DE2435029C2 - Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuel - Google Patents
Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuelInfo
- Publication number
- DE2435029C2 DE2435029C2 DE19742435029 DE2435029A DE2435029C2 DE 2435029 C2 DE2435029 C2 DE 2435029C2 DE 19742435029 DE19742435029 DE 19742435029 DE 2435029 A DE2435029 A DE 2435029A DE 2435029 C2 DE2435029 C2 DE 2435029C2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- hydrogen chloride
- monochloroalkanes
- alcohol
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- 235000005074 zinc chloride Nutrition 0.000 claims description 9
- 239000011592 zinc chloride Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 14
- 238000006243 chemical reaction Methods 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 150000001298 alcohols Chemical class 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 238000010924 continuous production Methods 0.000 claims 3
- 150000001924 cycloalkanes Chemical class 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- -1 alkanes alkanes Chemical class 0.000 claims 2
- 150000001348 alkyl chlorides Chemical class 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 241000272517 Anseriformes Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 229910000365 copper sulfate Inorganic materials 0.000 claims 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000003578 releasing effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742435029 DE2435029C2 (de) | 1974-07-20 | 1974-07-20 | Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuel |
| FR7520638A FR2278663A1 (fr) | 1974-07-20 | 1975-07-01 | Procede de production continue d'alcanes et cycloalcanes monochlores a plus de quatre atomes de carbone par molecule |
| GB2950775A GB1457710A (en) | 1974-07-20 | 1975-07-14 | Process for the continuous production of monochloroalkanes and monochlorocycloalkanes |
| US05/596,330 US4073816A (en) | 1974-07-20 | 1975-07-16 | Process for the continuous production of monochloroalkanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742435029 DE2435029C2 (de) | 1974-07-20 | 1974-07-20 | Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2435029B1 DE2435029B1 (de) | 1976-01-29 |
| DE2435029C2 true DE2435029C2 (de) | 1976-09-29 |
Family
ID=5921108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742435029 Expired DE2435029C2 (de) | 1974-07-20 | 1974-07-20 | Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuel |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4073816A (enExample) |
| DE (1) | DE2435029C2 (enExample) |
| FR (1) | FR2278663A1 (enExample) |
| GB (1) | GB1457710A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4935565A (en) * | 1988-08-24 | 1990-06-19 | The Dow Chemical Company | Process and catalyst for hydrochlorination of hydrocarbons |
| US5041406A (en) * | 1988-08-24 | 1991-08-20 | The Dow Chemical Company | Catalyst for hydrochlorination of hydrocarbons |
| DE3917190A1 (de) * | 1989-05-26 | 1990-11-29 | Henkel Kgaa | Verfahren zur herstellung von 1-chloralkanen bzw. -alkenen |
| FR2720740B1 (fr) * | 1994-06-06 | 1996-07-19 | Atochem Elf Sa | Procédé d'alcoolyse du tétrachlorure de carbone. |
| DE19604567A1 (de) | 1996-02-08 | 1997-11-06 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Alkylchloriden |
| US5856597A (en) * | 1997-04-25 | 1999-01-05 | Albemarle Corporation | Preparation of lucas reagent of enhanced utility and its use in synthesis of cycloaliphatic chlorides |
| JP2013544765A (ja) | 2010-09-23 | 2013-12-19 | アイシーエル−アイピー アメリカ インコーポレイテッド | ポリヒドロキシホスホネートを実質的に含まないモノヒドロキシ環状ホスホネート、その製造方法およびそれより得られる難燃性軟質ポリウレタンフォーム |
| WO2023245633A1 (zh) * | 2022-06-24 | 2023-12-28 | 安徽金禾实业股份有限公司 | 一种生产氯乙烷的工艺 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA691295A (en) * | 1964-07-21 | O. Wikman Andrew | Manufacture of methyl chloride | |
| US1983542A (en) * | 1932-07-27 | 1934-12-11 | Du Pont | Preparation of alkyl halides |
| DE671086C (de) * | 1933-02-15 | 1939-01-31 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Chlormethyl |
| US2124605A (en) * | 1934-06-12 | 1938-07-26 | Du Pont | Alkyl chlorides |
| US2396639A (en) * | 1943-06-23 | 1946-03-19 | Hercules Powder Co Ltd | Preparation of ethyl chloride |
| US2622107A (en) * | 1950-10-28 | 1952-12-16 | Ethyl Corp | Manufacture of alkyl chlorides |
| US2847484A (en) * | 1957-03-01 | 1958-08-12 | Leon A Kolker | Preparation of methyl chloride |
| US3502733A (en) * | 1967-11-08 | 1970-03-24 | Allied Chem | Production of chloromethanes |
-
1974
- 1974-07-20 DE DE19742435029 patent/DE2435029C2/de not_active Expired
-
1975
- 1975-07-01 FR FR7520638A patent/FR2278663A1/fr active Granted
- 1975-07-14 GB GB2950775A patent/GB1457710A/en not_active Expired
- 1975-07-16 US US05/596,330 patent/US4073816A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4073816A (en) | 1978-02-14 |
| GB1457710A (en) | 1976-12-08 |
| DE2435029B1 (de) | 1976-01-29 |
| FR2278663A1 (fr) | 1976-02-13 |
| FR2278663B3 (enExample) | 1979-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |