TW434209B - Process for the production of higher oxo alcohols - Google Patents
Process for the production of higher oxo alcohols Download PDFInfo
- Publication number
- TW434209B TW434209B TW086118748A TW86118748A TW434209B TW 434209 B TW434209 B TW 434209B TW 086118748 A TW086118748 A TW 086118748A TW 86118748 A TW86118748 A TW 86118748A TW 434209 B TW434209 B TW 434209B
- Authority
- TW
- Taiwan
- Prior art keywords
- cobalt
- water
- miscible
- organic
- patent application
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 73
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 239000004435 Oxo alcohol Substances 0.000 title claims abstract 4
- 239000010941 cobalt Substances 0.000 claims abstract description 89
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 89
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 81
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 67
- 150000001336 alkenes Chemical class 0.000 claims abstract description 50
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 46
- 150000001868 cobalt Chemical class 0.000 claims abstract description 37
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 36
- 239000012074 organic phase Substances 0.000 claims abstract description 32
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 150000001298 alcohols Chemical class 0.000 claims abstract description 22
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 21
- 238000000605 extraction Methods 0.000 claims abstract description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 17
- 239000008346 aqueous phase Substances 0.000 claims abstract description 13
- 239000012266 salt solution Substances 0.000 claims abstract description 12
- 239000004033 plastic Substances 0.000 claims abstract description 6
- 229920003023 plastic Polymers 0.000 claims abstract description 6
- 239000004014 plasticizer Substances 0.000 claims abstract description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims description 51
- 239000012071 phase Substances 0.000 claims description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- 230000000875 corresponding effect Effects 0.000 claims description 19
- 238000011049 filling Methods 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 230000002079 cooperative effect Effects 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 5
- 241000255789 Bombyx mori Species 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- -1 hydrocarbon acid gas Chemical class 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 235000015170 shellfish Nutrition 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 3
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 2
- 206010017062 Formication Diseases 0.000 claims 2
- 238000005336 cracking Methods 0.000 claims 2
- 208000035824 paresthesia Diseases 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 229910052778 Plutonium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002716 delivery method Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 claims 1
- 239000000779 smoke Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- 230000006315 carbonylation Effects 0.000 description 8
- 238000005810 carbonylation reaction Methods 0.000 description 8
- 229940011182 cobalt acetate Drugs 0.000 description 7
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- OUFCBJZGDJFSIK-UHFFFAOYSA-N 11-methyldodecanal Chemical compound CC(C)CCCCCCCCCC=O OUFCBJZGDJFSIK-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000004439 Isononyl alcohol Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001869 cobalt compounds Chemical class 0.000 description 2
- ZEWGRSAJWPFTRK-UHFFFAOYSA-N cobalt rhenium Chemical compound [Co].[Re] ZEWGRSAJWPFTRK-UHFFFAOYSA-N 0.000 description 2
- UMYVESYOFCWRIW-UHFFFAOYSA-N cobalt;methanone Chemical compound O=C=[Co] UMYVESYOFCWRIW-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000008031 plastic plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- YHHQTENWSYRAKA-UHFFFAOYSA-N 7-methyloctyl formate Chemical compound CC(C)CCCCCCOC=O YHHQTENWSYRAKA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000252073 Anguilliformes Species 0.000 description 1
- 101100124609 Caenorhabditis elegans zyg-12 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- OOSOWXQJLLTIAF-UHFFFAOYSA-N Perisoxal citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=C(C=2C=CC=CC=2)ON=C1C(O)CN1CCCCC1.C1=C(C=2C=CC=CC=2)ON=C1C(O)CN1CCCCC1 OOSOWXQJLLTIAF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 150000001218 Thorium Chemical class 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 240000008708 Vanda coerulea Species 0.000 description 1
- CGVQUIHNXBDLPN-UHFFFAOYSA-N [Co].O=C=[Co] Chemical compound [Co].O=C=[Co] CGVQUIHNXBDLPN-UHFFFAOYSA-N 0.000 description 1
- LVAMVZXECCXUGI-UHFFFAOYSA-N acetic acid;thallium Chemical compound [Tl].CC(O)=O LVAMVZXECCXUGI-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IYRDVAUFQZOLSB-UHFFFAOYSA-N copper iron Chemical compound [Fe].[Cu] IYRDVAUFQZOLSB-UHFFFAOYSA-N 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- LWLLFNYPJBPFOL-UHFFFAOYSA-N formic acid 2-methylbuta-1,3-diene Chemical compound C=CC(C)=C.C(=O)O LWLLFNYPJBPFOL-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 229950005491 perisoxal Drugs 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
- RQFVHGAXCJVPBZ-UHFFFAOYSA-N propylene pentamer Chemical group CC=C.CC=C.CC=C.CC=C.CC=C RQFVHGAXCJVPBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003282 rhenium compounds Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19654340A DE19654340A1 (de) | 1996-12-24 | 1996-12-24 | Verfahren zur Herstellung von höheren Oxo-Alkoholen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW434209B true TW434209B (en) | 2001-05-16 |
Family
ID=7816198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW086118748A TW434209B (en) | 1996-12-24 | 1997-12-12 | Process for the production of higher oxo alcohols |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6015928A (en, 2012) |
| EP (1) | EP0850905B1 (en, 2012) |
| JP (1) | JP3877852B2 (en, 2012) |
| KR (1) | KR100506965B1 (en, 2012) |
| CN (1) | CN1082501C (en, 2012) |
| AR (1) | AR008722A1 (en, 2012) |
| AT (1) | ATE203230T1 (en, 2012) |
| BR (1) | BR9706447A (en, 2012) |
| CA (1) | CA2225773C (en, 2012) |
| CZ (1) | CZ290974B6 (en, 2012) |
| DE (2) | DE19654340A1 (en, 2012) |
| ES (1) | ES2160293T3 (en, 2012) |
| ID (1) | ID19255A (en, 2012) |
| IN (1) | IN1997CH01832A (en, 2012) |
| MX (1) | MX203748B (en, 2012) |
| MY (1) | MY117877A (en, 2012) |
| PL (1) | PL194180B1 (en, 2012) |
| RO (1) | RO120483B1 (en, 2012) |
| RU (1) | RU2183210C2 (en, 2012) |
| SA (1) | SA97180684B1 (en, 2012) |
| SG (1) | SG63790A1 (en, 2012) |
| TW (1) | TW434209B (en, 2012) |
| ZA (1) | ZA9711554B (en, 2012) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19842368A1 (de) * | 1998-09-16 | 2000-03-23 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von höheren Oxoalkoholen aus Olefingemischen durch zweistufige Hydroformylierung |
| DE19842369A1 (de) | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur Hydrierung von Hydroformylierungsgemischen |
| DE19842371A1 (de) | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur Herstellung von höheren Oxo-Alkoholen aus Olefingemischen |
| DE19842370A1 (de) | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur selektiven Hydrierung von Hydroformylierungsgemischen |
| DE19933348B4 (de) | 1999-07-16 | 2005-11-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Reduzierung oxidischer Hydrierkontakte |
| DE19939491A1 (de) * | 1999-08-20 | 2001-02-22 | Basf Ag | Kontinuierliches Verfahren zur Hydroformylierung von Olefinen mit 6 bis 20 Kohlenstoffatomen |
| PL358016A1 (en) | 2000-03-30 | 2004-08-09 | Shell Internationale Research Maatschappij B.V. | Dmc complex catalyst and process for its preparation |
| DE10034360A1 (de) * | 2000-07-14 | 2002-01-24 | Oxeno Olefinchemie Gmbh | Mehrstufiges Verfahren zur Herstellung von Oxo-Aldehyden und/oder Alkoholen |
| DE10058383A1 (de) * | 2000-11-24 | 2002-05-29 | Oxeno Olefinchemie Gmbh | Neue Phosphininverbindungen und deren Metallkomplexe |
| US20020115382A1 (en) * | 2001-02-16 | 2002-08-22 | Luthy G. Steve | Method and apparatus to produce a precisely textured surface on a workpiece |
| DE10135906A1 (de) * | 2001-07-24 | 2003-02-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydroformylierung von höheren Olefinen mit Kobaltverbindungen als Katalysator |
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| CN114426469B (zh) * | 2020-09-28 | 2024-07-09 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化制备醇和醛的方法 |
| CN114656343B (zh) * | 2020-12-23 | 2024-05-17 | 中国石油化工股份有限公司 | 一种制备醛和醇的方法 |
| CN115701418B (zh) * | 2021-08-02 | 2024-05-17 | 中国石油化工股份有限公司 | 醛醇组合物及其制备方法、一种连续制备醛、醇的方法 |
| CN116063168B (zh) * | 2021-10-29 | 2024-12-06 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应的方法 |
| CN116063155B (zh) * | 2021-10-29 | 2024-12-06 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应制备醇的方法 |
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| DE2206252C3 (de) * | 1972-02-10 | 1981-07-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von vorwiegend geradkettigen Aldehyden |
| BE787274A (fr) * | 1971-08-07 | 1973-02-07 | Basf Ag | Procede de preparation d'aldehydes a structure preponderante lineaire |
| DE2139630C3 (de) * | 1971-08-07 | 1979-03-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von vorwiegend geradkettigen Aldehyden |
| DE2244373A1 (de) * | 1972-09-09 | 1974-04-04 | Basf Ag | Verfahren zur kontinuierlichen herstellung von waessrigen loesungen von kobaltcarbonylen |
| JPS5314190A (en) * | 1976-07-26 | 1978-02-08 | Agency Of Ind Science & Technol | Complex catalyst for hydroformylation |
| US4329521A (en) * | 1980-04-09 | 1982-05-11 | Uop Inc. | Oxo alcohol synthesis with rhodium catalyst recycle |
| DE3935796A1 (de) * | 1989-10-27 | 1991-05-02 | Basf Ag | Di-decylphthalat-gemisch und seine verwendung als weichmacher |
| US5237105A (en) * | 1992-05-29 | 1993-08-17 | Exxon Chemical Patents Inc. | Method for removing hydroformylation catalyst |
| DE4333324A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Ag | Decylalkoholgemische, daraus erhältliche Phthalsäureester und ihre Verwendung als Weichmacher |
| US5406006A (en) * | 1994-05-24 | 1995-04-11 | Exxon Chemical Patents Inc | Method for preparing a preformer catalyst via in-situ activation |
| US5600031A (en) * | 1995-08-18 | 1997-02-04 | Exxon Chemical Patents, Inc. | Process for preforming cobaltous salts using shell-type preformer catalysts |
-
1996
- 1996-12-24 DE DE19654340A patent/DE19654340A1/de not_active Withdrawn
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1997
- 1997-08-19 IN IN1832CH1997 patent/IN1997CH01832A/en unknown
- 1997-09-30 ID IDP973331A patent/ID19255A/id unknown
- 1997-10-29 EP EP97118801A patent/EP0850905B1/de not_active Expired - Lifetime
- 1997-10-29 AT AT97118801T patent/ATE203230T1/de active
- 1997-10-29 ES ES97118801T patent/ES2160293T3/es not_active Expired - Lifetime
- 1997-10-29 DE DE59704070T patent/DE59704070D1/de not_active Expired - Lifetime
- 1997-12-06 SA SA97180684A patent/SA97180684B1/ar unknown
- 1997-12-09 MX MX9709932A patent/MX203748B/es unknown
- 1997-12-12 CZ CZ19974011A patent/CZ290974B6/cs not_active IP Right Cessation
- 1997-12-12 TW TW086118748A patent/TW434209B/zh active
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- 1997-12-19 CN CN97126061A patent/CN1082501C/zh not_active Expired - Lifetime
- 1997-12-19 SG SG1997004579A patent/SG63790A1/en unknown
- 1997-12-19 AR ARP970106020A patent/AR008722A1/es active IP Right Grant
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- 1997-12-22 BR BR9706447A patent/BR9706447A/pt not_active IP Right Cessation
- 1997-12-23 RU RU97122178/04A patent/RU2183210C2/ru active
- 1997-12-23 ZA ZA9711554A patent/ZA9711554B/xx unknown
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- 1997-12-24 JP JP35507597A patent/JP3877852B2/ja not_active Expired - Lifetime
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|---|---|
| CA2225773C (en) | 2005-10-25 |
| AR008722A1 (es) | 2000-02-09 |
| RO120483B1 (ro) | 2006-02-28 |
| CZ401197A3 (cs) | 1998-07-15 |
| CA2225773A1 (en) | 1998-06-24 |
| MX9709932A (es) | 1998-06-30 |
| ZA9711554B (en) | 1998-06-24 |
| PL194180B1 (pl) | 2007-05-31 |
| PL323777A1 (en) | 1998-07-06 |
| SG63790A1 (en) | 1999-03-30 |
| MY117877A (en) | 2004-08-30 |
| CN1082501C (zh) | 2002-04-10 |
| ES2160293T3 (es) | 2001-11-01 |
| MX203748B (es) | 2001-08-14 |
| CZ290974B6 (cs) | 2002-11-13 |
| KR100506965B1 (ko) | 2005-11-21 |
| ID19255A (id) | 1998-06-28 |
| ATE203230T1 (de) | 2001-08-15 |
| CN1186060A (zh) | 1998-07-01 |
| SA97180684B1 (ar) | 2006-04-22 |
| DE59704070D1 (de) | 2001-08-23 |
| IN1997CH01832A (en, 2012) | 2006-09-22 |
| EP0850905B1 (de) | 2001-07-18 |
| JPH10204009A (ja) | 1998-08-04 |
| KR19980064557A (ko) | 1998-10-07 |
| RU2183210C2 (ru) | 2002-06-10 |
| JP3877852B2 (ja) | 2007-02-07 |
| EP0850905A1 (de) | 1998-07-01 |
| US6015928A (en) | 2000-01-18 |
| DE19654340A1 (de) | 1998-08-06 |
| BR9706447A (pt) | 1999-06-01 |
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