CN101309749A - 氢化羰基化合物的催化剂和方法 - Google Patents
氢化羰基化合物的催化剂和方法 Download PDFInfo
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- CN101309749A CN101309749A CNA2006800253511A CN200680025351A CN101309749A CN 101309749 A CN101309749 A CN 101309749A CN A2006800253511 A CNA2006800253511 A CN A2006800253511A CN 200680025351 A CN200680025351 A CN 200680025351A CN 101309749 A CN101309749 A CN 101309749A
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- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000003054 catalyst Substances 0.000 title claims description 87
- 150000001728 carbonyl compounds Chemical class 0.000 title description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000000463 material Substances 0.000 claims abstract description 46
- 239000010949 copper Substances 0.000 claims abstract description 38
- 229910052802 copper Inorganic materials 0.000 claims abstract description 35
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000004568 cement Substances 0.000 claims abstract description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000010439 graphite Substances 0.000 claims abstract description 20
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 20
- 229910052742 iron Inorganic materials 0.000 claims abstract description 17
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract description 17
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 16
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 16
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 16
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 16
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 16
- 239000011733 molybdenum Substances 0.000 claims abstract description 16
- 229910052718 tin Inorganic materials 0.000 claims abstract description 16
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 16
- 239000010936 titanium Substances 0.000 claims abstract description 16
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 16
- 239000010937 tungsten Substances 0.000 claims abstract description 16
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 16
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 13
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 48
- 230000003647 oxidation Effects 0.000 claims description 38
- 238000007254 oxidation reaction Methods 0.000 claims description 38
- 238000005984 hydrogenation reaction Methods 0.000 claims description 23
- -1 adipate ester Chemical class 0.000 claims description 17
- 238000001354 calcination Methods 0.000 claims description 17
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 10
- 229960004643 cupric oxide Drugs 0.000 claims description 10
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 229910052748 manganese Inorganic materials 0.000 claims description 9
- 239000011572 manganese Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 239000001361 adipic acid Substances 0.000 claims description 5
- 235000011037 adipic acid Nutrition 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 abstract 2
- 239000005751 Copper oxide Substances 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract 1
- 229910001887 tin oxide Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 206010013786 Dry skin Diseases 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 4
- 239000000292 calcium oxide Substances 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940051250 hexylene glycol Drugs 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 238000009938 salting Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- FMBAIQMSJGQWLF-UHFFFAOYSA-N 2-ethyl-3-hydroxyhexanal Chemical compound CCCC(O)C(CC)C=O FMBAIQMSJGQWLF-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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- 239000012876 carrier material Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
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- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Abstract
本发明涉及氢化具有至少一个羰基的有机化合物的方法,其中在氢气存在下使该有机化合物与可根据如下方法生产的成形体接触:(i)提供包含氧化铜和氧化铝以及至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物以及任选的氧化锡和/或氧化锰的氧化材料,(ii)向氧化材料中加入粉状金属铜、铜片、粉状水泥、石墨或其混合物,(iii)将由(ii)得到的混合物成形为成形体,和(iv)用水或蒸汽处理成形体。
Description
本发明涉及使用催化剂氢化具有至少一个羰基的有机化合物的方法,所用催化剂尤其具有的特征为包含氧化铜、氧化铝和至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物,并且用沸水和/或蒸汽处理获得具有高选择性和同时具有高稳定性的催化剂。在其生产过程中,可额外加入铜粉、铜片或水泥。
羰基化合物例如羧酸或羧酸酯的催化氢化在通用化学工业生产流程中占有重要地位。
羰基化合物例如羧酸酯的催化氢化作用在工业过程中几乎只在固定床反应器中进行。所用的固定床催化剂除了阮内型催化剂外,特别是负载型催化剂,例如铜、镍或贵金属催化剂。
US 3,923,694例如描述了氧化铜/氧化锌/氧化铝型催化剂。该催化剂的不足在于其在反应过程中没有足够的机械稳定性并且因此相对较快地分解。由于催化剂成形体分解,这导致活性的损失和跨反应器差压的积累。因此设备不得不过早关闭。
DE 198 09 418.3描述了在催化剂存在下催化氢化羰基化合物的方法,所述催化剂包含主要含二氧化钛的载体以及作为活性组分的铜或铜与至少一种选自锌、铝、铈、贵金属和过渡族VIII金属的金属的混合物,其中铜的表面积不超过10m2/g。优选的载体材料为二氧化钛与氧化铝或氧化锆或氧化铝和氧化锆的混合物。在优选的实施方案中,添加金属铜粉或铜片并使催化剂材料成型。
DE-A 195 05 347非常概括地描述了具有高机械强度的催化剂片剂的方法,其中在待压片的材料中添加金属粉末或金属合金粉末。添加的金属粉末包括铝粉或铜粉或铜片。然而,在添加铝粉的情况下,用氧化铜/氧化锌/氧化铝催化剂获得的成形体比未添加铝粉制备的成形体具有更差的侧抗碎强度,并且当该发明的成形体用作催化剂时,其比未添加铝粉生产的催化剂具有更差的转化活性。该发明同样公开了一种由NiO、ZrO2、MoO3和CuO组成的催化剂,其中已经在生产过程中向该催化剂中添加了包括铜粉的材料。然而,该文件没有对选择性或活性做任何评述。
DE 256 515描述了由合成气制备醇的方法,其中使用了基于Cu/Al/Zn的催化剂,该催化剂通过一起研磨和制丸金属铜粉或铜片获得。所述方法主要强调C1-C5醇混合物的制备,选择这样的方法,其中反应器在床的上三分之一包括具有较高比例铜粉或铜片的催化剂,在床的下三分之一包括具有较低比例铜粉或铜片的催化剂。
JP-A 50-99987描述了通过水或蒸汽处理提高可基于铜的特定阮内催化剂的机械稳定性。SU-A 728 908公开了通过水处理使用于甲醇合成的铝-铜-锌催化剂硬化。两个文件都没有对选择性或活性做任何评述。
本发明的目的是提供不具有现有技术缺点的方法及催化剂并且提供催化氢化羰基化合物的方法及催化剂,所述催化剂同时具有高机械稳定性和高氢化活性和选择性。
已发现同时沉淀铜、铝化合物以及合适的话额外的铁、镧、钨、钼、钛、锆、锡和/或锰的化合物,随后干燥、煅烧、压片,并添加金属铜粉、铜片或水泥粉末或石墨或混合物获得这样的催化剂,其借助水和/或蒸汽处理既导致高活性和高选择性又导致用作催化剂的成形体的高稳定性。
相应地,本发明涉及氢化具有至少一个羰基的有机化合物的方法,其中在氢气存在下,使该有机化合物与可在如下方法中生产的成形体接触:
(i)提供包含氧化铜和氧化铝以及至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物的氧化材料,
(ii)可向氧化材料中加入粉状金属铜、铜片、粉状水泥、石墨或其混合物,
(iii)将由(ii)得到的混合物成形为成形体,并且
(iv)用沸水和/或蒸汽处理成形体。
氧化铁应理解为铁(III)氧化物。
在优选实施方案中,本发明的成形体以未负载催化剂、浸渍催化剂、涂覆催化剂和沉淀催化剂的形式使用。
在本发明方法中使用的催化剂具有的特征在于:铜活性组分、铝组分和至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物组分优选用碳酸钠溶液同时或者依次沉淀,随后干燥,煅烧,压片和再次煅烧。
特别地,下列沉淀方法适用:
A)铜盐溶液,铝盐溶液和铁、镧、钨、钼、钛、锆、锡或锰的盐溶液,或包含铜、铝,并含铁、镧、钨、钼、钛、锆、锡或锰的盐的溶液用碳酸钠溶液平行或依次沉淀。沉淀的材料随后干燥,并且合适的话,煅烧。
B)将铜盐溶液和铁、镧、钨、钼、钛、锆、锡或锰的盐溶液,或包含铜盐和至少一种铁盐的溶液在预制的氧化铝载体上沉淀。在特别优选的实施方案中,其以水悬浮液中的粉末形式存在。然而,载体材料也可以球体、挤出物、碎料或片剂的形式存在。
B1)在一个实施方案(I)中,铜盐溶液和铁、镧、钨、钼、钛、锆、锡或锰的盐溶液,或包含铜盐和铁、镧、钨、钼、钛、锆、锡或锰的盐的溶液优选用碳酸钠溶液沉淀。所用的初始进料为氧化铝载体材料的水悬浮液。
通常将由A)或B)得到的沉淀固体过滤并优选洗涤以除去碱,例如如DE 198 09 418.3所述。
来自A)和B)的终产物均在50-150℃,优选120℃的温度干燥,随后,合适的话,在通常为200-600℃,特别是300-500℃优选煅烧2小时。
用于A)和/或B)的起始物原则上可以是可溶于施用中所用溶剂的所有Cu(I)盐和/或Cu(II)盐,例如硝酸盐、碳酸盐、醋酸盐、草酸盐或铵配合物、类似的铝盐和铁盐。对于A)和B)的方法,特别优选使用硝酸铜。
在本发明方法中,上述经干燥和合适的话煅烧的粉末优选加工成片剂、环、环形片剂、挤出物、蜂窝或类似的成形体。为此,可以使用现有技术中的所有合适方法。特别优选使用具有<5mm的直径d和高度h的催化剂成形体或催化剂挤出物,具有<6mm的直径d的催化剂球体或具有<5mm的孔径rz的催化剂蜂窝。
氧化材料的组成通常使得氧化铜的比例在40-90重量%范围内,铁、镧、钨、钼、钛、锆、锡或锰的氧化物的比例在0-50重量%范围内,氧化铝的比例在至多50重量%范围内,在每种情况下基于上述氧化成分总和的总重量,煅烧后这三种氧化物一起构成氧化材料的至少80重量%,在上述意义中的氧化材料不包括水泥。
在优选的实施方案中,本发明因此涉及如上所述的方法,其中氧化材料包含:
(a)比例在50≤x≤80重量%,优选55≤x≤75重量%范围内的氧化铜,
(b)比例在15≤y≤35重量%,优选20≤y≤30重量%范围内的氧化铝,和
(c)比例在1≤z≤30重量%,优选2≤z≤25重量%范围内的至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物,
在每种情况下基于煅烧后氧化材料总重量,其中80≤x+y+z≤100,尤其是95≤+y+z≤100。
本发明方法和催化剂的显著特征在于,通过沸水和/或蒸汽对成形体进行处理,实现了用作催化剂的成形体的高稳定性,并且同时提高了催化剂的氢化活性和选择性。
对于水处理,上述已干燥并煅烧的成形体用足以完全覆盖催化剂的量的水或具有C1-C4醇如甲醇、乙醇或丁醇的水-醇溶液覆盖。水-醇溶液具有的最大醇浓度为30重量%。当使用水时,借助诸如硝酸、硫酸或盐酸的无机酸或碳酸钠或氢氧化钠溶液将pH调节为4-9,优选6-8.5。在100-140℃,和1-30巴,优选1-3巴的压力下,用水或水-醇溶液处理催化剂1-48小时,优选5-20小时。
蒸汽处理可以用100%蒸汽、由蒸汽和惰性气体如氮气组成且其中惰性气体比例为至多90重量%的蒸气混合物和/或在蒸汽处理的反应条件下在其中形成水的化合物的蒸气进行,所述化合物例如为C1-C4醇,如甲醇、乙醇或丁醇且醇的比例不超过90重量%。优选用纯的蒸汽进行蒸汽处理。
在100-300℃,优选100-150℃下用蒸汽处理催化剂体,通常在标准压力下进行,也可以在1-20巴,优选1-2巴的高压下进行。蒸汽处理通常进行至少1小时;优选10-48小时的处理时间。
在水和/或蒸汽处理后,将催化剂成形体在120℃的温度下再次干燥,优选在通常为5-300℃下干燥2小时并且合适的话煅烧。
通常地,粉状铜、铜片或粉状水泥或石墨或其混合物以1-40重量%,优选2-20重量%,更优选3-10重量%加入氧化材料中,在每种情况下基于氧化材料总重量。
所用的水泥优选为高铝水泥。高铝水泥更优选基本由氧化铝和氧化钙组成,更优选含有约75至85重量%的氧化铝和约15至25重量%的氧化钙。另外,也可使用基于氧化镁/氧化铝、氧化钙/氧化硅和氧化钙/氧化铝/氧化铁的水泥。
特别地,氧化材料可含有基于氧化材料总重量为最多10重量%,优选最多5重量%的至少一种选自元素Re、Fe、Ru、Co、Rh、Ir、Ni、Pd和Pt的另外组分。
在本发明方法的另一个优选实施方案中,除了铜粉、铜片或水泥粉末或其混合物外,在氧化材料成形为成形体之前还向其中添加石墨。优选加入足量的石墨以使成形体的成形可更好地进行。在优选的实施方案中,基于氧化材料总重量,添加0.5-5重量%的石墨。石墨在铜粉、铜片或水泥粉末或其混合物之前、之后还是同时加入氧化材料中并不重要。
相应地,本发明还涉及如上所述的方法,其中石墨以基于氧化材料总重量为0.5-5重量%的比例加入氧化材料或由(ii)得到的混合物中。
在优选的实施方案中,本发明因此还涉及用沸水和/或蒸汽处理的成形体,该成形体包含
氧化材料,该氧化材料包含:
(a)比例在50≤x≤80重量%,优选55≤x≤75重量%范围内的氧化铜,
(b)比例在15≤y≤35重量%,优选20≤y≤30重量%范围内的氧化铝,和
(c)比例在1≤z≤30重量%,优选2-25重量%范围内的至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物,
在每种情况下基于煅烧后氧化材料总重量,其中80≤x+y+z≤100,尤其是95≤x+y+z≤100,
金属铜粉、铜片或水泥粉末或其混合物,基于氧化材料总重量的比例在1-40重量%范围内,
石墨,基于氧化材料总重量的比例为0.5-5重量%,
氧化材料,金属铜粉、铜片或水泥粉末或其混合物和石墨的比例之和合计达到成形体的至少95重量%。
在向氧化材料添加铜粉、铜片或水泥粉末或其混合物以及合适的话石墨之后,合适的话,将成形后得到的成形体经通常0.5-10小时,优选0.5-2小时的时间煅烧至少一次。在该至少一次煅烧步骤中的温度通常在200-600℃范围内,优选在250-500℃范围内,更优选在270-400℃范围内。
在用水泥粉末成形的情况下,可有利的是在煅烧前用水润湿所得成形体,随后将其干燥。
在以氧化形式用作催化剂的情况下,在用氢化溶液进料之前,将成形体用还原气体,例如氢气,优选氢气-惰性气体混合物,尤其是氢气/氮气混合物,于100-500℃范围内,优选150-350℃范围内的温度,特别是在180-200℃范围内的温度下预还原。优选使用氢气含量在1-100体积%范围内,更优选在1-50体积%范围内的混合物。
在优选的实施方案中,发明的成形体在用作催化剂之前以本身已知的方式通过用还原介质处理来活化。活化预先在还原炉中进行或者在安装在反应器中之后进行。当反应器已预先在还原炉中活化时,将其安装在反应器中并在氢气压力下直接用氢化溶液进料。
通过本发明方法制备的成形体的优选应用领域为在固定床中氢化具有羰基的有机化合物。然而,其他实施方案同样是可能的,例如催化剂材料向上和向下运动的流化反应。氢化可以在气相或液相中进行。优选在液相中,例如以滴流模式或液相模式进行氢化反应。
以滴流模式运行使得包含待氢化的羰基化合物的液体反应物在处于氢气压力下的反应器中滴流过其中的催化剂床,在催化剂上形成了液体薄膜。与之不同,当以液相模式运行时,将氢气引入充满液体反应混合物的反应器中,氢气以上升的气泡通过催化剂床。
在一个实施方案中,待氢化的溶液以单程泵送通过催化剂床。在本发明方法的另一个实施方案中,将一部分产物在通过反应器后以产物流连续排出,合适的话,使其通过如上定义的第二个反应器后。将产物的其他部分与包含羰基化合物的新鲜反应物一起供回到反应器中。以下将该程序称为循环模式。
作为本发明方法的实施方案,当选择滴流模式时,此处优选循环模式。进一步优选使用主反应器和后反应器的循环模式运行。
本发明方法适于将羰基化合物,例如醛和酮、羧酸、羧酸酯或羧酸酐氢化成相应的醇,优选脂族和脂环族、饱和和不饱和羰基化合物。在芳族羰基化合物的情况下,可能会由于芳环氢化而形成不希望的副产物。羰基化合物可带有其它官能团如羟基或氨基。不饱和羰基化合物通常氢化成相应的饱和醇。在本发明上下文中使用的术语“羰基化合物”包括所有具有C=O基团的化合物,包括羧酸和它们的衍生物。应理解的是,还可以一起氢化两种或超过两种羰基化合物的混合物。每种待氢化的羰基化合物也可以包含超过一个羰基基团。
优选使用本发明方法氢化脂族醛、羟基醛、酮、酸、酯、酸酐、内酯和糖。
优选的脂族醛是支化和未支化的,饱和和/或不饱和的脂族C2-C30醛,如例如可由具有内双键或端双键的线性或支化烯烃通过羰基合成得到。也可氢化还包含超过30个羰基基团的低聚化合物。
脂族醛的实例包括:
甲醛、丙醛、正丁醛、异丁醛、戊醛、2-甲基丁醛、3-甲基丁醛(异戊醛)、2,2-二甲基丙醛(新戊醛)、己醛、2-甲基戊醛、3-甲基戊醛、4-甲基戊醛、2-乙基丁醛、2,2-二甲基丁醛、3,3-二甲基丁醛、辛醛、癸醛、戊二醛。
除提到的短链醛外,长链脂族醛也尤其适合,如例如可由线性烯烃通过羰基合成得到。
特别优选烯醛化(enalization)产物,如2-乙基己烯醛、2-甲基戊烯醛、2,4-二乙基辛烯醛或2,4-二甲基庚烯醛。
优选的羟基醛为C3-C12羟基醛,如例如可由脂族和脂环族醛和酮与其本身或甲醛进行醇醛缩合反应得到。实例为3-羟基丙醛、二羟甲基乙醛、三羟甲基乙醛(季戊四醛)、3-羟基丁醛(丁间醇醛)、3-羟基-2-乙基己醛(butylaldol)、3-羟基-2-甲基戊醛(propionaldol)、2-羟甲基丙醛、2,2-二羟甲基丙醛、3-羟基-2-甲基丁醛、3-羟基戊醛、2-羟甲基丁醛、2,2-二羟甲基丁醛、羟基新戊醛。特别优选羟基新戊醛(HPA)和二羟甲基丁醛(DMB)。
优选的酮为丙酮、丁酮、2-戊酮、3-戊酮、2-己酮、3-己酮、环己酮、异佛尔酮、甲基异丁基酮、异亚丙基丙酮、苯乙酮、苯基丙基甲酮、二苯甲酮、亚苄基丙酮、二亚苄基丙酮、亚苄基乙酰苯、2,3-丁二酮、2,4-戊二酮、2,5-己二酮和甲基乙烯基酮。
也可转化羧酸及其衍生物,优选具有1-20个碳原子的那些。特别应提及:
羧酸类,例如甲酸、乙酸、丙酸、丁酸、异丁酸、正戊酸、三甲基乙酸(新戊酸)、己酸、庚酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、丙烯酸、甲基丙烯酸、油酸、反油酸、亚油酸、亚麻酸、环己烷甲酸、苯甲酸、苯乙酸、邻甲基苯甲酸、间甲基苯甲酸、对甲基苯甲酸、邻氯苯甲酸、对氯苯甲酸、邻硝基苯甲酸、对硝基苯甲酸、水杨酸、对羟基苯甲酸、邻氨基苯甲酸、对氨基苯甲酸、草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸;
羧酸酯类,例如上述羧酸的C1-C10烷基酯,尤其是甲酸甲酯,乙酸乙酯,丁酸丁酯,邻苯二甲酸二烷基酯、间苯二甲酸二烷基酯、对苯二甲酸二烷基酯、己二酸二烷基酯、马来酸二烷基酯,例如这些酸的二甲酯,(甲基)丙烯酸甲酯,丁内酯,己内酯和聚羧酸酯,例如聚丙烯酸和聚甲基丙烯酸酯和它们的共聚物和聚酯,例如聚甲基丙烯酸甲酯,对苯二甲酸酯和其它工程塑料,此情况下,特别进行氢解,即将酯转化为相应的酸和醇;
脂肪类;
羧酸酐类,例如上述羧酸的酐,特别是乙酸酐、丙酸酐、苯甲酸酐和马来酸酐;
羧酰胺类,例如甲酰胺、乙酰胺、丙酰胺、硬脂酰胺、对苯二甲酰胺。
也可转化羟基羧酸,例如乳酸、苹果酸、酒石酸或柠檬酸,或氨基酸,例如甘氨酸、丙氨酸、脯氨酸和精氨酸,和肽。
特别优选的待氢化有机化合物为饱和或不饱和的羧酸、羧酸酯、羧酸酐或内酯或其两种或更多种的混合物。
相应地,本发明还涉及如上所述的方法,其中有机化合物为羧酸、羧酸酯、羧酸酐或内酯。
这些化合物的实例包括马来酸、马来酸酐、琥珀酸、琥珀酸酐、己二酸、6-羟基己酸、2-环十二烷基丙酸、上述酸的酯,例如甲酯、乙酯、丙酯或丁酯。其它实例为γ-丁内酯和己内酯。
在非常特别优选的实施方案中,本发明涉及如上所述的方法,其中有机化合物为己二酸或己二酸酯。
待氢化的羰基化合物可单独或作为与氢化反应产物的混合物进料到氢化反应器中,这种情况下可以以未稀释形式进行或使用额外的溶剂进行。合适的额外溶剂特别是水,醇如甲醇、乙醇和在反应条件下形成的醇。优选的溶剂为水、THF和NMP;特别优选水。
滴流模式和液相模式的氢化(各自优选以循环模式进行)都通常在50-350℃,优选在70-300℃,更优选在100-270℃范围内的温度下,在3-350巴,优选5-330巴,更优选10-300巴范围内的压力下进行。
在非常特别优选的实施方案中,本发明的催化剂在制备己二醇和/或己内酯的方法中使用,如DE 196 07 954、DE 196 07 955、DE 196 47 348和DE 196 47 349所述。
使用本发明催化剂的本发明方法实现了高转化率和高选择性。同时,本发明催化剂具有高化学和机械稳定性。
本发明因此非常普遍地涉及在催化剂制备中用沸水和/或蒸汽处理来同时提高催化剂的机械稳定性和活性及选择性的用途。
在优选的实施方案中,本发明涉及如上所述的用途,其中催化剂包含作为活性组分的铜。
固态催化剂,尤其是本发明催化剂的机械稳定性,通过在各种状态(氧化态、已还原、已还原并在水下悬浮)下的侧抗碎强度参数来描述。
实施例
实施例1:催化剂1的制备
将12.41kg 57%的硝酸铜溶液和12.78kg 33%的硝酸铝溶液和0.48kg40%的硝酸镧·6H2O溶液的混合物溶于2L水中(溶液1)。溶液2包含60kg20%的无水Na2CO3。将溶液1和溶液2经由分开的管线输入装配有搅拌器且包含10L加热到80℃的水的沉淀容器中。在此过程中,通过适当调节溶液1和溶液2的进料速率使pH达到6.2。
在保持pH恒定在6.2且温度在60℃的同时,将整个溶液1与碳酸钠反应。随后将由此形成的悬浮液再搅拌1小时,在此过程中,通过偶尔加入稀硝酸或苏打溶液2使pH达到7.2。过滤悬浮液并用蒸馏水洗涤直到洗涤水的硝酸根含量<10ppm。
将滤饼在120℃干燥16小时,随后在600℃煅烧2小时。使由此得到的催化剂粉末与1重量%的石墨预压制。得到的压制材料与5重量%的Unicoat铜片混合,随后与2重量%的石墨混合,并且压成直径3mm和高度3mm的片剂。最后,将片剂在350℃煅烧2小时。
由此制备的催化剂具有的化学组成为:
58%CuO/22%Al2O3/5%La2O3/15%Cu。
如表1中所示,侧抗碎强度为25N。
实施例2:催化剂2的水处理
将20g根据实施例1的催化剂与50mL水混合并在140℃,2巴的压力下加热24小时。在去除水后,将催化剂在120℃干燥4小时。
实施例3:催化剂3的蒸汽处理
将20g根据实施例1的催化剂在140℃和1.3巴下用100%的蒸汽处理20小时。然后,将催化剂在120℃干燥4小时。
实施例4:
Südchemie出售的催化剂T4489,组成为:
60%CuO/30%Al2O3/10 MnO2。
实施例5:蒸汽处理
将组成为60%CuO/30%Al2O3/10MnO2的市售催化剂(商品名T4489,来自Südchemie)用100%蒸汽在1.3巴的压力下处理20小时,然后在120℃干燥4小时。
实施例6:在催化剂1、2、3、4或5上氢化己二酸甲酯
在每种情况下已装填有200ml催化剂1、2、3、4或5的立管式反应器中,在200巴的压力和210巴1和190℃的反应温度下,以0.3kg/(L*h)的时空间速率将己二酸二甲酯以具有循环(进料/循环比=10/1)的滴流模式连续氢化。实验持续总共7天。GC分析检测,在190℃的反应器流出物中,酯转化率为99.9%,己二醇选择性为97.5%。在卸载后,催化剂仍然完全保持并且具有高的机械稳定性。实验结果汇总在表1中。
以下表1中的数据表明,本发明的催化剂相对于对比催化剂在190℃具有显著更高的氢化活性,即更高的己二酸二甲酯转化率,以及更高的有价值产物的选择性,即流出物中的目标产物己二醇的含量更高。
表1
催化剂实施例 | 反应温度[℃] | 己二酸二甲酯转化率[%] | 己二醇选择性[%] | 侧抗碎强度(N) |
催化剂1(未处理) | 210 | 98.09 | 96.46 | 25 |
催化剂2(水) | 210 | 99.57 | 97.34 | 54 |
催化剂3(蒸汽) | 210 | 99.52 | 97.82 | 41 |
催化剂4(未处理) | 190 | 90.05 | 96.66 | 22 |
催化剂5(蒸汽) | 190 | 92.8 | 97.1 | 34 |
Claims (11)
1.氢化具有至少一个羰基的有机化合物的方法,其中在氢气存在下使该有机化合物与可在如下方法中生产的成形体接触:
(i)提供包含氧化铜和氧化铝以及至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物的氧化材料,
(ii)向氧化材料中加入粉状金属铜、铜片、粉状水泥、石墨或其混合物,
(iii)将由(ii)得到的混合物成形为成形体,并且
(iv)用沸水和/或蒸汽处理成形体。
2.根据权利要求1的方法,其中氧化材料包含:
(a)比例在50≤x≤80重量%,优选55≤x≤75重量%范围内的氧化铜,
(b)比例在15≤y≤35重量%,优选20≤y≤30重量%范围内的氧化铝,和
(c)比例在1≤z≤30重量%,优选2≤z≤25重量%范围内的至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物,
在每种情况下基于煅烧后氧化材料总重量,其中80≤x+y+z≤100,尤其是95≤x+y+z≤100,在上述意义中的氧化材料不包括水泥。
3.根据权利要求1或2的方法,其中通过添加,粉状金属铜、铜片、粉状水泥或石墨或其混合物以基于氧化材料总重量为1-40重量%范围内的比例添加。
4.根据权利要求1-3中任一项的方法,其中石墨以基于氧化材料总重量为0.5-5重量%的比例加入氧化材料或由(ii)得到的混合物中。
5.根据权利要求1-4中任一项的方法,其中在4-9的pH下用沸水处理成形体。
6.根据权利要求1-4中任一项的方法,其中在1-20巴和100℃以上用蒸汽处理成形体。
7.根据权利要求1-6中任一项的方法,其中有机化合物为羧酸、羧酸酯、羧酸酐或内酯。
8.根据权利要求7的方法,其中有机化合物为己二酸或己二酸酯。
9.用沸水和/或蒸汽处理的成形体,该成形体包含:
氧化材料,该氧化材料包含:
(a)比例在50≤x≤80重量%,优选55≤x≤75重量%范围内的氧化铜,
(b)比例在15≤y≤35重量%,优选20≤y≤30重量%范围内的氧化铝,和
(c)比例在1≤z≤30重量%,优选2≤z≤25重量%范围内的至少一种铁、镧、钨、钼、钛、锆、锡或锰的氧化物,
在每种情况下基于煅烧后氧化材料总重量,其中80≤x+y+z≤100,尤其是95≤x+y+z≤100,
金属铜粉、铜片或水泥粉末或石墨或其混合物,基于氧化材料总重量的比例在1-40重量%范围内,
石墨,基于氧化材料总重量的比例为0.5-5重量%,
其中,氧化材料,金属铜粉或水泥粉末或其混合物和石墨的比例之和合计达到成形体的至少95重量%。
10.用沸水和/或蒸汽处理催化剂来同时提高催化剂的机械稳定性和活性及选择性的用途。
11.根据权利要求10的用途,其中催化剂包含作为活性组分的铜。
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CN106103394A (zh) * | 2014-03-12 | 2016-11-09 | 巴斯夫欧洲公司 | 甲酸盐分解的方法 |
WO2017167219A1 (zh) * | 2016-03-30 | 2017-10-05 | 长春美禾科技发展有限公司 | 一种改善乙二醇紫外透过率的方法 |
CN107848921A (zh) * | 2015-07-29 | 2018-03-27 | 巴斯夫欧洲公司 | 用于生产单乙二醇的方法 |
CN107930635A (zh) * | 2016-10-13 | 2018-04-20 | 中国石油化工股份有限公司 | 联产甲基异丁基酮和二异丁基酮的催化剂 |
CN110087767A (zh) * | 2016-12-15 | 2019-08-02 | 科莱恩国际有限公司 | 具有针对酸影响的提高的稳定性的压片的铜-锰基催化剂 |
CN115445629A (zh) * | 2022-08-23 | 2022-12-09 | 万华化学集团股份有限公司 | 一种苯乙酮加氢制α-苯乙醇的催化剂及其制备方法与应用 |
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JP5693561B2 (ja) * | 2009-04-08 | 2015-04-01 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 1,6−ヘキサンジオールをオリゴ−およびポリエステルの水素化によって製造する方法 |
TWI490034B (zh) | 2009-11-17 | 2015-07-01 | Basf Se | 製備具有增強氫化活性之經承載氫化觸媒之方法 |
JP5855106B2 (ja) | 2010-09-08 | 2016-02-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ε−カプロラクトン及び1,6−ヘキサンジオールの製造法 |
DE102012012510B4 (de) | 2012-06-22 | 2018-12-06 | Clariant International Ltd. | Graphithaltiger Katalysatorformkörper, dessen Herstellverfahren sowie Verwendung |
CN107930638B (zh) * | 2016-10-13 | 2020-02-18 | 中国石油化工股份有限公司 | 丙酮一步法合成甲基异丁基酮的铜基催化剂 |
US20220041533A1 (en) | 2018-12-03 | 2022-02-10 | Basf Se | Process for producing 1-(4-isobutylphenyl)ethanol by hydrogenation of 1-(4-isobutyl-phenyl)ethanone in the presence of a catalyst composition comprising copper |
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Family Cites Families (5)
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SU728908A1 (ru) * | 1977-01-25 | 1980-04-25 | Lender Yurij V | Способ пассивации алюмомедьцинкового катализатора синтеза метанола |
DE19942895A1 (de) * | 1999-09-08 | 2001-03-15 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
DE10313702A1 (de) * | 2003-03-27 | 2004-10-07 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
DE102004033556A1 (de) * | 2004-07-09 | 2006-02-16 | Basf Ag | Katalysatorformkörper und Verfahren zur Hydrierung von Carbonylverbindungen |
DE102004033554A1 (de) * | 2004-07-09 | 2006-02-16 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
-
2005
- 2005-07-13 DE DE200510032726 patent/DE102005032726A1/de not_active Withdrawn
-
2006
- 2006-07-06 EP EP06777609A patent/EP1904228A1/de not_active Withdrawn
- 2006-07-06 CA CA 2614520 patent/CA2614520A1/en not_active Abandoned
- 2006-07-06 WO PCT/EP2006/063958 patent/WO2007006719A1/de active Application Filing
- 2006-07-06 JP JP2008520848A patent/JP2009502746A/ja not_active Withdrawn
- 2006-07-06 CN CNA2006800253511A patent/CN101309749A/zh active Pending
- 2006-07-06 KR KR1020087003418A patent/KR20080039411A/ko not_active Application Discontinuation
- 2006-07-06 SG SG201003818-0A patent/SG162740A1/en unknown
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CN106103394A (zh) * | 2014-03-12 | 2016-11-09 | 巴斯夫欧洲公司 | 甲酸盐分解的方法 |
CN106103394B (zh) * | 2014-03-12 | 2019-08-27 | 巴斯夫欧洲公司 | 甲酸盐分解的方法 |
CN107848921A (zh) * | 2015-07-29 | 2018-03-27 | 巴斯夫欧洲公司 | 用于生产单乙二醇的方法 |
CN107848921B (zh) * | 2015-07-29 | 2022-01-25 | 巴斯夫欧洲公司 | 用于生产单乙二醇的方法 |
CN107285997A (zh) * | 2016-03-30 | 2017-10-24 | 长春美禾科技发展有限公司 | 一种改善乙二醇紫外透过率的方法 |
WO2017167219A1 (zh) * | 2016-03-30 | 2017-10-05 | 长春美禾科技发展有限公司 | 一种改善乙二醇紫外透过率的方法 |
US10836696B2 (en) | 2016-03-30 | 2020-11-17 | The Coca-Cola Company | Method for increasing UV transmittance of ethylene glycol |
CN107285997B (zh) * | 2016-03-30 | 2022-04-22 | 长春美禾科技发展有限公司 | 一种改善乙二醇紫外透过率的方法 |
CN107930635A (zh) * | 2016-10-13 | 2018-04-20 | 中国石油化工股份有限公司 | 联产甲基异丁基酮和二异丁基酮的催化剂 |
CN107930635B (zh) * | 2016-10-13 | 2020-02-18 | 中国石油化工股份有限公司 | 联产甲基异丁基酮和二异丁基酮的催化剂 |
CN110087767A (zh) * | 2016-12-15 | 2019-08-02 | 科莱恩国际有限公司 | 具有针对酸影响的提高的稳定性的压片的铜-锰基催化剂 |
CN115445629A (zh) * | 2022-08-23 | 2022-12-09 | 万华化学集团股份有限公司 | 一种苯乙酮加氢制α-苯乙醇的催化剂及其制备方法与应用 |
CN115445629B (zh) * | 2022-08-23 | 2024-02-27 | 万华化学集团股份有限公司 | 一种苯乙酮加氢制α-苯乙醇的催化剂及其制备方法与应用 |
Also Published As
Publication number | Publication date |
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KR20080039411A (ko) | 2008-05-07 |
SG162740A1 (en) | 2010-07-29 |
CA2614520A1 (en) | 2007-01-18 |
WO2007006719A1 (de) | 2007-01-18 |
DE102005032726A1 (de) | 2007-01-18 |
JP2009502746A (ja) | 2009-01-29 |
EP1904228A1 (de) | 2008-04-02 |
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