Production and composition of glycerol based polyols

Patent metadata

Field	Value
Publication number	US-9290620-B2
Application number	US-58282709-A
Country	US
Kind code	B2
Filing date	Oct 21, 2009
Priority date	Oct 21, 2009
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

The invention provides a method of efficiently producing branched, cyclic glycerol-based polyols with a co-product as anti-biodegrading agent from inexpensive readily available glycerol monomer. The method involves polymerizing glycerol or glycerol with at least another monomer to multiple other monomers in the presence of particular amount of a strong base as the catalyst under a particular distillation environment. The polyol produced by the inventive method is beneficial of reducing scales in Bayer liquid for aluminum production process and improving brightness of coated paper substrates without greening effect.

First claim

What is claimed is:

1. A method of synthesizing glycerol-based polyol products comprising the step of:
reacting a reaction mass comprising at least glycerol monomer in the presence of a strong base catalyst of a concentration of above 2%, in a low reactivity atmospheric environment at a temperature above 200 degrees C. which produces a product comprising branched, cyclic polyols and a co-product comprising lactic acid, lactic salt, and any combination thereof and the co-product is in such a concentration that the polyol product is resistant to biological contamination for at least two years after synthesis, wherein the low reactivity atmospheric environment is a flow of an inert gas and the flow is at a rate of 0.93 to 3.72 mol of inert gas per hour per mol of monomer(s).

2. The method of claim 1 further comprising the steps of providing a catalyst above 3%.

3. The method of claim 2 in which the catalyst is selected from the group consisting of: NaOH, KOH, CsOH, a base stronger than NaOH, and any combination thereof.

4. The method of claim 1 in which the atmospheric environment is an atmospheric pressure of less than 760 mm Hg.

5. The method of claim 1 in which the glycerol-based polyol products are selected from the group consisting of polyglycerols, polyglycerol derivatives, a polyol having both glycerol monomer units and non-glycerol monomer units and any combination thereof the polyols have at least two hydroxyl groups.

6. The method of claim 1 in which at least a portion of the produced polyols have both at least a 0.1 degree of branching and at least a 0.01 degree of cyclization.

7. The method of claim 1 in which the co-product is at least 1% by weight.

8. The method of claim 1 in which the glycerol-based polyol products are at least 166 Daltons in molecular weight.

9. The method of claim 1 in which the glycerol-based polyol products have a polydispersity of at least 1.

10. The method of claim 1 in which the glycerol is pure, technical, crude, or any combination thereof.

11. The method of claim 1 further comprising other monomers selected from the group consisting of polyols and amines.

12. The method of claim 1 further comprising the steps of pre-determining the desired molecular weight of the produced polyglycerol and adjusting the atmospheric environment to match the environment optimum for producing the desired molecular weight.

13. The method of claim 1 further comprising the steps of pre-determining the desired degree of branching and the desired degree of cyclization of the produced polyglycerol and the desired amount of co-product, and adjusting the atmospheric environment to match the environment optimum for producing the desired degree of branching, degree of cyclization and amount of co-product lactic acid and/or lactate salt.

14. The method of claim 1 in which the branched, cyclic polyols are in molecular weight range of 2,240 to 150,000 Daltons and have a polydispersity range of 1 to 30.

15. The method of claim 1 in which the resulting polymer undergoes such an exothermic reaction that it becomes so crosslinked as to have a degree of branching greater than 0.2.

16. The method of claim 1 in which the resulting polymer is so crosslinked as to have a degree of branching greater than 0.2.

17. A method of synthesizing glycerol-based polyol products comprising the step of:
reacting a reaction mass comprising at least glycerol monomer in the presence of a strong base catalyst of a concentration of above 2%, in a low reactivity atmospheric environment at a temperature above 200 degrees C. which produces a reaction product comprising a polyol having a degree of branching greater than 0.2 and a co-product comprising lactic acid, lactic salt, and any combination thereof and the co-product is in such a concentration that the reaction product is resistant to biological contamination for at least two years after synthesis, wherein the low reactivity atmospheric environment is a flow of an inert gas and the flow is at a rate of 0.19 0.93 to 3.72 mol of inert gas per hour per mol of monomer(s).

18. A method of synthesizing glycerol-based polyol products comprising the step of:
reacting a reaction mass of glycerol monomer in the presence of a strong base catalyst of a concentration of above 2%, in a low reactivity atmospheric environment at a temperature above 200 degrees C. which produces a polyglycerol product comprising branched, cyclic polyols and a co-product comprising lactic acid, lactic salt, and any combination thereof and the co-product is in such a concentration that the polyol product is resistant to biological contamination for at least two years after synthesis, wherein the low reactivity atmospheric environment is a flow of an inert gas and the flow is at a rate of 0.93 to 3.72 mol of inert gas per hour per mol of monomer(s).

19. The method of claim 1 , wherein the lactic acid is present in an amount from 11% to 22% by weight of the reaction product.

Assignees

• Li Xiaojin Harry
• Shih Joanna L
• Bode Heinrich E
• Wang Jing
• Swiecinski Frederick J
• Nalco Co

Inventors

• Li Xiaojin Harry
• Shih Joanna L
• Bode Heinrich E
• Wang Jing
• Swiecinski Frederick J

Classifications

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C07C41/09

  by dehydration of compounds containing hydroxy groups · CPC title

• C07C51/41

  Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D) · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title

• C08G65/26

  from cyclic ethers and other compounds · CPC title