DE2352850A1 - Verfahren zur herstellung von chloropren - Google Patents
Verfahren zur herstellung von chloroprenInfo
- Publication number
- DE2352850A1 DE2352850A1 DE19732352850 DE2352850A DE2352850A1 DE 2352850 A1 DE2352850 A1 DE 2352850A1 DE 19732352850 DE19732352850 DE 19732352850 DE 2352850 A DE2352850 A DE 2352850A DE 2352850 A1 DE2352850 A1 DE 2352850A1
- Authority
- DE
- Germany
- Prior art keywords
- alkoxide
- alcohol
- dehydrochlorination
- carried out
- chloroprene
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 20
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 8
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical class CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- -1 tert-butyl catechol Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4935072A GB1440567A (en) | 1972-10-26 | 1972-10-26 | Process for the production of chloroprene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2352850A1 true DE2352850A1 (de) | 1974-05-09 |
Family
ID=10452073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732352850 Withdrawn DE2352850A1 (de) | 1972-10-26 | 1973-10-22 | Verfahren zur herstellung von chloropren |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3896181A (enExample) |
| JP (1) | JPS5128605B2 (enExample) |
| BE (1) | BE806470A (enExample) |
| CA (1) | CA1005076A (enExample) |
| DE (1) | DE2352850A1 (enExample) |
| FR (1) | FR2204599B1 (enExample) |
| GB (1) | GB1440567A (enExample) |
| IT (1) | IT1006621B (enExample) |
| NL (1) | NL7313852A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2533429C3 (de) * | 1975-07-25 | 1979-07-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Chlorbutadien-U3) |
| JPS55162724A (en) * | 1979-06-04 | 1980-12-18 | Denki Kagaku Kogyo Kk | Preparation of chloroprene |
| US4423262A (en) * | 1980-03-13 | 1983-12-27 | Ethyl Corporation | Preparation of dibromostyrene |
| US4686311A (en) * | 1980-03-13 | 1987-08-11 | Ethyl Corporation | Dehydrohalogenation of haloethyl brominated benzenes |
| DE3208796A1 (de) * | 1982-03-11 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,3-dichlorbutadien- (1,3) |
| FI902898A0 (fi) * | 1988-10-13 | 1990-06-11 | Sig Schweiz Industrieges | Lutningskompensator foer snabbgaoende fordon, saerskilt raelsfordon. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2180115A (en) * | 1936-03-28 | 1939-11-14 | Ig Farbenindustrie Ag | Process of preparing beta-halogenbutadienes-1,3 |
| US2542976A (en) * | 1946-10-31 | 1951-02-27 | Shell Dev | Process for the production of alkynes |
| NL103651C (enExample) * | 1957-11-28 | |||
| US3060245A (en) * | 1961-01-03 | 1962-10-23 | Monsanto Chemicals | Polymerization inhibitor |
-
1972
- 1972-10-26 GB GB4935072A patent/GB1440567A/en not_active Expired
-
1973
- 1973-10-09 NL NL7313852A patent/NL7313852A/xx not_active Application Discontinuation
- 1973-10-11 US US405324A patent/US3896181A/en not_active Expired - Lifetime
- 1973-10-18 IT IT30274/73A patent/IT1006621B/it active
- 1973-10-22 DE DE19732352850 patent/DE2352850A1/de not_active Withdrawn
- 1973-10-24 BE BE137029A patent/BE806470A/xx unknown
- 1973-10-25 JP JP48120337A patent/JPS5128605B2/ja not_active Expired
- 1973-10-25 FR FR7338016A patent/FR2204599B1/fr not_active Expired
- 1973-10-26 CA CA184,328A patent/CA1005076A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE806470A (fr) | 1974-04-24 |
| JPS5128605B2 (enExample) | 1976-08-20 |
| FR2204599A1 (enExample) | 1974-05-24 |
| US3896181A (en) | 1975-07-22 |
| JPS5012005A (enExample) | 1975-02-07 |
| IT1006621B (it) | 1976-10-20 |
| NL7313852A (enExample) | 1974-05-01 |
| FR2204599B1 (enExample) | 1978-09-15 |
| GB1440567A (en) | 1976-06-23 |
| CA1005076A (en) | 1977-02-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |