DE1643915A1 - Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen Aldehyden - Google Patents
Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen AldehydenInfo
- Publication number
- DE1643915A1 DE1643915A1 DE19681643915 DE1643915A DE1643915A1 DE 1643915 A1 DE1643915 A1 DE 1643915A1 DE 19681643915 DE19681643915 DE 19681643915 DE 1643915 A DE1643915 A DE 1643915A DE 1643915 A1 DE1643915 A1 DE 1643915A1
- Authority
- DE
- Germany
- Prior art keywords
- aldehydes
- amalgam
- methanol
- aldehyde
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001299 aldehydes Chemical class 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 13
- 125000001931 aliphatic group Chemical group 0.000 title claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 15
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 229910001023 sodium amalgam Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000567 Amalgam (chemistry) Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000005868 electrolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 229910000497 Amalgam Inorganic materials 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- -1 aliphatic alcohols Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 4
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-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
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- LPRMANDJSIXLBP-UHFFFAOYSA-N 5-hydroxy-4,4-dimethylpentanenitrile Chemical compound OCC(C)(C)CCC#N LPRMANDJSIXLBP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKJVKIURQSVEQB-UHFFFAOYSA-N 4,4-dimethyl-5-oxopentanenitrile Chemical compound O=CC(C)(C)CCC#N HKJVKIURQSVEQB-UHFFFAOYSA-N 0.000 description 1
- AMUXIQHQXOKMTN-UHFFFAOYSA-N 4-ethyl-4-formylhexanenitrile Chemical compound CCC(CC)(C=O)CCC#N AMUXIQHQXOKMTN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 241000379208 Latris Species 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681643915 DE1643915A1 (de) | 1968-01-02 | 1968-01-02 | Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen Aldehyden |
| LU57669D LU57669A1 (enrdf_load_stackoverflow) | 1968-01-02 | 1968-02-24 | |
| CH1939368A CH508566A (de) | 1968-01-02 | 1968-12-30 | Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen Aldehyden zu den entsprechenden Alkoholen |
| FR1600095D FR1600095A (enrdf_load_stackoverflow) | 1968-01-02 | 1968-12-30 | |
| AT1267368A AT286248B (de) | 1968-01-02 | 1968-12-30 | Verfahren zur Reduktion aliphatischer oder cycloaliphatischer Aldehyde |
| BE726290D BE726290A (enrdf_load_stackoverflow) | 1968-01-02 | 1968-12-30 | |
| NL6818853A NL6818853A (enrdf_load_stackoverflow) | 1968-01-02 | 1968-12-31 | |
| GB37469A GB1213612A (en) | 1968-01-02 | 1969-01-02 | Process for producing aliphatic and cycloaliphatic alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681643915 DE1643915A1 (de) | 1968-01-02 | 1968-01-02 | Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen Aldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643915A1 true DE1643915A1 (de) | 1971-07-29 |
Family
ID=5684423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681643915 Pending DE1643915A1 (de) | 1968-01-02 | 1968-01-02 | Verfahren zur Reduktion von aliphatischen oder cycloaliphatischen Aldehyden |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT286248B (enrdf_load_stackoverflow) |
| BE (1) | BE726290A (enrdf_load_stackoverflow) |
| CH (1) | CH508566A (enrdf_load_stackoverflow) |
| DE (1) | DE1643915A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1600095A (enrdf_load_stackoverflow) |
| GB (1) | GB1213612A (enrdf_load_stackoverflow) |
| LU (1) | LU57669A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6818853A (enrdf_load_stackoverflow) |
-
1968
- 1968-01-02 DE DE19681643915 patent/DE1643915A1/de active Pending
- 1968-02-24 LU LU57669D patent/LU57669A1/xx unknown
- 1968-12-30 AT AT1267368A patent/AT286248B/de not_active IP Right Cessation
- 1968-12-30 BE BE726290D patent/BE726290A/xx unknown
- 1968-12-30 CH CH1939368A patent/CH508566A/de not_active IP Right Cessation
- 1968-12-30 FR FR1600095D patent/FR1600095A/fr not_active Expired
- 1968-12-31 NL NL6818853A patent/NL6818853A/xx unknown
-
1969
- 1969-01-02 GB GB37469A patent/GB1213612A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1213612A (en) | 1970-11-25 |
| LU57669A1 (enrdf_load_stackoverflow) | 1969-04-15 |
| CH508566A (de) | 1971-06-15 |
| FR1600095A (enrdf_load_stackoverflow) | 1970-07-20 |
| BE726290A (enrdf_load_stackoverflow) | 1969-05-29 |
| NL6818853A (enrdf_load_stackoverflow) | 1969-07-04 |
| AT286248B (de) | 1970-11-25 |
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