DD298085A5 - Verfahren zur herstellung von aldehyden - Google Patents

Verfahren zur herstellung von aldehyden Download PDF

Info

Publication number: DD298085A5
Authority: DD; German Democratic Republic
Prior art keywords: branched; straight; alkyl; chain; hydrogen
Prior art date: 1989-08-23

Application number

DD90343536A

Other languages

German (de)

English (en)

Inventor

Winfried Joentgen

Helmut Fiege

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1989-08-23

Filing date

1990-08-20

Publication date

1992-02-06

1990-08-20 Application filed by ��@��k�� filed Critical ��@��k��

1992-02-06 Publication of DD298085A5 publication Critical patent/DD298085A5/de

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 10
150000001299 aldehydes Chemical class 0.000 title description 13
-1 aliphatic aldehydes Chemical class 0.000 claims abstract description 45
239000003054 catalyst Substances 0.000 claims abstract description 34
229910052751 metal Inorganic materials 0.000 claims abstract description 29
239000002184 metal Substances 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
239000011651 chromium Substances 0.000 claims abstract description 16
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 15
229910052804 chromium Inorganic materials 0.000 claims abstract description 11
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
159000000032 aromatic acids Chemical class 0.000 claims abstract description 10
239000011701 zinc Substances 0.000 claims abstract description 10
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 9
239000010949 copper Substances 0.000 claims abstract description 9
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
229910052720 vanadium Inorganic materials 0.000 claims abstract description 9
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052725 zinc Inorganic materials 0.000 claims abstract description 9
229910052793 cadmium Inorganic materials 0.000 claims abstract description 8
229910052802 copper Inorganic materials 0.000 claims abstract description 8
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
150000008064 anhydrides Chemical class 0.000 claims abstract description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 6
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 6
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 6
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims abstract description 6
150000002739 metals Chemical class 0.000 claims abstract description 6
239000011733 molybdenum Substances 0.000 claims abstract description 6
239000010936 titanium Substances 0.000 claims abstract description 6
229910052719 titanium Inorganic materials 0.000 claims abstract description 6
229910052759 nickel Inorganic materials 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 4
230000003197 catalytic effect Effects 0.000 claims abstract description 4
229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
239000010941 cobalt Substances 0.000 claims abstract description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
239000007789 gas Substances 0.000 claims abstract description 4
150000004820 halides Chemical class 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
150000004679 hydroxides Chemical class 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
238000001354 calcination Methods 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 4
238000001035 drying Methods 0.000 claims description 4
229940095102 methyl benzoate Drugs 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims description 2
ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
UFRKOOMLVWDICO-UHFFFAOYSA-N n-ethyl-n-fluoroethanamine Chemical class CCN(F)CC UFRKOOMLVWDICO-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical class 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
238000005406 washing Methods 0.000 claims 2
BFZWJHVEJPNAJI-UHFFFAOYSA-N NC(N(C)NCC)NC Chemical class NC(N(C)NCC)NC BFZWJHVEJPNAJI-UHFFFAOYSA-N 0.000 claims 1
239000003426 co-catalyst Substances 0.000 abstract 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 18
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
239000004408 titanium dioxide Substances 0.000 description 9
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
239000011572 manganese Substances 0.000 description 4
UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 4
229940041260 vanadyl sulfate Drugs 0.000 description 4
229910000352 vanadyl sulfate Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
229910010413 TiO 2 Inorganic materials 0.000 description 3
XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910001935 vanadium oxide Inorganic materials 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021542 Vanadium(IV) oxide Inorganic materials 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000000975 co-precipitation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(iv) oxide Chemical compound O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
OGUCKKLSDGRKSH-UHFFFAOYSA-N oxalic acid oxovanadium Chemical compound [V].[O].C(C(=O)O)(=O)O OGUCKKLSDGRKSH-UHFFFAOYSA-N 0.000 description 2
DUSYNUCUMASASA-UHFFFAOYSA-N oxygen(2-);vanadium(4+) Chemical compound [O-2].[O-2].[V+4] DUSYNUCUMASASA-UHFFFAOYSA-N 0.000 description 2
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003682 vanadium compounds Chemical class 0.000 description 2
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical class CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 1
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
229910052777 Praseodymium Inorganic materials 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
OIJMIQIDIZASII-UHFFFAOYSA-N benzene;benzoic acid Chemical compound C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 OIJMIQIDIZASII-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
229910000421 cerium(III) oxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000001142 dicarboxylic acid group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002537 isoquinolines Chemical class 0.000 description 1
150000002602 lanthanoids Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
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 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QHMGFQBUOCYLDT-RNFRBKRXSA-N n-(diaminomethylidene)-2-[(2r,5r)-2,5-dimethyl-2,5-dihydropyrrol-1-yl]acetamide Chemical compound C[C@@H]1C=C[C@@H](C)N1CC(=O)N=C(N)N QHMGFQBUOCYLDT-RNFRBKRXSA-N 0.000 description 1
ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910001404 rare earth metal oxide Inorganic materials 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
239000000377 silicon dioxide Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
239000006200 vaporizer Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyridine Compounds (AREA)
Pyrrole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

DD90343536A 1989-08-23 1990-08-20 Verfahren zur herstellung von aldehyden DD298085A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3927786A DE3927786A1 (de)	1989-08-23	1989-08-23	Verfahren zur herstellung von aldehyden

Publications (1)

Publication Number	Publication Date
DD298085A5 true DD298085A5 (de)	1992-02-06

Family

ID=6387670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343536A DD298085A5 (de)	1989-08-23	1990-08-20	Verfahren zur herstellung von aldehyden

Country Status (6)

Country	Link
US (1)	US5059716A (fr)
EP (1)	EP0414065B1 (fr)
JP (1)	JP2728553B2 (fr)
DD (1)	DD298085A5 (fr)
DE (2)	DE3927786A1 (fr)
ES (1)	ES2062225T3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5321166A (en) *	1992-03-03	1994-06-14	Hoffmann-La Roche Inc.	Method for the production of aldehydes
DE4431987A1 (de) *	1994-09-08	1996-03-28	Hoechst Ag	Verfahren zur Herstellung von Aldehyden durch katalytische Gasphasenhydrierung von Carbonsäuren oder ihre Derivate mit Hilfe eines Zinnkatalysators
DE4443704A1 (de)	1994-12-08	1996-06-13	Basf Ag	Verfahren zur Herstellung von Aldehyden
US6121498A (en) *	1998-04-30	2000-09-19	Eastman Chemical Company	Method for producing acetaldehyde from acetic acid
JP4047546B2 (ja) *	1998-08-27	2008-02-13	独立行政法人科学技術振興機構	カルボン酸類の直接水素化によるアルデヒド類の触媒的合成
JP2000178254A (ja)	1998-12-18	2000-06-27	Koei Chem Co Ltd	ヘテロ芳香族アルデヒド類の製造方法
US7816565B2 (en) *	2008-07-31	2010-10-19	Celanese International Corporation	Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst
AU2010270797B2 (en)	2009-07-08	2015-03-19	Dermira (Canada), Inc.	TOFA analogs useful in treating dermatological disorders or conditions
CN102010306B (zh) *	2010-11-23	2012-12-26	太仓浦源医药原料有限公司	3，3-二甲基丁醛的制备方法
CN112473719B (zh) *	2021-01-25	2021-06-29	潍坊科技学院	一种多孔碳氮材料负载纳米双金属催化剂的制备方法及其在苯甲酸加氢反应中的使用方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3994936A (en) *	1973-10-29	1976-11-30	Hoffmann-La Roche Inc.	Catalytic rearrangement
DE3021701A1 (de) *	1980-06-10	1981-12-17	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von aromatischen aldehyden
EP0150961B1 (fr) *	1984-01-18	1988-05-11	Mitsubishi Kasei Corporation	Procédé catalytique pour la préparation d'aldéhydes aromatiques
NL8701063A (nl) *	1987-05-06	1988-12-01	Stamicarbon	Werkwijze voor de bereiding van benzaldehyde in de gasfase.
FR2617837B1 (fr) *	1987-07-10	1989-12-01	Rhone Poulenc Chimie	Procede de preparation d'aldehydes aromatiques
DE3728764A1 (de) *	1987-08-28	1989-03-30	Basf Ag	Verfahren zur herstellung von aldehyden aus carbonsaeuren oder deren derivaten

1989
- 1989-08-23 DE DE3927786A patent/DE3927786A1/de not_active Withdrawn
1990
- 1990-08-08 US US07/564,226 patent/US5059716A/en not_active Expired - Fee Related
- 1990-08-10 EP EP90115371A patent/EP0414065B1/fr not_active Expired - Lifetime
- 1990-08-10 DE DE90115371T patent/DE59004300D1/de not_active Expired - Fee Related
- 1990-08-10 ES ES90115371T patent/ES2062225T3/es not_active Expired - Lifetime
- 1990-08-16 JP JP2215110A patent/JP2728553B2/ja not_active Expired - Lifetime
- 1990-08-20 DD DD90343536A patent/DD298085A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES2062225T3 (es)	1994-12-16
DE59004300D1 (de)	1994-03-03
EP0414065A2 (fr)	1991-02-27
US5059716A (en)	1991-10-22
DE3927786A1 (de)	1991-02-28
JP2728553B2 (ja)	1998-03-18
EP0414065A3 (en)	1991-12-04
EP0414065B1 (fr)	1994-01-19
JPH03118344A (ja)	1991-05-20

Legal Events

Date	Code	Title	Description
2000-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0700890B1 (fr)	1999-12-01	Procédé pour la préparation d'aldéhydes par hydrogénation catalytique en phase gazeuse d'acides carboxyliques ou de leurs dérivés utilisant un catalyseur d'étain
EP0088328B1 (fr)	1986-07-30	Catalyseur d'oxydation, en particulier pour la préparation d'acide méthacrylique par l'oxydation de la méthacroléine
DE2834554B2 (de)	1980-08-21	Phosphor und Vanadin als Substrat sowie einen Promotor enthaltender Katalysator und seine Verwendung zur Herstellung von Maleinsäureanhydrid
EP0046840B1 (fr)	1983-10-05	Procédé pour la déshydrogénation oxydante d'acide butyrique en acide méthacrylique
DD298085A5 (de)	1992-02-06	Verfahren zur herstellung von aldehyden
DE4203220A1 (de)	1993-08-12	Verfahren zur herstellung von cyclohexen durch partielle hydrierung von benzol
DE69512610T2 (de)	2000-12-07	Verfahren zur Herstellung von Alpha-Phenylethylalkohol
DE1950094C3 (de)	1974-05-16	Verfahren zur Herstellung von o-Methylphenolen
US5336810A (en)	1994-08-09	Hydrogenation of benzoic acid and catalyst suitable therefor
DE19709488A1 (de)	1998-09-10	Verfahren zur N-Alkylierung von Aminen
DE69603377T2 (de)	2000-02-17	Ammoxidationskatalysatoren und Verfahren zu ihrer Herstellung
DE2430567A1 (de)	1976-01-15	Verfahren zur herstellung von anthrachinon
EP0777639B1 (fr)	1998-12-09	Procede de preparation d'aldehydes aromatiques
DE2235992A1 (de)	1973-02-01	Verfahren zur herstellung gesaettigter aliphatischer amine
EP2155661B1 (fr)	2014-09-10	Procédé de fabrication de nitriles
DE19718742A1 (de)	1998-11-05	Verfahren zur Herstellung von aromatischen Aldehyden durch katalytische Gasphasenhydrierung der Carbonsäuren
DE2454587C2 (de)	1984-04-26	Verfahren zur Herstellung von Methacrylsäure
EP0716070B1 (fr)	1998-08-12	Procédé pour la préparation d'aldéhydes
DE2160649A1 (de)	1973-06-14	Verfahren zur herstellung von allylacetat
DE10121028A1 (de)	2002-01-31	Verfahren zur Herstellung von Aldehyden
DE4304003A1 (de)	1994-08-18	Verfahren zur Herstellung von Acylcyclopropanen
EP0001384B1 (fr)	1983-07-27	Procédé d'ortho-alkylation de phénols
DE4428994A1 (de)	1996-02-22	Verfahren zur Herstellung von aromatischen Aldehyden
DE2042815A1 (de)	1971-03-11	Verfahren zur Herstellung von Aldehyden oder Ketonen durch katal} tische Oxydation von Olefinen bzw Alkylaromaten sowie Verfahren zur Herstellung von Vanadiumoxid Katalysa toren
DE4411657A1 (de)	1995-10-05	Verfahren zur Herstellung von 6-Hydroxymethylchinolinen