CN106660032A - 固体酸催化剂及氧化物的制造方法 - Google Patents
固体酸催化剂及氧化物的制造方法 Download PDFInfo
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- CN106660032A CN106660032A CN201580044244.2A CN201580044244A CN106660032A CN 106660032 A CN106660032 A CN 106660032A CN 201580044244 A CN201580044244 A CN 201580044244A CN 106660032 A CN106660032 A CN 106660032A
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- 239000000126 substance Substances 0.000 claims abstract description 27
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- USMNOWBWPHYOEA-MRTMQBJTSA-N α-thujone Chemical compound O=C([C@@H]1C)C[C@@]2(C(C)C)[C@@H]1C2 USMNOWBWPHYOEA-MRTMQBJTSA-N 0.000 description 1
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Abstract
本发明提供一种固体酸催化剂,其是在氧和臭氧的共存下对基质进行氧化时使用的氧‑臭氧共存下氧化反应用的固体酸催化剂,可以以高的转化率对该基质进行氧化。本发明的氧‑臭氧共存下氧化用固体酸催化剂为在氧和臭氧的共存下对基质(A)进行氧化时使用的氧化反应用的固体酸催化剂,其中,过渡金属以单质、化合物或离子的形态担载于至少在表面具有哈米特的酸度函数(H0)为‑9以下的强酸或超强酸的载体。所述载体优选为由氟化磺酸类树脂构成的颗粒或粉粒体,或者为在固体表面上形成有氟化磺酸类树脂的覆膜的载体。
Description
技术领域
本发明涉及一种在氧和臭氧的共存下对基质进行氧化时使用的氧-臭氧共存下氧化反应用的固体酸催化剂、及使用有该固体酸催化剂的氧化物的制造方法。本申请主张2014年8月29日在日本所申请的日本特愿2014-175314的优先权,在此引用其内容。
背景技术
氧化反应为有机化学工业中的最基本的反应之一,开发有各种氧化方法。专利文献1中记载有使用脂溶性酰亚胺化合物作为催化剂,利用分子状氧等对可生成自由基的化合物进行氧化的方法。根据该方法,可以使多种多样的有机基质氧化从而得到对应的氧化物。但是,该方法在基质的转化率或目标化合物的收率等方面不能说是一定能够在工业上充分满足的方法。
现有技术文献
专利文献
专利文献1:日本特开2002-331242号公报
发明内容
发明所要解决的课题
因此,本发明的目的在于,提供一种在氧和臭氧的共存下对基质进行氧化时使用的氧-臭氧共存下氧化反应用的固体酸催化剂,其是可以将该基质以高的转化率进行氧化的固体酸催化剂。
本发明的其它目的在于,提供一种由基质以高的收率得到氧化物(含氧化合物等)的方法。
用于解决课题的技术方案
本发明人等为了解决上述课题进行了深入研究,结果发现:在特定的固体酸催化剂的存在下且在氧和臭氧的共存下对基质进行氧化时,可以以高的转化率使该基质氧化,另外,以高的收率得到对应的氧化物(含氧化合物等),完成了本发明。
即,本发明涉及以下发明。
[1]一种氧-臭氧共存下氧化用固体酸催化剂,其是在氧和臭氧的共存下对下述基质(A)进行氧化时使用的氧化反应用的固体酸催化剂,其中,
过渡金属以单质、化合物或离子的形态担载于至少在表面具有哈米特的酸度函数(H0)为-9以下的强酸或超强酸的载体,
基质(A)选自下述的化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
[2]一种氧-臭氧共存下氧化用固体酸催化剂,其是在氧和臭氧的共存下对下述基质(A)进行氧化时使用的氧化反应用固体酸催化剂,其中,
过渡金属以单质、化合物或离子的形态担载于下述的载体,所述载体至少在表面具有选自硫酸、硫酸化金属氧化物、贵金属/硫酸化金属氧化物、金属氧化物超强酸、及氟化磺酸类树脂中的至少1种强酸或超强酸,
基质(A)选自下述的化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
[3]如上述[1]或[2]所述的固体酸催化剂,其中,所述在杂原子的邻位上具有碳-氢键的化合物(A1)为:(A1-1)伯醇或仲醇,或者伯硫醇或仲硫醇;(A1-2)在氧原子的邻位上具有碳-氢键的醚,或者在硫原子的邻位上具有碳-氢键的硫醚;或者,(A1-3)在氧原子的邻位上具有碳-氢键的缩醛(也包含半缩醛),或者在硫原子的邻位上具有碳-氢键的硫代缩醛(也包含硫代半缩醛)。
[4]如上述[1]~[3]中任一项所述的固体酸催化剂,其中,所述具有碳-杂原子双键的化合物(A2)为:(A2-1)含羰基的化合物;(A2-2)含硫代羰基的化合物;或者(A2-3)亚胺类。
[5]如上述[1]~[4]中任一项所述的固体酸催化剂,其中,所述具有次甲基碳原子的化合物(A3)为:(A3-1)含有作为环的构成单元的次甲基(即次甲基碳-氢键)的环状化合物;或(A3-2)具有次甲基碳原子的链状化合物。
[6]如上述[1]~[5]中任一项所述的固体酸催化剂,其中,所述在不饱和键的邻位上具有碳-氢键的化合物(A4)为:(A4-1)芳香族性环的邻位(所谓的苄基位)上具有甲基或亚甲基的芳香族化合物;或者(A4-2)在不饱和键的邻位上具有甲基或亚甲基的非芳香族性化合物。
[7]如上述[1]~[6]中任一项所述的固体酸催化剂,其中,所述脂环式化合物(=非芳香族性环状烃)(A5)为:(A5-1)环链烷烃类;或者(A5-2)环链烯类。
[8]如上述[1]~[7]中任一项所述的固体酸催化剂,其中,所述共轭化合物(A6)为共轭二烯类(A6-1)、α,β-不饱和腈(A6-2)、或α,β-不饱和羧酸或其衍生物(A6-3)。
[9]如上述[1]~[8]中任一项所述的固体酸催化剂,其中,所述胺化合物(A7)为伯或仲胺。
[10]如上述[1]~[9]中任一项所述的固体酸催化剂,其中,所述芳香族化合物(A8)为至少具有1个苯环的芳香族烃或至少苯环多个缩合成的缩合多环式芳香族烃。
[11]如上述[1]~[10]中任一项所述的固体酸催化剂,其中,所述直链状链烷烃(A9)为碳原子数1~30的直链状链烷烃。
[12]如上述[1]~[11]中任一项所述的固体酸催化剂,其中,所述烯烃(A10)为链状烯烃或环状烯烃。
[13]如上述[1]~[12]中任一项所述的固体酸催化剂,其中,所述基质(A)为烃。
[14]如上述[13]所述的固体酸催化剂,其中,所述烃为选自脂肪族烃、脂环式烃、及芳香族烃中的至少1个。
[15]如上述[1]~[14]中任一项所述的固体酸催化剂,其中,所述载体为由氟化磺酸类树脂构成的颗粒或粉粒体,或者为在固体表面上形成有氟化磺酸类树脂的覆膜的载体。
[16]如上述[1]~[15]中任一项所述的固体酸催化剂,其中,所述过渡金属为选自钴、锰、钒、铁、锆、钨及钼中的至少1种。
[17]如上述[1]~[16]中任一项所述的固体酸催化剂,其中,所述过渡金属为选自钴、锰、钒、铁及锆中的至少1种。
[18]如上述[1]~[17]中任一项所述的固体酸催化剂,其中,所述过渡金属为选自钴及锰中的至少1种。
[19]如上述[1]~[18]中任一项所述的固体酸催化剂,其形状为颗粒状、膜状或管状。
[20]一种氧化物的制造方法,其特征在于,在上述[1]~[19]中任一项所述的固体酸催化剂的存在下,在氧及臭氧的共存下对下述基质(A)进行氧化。
基质(A)选自化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
[21]如上述[20]所述的氧化物的制造方法,其进一步在具有环状酰亚胺骨架的酰亚胺化合物的存在下对基质进行氧化。
发明的效果
根据本发明,由于在特定的固体酸催化剂的存在下且在氧和臭氧的共存下对基质进行氧化,因此,氧化速度显著地提高,可以使广泛的基质以高的转化率进行氧化。另外,即使基质为烃,特别为直链状链烷,也可以以高的收率得到氧化物(含氧化合物等)。
具体实施方式
[反应基质]
作为用作本发明中反应基质(A)的有机化合物(有机基质),优选能够生成稳定的自由基的化合物,可举出选自下述的化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
这些化合物在不阻碍反应的范围下可以具有各种取代基。作为所述取代基,可举出例如:卤原子、羟基、巯基、氧代基、取代氧基(例如烷氧基、芳氧基、酰氧基等)、取代硫基、羧基、取代氧羰基、取代或无取代氨基甲酰基、氰基、硝基、取代或无取代氨基、磺基、烷基、烯基、炔基、脂环式烃基、芳香族烃基、杂环基等。
作为在杂原子的邻位上具有碳-氢键的化合物(A1),可以例示:(A1-1)伯醇或仲醇,或者伯硫醇或仲硫醇;(A1-2)在氧原子的邻位上具有碳-氢键的醚,或者在硫原子的邻位上具有碳-氢键的硫醚;(A1-3)在氧原子的邻位上具有碳-氢键的缩醛(也包含半缩醛),或者在硫原子的邻位上具有碳-氢键的硫代缩醛(也包含硫代半缩醛)等。
在所述(A1-1)中的伯醇或仲醇中包含广泛围的醇。另外,醇可以为1元、2元、或多元醇的任一种。
作为代表的伯醇,可举出:甲醇、乙醇、1-丙醇、1-丁醇、1-戊醇、1-己醇、1-辛醇、1-癸醇、2-丁烯-1-醇、乙二醇、三亚甲基二醇、六亚甲基二醇、季戊四醇等碳原子数1~30左右(优选1~20、特别优选1~15)的饱和或不饱和脂肪族伯醇;环戊基甲基醇、环己基甲基醇、2-环己基乙基醇等饱和或不饱和脂环式伯醇;苄醇、2-苯基乙基醇、3-苯基丙基醇、肉桂醇等芳香族伯醇;2-羟基甲基吡啶等杂环式醇。
作为代表的仲醇,包含:2-丙醇、仲丁基醇、2-戊醇、2-辛醇、2-戊烯-4-醇、1,2-丙二醇、2,3-丁二醇或2,3-戊二醇等邻二醇类等碳原子数3~30左右(优选3~20、特别优选3~15)的饱和或不饱和脂肪族仲醇;1-环戊基乙醇、1-环己基乙醇等在羟基键合的碳原子上键合有脂肪族烃基和脂环式烃(环烷基等)的仲醇;环戊醇、环己醇、环辛醇、环十二醇、2-环己烯-1-醇、2-金刚烷醇、在桥头位上具有1~4个羟基的2-金刚烷醇、在金刚烷环上具有氧代基团的2-金刚烷醇等3~20元左右(优选3~15元、特别优选5~15元、最优选5~8元)的饱和或不饱和脂环式仲醇(包含交联环式仲醇);1-苯基乙醇等芳香族仲醇;1-(2-吡啶基)乙醇等杂环式仲醇等。
并且,在代表的醇中也包含:1-金刚烷甲醇、α-甲基-1-金刚烷甲醇、3-羟基-α-甲基-1-金刚烷甲醇、3-羧基-α-甲基-1-金刚烷甲醇、α-甲基-3a-全氢茚甲醇、α-甲基-4a-十氢化萘甲醇、α-甲基-4a-全氢芴甲醇、α-甲基-2-三环[5.2.1.02,6]癸烷甲醇、α-甲基-1-降冰片烷甲醇等具有交联环烃基的醇(在羟基键合的碳原子上键合有交联环烃基的化合物等)。
作为所述(A1-1)中的伯硫醇或仲硫醇,可举出与所述伯醇或仲醇对应的硫醇。
作为所述(A1-2)中的在氧原子的邻位上具有碳-氢键的醚,可举出例如:二甲基醚、二乙基醚、二丙基醚、二异丙基醚、二丁基醚、二烯丙基醚等脂肪族醚类;苯甲醚、苯乙醚、二苄基醚、苯基苄基醚等芳香族醚类;二氢呋喃、四氢呋喃、吡喃、二氢吡喃、四氢吡喃、吗啉、色满、异色满等环状醚类(芳香环或非芳香环可以进行缩合)等。
作为所述(A1-2)中的在硫原子的邻位上具有碳-氢键的硫醚,可举出与所述在氧原子的邻位上具有碳-氢键的醚对应的硫醚。
作为所述(A1-3)中的在氧原子的邻位上具有碳-氢键的缩醛,可举出例如由醛和醇或酸酐等所衍生的缩醛、在该缩醛中包含环状缩醛及非环状缩醛。作为所述醛,可举出例如:甲醛、乙醛、丙醛、丁醛、异丁醛等脂肪族醛;环戊烷甲醛、环己烷甲醛等脂环式醛;苯甲醛、苯基乙醛等芳香族醛等。另外,作为所述醇,可举出例如:甲醇、乙醇、1-丙醇、1-丁醇、苄醇等一元醇;乙二醇、丙二醇、1,3-丙二醇、2,2-二溴-1,3-丙二醇等二元醇等。作为代表的缩醛,可例示:1,3-二氧杂戊环、2-甲基-1,3-二氧杂戊环、2-乙基-1,3-二氧杂戊环等1,3-二氧杂戊环化合物;2-甲基-1,3-二噁烷等1,3-二噁烷化合物;乙醛二甲基缩醛等二烷基缩醛化合物等。
作为所述(A1-3)中的在硫原子的邻位上具有碳-氢键的硫代缩醛,可举出与所述在氧原子的邻位上具有碳-氢键的缩醛对应的硫代缩醛。
作为所述具有碳-杂原子双键的化合物(A2),可举出:(A2-1)含羰基的化合物、(A2-2)含硫代羰基的化合物、(A2-3)亚胺类等。在含羰基的化合物(A2-1)中包含酮及醛,可举出例如:丙酮、甲基乙基酮、甲基异丁基酮、3-戊酮、甲基乙烯基酮、甲基环己基酮、苯乙酮等链状酮类;环戊酮、环己酮、4-甲基环己酮、异佛尔酮、环癸酮、环十二酮、1,4-环辛烷二酮、2,2-双(4-氧代环己基)丙烷、2-金刚烷酮等环状酮类;联乙酰基(2,3-丁二酮)、联苯甲酰基(=苄基)、乙酰基苯甲酰基、环己烷-1,2-二酮等1,2-二羰基化合物(α-二酮类等);乙偶姻、苯偶姻等α-酮醇类;乙醛、丙醛、丁醛、己醛、琥珀醛、戊二醛、己二醛等脂肪族醛;环己基醛、柠檬醛、香茅醛等脂环式醛;苯甲醛、羧基苯甲醛、硝基苯甲醛、肉桂醛、水杨醛、茴香醛、邻苯二甲醛、异邻苯二甲醛、对苯二甲醛等芳香族醛;糠醛、烟醛等杂环醛等。
作为含硫代羰基的化合物(A2-2),可举出与所述含羰基的化合物(A2-1)对应的含硫代羰基的化合物。
亚胺类(A2-3)中包含:所述含羰基的化合物(A2-1)、由氨或胺类(例如甲胺、乙胺、丙胺、丁胺、己胺、苄胺、环己基胺、苯胺等胺;羟基胺、O-甲基羟基胺等羟基胺类;肼、甲基肼、苯基肼等肼类等)所衍生的亚胺类(也包含肟或腙)。
所述具有次甲基碳原子的化合物(A3)中包含:(A3-1)含有作为环的构成单元的次甲基(即次甲基碳-氢键)的环状化合物;(A3-2)具有次甲基碳原子的链状化合物。
环状化合物(A3-1)中包含:(A3-1a)具有至少1个次甲基的交联环式化合物;(A3-1b)在环上键合有烃基的非芳香族性环状化合物(脂环式烃等)。另外,在所述交联环式化合物中也包含2个环共用2个碳原子的化合物(例如缩合多环式芳香族烃类的氢化生成物等)。
作为交联环式化合物(A3-1a),可举出例如:十氢化萘、双环[2.2.0]己烷、双环[2.2.2]辛烷、双环[3.2.1]辛烷、双环[4.3.2]十一碳烷、双环[3.3.3]十一碳烷、侧柏酮、蒈烷、蒎烷、蒎烯、莰烷、冰片烯、降冰片烷、降冰片烯、樟脑、樟脑酸、茨烯、三环烯、三环[5.2.1.03,8]癸烷、三环[4.2.1.12,5]癸烷、外三环[5.2.1.02,6]癸烷、内三环[5.2.1.02,6]癸烷、三环[4.3.1.12,5]十一碳烷、三环[4.2.2.12,5]十一碳烷、内三环[5.2.2.02,6]十一碳烷、金刚烷、1-金刚烷醇、1-氯金刚烷、1-甲基金刚烷、1,3-二甲基金刚烷、1-甲氧基金刚烷、1-羧基金刚烷、1-甲氧基羰基金刚烷、1-硝基金刚烷、四环[4.4.0.12,5.17,10]十二烷、全氢蒽、全氢苊、全氢菲、全氢非那烯、全氢茚、奎宁环等2~4环式的交联环式烃或交联杂环化合物、及它们的衍生物等。这些交联环式化合物在桥头位(在2个环共用2个原子的情况下相当于接合部位)上具有次甲基碳原子。
作为在环上键合有烃基的非芳香族性环状化合物(A3-1b),可举出:1-甲基环戊烷、1-甲基环己烷、柠檬萜、薄荷烯、薄荷醇、莳萝薄荷酮、薄荷酮等碳原子数1~20左右(优选1~10)的烃基(例如烷基等)键合于环上的3~15元左右的脂环式烃、及其衍生物等。在环上键合有烃基的非芳香族性环状化合物(A3-1b)在环和所述烃基的键合部位上具有次甲基碳原子。
作为具有次甲基碳原子的链状化合物(A3-2),可以例示:具有叔碳原子的链状烃类[例如:异丁烷、异戊烷、异己烷、3-甲基戊烷、2,3-二甲基丁烷、2-甲基己烷、3-甲基己烷、3,4-二甲基己烷、3-甲基辛烷等碳原子数4~20左右(优选4~10)的脂肪族烃类、及其衍生物]等。
作为所述在不饱和键的邻位上具有碳-氢键的化合物(A4),可举出:在(A4-1)芳香族性环的邻位(所谓的苄基位)上具有甲基或亚甲基的芳香族化合物;在(A4-2)不饱和键(例如碳-氧双键等碳-碳不饱和键)的邻位上具有甲基或亚甲基的非芳香族性化合物等。
在所述芳香族性化合物(A4-1)中,芳香族性环可以为芳香族烃环、芳香族性杂环的任一者。在芳香族烃环中包含苯环、缩合碳环(例如萘、薁、苯并二茚、蒽、菲、9,10-苯并菲、芘等4~7元碳环2~10个缩合而成的缩合碳环等)。作为芳香族性杂环,可举出例如:含有氧原子作为杂原子的杂环(例如呋喃、噁唑、异噁唑等5元环、4-氧代-4H-吡喃等6元环、苯并呋喃、异苯并呋喃、4-氧代-4H-色烯等缩合环等)、含有硫原子作为杂原子的杂环(例如噻吩、噻唑、异噻唑、噻二唑等5元环、4-氧代-4H-硫代吡喃等6元环、苯并噻吩等缩合环等)、含有氮原子作为杂原子的杂环(例如吡咯、吡唑、咪唑、三唑等5元环、吡啶、哒嗪、嘧啶、哌嗪等6元环、吲哚、喹啉、吖啶、萘啶、喹唑啉、嘌呤等缩合环等)。
予以说明,芳香族性环的邻位的亚甲基可以为构成在所述芳香族性环上缩合的非芳香族性环的亚甲基。另外,在所述(A4-1)中,可以在与芳香族性环邻接的位置上存在甲基和亚甲基的两种基团。
作为在芳香族性环的邻位上具有甲基的芳香族化合物,可以例示例如:在芳香环上取代有1~6个左右的甲基的芳香族烃类(例如甲苯、邻二甲苯、间二甲苯、对二甲苯、邻叔丁基甲苯、间叔丁基甲苯、对叔丁基甲苯、1-乙基-4-甲基苯、1-乙基-3-甲基苯、1-异丙基-4-甲基苯、1-叔丁基-4-甲基苯、1-甲氧基-4-甲基苯、均三甲基苯、假枯烯、均四甲苯、甲基萘、二甲基萘、甲基蒽、4,4'-二甲基联苯、甲苯甲醛、二甲基苯甲醛、三甲基苯甲醛、甲苯酸、三甲基苯甲酸、二甲基苯甲酸等)、在杂环上取代有1~6个左右的甲基的杂环化合物(例如2-甲基呋喃、3-甲基呋喃、3-甲基噻吩、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2,4-二甲基吡啶、2,4,6-三甲基吡啶、4-甲基吲哚、2-甲基喹啉、3-甲基喹啉等)。
作为在芳香族性环的邻位上具有亚甲基的芳香族化合物,可以例示例如:具有碳原子数2以上的烷基或取代烷基的芳香族烃类(例如乙基苯、丙基苯、丁基苯、1,4-二乙基苯、二苯基甲烷等)、具有碳原子数为2以上的烷基或取代烷基的芳香族性杂环化合物(例如2-乙基呋喃、3-丙基噻吩、4-乙基吡啶、4-丁基喹啉等)、为在芳香族性环上缩合有非芳香族性环而成的化合物、且在邻接于该非芳香族性环中的芳香族性环的部位具有亚甲基的化合物(例如二氢萘、茚、茚满、四氢化萘、芴、苊、菲、茚酮、呫吨等)。
在不饱和键的邻位上具有甲基或亚甲基的非芳香族性化合物(A4-2)可以例示例如(A4-2a)在所谓的烯丙基位上具有甲基或亚甲基的链状不饱和烃类、(A4-2b)在羰基的邻位上具有甲基或亚甲基的化合物。
作为所述链状不饱和烃类(A4-2a),可以例示例如:丙烯、1-丁烯、2-丁烯、1-戊烯、1-己烯、2-己烯、1,5-己二烯、1-辛烯、3-辛烯、十一碳三烯等碳原子数3~20左右的链状不饱和烃类。在所述化合物(A4-2b)中包含酮类(例如丙酮、甲基乙基酮、3-戊酮、苯乙酮等链状酮类;环己酮等环状酮类)、羧酸或其衍生物(例如乙酸、丙酸、丁烷酸、戊烷酸、己烷酸、庚酸、苯基乙酸、丙二酸、琥珀酸、戊二酸、及它们的酯等)。
在所述脂环式化合物(=非芳香族性环状烃)(A5)中包含(A5-1)环链烷烃类及(A5-2)环链烯烃类。
作为所述环链烷烃类(A5-1),可举出例如:环丙烷、环丁烷、环戊烷、环己烷、环庚烷、环辛烷、环壬烷、环癸烷、环十二烷、环十四烷、环十六烷、环二十四烷、环三十烷等具有3~30元(优选5~30元、特别优选5~20元)的环链烷环的化合物、及它们的衍生物等。
在所述环链烯烃类(A5-2)中包含例如:环丙烯、环丁烯、环戊烯、环辛烯、环己烯、1-甲基-环己烯、异佛尔酮、环庚烯、环十二碳烯等具有3~30元(优选3~20元环、特别优选3~12元)的环链烯环的化合物;环戊二烯、1,3-环己二烯、1,5-环辛二烯等环链二烯类;环辛三烯等环链三烯类;及它们的衍生物等。
所述共轭化合物(A6)可举出:共轭二烯类(A6-1)、α,β-不饱和腈(A6-2)、α,β-不饱和羧酸或其衍生物(例如酯、酰胺、酸酐等)(A6-3)等。
作为共轭二烯类(A6-1),可举出例如:丁二烯、异戊二烯、2-氯丁二烯、2-乙基丁二烯等。另外,在共轭二烯类(A6-1)中也包含双键和三键共轭的化合物(例如乙烯基乙炔等)。
作为α,β-不饱和腈(A6-2),可举出例如(甲基)丙烯腈等。
作为α,β-不饱和羧酸或其衍生物(A6-3),可举出例如:(甲基)丙烯酸;(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸-2-羟基乙酯等(甲基)丙烯酸酯;(甲基)丙烯酰胺、N-羟甲基(甲基)丙烯酰胺等(甲基)丙烯酰胺衍生物等。
作为所述胺化合物(A7),可举出例如:伯胺或仲胺[例如:甲基胺、乙基胺、丙基胺、丁基胺、二甲基胺、二乙基胺、二丁基胺、乙二胺、1,4-丁二胺、羟基胺、乙醇胺等脂肪族胺;环戊基胺、环己基胺等脂环式胺;苄胺、甲苯胺等芳香族胺;吡咯烷、哌啶、哌嗪、吲哚啉等环状胺(芳香族性或非芳香族性环可以进行缩合)]等。
作为所述芳香族化合物(A8),可举出例如:苯、萘、苊、菲、蒽、丁省等至少具有1个苯环的芳香族烃;至少苯环多个缩合(例如2~10个)而成的缩合多环式芳香族烃等。另外,在所述苯环中,非芳香族性碳环、芳香族性杂环、或非芳香族性杂环可以进行缩合。这些芳香族化合物可以具有1个或2个以上的取代基。作为具有取代基的芳香族化合物,具体而言,可举出:2-氯萘、2-甲氧基萘、1-甲基萘、2-甲基萘、1-溴蒽、2-甲基蒽、2-叔丁基蒽、2-羧基蒽、2-乙氧基羰基蒽、2-氰基蒽、2-硝基蒽、2-甲基戊搭烯等。
作为所述直链状链烷(A9),可举出例如:甲烷、乙烷、丙烷、丁烷、戊烷、己烷、庚烷、辛烷、壬烷、癸烷、十二烷、十四烷、十六烷等碳原子数1~30左右(优选碳原子数1~20)的直链状链烷。
作为所述烯烃(A10),可举出例如:可以具有取代基(例如羟基、酰氧基等)的α-烯烃、内烯烃、及二烯等具有多个碳-碳双键的烯烃等。具体而言,可举出:乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、1-己烯、2-己烯、1-乙酰氧基-3,7-二甲基-2,6-辛二烯、苯乙烯、乙烯基甲苯、α-甲基苯乙烯、3-乙烯基吡啶、3-乙烯基噻吩等链状烯烃;环戊烯、环己烯、环庚烯、环辛烯、环癸烯、环十二碳烯、1,4-环己二烯、柠檬萜、1-对薄荷烯、3-对薄荷烯、香芹醇、双环[2.2.1]庚-2-烯、双环[3.2.1]辛-2-烯、α-蒎烯、2-冰片烯等环状烯烃等。
上述的基质(A)可以单独使用1种,也可以将同种或不同种的物质组合2种以上而使用。在本发明中,由于在臭氧共存下使用作为氧化剂的氧,因此,可以以非常优异的氧化能力对基质进行氧化。因此,一般而言,认为难以氧化的直链状链烷烃(A9)也可以有效地进行氧化,可以以高收率得到对应的氧化物(含氧化合物)。
在本发明中,作为基质(A),特别优选烃。作为烃,可举出:脂肪族烃、脂环式烃、芳香族烃等。
作为脂肪族烃,可举出例如:乙烷、丙烷、丁烷、戊烷、己烷、庚烷、辛烷、壬烷、癸烷、十一碳烷、十二烷、十三烷、十四烷、十五烷、十六烷、十七烷、十八烷、十九烷、二十碳烷、二十一碳烷、二十二碳烷、三十烷、四十烷等直链状链烷(例如碳原子数3~30、优选4~20的直链状链烷等);2-甲基丙烷、2-甲基丁烷、2,2-二甲基丙烷、2-甲基戊烷、3-甲基戊烷、2,3-二甲基丁烷、2-甲基己烷、3-甲基己烷、3,4-二甲基己烷、3-甲基辛烷等支链状链烷(例如碳原子数3~30、优选4~20的支链状链烷等);丙烯、异丁烯、1-戊烯、1-己烯、2-己烯、1-庚烯、1-辛烯、1-癸烯、1-十二碳烯、1-十四烯、1,4-己二烯等直链状或支链状的链烯或链二烯[例如:碳原子数3~30、优选4~20的直链状或支链状的链烯或链二烯等)等。
作为脂环式烃,可举出例如:环丙烷、环丁烷、环戊烷、环己烷、环庚烷、环辛烷、环壬烷、环癸烷、环十二烷、环十四烷、环十六烷、环三十烷等环链烷烃[3~30元(优选5~30元、特别优选5~20元)的环链烷烃等];环丙烯、环丁烯、环戊烯、环辛烯、环己烯、环庚烯、环十二碳烯等环链烯[3~30元(优选3~20元、特别优选3~12元)的环链烯等];环戊二烯、1,3-环己二烯、1,5-环辛二烯等环链二烯;环辛三烯等环链三烯;十氢化萘、双环[2.2.0]己烷、双环[2.2.2]辛烷、双环[3.2.1]辛烷、双环[4.3.2]十一碳烷、双环[3.3.3]十一碳烷、降冰片烷、降冰片烯、三环[5.2.1.02,6]癸烷、三环[6.2.1.02,7]十一碳烷、金刚烷、全氢蒽、全氢苊、全氢菲、全氢非那烯、全氢茚等2~4环式的交联环式烃等。
作为芳香族烃,可举出例如:苯、萘、蒽等碳原子数6~20的芳香族烃等。
另外,所述烃作为取代基,可以具有选自脂肪族烃基、脂环式烃基及芳香族烃基中的1个或2个以上的基团。
作为脂肪族烃基,可举出从所述脂肪族烃的结构式中除去了1个或2个以上的氢原子的基团(1价或2价以上的脂肪族烃基)。作为1价的脂肪族烃基,可举出例如:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、辛基、癸基等碳原子数1~10的直链状或支链状的烷基;乙烯基、异丙烯基、1-丁烯基等碳原子数2~10的烯基;乙炔基、丙炔基等碳原子数2~10的炔基等。作为2价的脂肪族烃基,可举出例如:亚甲基、亚乙基、亚丙基、三亚甲基、异亚丙基、四亚甲基等碳原子数1~10的直链状或支链状的亚烷基等。作为3价的脂肪族烃基,可举出例如:1,2,3-丙烷甲苯基等碳原子数1~10的链烷甲苯基等。
作为脂环式烃基,可举出从所述脂环式烃的结构式中除去了1个或2个以上的氢原子的基团(1价或2价以上的脂环式烃基)。作为脂环式烃基,可举出例如:环戊基、环己基等环烷基;环戊烯基、环己烯基等环烯基;金刚烷-1-基、降冰片烷-2-基、降冰片烷-7,7-二基等交联环式烃基等。
作为芳香族烃基,可举出从所述芳香族烃的结构式中除去了1个或2个以上的氢原子的基团(1价或2价以上的芳香族烃基)。作为芳香族烃基,可举出例如:苯基、1-萘基、1,2-亚苯基、1,3-亚苯基、1,4-亚苯基等。
另外,在所述烃中包含以脂环式烃和芳香族烃共用2个碳原子的形式缩合成的化合物。作为这种化合物,可举出例如:茚满、四氢化萘、芴、苊等。
所述烃可以在不损害反应的范围内具有1个或2个以上的烃基以外的取代基,也可以不具有。
在本发明中,用作反应基质的烃的碳原子数没有特别限制,优选为2~30左右,更优选为3~25,进一步优选为4~20。
在本发明中,作为优选的烃,可举出:丙烷、丁烷、戊烷、己烷、庚烷、辛烷、壬烷、癸烷、十一碳烷、十二烷、十三烷、十四烷、十五烷、十六烷、十七烷、十八烷、十九烷、二十碳烷等直链状链烷(例如碳原子数3~30、优选4~20的直链状链烷烃等);2-甲基丙烷、2-甲基丁烷、2,2-二甲基丙烷、2-甲基戊烷、3-甲基戊烷、2,3-二甲基丁烷、2-甲基己烷、3-甲基己烷、3,4-二甲基己烷、3-甲基辛烷等支链状链烷烃(例如碳原子数3~30、优选4~20的支链状链烷等);环戊烷、环己烷等环链烷[3~30元(优选5~30元、特别优选5~20元)的环链烷等];甲苯、邻二甲苯、间二甲苯、对二甲苯、邻叔丁基甲苯、间叔丁基甲苯、对叔丁基甲苯、1-乙基-4-甲基苯、1-乙基-3-甲基苯、1-异丙基-4-甲基苯、1-叔丁基-4-甲基苯、均三甲苯、假枯烯、均四甲苯、甲基萘、二甲基萘、甲基蒽、4,4'-二甲基联苯、乙苯、丙苯、丁苯、1,4-二乙基苯等在芳香环上键合有1个或2个以上的烷基(例如碳原子数1~6的烷基等)的芳香族烃;四氢化萘、芴等以脂环式烃和芳香族烃共用2个碳原子的形式缩合成的化合物等。
特别是在本发明中,即使为用现有的方法难以有效地进行氧化的直链状链烷烃,也可以以高的收率进行氧化,因此,在使用直链状链烷作为基质的情况下,是特别有用的。
[氧化剂]
在本发明中,其特征在于,在臭氧的共存下使用作为氧化剂的氧。在本发明中,在氧和臭氧的存在下、或氧气和臭氧气体的流通下进行反应。通过将作为氧化剂的氧与臭氧一起使用,可以促进从基质(A)夺氢,可以使自由基反应活化。因此,在温和的条件下(反应压力:常压、反应温度:例如室温~200℃左右、优选50~130℃、特别优选60~100℃)下也可以促进氧化反应。在氧气和臭氧气体的流通下进行反应时,作为含臭氧气体的氧气中所占的臭氧气体量,从反应性及经济性的观点出发,为氧气的例如0.1~10体积%左右。
作为氧,优选使用分子状氧。作为分子状氧,可以使用纯粹的氧,也可以使用用氮、氦、氩、二氧化碳等非活性气体进稀释了的氧、或常压或加压(1~100气压)的空气。只要相对于1摩尔的作为基质的基质(A)分子状氧的使用量为1摩尔以上,就没有特别限定。
本发明中,臭氧具有作为自由基产生剂的作用。作为臭氧,优选使用臭氧气体。只要相对于1摩尔的基质(A)臭氧气体的使用量为0.01摩尔以上即可,没有特别限定。另外,只要反应顺利地进行,臭氧气体的供给可以间断地进行,也可以连续地进行。另外,作为自由基产生剂,可以与臭氧一起使用例如偶氮二异丁腈(AIBN)等。
[固体酸催化剂]
本发明的氧-臭氧共存下氧化用固体酸催化剂为过渡金属以单质、化合物或离子的形态担载于下述载体的催化剂,所述载体至少在表面具有哈米特的酸度函数(H0)为-9以下的强酸或超强酸。另外,本发明的氧-臭氧共存下氧化用固体酸催化剂可以为过渡金属以单质、化合物或离子的形态担载于下述载体的催化剂,所述载体至少在表面具有选自硫酸、硫酸化金属氧化物、贵金属/硫酸化金属氧化物、金属氧化物超强酸、及氟化磺酸类树脂中的至少1种强酸或超强酸。
作为所述哈米特的酸度函数(H0)为-9以下的强酸或超强酸,可举出例如:浓硫酸、固体强酸、固体超强酸[哈米特的酸度函数(H0)小于-11.93的酸]等。予以说明,如果浓硫酸的哈米特的酸度函数为96%,则H0=-9.88,如果为98%,则H0=-10.27,如果为100%,则H0=-11.93。
作为固体强酸或固体超强酸,可举出:将液体超强酸(例如SbF5、BF3、BF-SbF5、FSO3H-SbF5、TaF5等)担载于固体(例如Al2O3、SiO2、沸石、SiO2-Al2O3、聚合物、石墨、金属等)上而成的固定化液体超强酸;将AlCl3或AlBr3、和CuSO4、CuCl2、Ti2(SO4)3、或TiCl3通过磨碎混合而制备的二元金属盐;使硫酸离子吸附于金属氧化物(例如Fe2O3、TiO2、ZrO2、HfO2、SnO2、Al2O3、SiO2等)并进行烧成担载结合的硫酸化金属氧化物;向所述硫酸化金属氧化物添加了Ir、Pt等贵金属而形成的贵金属/硫酸化金属氧化物;使WO3、MoO3、B2O3等吸附于金属氧化物(例如ZrO2、SnO2、TiO2、Fe2O3等)、并在高温下进行烧成而成的金属氧化物超强酸;强酸性或超强酸性离子交换树脂(-CF3、CF2、SO3H等具有强酸基或超强酸基的非多孔质或多孔质离子交换树脂等);杂多酸(含有P、Mo、V、W、Si等元素的多酸等)等。作为所述强酸性或超强酸性离子交换树脂,可举出氟化磺酸类树脂(在侧链上具有含有磺酸基的基团的氟树脂)等。在优选的氟化磺酸类树脂中包含具有磺酸基的全氟乙烯基醚单体和四氟乙烯的共聚物[例如:“Nafion(注册商标)NR50”(Aldrich公司制造)、“Nafion(注册商标)H”(杜邦公司制造)等]等。
作为本发明中使用的载体,其中,优选硫酸化金属氧化物、贵金属/硫酸化金属氧化物、金属氧化物超强酸、强酸性或超强酸性离子交换树脂(氟化磺酸类树脂等),特别优选硫酸化金属氧化物、贵金属/硫酸化金属氧化物、氟化磺酸类树脂。由于硫酸化金属氧化物、贵金属/硫酸化金属氧化物、氟化磺酸类树脂的酸强度特别高,因此,可以更有效地担载过渡金属化合物。作为硫酸化金属氧化物,优选硫酸化氧化锆、硫酸化锡、硫酸化铪等,作为贵金属/硫酸化金属氧化物,优选Pt/硫酸化氧化锆、Ir/硫酸化氧化锆、Pd/硫酸化氧化锆等。其中,作为所述载体,可以优选使用工业上容易获得的硫酸化氧化锆、氟化磺酸类树脂。尤其是,作为所述载体,优选氟化磺酸类树脂(例如“Nafion(注册商标)”等具有磺酸基的全氟乙烯基醚单体和四氟乙烯的共聚物等)。
在所述“至少在表面具有哈米特的酸度函数(H0)为-9以下的强酸或超强酸的载体”中包含例如:(i)以哈米特的酸度函数(H0)为-9以下的强酸或超强酸其自身为载体的载体、(ii)在固体的表面形成有所述哈米特的酸度函数(H0)为-9以下的强酸或超强酸的覆膜的载体等。
作为所述(ii)中的固体,可举出例如:Al2O3、SiO2、沸石、SiO2-Al2O3、玻璃等无机氧化物(包含复合氧化物)、活性炭、石墨、金属等无机物质;树脂(聚合物)等。作为所述树脂,可举出例如:Teflon(注册商标)、PCTFE等氟类树脂、聚酯类树脂、聚烯烃类树脂、聚碳酸酯类树脂、聚苯乙烯类树脂、聚酰胺类树脂、聚酰亚胺类树脂等。
在本发明中,所述载体的形状或粒径没有特别限定,可以从颗粒状、粉末状、粒状、膜状、管状、作为其它固体催化剂通常所使用的形状中选择而使用。所述载体可以在流动反应器等反应器的内壁面作为覆膜而形成。
作为所述载体,特别优选在由氟化磺酸类树脂构成的颗粒或粉粒体、或固体[例如:树脂或无机物质(无机氧化物等)]的表面形成有氟化磺酸类树脂的覆膜的载体。
作为所述过渡金属,大多使用周期表第3~12族的金属元素。例如,作为所述金属元素,可举出:周期表第3族元素(Sc、镧系元素、锕系元素等)、第4族元素(Ti、Zr、Hf等)、第5族元素(V等)、第6族元素(Cr、Mo、W等)、第7族元素(Mn等)、第8族元素(Fe、Ru等)、第9族元素(Co、Rh等)、第10族元素(Ni、Pd、Pt等)、第11族元素(Cu等)、第12族元素(Zn等)等。在优选的金属元素中包含周期表第5~11族元素,可举出例如第5族~9族元素(Co、Mn、Fe、V、Mo等)。其中,优选Co、Mn、Fe、Zr、Ce、V、Mo、W,特别优选Co、Mn、Fe、Zr、V。金属元素的原子价没有特别限制,例如为0~6价左右,优选为2~5价,进一步优选为2~3价。
作为过渡金属化合物,可举出所述金属元素的单质、氢氧化物、氧化物(包含复合氧化物)、卤化物(氟化物、氯化物、溴化物、碘化物)、含氧酸盐(例如硝酸盐、硫酸盐、磷酸盐、硼酸盐、碳酸盐等)、同多酸的盐、杂多酸的盐等无机化合物;有机酸盐(例如乙酸盐、丙酸盐、氰酸盐、环烷酸盐、硬脂酸盐;甲烷磺酸盐、乙烷磺酸盐、辛烷磺酸盐、十二烷磺酸盐等烷基磺酸盐(例如C6-18烷基磺酸盐);可以用苯磺酸盐、对甲苯磺酸盐、萘磺酸盐、癸基苯磺酸盐、十二烷基苯磺酸盐等烷基取代的芳基磺酸盐(例如C6-18烷基-芳基磺酸盐);络合物等有机化合物。作为构成所述络合物的配体,可举出:OH(羟基)、烷氧基(甲氧基、乙氧基、丙氧基、丁氧基等)、酰基(乙酰基、丙酰基等)、烷氧基羰基(甲氧基羰基、乙氧基羰基等)、乙酰丙酮、环戊二烯基、卤素原子(氯、溴等)、CO、CN、氧原子、H2O(水)、膦(三苯基膦等三芳基膦等)的磷化合物、NH3(氨合物)、NO、NO2(亚硝酸根)、NO3(硝酸基)、乙二胺、二亚乙基三胺、吡啶、菲绕啉等含氮化合物等。
作为过渡金属化合物的具体例,例如以钴化合物为例时,可举出:氢氧化钴、氧化钴、氯化钴、溴化钴、硝酸钴、硫酸钴、磷酸钴等无机化合物;乙酸钴、环烷酸钴、硬脂酸钴等有机酸盐;乙酰丙酮钴等络合物等2价或3价的钴化合物等。另外,作为锰化合物的实例,可举出:氢氧化锰、氧化锰、氯化锰、硫酸锰等无机化合物;锰乙酰丙酮等络合物等2~5价的锰化合物等。作为其它过渡金属元素的化合物,可示例与所述钴或锰化合物对应的化合物等。过渡金属化合物可以单独或2种以上组合而使用。另外,优选将价数不同的多个过渡金属化合物(例如2价的金属化合物和3价的金属化合物)组合而使用。作为本发明中的过渡金属化合物,作为过渡金属,优选具有Co(钴)、Mn(锰)、Fe(铁)、Zr(锆)、Ce(铈)、V(钒)、Mo(钼)或W(钨)、特别优选具有Co、Mn、Fe、Zr或V的化合物,其中,优选钴化合物、锰化合物(特别钴化合物、锰化合物的有机酸盐),在可以抑制催化剂的活性降低方面,特别优选将钴化合物和锰化合物组合而使用。
另外,作为过渡金属离子,优选钴离子、锰离子、铁离子、锆离子、铈离子等,特别优选将钴离子、锰离子、或钴离子和锰离子组合而使用。
作为使过渡金属以单质、化合物或离子的形态担载于所述载体的方法,可以通过惯用的方法、例如含浸法、烧成法、沉淀法、离子交换法等而进行。予以说明,所述载体在流动反应器等反应器的内壁面以覆膜的形式形成的情况下,通过使过渡金属化合物的溶液在该反应器内流通,可以将过渡金属担载于载体。
作为过渡金属(单质、化合物或离子)的担载量,相对于所述载体,例如以过渡金属化合物等中的金属原子计为0.001~20重量%左右,优选为0.01~20重量%左右,特别为0.1~10重量%左右。另外,将利用过渡金属离子对载体进行离子交换的情况下,作为其离子交换量,相对于载体,例如以过渡金属离子中的金属原子计为0.001~20重量%左右,优选为0.01~20重量%左右,特别为0.1~10重量%左右。
[氧化物的制造方法]
本发明的氧化物的制造方法中,在所述固体酸催化剂的存在下,在氧及臭氧的共存下对所述基质(A)进行氧化。
在本发明中,可以使用溶剂,但也可以不使用溶剂。溶剂的使用量例如为基质(A)和该基质(A)的氧化物的总量为反应体系内的液体成分总量的70重量%以上左右、优选85重量%以上、特别优选95重量%以上的量。而且,在实质上不使用溶剂的情况下,不需要使作为反应生成物的氧化物和溶剂进行分离,可以消除制造工艺的繁杂。
作为所述溶剂,可举出例如:乙酸、丙酸等有机酸;乙腈、丙腈、苯甲腈等腈类;甲酰胺、乙酰胺、二甲基甲酰胺、二甲基乙酰胺等酰胺类;己烷、辛烷等脂肪族烃;氯仿、二氯甲烷、二氯乙烷、四氯化碳、氯苯、三氟甲基苯等卤化烃;硝基苯、硝基甲烷、硝基乙烷等硝基化合物;乙酸乙酯、乙酸丁酯等酯类;及这些混合溶剂等。
就所述固体酸催化剂的使用量(使用2种以上的情况下为其总量)而言,反应形式为间歇式的情况下,作为在该固体酸催化剂中担载于载体的过渡金属,相对于基质(A),例如为0.00001~10摩尔%左右,优选为0.2~2摩尔%。
[具有环状酰亚胺骨架的酰亚胺化合物]
在本发明中,为了更促进基质(A)的氧化反应,可以与所述固体酸催化剂一起使用具有环状酰亚胺骨架的酰亚胺化合物(以下,有时简称为“酰亚胺化合物”)。作为具有环状酰亚胺骨架的酰亚胺化合物,可举出例如下述式(I)表示的化合物。
[化学式1]
式(I)中,n表示0或1。X表示氧原子或-OR基(R表示氢原子或羟基的保护基)。氮原子和X之间的键为单键或双键。所述酰亚胺化合物在分子中可以具有多个式(I)表示的环状酰亚胺骨架。另外,所述酰亚胺化合物在所述X为-OR基且R为羟基的保护基的情况下,除环状酰亚胺骨架中的R之外的部分(N-氧基环状酰亚胺骨架)可以经由R而多个键合。
式(I)中,作为R所示的羟基的保护基,可举出例如:烷基(例如甲基、叔丁基等C1-4烷基等)、烯基(例如烯丙基等)、环烷基(例如环己基等)、芳基(例如2,4-二硝基苯基等)、芳烷基(例如苄基、2,6-二氯苄基、3-溴苄基、2-硝基苄基、三苯基甲基等);取代甲基(例如甲氧基甲基、甲基硫代甲基、苄氧基甲基、叔丁氧基甲基、2-甲氧基乙氧基甲基、2,2,2-三氯乙氧基甲基、双(2-氯乙氧基)甲基、2-(三甲基甲硅烷基)乙氧基甲基等)、取代乙基(例如1-乙氧基乙基、1-甲基-1-甲氧基乙基、1-异丙氧基乙基、2,2,2-三氯乙基、2-甲氧基乙基等)、四氢吡喃基、四氢呋喃基、可与1-羟基烷基(例如1-羟基乙基、1-羟基己基、1-羟基癸基、1-羟基十六烷基、1-羟基-1-苯基甲基等)的羟基形成缩醛或半缩醛基的基团等;酰基(例如甲酰基、乙酰基、丙酰基、丁酰基、异丁酰基、戊酰基、三甲基乙酰基、己酰基、庚酰基、辛酰基、壬酰基、癸酰基、月桂酰基、肉豆蔻酰基、棕榈酰基、硬脂酰基等C1-20脂肪族酰基等脂肪族饱和或不饱和酰基;乙酰乙酰基;环戊烷羰基、环己烷羰基等环链烷羰基等脂环式酰基;苯甲酰基、萘酰基等芳香族酰基等);磺酰基(甲烷磺酰基、乙烷磺酰基、三氟甲烷磺酰基、苯磺酰基、对甲苯磺酰基、萘磺酰基等)、烷氧基羰基(例如甲氧基羰基、乙氧基羰基、叔丁氧基羰基等C1-4烷氧基-羰基等)、芳烷基氧基羰基(例如苄基氧基羰基、对甲氧基苄基氧基羰基等)、取代或无取代氨基甲酰基(例如氨基甲酰基、甲基氨基甲酰基、苯基氨基甲酰基等)、从无机酸(硫酸、硝酸、磷酸、硼酸等)中除去了OH基的基团、二烷基硫膦基(例如二甲基硫膦基等)、二芳基硫膦基(例如二苯基硫膦基等)、取代甲硅烷基(例如三甲基甲硅烷基、叔丁基二甲基甲硅烷基、三苄基甲硅烷基、三苯基甲硅烷基等)。
另外,作为X为-OR基的情况下,作为除环状酰亚胺骨架中的R之外的部分(N-氧基环状酰亚胺骨架)经由R而多个键合时的R,可举出例如:草酰基、丙二酰基、琥珀酰基、戊二酰基、己二酰基、邻苯二甲酰基、间苯二甲酰基、对苯二甲酰基等聚羧酸酰基;羰基;亚甲基、乙叉基、异丙叉基、环戊叉基、环己叉基、苄叉基等多价的烃基(特别是与2个羟基形成缩醛键的基团)等。
优选的R中包含例如:氢原子;可与羟基形成缩醛或半缩醛基的基团;通过从羧酸、磺酸、碳酸、氨基甲酸、硫酸、磷酸、硼酸等酸中除去了OH基的基团(酰基、磺酰基、烷氧基羰基、氨基甲酰基等)的水解而可脱离的水解性保护基等。
式(I)中,n表示0或1。即,式(I)在n为0的情况下,表示5元的环状酰亚胺骨架,在n为1的情况下,表示6元的环状酰亚胺骨架。
作为所述酰亚胺化合物的代表的实例,可举出下述式(1)表示的酰亚胺化合物。
[化学式2]
式(1)中,n表示0或1。X表示氧原子或-OR基(R表示氢原子或羟基的保护基)。R1、R2、R3、R4、R5、及R6相同或不同,表示氢原子、卤原子、烷基、芳基、环烷基、羟基、烷氧基、羧基、取代氧羰基、酰基或酰氧基。R1、R2、R3、R4、R5、及R6中的至少2个可以相互键合而形成双键,可以与构成环状酰亚胺骨架的碳原子同时形成环。在所述R1、R2、R3、R4、R5、或R6、或R1、R2、R3、R4、R5、及R6中的至少2个相互键合而形成的双键、或与构成环状酰亚胺骨架的碳原子同时形成的环上,上述式(1)中所示的环状酰亚胺基可以进一步形成1个或2个以上。
式(1)表示的酰亚胺化合物的取代基R1、R2、R3、R4、R5、及R6中的卤原子中包含碘、溴、氯及氟原子。烷基中包含例如甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、己基、癸基、十二烷基、十四烷基、十六烷基等碳原子数1~30左右(特别是碳原子数1~20左右)的直链状或支链状烷基。
芳基中包含例如苯基、萘基等,环烷基中包含例如环戊基、环己基等。烷氧基中包含例如甲氧基、乙氧基、异丙氧基、丁氧基、叔丁氧基、己氧基、辛氧基、癸氧基、十二氧烷基、十四烷氧基、十八烷氧基等碳原子数1~30左右(特别是碳原子数1~20左右)的烷氧基。
取代氧羰基可举出例如:甲氧基羰基、乙氧基羰基、异丙氧基羰基、丁氧基羰基、叔丁氧基羰基、己基氧羰基、癸基氧羰基、十六烷基氧羰基等C1-30烷氧基-羰基(特别是C1-20烷氧基-羰基);环戊基氧羰基、环己基氧羰基等环烷基氧羰基(特别是3~20元环烷基氧羰基);苯基氧羰基、萘基氧羰基等芳基氧羰基(特别是C6-20芳氧基-羰基);苄基氧羰基等芳烷基氧羰基(特别是C7-21芳烷氧基-羰基)等。
酰基中例如包含甲酰基、乙酰基、丙酰基、丁酰基、异丁酰基、戊酰基、三甲基乙酰基、己酰基、辛酰基、癸酰基、月桂酰基、肉豆蔻酰基、棕榈酰基、硬脂酰基等C1-30脂肪族酰基(特别是C1-20脂肪族酰基)等脂肪族饱和或不饱和酰基;乙酰乙酰基;环戊烷羰基、环己烷羰基等环链烷羰基等脂环式酰基;苯甲酰基、萘酰基等芳香族酰基等。
酰氧基中包含例如甲酰氧基、乙酰氧基、丙酰氧基、丁酰氧基、异丁酰氧基、戊酰氧基、三甲基乙酰基、己酰氧基、辛酰氧基、癸酰氧基、月桂酰氧基、肉豆蔻酰氧基、棕榈酰氧基、硬脂酰基氧基等C1-30脂肪族酰氧基(特别是C1-20脂肪族酰氧基)等脂肪族饱和或不饱和酰氧基;乙酰乙酰基氧基;环戊烷羰氧基、环己烷羰基氧基等环链烷羰基氧基等脂环式酰氧基;苯甲酰氧基、萘酰氧基等芳香族酰氧基等。
作为所述取代基R1、R2、R3、R4、R5及R6中的至少2个相互键合,可以与构成环状酰亚胺骨架的碳原子一起形成的环,例如为5~12元环(特别优选6~10元环)。所述环中包含烃环、杂环、及缩合杂环。作为这种环的具体例,可以列举:非芳香族性脂环式环(环己烷环等可以具有取代基的环链烷环、环己烯环等可以具有取代基的环链烯环等)、非芳香族性交联环(5-降冰片烯环等可以具有取代基的交联式烃环等)、可以具有取代基的芳香族环(包含缩合环)(苯环、萘环等)。作为所述环可以具有的取代基,可举出例如:烷基、卤烷基、羟基、烷氧基、羧基、取代氧羰基、酰基、酰氧基、硝基、氰基、氨基、卤原子等。
在所述R1、R2、R3、R4、R5、或R6、或R1、R2、R3、R4、R5、及R6中的至少2个相互键合而形成的双键、或与构成环状酰亚胺骨架的碳原子一起形成的环上,可以进一步形成1个或2个以上上述式(1)中所示的环状酰亚胺基,例如R1、R2、R3、R4、R5、或R6为碳原子数2以上的烷基的情况下,可以含有构成该烷基的邻接的2个碳原子而形成所述环状酰亚胺基。另外,R1、R2、R3、R4、R5及R6中的至少2个相互键合而形成双键的情况下,可以含有该双键而形成所述环状酰亚胺基。并且,R1、R2、R3、R4、R5、及R6中的至少2个相互键合而与构成环状酰亚胺骨架的碳原子一起形成环的情况下,可以含有构成该环的邻接的2个碳原子而形成所述环状酰亚胺基。
优选的酰亚胺化合物中包含下述式表示的化合物。式中,R11~R16相同或不同,表示氢原子、卤原子、烷基、芳基、环烷基、羟基、烷氧基、羧基、取代氧羰基、酰基、或酰氧基。R17~R26相同或不同,表示氢原子、烷基、卤烷基、羟基、烷氧基、羧基、取代氧羰基、酰基、酰氧基、硝基、氰基、氨基、或卤原子。R17~R26可以邻接的基团彼此键合而形成式(1c)、(1d)、(1e)、(1f)、(1h)、或(1i)中所示的5元或6元的环状酰亚胺骨架。A表示亚甲基或氧原子。X与上述相同。
[化学式3]
作为取代基R11~R16中的卤原子、烷基、芳基、环烷基、羟基、烷氧基、羧基、取代氧羰基、酰基、酰氧基,可例示与所述R1~R6中的对应的基团同样的基团。
取代基R17~R26中,烷基可例示与上述例示的烷基同样的烷基(优选碳原子数1~6左右的烷基,特别优选碳原子数1~4的低级烷基),卤烷基可例示三氟甲基等碳原子数1~4左右的卤烷基,烷氧基可例示与上述同样的烷氧基(特别碳原子数1~4左右的低级烷氧基),取代氧羰基可例示与上述同样的取代氧羰基(烷氧基羰基、环烷基氧羰基、芳基氧羰基、芳烷基氧羰基等)。另外,作为酰基,可例示与上述同样的酰基(脂肪族饱和或不饱和酰基、乙酰乙酰基、脂环式酰基、芳香族酰基等),作为酰氧基,可例示与所述同样的酰氧基(脂肪族饱和或不饱和酰氧基、乙酰乙酰基氧基、脂环式酰氧基、芳香族酰氧基等)。作为卤原子,可例示氟、氯、溴原子。作为取代基R17~R26,特别优选氢原子、碳原子数1~4左右的低级烷基、羧基、取代氧羰基、硝基、卤原子。
另外,在本发明中,由于在臭氧共存下使用作为氧化剂的氧,因此,可以用非常优异的氧化力对基质(A)进行氧化。因此,即使在利用酰亚胺化合物的Fedors的方法得到的溶解度参数[SP值;构成酯键的氧原子(-O-)的蒸发能量为3350J/mol、摩尔体积成为3.8cm3/mol的温度(25℃)下的值]例如超过26[(MPa)1/2]的情况(优选超过26[(MPa)1/2]且为40[(MPa)1/2]以下的情况)下,也可以在无溶剂下使反应迅速地进行,可以有效地得到氧化物。另外,SP值可以通过文献记载的方法[R.F.Fedors,Polym.Eng.Sci.,14(2),147(1974);E.A.Grulke,Polymer Handbook,VII/675;原崎勇次、涂装技术、3、129(1987)参照]来求出。
作为优选的酰亚胺化合物中的具有5元的环状酰亚胺骨架的化合物的代表的实例,可举出:N-羟基琥珀酸酰亚胺、N-羟基-α-甲基琥珀酸酰亚胺、N-羟基-α,α-二甲基琥珀酸酰亚胺、N-羟基-α,β-二甲基琥珀酸酰亚胺、N-羟基-α,α,β,β-四甲基琥珀酸酰亚胺、N-羟基马来酸酰亚胺、N-羟基六氢邻苯二甲酰亚胺、N,N'-二羟基环己烷四羧酸二酰亚胺、N-羟基邻苯二甲酰亚胺、N-羟基四溴邻苯二甲酰亚胺、N-羟基四氯邻苯二甲酰亚胺、N-羟基氯桥酸酰亚胺、N-羟基腐植酸酰亚胺、N-羟基偏苯三酸酰亚胺、N,N'-二羟基均苯四甲酸二酰亚胺、N,N'-二羟基萘四羧酸二酰亚胺、α,β-二乙酰氧基-N-羟基琥珀酸酰亚胺、N-羟基-α,β-双(丙酰氧基)琥珀酸酰亚胺、N-羟基-α,β-双(戊酰氧基)琥珀酸酰亚胺、N-羟基-α,β-双(月桂酰氧基)琥珀酸酰亚胺、α,β-双(苯甲酰氧基)-N-羟基琥珀酸酰亚胺、N-羟基-4-甲氧基羰基邻苯二甲酰亚胺、4-乙氧基羰基-N-羟基邻苯二甲酰亚胺、N-羟基-4-戊基氧羰基邻苯二甲酰亚胺、4-十二烷氧基-N-羟基羰基邻苯二甲酰亚胺、N-羟基-4-苯氧基羰基邻苯二甲酰亚胺、N-羟基-4,5-双(甲氧基羰基)邻苯二甲酰亚胺、4,5-双(乙氧基羰基)-N-羟基邻苯二甲酰亚胺、N-羟基-4,5-双(戊基氧羰基)邻苯二甲酰亚胺、4,5-双(十二烷基氧羰基)-N-羟基邻苯二甲酰亚胺、N-羟基-4,5-双(苯氧基羰基)邻苯二甲酰亚胺等式(1)中的X为-OR基且R为氢原子的化合物;与这些化合物对应、R为乙酰基、丙酰基、苯甲酰基等酰基的化合物;N-甲氧基甲基氧基邻苯二甲酰亚胺、N-(2-甲氧基乙氧基甲氧基)邻苯二甲酰亚胺、N-四氢吡喃氧基邻苯二甲酰亚胺等式(1)中的X为-OR基且R为可与羟基形成缩醛或半缩醛键的基团的化合物;N-甲烷磺酰氧基邻苯二甲酰亚胺、N-(对甲苯磺酰氧基)邻苯二甲酰亚胺等式(1)中的X为-OR基且R为磺酰基的化合物;N-羟基邻苯二甲酰亚胺的硫酸酯、硝酸酯、磷酸酯或硼酸酯等式(1)中的X为-OR基且R为从无机酸中除去了OH基的基团的化合物等。
作为优选的酰亚胺化合物中的6元的具有环状酰亚胺骨架的化合物的代表的实例,可举出:N-羟基戊二酰亚胺、N-羟基-α,α-二甲基戊二酰亚胺、N-羟基-β,β-二甲基戊二酰亚胺、N-羟基-1,8-十氢化萘二羧酸酰亚胺、N,N'-二羟基-1,8;4,5-十氢化萘四羧酸二酰亚胺、N-羟基-1,8-萘二羧酸酰亚胺(N-羟基萘二甲酰亚胺)、N,N'-二羟基-1,8;4,5-萘四羧酸二酰亚胺等式(1)中的X为-OR基且R为氢原子的化合物;与这些化合物对应的、R为乙酰基、丙酰基、苯甲酰基等酰基的化合物;N-甲氧基甲基氧基-1,8-萘二羧酸酰亚胺、N,N'-双(甲氧基甲基氧基)-1,8;4,5-萘四羧酸二酰亚胺等式(1)中的X为-OR基且R为可与羟基形成缩醛或半缩醛键的基团的化合物;N-甲烷磺酰氧基-1,8-萘二羧酸酰亚胺、N,N'-双(甲烷磺酰氧基)-1,8;4,5-萘四羧酸二酰亚胺等式(1)中的X为-OR基且R为磺酰基的化合物;N-羟基-1,8-萘二羧酸酰亚胺或N,N'-二羟基-1,8;4,5-萘四羧酸二酰亚胺的硫酸酯、硝酸酯、磷酸酯或硼酸酯等式(1)中的X为-OR基且R为从无机酸中除去了OH基的基团的化合物等。
所述酰亚胺化合物中,X为-OR基且R为氢原子的化合物(N-羟基酰亚胺化合物)可以通过惯用的酰亚胺化反应,例如,使对应的酸酐和羟基胺反应,经过酸酐基的开环及闭环而进行酰亚胺化的方法来制造。另外,所述酰亚胺化合物中,X为-OR基且R为羟基的保护基的化合物可以通过在对应的R为氢原子的化合物(N-羟基酰亚胺化合物)中利用惯用的保护基导入反应导入所期望的保护基来制造。例如,N-乙酰氧基邻苯二甲酰亚胺可以通过使乙酸酐与N-羟基邻苯二甲酰亚胺反应,或在碱的存在下使乙酰基卤化物反应来制造。
特别优选的酰亚胺化合物包含:由脂肪族多价羧酸酐或芳香族多价羧酸酐所衍生的N-羟基酰亚胺化合物(例如N-羟基琥珀酸酰亚胺(SP值:33.5[(MPa)1/2])、N-羟基邻苯二甲酰亚胺(SP值:33.4[(MPa)1/2])、N,N'-二羟基均苯四甲酸二酰亚胺、N-羟基戊二酰亚胺、N-羟基-1,8-萘二羧酸酰亚胺、N,N'-二羟基-1,8;4,5-萘四羧酸二酰亚胺等)、及通过向所述N-羟基酰亚胺化合物的羟基中导入保护基而得到的化合物等。
酰亚胺化合物可以单独使用1种,或组合2种以上而使用。所述酰亚胺化合物可以在反应体系内生成,但在本发明中,例如可以优选使用商品名“N-Hydroxyphthalimide”(和光纯药工业株式会社制造)、商品名“N-Hydroxysuccinimide”(和光纯药工业株式会社制造)等市售品。
另外,酰亚胺化合物可以以担载于载体(例如活性炭、沸石、二氧化硅、二氧化硅-氧化铝、膨润土等多孔载体)的形态使用。
相对于基质(A)1摩尔,酰亚胺化合物的使用量例如为0.0000001~1摩尔左右,优选为0.00001~0.5摩尔,特别优选为0.0001~0.4摩尔。通过在上述范围内使用酰亚胺化合物,可以以优异的反应速度使氧化反应进行。
[金属化合物]
予以说明,在本发明中,为了更加提高反应速度,可以与所述固体酸催化剂一起使用金属化合物(但是,相当于上述固体酸催化剂的物质除外)。
作为构成金属化合物的金属元素,可以列举例如、钴、锰、锆及钼。金属元素的原子价没有特别限制,例如为0~6价左右。
作为金属化合物,可举出:所述金属元素的单质、氢氧化物、氧化物(包含复合氧化物)、卤化物(氟化物、氯化物、溴化物、碘化物)、含氧酸盐(例如硝酸盐、硫酸盐、磷酸盐、硼酸盐、碳酸盐等)、同多酸的盐、杂多酸的盐等无机化合物;有机酸盐(例如乙酸盐、丙酸盐、氰酸盐、环烷酸盐、硬脂酸盐等)、络合物等有机化合物。
作为构成所述络合物的配体,可举出:OH(羟基)、烷氧基(甲氧基、乙氧基、丙氧基、丁氧基等)、酰基(乙酰基、丙酰基等)、烷氧基羰基(甲氧基羰基、乙氧基羰基等)、乙酰丙酮、环戊二烯基、卤素原子(氯、溴等)、CO、CN、氧原子、H2O(水)、膦(三苯基膦等三芳基膦等)的磷化合物、NH3(氨合物)、NO、NO2(亚硝酸根基)、NO3(硝酸基)、乙二胺、二亚乙基三胺、吡啶、菲绕啉等含氮化合物等。
作为金属化合物的具体例,例如以钴化合物为例时,可举出:氢氧化钴、氧化钴、氯化钴、溴化钴、硝酸钴、硫酸钴、磷酸钴等无机化合物;乙酸钴、环烷酸钴、硬脂酸钴等有机酸盐;乙酰丙酮钴等络合物等2价或3价的钴化合物等。作为其它金属元素的化合物,可例示与所述钴化合物对应的化合物。金属化合物可以单独使用1种,或组合2种以上而使用。在本发明中,在可以显著地提高反应速度方面,优选至少使用钴化合物,特别优选组合钴化合物和锰化合物而使用。
相对于基质(A),金属化合物的使用量(使用2种以上的情况为其总量)例如为0.00001~10摩尔%左右,优选为0.2~2摩尔%。另外,就金属化合物的使用量而言,使用所述酰亚胺化合物的情况下,相对于所述酰亚胺化合物1摩尔,例如为0.001~10摩尔左右,优选为0.005~3摩尔,特别优选为0.01~1摩尔。
[氧化反应]
在本发明中,氧化反应中的反应温度可以根据基质(A)的种类或目标生成物的种类等而适当选择,例如,为室温~200℃左右,优选为50~130℃,特别优选为60~100℃。反应可以在常压或加压下进行,在加压下进行反应的情况下,通常为0.1~10MPa左右(优选0.15~8MPa、特别优选0.5~8MPa)。在本发明中,将作为氧化剂的氧与臭氧一起使用,因此,即使在常压(0.1MPa)下也可以使氧化反应顺利地进行。
反应时间可以根据反应温度及压力而适当调整,例如为0.1~20小时左右,优选为1~10小时。
氧化反应可以利用间歇式、半间歇式、连续式等惯用的方法而进行。使用上述酰亚胺化合物的情况下,将该酰亚胺化合物在体系内逐次地添加时,可以以更高的转化率对基质进行氧化,有时可以以更高的选择率得到氧化物。
通过反应,生成与用于反应的基质(A)对应的氧化物,例如醇、酮、醛、羧酸、氢过氧化物等。予以说明,作为基质(A),使用在杂原子的邻位上具有碳-氢键的含杂原子的化合物(A1)的情况下,容易生成该杂原子的邻位的碳原子被氧化的化合物。在使用具有碳-杂原子双键的化合物(例如含羰基的化合物)(A2)的情况下,容易生成涉及该碳-杂原子双键的碳原子(例如羰基碳原子)被氧化的化合物。在使用具有次甲基碳原子的化合物(A3)的情况下,容易生成该次甲基碳原子被氧化的化合物。使用在不饱和键的邻位上具有碳-氢键的化合物(A4)的情况下,容易生成涉及该碳-氢键的碳原子被氧化的化合物。在使用脂环式化合物(A5)的情况下,容易生成构成脂环的碳原子被氧化的化合物。在使用共轭化合物(A6)的情况下,容易生成构成共轭双键的碳原子被氧化的化合物。在使用胺化合物(A7)的情况下,容易生成构成氨基的氮原子或其邻位的碳原子被氧化的化合物。在使用芳香族化合物(A8)的情况下,构成芳香环的碳原子容易被氧化,在芳香环上键合有烃基的情况下,容易生成与芳香环邻接的部位的碳原子被氧化的化合物。在使用直链状链烷烃(A9)的情况下,末端的碳原子容易被氧化,但有时亚甲基碳原子被氧化。在使用烯烃(A10)的情况下,有时与碳-碳双键有关的碳原子或其邻位的碳原子容易被氧化,环氧化合物生成。
反应结束后,氧化物例如可以通过过滤、浓缩、蒸馏、萃取、晶析、再结晶、柱色谱等分离手段、或组合有这些方法的分离手段而进行分离提纯。
根据本发明的方法,可以在温和的条件下使基质(A)(例如可以为直链状链烷烃等难以氧化的基质)迅速地进行氧化而有效地制造对应的氧化物(含氧化合物等)。另外,为了提高反应速度,使用具有环状酰亚胺骨架的酰亚胺化合物的情况下,即使相对于基质(例如烃等)使用溶解性低的酰亚胺化合物(例如SP值超过26的酰亚胺化合物),也实质上在无溶剂下,迅速地进行氧化反应。
实施例
以下,通过实施例更具体地说明本发明,但本发明并不受这些实施例限定。
实施例1
在30mL三口烧瓶中放入乙酸钴四水合物0.300g(以钴计0.071g)、及乙酸锰四水合物0.293g(以锰计0.066g),加入乙酸10.0g,制成均匀溶液。加入有Nafion颗粒(商品名“Nafion”、杜邦公司制造、氟化磺酸类树脂)3.00g,在100℃下搅拌8小时。过滤固体,用乙酸30mL清洗。接着,使用乙酸乙酯30mL、二乙基醚30mL依次清洗,然后,在130℃下减压干燥5小时,由此得到担载有钴及锰的Nafion颗粒3.17g。
为了研究上述中得到的钴及锰担载Nafion颗粒中的钴及锰的担载量,进行以下的操作。采取少量得到的钴及锰担载Nafion颗粒,在室温下浸于10重量%稀硝酸水溶液,使其静置一夜,由此使担载的金属全部溶出至水相。用ICP分析水相的金属浓度,以该值为基础计算钴及锰在Nafion颗粒的担载量,结果为钴2.0wt%、锰1.9wt%。
实施例2
在内径2.0mm、长度1.5m的Teflon(注册商标)制管的内部,使20重量%Nafion分散液(杜邦公司制造)流动,在约100℃下进行干燥,由此制作在内壁上形成有厚度0.5mm的Nafion覆膜的Teflon(注册商标)制管(内径1.0mm)。在该管内,使乙酸钴[Co(OAc)2]的5重量%乙酸溶液流动,在约100℃下加热1小时后,在120℃下进行干燥,由此制作在内壁上形成有用钴离子进行了离子交换的超强酸性离子交换树脂(氟化磺酸类树脂)覆膜的流动反应器。利用ICP发光分析法测定超强酸性离子交换树脂覆膜中的钴浓度,结果为2.4重量%。
实施例3
在备有气体通气管线及插入管的100mL的SUS制耐压反应器(耐压硝子工业株式会社制造、TVS-1型)中,加入N-羟基邻苯二甲酰亚胺(以后有时称为“NHPI”、SP值:33.4[(MPa)1/2])0.808g(4.95毫摩尔、基质的10.0摩尔%)、十四烷[东京化成工业株式会社制造]10.0g(50.4毫摩尔),然后,固定于油浴而连接气体通气线。在使用臭氧产生装置(商品名“SG-01-PSA2”、住友精密工业株式会社制造)产生的含有臭氧气体的空气(氧含量:20.7体积%、臭氧气体含量:0.3体积%)开始向反应器内的液体鼓泡(1000mL/分钟)、开始进行反应器的加热而内温达到90℃的时刻,添加实施例1中制作的钴及锰担载Nafion颗粒0.635g(钴2.0wt%、锰1.9wt%)并开始反应。使用气体色谱(柱:007-FFAP)对在90℃下经过8小时的时刻的十四烷转化率进行测定,结果为4.9%。另外,生成十四醇、十四酮、十四烷酸。
比较例1
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例3同样地进行,结果,基质转化率为0.4%。
实施例4
除不使用NHPI之外,与实施例3同样地进行,结果,基质转化率为2.9%。
实施例5
将基质由十四烷变更为2,2,4-三甲基戊烷,除此之外,与实施例3同样地进行,结果,基质转化率为6.4%。另外,生成4-羟基-2,2,4-三甲基戊烷、新戊基醇、丙酮。
比较例2
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例5同样地进行,结果,基质转化率为0.5%。
实施例6
除将基质由十四烷变更为正庚烷之外,与实施例3同样地进行,结果,基质转化率为4.9%。另外,生成2-羟基庚烷、2-庚酮、2,6-庚烷二酮。
比较例3
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例6同样地进行,结果,基质转化率为0.4%。
实施例7
除将基质由十四烷变更为甲苯之外,与实施例3同样地进行,结果,基质转化率为33%。另外,生成苄醇、苯甲醛、苯甲酸。
比较例4
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例7同样地进行,结果,基质转化率为2.6%。
实施例8
除将基质由十四烷变更为环己烷(833毫摩尔)之外,与实施例3同样地进行,结果,基质转化率为8%。另外,生成环己酮、环己醇。
比较例5
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例8同样地进行,结果,基质转化率为1.0%。
实施例9
除将基质由十四烷变更为环己烯(889毫摩尔)之外,与实施例3同样地进行,结果,基质转化率为10%。另外,生成2,3-环己烯-1-醇、2,3-环己烯-1-酮。
比较例6
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例9同样地进行,结果,基质转化率为1.3%。
实施例10
除将基质由十四烷变更为异色满(716毫摩尔)之外,与实施例3同样地进行,结果,基质转化率为14%。另外,生成3,4-二氢异香豆素。
比较例7
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例10同样地进行,结果,基质转化率为1.7%。
实施例11
将基质由十四烷变更为异丙苯(647毫摩尔),反应结束后添加硫酸,除此之外,与实施例3同样地进行,结果,基质转化率为11%。另外,生成苯酚。
比较例8
使用不含有臭氧气体的空气代替含有臭氧气体的空气,除此之外,与实施例11同样地进行,结果,基质转化率为1.5%。
工业实用性
根据本发明,由于将基质在特定的固体酸催化剂的存在下且在氧和臭氧的共存下进行氧化,因此,氧化速度显著地提高,可以将广泛的基质以高的转化率进行氧化。另外,即使基质为烃,特别是直链状链烷,也可以以高的收率得到氧化物(含氧化合物等)。
Claims (8)
1.一种氧-臭氧共存下氧化用固体酸催化剂,其是在氧和臭氧的共存下对下述基质(A)进行氧化时使用的氧化反应用固体酸催化剂,其中,
过渡金属以单质、化合物或离子的形态担载于至少在表面具有哈米特的酸度函数(H0)为-9以下的强酸或超强酸的载体,
基质(A)选自下述的化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
2.一种氧-臭氧共存下氧化用固体酸催化剂,其是在氧和臭氧的共存下对下述基质(A)进行氧化时使用的氧化反应用固体酸催化剂,其中,
过渡金属以单质、化合物或离子的形态担载于下述的载体,所述载体至少在表面具有选自硫酸、硫酸化金属氧化物、贵金属/硫酸化金属氧化物、金属氧化物超强酸、及氟化磺酸类树脂中的至少1种强酸或超强酸,
基质(A)选自下述的化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
3.如权利要求1或2所述的固体酸催化剂,其中,基质(A)为烃。
4.如权利要求1~3中任一项所述的固体酸催化剂,其中,所述载体为由氟化磺酸类树脂形成的颗粒或粉粒体,或者为在固体表面上形成有氟化磺酸类树脂的覆膜的载体。
5.如权利要求1~4中任一项所述的固体酸催化剂,其中,所述过渡金属为选自钴、锰、钒、铁、锆、钨及钼中的至少1种。
6.如权利要求1~5中任一项所述的固体酸催化剂,其中,形状为颗粒状、膜状或管状。
7.一种氧化物的制造方法,其包括在权利要求1~6中任一项所述的固体酸催化剂的存在下,在氧及臭氧的共存下对下述基质(A)进行氧化,
基质(A)选自化合物:(A1)在杂原子的邻位上具有碳-氢键的化合物、(A2)具有碳-杂原子双键的化合物、(A3)具有次甲基碳原子的化合物、(A4)在不饱和键的邻位上具有碳-氢键的化合物、(A5)脂环式化合物、(A6)共轭化合物、(A7)胺化合物、(A8)芳香族化合物、(A9)直链状链烷烃、及(A10)烯烃。
8.如权利要求7所述的氧化物的制造方法,其进一步包括在具有环状酰亚胺骨架的酰亚胺化合物的存在下对基质进行氧化。
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JPS61118343A (ja) * | 1984-11-12 | 1986-06-05 | Agency Of Ind Science & Technol | カルボン酸及びカルボン酸誘導体の製造方法 |
US5731456A (en) * | 1996-12-13 | 1998-03-24 | Eastman Chemical Company | Preparation of vinyl acetate |
JP3773824B2 (ja) * | 2001-03-12 | 2006-05-10 | 独立行政法人科学技術振興機構 | 高分子担持型アリールビス(パーフルオロアルキルスルホニル)メタン |
JP5524602B2 (ja) * | 2009-12-25 | 2014-06-18 | 三洋化成工業株式会社 | 固体酸触媒 |
JP5869436B2 (ja) * | 2011-07-22 | 2016-02-24 | 株式会社日本触媒 | 3−ヒドロキシカルボン酸又はそのエステルの脱水用触媒の再生方法、及び、(メタ)アクリル酸又はそのエステルの製造方法 |
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2015
- 2015-07-31 CN CN201580044244.2A patent/CN106660032A/zh active Pending
- 2015-07-31 JP JP2016545405A patent/JPWO2016031491A1/ja active Pending
- 2015-07-31 US US15/507,000 patent/US20170253575A1/en not_active Abandoned
- 2015-07-31 KR KR1020177004594A patent/KR20170046653A/ko unknown
- 2015-07-31 WO PCT/JP2015/071827 patent/WO2016031491A1/ja active Application Filing
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WO2016031491A1 (ja) | 2016-03-03 |
JPWO2016031491A1 (ja) | 2017-06-08 |
KR20170046653A (ko) | 2017-05-02 |
US20170253575A1 (en) | 2017-09-07 |
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