DE1618514C3 - - Google Patents
Info
- Publication number
- DE1618514C3 DE1618514C3 DE19671618514 DE1618514A DE1618514C3 DE 1618514 C3 DE1618514 C3 DE 1618514C3 DE 19671618514 DE19671618514 DE 19671618514 DE 1618514 A DE1618514 A DE 1618514A DE 1618514 C3 DE1618514 C3 DE 1618514C3
- Authority
- DE
- Germany
- Prior art keywords
- boric acid
- oxidation
- hydrolysis
- zone
- water
- 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
- 239000004327 boric acid Substances 0.000 claims description 79
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 76
- 238000007254 oxidation reaction Methods 0.000 claims description 55
- 230000003647 oxidation Effects 0.000 claims description 47
- 238000006460 hydrolysis reaction Methods 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000001639 boron compounds Chemical class 0.000 claims description 19
- 239000012535 impurity Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000005712 crystallization Effects 0.000 claims description 17
- -1 acyclic hydrocarbons Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 239000012452 mother liquor Substances 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 235000010338 boric acid Nutrition 0.000 description 77
- 229960002645 boric acid Drugs 0.000 description 76
- 150000002430 hydrocarbons Chemical class 0.000 description 23
- 239000004215 Carbon black (E152) Substances 0.000 description 19
- 239000008346 aqueous phase Substances 0.000 description 17
- 235000012970 cakes Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 238000011084 recovery Methods 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 239000000727 fraction Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- HWDBVKSLZVOFIY-UHFFFAOYSA-N [O-]B([O-])OC1CCCCC1 Chemical compound [O-]B([O-])OC1CCCCC1 HWDBVKSLZVOFIY-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 3
- CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 description 3
- DDTBPAQBQHZRDW-UHFFFAOYSA-N Cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N Decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
- FGDMBVPPHHAFPN-UHFFFAOYSA-M B(OC1CCCCC1)([O-])O[O-] Chemical compound B(OC1CCCCC1)([O-])O[O-] FGDMBVPPHHAFPN-UHFFFAOYSA-M 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N Cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N Cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- PWVHLUKAENFZIA-UHFFFAOYSA-N cyclohexanol;cyclohexanone Chemical compound OC1CCCCC1.O=C1CCCCC1 PWVHLUKAENFZIA-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 150000004977 peroxyborates Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55419566A | 1966-05-31 | 1966-05-31 | |
| US55419566 | 1966-05-31 | ||
| DEH0062896 | 1967-05-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1618514A1 DE1618514A1 (de) | 1971-04-29 |
| DE1618514B2 DE1618514B2 (de) | 1976-02-12 |
| DE1618514C3 true DE1618514C3 (US08063081-20111122-C00115.png) | 1976-10-07 |
Family
ID=24212409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618514 Granted DE1618514B2 (de) | 1966-05-31 | 1967-05-31 | Verfahren zur oxydation von alicyclischen kohlenwasserstoffen |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895067A (en) * | 1970-06-15 | 1975-07-15 | Monsanto Co | Boric acid recovery |
| US4058565A (en) * | 1972-12-08 | 1977-11-15 | Bayer Aktiengesellschaft | Process for oxidizing hydrocarbons |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240820A (en) * | 1962-01-16 | 1966-03-15 | Halcon International Inc | Process for the separation of boric acid from organic liquids |
| NL301390A (US08063081-20111122-C00115.png) * | 1962-12-13 |
-
1966
- 1966-05-31 US US554195A patent/US3475500A/en not_active Expired - Lifetime
-
1967
- 1967-05-24 GB GB24092/67A patent/GB1128723A/en not_active Expired
- 1967-05-24 NL NL676707215A patent/NL152535B/xx unknown
- 1967-05-24 BE BE698908D patent/BE698908A/xx unknown
- 1967-05-26 LU LU53759D patent/LU53759A1/xx unknown
- 1967-05-29 IL IL28057A patent/IL28057A/en unknown
- 1967-05-31 SE SE07611/67*A patent/SE336777B/xx unknown
- 1967-05-31 CH CH766467A patent/CH474461A/fr not_active IP Right Cessation
- 1967-05-31 DE DE19671618514 patent/DE1618514B2/de active Granted
- 1967-05-31 ES ES341200A patent/ES341200A1/es not_active Expired
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