CA1144559A - Procede de stabilisation des solutions de derives organiques du chrome hexavalent dans les solvants hydrocarbones par les esters phosphoriques - Google Patents
Procede de stabilisation des solutions de derives organiques du chrome hexavalent dans les solvants hydrocarbones par les esters phosphoriquesInfo
- Publication number
- CA1144559A CA1144559A CA000357037A CA357037A CA1144559A CA 1144559 A CA1144559 A CA 1144559A CA 000357037 A CA000357037 A CA 000357037A CA 357037 A CA357037 A CA 357037A CA 1144559 A CA1144559 A CA 1144559A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- section
- phosphoric
- rolls
- chromium
- 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
- 150000002148 esters Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 17
- 229930195733 hydrocarbon Natural products 0.000 title claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 8
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 title claims description 6
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- -1 chromate tertiary alcohol Chemical class 0.000 claims description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- 239000011651 chromium Substances 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001924 cycloalkanes Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005452 bending Methods 0.000 abstract 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000005096 rolling process Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- 235000021317 phosphate Nutrition 0.000 description 13
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 9
- 150000001844 chromium Chemical class 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229940048084 pyrophosphate Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BCEIUDAMUFAQMG-UHFFFAOYSA-M CC(C)(C)O[Cr](O)(=O)=O Chemical compound CC(C)(C)O[Cr](O)(=O)=O BCEIUDAMUFAQMG-UHFFFAOYSA-M 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- BUCJHJXFXUZJHL-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound CCC1(O)CCCCC1 BUCJHJXFXUZJHL-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 description 1
- FMPFPPIRHUYHKY-UHFFFAOYSA-N 2-methylheptadecan-2-ol Chemical compound CCCCCCCCCCCCCCCC(C)(C)O FMPFPPIRHUYHKY-UHFFFAOYSA-N 0.000 description 1
- SVBLDLLXNRGMBG-UHFFFAOYSA-N 2-methylpropyl dihydrogen phosphate Chemical compound CC(C)COP(O)(O)=O SVBLDLLXNRGMBG-UHFFFAOYSA-N 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- RUZMUTWCUZLWQU-UHFFFAOYSA-N [ethoxy(hydroxy)phosphoryl] ethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OP(O)(=O)OCC RUZMUTWCUZLWQU-UHFFFAOYSA-N 0.000 description 1
- BPNLLIHZSAFABG-UHFFFAOYSA-N [hydroxy(methoxy)phosphoryl] methyl hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(=O)OC BPNLLIHZSAFABG-UHFFFAOYSA-N 0.000 description 1
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YTFJQDNGSQJFNA-UHFFFAOYSA-N benzyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- AKAUCGJQKLOHHK-UHFFFAOYSA-N cyclohexyl dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCCCC1 AKAUCGJQKLOHHK-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- WBJBEMDHFMUSAY-UHFFFAOYSA-N dibutyl phosphono phosphate Chemical compound CCCCOP(=O)(OP(O)(O)=O)OCCCC WBJBEMDHFMUSAY-UHFFFAOYSA-N 0.000 description 1
- AWGWBIUCLGCTRJ-UHFFFAOYSA-L dihydroxy(dioxo)chromium;2-methylheptadecan-2-ol Chemical compound O[Cr](O)(=O)=O.CCCCCCCCCCCCCCCC(C)(C)O AWGWBIUCLGCTRJ-UHFFFAOYSA-L 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- QWGFJBVCQAKNFA-UHFFFAOYSA-N hexyl phosphono hydrogen phosphate Chemical compound CCCCCCOP(O)(=O)OP(O)(O)=O QWGFJBVCQAKNFA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B21—MECHANICAL METAL-WORKING WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
- B21D—WORKING OR PROCESSING OF SHEET METAL OR METAL TUBES, RODS OR PROFILES WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
- B21D53/00—Making other particular articles
- B21D53/16—Making other particular articles rings, e.g. barrel hoops
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Bending Of Plates, Rods, And Pipes (AREA)
- Reduction Rolling/Reduction Stand/Operation Of Reduction Machine (AREA)
- Forging (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7900738A FR2446140A1 (fr) | 1979-01-12 | 1979-01-12 | Procede et dispositif de fabrication de cornieres cintrees |
| FR79/19/738 | 1979-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1144559A true CA1144559A (fr) | 1983-04-12 |
Family
ID=9220680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000357037A Expired CA1144559A (fr) | 1979-01-12 | 1980-07-25 | Procede de stabilisation des solutions de derives organiques du chrome hexavalent dans les solvants hydrocarbones par les esters phosphoriques |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0013653B1 (enExample) |
| AT (1) | ATE11646T1 (enExample) |
| CA (1) | CA1144559A (enExample) |
| DE (1) | DE3070089D1 (enExample) |
| FR (1) | FR2446140A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3529152C2 (de) * | 1984-10-03 | 1986-11-20 | Dieter Dipl.-Ing. 6242 Kronberg Kunz | Vorrichtung zur Herstellung eines Winkelringes |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191511692A (en) * | 1915-08-13 | 1916-08-14 | William Scott | An Improved Machine for Bending Angle-iron, or Tee-iron Bars into Hoops, Rings or the like. |
| FR910403A (fr) * | 1944-11-21 | 1946-06-06 | Sncase | Machine à cintrer les profilés dont l'épaisseur est faible relativement à l'étendue des sections |
| DE952143C (de) * | 1954-09-16 | 1956-11-08 | Schwermaschb Heinrich Rau Veb | Verfahren und Vorrichtung zum Regeln des Walzdruckes beim Hochkantbiegen von Flach- und Profilstahl |
| US2948322A (en) * | 1956-05-23 | 1960-08-09 | Quadriga Mfg Company | Apparatus for forming an oil seal inner shell |
| US2922324A (en) * | 1956-11-07 | 1960-01-26 | Anemostat Corp America | Machine for curving strip material |
| US3138191A (en) * | 1961-03-06 | 1964-06-23 | Kolk Mfg Co Inc | Metal rolling machine |
| DE1452558A1 (de) * | 1962-04-10 | 1969-04-03 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von Ringen aus Bandeisen |
| JPS4946467B1 (enExample) * | 1970-07-16 | 1974-12-10 | ||
| US3746238A (en) * | 1971-10-05 | 1973-07-17 | Thornton F C Co | Welding and cutting apparatus |
| FR2329370A1 (fr) * | 1975-10-31 | 1977-05-27 | Coil Protection Service | Procede et appareillage pour realiser des cornieres de faible epaisseur et de forme cintree |
-
1979
- 1979-01-12 FR FR7900738A patent/FR2446140A1/fr active Granted
-
1980
- 1980-01-14 DE DE8080400046T patent/DE3070089D1/de not_active Expired
- 1980-01-14 AT AT80400046T patent/ATE11646T1/de not_active IP Right Cessation
- 1980-01-14 EP EP80400046A patent/EP0013653B1/fr not_active Expired
- 1980-07-25 CA CA000357037A patent/CA1144559A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATE11646T1 (de) | 1985-02-15 |
| DE3070089D1 (en) | 1985-03-21 |
| EP0013653A1 (fr) | 1980-07-23 |
| FR2446140B1 (enExample) | 1983-11-04 |
| FR2446140A1 (fr) | 1980-08-08 |
| EP0013653B1 (fr) | 1985-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |