DE1965645A1 - Verfahren zur Herstellung geradkettiger Fettsaeuren - Google Patents
Verfahren zur Herstellung geradkettiger FettsaeurenInfo
- Publication number
- DE1965645A1 DE1965645A1 DE19691965645 DE1965645A DE1965645A1 DE 1965645 A1 DE1965645 A1 DE 1965645A1 DE 19691965645 DE19691965645 DE 19691965645 DE 1965645 A DE1965645 A DE 1965645A DE 1965645 A1 DE1965645 A1 DE 1965645A1
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- acid
- carboxylic acids
- atoms
- straight
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000005480 straight-chain fatty acid group Chemical group 0.000 title description 3
- 239000003513 alkali Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 150000001735 carboxylic acids Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 239000004711 α-olefin Substances 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000000180 1,2-diols Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000033444 hydroxylation Effects 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940015975 1,2-hexanediol Drugs 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000000640 hydroxylating effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- VIORFPNRPQIEEI-UHFFFAOYSA-N 2-acetyloxyoctadecyl acetate Chemical compound CCCCCCCCCCCCCCCCC(OC(C)=O)COC(C)=O VIORFPNRPQIEEI-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 102100026368 E3 ubiquitin-protein ligase RNF146 Human genes 0.000 description 1
- 101710162569 E3 ubiquitin-protein ligase RNF146 Proteins 0.000 description 1
- 241000278013 Iduna Species 0.000 description 1
- 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 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Substances CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691965645 DE1965645A1 (de) | 1969-12-31 | 1969-12-31 | Verfahren zur Herstellung geradkettiger Fettsaeuren |
| RO6476870A RO56877A (enrdf_load_stackoverflow) | 1969-12-31 | 1970-10-23 | |
| SE1605170A SE374737B (enrdf_load_stackoverflow) | 1969-12-31 | 1970-11-26 | |
| NL7017316A NL7017316A (enrdf_load_stackoverflow) | 1969-12-31 | 1970-11-26 | |
| GB5961970A GB1274619A (en) | 1969-12-31 | 1970-12-16 | Process for the preparation of straight-chain fatty acids |
| CH1919570A CH558320A (de) | 1969-12-31 | 1970-12-28 | Verfahren zur herstellung geradkettiger fettsaeuren. |
| BE760961A BE760961A (fr) | 1969-12-31 | 1970-12-29 | Procede de preparation d'acides gras a chaine droite |
| JP12194570A JPS5012407B1 (enrdf_load_stackoverflow) | 1969-12-31 | 1970-12-29 | |
| AT1175270A AT305233B (de) | 1969-12-31 | 1970-12-30 | Verfahren zur Herstellung geradkettiger Fettsäuren |
| ES386920A ES386920A1 (es) | 1969-12-31 | 1970-12-30 | Procedimiento para la obtencion de acidos carboxilicos ali-faticos, exclusivamente de cadena recta, con mas de cuatro atomos de carbono. |
| FR7047359A FR2080398A5 (enrdf_load_stackoverflow) | 1969-12-31 | 1970-12-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691965645 DE1965645A1 (de) | 1969-12-31 | 1969-12-31 | Verfahren zur Herstellung geradkettiger Fettsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1965645A1 true DE1965645A1 (de) | 1971-07-15 |
Family
ID=5755344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691965645 Pending DE1965645A1 (de) | 1969-12-31 | 1969-12-31 | Verfahren zur Herstellung geradkettiger Fettsaeuren |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5252215U (enrdf_load_stackoverflow) * | 1975-10-13 | 1977-04-14 |
-
1969
- 1969-12-31 DE DE19691965645 patent/DE1965645A1/de active Pending
-
1970
- 1970-10-23 RO RO6476870A patent/RO56877A/ro unknown
- 1970-11-26 NL NL7017316A patent/NL7017316A/xx unknown
- 1970-11-26 SE SE1605170A patent/SE374737B/xx unknown
- 1970-12-16 GB GB5961970A patent/GB1274619A/en not_active Expired
- 1970-12-28 CH CH1919570A patent/CH558320A/xx not_active IP Right Cessation
- 1970-12-29 JP JP12194570A patent/JPS5012407B1/ja active Pending
- 1970-12-29 BE BE760961A patent/BE760961A/xx unknown
- 1970-12-30 FR FR7047359A patent/FR2080398A5/fr not_active Expired
- 1970-12-30 AT AT1175270A patent/AT305233B/de not_active IP Right Cessation
- 1970-12-30 ES ES386920A patent/ES386920A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5012407B1 (enrdf_load_stackoverflow) | 1975-05-12 |
| AT305233B (de) | 1973-02-12 |
| FR2080398A5 (enrdf_load_stackoverflow) | 1971-11-12 |
| RO56877A (enrdf_load_stackoverflow) | 1974-08-01 |
| CH558320A (de) | 1975-01-31 |
| SE374737B (enrdf_load_stackoverflow) | 1975-03-17 |
| ES386920A1 (es) | 1973-04-16 |
| GB1274619A (en) | 1972-05-17 |
| BE760961A (fr) | 1971-06-29 |
| NL7017316A (enrdf_load_stackoverflow) | 1971-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH511790A (de) | Verfahren zur Herstellung ungesättigter Ester von Carbonsäuren | |
| DE2709438A1 (de) | Verfahren zur herstellung hoeherer alkylcarbonsaeuren | |
| DE2447069C2 (de) | Verfahren zur Herstellung von Carbonsäureestern | |
| EP0011842B1 (de) | Verfahren zum Abbau von Ameisensäureestern | |
| DE2856791C2 (de) | Integriertes Kreislaufverfahren zur Herstellung von Vinylacetat | |
| DE1251296C2 (de) | Verfahren zur herstellung hoeherer primaerer alkohole | |
| EP0010236B2 (de) | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-butandiol | |
| EP0025940B1 (de) | Verfahren zur Hydroxylierung olefinisch ungesättigter Verbindungen | |
| EP0042928B1 (de) | Verfahren zur Herstellung von Fettsäureestern | |
| DE2411440C3 (enrdf_load_stackoverflow) | ||
| DE1965645A1 (de) | Verfahren zur Herstellung geradkettiger Fettsaeuren | |
| DE3139709C2 (de) | Verfahren zur Herstellung von Acetalhehyd | |
| DE3034421C2 (enrdf_load_stackoverflow) | ||
| DE1543016A1 (de) | Verfahren zur Herstellung von Alkoholen | |
| DE2825347C2 (de) | Verfahren zur Herstellung von p-Hydroxymethylbenzoesäurealkylestern | |
| EP0047831A1 (de) | Verfahren zur Herstellung von überwiegend linearen aliphatischen Carbonsäureestern | |
| DE2750719C2 (enrdf_load_stackoverflow) | ||
| DE2652202C2 (de) | Verfahren zur Herstellung von 3,7-Dimethyl-octan-7-ol-1-al oder dessen Ester | |
| DE3825296A1 (de) | Verfahren zur herstellung von pentensaeurealkylestern | |
| DE2165858C3 (de) | Verfahren zur Herstellung von höhermolekularen, aliphatischen Monocarbonsäuren | |
| DE965696C (de) | Verfahren zur Herstellung von Estern von Glykolmono-(oxymethyl)-aethern | |
| DE854503C (de) | Verfahren zur Herstellung von hoehermolekularen Umwandlungs-produkten von Allylverbindungen | |
| DE743223C (de) | Verfahren zur Herstellung von carbonsauren Salzen | |
| DE767911C (de) | Verfahren zur Herstellung von Gemischen aliphatischer Carbonsaeuren | |
| DE855247C (de) | Verfahren zur Spaltung von Acetalen |