Phthalate Esters - ACS Reagent Chemicals (ACS Publications)

Feb 28, 2017 - Identity by. Infrared spectroscopy. Passes test. Gas chromatography–mass spectrometry. Passes test. Assay by. Gas chromatography. ≥...
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Monograph pubs.acs.org/doi/book/10.1021/acsreagents

Phthalate Esters Part 5, Assay and Identification of Standard-Grade Reference Materials: Specifications and Tests eISBN: 9780841230460 Tom Tyner Chair, ACS Committee on Analytical Reagents James Francis Secretary, ACS Committee on Analytical Reagents

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ABSTRACT This ACS Reagent Chemicals Standard-Grade Reference Materials monograph for Phthalate Esters, in addition to common physical constants, details the following specifications and corresponding tests for verifying that a substance meets ACS Standard-Grade specifications including: Identity by Infrared Spectroscopy, Identity by Gas Chromatography−Mass Spectrometry, Assay by Gas Chromatography, and Assay by Thin-Layer Chromatography.

SPECIFICATIONS Identity by Infrared spectroscopy. . . . . . . . . . . . . . . . . Passes test Gas chromatography–mass spectrometry . . . . . Passes test

Assay by Gas chromatography . . . . . . . . . . . . . . . . . ≥98.0% Thin-layer chromatography . . . . . . . . . . . . . Passes test

TESTS Identity by Infrared Spectroscopy Analyze the sample using the general procedure cited in [Part 2: Infrared Spectroscopy]. The spectrum must be consistent with either (1) the identifying ions listed for the compound in Table 5-8 or (2) the spectrum listed for the compound in the NIST standardized library of compounds. However, absorbance frequency and intensity may be different due to different analysis techniques. The spectrum may also be compared to other published libraries of infrared spectra, if available. Table 5-8. Phthalate Ester Compound Data

Name

CAS No.

Chemical Formula

Formula Weight

MS (m/z) MS-1

MS (m/z) MS-2

MS (m/z) MS-3

IR (cm−1) IR (cm−1) IR (cm−1) IR-1 IR-2 IR-3

Dimethyl isophthalate

1459-93-4

C10H10O4

194.2

163

135

194

1728

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726

DOI:10.1021/acsreagents.5009 ACS Reagent Chemicals, Part 5

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Table 5-8. Phthalate Ester Compound Data (continued)

Name

CAS No.

Chemical Formula

Formula Weight

MS (m/z) MS-1

MS (m/z) MS-2

MS (m/z) MS-3

IR (cm−1) IR (cm−1) IR (cm−1) IR-1 IR-2 IR-3

Dimethyl phthalate

131-11-3

C10H10O4

194.2

163

77

194

1729

11291

1126

Diethyl phthalate

84-66-2

C12H14O4

222.2

149

177

150

1727

1286

1074

Diallyl phthalate

131-17-9

C14H14O4

246.3

149

189

98

1728

1277

1126

Di-n-propyl phthalate

131-16-8

C14H18O4

250.3

149

76

150

1728

1281

1124

Di-n-butyl phthalate

84-74-2

C16H22O4

278.3

149

150

57

1731

1287

1122

Diisobutyl phthalate

84-69-5

C16H22O4

278.3

149

57

223

1727

1287

1123

Bis(2-methoxy-ethyl) phthalate

117-82-8

C14H18O4

282.3

59

58

149

1728

1288

1123

Diamyl phthalate

131-18-0

C18H26O4

306.4

149

150

237

1729

1288

1123

Bis(2-ethoxy-ethyl) phthalate

605-54-9

C16H22O4

310.3

72

73

149

1270

1128

1744

Butyl benzyl phthalate

85-68-7

C19H20O4

312.4

149

91

206

1726

1286

1122

Diphenyl phthalate

84-62-8

C20H14O4

318.3

225

226

77

1270

1190

1736

Dicyclohexyl phthalate

84-61-7

C20H26O4

330.4

149

167

55

1719

1293

1128

Bis(4-methyl-2-pentyl) phthalate

146-50-9

C20H30O4

334.5

149

85

150

Dihexyl phthalate

84-75-3

C20H30O4

334.5

149

150

55

1729

1283

1124

Dibenzyl phthalate

523-31-9

C22H18O4

346.4

91

107

149

1285

1127

1735

Bis(2-n-butoxy-ethyl) phthalate

117-83-9

C20H30O6

366.5

149

57

56

1728

1286

1121

Bis(2-ethylhexyl) isophthalate

137-89-3

C24H38O4

390.6

112

167

70

1726

1234

1302

Bis(2-ethylhexyl) phthalate

117-81-7

C24H38O4

390.6

149

167

57

1729

1280

1123

Di-n-octyl phthalate

117-84-0

C24H38O4

390.6

149

279

57

1729

1286

1124

Dinonyl phthalate

84-76-4

C26H42O4

418.6

149

293

71

1729

1284

1127

Diisononyl phthalate

68515-48-0

C26H42O4

418.6

149

293

Di-n-decyl phthalate

84-77-5

C28H46O4

446.7

149

307

107

1750

1285

1124

Diisodecyl phthalate

26761-40-0

C28H46O4

446.7

149

307

1729

1287

1125

Diundecyl phthalate

3648-20-2

C30H50O4

474.7

149

57

321

1729

1287

1123

Ditridecyl phthalate

119-06-2

C34H58O4

530.8

149

57

71

1730

1272

1124

Note: Disononyl phthalate and diisodecyl phthalate are mixtures of branched chain isomers. The GC and GC–MS chromatograms indicate this mixture by the presence of many peaks over time. These compounds are best analyzed by GC–MS. See the following method for additional information: Consumer Products Safety Commission, Test Method: CPSC-CH-C1001-09.3 Standard Operating Procedure for Determination of Phthalates (http://www.cpsc.gov/about/cpsia/CPSC-CH-C1001-09.3.pdf).

Identity by Gas Chromatography−Mass Spectrometry Analyze the sample by gas chromatography–mass spectrometry using method GCMS–PE1 described below. Method GCMS−PE1 Ionization Mode . . . . . . . . . . . . . . . . . . . . Electron ionization/70 eV Column . . . . . . . . . . . . . . . . . . . . . . . . . . 5% Diphenyl–95% dimethylpolysiloxane, 30 m × 0.25 mm i.d., 0.25 µm film thickness

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DOI:10.1021/acsreagents.5009 ACS Reagent Chemicals, Part 5

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Temperature Program. Carrier Gas . . . . . . . Injector . . . . . . . . . Injector Temperature . Scan Range . . . . . . . Sample Size . . . . . . .

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. 50 °C for 1 min, then 10 °C/min to 300 °C, then hold 10 min . Helium at 1 mL/min . Split/splitless (50:1 split) . 250 °C . 50–550 amu . 1 µL of a 100 µg/mL solution

The identifying ions for the compound listed in Table 5-8 must be present. The spectrum is compared to a known reference material or the NIST standardized library of compounds, if available.

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Assay by Gas Chromatography Analyze the sample by gas chromatography using method GCMS–PE1 described below. Method GC–PE1 Column . . . . . . . . . . . . . . . . . . . . . . . . . . 50% Diphenyl–50% dimethylpolysiloxane, 30 m × 0.53 mm i.d., 1.5 µm film thickness Detector . . . . . . . . . . . . . . . . . . . . . . . . . Flame ionization Detector Temperature . . . . . . . . . . . . . . . . 300 °C Injector . . . . . . . . . . . . . . . . . . . . . . . . . Split/splitless (10:1 split) Injector Temperature . . . . . . . . . . . . . . . . . 250 °C Sample Size . . . . . . . . . . . . . . . . . . . . . . . 1 µL of a 2500 µg/mL solution Carrier Gas . . . . . . . . . . . . . . . . . . . . . . . Helium at 5 psi Temperature Program. . . . . . . . . . . . . . . . . 50 °C for 1 min, then 10 °C/min to 300 °C, then hold 10 min Measure the area under all peaks (excluding the solvent peak), and calculate the analyte content in area percent for each analysis.

Assay by Thin-Layer Chromatography Analyze the sample by thin-layer chromatography using the general procedure described in [Part 2: Chromatography; Recommended Procedures; Thin-Layer Chromatography]. The following specific conditions are also required. Stationary Phase . . . . . . . . . . . . . . . . . . . . Silica Mobile Phase . . . . . . . . . . . . . . . . . . . . . . 1:3 (v/v) ethyl acetate: hexane. The ratio of ethyl acetate to hexane may need to be adjusted depending on the polarity of the compound. Detection Method . . . . . . . . . . . . . . . . . . . UV at 254 nm and iodine Compound must exhibit a single spot.

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DOI:10.1021/acsreagents.5009 ACS Reagent Chemicals, Part 5