IP Library Granted Patent US 9,394,218
Granted Patent B2
US 9,394,218 · App. 14/903,619 · Granted Jul 19, 2016

Manufacture of methylolalkanes

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Quick Facts
Patent No.
US 9,394,218
App. No.
14/903,619
Granted
Jul 19, 2016
Kind
B2
Abstract

A multistage tubular reaction system and method for preparing methylol derivatives of an aldehyde includes a tubular reaction system with a plurality of successive reactor stages provided with a formaldehyde containing feed stream. The system includes multiple feed ports for the staged addition of C 2 or higher condensible aldehyde and/or base to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream, which is progressively provided with additional reactants as the production stream advances through the successive reaction stages. Advantages include better temperature control and reduced byproduct formation.

Claims (27)

1. A method of making a methylolalkane from formaldehyde and a C 2 or higher condensable aldehyde in a multistage process comprising:

(a) providing a formaldehyde containing stream to a tubular reaction system with a plurality of successive reaction stages;

(b) adding a C 2 or higher condensible aldehyde and optionally a base to the formaldehyde containing stream wherein at least one of the C 2 or higher condensible aldehyde or base are added to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde or base as the production stream advances through the successive reaction stages; and

(c) converting the C 2 or higher condensible aldehyde and formaldehyde to a methylolalkane.

2. The method according to claim 1 , wherein the C 2 or higher condensible aldehyde is added to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde as the production stream advances through the successive reaction stages.

3. The method according to claim 1 , wherein the methylolalkane is trimethylolpropane and the C 2 or higher condensible aldehyde is n-butyraldehyde.

4. The method according to claim 1 , wherein the methylolalkane is neopentyl glycol and the C 2 or higher condensible aldehyde is isobutyraldehyde.

5. The method according to claim 1 , wherein base is added to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional base as the production stream advances through the successive reaction stages.

6. The method according to claim 5 , wherein said base is an inorganic base selected from potassium hydroxide, calcium hydroxide and sodium hydroxide.

7. The method according to claim 1 , wherein said tubular reaction system has at least 3 stages.

8. The method according to claim 1 , comprising adding the C 2 or higher condensible aldehyde and an inorganic base to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde and inorganic base as the production stream advances through the successive reaction stages.

9. The method according to claims 8 , wherein said inorganic base is selected from potassium hydroxide, calcium hydroxide and sodium hydroxide.

10. The method according to claim 8 , wherein said C 2 or higher condensible aldehyde is added in a fixed proportion with inorganic base at said plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde as the production stream advances through the successive reaction stages.

11. The method according to claim 10 , wherein said C 2 or higher condensible aldehyde and inorganic base are provided in an upstream feed point in larger amounts relative to amounts provided in a downstream feed point.

12. The method according to claim 8 , wherein said inorganic base is provided in a downstream feed point in a larger amount relative to an amount provided in an upstream feed point to provide a production stream which is provided with inorganic base at higher levels in a later stage as compared with levels of inorganic base in an stage.

13. The method according to claim 1 , wherein the temperature of the production stream is maintained between 30° C. and 75° C.

14. A multistage tubular reaction system for preparing methylol derivatives of a C 2 or higher condensible aldehyde comprising:

(a) a tubular reaction system with a plurality of successive reactor stages comprising a plurality of reaction tubes cooled with a coolant in order to maintain a desired temperature;

(b) a reaction system inlet adapted to provide a formaldehyde containing stream to the tubular reaction system; and

(c) a plurality of feed ports adapted to provide at least one of the C 2 or higher condensible aldehyde or a base to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde or base as the production stream advances through successive reaction stages,

wherein the temperature of the production stream is maintained between 30° C. and 75° C.

15. The multistage tubular reaction system for preparing methylol derivatives of a C 2 or higher condensible aldehyde according to claim 14 , wherein the reaction system comprises a plurality of reaction tubes of a jacketed construction with an outer shell, an annular cooling channel and an inner reaction tube defining a reaction zone and wherein the annular cooling channel receives coolant.

16. A multistage tubular reaction system for preparing methylol derivatives of a C 2 or higher condensible aldehyde comprising:

(a) a tubular reaction system with a plurality of successive reactor stages comprising a plurality of reaction tubes cooled with a coolant in order to maintain a desired temperature;

(b) a reaction system inlet adapted to provide a formaldehyde containing stream to the tubular reaction system; and

(c) a plurality of feed ports adapted to provide at least one of the C 2 or higher condensible aldehyde or a base to the formaldehyde containing stream at a plurality of successive feed points to provide a production stream which is progressively provided with additional C 2 or higher condensible aldehyde or base as the production stream advances through successive reaction stages,

wherein the reaction system comprises a plurality of reaction tubes of a jacketed construction with an outer shell, an annular cooling channel and an inner reaction tube defining a reaction zone and wherein the annular cooling channel receives coolant.

Assignments (4)
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT [RECORDED ON JUNE 21, 2024 AT REEL 067806, FRAME 0536] Recorded Apr 8, 2025
From: CANTOR FITZGERALD SECURITIES [AS THE COLLATERAL AGENT]
To: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
Reel/Frame 070773/0022 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2024
From: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 067806/0536 →
CHANGE OF NAME Recorded Aug 25, 2021
From: OXEA BISHOP LLC
To: OQ CHEMICALS BISHOP LLC
Reel/Frame 057311/0541 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2016
From: STRUTZ, HEINZ; RAFF, DONALD K.; FREY, GUIDO D.; NOWOTNY, NORMAN; SCHROEDER, MARCOS L.; GAYTAN, FRED; HUNT, TRACY KEVIN; SLINKARD, WILLIAM E.
To: OXEA BISHOP LLC
Reel/Frame 037540/0437 →