DE1914062C3 - Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen - Google Patents
Verfahren zur Oxydation von Cyclohexan in Gegenwart von BorverbindungenInfo
- Publication number
- DE1914062C3 DE1914062C3 DE1914062A DE1914062A DE1914062C3 DE 1914062 C3 DE1914062 C3 DE 1914062C3 DE 1914062 A DE1914062 A DE 1914062A DE 1914062 A DE1914062 A DE 1914062A DE 1914062 C3 DE1914062 C3 DE 1914062C3
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- cyclohexane
- boric acid
- cyclohexanol
- boron compounds
- 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 31
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 27
- 230000003647 oxidation Effects 0.000 title claims description 22
- 238000007254 oxidation reaction Methods 0.000 title claims description 22
- 150000001639 boron compounds Chemical class 0.000 title claims description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 37
- 239000004327 boric acid Substances 0.000 claims description 28
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 13
- 238000004140 cleaning Methods 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 230000018044 dehydration Effects 0.000 claims description 9
- 238000006297 dehydration reaction Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- 235000010338 boric acid Nutrition 0.000 description 32
- 229960002645 boric acid Drugs 0.000 description 30
- 239000007789 gas Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 125000005619 boric acid group Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- WZRXFPOWHQQSRJ-UHFFFAOYSA-N cyclohexyloxyboronic acid Chemical group OB(O)OC1CCCCC1 WZRXFPOWHQQSRJ-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- C07C29/52—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 in the presence of mineral boron compounds with, when necessary, hydrolysis of the intermediate formed
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1914062A DE1914062C3 (de) | 1969-03-20 | 1969-03-20 | Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen |
| NL7003360A NL7003360A (enExample) | 1969-03-20 | 1970-03-10 | |
| TR17807A TR17807A (tr) | 1969-03-20 | 1970-03-17 | Bor bilesiklerinin mevucudiyetinde mesbu hidrokarbonlarin oksidasyonuna yarayan tesislerin temizlenmesine mahsus usul |
| FR7009809A FR2042732A5 (enExample) | 1969-03-20 | 1970-03-19 | |
| RO7062815A RO69431A (ro) | 1969-03-20 | 1970-03-19 | Metoda pentru curatat instalatiile utilizate la oxidarea hidrocarburilor saturate in prezenta compusilor de bor |
| CS701832A CS187306B2 (en) | 1969-03-20 | 1970-03-19 | Method of rinsing cleaning of the devices,used for the oxidation of saturated hydrocarbons in presence of the boron compounds |
| GB1295534D GB1295534A (enExample) | 1969-03-20 | 1970-03-19 | |
| BE747689D BE747689A (fr) | 1969-03-20 | 1970-03-20 | Procede de nettoyage d'installations qui servent a l'oxydation d'hydrocarbures satures en presence de composes de bore |
| BR217657/70A BR7017657D0 (pt) | 1969-03-20 | 1970-03-20 | Processo para limpeza de instalacoes que sao usadas para a oxidacao de hidrocarbonetos saturados na presenca de composto de boro |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1914062A DE1914062C3 (de) | 1969-03-20 | 1969-03-20 | Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1914062A1 DE1914062A1 (de) | 1970-10-08 |
| DE1914062B2 DE1914062B2 (de) | 1973-08-23 |
| DE1914062C3 true DE1914062C3 (de) | 1974-04-11 |
Family
ID=5728682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1914062A Expired DE1914062C3 (de) | 1969-03-20 | 1969-03-20 | Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE747689A (enExample) |
| BR (1) | BR7017657D0 (enExample) |
| CS (1) | CS187306B2 (enExample) |
| DE (1) | DE1914062C3 (enExample) |
| FR (1) | FR2042732A5 (enExample) |
| GB (1) | GB1295534A (enExample) |
| NL (1) | NL7003360A (enExample) |
| RO (1) | RO69431A (enExample) |
| TR (1) | TR17807A (enExample) |
-
1969
- 1969-03-20 DE DE1914062A patent/DE1914062C3/de not_active Expired
-
1970
- 1970-03-10 NL NL7003360A patent/NL7003360A/xx unknown
- 1970-03-17 TR TR17807A patent/TR17807A/xx unknown
- 1970-03-19 FR FR7009809A patent/FR2042732A5/fr not_active Expired
- 1970-03-19 CS CS701832A patent/CS187306B2/cs unknown
- 1970-03-19 RO RO7062815A patent/RO69431A/ro unknown
- 1970-03-19 GB GB1295534D patent/GB1295534A/en not_active Expired
- 1970-03-20 BE BE747689D patent/BE747689A/xx unknown
- 1970-03-20 BR BR217657/70A patent/BR7017657D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1914062B2 (de) | 1973-08-23 |
| DE1914062A1 (de) | 1970-10-08 |
| FR2042732A5 (enExample) | 1971-02-12 |
| TR17807A (tr) | 1976-04-13 |
| BE747689A (fr) | 1970-08-31 |
| NL7003360A (enExample) | 1970-09-22 |
| RO69431A (ro) | 1980-10-30 |
| GB1295534A (enExample) | 1972-11-08 |
| BR7017657D0 (pt) | 1973-01-09 |
| CS187306B2 (en) | 1979-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| 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 |