WO2025056580A1 - Utilisation de lactosérum et de mononitrate de propanediol pour réduire l'émission de méthane de ruminants - Google Patents

Utilisation de lactosérum et de mononitrate de propanediol pour réduire l'émission de méthane de ruminants Download PDF

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WO2025056580A1
WO2025056580A1 PCT/EP2024/075316 EP2024075316W WO2025056580A1 WO 2025056580 A1 WO2025056580 A1 WO 2025056580A1 EP 2024075316 W EP2024075316 W EP 2024075316W WO 2025056580 A1 WO2025056580 A1 WO 2025056580A1
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whey
feed
animal
propanediol mononitrate
pdmn
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Isabel MUELLER
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DSM IP Assets BV
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DSM IP Assets BV
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/20—Animal feeding-stuffs from material of animal origin
    • A23K10/26—Animal feeding-stuffs from material of animal origin from waste material, e.g. feathers, bones or skin
    • A23K10/28—Animal feeding-stuffs from material of animal origin from waste material, e.g. feathers, bones or skin from waste dairy products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A23K20/147—Polymeric derivatives, e.g. peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
    • Y02P60/22—Methane [CH4], e.g. from rice paddies

Definitions

  • the present invention relates to the field of reduction of methane emission in ruminants. Particularly, it relates to the administration of whey and propanediol mononitrate to a ruminant for reducing the production of methane emanating from the digestive activities of said ruminant.
  • Whey is the liquid remaining after milk has been curdled and strained. It is a byproduct of the manufacturing of cheese or casein and has several commercial uses. Sweet whey is a byproduct resulting from the manufacture of rennet types of hard cheese, like Cheddar or Swiss cheese. Acid whey (also known as sour whey) is a byproduct brought out during the making of acid types of dairy products, such as strained yogurt.
  • Whey is known as a mildly satiating, low-energy beverage. It consists of about 94% water, 4 to 5% lactose, and contains very little fat. Whey contains many important components: protein (whey protein), a significant amount of vitamin B12, as well as calcium, phosphorus, magnesium, potassium, iron, and zinc. Whey is particularly suitable as a low-energy source of vitamin B12 and has a mild laxative effect.
  • the present invention further relates to animal feed compositions and feed additives comprising propanediol mononitrate and whey as well as the use of said feed composition or feed additives for reducing the production of methane emanating from the digestive activities of ruminants.
  • the temperature of the air surrounding the earth is increasing, a process referred to as global warming.
  • One of the main focuses to reduce this warming effect is to reduce the amount of greenhouse gases emitted into the atmosphere.
  • Greenhouse gases are emitted from several different sources, both natural and artificial; however, the two sources with the most emphasis are the agricultural and fossil fuel industries.
  • ruminants and in particular cattle are the major contributors to the biogenic methane formation, and it has been estimated that the prevention of methane formation from ruminants would almost stabilize atmospheric methane concentrations.
  • Methane emission from the ruminant livestock sector a by-product from enteric fermentation of plant biomass in the ruminant digestive system — is produced by methanogenic archaea.
  • Various attempts have been made in the last decade to mitigate methane production from ruminant animals. Although the approaches vary, the most popular method so far are feed additives which act in the rumen fluid by reducing respectively inhibiting the methane production by methanogenic archaea.
  • Propanediol mononitrate also referred to herein as PDMN or 3-Nitrooxypropanol (3-NOP) having the chemical structure of formula (I) has been reported to significantly reduce the methane production in ruminants (see e.g. WO2012/084629).
  • Whey is a naturally occurring compound of formula (II) formula (II) e.g. found in citrus fruits.
  • the present invention provides the use of whey and propanediol mononitrate for reducing the formation of methane emanating from the digestive activities of ruminants.
  • the invention further provides a method for reducing the production of methane emanating from the digestive activities of ruminants, said method comprising orally administering to the animal an effective amount of whey and propanediol mononitrate.
  • the present invention relates to a (ruminant) feed composition or feed additive comprising whey and propanediol mononitrate.
  • whey and propanediol mononitrate may be administered admixed together (i.e. pre-mixed) or separately to the ruminant, while in the latter case it is well understood that the administration of propanediol mononitrate and whey occurs within a certain time window, i.e. within at most 6 h, preferably within 3 h, more preferably within 1 h, such as within 0.5 h.
  • both ingredients are concomitantly administered to the ruminant e.g. by concomitant addition thereof into the animal’s feed (diet) or into the feed rack.
  • whey and propanediol mononitrate are administered together in form of a feed composition or feed additive comprising whey and propanediol mononitrate.
  • whey and propanediol mononitrate are administered to the ruminant in an effective amount, i.e. in an amount which results in a methane reduction, preferably of at least 10 %, more preferably of at least 20 %, most preferably of at least 30 %, when compared to the control, i.e. to ruminants not supplemented with whey and propanediol mononitrate.
  • the present invention also relates to the (combined) use of whey and propanediol mononitrate, wherein the methane production in ruminants is reduced by at least 10 % when compared to a control (i.e. in the absence of whey and propanediol mononitrate).
  • the methane reduction is at least 15 %, more preferably at least 20 %, even more preferably at least 25 %, most preferably at least 30 %.
  • Propanediol mononitrate [CAS No: 100502-66-7] is a known compound which can e.g. be manufactured as outlined in W02004043898 or WO2012084629 and which is available under the trademark Bovaer® at DSM Nutritional Products Ltd.
  • Whey (herein refers to liquid whey LW) is left over when milk is coagulated during the process of cheese production and contains everything that is soluble from milk after the pH is dropped to 4.6 during the coagulation process. Generally, it is a 5% solution of lactose in water, with some minerals and lactalbumin. The fat is removed and then processed for human foods. Further processing can be done by simple drying, or the relative protein content can be increased by removing lipids and other non-protein materials. For example, spray drying after membrane filtration separates the proteins from whey. This results in either a whey concentrate (CW) or a whey powder (WP).
  • CW whey concentrate
  • WP whey powder
  • Whey is rich in proteins and contains proteins as for example of a-lactalbumin, p-lactoglobu- lin, serum albumin, immunoglobulins, and proteose peptones.
  • the protein fraction in whey constitutes approximately 10% of the total dry solids in whey.
  • This protein is typically a mixture of beta-lactoglobulin (-48-58%), alpha-lactalbumin (-13-19%), bovine serum albumin ( ⁇ 6%)(see also serum albumin), and immunoglobulins.
  • an effective amount refers to an amount necessary to obtain a reduction of the methane emissions resulting from the digestive activities of a ruminant. It is well understood, that said reduction may be achieved by one single (daily) dose or by repeated (daily) doses.
  • the effective amount of whey and propanediol mononitrate in the uses, methods and compositions according to the invention may vary depending upon known factors, such as the characteristics of the particular composition and its mode and route of administration, the whey content of the respective plant product, the age, health and weight of the ruminant, the frequency of treatment, all of which can be determined by the expert in the field with normal trials or with the usual considerations regarding the intake regime and/ or the formulation.
  • the effective amount of propanediol mononitrate to be administered to the ruminants is selected in the range from 0.05 to 5 g PDMN/ animal/ day, more preferably in the range from 0.1 to 4 g PDMN/ animal/ day, most preferably in the range from 0.25 to 3 g PDMN/ animal/ day. Further suitable effective amounts are selected in the range from 0.5 to 3 g PDMN/ animal/ day or from 1 to 3 g PDMN/ animal/ day.
  • the effective amount of propanediol mononitrate in the feed is selected in the range from 10 mg to 300 mg PDMN/ kg DM/ day, more preferably in the range from 25 to 150 g PDMN/ kg DM/ day, most preferably in the range from 50 to 100 g PDMN/ kg DM/ day.
  • Propanediol mononitrate is preferably administered in the form of a powderous formulation thereof.
  • PDMN can also be administered in liquid form, optionally in a mixture with whey or via drinking water.
  • said powderous formulation is a powderous formulation comprising PDMN and a carrier material.
  • Suitable carrier includes any carrier well known in the food and feed industry such as silicone dioxide (silica) without being limited thereto.
  • Powderous formulations comprising PDMN and a carrier material are usually prepared by PDMN being sprayed onto or admixed with the carrier material by standard methods in the art, e.g. by diluting PDMN in an organic solvent suitable for the preparation of food or feed products such as e.g. dichloromethane, spraying or admixing said solution with/ onto the carrier followed by evaporation of the organic solvent.
  • PDMN can be diluted in a suitable edible oil before being sprayed onto or admixed with the carrier material. In the latter cases the respective edible oil is generally not removed.
  • the powderous formulation may in addition contain usual additives used in the preparation of powderous formulations for feed application.
  • the amount of PDMN in the powderous formulation according to the present invention is preferably selected in the range of 1 to 20 wt.-%, preferably in the range of 2 to 15 wt.-%, most preferably in the range of 4 to 12 wt.-%, based on the total weight of the composition.
  • Particularly suitable powderous formulation to be used in all embodiments of the present invention consists essentially of PDMN, propylene glycol and silica as e.g. outlined in WO2018149756 and WO2018149755 and are commercially available as Bovaer® 10 from DSM Nutritional Products Ltd.
  • the whey of the present invention is added to the feed (diet) of the animal in the form of a single feed additive formulation (also referred to herein as whey additive formulation).
  • feed additive formulation refers to liquid whey (LW) or concentrated whey (CW), or a powderous formulation (WP), which can either be added directly into an animal feed (diet) or into an premix.
  • LW liquid whey
  • CW concentrated whey
  • WP powderous formulation
  • propanediol mononitrate and whey are administered in the absence of (i.e. not concomitantly with) any antibiotic.
  • Whey and propanediol mononitrate in all uses and methods according to the present invention are preferably administered concomitantly to the ruminant, either by prior admixing thereof or by separate addition to the diet of the animal.
  • propanediol mononitrate and whey are added to the feed as single (not premixed) ingredients.
  • propanediol mononitrate and whey are added to the feed as premixed ingredients.
  • Whey and propanediol mononitrate are preferably administered via a (ruminant) feed composition or feed additive to the ruminant, e.g. by admixing the individual components with the ruminant’s feed.
  • propanediol mononitrate as well as whey with all the definitions and preferences as given herein are administered to the ruminant incorporated into a (ruminant) feed composition or feed additive.
  • feed composition or feed additive means any preparation, mixture, or composition suitable for, or intended for oral intake by an animal.
  • feed for ruminants such as cows include forage (grass, legumes, silage), hay, grass, grain as well as soy without being limited thereto.
  • Said feed compositions or feed additives may be prepared by methods known per se in the art of feed formulation and processing.
  • feed compositions and feed additives are still novel.
  • further aspects of the present invention are (ruminant) feed compositions and feed additives comprising whey and propanediol mononitrate with all the definitions and preferences as given herein.
  • the feed compositions and feed additives are a mineral premix, a vitamin premix including vitamins and optionally minerals or a bolus.
  • Whey and propanediol mononitrate may be used in combination with conventional ingredients present in an animal feed composition (diet) such as forages (raw, grass, hay, silages), coproducts from industry (citrus pulp, soybean hulls, distillers dried or wet grains with solubles, minerals (calcium carbonates, electrolytes such as ammonium chloride, macro and trace minerals and in all forms, inorganic and organic), proteins such as soya bean meal, sunflower meal, meat and bone meal, fish meal, amino acids and others, energy ingredients such as grains, wheat, starch, barley, millet, sorghum, corn, animal and plants fat or oils, and vitamins without being limited thereto.
  • feed compositions of the invention are the following:
  • An animal feed additive comprising (a) propanediol mononitrate and (b) whey and (c) one or more of (c-1) fat-soluble vitamin(s), (c-2) water-soluble vitamin(s), (c-3) trace mineral(s) and (c-4) macro mineral(s);
  • An animal feed composition comprising (a) propanediol mononitrate and (b) whey and (c) one or more of (c-1) a crude protein content of 50 to 800 g/kg feed (50-80%), (c-2) fat from 5 - 100 g/kg feed (5-10%), (c-3) NDF from 150 - 700 g/kg feed (15-70%), (c-4) TDN from 300 - 800 (30 - 80%) and (c-5) starch from 150 - 700 g/kg feed (15 - 70%).
  • premixes are examples of animal feed additives of the invention.
  • a premix designates a preferably uniform mixture of one or more micro-ingredients with diluents and/or carrier. Premixes are used to facilitate uniform dispersion of micro-ingredients in a larger mix.
  • the premix of the invention preferably contains at least one fat-soluble vitamin, and/or at least one water soluble vitamin, and/or at least one trace mineral, and/or at least one macro mineral.
  • the premix of the invention comprises the propanediol mononitrate and whey together with at least one additional component selected from the group consisting of fatsoluble vitamins, water-soluble vitamins, trace minerals, and macro minerals.
  • the premix comprises whey and propanediol mononitrate with at least one additional component selected from the group consisting of fat-soluble vitamins, water-soluble vitamins, and trace-minerals.
  • fat-soluble vitamins are vitamin A, vitamin D3, vitamin E, and vitamin K, e.g. vitamin K3.
  • water-soluble vitamins are vitamin B12, biotin and choline, vitamin B1 , vitamin B2, vitamin B6, niacin, folic acid and panthothenate, e.g. Ca-D-panthothenate.
  • trace minerals are manganese, zinc, iron, copper, iodine, selenium, manganese, and cobalt.
  • macro minerals are calcium, phosphorus, potassium, magnesium and sodium.
  • feed compositions for ruminants such as cows, as well as ingredients thereof, the ruminant diet is usually composed of an easily degradable fraction (named concentrate) and a fiber-rich less readily degradable fraction (named hay, forage, or roughage).
  • Hay is made of dried grass, legume or whole cereals.
  • Grasses include among others temperate or tropical grasses, timothy, ryegrasses, fescues, brachiaria, panicum, tifton.
  • Legumes include among others clover, lucerne or alfalfa, peas, beans and vetches.
  • Whole cereals include among others barley, maize (corn), oat, wheat, sorghum.
  • Other forage crops include sugarcane, sugarcane bagasse, citrus pulp, kales, rapes, and cabbages.
  • root crops such as turnips, swedes, mangles, fodder beet, and sugar beet (including sugar beet pulp and beet molasses) are used to feed ruminants.
  • tubers such as potatoes, cassava and sweet potato.
  • Silage is an ensiled version of the fiber-rich fraction (e.g. from grasses, legumes or whole cereals) and grains (e.g. high moisture corns silage) whereby material with a high water content is treated with a controlled anaerobic fermentation process (naturally- fermented or additive treated) without being limited thereto.
  • Concentrate feed is largely made up of cereals grains (such as barley including brewers grain and distillers grain, maize, wheat, sorghum), but also often contain protein-rich feed ingredients such as soybean meal, rapeseed meal, palm kernel and sunflower meal without being limited thereto.
  • cereals grains such as barley including brewers grain and distillers grain, maize, wheat, sorghum
  • protein-rich feed ingredients such as soybean meal, rapeseed meal, palm kernel and sunflower meal without being limited thereto.
  • Ruminants males, females and in all growth stages and adults may also be fed total mixed rations (TMR), where all the dietary components, e.g. forage, silage, other feed ingredients and concentrate, are mixed before serving.
  • TMR total mixed rations
  • a premix is an example of a feed additive which may comprise whey and propanediol mononitrate. It is understood that the compounds may be administered to the animal in different other forms. For example the compounds can also be included in a bolus that would be placed in the rumen and that would release a defined amount of the active compounds continuously in well-defined dosages over a specific period of time.
  • the feed composition according to the present invention is a ruminant feed (often also referred to as ruminant diet) where all the dietary components, e.g. macro and micro ingredients, forage, silage and concentrate feed and additives including whey and propanediol mononitrate are included.
  • ruminant feed or diet is also often referred to as total mixed ration (TMR) or Partial mixed ration (PMR) or nutritional supplement for grazing animals.
  • the amount of the propanediol mononitrate is selected in the range from 1 mg to about 25 g per kg dry matter feed, preferably from about 1 mg to about 10 g per kg dry matter feed, more preferably from about 10 mg to about 1 g per Kg dry matter feed, most preferably from 20 mg to 500 mg per Kg of dry matter feed, such as from about 20 mg to 250 mg per Kg of dry matter feed, or even mor preferably from 10 mg to 300 mg per dry matter kg feed such as in the range from 50 mg to 150 mg per kg dry matter feed or 60 mg to 100 mg per kg dry matter feed.
  • the amount of whey is selected in the range from 5 mg to about 5 g whey per kg dry matter feed, preferably from about 5 mg to about 2.5 g of whey per kg dry matter feed, more preferably 5 mg to about 2 g whey per Kg dry matter feed, most preferably from 10 mg to 1.5 g whey per Kg of dry matter feed. Further particular suitable ranges are from 10 mg to 1.25 g whey per Kg of dry matter feed or 10 mg to 1 g whey per Kg of dry matter feed.
  • Daily dry matter intake for cattle is generally in the range of 1 to 3.5 % of dry matter per kg live weight.
  • the amount of dry matter intake (DMI) for dairy cows is, for example, about 2-3 % dry matter per kg live weight, the amount of dry matter intake for beef cattle is generally between 1 .0 - 3% of live weight depending on the feeding system as feedlot or grazing.
  • whey and the propanediol mononitrate have to be supplemented timely together to excerpt the synergistic effect, can however been added separately to the diet of the animal, e.g. can be added separately into the respecting feeding rack.
  • the present invention relates to a method of supplementing whey and propanediol mononitrate to a ruminant, said method encompassing the step of adding whey and propanediol mononitrate with all the definitions and preferences as given herein concomitantly to a feed rack.
  • the amount of ruminant feed administered to a ruminant may vary dependent on the kind and age. Generally, the amount of dry matter fed to beef cattle or dairy cows is selected in the range of 1 .5% to 3.5% of live weight, such as for an animal of 500 kg of live weigh it means to feed 7.5 to 17.5 kg dry matter/d. In all embodiments of the present invention, it is to be understood by oral administration, a simple feeding, or manual administration of a bolus. It is also well understood, that propanediol mononitrate and the whey can be pre-mixed before the administration or can be added separately to the animal feed compositions and feed additives.
  • Methane emission by ruminants can easily be measured in individual animals in metabolic chambers by methods known in the art (Grainger et al., 2007 J. Dairy Science; 90: 2755- 2766). Moreover, it can also be assessed at barn level by an emerging technology using laser beam (McGinn et al., 2009, Journal of Environmental Quality; 38: 1796-1802) or Sulfur hexafluoride or just SF6 or GreenFeed system. Alternatively, methane produced by a dairy ruminant can also be assessed by measurement of fatty acid profiles in milk according to WO 2009/156453.
  • the present invention also relates to the use of a feed composition or feed additive according to the present invention which feed composition or feed additive comprises one or more additional active substance which shows similar effects with regard to methane formation in the rumen and which is selected from the group consisting of diallyl disulfide, garlic oil, allyl isothiocyanate, deoxycholic acid, chenodeoxycholic acid and derivatives thereof.
  • yeasts for example yeasts, oregano extracts, tannins and tannic acids and essential oils e.g., thymol, 3-methylphenol, vaniline, guajacol and eugenol.
  • diallyl disulfide, garlic oil, allyl isothiocyanate deoxycholic acid, chenodeoxycholic acid and derivatives thereof are independently administered in dosage ranges of for example 0.01-500 mg active substance per kg feed (ppm).
  • ppm active substance per kg feed
  • Ruminating mammals include cattle, goats, sheep, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and Nilgai.
  • domestic cattle, sheep and goat are the more preferred species.
  • most preferred species are domestic cattle.
  • the term includes all races of domestic cattle, and all production kinds of cattle, in particular dairy cows and beef cattle. It is well understood that the term dairy cows and beef cattle encompasses animals in all ages and physiological stage of life and production systems such as confined, semi-confined and grazing.
  • the present invention relates to the use of whey to synergistically enhance the methane reducing properties of propanediol mononitrate in ruminants. It is well understood that all the definitions and properties as defined herein also apply to said use.
  • Cows were spitted in two treatment groups, one with 3- Nitrooxy propanol and one placebo. Cows were randomly assigned to one of the three supplement treatments with liquid whey (LW), concentrated whey (CW) and a powderous formulation (WP). Treatment periods were 2 weeks in duration.
  • LW liquid whey
  • CW concentrated whey
  • WP powderous formulation
  • Methane Production (Hohenheimer Test): Methane production (litres/d) and methane yield (litres/kg DM I) were significantly reduced by using LW, CW or WP on top of 3- Nitrooxypropanol (see table 1 below).

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Abstract

La présente invention concerne le domaine de la réduction de l'émission de méthane chez les ruminants. En particulier, l'invention concerne l'administration de lactosérum et de mononitrate de propanediol à un ruminant pour réduire la production de méthane émanant des activités digestives dudit ruminant.
PCT/EP2024/075316 2023-09-11 2024-09-11 Utilisation de lactosérum et de mononitrate de propanediol pour réduire l'émission de méthane de ruminants Pending WO2025056580A1 (fr)

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AU2024340325A AU2024340325A1 (en) 2023-09-11 2024-09-11 Use of whey and propanediol mononitrate to reduce methane emission of ruminants

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EP23196681.3 2023-09-11
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043898A1 (fr) 2002-11-14 2004-05-27 Dipharma S.P.A. Procede pour la mononitration d'alcanediols
WO2009156453A1 (fr) 2008-06-25 2009-12-30 Valorisation Par Extrusion Procédé d'évaluation de la quantité de méthane produite par un ruminant laitier et procédé pour diminuer et contrôler cette quantité
WO2012084629A1 (fr) 2010-12-20 2012-06-28 Dsm Ip Assets B.V. Utilisation de molécules organiques nitrooxy dans l'alimentation animale pour réduire l'émission de méthane chez les ruminants, et/ou pour améliorer la performance des ruminants
WO2018149756A1 (fr) 2017-02-14 2018-08-23 Dsm Ip Assets B.V. Formulations stables au stockage
WO2018149755A1 (fr) 2017-02-14 2018-08-23 Dsm Ip Assets B.V. Formulations dispersibles dans l'eau
US20220192229A1 (en) * 2019-04-16 2022-06-23 Dsm Ip Assets B.V. Early life nutrition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043898A1 (fr) 2002-11-14 2004-05-27 Dipharma S.P.A. Procede pour la mononitration d'alcanediols
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