CN102596876A - 酮的制造方法 - Google Patents
酮的制造方法 Download PDFInfo
- Publication number
- CN102596876A CN102596876A CN201080047735XA CN201080047735A CN102596876A CN 102596876 A CN102596876 A CN 102596876A CN 201080047735X A CN201080047735X A CN 201080047735XA CN 201080047735 A CN201080047735 A CN 201080047735A CN 102596876 A CN102596876 A CN 102596876A
- Authority
- CN
- China
- Prior art keywords
- copper
- ketone
- manufacture
- catalyzer
- reaction
- 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
Links
- 150000002576 ketones Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000010949 copper Substances 0.000 claims abstract description 11
- 229910052802 copper Inorganic materials 0.000 claims abstract description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 33
- 150000001879 copper Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 10
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002191 fatty alcohols Chemical class 0.000 claims description 8
- 239000011651 chromium Substances 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 17
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229910017813 Cu—Cr Inorganic materials 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910001297 Zn alloy Inorganic materials 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 229910002058 ternary alloy Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/294—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with hydrogen peroxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/85—Chromium, molybdenum or tungsten
- C07C2523/88—Molybdenum
- C07C2523/885—Molybdenum and copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
本发明涉及酮的制造方法,其中,使用铜类催化剂,在0.1MPaG以下的反应压力下将脂族醇脱氢。
Description
技术领域
本发明涉及使用铜类催化剂的酮的制造方法。
背景技术
酮类是作为溶剂和有机化学品的原料有用的物质。特别地,甲乙酮(MEK、2-丁酮)是无色透明的吸湿性液体,具有优异的溶解能力,与一般使用的有机溶剂自由地混合。特别是对合成树脂、油脂、高级脂肪酸等的溶解能力大,在溶剂领域得到广泛的利用。近年来,在磁带粘合剂用等电子产业领域中也有需求将其作为高性能溶剂。
MEK合成法中有仲丁醇(SBA、2-丁醇)的脱氢、正丁烯或正丁烷的氧化、环氧丁烷的异构化等,不过工业上以通过SBA的脱氢反应进行的合成法为主流。
将SBA的脱氢反应分类为使用Cu、Zn、Cr等金属氧化物为催化剂的气相法和使用海绵Ni催化剂的液相法。由于气相法反应温度高(通常为300℃-400℃),尽管SBA转化率高(80%以上),但存在MEK选择率低(95%-99%左右)、催化剂寿命短的缺点。另一方面,由于液相法的反应温度低(通常为130℃-200℃),尽管SBA转化率变低,但存在MEK选择率高(99.5%以上)、催化剂寿命长的优点。
专利文献1公开了使用在海绵(雷尼,Ranney)Ni中添加有Cu、Ag、Au、Sn、Pb、Zn、Cd、In、Ge等金属的催化剂,于170℃-230℃进行反应的方法,专利文献2公开了使用海绵Ni催化剂在160℃-190℃、2气压-8气压下进行反应的方法。
另外,专利文献3公开了使用将铜、锌及铝三元合金活化(展開develop)而获得的球状改性雷尼铜催化剂,对仲醇脱氢的酮类制造方法。进而,专利文献4公开了使用将铜、锌及铁合金活化而获得的改性雷尼铜催化剂,对伯醇或仲醇脱氢的羰基化合物制造方法。
尽管用这些技术也可以得到某种程度上纯度良好的MEK,但由于电子产业领域等要求超过99.95%的极高纯度,因此需要制造高纯度MEK的技术。
现有技术文献
专利文献
专利文献1:美国专利第4380673号说明书
专利文献2:日本特开昭60-258135号公报
专利文献3:日本特开平7-53433号公报
专利文献4:日本特开平7-316089号公报
发明内容
本发明的目的是提供制造高纯度酮的方法。
根据本发明,提供以下的酮的制造方法。
1.酮的制造方法,其中,使用铜类催化剂,在0.1MPaG以下的反应压力下将脂族醇脱氢。
2.1所述的酮的制造方法,其中,上述铜类催化剂为含有铜和铬或者铜和锌的氧化物固体催化剂。
3.1所述的酮的制造方法,其中,上述铜类催化剂为海绵铜类催化剂。
4.1-3中任一项所述的酮的制造方法,其中,如下进行上述脱氢:在200℃以下的反应温度下,向悬浮有上述铜类催化剂的溶剂中连续注入上述脂族醇。
5.1-4中任一项所述的酮的制造方法,其中,上述脂族醇为2-丁醇。
6.1-5中任一项所述的酮的制造方法,其中,上述酮为甲乙酮。
根据本发明,提供了制造高纯度酮的方法。
具体实施方式
本发明的酮的制造方法使用铜类催化剂将脂族醇脱氢而制造酮。
作为原料脂族醇,优选仲醇。作为仲醇,可以使用2-丙醇、2-丁醇,优选2-丁醇。
生成的酮为丙酮、甲乙酮等,尤其为甲乙酮。
铜类催化剂优选以铜以及铬(Cr)或锌(Zn)为主成分。为了提高催化剂的耐久性等,可以添加钡(Ba)、钙(Ca)、锰(Mn)、氧化铝(Al2O3)、氧化硅(SiO2)等。
另外,铜类催化剂可以列举将铜和铝等的合金活化处理而制备的海绵铜类催化剂。
作为脱氢反应,可以列举使用固定床管型流通反应器的气相法;使用搅拌槽型反应器将催化剂颗粒悬浮在高沸点溶剂中,向其中连续注入醇使其反应的液相法等,优选液相法。
优选反应温度在130℃以上且在200℃以下。不到130℃时,在反应速度和化学平衡(平衡转化率)方面有可能降低反应效率。超过200℃时,有可能变得易于进行副反应而降低选择率(制品纯度)。另外,还有可能使催化剂劣化变得易于进展、增大催化剂再生和更换的频率,导致经济性变差。更优选在135℃以上且在170℃以下,进一步优选在140℃以上且不到150℃.
脱氢反应的反应压力在0.1MPaG以下。从化学平衡方面考虑,低压更为有利。优选在0.05MPaG以下,更优选在0.03MPaG以下。下限可以是常压,也可以是大于0MPaG。溶剂中的催化剂浓度没有特别限制,不过从操作性、效率方面,优选1wt%-30wt%。
溶剂优选高沸点溶剂。优选使用在反应条件下蒸气压低的饱和烃,特别优选沸点在200℃-400℃左右的碳原子数12-30左右的链烷烃类。溶剂过于轻质时,由于容易在反应条件下挥发,有可能增大溶剂回收、再循环的负荷。相反,过于重质时,由于粘度变高,有可能在搅拌、混合方面降低反应效率。
以基于重量的重时空速(WHSV)计,相对于催化剂载入量的原料醇供给量通常为1-30h-1。超过30h-1时,有反应速度下降、制品收率(生产性)变差之虞,不足1h-1时,有经济性和生产性下降之虞。
本发明的方法中,抑制氢化裂解等副反应,从而抑制丙酮、异丙醇等副产物的生成,因此选择性率高,可以制造高纯度的酮。例如即使使选择率在99.95%以上也是可能的。此外,由于可以抑制副反应,使生成的氢气中的杂质(甲烷、乙烷、丙烷、丁烷等)减少,还可以得到高纯度的氢气。
实施例
实施例1
在内容积500cc的四口烧瓶中装入市售的海绵铜催化剂(川研フアインケミカル(株)制造CDT-60,经活化处理,Al:1%)24g,用2-丁醇(SBA)置换数次。加入异链烷烃165cc,安装搅拌器、原料(SBA)供应管、生成液提取用冷却管,用氮气置换。在1000rpm下搅拌的同时用覆套式加热器加热烧瓶,将SBA以120cc/h(96g/h)的流量供应,使烧瓶内的液温为145℃、反应压力为0.01MPaG。生成的甲乙酮(MEK)、未反应的SBA和副产物(异丙醇、丙酮等)通过冷却管冷凝而连续提取,产生的氢气由通风管排出。WHSV为4h-1。
几天后在活性稳定的状态下,用气相色谱法(GC-FID)分析生成液,通过以下式求得转化率和选择率。式中[面积]表示由色谱峰面积定量的量。SBA转化率为30%,MEK选择率为99.99%。结果在表1中显示。
[数学式1]
分析条件如下所示。
使用仪器:Agilent Technologies 6850GC
柱:HP-INNOWAX(长度60m、内径0.25mm、膜厚0.25μm)、He2.0ml/min。
注入口:250℃、分流(Split)1/250
烘箱:60℃下保持10分钟,再以15℃/分的比例升温至240℃为止。
检测器:FID,250℃
实施例2
除了代替实施例1中使用的催化剂使用市售的铜铬催化剂(日揮触媒化成(株)制造N203S,化学组成:CuO46%、Cr2O344%、MnO24%)以外,与实施例1同样地进行反应、分析。MEK选择率为99.99%。结果在表1中显示。
实施例3
除了反应温度为165℃以外,与实施例1同样地进行反应、分析。尽管转化率提高,但MEK选择率没有下降,为99.99%。结果在表1中显示。
实施例4
除了代替实施例1中使用的催化剂使用市售的铜锌催化剂(日揮触媒化成(株)制造E01X,化学组成:CuO46%、ZnO48%、Al2O36%)以外,与实施例1同样地进行反应、分析。MEK选择率为99.99%。结果在表1中显示。
比较例1
除了代替实施例1中使用的催化剂,使用市售的海绵Ni催化剂(日興リカ(株)制造,经活化处理,Al/Ni=8%)以外,与实施例1同样地进行反应、分析。MEK选择率为99.90%。结果在表1中显示。
与比较例1相比,实施例1-4使用铜类催化剂,因此进一步减少副产物,实现了高的MEK选择率,可以制造极高纯度的MEK。
[表1]
工业实用性
本发明的方法制造的酮可以适合地用作溶剂和有机化合物的原料等。
上文详细说明了几个本发明的实施方案和/或实施例,不过本领域技术人员在不实质背离本发明的新颖教导和效果的情况下,可容易地对例示的实施方案和/或实施例进行多种改变。因而,这类多种改变包含在本发明的范围内。
将本说明书中所述文献的内容全部援引至本文中。
Claims (6)
1.酮的制造方法,其中,使用铜类催化剂,在0.1MPaG以下的反应压力下将脂族醇脱氢。
2.权利要求1所述的酮的制造方法,其中,所述铜类催化剂为含有铜和铬或者铜和锌的氧化物固体催化剂。
3.权利要求1所述的酮的制造方法,其中,所述铜类催化剂为海绵铜类催化剂。
4.权利要求1-3中任一项所述的酮的制造方法,其中,如下进行所述脱氢:在200℃以下的反应温度下,向悬浮有所述铜类催化剂的溶剂中连续注入所述脂族醇。
5.权利要求1-4中任一项所述的酮的制造方法,其中,所述脂族醇为2-丁醇。
6.权利要求1-5中任一项所述的酮的制造方法,其中,所述酮为甲乙酮。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009244328 | 2009-10-23 | ||
JP2009-244328 | 2009-10-23 | ||
PCT/JP2010/006127 WO2011048783A1 (ja) | 2009-10-23 | 2010-10-15 | ケトンの製造方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN102596876A true CN102596876A (zh) | 2012-07-18 |
Family
ID=43900028
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080047735XA Pending CN102596876A (zh) | 2009-10-23 | 2010-10-15 | 酮的制造方法 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP5615834B2 (zh) |
KR (1) | KR101762979B1 (zh) |
CN (1) | CN102596876A (zh) |
MY (1) | MY165490A (zh) |
WO (1) | WO2011048783A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101320532B1 (ko) | 2011-12-01 | 2013-10-22 | 지에스칼텍스 주식회사 | 이성분계 반응시스템을 활용한 메틸에틸케톤의 합성방법 |
CN106117025B (zh) * | 2016-06-23 | 2019-04-05 | 九江齐鑫化工有限公司 | 仲丁醇对醋酸仲丁酯转移加氢同时生产甲乙酮的工艺方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50130708A (zh) * | 1974-04-04 | 1975-10-16 | ||
US4380673A (en) * | 1980-06-26 | 1983-04-19 | Institut Francais Du Petrole | Catalyst and process for manufacturing a ketone by dehydrogenation of a secondary alcohol |
JPH05168928A (ja) * | 1991-12-17 | 1993-07-02 | Kao Corp | 脱水素反応用触媒及び該触媒の製造法、並びに該触媒を使用するカルボニル化合物の製造法 |
JPH0753433A (ja) * | 1993-08-20 | 1995-02-28 | Showa Denko Kk | ケトン類の製造方法 |
JPH11199539A (ja) * | 1998-01-08 | 1999-07-27 | New Japan Chem Co Ltd | 脂環式ジケトン化合物の製造方法 |
US20040002620A1 (en) * | 2000-06-28 | 2004-01-01 | Albrecht Schwerin | Method for producing aldehydes |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2485519A1 (fr) * | 1980-06-26 | 1981-12-31 | Inst Francais Du Petrole | Procede pour la fabrication de cetones par deshydrogenation d'alcools secondaires |
JPH07316089A (ja) * | 1994-05-26 | 1995-12-05 | Showa Denko Kk | カルボニル化合物の製造方法 |
-
2010
- 2010-10-15 MY MYPI2012700143A patent/MY165490A/en unknown
- 2010-10-15 CN CN201080047735XA patent/CN102596876A/zh active Pending
- 2010-10-15 JP JP2011537126A patent/JP5615834B2/ja active Active
- 2010-10-15 KR KR1020127007540A patent/KR101762979B1/ko active IP Right Grant
- 2010-10-15 WO PCT/JP2010/006127 patent/WO2011048783A1/ja active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50130708A (zh) * | 1974-04-04 | 1975-10-16 | ||
US4380673A (en) * | 1980-06-26 | 1983-04-19 | Institut Francais Du Petrole | Catalyst and process for manufacturing a ketone by dehydrogenation of a secondary alcohol |
JPH05168928A (ja) * | 1991-12-17 | 1993-07-02 | Kao Corp | 脱水素反応用触媒及び該触媒の製造法、並びに該触媒を使用するカルボニル化合物の製造法 |
JPH0753433A (ja) * | 1993-08-20 | 1995-02-28 | Showa Denko Kk | ケトン類の製造方法 |
JPH11199539A (ja) * | 1998-01-08 | 1999-07-27 | New Japan Chem Co Ltd | 脂環式ジケトン化合物の製造方法 |
US20040002620A1 (en) * | 2000-06-28 | 2004-01-01 | Albrecht Schwerin | Method for producing aldehydes |
Also Published As
Publication number | Publication date |
---|---|
JP5615834B2 (ja) | 2014-10-29 |
KR20120089656A (ko) | 2012-08-13 |
WO2011048783A1 (ja) | 2011-04-28 |
JPWO2011048783A1 (ja) | 2013-03-07 |
MY165490A (en) | 2018-03-23 |
KR101762979B1 (ko) | 2017-08-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7812200B2 (en) | Process for preparing 1,2-propanediol by hydrogenolysis of glycerol | |
US8058484B2 (en) | Flexible glycerol conversion process | |
EP3207004A1 (en) | Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons | |
CN106866360B (zh) | 一种5-羟甲基糠醛催化转化制备1,6-己二醇的方法 | |
Dummer et al. | Oxidative dehydrogenation of cyclohexane and cyclohexene over supported gold, palladium and gold–palladium catalysts | |
JP6800206B2 (ja) | グリセロールのアリルアルコールへの直接脱酸素脱水素反応のためのレニウム含有担持不均一系触媒の使用 | |
US7868212B2 (en) | Method for preparing 1,2-propanediol by hydrogenolysis of glycerol | |
CN106866331B (zh) | 一种由糠醇制备环戊二烯或双环戊二烯的方法 | |
CN108892607B (zh) | 一种羟基香茅醛的制备方法 | |
CN106866345B (zh) | 一种由糠醇制备jp-10航空燃料的方法 | |
JP5784742B2 (ja) | フェニルシクロヘキサンの製造方法 | |
CN102596876A (zh) | 酮的制造方法 | |
CN105384616A (zh) | 甲氧基丙酮的合成方法 | |
CN107043319B (zh) | 制备甲醇的方法 | |
CN111939915A (zh) | 由丙醛一步合成丙酸丙酯用催化剂及其方法 | |
CN107903182B (zh) | 一种2-氨基-4-乙酰氨基苯甲醚的合成方法 | |
US4247726A (en) | Para-xylene process and catalyst | |
US20110071323A1 (en) | Method For Producing 1,2-Propanediol By Hydrogenolysis Of Glycerin | |
CN104529730A (zh) | 一种由2-戊烯制备3-戊酮的方法 | |
JP2585737B2 (ja) | テルペンアルコ―ルの製造方法 | |
CN105669598A (zh) | 一种α-蒎烯烯丙位选择性氧化方法及其产品 | |
CN104447255A (zh) | 一种由2-戊烯制备2-戊酮的方法 | |
JPS58157728A (ja) | 同時にアセチレン化合物類、カルボニル化合物類及び適宜ジオレフイン類を水素化により広く除去しながらi−ブテンを接触反応させる方法 | |
US9926245B2 (en) | Fuels and chemicals from lower alkanes | |
CN103980160B (zh) | 一种合成异佛尔酮二氨基甲酸甲酯的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C05 | Deemed withdrawal (patent law before 1993) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120718 |