EP4634138A1 - New method for sustainable manure management - Google Patents

New method for sustainable manure management

Info

Publication number
EP4634138A1
EP4634138A1 EP23821648.5A EP23821648A EP4634138A1 EP 4634138 A1 EP4634138 A1 EP 4634138A1 EP 23821648 A EP23821648 A EP 23821648A EP 4634138 A1 EP4634138 A1 EP 4634138A1
Authority
EP
European Patent Office
Prior art keywords
nitrooxy
manure
comprised
animal
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23821648.5A
Other languages
German (de)
French (fr)
Inventor
Stephane Duval
Pauline JENN
Ursula MCCORMACK
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Publication of EP4634138A1 publication Critical patent/EP4634138A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
    • C05F3/00—Fertilisers from human or animal excrements, e.g. manure
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C3/00—Treating manure; Manuring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel

Definitions

  • Methane is the most abundant organic chemical in the earth’s atmosphere, and its abundance is increasing with time and has reached levels not seen in recent geological history. Methane is produced both naturally and anthropogenically. One of the sources of anthropogenic methane is manure from domesticated animal.
  • Nitrooxy organic molecules are very efficient in reducing methane emissions from manure originating from livestock production.
  • Nitrooxy organic molecules as described below are very efficient in reducing methane emissions from manure management systems, they provide a persistent methane reduction, and are safe for the environment as well as for human.
  • Manure management system means any way/system of managing the manure originating from livestock production. It refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner. It can be retained in various holding facilities (for example swine pits). Animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. It is utilized by distribution on fields in amounts that enrich soils without causing water pollution or unacceptably high levels of nutrient enrichment. Manure management is a component of nutrient management.
  • the term “animal” in connection with the present invention refers to any farm animal.
  • farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
  • the problem to be solved by the present invention is to provide a method to reduce methane emissions from the manure generated by livestock production systems.
  • the present inventors now surprisingly found that the compounds specified herein after, have a great potential for use in livestock manure management in order to reduce the formation of methane without affecting the environment. Said compounds are also more stable than those described in the prior art, safer for the environment and human using it, lead to persistent methane reduction effect, they do not affect the overall manure management systems, they can be produced at industrial scale at a cost compatible with the agrochemical industry, and they are active at very low concentration.
  • the present invention provides the use of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) as an active compound for reducing the formation of methane emanating from livestock manure management systems.
  • the invention further provides a method for reducing the production of methane emanating from the livestock manure management systems, comprising applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system.
  • organic molecules substituted at any position with at least one nitrooxy group, or salts thereof are defined by the following compound of formula (I)
  • Y is an organic molecule of the following composition: C a HbOdN e S g , wherein a is comprised between 1 and 25, preferably between 1 and 10 b is comprised between 2 and 51 , preferably between 2 and 21 d is comprised between 0 and 8, preferably between 0 and 6 e is comprised between 0 and 5, preferably between 0 and 3 g is comprised between 0 and 3, preferably between 0 and 1.
  • preferred compounds of formula (I) according to the present invention are compounds, wherein a is comprised between 1 and 10, preferably, a is comprised between 3 and 8.
  • preferred compounds of formula (I) are compounds of formula (II), formula (II), wherein n is comprised between 0 and 12, preferably comprised between 0 and 6 and, wherein, if n 0, the carbon chain is a linear, a cyclic, or branched aliphatic carbon chain which may be non-substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, or an alkenyl, or an alkynyl carbon chain mono- or polyunsaturated and in any isomeric form,
  • R4 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 12, preferably 1 to 6 carbon atoms,
  • X is hydrogen, R5, R5 N, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, - CONR5R6, -NHSO2R5, or -SO2NHR5,
  • R5 and R6 are independently, hydrogen, C1 -C12 straight, branched or cyclic alkyl chain, non substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, alkenyl, or alkynyl carbon chain which may be mono or polyunsaturated, and in any isomeric form.
  • the carbon chain when n > 2, can be linear or branched at any position along the carbon chain. In addition, the carbon chain can be branched by multiple branches at different positions along the carbon chain. Moreover, when n > 3, the aliphatic carbon chain may form a cyclic moiety. This cyclic moiety can carry the nitrooxy moiety at any position (2, 3, 4), and it can also be branched at multiple positions by any aliphatic groups. The branched aliphatic groups are preferably, methyl, ethyl or propyl. Moreover, the carbon chain may be further substituted with up to 3 hydroxyl- , alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups.
  • a preferred alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, cyclohexyl, and 2-ethyl-hexyl and octyl.
  • any alkyl or alkenyl group containing three or more carbon atoms can be straight chain, branched, or cyclic.
  • more preferred compounds of formula (I) according to the present invention are selected from the list of compounds, and salts thereof comprising: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy-propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3-Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis-Nitrooxybutane, 1 ,5-bis- Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3-Nitrooxy-propyl hexanoate, 3- Nitrooxy-propyl 5-nitrooxy-hexanoate, Benz
  • the nitrooxy organic molecule is preferably applied as an agrochemical composition further comprising an agrochemical adjuvant.
  • a preferred nitrooxy organic compound is 3 Nitrooxypropanol (CAS-No: 100502-66-7). It is a known compound which can e.g. be manufactured as outlined in WO-2004043898 or WO-2012084629. Suitable formulations thereof are e.g. disclosed in WO-2018149755, WO-2018149756, WO-2018091643 or WO- 2019007740.
  • the nitrooxyorgan ic compound can be administered once or in regular intervals to the slurry or manure of the farm animals. More preferably, the administration of the nitrooxyorgan ic compound is such that it reaches a concentration of between 10 and 2000 mg nitrooxy organic compound / kg animal manure or slurry.
  • Methane concentration can be measured from manure by standard methods.
  • Swine pit has been treated with 3 Nitrooxypropanol formulated as described in WO-2018149755.
  • the nitrooxy organic compound has been administered such that it reaches a concentration of 500, 1000 and 2000 mg nitrooxy organic compound / kg animal slurry.
  • Methane concentration in the slurry i.e. methane production of the slurry, has been measured over a period of about 120 hours and compered with untreated slurry.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatment Of Sludge (AREA)

Abstract

The present invention relates to a method to reduce emissions of methane originating from the manure management of livestock production. More particularly, it relates to the use of a nitrooxy organic compound to reduce methane emission from livestock manure, in particular from swine manure slurry.

Description

NEW METHOD FOR SUSTAINABLE MANURE MANAGEMENT
Technical Field
The present invention relates to a method to reduce emissions of methane originating from the manure management of livestock production. More particularly, it relates to the use of a nitrooxy organic compound to reduce methane emission from livestock manure.
Background of the invention
Methane is the most abundant organic chemical in the earth’s atmosphere, and its abundance is increasing with time and has reached levels not seen in recent geological history. Methane is produced both naturally and anthropogenically. One of the sources of anthropogenic methane is manure from domesticated animal.
Thus, in view of the greenhouse gas global warming challenge, there is an urgent need to find new solutions to significantly reduce methane emissions from the manure generated by livestock production. The present inventors surprisingly found that Nitrooxy organic molecules are very efficient in reducing methane emissions from manure originating from livestock production. Thus Nitrooxy organic molecules as described below are very efficient in reducing methane emissions from manure management systems, they provide a persistent methane reduction, and are safe for the environment as well as for human.
“Manure management system” means any way/system of managing the manure originating from livestock production. It refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner. It can be retained in various holding facilities (for example swine pits). Animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. It is utilized by distribution on fields in amounts that enrich soils without causing water pollution or unacceptably high levels of nutrient enrichment. Manure management is a component of nutrient management. The term “animal” in connection with the present invention refers to any farm animal. Examples of farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
Summary of the invention
Therefore, the problem to be solved by the present invention is to provide a method to reduce methane emissions from the manure generated by livestock production systems.
Further aspects of the invention are subject of further independent claims. Particularly preferred embodiments are subject of dependent claims.
Detailed description of the invention
The present inventors now surprisingly found that the compounds specified herein after, have a great potential for use in livestock manure management in order to reduce the formation of methane without affecting the environment. Said compounds are also more stable than those described in the prior art, safer for the environment and human using it, lead to persistent methane reduction effect, they do not affect the overall manure management systems, they can be produced at industrial scale at a cost compatible with the agrochemical industry, and they are active at very low concentration.
Therefore, the present invention provides the use of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) as an active compound for reducing the formation of methane emanating from livestock manure management systems.
The invention further provides a method for reducing the production of methane emanating from the livestock manure management systems, comprising applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system.
In all embodiments of the present invention, organic molecules substituted at any position with at least one nitrooxy group, or salts thereof are defined by the following compound of formula (I)
O2N._Y u formula (I) wherein Y is an organic molecule of the following composition: CaHbOdNeSg, wherein a is comprised between 1 and 25, preferably between 1 and 10 b is comprised between 2 and 51 , preferably between 2 and 21 d is comprised between 0 and 8, preferably between 0 and 6 e is comprised between 0 and 5, preferably between 0 and 3 g is comprised between 0 and 3, preferably between 0 and 1.
In another embodiment, preferred compounds of formula (I) according to the present invention are compounds, wherein a is comprised between 1 and 10, preferably, a is comprised between 3 and 8.
In another embodiment, preferred compounds of formula (I) according to the present invention are compounds of formula (II), formula (II), wherein n is comprised between 0 and 12, preferably comprised between 0 and 6 and, wherein, if n 0, the carbon chain is a linear, a cyclic, or branched aliphatic carbon chain which may be non-substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, or an alkenyl, or an alkynyl carbon chain mono- or polyunsaturated and in any isomeric form,
R4 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 12, preferably 1 to 6 carbon atoms,
X is hydrogen, R5, R5 N, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, - CONR5R6, -NHSO2R5, or -SO2NHR5,
R5 and R6 are independently, hydrogen, C1 -C12 straight, branched or cyclic alkyl chain, non substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, alkenyl, or alkynyl carbon chain which may be mono or polyunsaturated, and in any isomeric form.
For all embodiments of the present invention, it is to be understood that compounds of formula (I) and compounds of formula (II) can be in any isomeric form.
It is to be understood in the above definition of compounds of formula (II) that when n > 2, the carbon chain can be linear or branched at any position along the carbon chain. In addition, the carbon chain can be branched by multiple branches at different positions along the carbon chain. Moreover, when n > 3, the aliphatic carbon chain may form a cyclic moiety. This cyclic moiety can carry the nitrooxy moiety at any position (2, 3, 4), and it can also be branched at multiple positions by any aliphatic groups. The branched aliphatic groups are preferably, methyl, ethyl or propyl. Moreover, the carbon chain may be further substituted with up to 3 hydroxyl- , alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups.
In the above definition of derivatives of the formula (II) a preferred alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, cyclohexyl, and 2-ethyl-hexyl and octyl. Furthermore any alkyl or alkenyl group containing three or more carbon atoms can be straight chain, branched, or cyclic. In addition for the straight chain or branched C2-C -alkenylene group, this is understood to encompass alkenylene groups with one or (from C4) more double bonds; examples of such alkenylene groups are those of the formulae -CH=CH-, - CH=CH-CH2-, -CH=CH-(CH2)3- and -(CH=CH)2-.
In another embodiment, more preferred compounds of formula (I) according to the present invention are selected from the list of compounds, and salts thereof comprising: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy-propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3-Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis-Nitrooxybutane, 1 ,5-bis- Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3-Nitrooxy-propyl hexanoate, 3- Nitrooxy-propyl 5-nitrooxy-hexanoate, Benzylnitrate, isosorbid-dinitrate, and N-[2- (Nitrooxy)ethyl]-3-pyridinecarboxamide, 2-Nitro-5-nitrooxymethyl-furan, and Bis-(2- nitrooxyethyl) ether as listed in Table 1 :
Table 1 : Preferred compounds of formula (I) according to the present invention
The nitrooxy organic molecule is preferably applied as an agrochemical composition further comprising an agrochemical adjuvant. A preferred nitrooxy organic compound is 3 Nitrooxypropanol (CAS-No: 100502-66-7). It is a known compound which can e.g. be manufactured as outlined in WO-2004043898 or WO-2012084629. Suitable formulations thereof are e.g. disclosed in WO-2018149755, WO-2018149756, WO-2018091643 or WO- 2019007740.
The nitrooxyorgan ic compound can be administered once or in regular intervals to the slurry or manure of the farm animals. More preferably, the administration of the nitrooxyorgan ic compound is such that it reaches a concentration of between 10 and 2000 mg nitrooxy organic compound / kg animal manure or slurry.
Methane concentration can be measured from manure by standard methods.
Example
Treatment of slurry in Swin pit with 3 Nitrooxypropanol
Swine pit has been treated with 3 Nitrooxypropanol formulated as described in WO-2018149755. In three parallel test series, the nitrooxy organic compound has been administered such that it reaches a concentration of 500, 1000 and 2000 mg nitrooxy organic compound / kg animal slurry.
Methane concentration in the slurry, i.e. methane production of the slurry, has been measured over a period of about 120 hours and compered with untreated slurry.
The results (Figure 1 ) show a clear response that the treatment of animal manure with a nitrooxy organic compound according to the invention decreases methane product and thus provides a significant reduction of methane emissions from manure management systems (swine pit).

Claims

Claims
1 . Method for reducing the production of methane emanating from livestock manure management systems, comprising applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system, formula (I), wherein Y is an organic molecule of the following composition: CaHbOdNeSg, wherein a is comprised between 1 and 25, b is comprised between 2 and 51 , d is comprised between 0 and 8, e is comprised between 0 and 5, g is comprised between 0 and 3.
2. Method according to claim 1 wherein the at least one organic molecule substituted at any position with at least one nitrooxy group is selected from: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy- propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3- Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis- Nitrooxybutane, 1 ,5-bis-Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3- Nitrooxy-propyl hexanoate, 3-Nitrooxy-propyl 5-nitrooxy-hexanoate, Benzylnitrate, isosorbid-dinitrate, and N-[2-(Nitrooxy)ethyl]-3- pyridinecarboxamide, 2-Nitro-5-nitrooxymethyl-furan, and Bis-(2- nitrooxyethyl) ether. Method according to claim 1 wherein the at least one organic molecule substituted at any position with at least one nitrooxy group is selected from: 3- Nitrooxypropanol. Method according to any of claims 1 to 3, wherein manure management system means any way/system of managing the manure originating from livestock production, it refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner and wherein animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. Method according to any of claims 1 to 4, wherein the term animal refers to any farm animal, examples of farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
EP23821648.5A 2022-12-14 2023-12-11 New method for sustainable manure management Pending EP4634138A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22213514 2022-12-14
PCT/EP2023/085221 WO2024126430A1 (en) 2022-12-14 2023-12-11 New method for sustainable manure management

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EP4634138A1 true EP4634138A1 (en) 2025-10-22

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EP (1) EP4634138A1 (en)
AU (1) AU2023393623A1 (en)
WO (1) WO2024126430A1 (en)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20022410A1 (en) 2002-11-14 2004-05-15 Dinamite Dipharma S P A PROCEDURE FOR THE NITRATION OF ALCANDIOLI.
RU2578485C2 (en) 2010-12-20 2016-03-27 ДСМ АйПи АССЕТС Б.В. Application of nitroxy-organic molecules in forage to reduce release of methane by ruminants and/or to increase productivity in ruminants
AU2017360025B2 (en) 2016-11-18 2022-06-09 Dsm Ip Assets B.V. Powderous formulations
AU2018222468B2 (en) 2017-02-14 2023-05-11 Dsm Ip Assets B.V. Water dispersible formulations
KR102605784B1 (en) 2017-02-14 2023-11-24 디에스엠 아이피 어셋츠 비.브이. Storage-stable formulation
EP3648743B1 (en) 2017-07-07 2022-07-20 DSM IP Assets B.V. Compressed tablets comprising nitrooxy compounds
AU2021309969A1 (en) * 2020-07-15 2023-02-23 Locus Solutions Ipco, Llc Improved methods and compositions for processing manure
CN114632411B (en) * 2022-03-30 2024-10-22 江苏省农业科学院 A method for reducing carbon and nitrogen emissions from urine and feces in pig farms

Also Published As

Publication number Publication date
WO2024126430A1 (en) 2024-06-20
AU2023393623A1 (en) 2025-05-22
WO2024126430A8 (en) 2025-05-30

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