Use of 1-alkyl-5-oxopyrrolidine-3-carboxylic esters as gas hydrate inhibitors with improved biodegradability

• US 20090042747A1
• Filed: 08/01/2008
• Published: 02/12/2009
• Est. Priority Date: 08/06/2007
• Status: Active Grant

• Current Assignee: Clariant International AG (Clariant AG)
• Original Assignee: Clariant International AG (Clariant AG)
• Inventors: Feustel, Michael, Leinweber, Dirk, Roesch, Alexander
• Granted Patent: US 8,722,589 B2
• Time in Patent Office: Days
• US Class Current: 507/202
• CPC Class Codes: C09K 2208/22 Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers
• CPC Class Codes: C10L 3/10 Working-up natural gas or synthetic natural gas

Abstract

The invention provides for the use of 1-alkyl-5-oxopyrrolidine-3-carboxylic esters, preparable by esterifying alcohols having from 1 to 100 hydroxyl groups with 1-alkyl-5-oxopyrrolidine-3-carboxylic acid, in amounts of from 0.01 to 2% by weight for preventing the formation of gas hydrates in aqueous phases which are in contact with a gaseous, liquid or solid organic phase.

Claims

1. A process for preventing the formation of gas hydrates in an aqueous phase, wherein the aqueous phase is in contact with a qaseous, liquid or solid organic phase comprising the step of contacting the aqueous phase with at least one 1-alkyl-5-oxopyrrolidine-3-carboxylic ester in an amount of from 0.01 to 2% by weight, wherein the at least one 1-alkyl-5-oxopyrrolidine-3-carboxylic ester is prepared by esterifying at least one alcohol having from 1 to 100 hydroxyl groups with 1-alkyl-5-oxopyrrolidine-3-carboxylic acid.

2. The process as claimed in claim 1, wherein the alcohol corresponds to the formula (1)

R

OH]_n  

 

(1)

wherein R is an organic radical having from 1 to 100 carbon atoms and n is from 1 to 100.

3. The process as claimed in claim 2, wherein R is an alkyl, alkenyl or polyalkylene oxide radical having from 1 to 30 carbon atoms.

4. The process as claimed in claim 2, wherein n is from 1 to 10.

5. The process as claimed in claim 1, wherein the the alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, pentanol, isopropanol, isobutanol, isopentanol, 2-ethylhexanol, heptanol, octanol, decanol, ethylene glycol, propylene glycol, butylglycol, butyldiglycol, butyltriglycol, glycerol, diglycerol, triglycerol, tetraglycerol, polyglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, sorbitan, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tris(hydroxymethyl)aminomethane, dodecanol, tetradecanol, hexadecanol, octadecanol and oleyl alcohol.

6. The process as claimed in claim 1, wherein at least 30% of all OH groups present in the alcohol are esterified in the the at least one 1-alkyl-5-oxopyrrolidine-3-carboxylic ester.

7. The process as claimed in claim 3, wherein n is from 1 to 10.

8. A compound for preventing the formation of gas hydrates in an aqueous phase, wherein the aqueous phase is in contact with a gaseous, liquid or solid organic phase comprising at least one 1-alkyl-5-oxopyrrolidine-3-carboxylic ester, wherein the at least one 1-alkyl-5-oxopyrrolidine-3-carboxylic ester is prepared by esterifying at least one alcohol having from 1 to 100 hydroxyl groups with 1-alkyl-5-oxopyrrolidine-3-carboxylic acid.