CA2556586A1 - Thiol ester compositions and processes for making and using same - Google Patents

Thiol ester compositions and processes for making and using same Download PDF

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Publication number
CA2556586A1
CA2556586A1 CA002556586A CA2556586A CA2556586A1 CA 2556586 A1 CA2556586 A1 CA 2556586A1 CA 002556586 A CA002556586 A CA 002556586A CA 2556586 A CA2556586 A CA 2556586A CA 2556586 A1 CA2556586 A1 CA 2556586A1
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CA
Canada
Prior art keywords
thiol ester
thiol
composition
ester
average
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CA002556586A
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French (fr)
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CA2556586C (en
Inventor
Mitchell D. Refvik
Daniel M. Hasenberg
Chad W. Brown
Michael S. Matson
Jim D. Byers
Dale M. Solaas
Michael S. Hankinson
Steven J. Herron
Leslie L. Carstens
Baozhong Xing
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Nutrien Canada Holdings ULC
Chevron Phillips Chemical Co LP
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Individual
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C9/00—Fertilisers containing urea or urea compounds
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G5/00—Fertilisers characterised by their form
    • C05G5/30—Layered or coated, e.g. dust-preventing coatings
    • C05G5/36—Layered or coated, e.g. dust-preventing coatings layered or coated with sulfur
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G5/00—Fertilisers characterised by their form
    • C05G5/30—Layered or coated, e.g. dust-preventing coatings
    • C05G5/37—Layered or coated, e.g. dust-preventing coatings layered or coated with a polymer
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/26—Polythioesters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom

Abstract

Thiol ester compositions, methods of making the thiol ester compositions, and methods of using the thiol ester compositions are provided. In some embodiments, the thiol ester compositions include thiol esters, hydroxy thiol esters and cross-linked thiol esters. The thiol ester composition can be used to produce cross-linked thiol esters, sulfonic acid-containing esters, sulfonate containing esters and thiocrylates containing esters. The thiol ester composition can be used to produce polythiourethanes. The polythiourethanes can be used in fertilizers and fertilizer coatings.

Claims (82)

1. A thiol ester composition comprising thiol ester molecules having an average of at least 1.5 ester groups per thiol ester molecule, having an average of at least 1.5 thiol groups per thiol ester molecule, and having a molar ratio of cyclic sulfides to thiol groups of less than 1.5.
2. The thiol ester composition of claim 1, wherein the thiol ester molecules have a molar ratio of cyclic sulfides to thiol groups ranging from 0 to 1Ø
3. The thiol ester composition of claim 1, wherein the thiol ester molecules have an average ranging from 1.5 to 9 thiol groups per thiol ester molecule.
4. The thiol ester composition of claim 1, wherein the thiol ester molecules have a molar ratio of carbon-carbon double bonds to thiol groups of less than 1.5.
5. The thiol ester composition of claim 1, wherein the thiol ester molecules have an average of greater than 2 weight percent thiol sulfur.
6. The thiol ester composition of claim 1, wherein thiol ester molecules have an average ranging from 8 to 10 weight percent thiol sulfur.
7. The thiol ester composition of claim 1, wherein the thiol ester molecules have an average of less than 30 mole percent total sulfur present as cyclic sulfides.
8. The thiol ester composition of claim 1, wherein the thiol ester molecules have an average of less than 10 mole percent total sulfur present as cyclic sulfides.
9. The thiol ester composition of claim 1, wherein greater than 40 percent of thiol ester molecule total side chains contain sulfur.
10. A process for producing a thiol ester composition comprising the steps of:

a) contacting hydrogen sulfide and an unsaturated ester composition comprising unsaturated esters having an average of at least 1.5 ester groups per unsaturated ester molecule and having an average of at least 1.5 carbon-carbon double bonds per unsaturated ester molecule; and b) reacting the hydrogen sulfide and the unsaturated esters to form a thiol ester composition comprising thiol ester molecules having a molar ratio of cyclic sulfides to thiol groups of less than 1.5.
11. The process of claim 10, wherein the unsaturated ester composition comprises a natural source oil.
12. The process of claim 10, wherein the unsaturated ester composition comprises soybean oil.
13. The process of claim 10, wherein reacting the hydrogen sulfide and the unsaturated esters occurs in the presence of a solvent.
14. The process of claim 10, wherein the step of reacting the hydrogen sulfide and the unsaturated esters occurs in substantial absence of a solvent.
15. The process of claim 10, wherein the thiol ester molecules have a molar ratio of the hydrogen sulfide to carbon-carbon double bonds of greater than 2.
16. The process of claim 10, wherein the step of reacting the hydrogen sulfide and the unsaturated esters is catalyzed by a heterogeneous catalyst or a homogeneous catalyst.
17. The process of claim 10, wherein the step of reacting the hydrogen sulfide and the unsaturated esters is initiated by a free-radical initiator or LTV radiation.
18. The process of claim 10, wherein the thiol ester molecules have an average of greater than 5 weight percent thiol sulfur.
19. The process of claim 10, wherein reacting the hydrogen sulfide and the unsaturated esters occurs at a temperature of greater than-20°C.
20. The process of claim 10, wherein greater than 40 percent of the thiol ester molecule total side chains contain sulfur.
21. The process of claim 10, wherein the process is a continuous process and the reaction of the hydrogen sulfide and the unsaturated esters is performed in an absence of a solvent, at a temperature of greater than -20°C, and is initiated by UV
radiation.
22. A process for producing a thiol ester composition comprising the steps of a) contacting hydrogen sulfide and an unsaturated ester composition comprising unsaturated esters having an average of at least 1.5 ester groups per unsaturated ester molecule and having an average of at least 1.5 carbon-carbon double bonds per unsaturated ester molecule; and b) reacting the hydrogen sulfide and the unsaturated esters in a substantial absence of a solvent to form the thiol ester composition comprising thiol ester molecules.
23. The process of claim 22, wherein the unsaturated ester composition comprises a natural source oil.
24. The process of claim 22, wherein the unsaturated esters composition comprises soybean oil.
25. The process of claim 22, wherein the thiol ester molecules have a molar ratio of cyclic sulfides to thiol groups of less than 1.5.
26. The process of claim 22, wherein the thiol ester molecules have a molar ratio of the hydrogen sulfide to carbon-carbon double bonds is greater than 1.
27. The process of claim 22, wherein the reaction of the hydrogen sulfide and the unsaturated esters is catalyzed by a heterogeneous catalyst or a homogeneous catalyst.
28. The process of claim 22, wherein the reaction of the hydrogen sulfide and the unsaturated esters is initiated by a free-radical initiator or UV radiation.
29. The process of claim 22, wherein the thiol ester molecules have an average of greater than 5 weight percent thiol sulfur.
30. The process of claim 22, wherein reacting the hydrogen sulfide and the unsaturated esters occurs at a temperature of greater than-20°C.
31. The process of claim 22, wherein greater than 40 percent of the thiol ester molecule total side chains contain sulfur.
32. A process for preparing a thiol ester composition comprising:

a) ~contacting a polyol composition and a thiol carboxylic acid composition;
and b) ~reacting the polyol composition and the thiol carboxylic acid composition to produce the thiol ester composition comprising thiol ester molecules having an average of at least 1.5 ester groups per thiol ester molecule and having an average of at least 1.5 thiol groups per thiol ester molecule.
33. A hydroxy thiol ester composition comprising hydroxy thiol ester molecules having an average of at least 1 ester groups per hydroxy thiol ester molecule and having an average of at least 1 .alpha.-hydroxy thiol groups per hydroxy thiol ester molecule.
34. The composition of claim 33, wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 .alpha.-hydroxy thiol groups per hydroxy thiol ester molecule.
35. The composition of claim 33, wherein the hydroxy thiol ester molecules have an average of greater than 2.5 weight percent thiol sulfur.
36. The composition of claim 33, wherein the hydroxy thiol ester molecules have an average ranging from 8 to 10 weight percent thiol sulfur.
37. The composition of claim 33 , wherein the hydroxy thiol ester molecules have a molar ratio of epoxide groups to the .alpha.-hydroxy thiol groups of less than 2.
38. The composition of claim 33, wherein greater than 40 percent of the hydroxy thiol ester molecule total side chains contain sulfur.
39. The composition of claim 33, wherein the composition is substantially free of epoxide groups.
40. A hydroxy thiol ester composition comprising hydroxy thiol ester molecules having an average of at least 1 ester groups per hydroxy thiol ester molecule, having an average of at least 1 thiol groups per hydroxy thiol ester molecule, and having an average of at least 1 alcohol groups per hydroxy thiol ester molecule.
41. The composition of claim 40, wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 thiol groups per hydroxy thiol ester molecule.
42. The composition of claim 40, wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 alcohol groups per hydroxy thiol ester molecule.
43. The composition of claim 40, wherein the hydroxy thiol ester molecules have an average of greater than 2.5 weight percent thiol sulfur.
44. The composition of claim 40, wherein the hydroxy thiol ester molecules have an average ranging from 8 to 10 weight percent thiol sulfur.
45. The composition of claim 40, wherein the hydroxy thiol ester molecules have a molar ratio of epoxide groups to thiol groups of less than 2.
46. The composition of claim 40, wherein greater than 40 percent of the hydroxy thiol ester molecule total side chains contain sulfur.
47. The composition of claim 40, wherein the composition is substantially free of epoxide groups.
48. A process for preparing a hydroxy thiol ester composition, comprising the steps of:

a) contacting hydrogen sulfide and an epoxidized unsaturated ester composition comprising epoxidized unsaturated esters having an average of at least 1 ester groups per epoxidized unsaturated ester molecule and having an average of at least 1 epoxide groups per epoxidized unsaturated ester molecule; and b) reacting the hydrogen sulfide and the epoxidized unsaturated esters to form the hydroxy thiol ester composition.
49. The process of claim 48, wherein the epoxidized unsaturated ester composition comprises an epoxidized natural source oil.
50. The process of claim 48, wherein the epoxidized unsaturated ester composition comprises an epoxidized soybean oil.
51. The process of claim 48, wherein a molar ratio of the hydrogen sulfide to epoxide groups in the epoxidized unsaturated esters is greater than 1.
52. The process of claim 48, wherein reacting the hydrogen sulfide and the epoxidized unsaturated esters is performed in the presence of a catalyst.
53. The process of claim 48, wherein the hydroxy thiol ester composition comprises hydroxy thiol ester molecules having an average of greater than 2.5 weight percent thiol sulfur.
54. The process of claim 48, wherein the hydroxy thiol ester composition comprises hydroxy thiol ester molecules having an average ranging from 8 to 10 weight percent thiol sulfur.
55. The process of claim 48, wherein the hydroxy thiol ester composition comprises hydroxy thiol ester molecules having greater than 40 percent of the hydroxy thiol ester molecule total side chains contain sulfur.
56. A process for preparing a hydroxy thiol ester composition comprising the steps of:

a) contacting a polyol composition and a hydroxy thiol carboxylic acid composition; and b) reacting the polyol composition and the hydroxy thiol carboxylic acid composition to produce the hydroxy thiol ester composition comprising hydroxy thiol ester molecules having an average of at least 1 ester groups per hydroxy thiol ester molecule and having an average of at least 1 .alpha.-hydroxy thiol groups per hydroxy thiol ester molecule.
57. A cross-linked thiol ester composition comprising thiol ester oligomers having at least two thiol ester monomers connected by a polysulfide linkage having a structure -S Q-, wherein Q is greater than 1.
58. The cross-linked thiol ester composition of claim 57, wherein the thiol ester oligomers have at least three thiol ester monomers connected by polysulfide linkages.
59. The cross-linked thiol ester composition of claim 57, wherein the thiol ester oligomers have from 3 to 20 thiol ester monomers connected by polysulfide linkages.
60. The cross-linked thiol ester composition of claim 57, wherein the crosslinked thiol ester composition comprises thiol ester monomers and thiol ester oligomers.
61. The cross-linked thiol ester composition of claim 60, wherein the thiol ester monomers and thiol ester oligomers have a total thiol sulfur content from 0.5 to 8 weight percent.

176~
62. The cross-linked thiol ester composition of claim 60, wherein the combined thiol ester monomers and thiol ester oligomers have an average molecular weight greater than 2000.
63. The cross-linked thiol ester composition of claim 60, wherein the thiol ester monomers and thiol ester oligomers have an average molecular weight from 2000 to 20,000.
64. The cross-linked thiol ester composition of claim 60, wherein the thiol ester monomers and thiol ester oligomers have a total sulfur content ranging from 8 to 15 weight percent.
65. A cross-linked thiol ester composition produced by the process comprising the steps of:

a) ~contacting a thiol ester composition with an oxidizing agent; and b) ~reacting the thiol ester and the oxidizing agent to form thiol ester oligomers having at least two thiol ester monomers connected by a polysulfide linkage having a structure -S Q-, wherein Q is greater than 1.
66. A process to produce a cross-linked thiol ester composition comprising:

a) ~contacting a thiol ester composition with an oxidizing agent; and b) ~reacting the thiol ester and the oxidizing agent to form thiol ester oligomers having at least two thiol ester monomers connected by a polysulfide linkage having a structure -S Q-, wherein Q is greater than 1.
67. The process of claim 66, wherein the oxidizing agent is elemental sulfur, oxygen, or hydrogen peroxide.
68. The process of claim 66, wherein the oxidizing agent is elemental sulfur.
69. The process of claim 66, wherein the thiol ester is a hydroxy thiol ester.
70. The process of claim 66, wherein a weight ratio of elemental sulfur to thiol sulfur in the thiol ester molecules ranges from 0.5 to 32.
71. The process of claim 66, wherein step of the reacting the thiol ester and the oxidizing agent is performed at a temperature ranging from 25 °C to 150 °C.
72. The process of claim 66, wherein residual hydrogen sulfide is stripped from the cross-linked thiol ester composition produced.
73. The process of claim 68, wherein the reaction of the thiol ester and the elemental sulfur is catalyzed.
74. The process of claim 73, wherein the catalyst is an amine.
75. A method of making a catalyst composition for use in oligomerizing an olefin comprising a chromium-containing compound the method comprising abating all or a portion of water, acid protons, or both from a composition comprising the chromium-containing compound.
76. The method of claim 75, wherein the chromium-containing compound is contacted with a non-halide metal alkyl.
77. The method of claim 76, wherein the non-halide metal alkyl is triethylaluminum.
78. The method of claim 75, wherein the chromium-containing compound is contacted with a solvent to form a solution and the solution is subjected to azeotropic distillation.
79. The method of claim 78, wherein the solvent comprises an aromatic compound, a halogenated compound, a paraffin, or combinations thereof.
80. The method of claim 78, wherein the solvent is an aromatic compound comprising benzene, toluene, ethylbenzene, mixed xylenes, ortho-xylene, meta-xylene, para-xylene, or combinations thereof.
81. The method of claim 75, wherein the chromium-containing compound is contacted with an absorbent to remove water.
82. The method of claim 81, where the absorbent comprises 3-Angstrom molecular sieves, 5-Angstrom molecular sieves, alumina, silica, or combinations thereof.
CA2556586A 2004-02-17 2005-02-17 Thiol ester compositions and processes for making and using same Expired - Fee Related CA2556586C (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US54526004P 2004-02-17 2004-02-17
US60/545,260 2004-02-17
US56168504P 2004-04-13 2004-04-13
US56185504P 2004-04-13 2004-04-13
US56161404P 2004-04-13 2004-04-13
US60/561,685 2004-04-13
US60/561,614 2004-04-13
US60/561,855 2004-04-13
PCT/US2005/005110 WO2005080325A2 (en) 2004-02-17 2005-02-17 Sulfur-containing compositions and processes for making same

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CA2556586A1 true CA2556586A1 (en) 2005-09-01
CA2556586C CA2556586C (en) 2012-09-11

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US (4) US7557236B2 (en)
EP (1) EP1723104B1 (en)
JP (1) JP2007526939A (en)
CN (1) CN102408366B (en)
AT (1) ATE487696T1 (en)
AU (1) AU2005214369A1 (en)
BR (1) BRPI0507783A (en)
CA (1) CA2556586C (en)
DE (1) DE602005024664D1 (en)
EA (1) EA200601518A1 (en)
MX (1) MXPA06009333A (en)
NZ (1) NZ549073A (en)
PL (1) PL1723104T3 (en)
WO (1) WO2005080325A2 (en)

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