DE2165858C3 - Verfahren zur Herstellung von höhermolekularen, aliphatischen Monocarbonsäuren - Google Patents
Verfahren zur Herstellung von höhermolekularen, aliphatischen MonocarbonsäurenInfo
- Publication number
- DE2165858C3 DE2165858C3 DE19712165858 DE2165858A DE2165858C3 DE 2165858 C3 DE2165858 C3 DE 2165858C3 DE 19712165858 DE19712165858 DE 19712165858 DE 2165858 A DE2165858 A DE 2165858A DE 2165858 C3 DE2165858 C3 DE 2165858C3
- Authority
- DE
- Germany
- Prior art keywords
- olefins
- acids
- oxidation
- molecular weight
- molecule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 aliphatic monocarboxylic acids Chemical class 0.000 title claims 3
- 239000002253 acid Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 6
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 6
- 229940117975 chromium trioxide Drugs 0.000 claims description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 5
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 150000004665 fatty acids Chemical class 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000001993 wax Substances 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000012170 montan wax Substances 0.000 claims 2
- 239000012188 paraffin wax Substances 0.000 claims 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000003925 fat Substances 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000011031 large-scale manufacturing process Methods 0.000 claims 1
- 150000004668 long chain fatty acids Chemical class 0.000 claims 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 229930014626 natural product Natural products 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 238000009896 oxidative bleaching Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 238000005949 ozonolysis reaction Methods 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical class [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712165858 DE2165858C3 (de) | 1971-12-31 | 1971-12-31 | Verfahren zur Herstellung von höhermolekularen, aliphatischen Monocarbonsäuren |
| NL7217549A NL7217549A (https=) | 1971-12-31 | 1972-12-22 | |
| JP411473A JPS4876809A (https=) | 1971-12-31 | 1972-12-28 | |
| CA160,089A CA979006A (en) | 1971-12-31 | 1972-12-28 | Process for the manufacture of high molecular weight aliphatic monocarboxylic acids |
| IT3396972A IT973235B (it) | 1971-12-31 | 1972-12-29 | Procedimento per la preparazione di acidi monocarbossilici alifati ci superiori |
| GB6004872A GB1364214A (en) | 1971-12-31 | 1972-12-29 | Process for the manufacture of aliphatic monocarboxylic acids |
| US05/565,007 US3988331A (en) | 1971-12-31 | 1975-04-04 | Process for the manufacture of high molecular weight aliphatic monocarboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712165858 DE2165858C3 (de) | 1971-12-31 | 1971-12-31 | Verfahren zur Herstellung von höhermolekularen, aliphatischen Monocarbonsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2165858A1 DE2165858A1 (de) | 1973-07-12 |
| DE2165858B2 DE2165858B2 (https=) | 1974-04-25 |
| DE2165858C3 true DE2165858C3 (de) | 1974-11-28 |
Family
ID=5829856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712165858 Expired DE2165858C3 (de) | 1971-12-31 | 1971-12-31 | Verfahren zur Herstellung von höhermolekularen, aliphatischen Monocarbonsäuren |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4876809A (https=) |
| CA (1) | CA979006A (https=) |
| DE (1) | DE2165858C3 (https=) |
| GB (1) | GB1364214A (https=) |
| IT (1) | IT973235B (https=) |
| NL (1) | NL7217549A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029682A (en) * | 1974-12-23 | 1977-06-14 | Emery Industries, Inc. | Soaps and ester-soaps of α-olefin derived high molecular weight acids |
| TW277064B (https=) * | 1993-07-23 | 1996-06-01 | Hoechst Ag |
-
1971
- 1971-12-31 DE DE19712165858 patent/DE2165858C3/de not_active Expired
-
1972
- 1972-12-22 NL NL7217549A patent/NL7217549A/xx not_active Application Discontinuation
- 1972-12-28 JP JP411473A patent/JPS4876809A/ja active Pending
- 1972-12-28 CA CA160,089A patent/CA979006A/en not_active Expired
- 1972-12-29 GB GB6004872A patent/GB1364214A/en not_active Expired
- 1972-12-29 IT IT3396972A patent/IT973235B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT973235B (it) | 1974-06-10 |
| DE2165858B2 (https=) | 1974-04-25 |
| JPS4876809A (https=) | 1973-10-16 |
| CA979006A (en) | 1975-12-02 |
| DE2165858A1 (de) | 1973-07-12 |
| GB1364214A (en) | 1974-08-21 |
| NL7217549A (https=) | 1973-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |