NO116671B - - Google Patents
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- Publication number
- NO116671B NO116671B NO156396A NO15639665A NO116671B NO 116671 B NO116671 B NO 116671B NO 156396 A NO156396 A NO 156396A NO 15639665 A NO15639665 A NO 15639665A NO 116671 B NO116671 B NO 116671B
- Authority
- NO
- Norway
- Prior art keywords
- hydrocarbon
- fed
- oxidation
- liquid
- acid
- Prior art date
Links
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims description 34
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 230000003647 oxidation Effects 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 22
- 229960002645 boric acid Drugs 0.000 claims description 20
- 235000010338 boric acid Nutrition 0.000 claims description 20
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 19
- 230000018044 dehydration Effects 0.000 claims description 19
- 238000006297 dehydration reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 8
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 claims description 8
- 239000004327 boric acid Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 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
- 239000012071 phase Substances 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- -1 borate ester Chemical class 0.000 description 2
- 125000005619 boric acid group Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US338364A US3317581A (en) | 1964-01-17 | 1964-01-17 | Hydrocarbon oxidation process to produce borate ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116671B true NO116671B (nl) | 1969-05-05 |
Family
ID=23324522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO156396A NO116671B (nl) | 1964-01-17 | 1965-01-16 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3317581A (nl) |
| BE (1) | BE658308A (nl) |
| CH (1) | CH437241A (nl) |
| DE (1) | DE1518969B2 (nl) |
| ES (1) | ES308212A1 (nl) |
| FR (1) | FR1424052A (nl) |
| GB (2) | GB1097485A (nl) |
| IL (1) | IL22790A (nl) |
| LU (1) | LU47790A1 (nl) |
| NL (1) | NL142663B (nl) |
| NO (1) | NO116671B (nl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6503884A (nl) * | 1964-04-03 | 1965-10-04 | ||
| US3409698A (en) * | 1966-06-24 | 1968-11-05 | Universal Oil Prod Co | Olefin preparation |
| FR1527718A (fr) * | 1966-07-07 | 1968-06-07 | Inst Francais Du Petrole | Procédé et appareillage d'oxydation d'hydrocarbures |
| US3488740A (en) * | 1966-11-23 | 1970-01-06 | Halcon International Inc | Method for oxidizing hydrocarbons in the presence of boron adjuvants |
| US3535370A (en) * | 1967-08-03 | 1970-10-20 | Merck & Co Inc | ((2-(halomethyl)alkanoyl)phenoxy)alkanoic acids |
| US3622647A (en) * | 1969-09-11 | 1971-11-23 | Texaco Inc | Manufacture of alkene from alkane via boron esters |
Family Cites Families (2)
| 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 |
| US3109864A (en) * | 1961-09-26 | 1963-11-05 | Halcon International Inc | Oxidation of hydrocarbons |
-
1964
- 1964-01-17 US US338364A patent/US3317581A/en not_active Expired - Lifetime
-
1965
- 1965-01-08 NL NL656500235A patent/NL142663B/nl unknown
- 1965-01-12 GB GB1319/65A patent/GB1097485A/en not_active Expired
- 1965-01-12 GB GB34088/67A patent/GB1097486A/en not_active Expired
- 1965-01-14 BE BE658308D patent/BE658308A/xx unknown
- 1965-01-15 FR FR2023A patent/FR1424052A/fr not_active Expired
- 1965-01-15 LU LU47790D patent/LU47790A1/xx unknown
- 1965-01-15 CH CH58965A patent/CH437241A/fr unknown
- 1965-01-16 NO NO156396A patent/NO116671B/no unknown
- 1965-01-16 ES ES0308212A patent/ES308212A1/es not_active Expired
- 1965-01-17 IL IL22790A patent/IL22790A/en unknown
- 1965-01-18 DE DE1965H0054889 patent/DE1518969B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| LU47790A1 (nl) | 1966-07-15 |
| US3317581A (en) | 1967-05-02 |
| NL142663B (nl) | 1974-07-15 |
| NL6500235A (nl) | 1965-07-19 |
| CH437241A (fr) | 1967-06-15 |
| BE658308A (nl) | 1965-07-14 |
| GB1097485A (en) | 1968-01-03 |
| IL22790A (en) | 1968-06-20 |
| ES308212A1 (es) | 1965-05-01 |
| GB1097486A (en) | 1968-01-03 |
| DE1518969A1 (de) | 1969-09-11 |
| DE1518969B2 (de) | 1976-12-30 |
| FR1424052A (fr) | 1966-01-07 |
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