IP Library Granted Patent US 7,205,423
Granted Patent B1
US 7,205,423 · App. 11/385,291 · Granted Apr 17, 2007

Process for the preparation of organo-molybdenum compounds

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Quick Facts
Patent No.
US 7,205,423
App. No.
11/385,291
Granted
Apr 17, 2007
Kind
B1
Abstract

This invention is a process for preparation of 2,4-heteroatom-substituted molybdena-3,3-dioxocycloalkane compounds by reacting diol-, diamino, thiol-alcohol- and amino-alcohol-compounds with the following reagents: ammonium molybdate (or in situ produced ammonium molybdate by the reaction of ammonia with molybdenum trioxide or molybdic acid) as a molybdenum source, ammonia as an additional or secondary reagent or promoter, in molar ratio NH 3 :Mo (amount of molybdenum in the molybdenum source) of ≧1:1, preferably 1–3:1, more preferably 2–3:1, and most preferred 2.2–2.65:1.

Claims (27)

1. A process for preparing 2,4-heteroatom-substituted molybdena-3,3-dioxocycloalkane compounds, comprising the steps of:

reacting (A) a starting material having the structural formula

wherein X 1 and X 2 are selected from the group consisting of O, S or N and where n or m=1 when X 1 or X 2 is O or S and n or m=2 when X 1 or X 2 is N, y=0 or 1, and wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, alkylaryl hydrocarbon group or fatty residue containing from 1 to 50 carbon atoms or polymeric residues having a molecular weight of 150 to 1200; and selected from poly-alpha-olefin, polypropene, polybutylene and polyisobutylene; with:

(B) ammonium molybdate as a molybdenum source sufficient to yield about 2 to 20 percent of molybdenum based on the weight of the molybdena-compound, in the presence of water, and

(C) an additional or secondary reagent or promoter in molar amount≧1:1, Z:Mo, where Z is one of or both in combination of (i) ammonia and (ii) an alkylamine where the alkyl groups are independently selected from straight or branched chain C1 to C6;

removing water; and

recovering the molybdena-compounds.

2. The process of claim 1 , wherein the recovered molybdena compounds comprise a complex mixture represented by a generic formula as

and which may optionally also contain oligomers and polymer due to the multifunctional nature of the reagents,

wherein R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , n and m are defined and correspond to the starting materials in formula (I) and (II).

3. The process according to claim 1 , further comprising adding as an additional reagent up to 20% of a phase transfer agent of the formula

wherein R 6 is an alkyl group or fatty residue having 8 to 22 carbon atoms and X 3 is a hydroxy or amino group.

4. The process according to claim 3 , wherein the phase transfer agent is added in an amount up to 8%.

5. The process according to claim 1 , further comprising adding as an additional reagent hydrogen peroxide from 1 to 5 percent of 35% hydrogen peroxide or the equivalent thereof.

6. The process according to claim 4 , wherein the phase transfer agent is 1-(2-hydroxyethyl)-2-octadecylimidazoline.

7. The process according to claim 1 , wherein the starting material of formula I is derived from epoxidized fatty oils or fatty acids.

8. The process according to claim 1 wherein the starting material of formula I is derived from triglycerides.

9. The process according to claim 1 , wherein the starting material of formula I is derived from epoxidized polymers having a molecular weight in the range of 150 to 1200 and selected from poly-alpha-olefins, polypropene, polybutylene and polyisobutylene.

10. The process according to claim 1 , wherein the ammonium molybdate is produced in situ from molybdenum trioxide or molybdic acid and ammonia.

11. A process according to claim 1 , wherein the reaction ratio is 1–3:1, and which further comprises a filtration step where the ratio is at a level less than 2.06:1.

12. The process according to claim 4 , wherein R6 is derived from tall oil (50:50 oleic:linoleic acid).

13. The process according to claim 12 , wherein the imidazoline derivative is 1-(2-hydroxyethyl)-2-imidazoline derived from 50:50 oleic:linoleic acid in an amount of 6 to 8 percent by mass.

14. The process of claim 1 , wherein the reaction ratio is 1–3:1.

15. The process of claim 14 , wherein the reaction ratio is 2.07–2.95.

16. The process of claim 15 , wherein the reaction ratio is 2.2–2.65:1.

17. The process of claim 14 , wherein Z is ammonia.

18. The process of claim 1 , wherein the reaction takes place at 60 to 150° C.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2013
From: VANDERBILT MINERALS, LLC
To: VANDERBILT CHEMICALS, LLC
Reel/Frame 029667/0105 →
MERGER Recorded Jan 17, 2013
From: R.T. VANDERBILT COMPANY, INC.
To: VANDERBILT MINERALS, LLC
Reel/Frame 029647/0256 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2006
From: GERSHON, DANIEL; ENSOR, SHAUN JEREMY; ST. PIERRE, MICHAEL JAMES
To: R.T. VANDERBILT COMPANY, INC.
Reel/Frame 018059/0197 →