DE2213485C2 - Verfahren zur Herstellung von Katalysatoren, die ein Metall sowie gegebenenfalls ein poröses, hitzebeständiges Trägermaterial enthalten - Google Patents
Verfahren zur Herstellung von Katalysatoren, die ein Metall sowie gegebenenfalls ein poröses, hitzebeständiges Trägermaterial enthaltenInfo
- Publication number
- DE2213485C2 DE2213485C2 DE2213485A DE2213485A DE2213485C2 DE 2213485 C2 DE2213485 C2 DE 2213485C2 DE 2213485 A DE2213485 A DE 2213485A DE 2213485 A DE2213485 A DE 2213485A DE 2213485 C2 DE2213485 C2 DE 2213485C2
- Authority
- DE
- Germany
- Prior art keywords
- percent
- weight
- acid
- metal
- solution
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 title claims description 65
- 229910052751 metal Inorganic materials 0.000 title claims description 46
- 239000002184 metal Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000000463 material Substances 0.000 title description 32
- 239000012876 carrier material Substances 0.000 claims description 27
- 229910052782 aluminium Inorganic materials 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 21
- 239000002244 precipitate Substances 0.000 claims description 20
- 229910052802 copper Inorganic materials 0.000 claims description 18
- 238000006114 decarboxylation reaction Methods 0.000 claims description 15
- 150000002739 metals Chemical class 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- 229910052709 silver Inorganic materials 0.000 claims description 13
- 229910052759 nickel Inorganic materials 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 229910052725 zinc Inorganic materials 0.000 claims description 12
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 11
- 239000004332 silver Substances 0.000 claims description 11
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- -1 alkene monocarboxylic acid Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052718 tin Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 34
- 239000002253 acid Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 28
- 229920002125 Sokalan® Polymers 0.000 description 26
- 239000004584 polyacrylic acid Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000002245 particle Substances 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 22
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 22
- 229910021645 metal ion Inorganic materials 0.000 description 21
- 239000010949 copper Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000011148 porous material Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 239000011701 zinc Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 7
- 239000010941 cobalt Substances 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052770 Uranium Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- WWMQIJFJSHVMDM-UHFFFAOYSA-N 2-ethenoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC=C WWMQIJFJSHVMDM-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SMNMOEIFYRALNM-UHFFFAOYSA-L copper;hexanoate Chemical compound [Cu+2].CCCCCC([O-])=O.CCCCCC([O-])=O SMNMOEIFYRALNM-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- YHTHFLDEUGBGKY-UHFFFAOYSA-N 2-but-1-enylpropanedioic acid Chemical compound CCC=CC(C(O)=O)C(O)=O YHTHFLDEUGBGKY-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000531 Co alloy Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- JZVJCTVXALSTOA-UHFFFAOYSA-N Rubia akane RA-I Natural products C1=CC(OC)=CC=C1CC(N(C)C(=O)C(CO)NC(=O)C(C)NC(=O)C(N(C1=O)C)C2)C(=O)NC(C)C(=O)N(C)C1CC(C=C1)=CC=C1OC1=CC2=CC=C1O JZVJCTVXALSTOA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- JCXUQCCADMZQRP-UHFFFAOYSA-N aluminum;nickel(2+);propan-2-olate Chemical compound [Al+3].[Ni+2].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] JCXUQCCADMZQRP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- JZVJCTVXALSTOA-XMPIZRASSA-N chembl1288988 Chemical compound C1=CC(OC)=CC=C1C[C@H](N(C)C(=O)[C@H](CO)NC(=O)[C@@H](C)NC(=O)[C@@H](N(C1=O)C)C2)C(=O)N[C@@H](C)C(=O)N(C)[C@H]1CC(C=C1)=CC=C1OC1=CC2=CC=C1O JZVJCTVXALSTOA-XMPIZRASSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- MKZIDVHSSGEADY-UHFFFAOYSA-L hexanoate;nickel(2+) Chemical compound [Ni+2].CCCCCC([O-])=O.CCCCCC([O-])=O MKZIDVHSSGEADY-UHFFFAOYSA-L 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/024—Multiple impregnation or coating
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
- C01B13/14—Methods for preparing oxides or hydroxides in general
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/10—Solid density
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/14—Pore volume
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/31—Ionic cross-link
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/33—Molecular sieve
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S264/00—Plastic and nonmetallic article shaping or treating: processes
- Y10S264/19—Inorganic fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12698271A | 1971-03-22 | 1971-03-22 | |
| US12673671A | 1971-03-22 | 1971-03-22 | |
| US12698371A | 1971-03-22 | 1971-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2213485A1 DE2213485A1 (de) | 1972-09-28 |
| DE2213485C2 true DE2213485C2 (de) | 1986-08-14 |
Family
ID=27383471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2213485A Expired DE2213485C2 (de) | 1971-03-22 | 1972-03-20 | Verfahren zur Herstellung von Katalysatoren, die ein Metall sowie gegebenenfalls ein poröses, hitzebeständiges Trägermaterial enthalten |
Country Status (11)
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018594A (en) * | 1971-08-12 | 1977-04-19 | Hydrophilics International, Inc. | Sustained release polymers |
| GB1394990A (en) * | 1971-08-12 | 1975-05-21 | Hydrophilics Int Inc | Copolymers and compositions containing copolymers |
| ZA732070B (en) * | 1972-03-28 | 1973-12-19 | Hardman & Holden Ltd | Aluminium containing compounds |
| US4166891A (en) * | 1972-04-19 | 1979-09-04 | Elliott Stanley B | Visual-type hygrometer |
| US3816308A (en) * | 1972-05-05 | 1974-06-11 | Monsanto Co | Beneficiating agents |
| US3908002A (en) * | 1972-05-30 | 1975-09-23 | Shell Oil Co | Production of alpha alumina |
| US3892679A (en) * | 1973-09-24 | 1975-07-01 | Shell Oil Co | Catalyst for preparation of ethylene oxide |
| US4116710A (en) * | 1973-10-24 | 1978-09-26 | The Dow Chemical Company | Metallic particulate |
| US3997486A (en) * | 1973-12-04 | 1976-12-14 | E. I. Du Pont De Nemours And Company | Preparation of polymeric chromium complexes |
| JPS526953B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-12-12 | 1977-02-25 | ||
| LU69408A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-02-18 | 1975-12-09 | ||
| LU69407A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-02-18 | 1975-12-09 | ||
| US4065442A (en) * | 1974-10-31 | 1977-12-27 | Standard Oil Company | Pyrolysis compositions from silver salts of polycarboxylic acids |
| US4174447A (en) * | 1975-02-26 | 1979-11-13 | Standard Oil Company (Indiana) | Process for dimerization, arylation and trifluoromethylation of aromatic and heterocyclic compounds |
| US4090013A (en) * | 1975-03-07 | 1978-05-16 | National Starch And Chemical Corp. | Absorbent composition of matter |
| US4043952A (en) * | 1975-05-09 | 1977-08-23 | National Starch And Chemical Corporation | Surface treatment process for improving dispersibility of an absorbent composition, and product thereof |
| US4093571A (en) * | 1976-01-14 | 1978-06-06 | Celanese Corporation | Process for making porous metal containing powder coating compositions |
| US4197220A (en) * | 1976-08-27 | 1980-04-08 | California Institute Of Technology | Impregnated metal-polymeric functional beads |
| US4123396A (en) * | 1976-08-27 | 1978-10-31 | California Institute Of Technology | Impregnated metal-polymeric functional beads |
| US4291136A (en) * | 1978-03-31 | 1981-09-22 | Union Carbide Corporation | Water-curable silane modified alkylene alkylacrylate copolymer and a process for its production |
| US4169099A (en) * | 1978-05-25 | 1979-09-25 | Halcon Research And Development Corporation | Catalyst and process for producing ethylene oxide |
| US4434272A (en) | 1980-09-30 | 1984-02-28 | Union Carbide Corporation | Water-curable, silane modified alkyl acrylate copolymers and a process for the preparation thereof |
| US4331619A (en) * | 1980-12-08 | 1982-05-25 | Allied Corporation | Ethylene-chlorotrifluoroethylene copolymer foam |
| US4394460A (en) * | 1980-12-08 | 1983-07-19 | Allied Corporation | Ethylene-chlorotrifluoroethylene copolymer foam |
| US4381376A (en) * | 1980-12-29 | 1983-04-26 | Allied Corporation | Preparation of low molecular weight copolymer salts |
| US4410753A (en) * | 1981-03-20 | 1983-10-18 | Publicker Industries, Inc. | Process and catalyst for skeletal isomerization of olefins |
| GB8320904D0 (en) * | 1983-08-03 | 1983-09-07 | Rubber & Plastic Res Ass | Transformations within polymers |
| US4533508A (en) * | 1983-08-22 | 1985-08-06 | The Dow Chemical Company | Metal oxide fibers from acrylate salts |
| FR2554303B1 (fr) * | 1983-10-28 | 1986-04-18 | Rhone Poulenc Rech | Substrats metallisables pour circuits imprimes et leur procede de preparation |
| FR2556238B1 (fr) * | 1983-12-12 | 1987-10-23 | Commissariat Energie Atomique | Materiau comportant des microagregats de composes inorganiques ou organometalliques, utilisable en particulier en catalyse heterogene et son procede de fabrication |
| US4627966A (en) * | 1984-03-19 | 1986-12-09 | General Motors Corporation | Formation of fine particle sinterable ceramic powders |
| FI70682C (fi) * | 1984-06-20 | 1987-08-05 | Kemira Oy | Traeskyddsmedel och dess anvaendning som ytbehandlingsmedel. |
| US4675111A (en) * | 1984-07-16 | 1987-06-23 | Micro-Plate Inc. | Solution waste treatment module |
| US4714691A (en) * | 1985-06-25 | 1987-12-22 | Ethyl Corporation | Heterogeneous catalyst process |
| US4732721A (en) * | 1985-09-30 | 1988-03-22 | Agency Of Industrial Science And Technology | Method for production of shaped bodies of metal salts of polyacrylic acid |
| GB8529198D0 (en) * | 1985-11-27 | 1986-01-02 | Allied Colloids Ltd | Surface treatment of polymers |
| US4771105A (en) * | 1986-02-05 | 1988-09-13 | Sekisui Kaseihin Kogyo Kabushiki Kaisha | Water-absorbent resin and process for producing the same |
| JPH0688884B2 (ja) * | 1986-07-14 | 1994-11-09 | 日本ペイント株式会社 | 金属化合物担持防汚塗料用粒子の製造法 |
| FR2628665A1 (fr) * | 1988-03-16 | 1989-09-22 | Rhone Poulenc Chimie | Compositions de matieres susceptibles d'etre utilisees pour la preparation de poudres minerales ultrafines de type oxyde, et un de leur procede de preparation |
| US5053362A (en) * | 1988-09-27 | 1991-10-01 | The Carborundum Company | Ceramic fiber refractory moldable compositions |
| US5302773A (en) * | 1989-07-20 | 1994-04-12 | The Dow Chemical Company | Process of oxidizing aliphatic hydrocarbons employing a molybdate catalyst encapsulated in a hard, glassy silica matrix |
| AU656537B2 (en) | 1990-10-12 | 1995-02-09 | Union Carbide Chemicals & Plastics Technology Corporation | Alkylene oxide catalysts having enhanced activity and/or stability |
| US5534237A (en) * | 1991-07-23 | 1996-07-09 | Kubushiki Kaisha Riken | Method of cleaning an exhaust gas and exhaust gas cleaner therefor |
| US5240493A (en) * | 1992-01-16 | 1993-08-31 | Institute Of Gas Technology | Process for preparing submicron/nanosize ceramic powders from precursors incorporated within a polymeric foam |
| US5338334A (en) * | 1992-01-16 | 1994-08-16 | Institute Of Gas Technology | Process for preparing submicron/nanosize ceramic powders from precursors incorporated within a polymeric foam |
| ZA933185B (en) | 1992-05-08 | 1994-05-23 | Dick Co Ab | Encapsulated magnetic particles pigments and carbon black compositions and methods related thereto |
| EP0686132A4 (en) * | 1993-02-24 | 1996-03-13 | Dudley John Mills | TREATMENT OF SWIMMING POOL WATER |
| JPH07217237A (ja) * | 1994-02-08 | 1995-08-15 | Kotobuki:Kk | 遊戯用砂場装置 |
| WO1995025129A1 (en) * | 1994-03-17 | 1995-09-21 | Exxon Chemical Patents Inc. | Spray dried polymer for catalyst support |
| DE19504319C2 (de) | 1995-02-10 | 1998-01-15 | Starck H C Gmbh Co Kg | Feinverteiltes metallisches Kobalt enthaltendes Kobalt(II)-Oxid, Verfahren zu seiner Herstellung sowie dessen Verwendung |
| DE19504320C1 (de) * | 1995-02-10 | 1996-07-25 | Starck H C Gmbh Co Kg | Verfahren zur Herstellung von Kobaltmetall-haltigem Kobalt(II)-Oxid sowie dessen Verwendung |
| JP3648247B2 (ja) * | 1995-02-21 | 2005-05-18 | エルンスト・ミュールバウアー・コマンディットゲゼルシャフト | ワックス添加シリコーンを基材とする印象材 |
| US5641920A (en) * | 1995-09-07 | 1997-06-24 | Thermat Precision Technology, Inc. | Powder and binder systems for use in powder molding |
| CA2290010C (en) * | 1998-03-09 | 2005-07-12 | Japan Science And Technology Corporation | Porous organic metal composite |
| US6338800B1 (en) | 2000-02-22 | 2002-01-15 | Natural Chemistry, Inc. | Methods and compositions using lanthanum for removing phosphates from water |
| DE10116223A1 (de) * | 2001-03-30 | 2002-10-10 | 3M Espe Ag | Automatisch mischbare Abformassen mit Putty-Konsistenz |
| KR20050008675A (ko) * | 2002-04-08 | 2005-01-21 | 즈도케미 쇼쿠바이 가부시키가이샤 | 금속수소화물 함유 배기가스 처리제 및 금속수소화물 함유배기가스 처리방법 |
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| EP1512724B1 (en) | 2003-09-04 | 2007-04-11 | 3M Espe AG | Allylsilane containing composition |
| EP1591097B1 (en) * | 2004-04-30 | 2012-06-20 | 3M Deutschland GmbH | Cationically curing two component materials containing a noble metal catalyst |
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| CA2573501A1 (en) * | 2004-07-14 | 2006-01-19 | 3M Espe Ag | Dental composition containing si-h functional carbosilane components |
| WO2006019801A1 (en) * | 2004-07-14 | 2006-02-23 | 3M Innovative Properties Company | Dental compositions containing carbosilane monomers |
| WO2006005363A1 (en) * | 2004-07-14 | 2006-01-19 | 3M Espe Ag | Dental composition containing unsaturated carbosilane containing components |
| DE602004029511D1 (de) * | 2004-07-14 | 2010-11-18 | 3M Espe Ag | Dentalzusammensetzung mit epoxy-funktionalen polymerisierbaren verbindungen |
| ATE424179T1 (de) * | 2004-07-14 | 2009-03-15 | 3M Espe Ag | Dentalzusammensetzung mit ungesättigten halogenierten arylalkylether-bestandteilen |
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| EP1652889A1 (en) * | 2004-10-12 | 2006-05-03 | 3M Espe AG | Composition containing unsaturated silicone compounds, dental materials containing them and use thereof |
| EP1650263B1 (en) | 2004-10-12 | 2013-10-23 | 3M Deutschland GmbH | Composition containing unsaturated silicone compounds, dental materials containing them and use thereof |
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| CA2610996A1 (en) | 2005-06-22 | 2007-01-04 | 3M Innovative Properties Company | Hydrophilized curable silicone impression materials with improved storage behavior |
| DE102007015842A1 (de) | 2007-03-30 | 2008-10-02 | Heraeus Kulzer Gmbh | Maschinenanmischbares A-Siliconputty und dessen Verwendung |
| US8316541B2 (en) | 2007-06-29 | 2012-11-27 | Pratt & Whitney Canada Corp. | Combustor heat shield with integrated louver and method of manufacturing the same |
| US7543383B2 (en) | 2007-07-24 | 2009-06-09 | Pratt & Whitney Canada Corp. | Method for manufacturing of fuel nozzle floating collar |
| EP2044923A1 (en) | 2007-10-04 | 2009-04-08 | 3M Innovative Properties Company | Dental composition containing glass beads, process for production and use thereof |
| US8349764B2 (en) | 2007-10-31 | 2013-01-08 | Molycorp Minerals, Llc | Composition for treating a fluid |
| DE102007054888A1 (de) | 2007-11-15 | 2009-05-20 | Dreve Prodimed Gmbh | Aus zwei Komponenten bestehendes Silikonmaterial |
| ATE525057T1 (de) | 2007-12-18 | 2011-10-15 | 3M Innovative Properties Co | Dentalzusammensetzung mit einem tensid und eine f-haltige verbindung, herstellungs- und verwendungsverfahren dafür |
| CA2737072C (en) * | 2008-09-12 | 2016-02-23 | Umicore | Cobalt bearing polymeric compositions |
| DE202008012785U1 (de) | 2008-09-25 | 2008-12-11 | Heraeus Kulzer Gmbh | Maschinenanmischbares A-Siliconputty und dessen Verwendung |
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| US9233863B2 (en) | 2011-04-13 | 2016-01-12 | Molycorp Minerals, Llc | Rare earth removal of hydrated and hydroxyl species |
| CN103649226B (zh) | 2011-06-08 | 2016-03-16 | 3M创新有限公司 | 包含硅氧烷化合物的组合物、其制备和使用方法 |
| US9283153B2 (en) | 2011-08-12 | 2016-03-15 | 3M Innovative Properties Company | Curable composition with shortened setting time, process of production and use thereof |
| DE102011115061A1 (de) | 2011-10-07 | 2013-04-11 | Dreve Prodimed Gmbh | Elastomeres Material |
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| KR20150006730A (ko) * | 2013-07-09 | 2015-01-19 | 삼성에스디아이 주식회사 | 리튬 이차 전지용 바인더 조성물, 및 이를 포함하는 음극 및 리튬 이차 전지 |
| BR112016012791B1 (pt) * | 2013-12-16 | 2021-06-08 | Dow Global Technologies Llc | catalisador heterogêneo para desidrogenação de alcanos e catalisador |
| KR20160132076A (ko) | 2014-03-07 | 2016-11-16 | 몰리코프 미네랄스, 엘엘씨 | 비소 제거 특성이 뛰어난 세륨(iv) 산화물 |
| CN104353549B (zh) * | 2014-11-18 | 2017-01-18 | 崔雷 | 一种电磁除铁机 |
| WO2016099910A1 (en) | 2014-12-16 | 2016-06-23 | 3M Innovative Properties Company | Hardenable dental impression composition comprising a polymeric filler particles and use thereof |
| EP3302402B1 (en) | 2015-05-29 | 2020-04-29 | 3M Innovative Properties Company | Kit of parts for conducting a dental impression and retraction process |
| WO2018136351A1 (en) | 2017-01-18 | 2018-07-26 | 3M Innovative Properties Company | Curable composition for dental retraction |
| US10543480B2 (en) * | 2018-04-16 | 2020-01-28 | Chevron Phillips Chemical Company Lp | Methods of preparing a catalyst utilizing hydrated reagents |
| US10722874B2 (en) | 2018-04-16 | 2020-07-28 | Chevron Phillips Chemical Company Lp | Methods of preparing a catalyst utilizing hydrated reagents |
| US20210284962A1 (en) | 2018-06-21 | 2021-09-16 | The Regents Of The University Of California | Generation of a population of hindbrain cells and hindbrain-like organoids from pluripotent stem cells |
| US11772082B1 (en) | 2018-06-21 | 2023-10-03 | Avn Corporation | Catalyst supports—composition and process of manufacture |
| DE102019109729A1 (de) | 2019-04-12 | 2020-10-15 | Dreve Prodimed Gmbh | Silikone und Silikon-Lacke zur Oberflächenflächenbehandlung von polymerisierbaren Materialien in der Medizintechnik, insbesondere im Hörgeräteakustik-Bereich |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3180844A (en) * | 1960-11-09 | 1965-04-27 | Dow Chemical Co | Salts of monocarboxylic acid copolymers as thickeners for non-polar solvents |
-
1971
- 1971-03-22 US US00126982A patent/US3775352A/en not_active Expired - Lifetime
- 1971-03-22 US US00126736A patent/US3779952A/en not_active Expired - Lifetime
- 1971-03-22 US US00126983A patent/US3758418A/en not_active Expired - Lifetime
-
1972
- 1972-02-23 CA CA135,390A patent/CA971692A/en not_active Expired
- 1972-02-23 CA CA135,389A patent/CA958150A/en not_active Expired
- 1972-03-15 BE BE780674A patent/BE780674A/xx not_active IP Right Cessation
- 1972-03-20 IT IT22120/72A patent/IT950392B/it active
- 1972-03-20 NL NLAANVRAGE7203665,A patent/NL169886C/xx not_active IP Right Cessation
- 1972-03-20 FR FR7209670A patent/FR2130465B1/fr not_active Expired
- 1972-03-20 GB GB1290872A patent/GB1393005A/en not_active Expired
- 1972-03-20 CH CH411672A patent/CH582544A5/xx not_active IP Right Cessation
- 1972-03-20 SE SE7203580A patent/SE392574B/xx unknown
- 1972-03-20 DE DE2213485A patent/DE2213485C2/de not_active Expired
- 1972-03-21 CA CA137,679A patent/CA967934A/en not_active Expired
- 1972-03-21 JP JP2754972A patent/JPS5720015B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3779952A (en) | 1973-12-18 |
| SE392574B (sv) | 1977-04-04 |
| CA967934A (en) | 1975-05-20 |
| FR2130465A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-11-03 |
| GB1393005A (en) | 1975-05-07 |
| DE2213485A1 (de) | 1972-09-28 |
| NL7203665A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-26 |
| NL169886C (nl) | 1982-09-01 |
| CA958150A (en) | 1974-11-19 |
| JPS5720015B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-04-26 |
| US3775352A (en) | 1973-11-27 |
| NL169886B (nl) | 1982-04-01 |
| CA971692A (en) | 1975-07-22 |
| IT950392B (it) | 1973-06-20 |
| FR2130465B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-29 |
| US3758418A (en) | 1973-09-11 |
| CH582544A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-12-15 |
| BE780674A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-15 |
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