DE1468010C - - Google Patents
Info
- Publication number
- DE1468010C DE1468010C DE19631468010 DE1468010A DE1468010C DE 1468010 C DE1468010 C DE 1468010C DE 19631468010 DE19631468010 DE 19631468010 DE 1468010 A DE1468010 A DE 1468010A DE 1468010 C DE1468010 C DE 1468010C
- Authority
- DE
- Germany
- Prior art keywords
- boric acid
- crystals
- oxidation
- dehydration
- acid
- 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
- 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 35
- 238000006297 dehydration reaction Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 238000007254 oxidation reaction Methods 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 20
- 239000002245 particle Substances 0.000 claims description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 14
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 239000002002 slurry Substances 0.000 claims description 11
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000005712 crystallization Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 150000001639 boron compounds Chemical class 0.000 claims description 4
- WZRXFPOWHQQSRJ-UHFFFAOYSA-N cyclohexyloxyboronic acid Chemical compound OB(O)OC1CCCCC1 WZRXFPOWHQQSRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 241000158147 Sator Species 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000001771 impaired Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 239000010419 fine particle Substances 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- 229940109615 Oxy 10 Drugs 0.000 claims 1
- 108060008443 TPPP Proteins 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000002826 coolant Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 229960002645 boric acid Drugs 0.000 description 20
- 235000010338 boric acid Nutrition 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000008079 hexane Substances 0.000 description 3
- CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 1
- 241000282941 Rangifer tarandus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- -1 boric acid ester Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US244388A US3324186A (en) | 1962-12-13 | 1962-12-13 | Hydrocarbon oxidation process |
| US24438862 | 1962-12-13 | ||
| DEH0051124 | 1963-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1468010A1 DE1468010A1 (de) | 1969-01-23 |
| DE1468010C true DE1468010C (zh) | 1973-01-18 |
Family
ID=22922526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468010 Granted DE1468010A1 (de) | 1962-12-13 | 1963-12-13 | Verfahren zur Oxydation von Kohlenwasserstoffen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3324186A (zh) |
| BE (1) | BE640732A (zh) |
| CH (1) | CH422784A (zh) |
| DE (1) | DE1468010A1 (zh) |
| ES (1) | ES294469A1 (zh) |
| GB (1) | GB1068948A (zh) |
| LU (1) | LU44926A1 (zh) |
| NL (2) | NL140739B (zh) |
| NO (1) | NO122919B (zh) |
| SE (1) | SE325268B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1448752A (fr) * | 1964-08-18 | 1966-03-18 | Inst Francais Du Petrole | Procédé d'oxydation des hydrocarbures |
| US3415621A (en) * | 1965-12-17 | 1968-12-10 | Shell Oil Co | Crystalline metaboric acid by hydrolysis of secondary alkyl borate ester |
| US3475500A (en) * | 1966-05-31 | 1969-10-28 | Halcon International Inc | Recovery of boron compounds in the oxidation of hydrocarbons |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1947989A (en) * | 1928-06-20 | 1934-02-20 | Firm A Riebeck Sche Montanwerk | Method of oxidizing hydrocarbons |
| BE541333A (fr) * | 1955-09-15 | 1959-08-14 | Belge Produits Chimiques Sa | Procede et appareillage pour la separation continue d'alcools gras superieurs d'avec des hydrocarbures. |
| US3109864A (en) * | 1961-09-26 | 1963-11-05 | Halcon International Inc | Oxidation of hydrocarbons |
-
0
- NL NL301390D patent/NL301390A/xx unknown
-
1962
- 1962-12-13 US US244388A patent/US3324186A/en not_active Expired - Lifetime
-
1963
- 1963-12-03 LU LU44926D patent/LU44926A1/xx unknown
- 1963-12-03 BE BE640732A patent/BE640732A/xx unknown
- 1963-12-05 NL NL63301390A patent/NL140739B/xx unknown
- 1963-12-09 GB GB48593/63A patent/GB1068948A/en not_active Expired
- 1963-12-11 CH CH1519763A patent/CH422784A/fr unknown
- 1963-12-12 NO NO151211A patent/NO122919B/no unknown
- 1963-12-13 ES ES294469A patent/ES294469A1/es not_active Expired
- 1963-12-13 SE SE13889/63A patent/SE325268B/xx unknown
- 1963-12-13 DE DE19631468010 patent/DE1468010A1/de active Granted
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