the low-boiling components removed liquid contains not less than 70 parts by weight of glycerine per 100 parts by weight of the glycerine phase.

6. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 3 comprising

purifying at least one of the ester phase and the glycerine phase obtained in the phase separation of the low-boiling components removed liquid by distillation,

wherein at least one of the purification residues is used as one of the raw materials for the reaction.

7. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein the alcohol is recovered from the low-boiling components or fraction distilled off and at least part of the recovered alcohol is used as a raw material.

8. method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein the insoluble solid catalyst is a catalyst capable of catalyzing the esterification of free fatty acids contained in the fat or oil.

9. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein a fixed bed reaction apparatus packed with the insoluble solid catalyst is used for a production and

the fatty acid alkyl esters and/or glycerine is produced continuously.

10. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 1,

wherein the insoluble solid catalyst comprises an oxide whose crystal is composed of an octahedral skeleton formed by coordination of the essential metal component with oxygen atoms in a six-coordinate complex-forming manner.

12. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 2,

wherein separating the fatty acid alkyl esters and glycerine from the low-boiling components removed liquid comprises phase separation of the low-boiling components removed liquid into an ester phase and a glycerine phase.

13. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 2,

which comprises reacting an ester phase separated from an effluent of a reactor with an alcohol in the next reactor in the presence of the insoluble solid catalyst.

14. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 2,

wherein the alcohol is recovered from the low-boiling components or fraction distilled off and at least part of the recovered alcohol is used as a raw material.

15. The method of producing the fatty acid alkyl esters and/or glycerine according to claim 2,

wherein a fixed bed reaction apparatus packed with the insoluble solid catalyst is used for a production and

the fatty acid alkyl esters and/or glycerine is produced continuously.

16. The method of producing the fatty acid alkyl esters

and/or glycerine according to claim 10,

wherein the octahedral skeleton comprises a layered oxide resulting from bonding of at least one pair of the octahedrons with at least one edge sharing.

17. The method of producing the fatty acid alkyl esters

and/or glycerine according to claim 10,

wherein the essential metal component is located at the center of each octahedron of the octahedral skeleton.

18. The method of producing the fatty acid alkyl esters

and/or glycerine according to claim 1,

wherein the mixed oxide catalyst is a crystallized form.

19. The method of producing the fatty acid alkyl esters

and/or glycerine according to claim 1,

wherein a ratio of the second component relative to the essential component is not less than 0.05 and not more than 10.

20. The method of producing the fatty acid alkyl esters

and/or glycerine according to claim 1,

wherein the mixed catalyst comprises at least one member selected from the group consisting of iron-vanadium mixed oxide, cobalt-vanadium mixed oxide, cerium-vanadium mixed oxide, molybdenum-niobium mixed oxide, molybdenum-tantalum mixed oxide, tungsten-niobium mixed oxide and tungsten-tantalum mixed oxide.

11. A method of producing the fatty acid alkyl esters and/or glycerine by reacting a fat or oil with an alcohol using an insoluble solid catalyst in a reaction apparatus comprising at least one reactor, comprising:

(a) obtaining low-boiling components removed liquid by removing low-boiling components or fraction from an effluent liquid of a reactor and

(b) separating the fatty acid alkyl esters and glycerine from the low-boiling components removed liquid,

wherein an eluted active metal component of the insoluble solid catalyst in the effluent liquid of a reactor amounts to a level not higher than 1,000 ppm;

wherein the insoluble solid catalyst comprises a layered compound represented by the following general formula (1);

ATi_XMO_(2X+3) 

 

(1)

wherein A represents a hydrogen atom or an alkali metal atom, M represents a niobium atom or a tantalum atom and X is a natural number not greater than 7.