# US 2010/0163494 A1 · Preparation of environmentally acceptable scale inhibitors

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- Number: US 2010/0163494 A1
- Document ID: US20100163494A1
- Status: Published application
- Kind: A1
- Application number: 12/492,825
- Filed: 2009-06-26
- Published: 2010-07-01
- Earliest claimed: 2008-06-30
- Assignees: Champion Technologies, Inc.
- Inventors: Scot H. Bodnar; Henry C. Fisher; Andrew Frederick Miles; Curtis D. Sitz
- Web page: https://patentgrep.com/patent/US20100163494A1

## CPC

- C02F 5/12: containing nitrogen (C02F5/14 takes precedence)
- C02F 5/14: containing phosphorus
- C02F 2103/10: from quarries or from mining activities
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)

## Abstract

Alkyl phosphonates prepared from amino acids suitable for use in inhibiting scale. The phosphonates are obtained as reaction mixtures where the level of alkyl phosphonation is deliberately controlled to provide only partial alkyl phosphonation of the amino acid. The resulting alkyl phosphonates exhibit improved environmental properties compared to the fully substituted species, while still exhibiting acceptable efficacy in the control of scale. The compositions possess advantages over existing phosphonates in that they exhibit higher biodegradation by method OECD 306. They also offer lower toxicity to marine life compared to the fully substituted species and are not expected to bioaccumulate.

## Claims

### Claim 1

A method of inhibiting scale, comprising:
contacting an aqueous fluid with a scale inhibitor component in an amount effective to inhibit scale, wherein the scale inhibitor component includes at least one alkyl phosphonated amino acid species that comprises greater than 50 weight percent partially substituted, di-alkyl phosphonated amino acid species, and wherein the scale inhibitor component demonstrates greater than about 20% biodegradation in 28 days when tested according to method OECD 306.

### Claim 2 (depends on 1)

The method of claim 1, wherein the di-substituted alkyl phosphonated amino acids species includes an amino acid functionality having four or more active hydrogen.

### Claim 3 (depends on 2)

The method of claim 2, wherein the amino acid functionality is synthetic.

### Claim 4 (depends on 2)

The method of claim 2, wherein the amino acid functionality is selected from the group consisting of arginine, asparagine, glutamine, histidine, lysine, tryptophan, and combinations thereof.

### Claim 5 (depends on 2)

The method of claim 2, wherein the amino acid functionality is lysine.

### Claim 6 (depends on 1)

The method of claim 1, wherein the alkyl phosphonated amino acid species are methyl phosphonated amino acid species.

### Claim 7 (depends on 1)

The method of claim 1, wherein the scale inhibitor demonstrates greater than about 40% biodegradation in 28 days when tested according to method OECD 306.

### Claim 8 (depends on 1)

The method of claim 1, wherein the scale inhibitor demonstrates greater than about 40% biodegradation in 63 days when tested according to method OECD 306.

### Claim 9 (depends on 1)

The method of claim 1, wherein the scale inhibitor demonstrates greater than about 60% biodegradation in 63 days when tested according to method OECD 306.

### Claim 10 (depends on 5)

The method of claim 5, wherein the mixture of alkyl phosphonated lysine species includes greater than 60 weight percent di-substituted alkyl phosphonated lysine.

### Claim 11 (depends on 1)

The method of claim 1, wherein the scale inhibitor component has greater biodegradability than a scale inhibitor component including greater than 50 weight percent of a fully-substituted alkyl phosphonated amino acid.

### Claim 12 (depends on 1)

The method of claim 1, wherein the at least one alkyl phosphonated amino acid species is in the salt form.

### Claim 13 (depends on 12)

The method of claim 12, wherein the at least one alkyl phosphonated amino acid species forms a salt with sodium, potassium, ammonia, monoethanolamine, or combinations thereof.

### Claim 14 (depends on 1)

The method of claim 1, wherein the at least one alkyl phosphonated amino acid species is in the acid form.

### Claim 15 (depends on 1)

The method of claim 1, wherein the amount effective to inhibit scale establishes a concentration between 1 ppm and 100 ppm in the aqueous fluid.

### Claim 16 (depends on 5)

The method of claim 5, wherein the lysine is L-lysine.

### Claim 17 (depends on 1)

The method of claim 1, wherein the scale inhibitor is formulated with additives for use in an application selected from oilfield streams, industrial water treatment, laundry, detergents, industrial cleaning, residential cleaning and medical.

### Claim 18 (depends on 1)

The method of claim 1, wherein the step of contacting includes controllably adding an aqueous solution having the scale inhibitor dissolved therein through a small diameter tube positioned within a well bore in fluid communication with a subterranean formation.

### Claim 19 (depends on 1)

The method of claim 1, wherein the at least one alkyl phosphonated amino acid species includes two or more methyl phosphonated lysine species.

### Claim 20 (depends on 1)

The method of claim 1, wherein the at least one alkyl phosphonated amino acid species comprises at least one methyl phosphonated lysine species including greater than about 50 weight percent di-substituted methyl phosphonated lysine.

### Claim 21 (depends on 21)

The method of claim 21, wherein the scale inhibitor demonstrates greater than about 40% biodegradation in 28 days when tested according to method OECD 306.

### Claim 22 (depends on 21)

The method of claim 21, wherein the scale inhibitor demonstrates greater than about 60% biodegradation in 28 days when tested according to method OECD 306.

### Claim 23 (depends on 21)

The method of claim 21, wherein the scale inhibitor demonstrates greater than about 60% biodegradation in 63 days when tested according to method OECD 306.

### Claim 24 (depends on 21)

The method of claim 21, wherein the mixture of methyl phosphonated lysine species is in the form of a salt prepared by reacting the reaction mixture with monovalent cations, divalent cations, nitrogen containing species, or combinations thereof.

### Claim 25 (depends on 21)

The method of claim 21, where the mixture of methyl phosphonated lysine species is used for the control of scale in aqueous oilfield fluid.

### Claim 26 (depends on 21)

The method of claim 21, wherein the mixture of methyl phosphonated lysine species is used for the control of scale in aqueous fluids associated with applications selected from the group consisting of industrial waste water, laundry, detergents, industrial cleaning and household cleaning.

### Claim 27

A method, comprising:
controlling the degree of phosphonoalkylation of one or more amino acid species having at least four active hydrogen atoms to produce an effective scale inhibitor composition including at least one alkylphosphonated amino acid species, wherein the at least one alkylphosphonated amino acid species includes greater than 50 weight percent di-substituted alkyl phosphonated amino species and demonstrates greater than about 20% biodegradation in 28 days when tested according to method OECD 306.

### Claim 28 (depends on 27)

The method of claim 27, wherein the scale inhibitor composition including greater than 50 weight percent di-substituted alkyl phosphonated amino acid species demonstrates greater biodegradation than a scale inhibitor composition including at least 50 weight percent fully-substituted alkyl phosphonated amino acid species.

### Claim 29

A scale inhibitor formulation, comprising:
a solvent;
a scale inhibitor composition within the solvent, wherein the scale inhibitor composition includes at least one alkyl phosphonated amino acid species, wherein greater than 50 weight percent of the at least one alkyl phosphonated amino acid species is a lysine functionality that is di-substituted with alkyl phosphonate groups, and wherein the scale inhibitor composition demonstrates greater than about 20% biodegradation in 28 days when tested according to method OECD 306.

### Claim 30 (depends on 29)

The formulation of claim 29, wherein the alkyl phosphonate groups are methyl phosphonate groups.

### Claim 31 (depends on 29)

The formulation of claim 29, wherein the scale inhibitor composition demonstrates greater than about 40% biodegradation in 28 days when tested according to method OECD 306.

### Claim 32 (depends on 29)

The formulation of claim 29, wherein the scale inhibitor composition demonstrates greater than about 40% biodegradation in 63 days when tested according to method OECD 306.

### Claim 33 (depends on 29)

The formulation of claim 29, wherein the scale inhibitor composition demonstrates greater than about 60% biodegradation in 63 days when tested according to method OECD 306.

### Claim 34 (depends on 30)

The formulation of claim 30, wherein the scale inhibitor composition includes greater than 60 weight percent di-substituted methyl phosphonated lysine.