13c-labelled chlorinated paraffins and their preparation

A process for preparing a compound of 13C-labelled or unlabelled chlorinated paraffins, preferably having neither geminal nor terminal chlorine atoms in their structure, by converting an unsaturated fatty acid or a mixture of unsaturated fatty acids to a 13C-labelled or unlabelled chlorinated paraffin or a mixture of 13C-labelled or unlabelled chlorinated paraffins, comprising the steps of:

• A) providing a 13C-labelled or unlabelled unsaturated fatty acid or a mixture of 13C-labelled or unlabelled unsaturated fatty acids,
• Ba) chlorinating the unsaturated fatty acid or unsaturated fatty acids and
• Bb) decarboxylating of the resulting chlorinated acid or acids, or
• Ca) converting the unsaturated fatty acid or unsaturated fatty acids to a corresponding alkenol or mixture of alkenols, and
• Cb1) reducing the alkenol or mixture of alkenols to the corresponding alkene or mixture of alkenes, and
• Cb2) chlorinating the resulting alkene or mixture of alkenes;
• or
• Cc1) replacing the alcohol group or groups with a leaving group or groups, preferably tosylate,
• Cc2) coupling an alkyl to the former alcohol carbon, thereby eliminating the leaving group and forming an unsaturated bond, and
• Cc3) chlorinating the resulting alkene or mixture of alkenes;
• or
• Cd) chlorinating the alkenol or mixture of alkenols;
• or
• Da) converting the unsaturated fatty acid or unsaturated fatty acids to a corresponding alkenal or mixture of alkenals, and
• Db1) coupling the alkenal or mixture of alkenals with Wittig salt to form the corresponding alkene or mixture of alkenes,
• Db1a) optionally using Wittig salts with at least one 13C-labelled carbon atom in the coupling group, and
• Db2) chlorinating the resulting alkene or mixture of alkenes.

A compound of 13C-labelled chlorinated paraffins having neither geminal nor terminal chlorine atoms in their structure, the compound further comprising:

• at least two chlorine atoms in their main chain, and
• at least one, particularly from two to eight, carbon atoms of the main chain replaced by 13C-atoms,
• preferably represented by the general formula
• 13Cm-CpH2p+2−xClx,
• with
• m being an integer of from 1 to p, particularly 2 to 8;
• p being an integer of from 2 to 38, preferably from 8 to 38, particularly 8 to 30;
• x=2 to p-2, preferably 4 to p-2, more preferably, in the case of SCCP 4 to 6, particularly 4 or 6, in the case of MCCP 6 to 8, particularly 6 or 8, in the case of LCCP 8 to 10, particularly 8 or 10.