Oligomerisation and alkylation reaction products of 2-phenylpropene and phenol

Partition coefficient

Link to relevant study record(s)

Reference

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Specific details on test material used for the study:

- Name of test material (as cited in study report): Phenol, methylstyrenated [CAS no. 68512-30-1] (Novares LA 300)
- Substance type: homogeneous mixture of oligomers and alkylation products
- Purity test date: no data
- Production date: 2009-02-31
- Batch No.: 28166
- Composition of test material: composition is specified in IUCLID Sect. 13 - Assessment reports under Certificate of Analysis_Novares LA 300_phenol, methylstyrenated
- Expiration date of the batch: 2011-12-31
- Stability under test conditions: H2O; EtOH; acetone; CH3CN; DMSO: 96h
- Storage condition of test material: Room temperature (20 +/- 5°C)

Type:

log Pow

Partition coefficient:

3.627

Temp.:

25 °C

pH:

5.5

Remarks on result:

other: Peak 1; sd: +/-0.007

Type:

log Pow

Partition coefficient:

5.75

Temp.:

25 °C

pH:

5.5

Remarks on result:

other: Peak 4; sd: +/- 0.005

Type:

log Pow

Partition coefficient:

6.145

Temp.:

25 °C

pH:

5.5

Remarks on result:

other: Peak 5; sd: +/- 0.004

Type:

log Pow

Partition coefficient:

> 6.2

Temp.:

25 °C

pH:

5.5

Remarks on result:

other: Peak 7

Details on results:

The values listed in the table below are the mean ± standard deviation of three independent determinations. The last small and large peak (peaks 6 and 7) lay outside the range of the method. Therefore the log POW of these peaks 6 and 7 should be stated as > 6.2.
As peak 2, 3 and 6 showed a relative area < 5%, they were considered as minor peaks.
Although area is not necessarily correlated to absolute concentration if a UV detector is used, it is supposed that the test item Novares LA 300 consists mainly of the peaks 1, 4, 5, and 7. Taking into account all four major peaks, a range of log POW between 3.672 and 6.297 was determined
(maximum of range is extrapolated; no reference item with log POW > 6.2 is mentioned in the guideline).

Tables are excerpts from the original report.

The chromatogram of the test item revealed seven peaks: four large and three small peaks (see Attached Document).

With the calibration function log K versus log P_OW, the corresponding log P_OWs were determined with:

Peak	Mean Area [mAU*min]	Rel. Area %	Mean retention time [min]	Log POW+sd
1	85.3807	14.02	5.701	3.672 ± 0.007
2	1.7543	0.29	6.812	3.945 ± 0.007
3	2.1134	0.35	26.470	5.750 ± 0.006
4	230.2626	37.82	31.317	5.957 ± 0.005
5	157.9556	25.94	36.555	6.145 ± 0.004
6	2.3566	0.39	39.590	6.242 ± 0.004
7	127.5514	20.95	41.419	6.297 ± 0.004

Table 9.1‑a           Retention times of reference items

Compound	RT1	RT2	RT3	RT4	RT5	RT6
	min.	min.	min.	min.	min.	min.
Thio urea	1.502	1.502	1.499	1.503	1.503	1.504
Acetophenone	2.259	2.263	2.263	2.266	2.265	2.266
Naphthalene	5.394	5.406	5.441	5.441	5.415	5.440
Diphenylether	7.183	7.204	7.262	7.275	7.217	7.262
Phenanthrene	10.176	10.201	10.294	10.325	10.243	10.301
Fluoranthene	14.084	14.137	14.251	14.330	14.196	14.289
Triphenylamine	24.813	24.954	25.200	25.379	25.061	25.250
DDT	35.215	35.491	35.882	35.958	35.679	35.939

Table 9.1‑b           Capacity factors (K) of reference items

Compound	Retention Time Mean	Retention Time Stand. Dev.	Retention Time Relative Stand. Dev.	K
	min.	min.	%
Thio urea	1.502*	0.002	0.115	-
Acetophenone	2.264	0.003	0.117	0.5069
Naphthalene	5.423	0.021	0.381	2.6100
Diphenylether	7.234	0.038	0.519	3.8156
Phenanthrene	10.257	0.060	0.582	5.8279
Fluoranthene	14.215	0.093	0.657	8.4627
Triphenylamine	25.110	0.207	0.826	15.7155
DDT	35.694	0.295	0.827	22.7617

* Dead time is 1.502 ± 0.002 minutes, with RSD 0.115 %.

Table 9.1‑c           

Log K and log P_OWof reference items

Compound	log K	log POW
Acetophenone	-0.2950	1.70
Naphthalene	0.4166	3.60
Diphenylether	0.5816	4.20
Phenanthrene	0.7655	4.50
Fluoranthene	0.9275	4.70
Triphenylamine	1.1963	5.70
DDT	1.3572	6.20

Description of key information

Due to the nature of the product, there is a range of log Pows. The range for the substance oligomerisation and alkylation reaction products of 2-phenylpropene and phenol (OAPP) (previous name: phenol, methylstyrenated) begins at 3.6 and extends to beyond 6.3 at 25°C.

Key value for chemical safety assessment

Log Kow (Log Pow):

6.3

at the temperature of:

25 °C

Additional information

A study according to OECD TG 117 was conducted on the substance oligomerisation and alkylation reaction products of 2-phenylpropene and phenol (previous name: phenol, methylstyrenated) to determine the log Pow. Due to the nature of the product, there is a range of log Pows. The range begins at about 3.6 and extends to beyond 6.3 at 25 °C. Read-across has indicated that these data are similar to that of cumylphenol (log Pow 3.8) and dicumylphenol (log Pow 6.73).