DE1618510C3 - Kontinuierliches Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen - Google Patents
Kontinuierliches Verfahren zur Oxydation von Cyclohexan in Gegenwart von BorverbindungenInfo
- Publication number
- DE1618510C3 DE1618510C3 DE1618510A DE1618510A DE1618510C3 DE 1618510 C3 DE1618510 C3 DE 1618510C3 DE 1618510 A DE1618510 A DE 1618510A DE 1618510 A DE1618510 A DE 1618510A DE 1618510 C3 DE1618510 C3 DE 1618510C3
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- boric acid
- acid
- cyclohexane
- washing
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 51
- 230000003647 oxidation Effects 0.000 title claims description 42
- 238000007254 oxidation reaction Methods 0.000 title claims description 42
- 150000001639 boron compounds Chemical class 0.000 title claims description 11
- 238000010924 continuous production Methods 0.000 title claims 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 64
- 239000004327 boric acid Substances 0.000 claims description 62
- 238000005406 washing Methods 0.000 claims description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 22
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 16
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 9
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 8
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 7
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 7
- 238000004140 cleaning Methods 0.000 claims description 7
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001638 boron Chemical class 0.000 claims description 2
- 239000000356 contaminant Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 239000006227 byproduct Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012065 filter cake Substances 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- NRGYUJRYGPFNCM-UHFFFAOYSA-N B(O)(O)O.OCCCCCC(=O)O Chemical compound B(O)(O)O.OCCCCCC(=O)O NRGYUJRYGPFNCM-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 208000000260 Warts Diseases 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 230000003292 diminished effect Effects 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 201000010153 skin papilloma Diseases 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
- 229960002645 boric acid Drugs 0.000 description 47
- 235000010338 boric acid Nutrition 0.000 description 47
- 238000002474 experimental method Methods 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54968266A | 1966-05-12 | 1966-05-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1618510A1 DE1618510A1 (de) | 1971-04-22 |
| DE1618510B2 DE1618510B2 (enExample) | 1974-07-18 |
| DE1618510C3 true DE1618510C3 (de) | 1975-08-14 |
Family
ID=24193992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1618510A Expired DE1618510C3 (de) | 1966-05-12 | 1967-05-12 | Kontinuierliches Verfahren zur Oxydation von Cyclohexan in Gegenwart von Borverbindungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3492355A (enExample) |
| BE (1) | BE697913A (enExample) |
| CH (1) | CH484852A (enExample) |
| DE (1) | DE1618510C3 (enExample) |
| DK (1) | DK119703B (enExample) |
| ES (1) | ES340450A1 (enExample) |
| GB (1) | GB1197472A (enExample) |
| IL (1) | IL27955A (enExample) |
| LU (1) | LU53588A1 (enExample) |
| NL (1) | NL6706296A (enExample) |
| SE (1) | SE334155B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450291A (en) * | 1983-05-02 | 1984-05-22 | Monsanto Company | Decontamination of KA oil refinement waste stream |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232704A (en) * | 1962-03-21 | 1966-02-01 | Exxon Research Engineering Co | Process for recovering boric acid |
-
1966
- 1966-05-12 US US549682A patent/US3492355A/en not_active Expired - Lifetime
-
1967
- 1967-05-02 BE BE697913D patent/BE697913A/xx unknown
- 1967-05-03 LU LU53588D patent/LU53588A1/xx unknown
- 1967-05-05 NL NL6706296A patent/NL6706296A/xx unknown
- 1967-05-09 GB GB21435/67A patent/GB1197472A/en not_active Expired
- 1967-05-10 IL IL27955A patent/IL27955A/en unknown
- 1967-05-10 DK DK246067AA patent/DK119703B/da unknown
- 1967-05-11 CH CH665767A patent/CH484852A/fr not_active IP Right Cessation
- 1967-05-12 DE DE1618510A patent/DE1618510C3/de not_active Expired
- 1967-05-12 ES ES340450A patent/ES340450A1/es not_active Expired
- 1967-05-12 SE SE06689/67A patent/SE334155B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1618510B2 (enExample) | 1974-07-18 |
| DE1618510A1 (de) | 1971-04-22 |
| CH484852A (fr) | 1970-01-31 |
| BE697913A (enExample) | 1967-11-03 |
| LU53588A1 (enExample) | 1969-03-20 |
| ES340450A1 (es) | 1968-06-01 |
| US3492355A (en) | 1970-01-27 |
| NL6706296A (enExample) | 1967-11-13 |
| IL27955A (en) | 1971-01-28 |
| GB1197472A (en) | 1970-07-08 |
| SE334155B (enExample) | 1971-04-19 |
| DK119703B (da) | 1971-02-15 |
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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 |