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Boiling point

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Reference
Endpoint:
boiling point
Type of information:
(Q)SAR
Adequacy of study:
key study
Study period:
03 April 2018
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification
Justification for type of information:
1. SOFTWARE
EPI Suite Version 4.11

2. MODEL (incl. version number)
MPBPVP (v1.43)

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
CAS: 73246-85-2: CCCCCCCCCCCCOC(=O)CS[Sn](CCCCCCCC)(CCCCCCCC)SCC(=O)OCCCCCCCCCCCC
CAS: 79330-84-0: O=C(CS[Sn](SCC(=O)OCCCCCCCCCCCCCC)(CCCCCCCC)CCCCCCCC)OCCCCCCCCCCCCCC

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
- Estimation Methodology
MPBPWIN estimates the normal boiling point using an adaptation of the Stein and Brown (1994) method which is an extension and refinement of the Joback method (Joback, 1982; Reid et al, 1987).  The Stein and Brown (1994) method is a group contribution QSAR (quantitative structure activity relationship) method that calculates boiling point (Tb) of a compound by adding group increment values according to the relationship:

Tb  =  198.2  + Σ( ni * gi )

where  gi  is a group increment value and  ni  is the number of times the group occurs in the compound.  The resulting  Tb  (deg K) is then corrected by one of the following equations:

Tb (corr)  =  Tb  -  94.84  +  0.5577 Tb  -  0.0007705 (Tb)²   [Tb <= 700 K]
Tb (corr)  =  Tb  + 282.7  -  0.5209 Tb     [Tb > 700 K]

The Stein and Brown (1994) method was developed using a training dataset of boiling points for 4426 diverse organic compounds collected from the Aldrich Handbook (Aldrich, 1990).

MPBPWIN incorporates additional extensions to Stein and Brown Method such as (1) new group contributions missing from Brown and Stein (e.g. thiophosphorus [P=S], quaternary ammonium) and (2) correction factors for specific types of compounds (e.g. amino acids, various aromatic nitrogen rings, and phosphates).

- Estimation Accuracy
The Stein and Brown method was derived from a training set of 4426 diverse organic compounds with following reported statistical accuracy (Stein and Brown, 1994):

 Average absolute error = 15.5 deg Kelvin
 Standard deviation = 24.6 deg Kelvin
 Average error = 3.2%

It was then validated on a dataset of 6584 compounds collected from HODOC (1990) (compounds not used in the training set) with the following statistical accuracy (Stein and Brown, 1994):

 Average absolute error = 20.4 deg Kelvin
 Standard deviation = 38.1 deg Kelvin
 Average error = 4.3%

The training and validation sets were not available.  However, a test set of 5890 compounds with available normal boiling points was collected from the PHYSPROP Database that is included with the EPI Suite.  Various compounds having boiling points were excluded (most inorganic compounds, compounds using reduced pressures).

5. APPLICABILITY DOMAIN
Currently there is no universally accepted definition of model domain. However, users may wish to consider the possibility that property estimates are less accurate for compounds outside the Molecular Weight range of the training set compounds, and/or that have more instances of a given fragment than the maximum for all training set compounds. It is also possible that a compound may have a functional group(s) or other structural features not represented in the training set, and for which no fragment coefficient was developed. These points should be taken into consideration when interpreting model results.
The complete training sets for MPBPWIN's estimation methodology are not available. Therefore, describing a precise estimation domain for this methodology is not possible.
The current applicability of the MPBPWIN methodology is best described by its accuracy in predicting vapour pressure as described in the Accuracy section.

6. ADEQUACY OF THE RESULT
Given that the substances are organic molecule within the Molecular Weight range of the training set compounds, the prediction is considered to be acceptable.
Qualifier:
according to guideline
Guideline:
other: REACH Guidance on QSARs R.6
Version / remarks:
May/July 2008
Deviations:
no
GLP compliance:
no
Type of method:
other: calculation
Specific details on test material used for the study:
- Molecular weight
CAS: 73246-85-2: 864.02
CAS: 79330-84-0: 920.13
Key result
Boiling pt.:
741.6
Remarks on result:
other: CAS 73246-85-2
Key result
Boiling pt.:
788.02
Remarks on result:
other: CAS 79330-84-0

CAS 73246-85-2

Boiling Point: 741.60 °C (Adapted Stein and Brown Method)

Type

Num

Boil Description

Coefficient

Value

Group

4

-CH3 [aliphatic carbon]

21.98

87.92

Group

38

-CH2- [aliphatic carbon]

24.22

920.36

Group

2

-C(=O)O [ester, aliphatic attach]

78.85

157.70

Group

2

-S- [aliphatic attach]

69.42

138.84

Group

1

Tin [Sn]

60.00

60.00

Corr

*

1

 

Diester-type

Equation constant

-35.00 

-35.00

198.18

Result- uncorr: Boiling point in deg Kelvin: 1528.00

Result-corr: Boiling point in deg Kelvin: 1014.76

Boiling point in deg C: 741.60

CAS 79330-84-0

Boiling Point: 788.02 °C (Adapted Stein and Brown Method)

Type

Num

Boil Description

Coefficient

Value

Group

4

-CH3 [aliphatic carbon]

21.98

87.92

Group

42

-CH2- [aliphatic carbon]

24.22

1017.24

Group

2

-C(=O)O [ester, aliphatic attach]

78.85

157.70

Group

2

-S- [aliphatic attach]

69.42

138.84

Group

1

Tin [Sn]

60.00

60.00

Corr

*

 1

Diester-type

Equation Constant

-35.00

 

-35.00

198.18

Result- uncorr: Boiling point in deg Kelvin: 1624.88

Result-corr: Boiling point in deg Kelvin: 1061.18

Boiling point in deg C: 788.02

Conclusions:
The boiling points of the test material components were calculated to be 741.60 and 788.02 °C.
Executive summary:

The boiling point of the test material was calculated using MPBPVP v1.43 (Sept 2010) 2000 U.S. Environmental Protection Agency. Given that the substances are organic molecule within the Molecular Weight range of the training set compounds, the prediction is considered to be acceptable.

The boiling points of the test material components were calculated to be 741.60 and 788.02 °C (Adapted Stein and Brown Method).

Description of key information

The boiling points of the test material components were calculated to be 741.60 and 788.02 °C (Adapted Stein and Brown Method).

Key value for chemical safety assessment

Additional information

The boiling point of the test material was calculated using MPBPVP v1.43 (Sept 2010) 2000 U.S. Environmental Protection Agency. Given that the substances are organic molecule within the Molecular Weight range of the training set compounds, the prediction is considered to be acceptable.

The boiling points of the test material components were calculated to be 741.60 and 788.02 °C (Adapted Stein and Brown Method).