From: Subject: United States Patent: 4900404 Date: Tue, 15 Jan 2008 14:54:56 -0600 MIME-Version: 1.0 Content-Type: multipart/related; type="text/html"; boundary="----=_NextPart_000_0000_01C85786.97EBDB30" X-MimeOLE: Produced By Microsoft MimeOLE V6.00.2900.3198 This is a multi-part message in MIME format. ------=_NextPart_000_0000_01C85786.97EBDB30 Content-Type: text/html; charset="Windows-1252" Content-Transfer-Encoding: quoted-printable Content-Location: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=4900404.PN.&OS=PN/4900404&RS=PN/4900404 United States Patent: 4900404

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United States Patent 4,900,404
Arnold ,   et al. February 13, 1990 =
Phosphate selective membrane electrode

Abstract

An improved phosphate selective membrane electrode using=20 bis(p-chlorobenzyl)tin dichloride as the membrane active component. In = addition=20 to this tin compound, the membrane contains N,N-dimethylformamide (DMF), = a=20 strong complexing agent for tin compounds.

Inventors: Arnold; Mark A. (Coralville, = IA),=20 Glazier; Scott A. (Iowa City, IA)
Assignee: University of Iowa Research = Foundation=20 (Iowa City, IA)
Appl. No.: 07/232,006
Filed: August 15, = 1988

Current U.S. = Class: 205/783.5 ; = 204/418
Current International = Class:=20 G01N = 27/333 (20060101); G01N=20 027/30 ()
Field of Search: = 204/1T,418 =

References Cited [Referenced=20 By]
U.S. Patent Documents
3445365 May 1969 Ross
4735692 April 1988 Arnold et al.

Other References

Zarinski, V. A. et al., "Electrochemical = Properties of=20 Liquid Membranes on Dialkyltin (IV) Compounds in Phosphorous (V)=20 Solutions", UDC 543.257.5:546.18, V.I. Vernadskii Institute of=20 Geochemistry and Analytical Chemistry, Acad. of Sci. of the USSR, = Moscow,=20 translated from Zhurnal Analiticheskoi Khimii, vol. 35, No. 11.=20 .
Zarinski V. A., et al. "Dialkyltin(IV) Compounds as Active = Components=20 of the Liquid Membranes of Ion-Selective Electrodes in Arsenic(V)=20 Solutions", UDC 543.257.1:546.19, V.I. Vernadskii Institute of=20 Geochemistry and Analytical Chem. Academy of Sciences of the USSR, = Moscow,=20 translated from Zhurnal Analiticheskoi Khimii, vol. 35, No. 11, = pp.=20 2143-2148, Nov. 1980..

Primary = Examiner:=20 Niebling; John F.
Assistant Examiner: Ryser; David G.=20
Attorney, Agent or Firm: Henderson & Sturm
Claims


We claim:

1. A phosphate ion selective membrane electrode = comprising:

a body member having an opening therein;

a = membrane=20 sealably attached to said body member over said opening, said membrane = including=20

a disubstituted aryl tin compound, and

a strong = complexing agent=20 for tin compounds;

a reference solution contained within said = body=20 member; and

a reference electrode disposed within said body = member in=20 contact with said reference solution.

2. The electrode of claim = 1=20 wherein said disubstituted aryl tin compound is selected from a group = consisting=20 of dibenzyltin dichloride and derivatives thereof.

3. The = electrode of=20 claim 2 wherein said disubstituted aryl tin compound is = bis(p-chlorobenzyl)tin=20 dichloride.

4. The electrode of claim 3 wherein said strong = complexing=20 agent for tin compounds is N,N-dimethylformamide.

5. The = electrode of=20 claim 2 wherein said strong complexing agent for tin compounds is=20 N,N-dimethylformamide.

6. The electrode of claim 1 wherein said = strong=20 complexing agent for tin compounds is N,N-dimethylformamide.

7. = A method=20 of determining the phosphate anion in a sample including the step of:=20

contacting said sample with an electrode comprising:

a = body=20 member having an opening therein;

a membrane sealably attached = to said=20 body member over said opening, said membrane including

a = disubstituted=20 aryl tin compound, and;

a strong complexing agent for tin = compounds;=20

a reference solution contained within said body member; and =

a=20 reference electrode disposed within said body member in contact with = said=20 reference solution.

8. The method of claim 7 wherein said = disubstituted=20 aryl tin compound is selected from a group consisting of dibenzyltin = dichloride=20 and derivatives thereof.

9. The method of claim 8 wherein said=20 disubstituted aryl tin compound is bis(p-chlorobenzyl)tin dichloride.=20

10. The method of claim 9 wherein said strong complexing agent = for tin=20 compounds is N,N-dimethylformamide.

11. The method of claim 8 = wherein=20 said strong complexing agent for tin compounds is N,N-dimethylformamide. =

12. The method of claim 7 wherein said strong complexing agent = for tin=20 compounds is N,N-dimethylformamide.
=20
Description


TECHNICAL FIELD

This invention relates to an = ion-selective=20 membrane electrode, and more particularly to an ion-selective electrode = with=20 improved response and selectivity characteristics for phosphate anions.=20

BACKGROUND ART

Phosphate ion is an extremely important = species=20 in many fields. Phosphate is present in numerous biological systems, is = a major=20 constitutent of many minerals and fertilizers, and is a component of = industrial=20 wastewater. Phosphate is an important analyte, yet only one basic method = exists=20 for its assay.

The importance of orthophosphate concentration = levels=20 spans all areas of science and technology. A system that can = continuously and=20 selectively monitor phosphate levels in aqueous solutions will find = numerous=20 applications in fields such as pharmacology, biomedical research, = clinical=20 chemistry, industrial process monitoring, environmental monitoring, etc. = Past=20 attempts to develop a selective membrane electrode for phosphate have = not been=20 successful. Much of this past work has involved construction of = electrodes based=20 on membranes composed of various insoluble salts. In general, electrodes = with=20 either poor selectivity over common anions or impractically high = detection=20 limits have resulted from these previous attempts. A variety of liquid = membranes=20 and systems based on enzymatic reactions have also been investigated and = found=20 to be unsuitable for the selective determination of orthophosphate. =

A=20 series of extracting agents for phosphate and arsenate anions have been=20 introduced. Long chain dialkyltin dinitrate species, such as dioctyltin=20 dinitrate and didodecyltin dinitrate, are used to separate phosphate and = arsenate from other anions by selective extraction into an organic = layer. Liquid=20 membrane electrodes employing these extraction agents have been = demonstrated.=20 Although it has been unsuccessful in developing phosphate selective = polymer=20 membrane electrodes with dialkyltin salts, it has been discovered that = the=20 incorporation of dibenzyltin dichloride derivatives into a plasticized = PVC=20 membrane gives a selective response to phosphate. Resulting electrodes = possess=20 practical detection limits and useful dynamic ranges of response.=20

Membrane electrodes containing dibenzyltin dichloride or=20 bis(p-methylbenzyl)tin dichloride as active material have been disclosed = in U.S.=20 Pat. No. 4,735,692 which is incorporated herein by reference. Subsequent = studies=20 have shown that the response and selectivity characteristics of this = known=20 electrode were lacking in many respects.

Those concerned with = these and=20 other problems recognize the need for an improved phosphate selective = membrane=20 electrode.

DISCLOSURE OF THE INVENTION

The present = invention=20 provides an improved phosphate selective membrane electrode using=20 bis(p-chlorobenzyl)tin dichloride as the membrane active component. In = addition=20 to this tin compound, the membrane contains N,N-dimethylformamide (DMF), = a=20 strong complexing agent for tin compounds.

The exact role DMF = takes in=20 establishing electrode response is not known at this time. Simon and = co-workers=20 (Mikrochimica Acta [Wien] 1986 III, 225), in studies on triorganotin = compounds=20 as active materials for membrane electrodes, have added compounds to = their=20 membranes which may play a role similar to DMF in determining electrode = response=20 and selectivity. DMF and other complexing agents like DMF are thought to = be=20 important additives for the membrane.

The previously disclosed = membrane=20 electrodes containing dibenzyltin dichloride or bis(p-methylbenzyl)tin=20 dichloride as active material have been found to be inferior in many = respects to=20 the present electrodes containing bis(p-chlorobenzyl)tin dichloride as = active=20 material (with DMF as an additive). The present electrode has been = studied much=20 more extensively than the previously disclosed electrodes. The results = of these=20 studies clearly show the superior selectivity of the = bis(p-chlorobenzyl)tin=20 dichloride containing electrode for phosphate over many common anions. = In=20 addition to enhanced selectivity, the limit of detection and linear = response=20 range for phosphate are improved. None of the other electrodes = constructed in=20 the past employing organotin compounds have proven to be very responsive = or=20 selective for orthophosphate.

An object of the present invention = is the=20 provision of an improved phosphate selective membrane electrode using=20 bis(p-chlorobenzyl)tin dichloride as the membrane component. =

Another=20 object of the present invention is to provide a phosphate selective = membrane=20 electrode that shows superior selectivity for phosphate over many common = anions.=20

A further object of the invention is the provision of an = improved limit=20 of detection and linear response for phosphate.

Still another = object is=20 to provide an electrode that employs bis(p-chlorobenzyl)tin dichloride = as a=20 membrane active component.

A still further object of the present = invention is the provision of an electrode employing organotin compounds = that=20 have proven to be responsive and selective for orthophosphate. =

Yet=20 another object of the present invention is the provision of an electrode = that=20 possesses greater selectivity for phosphate over ions such as chloride, = nitrate,=20 bromide, iodide, sulfate, and acetate.

BRIEF DESCRIPTION OF THE = DRAWINGS=20

These and other attributes of the invention will become more = clear upon=20 a thorough study of the following description of the best mode for = carrying out=20 the invention, particularly when reviewed in conjunction with the = drawings,=20 wherein:

FIG. 1 is a schematic representation of the disclosed = phosphate=20 selective electrode; and

FIG. 2 is a graph showing the response=20 performance of the electrode of the present invention to various anions = using a=20 buffer of 0.01M Tris-H.sub.2 SO.sub.4, pH 7.00 using potassium salts of = the=20 anions.

BEST MODE FOR CARRYING OUT THE INVENTION =

Referring now=20 to the drawings, wherein like reference numerals designate identical or=20 corresponding parts throughout the several views, FIG. 1 shows the = phosphate=20 selective membrane electode generally designated by the reference = numeral 10.=20 The electrode (10) includes a body section (12) formed of a disposable = pipet tip=20 and having a lower opening sealed by a phosphate selective polymer = membrane=20 (14). The body section (12) contains an internal reference solution (16) = of 0.1M=20 KCl and an internal reference electrode (18) comprising a Ag/AgCl = reference=20 wire. The phosphate selective membrane (14) owes its sensitivity to a=20 di-substituted aryl tin compound used as a membrane active component.=20

Composition of the selective membrane (14) includes=20 bis(p-chlorobenzyl)tin dichloride together with N,N-dimethylformamide in = a=20 poly(vinyl chloride) (PVC) matrix. The resulting electrode (10) = demonstrates=20 selectivity for orthophosphate over many common anions, such as sulfate, = acetate, chloride, bromide, nitrate and iodide. A detection limit of=20 3.4.times.10.sup.-5 M and a linear range of response from = 2.2.times.10.sup.-4 M=20 to 1.2.times.10.sup.-2 M are obtained when operated in a pH 7.0 buffer. = Slopes=20 of -32.9.+-.0.3 mV/decade are obtained which match the theoretical value = of the=20 dibasic species. In addition, the electrode lifetime is at least 28 days = when=20 electrodes are stored in this buffer at room temperature. When stored = dry, the=20 membranes are stable for at least one month.

Orthophosphate = selective=20 electrodes (10) were constructed by formation of the active PVC membrane = (14) at=20 the tip of a short length of Nalgene tubing (15). The polymer membrane = was=20 formed by dipping the electrode tip in a membrane casting solution and = allowing=20 the solvent of this solution to evaporate between successive = applications. The=20 membrane casting solution consisted of 70.5 mg bis(p-chlorobenzyl)tin=20 dichloride, 133.5 mg PVC (High molecular weight; Aldrich Chemical Co.,=20 Milwaukee, Wis.), 141.9 mg dibutyl sebacate (Eastman Kodak Co., = Rochester,=20 N.Y.), 48.3 mg N,N-dimethylformamide (Omnisolve; EM Science, Cherry = Hill, N.J.),=20 and 3 mL tetrahydrofuran (Gold Label; Aldrich Chemical Co.).=20 Bis(p-chlorobenzyl)tin dichloride was synthesized according to the = procedure of=20 Kinugawa et al.

Electrode response was obtained in a pH = 7.00.+-.0.01=20 working buffer that consisted of 10 mM tris(hydroxymethyl) aminomethane = (Tris)=20 with a 4.5 mM sulfuric acid. All interference studies were carried out = in this=20 buffer and the pH was continuously monitored and maintained at = 7.00.+-.0.01=20 throughout. Electrodes were conditioned prior to operation by soaking = the=20 polymer membrane in 1 liter of the working buffer for 20 hours followed = by a=20 brief exposure to 10 mM phosphate. Ion activities were calculated based = on the=20 theory of Davies.

The response to dibasic orthophosphate for a = series of=20 anion-responsive membrane electrodes is discussed below for electrodes = prepared=20 with (1) a conventional tetraalkylammonium ion-exchanger (R.sub.4 = N.sup.+), (2)=20 bis(p-methylbenzyl)tin dichloride, (3) dibenzyltin dichloride, and (4)=20 bis(p-chlorobenzyl)tin dichloride. Each response represents the average = of eight=20 individual electrodes.

The tetraalkylammonium ion-exchanger = membrane=20 yields minimal response to orthophosphate as expected. The response for=20 conventional membranes, such as this, is based on a combination of = simple=20 ion-exchange and ion lipophilicity. Increase in the lipophilicty of the = anion=20 makes it easier for it to enter the lipophilic membrane and, therefore, = to=20 generate a response. As a result, conventional anion selective = electrodes=20 respond well to lipophilic anions (such as thiocyanate), but they = respond poorly=20 to oxy-anions (such as orthophosphate).

In contrast, membranes = based on=20 the tin compounds all respond better to orthophosphate than the=20 tetraalkylammonium ion based membranes. Within the group of tin = compounds, the=20 bis(p-chloro) derivative provides the best response toward = orthophosphate. The=20 bis(p-chloro) derivative provides the best response toward = orthophosphate. The=20 bis(p-chloro) derivative provides a linear response to dibasic = orthophosphate=20 from 0.2 to 12.9 mM with a slope of -33.0.+-.0.1 mV/decade. This slope = closely=20 matches the theoretical Nernstian value of -29.6 mV/decade for a = divalent anion.=20 Detection limit for this membrane electrode is 0.034.+-.0.002 mM. In = comparison,=20 detection limits of 0.249.+-.0.008 and 0.134.+-.0.007 mM have been = measured for=20 the bis(p-methylvenzyl) tin dichloride and dibenzyltin dichloride based=20 membranes, respectively. An enhancement in the detection limit of = approximately=20 one order of magnitude is achieved with the bis(p-choro) derivative. The = response from the tetraalkylammonium ion based membrane is so poor for=20 orthophosphate that a detection limit cannot be accurately estimated = from its=20 response curve.

Electrode selectivity has been measured by = directly=20 comparing the electrode response to orthophosphate and to other common = anions.=20 FIG. 2 shows the response from electrodes composed of the bis(p-chloro)=20 derivative to orthophosphate, thiocyanate, iodide, fluoride, nitrate, = bromide,=20 chloride and acetate.

Electrode selectivity has been quantified = by using=20 activity ratios. These activity ratios indicate the apparent phosphate = activity=20 (concentration) for a given activity of the interfering ion (apparent=20 orthophosphate activity/corresponding interfering ion activity). Values = greater=20 than unity indicate the electrode is more selective for the interfering = ion,=20 values less than unity indicate the electrode is more selective for=20 orthophosphate, and a value of unity indicates equal selectivity for the = two=20 ions in quesetion. Absolute specificity is indicated by an activity = ratio of=20 zero.

Table 1 lists the activity ratios for orthophosphate over = the=20 anions tested. Values are represented for each of the membranes studied=20 (tetraalkylammonium ion, bis(p-methylbenzyl) tin dichloride, dibenzyltin = dichloride, and bis(p-chlorobenzyl)tin dichloride). All of the tin-based = membranes display greater selectivity for orthophosphate than the = conventional=20 membrane. In addition, selectivity for orthophosphate increases in going = from=20 the bis(p-methyl) to the dibenzyl to the bis(p-chloro) derivatives. = Values above=20 zero of the logarithm of the activity ratio for each of the membranes = examined=20 and for each of the anions tested demonstrate selectivity for the = interfering=20 ion and those less than zero indicate selectivity for phosphate. An = improvement=20 in selectivity of more than three orders of magnitude is provided by the = bis(p-chloro) derivative in comparison to conventional anion selective = membrane=20 electrodes.

As expected, slopes of the response curves for these = anions=20 differ according to the magnitude of charge on the anion tested (see = FIG. 2). A=20 slope of -59.16 mV/decade is expected for monovalent anions, while a = slope of=20 only -29.58 mV/decade is expected for divalent anions. Differences in = response=20 slope result in a concentration dependency for the activity ratios and = the=20 electrode selectivity. Such concentration dependent selectivity must be=20 considered in the methodology development stage.

Overall, the=20 selectivity pattern for the bis(p-chloro) derivative is:

TABLE 1 = ______________________________________ Activity Ratios* for Tested=20 Anion-Responsive Membrane Electrodes. bis-(p- bis(p- R.sub.4 N.sup.+ = Methyl)=20 Dibenzyl Chloro) ______________________________________ thiocyanate = (SCN.sup.-)=20 446 135 23 0.87 iodide (I.sup.-) 310 24 8.7 0.17 fluoride (F.sup.-) -- = -- --=20 0.13 nitrate (NO.sub.3.sup.-) 62 3.6 0.76 0.014 bromide (Br.sup.-) 24 = 1.8 0.52=20 0.0087 chloride (Cl.sup.-) 1.1 0.35 0.11 0.0026 acetate (OA.sub.c.sup.-) = -- --=20 -- 0.0033 ______________________________________ *Apparent Dibasic=20 Orthophosphate Conc/Interferent Conc

Usable calibration curves = for=20 dibasic orthophosphate are obtained over a 28 day period when electrodes = are=20 stored in the working buffer at room temperature between measurements. = After=20 approximately two weeks of use, however, the detection limit begins to = gradually=20 deteriorate and slightly shorter linear ranges are observed. Detection = limits=20 below the millimolar activity level are observed even after 28 days. = Prepared=20 membranes that are kept dry (under conditions of ambient humidity) at = room=20 temperature can be stored for at least one month without any detectable = adverse=20 effect on electrode calibration or selectivity.

The=20 dis(p-chlorobenzyl)tin dichloride based membrane electrode possesses = selectivity=20 for dibasic orthophosphate that is clearly superior to previous = anion-selective=20 polymer membrane electrodes. Based on the excellent selectivity, low = detection=20 limits and favorable lifetimes of this membrane electrode, development = of=20 practical continuous monitor systems for orthophosphate is now possible. =

While only certain preferred embodiments of this invention have = been=20 shown and described by way of illustration, many modifications will = occur to=20 those skilled in the art and it is, therefore, desired that it be = understood=20 that it is intended herein to cover all such modifications that fall = within the=20 true spirit and scope of this invention.

* * * * *
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