(WO2019185938) Novel use of substituted chroman-6-ols with extended lipophilic side chains 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(WO2019185938) Novel use of substituted chroman-6-ols with extended lipophilic side chains
公开号/公开日
WO2019/185938WO2019/185938 / 2019-11-072019-10-03
申请号/申请日
WOEP2019/058117 / 2019-03-29
发明人
CLASADONTE LAUREDUESTERLOH ANDRÉINDRASENA WEERASINGHENETSCHER THOMASSTEMMLER RENÉ;
申请人
DSM;
主分类号
IPC分类号
C07D-311/72
摘要
(WO2019/185938) The present invention is directed towards the use of substituted chroman-6- ols with extended lipophilic side chains of formula (I) wherein one of the two substituents R1 and R2 is C12-21-alkyl and the other of the two substituents R1 and R2 is either hydrogen or C1-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and wherein A is CH(R3), and wherein R3, R4 and R6 are independently from each other H or C1-4-alkyl, and wherein R5 is H or OH or C1-4-alkyl or C1-4-alkoxy; with the proviso that at least two of R4, R5 and R6 are not methyl, when R3 is H and one of the substituents R1 and R2 is methyl and the other of the two substituents R1 and R2 is C12-21-alkyl, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such substituted chroman-6-ols with extended lipophilic side chains of formula (I).
机翻摘要
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地址
代理人
(WO2019185938) STECK, Melanie ([CH])
代理机构
;
优先权号
2018EP-0164860
主权利要求
(WO2019/185938) 1. Claims 1 . Use of a compound of formula (I) as antioxidant in a feed or in a feed ingredient,  wherein one of the two substituents R1and R2is C12-21-alkyl and the other of the two substituents R1and R2is either hydrogen or Ci-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and   wherein A is CH(R3), and   wherein R3, R4and R6are independently from each other H or Ci-4- alkyl, and   wherein R5is H or OH or Ci-4-alkyl or Ci-4-alkoxy;   with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is Ci2-2i-alkyl. 2. The use according to claim 1 , whereby in compound of formula (I) one of the two substituents R1and R2is C12-21-alkyl and the other of the two substituents R1and R2is either hydrogen or Ci-5-alkyl, and   wherein R3, R4and R6are independently from each other H or Ci-4- alkyl, and   wherein R5is H or OH or Ci-4-alkyl or Ci-4-alkoxy;   with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is C12-21-alkyl. 3. The use according to claim 1 or 2, whereby in compound of formula (I) one of the two substituents R1and R2is C12-21 -alkyl and the other of the two substituents R1and R2is either hydrogen or methyl or ethyl, and wherein R3and R4are independently from each other H or methyl or ethyl, and R6is H or Ci-4-alkyl, preferably R6is H or methyl or ethyl, wherein R5is H or OH or methyl or ethyl or methoxy or ethoxy;   with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is C12-21 -alkyl. 4. The use according to any one or more of claims 1 to 3, whereby in compound of formula (I) one of the two substituents R1and R2is C12-21 - alkyl and the other of the two substituents R1and R2is either hydrogen or methyl, and wherein   R3is H, and wherein   R4is H or methyl, and wherein   R6is H or Ci-4-alkyl, preferably R6is H or methyl or ethyl, and wherein R5is H or OH or methyl or methoxy,   with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is C12-21 -alkyl. 5. The use according to claim 1 , whereby the compound of formula (I) is compound of formula (1 ) or compound of formula (2) or any mixture thereof.   6. The use according to any one or more of the preceding claims, whereby the feed ingredient is either poultry meal or fish meal or insect meal or PUFA-containing oil. 7. The use according to claim 6, whereby the PUFA-containing oil is   marine oil or microbial oil or fungal oil or algal oil or PUFA-containing plant oil, preferably whereby the PUFA-containing oil is marine oil or algal oil, more preferably whereby the PUFA-containing oil is algal oil. 8. Feed ingredient comprising at least one compound of formula (I),  wherein one of the two substituents R1and R2is C12-21-alkyl and the other of the two substituents R1and R2is either hydrogen or Ci-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and   wherein A is CH(R3), and   wherein R3, R4and R6are independently from each other H or Ci-4-alkyl, and wherein R5is H or OH or Ci-4-alkyl or Ci-4-alkoxy,   with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is C12-21-alkyl. 9. The feed ingredient according to claim 8, whereby the feed ingredient is either poultry meal or fish meal or insect meal or PUFA-containing oil. 10. The feed ingredient according to claim 9, whereby the PUFA-containing oil is marine oil or microbial oil or fungal oil or algal oil or PUFA- containing plant oil, preferably whereby the PUFA-containing oil is marine oil or algal oil, more preferably whereby the PUFA-containing oil is algal oil.   11 . The feed ingredient according to any one or more of claims 8 to 10 additionally comprising a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol. 12. The feed ingredient according to any one or more of claims 8 to 1 1 additionally comprising esters of ascorbic acid with linear C12-20 alkanols, preferably esters of ascorbic acid with linear C14-18 alkanols, more preferably ascorbyl palmitate. 13. The feed ingredient according to any one or more of claims 8 to 12 additionally comprising alpha-tocopherol and/or gamma-tocopherol. 14. The use according to any one or more of claims 1 to 5, whereby the feed is feed for aquatic animals, feed for terrestrial animals   (preferably feed for poultry, pets or pigs) or feed for insects. 15. Feed for aquatic or terrestrial animals or insects comprising at least one compound of formula (I), wherein one of the two substituents R1and R2is C12-21 -alkyl and the other of the two substituents R1and R2is either hydrogen or Ci-5-alkyl or (CH2)n-OH with n being an integer from 1 to 5, and   wherein A is CH(R3), and   wherein R3, R4and R6are independently from each other H or Ci-4-alkyl, and wherein R5is H or OH or Ci-4-alkyl or Ci-4-alkoxy; with the proviso that at least two of R4, R5and R6are not methyl, when R3is H and one of the substituents R1and R2is methyl and the other of the two substituents R1and R2is C12-21 -alkyl. 16. The feed according to claim 15 being pet food, feed for poultry or feed for pigs. 17. A process for the manufacture of a compound of formula (IA),   comprising the step of reacting a compound of formula (II) with a compound of formula (III) in the presence of an acid catalyst and in a mixture of two solvents,   wherein n is 3, and   R1and R3are independently from each other H or methyl, and R2is either H or methyl or methoxy,   the first of the two solvents is selected from ethylene carbonate, propylene carbonate, 1 ,2-butylene carbonate, gamma-butyrolactone and water,   and the second of the two solvents is selected from hexane, cyclohexane, heptane, ortho-xylene, meta-xylene, para-xylene, mesitylene, pseudocumene, methyl tert- butyl ether, and toluene. 18. The process according to claim 17, wherein the first of the two solvents is ethylene carbonate or propylene carbonate, and the second of the two solvents is selected from either hexane, cyclohexane or heptane, preferably wherein the first of the two solvents is ethylene carbonate and the second of the two solvents is heptane. 19. The process according to claim 17 and/or 18, wherein the volume ratio of the first solvent to the second solvent during the reaction is in the range of 1 :4 to 4:1 , preferably wherein the volume ratio of the first solvent to the second solvent is in the range of 1 :3 to 3:1 most preferably wherein the volume ratio of the first solvent to the second solvent is in the range of 1 :2 to 2:1. 20. The process according to any one or more of claims 17 to 19, wherein the total amount of the two solvents is in the range of 1 to 10 kg, preferably in the range of 2 to 7 kg, more preferably in the range of 2.5 to 6 kg, per kg of the compound of formula (II).   21 . The process according to any one or more of claims 17 to 20, wherein the acid catalyst is selected from Bronsted acids, Lewis acids and any mixtures thereof. 22. The process according to claim 21 , wherein the acid catalyst is a   Bronsted acid, and whereby the Bronsted acid is selected from sulfuric acid, phosphoric acid, acidic ion -exchange resins, acidic clays, zeolites, hydrochloric acid, trifluoroacetic acid, trichloroacetic acid, acetic acid, formic acid, methanesulfonic acid, benzenesulfonic acid, para- toluenesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, bis(perfluoroalkylsulfonyl)methanes (R’S02)(R”S02)CH2wherein R’ and R” each signify independently from each other a perfluoroalkyl group of the formula CnF2n+iwhere n is an integer from 1 to 10,   tris(perfluorosulfonyl)methanes (R’S02)(R”S02)(R”’S02)CH, wherein R’, R” and R’” each signify independently from each other a perfluoroalkyl group of the formula CnF2n+iwhere n is an integer from 1 to 10, and whereby at least two of R’, R” and R’” are identical perfluoroalkyl groups, or R’ signifies the pentafluorophenyl group (-C6F5) and R” and R’” each signify an identical perfluoroalkyl group of the above formula CnF2n+i, methanetrisulfonic acid, and bis(trifluormethylsulfonyl)imide, and any mixture thereof, whereby the use of single catalysts is preferred. 23. The process according to claim 21 , wherein the acid catalyst is a Lewis acid, and whereby the Lewis acid is selected from Al(OTf)3, Sc(OTf)3, Sc(NTf2)3, ScCl3, Yb(OTf)3, YbCl3, Cu(OTf)2, FeCl2, Fe(OTf)2, ZnCl2, Zn(OTf)2, Zn(NTf2)3, YCl3, Y(OTf)3, lnCl3, lnBr3, ln(OTf)3, ln(NTf2)3, La(OTf)3, Ce(OTf)3, Sm(OTf)3, Gd(OTf)3and Bi(OTf)3in the presence or absence of 2,2-bipyridine. 24. The process according to any one or more of the claims 17 to 21 ,   wherein the acid catalyst is para-toluenesulfonic acid, sulfuric acid, methanesulfonic acid, Al(OTf)3, Sc(OTf)3, or ln(OTf)3, most preferably wherein the acid catalyst is para-toluenesulfonic acid or Al(OTf)3. 25. The process according to any one or more of claims 17 to 24, wherein the amount of the acid catalyst is in the range of 0.001 to 5 mol equivalents, preferably in the range of 0.005 to 1 mol equivalents, more preferably in the range of 0.01 to 0.1 mol equivalents, relative to the amount of compound of formula (III). 26. The process according to any one or more of claims 17 to 25, wherein the molar ratio of the compound of formula (II) to the compound of formula (III) is in the range of 6.0: 1 to 1 .1 :1 , preferably in the range of 4.0: 1 to 1.2:1 , even more preferably in the range of from 3.0: 1 to 1.3:1 , most preferably in the range of 2.0:1 to 1 .5:1 . 27. The process according to any one or more of the claims 17 to 26,   wherein the reaction is carried out at a temperature in the range of from 70 to 160°C, preferably in the range of from 80 to 130°C, most preferably in the range of from 90-105 ° C. 28. The process according to any one or more of claims 17 to 27, wherein the reaction is carried out at a pressure in the range of from 0.8 to 20 bar (absolute), preferably at a pressure in the range of from 0.8 to 10 bar (absolute), most preferably at a pressure in the range of from 0.8 to 5 bar (absolute). 29. The process according to any one or more of claims 17 to 28, wherein the acid catalyst is reusable.
法律状态
PENDING
专利类型码
A3A2
国别省市代码
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