Dicarboxylic acid diesters

Patent metadata

Field	Value
Publication number	US-11987539-B2
Application number	US-201917047883-A
Country	US
Kind code	B2
Filing date	Apr 23, 2019
Priority date	Apr 25, 2018
Publication date	May 21, 2024
Grant date	May 21, 2024

Abstract

The present invention relates to novel dicarboxylic diesters as well as the use thereof as for inhibiting the methane production in ruminants.

First claim

The invention claimed is:

1. A dicarboxylic acid diester of formula (I):

wherein
n is 3, and
X is a C 1 alkylene.

2. A process for the preparation of the dicarboxylic diester according to claim 1 , wherein the process comprises a step of reacting a dicarboxylic acid of formula (II) with a nitrooxyalcohol of formula (III):

wherein n and X are as defined in claim 1 .

3. A process for the preparation of the dicarboxylic diester according to claim 1 , wherein the process comprises reacting a fatty acid of formula (II) with an alcohol of formula (IV) to obtain a fatty acid monoester of formula (V), followed by reacting the fatty acid monoester of formula (V) with nitrosulfuric acid:

wherein n and X are as defined in claim 1 .

4. A feed composition or feed additive comprising the dicarboxylic diester of formula (I) according to claim 1 .

5. The feed composition according to claim 4 , wherein the feed composition is a mineral premix, a vitamin premix, a premix comprising vitamins and minerals or a bolus.

6. A method for reducing the production of methane emanating from the digestive activities of ruminants and/or for improving ruminant animal performance comprising the oral administration of a sufficient amount of the dicarboxylic diester of formula (I) according to claim 1 to the animal.

7. The method according to claim 6 , wherein the amount of the dicarboxylic diester of formula (I) administered to the ruminant animal is from 1 mg to 10 g per kg feed.

8. The method according to claim 6 , wherein the methane production in ruminants is calculated in liters per kilogram of dry matter intake and wherein the amount of the dicarboxylic diester of formula (I) is administered to reduce the methane production of the ruminant animal by at least 10% when measured in metabolic chambers.

9. The method according to claim 6 , wherein the ruminant animal is selected from the group consisting of cattle, goats, sheep, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and nilgai.

Assignees

• Dsm Ip Assets Bv

Inventors

• Laeuger Stefan Karl
• Letinois Ulla
• Riebel Peter

Classifications

• C07C203/04 Primary

  having nitrate groups bound to acyclic carbon atoms · CPC title

• A23K20/105

  Aliphatic or alicyclic compounds · CPC title

• A23K20/158

  Fatty acids; Fats; Products containing oils or fats · CPC title

• A23K50/10

  for ruminants · CPC title

• C11C3/04

  by esterification of fats or fatty oils · CPC title