IP Library Granted Patent US 10,683,303
Granted Patent B2
US 10,683,303 · App. 16/306,719 · Granted Jun 16, 2020

Processes for producing methenamine mandelate

Inventors: Bryce Kelly Assink (Kalamazoo, MI); Tino Jon Caviggiola, III (Zeeland, MI)
Assignee: ALBEMARLE CORPORATION
C07D487/22C07B43/04C07C51/41C07C51/412C07D487/18
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,683,303
App. No.
16/306,719
Granted
Jun 16, 2020
Kind
B2
Abstract

Processes are provided for the production of methenamine mandelate that do not require the isolation of produced methenamine prior to production of the methenamine mandelate.

Claims (16)

1. A process comprising:

bubbling ammonia through a first combination comprising paraformaldehyde, a first C2-C6 alcohol, and water, while maintaining the first combination at about 20 deg. C. to about 90 deg. C., thereby producing a first reaction product comprising methenamine;

combining at least the first reaction product, mandelic acid, and a second C2-C6 alcohol under heat, thereby producing a second reaction product;

heating the second reaction product to a temperature of about 20 deg. C. to about 100 deg. C.; and

cooling the second reaction product to at least about 70 deg. C.,

thereby producing a composition comprising methenamine mandelate.

2. A process as in claim 1 wherein the first C2-C6 alcohol comprises n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

3. A process as in claim 1 wherein the second C2-C6 alcohol comprises as isopropanol, n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

4. A composition comprising methenamine mandelate, wherein the methenamine mandelate is prepared by a process comprising:

bubbling ammonia through a first combination comprising paraformaldehyde, a first C2-C6 alcohol, and water, while maintaining the first combination at about 20 deg. C. to about 90 deg. C., thereby producing a first reaction product comprising methenamine;

combining at least the first reaction product, mandelic acid, and a second C2-C6 alcohol under heat, thereby producing a second reaction product;

heating the second reaction product to a temperature of about 20 deg. C. to about 100 deg. C.; and

cooling the second reaction product to at least about 70 deg. C.,

thereby producing a composition comprising methenamine mandelate.

5. The composition of claim 1 , wherein the first C2-C6 alcohol comprises n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

6. The composition of claim 1 , wherein the second C2-C6 alcohol comprises as isopropanol, n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

Assignments (9)
RELEASE OF SECURITY INTEREST SUPPLEMENT NO. 3 Recorded Feb 2, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
Reel/Frame 074612/0540 →
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SUPPLEMENT NO. 1 TO PATENT SECURITY AGREEMENT Recorded Jan 23, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 074503/0861 →
SUPPLEMENT NO. 3 TO PATENT SECURITY AGREEMENT Recorded Jan 23, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 074503/0889 →
SUPPLEMENT NO. 3 TO PATENT SECURITY AGREEMENT Recorded Jan 23, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 074503/0898 →
SECURITY INTEREST (SUPPLEMENTAL NO. 3) Recorded Jan 22, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 074475/0514 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2021
From: ALBEMARLE CORPORATION
To: W.R. GRACE & CO.-CONN
Reel/Frame 057506/0960 →
SECURITY INTEREST Recorded Jun 2, 2021
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 056413/0277 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2020
From: ASSINK, BRYCE K.; CAVIGGIOLA, TINO JON, III
To: ALBEMARLE CORPORATION
Reel/Frame 052411/0425 →
Continuity (2)
Provisional Application 62345440 · Jun 3, 2016
Related Publication 20190127388A1 · May 2, 2019