DE1239675B - Verfahren zur Herstellung von Adipinsaeure durch katalytische Oxydation von Cyclohexan - Google Patents
Verfahren zur Herstellung von Adipinsaeure durch katalytische Oxydation von CyclohexanInfo
- Publication number
- DE1239675B DE1239675B DEJ20210A DEJ0020210A DE1239675B DE 1239675 B DE1239675 B DE 1239675B DE J20210 A DEJ20210 A DE J20210A DE J0020210 A DEJ0020210 A DE J0020210A DE 1239675 B DE1239675 B DE 1239675B
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexane
- oxidation
- mixture
- water
- parts
- 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
- 230000003647 oxidation Effects 0.000 title claims description 27
- 238000007254 oxidation reaction Methods 0.000 title claims description 27
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 24
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 11
- 239000001361 adipic acid Substances 0.000 title claims description 9
- 235000011037 adipic acid Nutrition 0.000 title claims description 9
- 230000003197 catalytic effect Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- 238000001256 steam distillation Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 235000013832 Valeriana officinalis Nutrition 0.000 claims 1
- 244000126014 Valeriana officinalis Species 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000000855 fermentation Methods 0.000 claims 1
- 230000004151 fermentation Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000011068 loading method Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 125000005609 naphthenate group Chemical group 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 235000016788 valerian Nutrition 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 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
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
-
- 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
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/316—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with oxides of nitrogen or nitrogen-containing mineral acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24717/60A GB914510A (en) | 1960-07-15 | 1960-07-15 | Process for the manufacture of adipic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1239675B true DE1239675B (de) | 1967-05-03 |
Family
ID=10216133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ20210A Pending DE1239675B (de) | 1960-07-15 | 1961-07-07 | Verfahren zur Herstellung von Adipinsaeure durch katalytische Oxydation von Cyclohexan |
Country Status (5)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1044446A (en) * | 1963-03-30 | 1966-09-28 | Inst Chemii Ogolnej | Improvements in or relating to a method of distilling chemical substances |
| FR2749299B1 (fr) † | 1996-06-04 | 1998-07-17 | Rhone Poulenc Fibres | Procede de purification de l'acide adipique dans l'eau |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2557282A (en) * | 1949-03-31 | 1951-06-19 | Du Pont | Adipic acid process |
| DE854505C (de) * | 1944-03-18 | 1952-11-04 | Basf Ag | Verfahren zur Herstellung von aliphatischen Dicarbonsaeuren |
| US2703331A (en) * | 1953-11-06 | 1955-03-01 | Du Pont | Process for separating adipic acid precursors |
-
0
- NL NL267041D patent/NL267041A/xx unknown
-
1960
- 1960-07-15 GB GB24717/60A patent/GB914510A/en not_active Expired
-
1961
- 1961-07-07 DE DEJ20210A patent/DE1239675B/de active Pending
- 1961-07-13 FR FR867949A patent/FR1304056A/fr not_active Expired
- 1961-07-14 CH CH832061A patent/CH409915A/de unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE854505C (de) * | 1944-03-18 | 1952-11-04 | Basf Ag | Verfahren zur Herstellung von aliphatischen Dicarbonsaeuren |
| US2557282A (en) * | 1949-03-31 | 1951-06-19 | Du Pont | Adipic acid process |
| US2703331A (en) * | 1953-11-06 | 1955-03-01 | Du Pont | Process for separating adipic acid precursors |
Also Published As
| Publication number | Publication date |
|---|---|
| CH409915A (de) | 1966-03-31 |
| FR1304056A (fr) | 1962-09-21 |
| NL267041A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB914510A (en) | 1963-01-02 |
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