Method for preparing high-quality lubricant from biomass-derived fatty acid

Patent metadata

Field	Value
Publication number	US-9976098-B2
Application number	US-201414782957-A
Country	US
Kind code	B2
Filing date	Apr 8, 2014
Priority date	Apr 9, 2013
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Disclosed is a method for producing a quality lubricant base oil (meeting the standard of Group III or higher) comprising: decarbonylating mixed fatty acids derived from oils and fats of biological origin to produce mixed olefins; oligomerizing the mixed olefins to produce an olefinic lubricant base oil; and performing hydrogenation to remove olefins from the olefinic lubricant base oil.

First claim

The invention claimed is:

1. A method for producing a lubricant base oil from a biomass-derived fatty acid, comprising:
a) providing biomass-derived mixed fatty acids;
b) decarbonylating the mixed fatty acids to produce mixed olefins, wherein a double bond is formed at an alpha position in the mixed olefins, and the double bond is shifted toward the center of carbon chains to produce internal olefins;
c) oligomerizing the mixed olefins to produce an olefinic lubricant base oil; and
d) performing hydrogenation to remove olefins in the olefinic lubricant base oil,
wherein the step b) is carried out in presence of a transition metal-chelate catalyst, the transition metal being one or more selected from transition metals in Groups 8 to 10 on Periodic Table, a chelator being a phosphine ligand,
wherein the transition metal-chelate catalyst contains triphenylphosphine or diphenyl phosphine-C 4˜7 paraffin as a chelator, and further either or both of CO and halogen as a ligand, and an acid anhydride is introduced to a reaction system during the decarbonylation under a CO or N 2 atmosphere,
wherein olefins in the mixed olefins of step b) are fewer by one in the number of carbon atoms than corresponding fatty acids in the mixed fatty acids of step a).

2. The method of claim 1 , wherein carbon atoms of the mixed fatty acids of step a) range from 4 to 24.

3. The method of claim 2 , wherein the mixed fatty acids contain a fatty acid of 16 carbon atoms, a fatty acid of 18 carbon atoms, or a combination thereof in an amount of at least 80% by weight.

4. The method of claim 1 , wherein the mixed fatty acids of step a) are fatty acids derived from triglyceride of biomass by de-esterification, fatty acids contained in biomass itself, or a combination thereof.

5. The method of claim 1 , wherein the mixed fatty acids have a double bond content of 60% or less of a total carbon bonds thereof.

6. The method of claim 1 , wherein the step a) further comprises a pre-hydrotreatment (pre-HDT) step in which at least a part of double bonds of the mixed fatty acids is removed by saturation.

7. The method of claim 2 , wherein the mixed fatty acids are fatty acid distillates separated from biomass.

8. The method of claim 1 , wherein the decarbonylation is carried out at a temperature of 120 to 400° C. under a pressure of 50 bar or less.

9. The method of claim 1 , wherein the oligomerization is carried out in presence of a cationic polymerization catalyst, the cationic polymerization catalyst being zeolite, clay, SAPO, AlPO, or aluminum (A)-supported mesoporous silica.

10. The method of claim 9 , wherein the cationic polymerization catalyst is montmorillonite, Y-zeolite having a SAR of 30 to 150, an RFCC catalyst, or beta-zeolite.

11. The method of claim 9 , a product of the oligomerization has a weight ratio of dimer/trimer or higher of 0.1˜100, and a chain length of 15 to 33 carbon atoms.

12. The method of claim 9 , wherein the oligomerization is carried out at a temperature of 120 to 400° C.

13. The method of claim 1 , wherein the hydrogenation is carried out at a reaction temperature of 150 to 500° C. and at a GOR (H 2 /feed ratio) of 300 to 2000 Nm 3 /m 3 under a H 2 pressure of 5 to 200 ba.

14. The method of claim 1 , wherein the lubricant base oil meets a Group III+ standard.

15. The method of claim 14 , wherein the lubricant base oil has a viscosity index of at least 118, a pour point of −40° C. or less, and a cloud point of −40° C. or less.

16. The method of claim 1 , wherein the biomass is animal biomass, vegetable biomass, or a combination thereof, the animal biomass being fish oil, beef tallow, lard, sheep tallow, or butter, the vegetable biomass being sunflower seed oil, canola oil, palm oil, corn oil, cotton seed oil, rapeseed oil, linseed oil, safflower seed oil, oat oil, olive oil, palm oil, peanut oil, apricot seed oil, almond oil, avocado oil, olive oil, camellia oil, rice bran oil, cotton seed oil, peanut oil, walnut oil, rapeseed oil, rice bran oil, linseed oil, sesame oil, soybean oil, castor oil, cocoa butter, or palm kernel oil.

Assignees

• Sk Innovation Co Ltd
• Sk Lubricants Co Ltd

Inventors

• Jeon Hee Jung
• Yang Ja Hyun
• Kim Tae Jin
• Lee Young Hwan
• Lee Jong Chan
• Kwon Wan Seop
• Ok Jin Hee

Classifications

• B01J2531/842

  Iron · CPC title

• B01J31/2404

  Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring · CPC title

• C10M177/00

  Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes · CPC title

• C10N2020/02

  Viscosity; Viscosity index · CPC title

• B01J2231/12

  Olefin polymerisation or copolymerisation · CPC title