Reaction mass of Resin acids and Rosin acids, hydrogenated, potassium salts and potassium [1R-(1α,4aβ,10aα)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carboxylate

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

29 April 2010 to 4 August 2010

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: GLP study; read-across from related substance (Resin 835 A)

Cross-reference

Reason / purpose for cross-reference:

reference to other study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2010

Report date:

2010

Materials and methods

Test guideline

Test guideline 1

Qualifier:

according to guideline

Guideline:

EU Method C.19 (Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge Using High Performance Liquid Chromatography (HPLC))

Deviations:

no

Test guideline 2

Qualifier:

according to guideline

Guideline:

OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))

Deviations:

no

GLP compliance:

yes

Type of method:

HPLC estimation method

Media:

soil/sewage sludge

Test material

Test material information

Constituent 1

Reference substance name:

Reaction mass of Rosin, hydrogenated and [1R-(1a,4aß,10aa)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carboxylic acid

IUPAC Name:

Reaction mass of Rosin, hydrogenated and [1R-(1a,4aß,10aa)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carboxylic acid

Constituent 2

Reference substance name:

Resin 835 A

IUPAC Name:

Resin 835 A

Specific details on test material used for the study:

Details on properties of test surrogate or analogue material (migrated information):
PHYSICO-CHEMICAL PROPERTIES
- pKa (calculated by the software PALLAS pKa Prediction Module 5.1, version 3.7.1.1): The calculated pKa's of the main components of "Resin 835 A"
are 5.1 (acidic group) each.

Radiolabelling:

no

Study design

Test temperature:

35 °C

HPLC method

Details on study design: HPLC method:

EQUIPMENT
- Apparatus: Finnigan Surveyor
- Type: HPLC
- analytical column: LiChrospher 100 CN 5 µm 150*3 mm; Col. No. Q31021; ARC Seibersdorf
- Detection system: DAD (UV 210 nm)

MOBILE PHASES Test 1
- Type: 45% methanol (Chromasolv, Sigma-Aldrich, Lot. No. SZBAO21S); 55% buffer* pH 4.0 in water (10 mMol/L potassiumdihydrogencitrate)
- Experiments with additives carried out on separate columns: no
- pH: 4.0
- Solutes for dissolving test and reference substances: Methanol and mobile phase

MOBILE PHASES Test 2
- Type: 40% methanol (Chromasolv, Sigma-Aldrich, Lot. No. SZBAO21S); 60% buffer* pH 6.5 in water (10 mMol/L potassiumdihydrogencitrate)
- Experiments with additives carried out on separate columns: no
- pH: 6.5
- Solutes for dissolving test and reference substances: Methanol and mobile phase

DETERMINATION OF DEAD TIME
The dead time t0 was determined by an unretained compound (sodium nitrate; assay 99.6 %; Lot 50330; Riedel de Haen).

REFERENCE SUBSTANCES
see results

DETERMINATION OF RETENTION TIMES
- Quantity of test substance introduced in the column: see results
- Quantity of reference substances: see results
- Intervals of calibration: on day of analysis

REPETITIONS
- Number of determinations: 2

According to the guidelines a minimum of six reference points, if possible at least one above and one below the expected value of the test substance
should be used.
Freshly prepared solutions of six reference compounds in the mobile phase were injected individually to identify their peak in this HPLC-system. Then
they were injected simultaneously (before and after the test substance) and the exact retention times were determined in duplicate. The corresponding capacity factors and logarithms of the capacity factors were calculated and plotted as a function of the log KOC.
A linear regression line was calculated from the data of this graph.
The log KOC values of the reference compounds are described in the guidelines.

SELECTION of pH
According to the guideline two tests should be performed, for ionisable substances with both ionised and non-ionised forms but only in cases where at least 10 % of the test compound will be dissociated within pH 5.5 to 7.5.
The pKa’s of the main components of the test substance were estimated using an atom/fragment contribution method (Software Pallas 3.7.1.1 pKa prediction module pKalc 5.1). The calculated pKa's are 5.1 (acidic group) each. The undissociated acid can be obtained by adjusting the pH to at least one pH-unit below the pKa. The acidic components will exist in the undissociated form at pH less than ca. 4.1 and in the dissociated form at pH greater than ca 6.1.
Therefore two experimental tests at pH 4.0 and pH 6.5 were performed.

Results and discussion

Adsorption coefficient

Adsorption coefficient 1

Type:

log Koc

Value:

> 3.1 - < 4.5

Temp.:

35 °C

Remarks on result:

other: pH 4.0

Adsorption coefficient 2

Type:

log Koc

Value:

> 0.9 - < 2

Temp.:

35

Remarks on result:

other: pH 6.5

Results: HPLC method

Details on results (HPLC method):

Test 1 at pH 4.0:
The actual pH value of the mobile phase during the test was 4.0.
The temperature during the test was 35 °C.
The calibration curve of the reference substances was: log k' = 0.2856 x log KOC – 0.4559 (see attachment)
Several unidentified compounds were found in the (log KOC) range of 3.1 to 4.5.
The adsorption coefficients log KOC of the main components of "Resin 835 A" are in the range of: 3.1 to 4.5 at pH 4.0.

Test 2 at pH 6.5:
The actual pH value of the mobile phase during the test was 6.5.
The temperature during the test was 35 °C.
The calibration curve of the reference substances was: log k' = 0.3341 x log KOC – 0.4534 ( see attachment)
Several unidentified compounds were found in the (log KOC) range of 0.9 to 2.0.
The adsorption coefficients log KOC of the dissociated main components of "Resin 835 A" are in the range of: 0.9* to 2.0 at pH 6.5.
*The experimentally determined log KOC is outside the range (1.5 to 5.0) for which the method is published in the guideline.

Any other information on results incl. tables

Table1: Reference and test substance purity and concentration

 

substances	purity (%)	concentration in mobile phase (mg/L)
sodium nitrate; batch no. 50330; Riedel de Haen.	99.6	19.8 and 20.0
acetanilide; batch no. 1399848; Fluka.	100.0	11.8
methyl benzoate; batch no. 1396465; Fluka.	99.9	11.6
isoproturon; batch no. SZE8200X; Fluka.	99.9	11.4
triadimenol; batch no. 5252X; Riedel de Haen.	98.4	11.0
naphthalene; batch no. 84679; Fluka.	99.9	11.0
1,2,3-trichlorobenzene; batch no. SZE8204X; Sigma-Aldrich.	99.9	10.8
α-endosulfan; batch no. 3309X; Riedel de Haen.	99.6	11.2
4’4 DDT; batch no. 5143X; Sigma-Aldrich.	99.1	10.2
"Resin 835 A"	see2.1	141.3

 

Table2: Results for reference and test substancestest 1 at pH 4.0

 

substance	retention time (minutes)		capacity factor k'		mean log k'	log KOC*
	a	b	a	b
sodium nitrate	1.16	1.16	--	--	--	--
methylbenzoate	2.45	2.44	1.11	1.10	0.04	1.80
isoproturon	2.69	2.69	1.32	1.32	0.12	1.86
triadimenol	3.14	3.14	1.71	1.71	0.23	2.40
1,2,3-trichlorobenzene	4.21	4.20	2.63	2.62	0.42	3.16
α-endosulfan	6.70	6.63	4.78	4.72	0.68	4.09
4'4 DDT	18.91	18.74	15.30	15.16	1.18	5.63
"Resin 835 A"
unknown component(s)	4.23	4.16	2.65	2.59	0.42	3.06
unknown component(s)	7.15	7.08	5.16	5.10	0.71	4.08
unknown component(s)	8.75	8.84	6.54	6.62	0.82	4.46

 

*The log K_OC-values of the reference compounds are taken from the guidelines.

Table3: Results for reference and test substances test 2 at pH 6.5

 

substance	retention time (minutes)		capacity factor k'		mean log k'	log KOC*
	a	b	a	b
sodium nitrate	1.16	1.16	--	--	--	--
acetanilide	2.13	2.13	0.84	0.84	-0.08	1.25
methylbenzoate	2.80	2.79	1.41	1.41	0.15	1.80
triadimenol	3.94	3.93	2.40	2.39	0.38	2.40
naphthalene	5.14	5.13	3.43	3.42	0.53	2.75
1,2,3-trichlorobenzene	5.49	5.48	3.73	3.72	0.57	3.16
α-endosulfan	10.10	9.99	7.71	7.61	0.88	4.09
"Resin 835 A"
unknown component(s)	1.96	1.96	0.69	0.69	-0.16	0.87
unknown component(s)	2.46	2.43	1.12	1.09	0.04	1.49
unknown component(s)	2.59	2.59	1.23	1.23	0.09	1.63
unknown component(s)	3.12	3.10	1.69	1.67	0.23	2.03

 

*The log K_OC-values of the reference compounds are taken from the guidelines.

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Conclusions:

The adsorption coefficients log KOC of the main components of "Resin 835 A" are in the range of: 3.1 to 4.5 at pH 4.0 and 0.9 to 2.0 at pH 6.5.

Executive summary:

The adsorption coefficient (log Koc) was determined using HPLC.

Test 1 at pH 4.0: The actual pH value of the mobile phase during the test was 4.0. The temperature during the test was 35 °C. The calibration curve of the reference substances was: log k' = 0.2856 x log KOC – 0.4559 (see attachment) Several unidentified compounds were found in the (log KOC) range of 3.1 to 4.5. The adsorption coefficients log KOC of the main components of "Resin 835 A" are in the range of: 3.1 to 4.5 at pH 4.0. Test 2 at pH 6.5: The actual pH value of the mobile phase during the test was 6.5. The temperature during the test was 35 °C. The calibration curve of the reference substances was: log k' = 0.3341 x log KOC – 0.4534 ( see attachment) Several unidentified compounds were found in the (log KOC) range of 0.9 to 2.0. The adsorption coefficients log KOC of the dissociated main components of "Resin 835 A" are in the range of: 0.9* to 2.0 at pH 6.5. *The experimentally determined log KOC is outside the range (1.5 to 5.0) for which the method is published in the guideline.