Process for reducing impurity levels in methylene diphenyamines

• US 5,286,760 A
• Filed: 10/09/1992
• Issued: 02/15/1994
• Est. Priority Date: 10/09/1992
• Status: Expired due to Fees

• Current Assignee: Miles, Inc. (Bayer AG)
• Original Assignee: Miles, Inc. (Bayer AG)
• Inventors: Mayen, Robert L., Bolton, Jeffrey S.
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US07/959,233
• Time in Patent Office: 494 Days
• Field of Search: 564/330, 564/331, 564/332, 564/333, 564/334, 560/347, 560/358, 521/185, 521/160
• US Class Current: 521/160
• CPC Class Codes: C07C 209/78 from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines

Abstract

Disclosed herein is a process for preparing a reaction product containing methylene diphenylamine comprising reacting aniline with an aldehyde, in the presence of a low level of an acid wherein the acid level is reduced before digesting reaction mixture at a high temperature which is sufficient to effect a rearrangement of the intermediates to produce a reaction product containing methylene diphenylamines and low levels of impurities.

Claims

1. A process for preparing a reaction product containing methylene di(phenylamine) comprising reacting aniline with an formaldehyde, in the presence of a low level of an acid which is sufficient to catalyze the reaction at an initial and/or condensation stage of said reaction and produce methylene di(phenylamine)intermediates;

providing a reaction mixture at the condensation stage with an acid content which is at or below the initial acid level at the end of the condensation stage, and holding reaction mixture at a high temperature which is sufficient to effect a rearrangement of the intermediates to produce a reaction product containing methylene di(phenylamines) and low levels of impurities.

2. The process of claim 1 wherein the acid is hydrochloric acid.

3. The process of claim 1 wherein the low acid level is from 0.01 to 1.0 percent based on the weight of the reaction mixture.

4. The process of claim 1 wherein the acid level at the end of the condensation stage is at a low level.

5. The process of claim 1 wherein the acid content of the reaction mixture is reduced to a level below the level at the end of the condensation stage.

6. The process of claim 5 wherein the acid level is reduced to less than 1 percent by weight based on the weight of the reaction mixture.

7. The process of claim 1 wherein the acid level is reduced by partially neutralizing the reaction mixture with a base.

8. The process of claim 1 wherein the high temperature is in the range of 100 to 250 degrees Centigrade.

9. A reaction product comprising methylene di(phenylamine) which is prepared by the process of claim 1.

10. The reaction product of claim 9 which is characterized in that it contains low levels of impurities.

11. The reaction product of claim 9 which is characterized in that it contains low levels of N-methyl methylene di(phenylamine) and acridane and acridine.

12. A process for preparing an isocyanate product comprising phosgenating the product containing methylene di(phenylamine) as prepared in claim 1.

13. An isocyanate product which is prepared by the process of claim 12.

14. A process for preparing an isocyanate reaction product by reacting the isocyanate material of claim 13 with an active hydrogen containing material.

15. A process for preparing a foam comprising reacting the isocyanate material of claim 13 with an active hydrogen containing material in the presence of a blowing agent.

16. A foam which is prepared by the process of claim 15.