Reaction mass of 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(pentafluoroethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(trifluoromethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N,N-bis(heptafluoropropyl)propan-1-amine

Other distribution data

Administrative data

Endpoint:

other distribution data

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

key study

Study period:

2018

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Remarks:

Source data from guideline studies

Cross-reference

Cross-reference 1

Reason / purpose for cross-reference:

reference to other study

Reference

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Study period:

November 14, 2017 to November 28, 2017

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

EPA OPPTS 830.7550 (Partition Coefficient, n-octanol / H2O, Shake Flask Method)

GLP compliance:

no

Other quality assurance:

ISO/IEC 17025 (General requirements for the competence of testing and calibration laboratories)

Type of method:

flask method

Partition coefficient type:

octanol-water

Specific details on test material used for the study:

SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material: Lot 0002712253
- Expiration date of the lot/batch: 07/06/2020

Analytical method:

gas chromatography

mass spectrometry

Key result

Type:

log Pow

Partition coefficient:

6.14

Temp.:

25 °C

Remarks on result:

other: For Component A and H, % RSD = 0.72%

Remarks:

pH not measured

Key result

Type:

log Pow

Partition coefficient:

> 6.49

Temp.:

25 °C

Remarks on result:

other: For Component B, % RSD = 2.01%.

Remarks:

pH not measured.

Key result

Type:

log Pow

Partition coefficient:

5.46

Temp.:

25 °C

Remarks on result:

other: For Component D, %RSD = 1.08%

Remarks:

pH not measured

Key result

Type:

log Pow

Partition coefficient:

> 6.44

Temp.:

25 °C

Remarks on result:

other: For Component F, %RSD = 2.71%.

Remarks:

pH not measured

Details on results:

MTDID 50908 is a multi-constituent substance. Kow was determined for the compounds identified as Component A and Component H, Component B, Component D, Component F (Fig 1).

Table 2. Kow for individual components of MTDID 50908

Component	ratio	Vial# ^(3)	Octanol Conc. (ng/mL)	^(1)Water Conc.(ng/mL)	Kow ^(2)	Log Kow
Component A and H
	1:1	6	76300	0.0501	1520000	6.18
	1:1	8	82300	0.0530	1550000	6.19
		Avg (RPD%)	79300 (7.6%)	0.0516 (5.8%)	1540000 (1.8%)	6.19(0.1%)
	1:2	1	51300	0.0387	1330000	6.12
	1:2	3	50100	0.0377	1330000	6.12
	1:2	4	50500	0.0449	1120000	6.05
		Avg (RSD%)	50600 (1.2%)	0.0404 (9.7%)	1260000 (9.3%)	6.10 (0.71%)
	2:1	1	49400	0.0368	1340000	6.13
	2:1	3	48900	0.0338	1450000	6.16
	2:1	4	51600	0.0364	1420000	6.15
		Avg (RSD%)	50000 (2.9%)	0.0356 (4.6%)	1400000 (3.8%)	6.15 (0.29%)
Component A and H overall  average (RSD%)					1380000 (9.8%)	6.14 (0.72%)
Component B
	1:1	6	12000	< 0.00260	> 4610000	> 6.66
	1:1	8	12900	< 0.00260	>4980000	> 6.70
		Avg (RPD%)	12500 (7.7%)	< 0.00260 (N/A)	>4790000 (7.7%)	> 6.68 (0.35%)
	1:2	1	6740	< 0.00260	>2590000	> 6.41
	1:2	3	6580	< 0.00260	>2530000	> 6.40
	1:2	4	6590	< 0.00260	>2540000	> 6.40
		Avg (RSD%)	6640 (1.3%)	< 0.00260 (N/A)	>2550000 (1.3%)	> 6.41 (0.09%)
	2:1	1	6450	< 0.00260	>2480000	>  6.39
	2:1	3	6320	< 0.00260	>2430000	> 6.39
	2:1	4	6670	< 0.00260	>2570000	> 6.41
		Avg (RSD%)	6480 (2.7%)	< 0.00260 (N/A)	>2490000 (2.7%)	> 6.40 (0.19%)
Component B overall  average (RSD%)					>3090000 (34%)	> 6.49 (2.01%)
Component D
	1:1	6	2800	0.00891	315000	5.50
	1:1	8	3040	0.00919	331000	5.52
		Avg (RPD%)	2920 (8.2%)	0.00905 (3.2%)	323000 (5.1%)	5.51 (0.28%)
	1:2	1	2370	0.00823	288000	5.46
	1:2	3	2260	0.00819	276000	5.44
	1:2	4	2280	0.0107	214000	5.33
		Avg (RSD%)	2310 (2.5%)	0.00903 (16%)	259000 (15%)	5.41 (1.29%)
	2:1	1	2250	0.00803	280000	5.45
	2:1	3	2180	0.00688	317000	5.50
	2:1	4	2340	0.00813	288000	5.46
		Avg (RSD%)	2250 (3.5%)	0.00768 (9.1%)	295000 (6.7%)	5.47 (0.52)
Component D overall  average (RSD%)					289000 (13%)	5.46 (1.08%)
Component F
	1:1	6	3850	<0.000811	>4750000	> 6.68
	1:1	8	4090	<0.000811	>5040000	> 6.70
		Avg (RPD%)	3970 (5.9%)	< 0.000811 (N/A)	>4890000 (5.9%)	> 6.69 (0.27%)
	1:2	1	1730	<0.000811	>2130000	> 6.33
	1:2	3	1680	<0.000811	>2070000	> 6.32
	1:2	4	1670	<0.000811	>2060000	> 6.31
		Avg (RSD%)	1690 (1.7%)	< 0.000811 (N/A)	>2090000 (1.7%)	6.32 (0.12%)
	2:1	1	1640	<0.000811	>2030000	> 6.31
	2:1	3	1590	<0.000811	>1970000	> 6.29
	2:1	4	1700	<0.000811	>2090000	> 6.32
		Avg (RSD%)	1640 (3.2%)	< 0.000811 (N/A)	>2030000 (3.2%)	> 6.31 (0.20%)
Component F overall  average (RSD%)					>2770000 (48%)	> 6.44 (2.71%)

(1)    Value reported as “less than" due to concentration for the water phase were below the lower limit of quantitation.

(2)    Kow values reported as “greater than” due to the water phase concentration was “less than” the lower limit of quantitation.

(3)    Vials were excluded if at least one component had a concentration detected in the water phase that was above the reported

water solubility for this component, which suggest possible contamination from the octanol phase. For the 1: 1 ratio,

vials 1-5, and vial 7 were excluded. For the 1:2 and 2:1 ratio, vial #2 was excluded.

Conclusions:

MTDID 50908 is a multi-constituent substance. The partition coefficient (Kow) was determined for components identified as A, B, D, F and H. The average measured log Kow for Component A and H is 6.14 (RSD=0.72%), the average measured log Kow for Component B is > 6.49 (RSD=2.01%), the
average measured log Kow for Component D is 5.46 (RSD=1.08%), and the average measured log Kow for Component F is > 6.44 (RSD=2.71%).

Executive summary:

The n-Octanol/Water Partition Coefficient (log Kow) of MTDID 50908 was determined according to U.S EPA guidance document OPPTS 830.7550 "Partition Coefficient (n-Octanol/Water), Shake Flask Method".

Quadruplet test vessels of three different volume ratios (1:1, 1:2, and 2:1) of MTDID 50908 dosed n-octanol  to water were prepared. Ratio 1:1 was prepared a second time on a separate day due to octanol phase contamination in the water phase, resulting total of 8 vials. The samples were rotated 180 ° about their transverse axis for 100 rotations over a period of five minutes to ensure proper mixing of the test system solvents. The samples were then centrifuged at 1000 RPM for at least 30 minutes to ensure a visibly clear separation of layers, prior to removing n-octanol and the aqueous sample analysis aliquots. The n-octanol aliquot were removed first and diluted with methanol. After the n-octanol aliquot removal, the water aliquot were removed and analyzed directly. All samples were analyzed using purge and trap gas chromatography/mass spectrometry (GC/MS).

MTDID 50908 is a multi-constituent substance. The partitioning coefficients were determined based on measured concentrations in n-octanol and water phase for the compounds identified as Component A and Component H, Component B, Component D, Component F. The average measured log Kow for Component A and H is 6.14 (RSD=0.72%), the average measured log Kow for Component B is > 6.49 (RSD=2.01%), the average measured log Kow for Component D is 5.46 (RSD=1.08%), and the average measured log Kow for Component F is > 6.44 (RSD=2.71%).

This is a guideline study conducted under ISO17025. The log Kow are reported for the primary components listed in the composition and are limit values only. Therefore, it is considered reliable with restriction and a key study. This study is pertinent to the fate of MTDID 50908 and may be used for Risk Assessment, Classification & Labelling, and PBT Analysis.

Cross-reference 2

Reason / purpose for cross-reference:

reference to other study

Reference

Endpoint:

Henry's law constant

Type of information:

read-across based on grouping of substances (category approach)

Adequacy of study:

key study

Study period:

2018

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Remarks:

Data from valid studies under GLP

Justification for type of information:

MTDID 50908 is a member of the Perfluorinated Organic Chemicals, C5-C18, category. It consists predominantly of a mixture of C7-C9 perfluorinated tertiary amines, with variety of minor impurities that are also within the category definition and are considered to be category members.  All of these chemicals stem from the same manufacturing process, have similar physicochemical properties including high vapor pressure and low water solubility relative to the hydrocarbon analogs (e.g., hexanes v. perfluorohexanes), and also lack any chemically reactive groups, which forms the technical basis for the category.  Members of this category are fully fluorinated, meaning that fluorine, rather than hydrogen, is bonded to all carbon atoms in the molecule.  Fluorine is the most electronegative of the elements (fluorine has an electronegativity of 3.98 on the Pauling scale, as compared to 2.55 for carbon, 3.04 for nitrogen or 2.20 for hydrogen).  This electronegativity is expected to dominate over all other aspects of substance chemistry and is the underlying basis for similarity of substances in this category.  For example, strong electron withdrawing in perfluorinated tertiary amines results in a molecule with essentially no lone pair influence, and which has chemistry more similar to a branched, perfluorinated alkane than any other structure.  Because these substances exhibit similar physicochemical properties they can be considered to constitute a chemical category.  The data gap for HLC can therefore be addressed by many-to-one read-across between category members.

Qualifier:

according to guideline

Guideline:

other: REACH Guidance on QSARs and grouping of chemicals

Version / remarks:

May/July 2008

Deviations:

no

GLP compliance:

no

Remarks:

Source data were GLP compliant

Specific details on test material used for the study:

Readacross is from category members:
Perfluoroheptanes, PFHp, CAS# 1064698-16-3
Perfluorotripropylamine, PTPA, CAS# 338-83-0
Perfluorotributyl amines, PTBA, CAS# 1064698-37-8
Perfluoro-N-C1,3-alkyl morpholines, FC-770, CAS# 1093615-61-2

Key result

H:

ca. 3 400 - ca. 4 020 atm m³/mol

Temp.:

22 °C

Remarks on result:

other: lower limit defined by perfluoroheptanes, upper limit by perfluorotributyl amines

H:

ca. 1 030 atm m³/mol

Temp.:

22 °C

Remarks on result:

other: data for category member FC-770

Remarks:

Major constituent is an impurity of MTDID 50908

Experimental HLC data are not available for major constituents of MTDID 50908. Readacross by bracketting using other category members was therefore used to establish a range for HLC of MTDID 50908. Among category members PFHp and PTBA best bracket MTDID 50908 with regard to molecular weight range, vapor pressure, water solubility, and log Kow. In addition, PTBA is a perfluorinated tertiary amine, with PFHp as a perfluorinated alkane representing the perfluoroalkyl side-chains of the amines. The HLC values for these two category members were therefore used to establish upper and lower bounds for the major constituents of MTDID 50908.

An impurity of MTDID 50908, 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)morpholine, is the predominant constituent of the category member Perfluoro-N-C1,3-alkyl morpholines (FC-770), CAS# 1093615-61-2. Physical-chemical data for FC-770 indicate that it is considerably more water soluble than the perfluorinated tertiary amines which are the predominant constituents of MTDID 50908. The HLC of FC-770 is not therefore not representative of the predominant constituents. However, it may be used to provide an indication of the HLC for the more-soluble minor impurities found in MTDID 50908.

Conclusions:

Henry's Law constant of MTDID 50908: 3400 – 4020 atm∙m³/mol at 22 °C for predominant components, by readacross from category members. Minor impurities with higher solubility are expected to have lower HLC values (ca. 1030 atm∙m³/mol at 22 °C)

Executive summary:

The Henry’s Law constant (HLC) for MTDID 50908 was determined using a category approach wherein the experimental HLCs of two category members with similar function groups and bracketting physical properties are used to define the upper and lower bound of the HLC range.  The resulting HLC range is 3400 – 4020 atm∙m³/mol at 22 °C.  HLC data for a more soluble category member, the predominant component of which is as an impurity of MTDID 50908, suggests a somewhat lower volatility for the more soluble, minor impurities (ca. 1030 atm∙m³/mol at 22 °C). This approach is considered reliable based on the validity of the experimental values provided. Based on the anticipated HLC range, the test substance is not expected to remain in aqueous solution in open systems and it will partition to the atmosphere.

The validity of this approach to categorically group these types of substances was determined to be reliable with restrictions based on the similarity of chemical functional groups, molecular weights, water solubilities, and vapor pressures. The source data are from GLP-compliant studies which used scientifically acceptable methods, and they are considered reliable. This study is pertinent to the fate of MTDID 50908 and may be used for risk assessment, classification and labelling, and PBT analysis.

Data source

Reference

Reference Type:

other: Calculated values

Title:

Unnamed

Year:

2018

Report date:

2018

Materials and methods

Test guideline

Qualifier:

no guideline available

Principles of method if other than guideline:

Accepted equation for calculation of octanol-air partition coefficient.

GLP compliance:

no

Remarks:

Source data collected under GLP or ISO 17025

Type of study:

volatility

Media:

air - biota

Test material

Test material information

Constituent 1

Reference substance name:

Reaction mass of 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(pentafluoroethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(trifluoromethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N,N-bis(heptafluoropropyl)propan-1-amine

EC Number:

920-778-3

Cas Number:

2176446-38-9

Molecular formula:

constituents: CnF(2n+3)N with n= 7-9

IUPAC Name:

Reaction mass of 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(pentafluoroethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(trifluoromethyl)propan-1-amine and 1,1,2,2,3,3,3-heptafluoro-N,N-bis(heptafluoropropyl)propan-1-amine

Test material form:

liquid

Details on test material:

- Name of test material (as cited in study report): MTDID 50908
- Physical state: Colourless liquid
- Storage condition of test material: At room temperature

Specific details on test material used for the study:

Calculation is done using data obtained by read across from category member:
Perfluoroheptanes, PFHp, CAS# 1064698-16-3
Perfluorotributyl amines, PTBA, CAS# 1064698-37-8
Perfluoro-N-C1,3-alkyl morpholines, FC-770, CAS# 1093615-61-2

Results and discussion

Any other information on results incl. tables

Constituent	Kow	Kaw	Koa	Log Koa
MTDID 50908	For range, see below	Range, 140000 to 166000	─	─
“Components A&H” Unresolved isomeric mixture of Constituent: 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(trifluoromethyl)propan-1-amine and Impurity: 1,1,2,2,3,3,3-heptafluoro-N-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-(trifluoromethyl)propan-1-amine	1380000	140000	9.86	0.99
“Component B” Constituent: 1,1,2,2,3,3,3-heptafluoro-N-(heptafluoropropyl)-N-(pentafluoroethyl)propan-1-amine	>3090000	140000	NC¹	NC
“Component F” Constituent: 1,1,2,2,3,3,3-heptafluoro-N,N-bis(heptafluoropropyl)propan-1-amine	>2770000	140000	NC	NC
“Component D” Impurity: 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(trifluoromethyl)butan-1-amine	289000	140000	2.06	0.31
Impurity: 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,1,2,3,3,3-heptafluroropropan-2-yl)morpholine (readacross from category member FC-770)	488000	42400	11.5	1.06

1. NC, Not calculated

Applicant's summary and conclusion

Conclusions:

The log Koa values of constituents of MTDID 50908 are < 1.1. Minor impurities with higher solubility are expected to be at the high end of this range.

Executive summary:

The octanol and air partition coefficient (Koa) for constituents and impurities of MTDID 50908 was calculated from experimental dimensionless Henry’s Law constants and experimental Kow values using the simple relationship: Koa = Kow/Kaw. The calculatable log Koa values range from 0.31 to 1.06. The highest value, 1.06, was for a more soluble category member, the predominant component of which is as an impurity of MTDID 50908. This suggests that the other more-soluble, minor impurities will be similarly volatile.

The Koa range was calculated according to an accepted formula using data from GLP- or ISO 17025-compliant guidelines studies. The calculation results are reliable with restrictions and suitable for use in Risk Assessment, Classification & Labelling, and PBT Analysis.