Method for removing monoisocyanates from organic solution

Patent metadata

Field	Value
Publication number	US-12071394-B2
Application number	US-201917288967-A
Country	US
Kind code	B2
Filing date	Jul 31, 2019
Priority date	Oct 31, 2018
Publication date	Aug 27, 2024
Grant date	Aug 27, 2024

Abstract

Monoisocyanate impurities are removed from a process stream obtained when solvent is separated from a polyisocyanate product. The monoisocyanates are reacted with amine compounds at specific molar ratios to produce ureas. The ureas can be discarded by burning, landfilling or otherwise. Alternatively the ureas can be recycled back into the polyisocyanate manufacturing process, where they are formed into biuret compounds that can remain with the polyisocyanate product.

First claim

What is claimed is:

1. A method for removing phenyl isocyanate from an organic solvent, comprising the steps of:
a) contacting i) a starting solution containing at least 85 weight percent, based on the weight of the starting solution, of one or more organic solvents inert to reaction with isocyanate and amine groups and 1.5 to 15 weight percent, based on the weight of the starting solution, of phenyl isocyanate, with ii) at least one amine selected from the group consisting of aniline, MDA and PMDA, in proportions sufficient to provide 0.01 to 0.8 equivalents of primary and/or secondary amino groups per equivalent of isocyanate groups in the starting solution; and
b) reacting at least a portion of the phenyl isocyanate with at least a portion of the amine to form a slurry of the one or more urea compounds in the one or more organic solvents.

2. The method of claim 1 wherein the starting solution and amine are combined in proportions sufficient to provide 0.2 to 0.75 equivalents of primary and/or secondary amino groups per equivalent of isocyanate groups in the starting solution.

3. The method of claim 1 wherein step a) is performed by adding the amine to the starting solution in two or more increments or continuously.

4. The method of claim 1 further comprising a step of reacting at least a portion of the one or more urea compounds with a polyisocyanate to form one or more biuret compounds.

5. The method of claim 1 , further comprising recycling at least a portion of the one or more urea compounds into an MDI and/or polymeric MDI manufacturing process, which MDI and/or polymeric MDI manufacturing process comprises a step of reacting a polyamine with phosgene in solution in a process solvent to produce an MDI and/or polymeric MDI product and a step of separating the MDI and/or polymeric MDI product from the process solvent, wherein the recycling of at least a portion of the one or more urea compounds into the MDI and/or polymeric MDI manufacturing process is performed downstream of the step of reacting the polyamine with phosgene in the process solvent, and the one or more urea compounds react with a portion of the polyisocyanate product to form one or more biuret compounds during the step of separating the MDI and/or polymeric MDI product from the process solvent.

6. The method of claim 1 further comprising the step of c) separating at least a portion of the one or more organic solvents from the one or more urea compounds.

7. The method of claim 1 wherein the amine is aniline.

8. An MDI and/or polymeric MDI manufacturing process, comprising the steps of:
a) reacting aniline with formaldehyde in a solvent to produce a mixture of MDA, PMDA and unreacted aniline in the solvent;
b) distilling aniline from the mixture produced in step a) to produce a process stream containing the solvent, MDA, PMDA and residual aniline;
c) phosgenating the process stream from step b) to form an isocyanate process stream containing the solvent, MDI, one or more polymethylene polyphenylisocyanates that have at least three phenyl isocyanate groups and phenyl isocyanate;
d) separating MDI and polymethylene polyphenylisocyanates that have at least three phenyl isocyanate groups and phenyl isocyanate from the isocyanate process stream obtained in step c) by distillation to produce a solvent stream containing at least a portion of the solvent, 0.2 to 10 weight percent phenyl isocyanate based on the weight of the solvent stream and 0.0001 to 5 weight percent, based on the weight of the solvent stream, of MDI and/or one or more polymethylene polyphenylisocyanates that have at least three phenyl isocyanate groups;
e) combining the solvent stream obtained in step d) with aniline at a ratio of 0.01 to 0.8 moles of aniline per mole of phenyl isocyanate and reacting at least a portion of the aniline with phenyl isocyanate to form urea compounds;
f) recycling the urea compounds and optionally the solvent in the solvent stream into the manufacturing process downstream from step c) and into step d), whereby at least a portion of the urea compounds react during step d) with at least a portion of the MDI and/or one or more polymethylene polyphenylisocyanates that have at least three phenyl isocyanate groups to form biuret compounds.

9. The manufacturing process of claim 8 wherein step e) is performed by adding the aniline to the solvent stream obtained in step d) in two or more increments or continuously at a temperature of at least 80° C.

Assignees

• Dow Global Technologies Llc
• Dow Portugal Produtos Quimicos Soc Unipessoal Lda
• Dow Portugal Produtos Quimicos Soc Unipessoal

Inventors

• Hefner Jr Robert E
• Braun Helge
• Costa Armenio
• Cramm Brian

Classifications

• C08G18/7664

  containing alkylene polyphenyl groups · CPC title

• C07C273/1881 Primary

  from urea · CPC title

• C07C273/1827

  X being H · CPC title

• C07C263/10 Primary

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C273/1818

  from -N=C=O and XNR'R" · CPC title