Dicarboxylic acid diesters

Patent metadata

Field	Value
Publication number	US-12497347-B2
Application number	US-202418597843-A
Country	US
Kind code	B2
Filing date	Mar 6, 2024
Priority date	Apr 25, 2018
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

Dicarboxylic diesters are disclosed having the formula (I):

wherein n is 3, and X is a C 2 alkylene or a C 2 alkenylene group. Such dicarboxylic diesters are useful 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 2 alkenylene group.

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 each of n and X is as defined previously.

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 each of n and X is as defined previously.

4 . A feed composition comprising a dicarboxylic diester which is bis(3-(nitrooxy)propyl) fumarate.

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

6 . A method for reducing the production of methane emanating from the digestive activities of a ruminant animal and/or for improving ruminant animal performance comprising orally administering the feed composition according to claim 4 so as to achieve an amount of the dicarboxylic diester administered to the animal which is sufficient to reduce production of methane emanating from the digestive activities of the ruminant animal and/or improve the ruminant animal performance.

7 . The method according to claim 6 , wherein the amount of the dicarboxylic diester 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 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.

10 . 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.

11 . The method according to claim 10 , 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.

12 . The method according to claim 10 , 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.

13 . The method according to claim 10 , 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

• A23K20/105

  Aliphatic or alicyclic compounds · CPC title

• A23K50/10

  for ruminants · CPC title

• A23K20/158

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

• Y02P60/22

  Methane [CH4], e.g. from rice paddies · CPC title

• C11C3/04

  by esterification of fats or fatty oils · CPC title