# Analytical Report

This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

### Research, Development & Innovation



# NMR analysis of

G.J.Knoop

Confidential

Analytical documentation MAS A 20140991

- NMR

Trade name(s)

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. ICS-103 

## Project identification

Client 

## Functional Chemicals Client no 

## 1435 Project no
Subclient 

## OP Subclient no Task no 

## 3006134

Drafted by department 

## Measurement & Analytical Science / Molecular Spectroscopy (MAS-SP)

Document number 

## MAS A20140991-NMR

Date 

## February 25, 2015

Author 

## G.J. Knoop Signature

Approved by 

## Dr. S. Datta

Function 

## Project Leader Signature

Distribution 

## B. Weuste

Others 

## A. Talma, B. Fischer, M. Schuur Department archive Central file

Test facility 

## Akzo Nobel Chemicals bv

Research, Development& Innovation Measurement & Analytical Science

Laboratory notebook 

## Raw data files:DVTN23.d20.intra GROUPS R:\CAP\SP\REACH-Polymer

Chemicals\20140409

Keywords 

## analytical report, NMR, 1,2,4,5,7,8-Hexoxonane, 3,6,9-trimethyl-, 3,6,9-tris(Ethyl and

Propyl) derivatives

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

## Table of Contents
2 List of Symbols and Abbreviations 4
3 Objective of the analysis 4
4 Experimental 5 4.1 Test Substance 5 4.2 Test period or test date 5 4.3 Test conditions 5 4.4 Sample preparation 6 4.5 Calibration 6 4.6 Processing and spectral interpretation 6
5 Results 7
6 Conclusions 8
7 Documents and references 8
8 Appendix 9 8.1

14

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

## 2 List of Symbols and Abbreviations
RD&I Research, Development & Innovation ECG Expert Capability Group MAS Measurement & Analytical Science NMR Nuclear Magnetic Resonance MHz Mega Hertz
1 

## H Proton
13 

## C{ 1 

## H} Proton decoupled carbon
s Singlet d Doublet t Triplet q Quartet

m Multiplet % m/m % mass/mass
s R 

## standard deviation under reproducibility conditions
n.a. not applicable CDCl 3 

## Deuterated chloroform

3 Objective of the analysis The objective of the analysis is to identify the test substance 1,2,4,5,7,8-Hexoxonane, 3,6,9-trimethyl-, 3,6,9-tris(Ethyl and Propyl) derivatives, batch BYK04856-98 (final) by Nuclear Magnetic Resonance spectroscopy.

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

## 4 Experimental
4.1 Test Substance

Trade name Chemical description

derivatives EC name Not available EC number Not available CAS number Batch number BYK04856-98 (final) Molecular structure Not available Molecular formula Not available Molecular weight Not available Description Colorless liquid 

## Smiles notation Not available InChI code Not available Storage requirements Keep away from food, drink and animal feeding stuffs. Store in a dry well ventilated place away from sources of heat and direct sunlight. Store separate from other chemicals. Keep only in the original container. Keep container upright to prevent leakage. Do not store in LDPE packages. HDPE is the preferred packaging material. For maximum quality store below: 40 °C. Expiration date April 1, 2024

4.2 Test period or test date
The spectra were recorded in June 2014.

4.3 Test conditions
The spectra are recorded on a Bruker Avance-III 600MHz spectrometer with a proton resonance frequency of 600MHz and a carbon resonance frequency of 150MHz. If conditions are used other than mentioned below, those are shown on the spectra.

Table 4.1 Standard NMR conditions and Experimental conditions for NMR 1 

## H

- NMR 13 

## C

- NMR Probe 5mm BBO ATM probe and z-gradient feature Operating temperature 300 Kelvin Operating frequency 600 MHz 150 MHz Relaxation delay 5 sec. 2 sec. Pulse 30 degrees 30 degrees Acquisition time 2.66 sec. 0.91 sec. Power -15.92dB -19.29dB Spectrum width 12335 Hz 36057 Hz

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 1 

## H

- NMR 13 

## C

- NMR Number of scans 64 1024 Line broadening 0.3 Hz 3 Hz Tube type 5mm disposable NMR tube for Bruker SampleJet

4.4 Sample preparation

The test substance is dissolved in CDCl 3 

## and analyzed with 1 

## H-and 13 

## C-NMR. The 1 

## H-NMR and 13 

## C{ 1 

## H} NMR spectra are recorded of the sample without internal standard.

Table 4.2 Used chemicals and solutions Solvent Formula Supplier CAS number
Deuterated chloroform CDCl 3 

## Aldrich 99.8 % D + 0.03 v/v % TMS 865-49-6
Spirdane D60

- Total 64742-48-9

4.5 Calibration
The proton NMR spectra are calibrated using the TMS present in the NMR solvent at 0.0 ppm. The carbon NMR spectra are calibrated using the CDCl 3 

## solvent peak at 77.0 ppm.

4.6 Processing and spectral interpretation
Spectral interpretation is based on data measured in the same solvent of reference compounds which are stored in the RD&I "ARDD database" and with software prediction with ACDlabs v12 [1].

Table 4.3 NMR experiments Experiment Sample solution Appendix 1 

## H 150.8 mg in 2478.4 mg CDCl 3 

## 8.1, 8.2 13 

## C{ 1 

## H} 364.7 mg in 2457.5mg CDCl 3 

## 8.3, 8.4

1 

## H 150.8 mg in 2478.4 mg CDCl 3 

## & 164.2mg Spirdane D60 reference in 2736.2 mg CDCl 3 

## 9.5

13 

## C{ 1 

## H} 364.7 mg in 2457.5mg CDCl 3 

## & 164.2mg Spirdane D60 reference in 2736.2 mg CDCl 3 

## 9.6

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## 5 Results
5.1.1 Main compound
The identity of the test sample is confirmed by the NMR spectra. The chemical shifts of the main compounds are listed in Table 6.1. The characteristic parts of the molecular structure are shown in Scheme 1. The NMR spectra are given in Appendix 8.

Scheme 1:

The assignment of the different proton and carbon atoms is listed in Table 5.1.

Table 5.1 NMR assignment for the test substance

5.1.2 Additives

An additive is detected with NMR. These additives are identified and the chemical shifts of the detected signals are listed in Table 5.2.

Table 5.2 NMR assignment of additives in the test substance Component Atom
no. 1 

## H

- NMR

Chemical shift 13 

## C

- NMR

Chemical shift
1 1.35 18.1

2 1.85 27.0 – 26.7

3 0.9 8.3

4 1.35 18.7

5 1.85 36.3 – 36.6

6 1.6 17.4

7 0.9 14.3

Component Atom
no. 1 

## H

- NMR Chemical shift 13 

## C-NMR

Chemical shift Spirdane D60 See spectra

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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## 6 Conclusions

7 Documents and references [1] ACDlabs v12, HNMR and CNMR prediction software with own user-database

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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## 8 Appendix
8.1 1 

## H-NMR spectrum of

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm Batch no. BYK04856-98 (final) 150.8 mg sample + 2478.4 mg CDCl3CHCl3TMS Spirdane D60 

### REACH test substance 

### Test substance

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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## 8.2 Expanded 1 

## H-NMR spectrum of

4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm Expanded 600MHz H

- NMR spectrum of REACH test substance Batch no. BYK04856-98 (final) 150.8 mg sample + 2478.4 mg CDCl3TMS Spirdane D60 

### REACH test substance 3,7

2,5 1,4

6 

### Test substance

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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## 8.3 13 

## C{ 1 

## H}-NMR spectrum of

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm8.3214.0914.1414.2814.3114.3917.3917.4118.1418.7022.7226.7226.7526.9626.9929.4129.7129.7531.9777.00109.17109.24109.32109.61109.66109.69109.71CDCl3 Batch no. BYK04856

- 98 (final) 364.7 mg sample + 2457.5 mg CDCl3

O C C

C O O O

Spirdane D60 

### REACH test substance 

### Test substance

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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## 8.4 Expanded 13 

## C{ 1 

## H}-NMR spectrum of

Batch no. BYK04856-98 (final) 364.7 mg sample + 2457.5 mg CDCl3

55 50 45 40 35 30 25 20 15 10 5 ppm8.288.3214.0914.1414.2814.3114.3917.3917.4118.1418.7022.7226.7226.7526.9626.9929.4129.7129.7531.97



### REACH test substance

Spirdane D60-CH3MEKP-CH3MPKP-CH3MPKP-CH2MPKP-CH2MEKP-CH3MEKP-CH2MPKP O C C H 3 1

C H 2 2 O O O

C H 3

3 O C C H 3 4

C H 2 5 O O O

C H 2

6

C H 3 7 

### 3 1

2

7 5 6 4 

### Test substance

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

## 8.5 1 

## H-NMR spectra of

### ICS-103 Analytical Report MAS A20140991-NMR February 25, 2015

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This report is property of Akzo Nobel NV or its affiliated companies. All rights are strictly reserved. Reproduction, issue or disclosure to third parties in any form is not permitted without previously written authorization from the proprietor. 

## 8.6 13 

## C-NMR spectra of