DE3135040A1 - Verfahren zur herstellung von tertiaer-alkyl-hypohalogeniten - Google Patents
Verfahren zur herstellung von tertiaer-alkyl-hypohalogenitenInfo
- Publication number
- DE3135040A1 DE3135040A1 DE19813135040 DE3135040A DE3135040A1 DE 3135040 A1 DE3135040 A1 DE 3135040A1 DE 19813135040 DE19813135040 DE 19813135040 DE 3135040 A DE3135040 A DE 3135040A DE 3135040 A1 DE3135040 A1 DE 3135040A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- alkanol
- reaction
- chlorine
- base
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000000460 chlorine Substances 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 14
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 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
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 28
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- -1 Alkyl hypochlorites Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NGMZATOLCPDHHH-UHFFFAOYSA-N 2-methylbutan-2-yl hypochlorite Chemical compound CCC(C)(C)OCl NGMZATOLCPDHHH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009826 distribution Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000007127 saponification reaction 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
- 238000004804 winding 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 (1)
| Publication Number | Publication Date |
|---|---|
| DE3135040A1 true DE3135040A1 (de) | 1982-04-08 |
Family
ID=22680575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813135040 Withdrawn DE3135040A1 (de) | 1980-09-08 | 1981-09-04 | Verfahren zur herstellung von tertiaer-alkyl-hypohalogeniten |
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 (3)
| 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 | ||
| US4008133A (en) * | 1974-09-20 | 1977-02-15 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
Family Cites Families (1)
| 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 |
-
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 GB GB8126994A patent/GB2083473B/en not_active Expired
- 1981-09-07 JP JP56140815A patent/JPS6030662B2/ja not_active Expired
- 1981-09-07 NL NL8104132A patent/NL8104132A/nl not_active Application Discontinuation
Patent Citations (3)
| 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 | ||
| US4008133A (en) * | 1974-09-20 | 1977-02-15 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2489818A1 (fr) | 1982-03-12 |
| JPS6030662B2 (ja) | 1985-07-17 |
| JPS5791956A (en) | 1982-06-08 |
| GB2083473B (en) | 1984-07-25 |
| NL8104132A (nl) | 1982-04-01 |
| US4342703A (en) | 1982-08-03 |
| GB2083473A (en) | 1982-03-24 |
| FR2489818B1 (enExample) | 1984-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8136 | Disposal/non-payment of the fee for publication/grant |