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Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors

a technology of pyridinium and quinolinium compounds, which is applied in the field of new compounds, can solve the problems of inability to readily biodegrade compounds and often unacceptable biotoxicity profiles

Inactive Publication Date: 2008-12-18
ECOLAB USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]The corrosion inhibitor of the invention has a lower environmental impact when compared to existing commercial treatments by virtue of their low toxicity, higher biodegradation and lower bioaccumulation. In addition, the corrosion inhibitors of this invention are less volatile, hence less malodorous than, existing alkypyridine corrosion inhibitors.

Problems solved by technology

However, due to their inherent biostatic properties their biotoxicity profile is often unacceptable and the compounds are not readily biodegradeable.

Method used

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  • Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors
  • Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors
  • Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0045]Epichlorohydrin (34 g, 0.36 m) is heated at 80° C. with a catalytic amount of concentrated hydrochloric acid (1 ml) for 20 minutes to open the ring and obtain 1-chloro-2,3-dihydroxy-propane. This is condensed with 1.5 equiv. of tall oil fatty acids (155 g, 0.55 m) at 150° C. for 3 hours to obtain a mixture of mono and bis esters. Any residual hydrochloric acid is neutralised with solid sodium bicarbonate. Substituted pyridine (Alkolidine 12, available from Lonza Ltd., Basel, Switzerland, 95 g, 0.55 m) is added and the reaction mixture is heated at 150° C. for 2 hours to obtain the corresponding substituted pyridinium salt. Sodium chloride is filtered off and any other inorganics are removed by dissolving in water. Yield: 260 g.

example 2

[0046]Chloroacetic acid (20 g, 0.211 m) is heated with n-octanol (28 g, 0.22 m) at 120° C. for 2 hours in the presence of a catalytic amount of concentrated hydrochloric acid. The reaction mixture is allowed to cool and substituted pyridine (Alkolidine 12, 42 g, 0.22 m) is added. The reaction mixture is heated at 130° C. for another 2 hours to provide the substituted alkyl pyridinium ester. Yield 86 g.

example 3

Performance Testing

[0047]Standard Linear Polarisation Resistance (LPR) techniques in a ‘bubble’ or stirred kettle assembly are used to measure the instatanteous corrosion rate in the brine solution as a function of time. Synthetic seawater (deionised water containing 3% sodium chloride) saturated with CO2 and de-aromatised kerosene (LVT-200) are used in a 90:10 ratio at 60° C.

[0048]An automated electrochemical measurement system (ACM Instruments Gill 12) and associated software is used to conduct electrochemical measurements. Three pin probes constructed from type C1018 mild steel are used for all bubble test and Rotating Cylinder Electrode (RCE) measurements. Standard ranges of concentrations are examined to generate performance concentration curves in an environment where the inhibitor species has been allowed to partition. A blank corrosion rate for each cell is measured every 10 minutes for two hours whereupon chemical injection is made into the hydrocarbon phase. The corrosion ...

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Abstract

A quaternary nitrogen-containing corrosion inhibitor of formulawhereinis an aromatic, nitrogen-containing ring of 5 to 14 ring atoms, optionally containing an additional N, O or S ring atom and optionally substituted with one or more alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof, Y is a group of formula —OC(O)R1 or —C(O)R1; L is C1-C10 alkyl, C2-C10 alkenyl or a group of formula CH2CH(OR2)CH2—; R1 is C8-C20 alkyl or C8-C20 alkenyl; R2 is H or C(O)R1; R3 and R4 are independently selected from H, alkyl, alkenyl, amino, alkoxy, hydroxylalkyl and cyano; and X is Br, Cl or I is particularly useful for inhibiting corrosion in oil and gas field applications.

Description

TECHNICAL FIELD[0001]This invention relates to novel quaternary nitrogen compounds and compositions comprising the compounds which are useful as corrosion inhibitors, particularly in oil and gas field applications and more particularly in situations where they may come into contact with the natural environment, and to a method of inhibiting corrosion using the compounds.BACKGROUND OF THE INVENTION[0002]Stringent environmental constraints imposed by government regulation upon the oil and gas producing industry has led to the need for new “greener” chemistries, which have less environmental impact. This environmental drive has been spearheaded by North Sea Regulators such as CEFAS, and due to their success similar programs are being implemented in other oil producing regions. Operators now demand identical levels of performance with existing treatments along with the fulfillment of the new environmental criteria for any chemicals that may be contained, for example, in rig overboard di...

Claims

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Application Information

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IPC IPC(8): C23F11/14C07D211/82C07D215/00C07D219/00C07D237/02C07D237/28C23F11/16C07D239/20C07D239/72C07D263/32C07D263/52C07D277/22
CPCC07D213/04C07D215/10C23F11/149
Inventor TIWARI, LAXMIKANT
Owner ECOLAB USA INC
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