FR2489818A1 - Procede de production d'hypohalogenite d'alcoyle tertiaire - Google Patents
Procede de production d'hypohalogenite d'alcoyle tertiaire Download PDFInfo
- Publication number
- FR2489818A1 FR2489818A1 FR8116828A FR8116828A FR2489818A1 FR 2489818 A1 FR2489818 A1 FR 2489818A1 FR 8116828 A FR8116828 A FR 8116828A FR 8116828 A FR8116828 A FR 8116828A FR 2489818 A1 FR2489818 A1 FR 2489818A1
- Authority
- FR
- France
- Prior art keywords
- tertiary
- reaction
- alkanol
- chlorine
- process according
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000000460 chlorine Substances 0.000 claims abstract description 26
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 24
- GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical group CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 150000007529 inorganic bases Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000003134 recirculating effect Effects 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 19
- 239000000126 substance Substances 0.000 abstract description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
- 101001076841 Solanum lycopersicum Ribulose bisphosphate carboxylase small subunit, chloroplastic 2 Proteins 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000001336 alkenes Chemical class 0.000 description 8
- -1 alkyl hypochlorites Chemical group 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FIKOOQXJBAJJSE-YTQTXRHFSA-N Alectrol Chemical compound O1C(=O)C(C)=C[C@@H]1O\C=C/1C(=O)O[C@@H]2C3(O)C(C)(C)CCCC3=C[C@@H]2\1 FIKOOQXJBAJJSE-YTQTXRHFSA-N 0.000 description 1
- FIKOOQXJBAJJSE-FYTPEDKISA-N Alectrol Natural products O(/C=C/1\C(=O)O[C@@H]2[C@]3(O)C(C)(C)CCCC3=C[C@H]\12)[C@@H]1OC(=O)C(C)=C1 FIKOOQXJBAJJSE-FYTPEDKISA-N 0.000 description 1
- CJFSBMYURKOBMY-UHFFFAOYSA-N Cl(=O)OCCCCC Chemical group Cl(=O)OCCCCC CJFSBMYURKOBMY-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- RMMFHMJFKSYQCQ-UHFFFAOYSA-N butyl chlorite Chemical group CCCCOCl=O RMMFHMJFKSYQCQ-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- DLRIUVHQJRZTMZ-UKTHLTGXSA-N orobanchyl acetate Natural products CC(=O)OC1C2C(OC(=O)/C/2=C/OC3OC(=O)C(=C3)C)C4=C1CCCC4(C)C DLRIUVHQJRZTMZ-UKTHLTGXSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C71/00—Esters of oxyacids of halogens
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/185,337 US4342703A (en) | 1980-09-08 | 1980-09-08 | Production of alkyl hypohalites |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2489818A1 true FR2489818A1 (fr) | 1982-03-12 |
| FR2489818B1 FR2489818B1 (enExample) | 1984-10-26 |
Family
ID=22680575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8116828A Granted FR2489818A1 (fr) | 1980-09-08 | 1981-09-04 | Procede de production d'hypohalogenite d'alcoyle tertiaire |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4342703A (enExample) |
| JP (1) | JPS6030662B2 (enExample) |
| DE (1) | DE3135040A1 (enExample) |
| FR (1) | FR2489818A1 (enExample) |
| GB (1) | GB2083473B (enExample) |
| NL (1) | NL8104132A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8200023A (nl) * | 1981-01-30 | 1982-08-16 | Lummus Co | Werkwijze ter bereiding van tert. alkylhypohalogenieten. |
| RU2446146C2 (ru) * | 2010-04-27 | 2012-03-27 | Открытое акционерное общество "Сибур-Нефтехим" | Способ получения трет-бутилгипохлорита |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1938175A (en) * | 1933-12-05 | Manufacture of alkyl hypohalites | ||
| US3149140A (en) * | 1964-09-15 | Process for preparing tertiary |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957442A (en) * | 1968-10-23 | 1976-05-18 | Asahi Denka Kogyo Kabushiki Kaisha | Apparatus for the production of glycerol dichlorohydrin |
| US4008133A (en) * | 1974-09-20 | 1977-02-15 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
-
1980
- 1980-09-08 US US06/185,337 patent/US4342703A/en not_active Expired - Lifetime
-
1981
- 1981-09-04 DE DE19813135040 patent/DE3135040A1/de not_active Withdrawn
- 1981-09-04 FR FR8116828A patent/FR2489818A1/fr active Granted
- 1981-09-07 JP JP56140815A patent/JPS6030662B2/ja not_active Expired
- 1981-09-07 GB GB8126994A patent/GB2083473B/en not_active Expired
- 1981-09-07 NL NL8104132A patent/NL8104132A/nl not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1938175A (en) * | 1933-12-05 | Manufacture of alkyl hypohalites | ||
| US3149140A (en) * | 1964-09-15 | Process for preparing tertiary |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5791956A (en) | 1982-06-08 |
| GB2083473B (en) | 1984-07-25 |
| NL8104132A (nl) | 1982-04-01 |
| DE3135040A1 (de) | 1982-04-08 |
| GB2083473A (en) | 1982-03-24 |
| US4342703A (en) | 1982-08-03 |
| FR2489818B1 (enExample) | 1984-10-26 |
| JPS6030662B2 (ja) | 1985-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |