CH426762A - Procédé de production d'acide adipique par oxydation du cyclohexane - Google Patents
Procédé de production d'acide adipique par oxydation du cyclohexaneInfo
- Publication number
- CH426762A CH426762A CH1147063A CH1147063A CH426762A CH 426762 A CH426762 A CH 426762A CH 1147063 A CH1147063 A CH 1147063A CH 1147063 A CH1147063 A CH 1147063A CH 426762 A CH426762 A CH 426762A
- Authority
- CH
- Switzerland
- Prior art keywords
- phase
- oxidation
- cyclohexane
- adipic acid
- oily
- Prior art date
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 110
- 230000003647 oxidation Effects 0.000 title claims description 59
- 238000007254 oxidation reaction Methods 0.000 title claims description 59
- 239000001361 adipic acid Substances 0.000 title claims description 55
- 235000011037 adipic acid Nutrition 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 49
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 42
- 239000002243 precursor Substances 0.000 claims description 33
- 239000000047 product Substances 0.000 claims description 28
- 239000012071 phase Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 238000003860 storage Methods 0.000 description 6
- 230000005587 bubbling Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000002351 wastewater 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Braking Arrangements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22443562A | 1962-09-18 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH426762A true CH426762A (fr) | 1966-12-31 |
Family
ID=22840667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1147063A CH426762A (fr) | 1962-09-18 | 1963-09-17 | Procédé de production d'acide adipique par oxydation du cyclohexane |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5019533B1 (enEXAMPLES) |
| BE (1) | BE637535A (enEXAMPLES) |
| CH (1) | CH426762A (enEXAMPLES) |
| DE (1) | DE1468280A1 (enEXAMPLES) |
| DK (1) | DK114764B (enEXAMPLES) |
| GB (1) | GB1013619A (enEXAMPLES) |
| LU (1) | LU44452A1 (enEXAMPLES) |
| NL (1) | NL298067A (enEXAMPLES) |
| NO (1) | NO116848B (enEXAMPLES) |
| SE (1) | SE312332B (enEXAMPLES) |
-
0
- NL NL298067D patent/NL298067A/xx unknown
- BE BE637535D patent/BE637535A/xx unknown
-
1963
- 1963-09-16 GB GB36397/63A patent/GB1013619A/en not_active Expired
- 1963-09-17 SE SE10172/63A patent/SE312332B/xx unknown
- 1963-09-17 DK DK437763AA patent/DK114764B/da unknown
- 1963-09-17 NO NO150126A patent/NO116848B/no unknown
- 1963-09-17 CH CH1147063A patent/CH426762A/fr unknown
- 1963-09-17 DE DE19631468280 patent/DE1468280A1/de active Pending
- 1963-09-17 LU LU44452D patent/LU44452A1/xx unknown
- 1963-09-18 JP JP38050087A patent/JPS5019533B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO116848B (enEXAMPLES) | 1969-06-02 |
| LU44452A1 (enEXAMPLES) | 1964-03-17 |
| DK114764B (da) | 1969-08-04 |
| JPS5019533B1 (enEXAMPLES) | 1975-07-08 |
| DE1468280A1 (de) | 1969-01-02 |
| BE637535A (enEXAMPLES) | |
| GB1013619A (en) | 1965-12-15 |
| NL298067A (enEXAMPLES) | |
| SE312332B (enEXAMPLES) | 1969-07-14 |
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