DE1271107B - Verfahren zur Herstellung eines aus 1, 2-Dichlorbuten-(2), 1, 3-Dichlorbuten-(2) und 2, 3-Dichlorbuten-(1) bestehenden Gemisches - Google Patents
Verfahren zur Herstellung eines aus 1, 2-Dichlorbuten-(2), 1, 3-Dichlorbuten-(2) und 2, 3-Dichlorbuten-(1) bestehenden GemischesInfo
- Publication number
- DE1271107B DE1271107B DEP1271A DE1271107A DE1271107B DE 1271107 B DE1271107 B DE 1271107B DE P1271 A DEP1271 A DE P1271A DE 1271107 A DE1271107 A DE 1271107A DE 1271107 B DE1271107 B DE 1271107B
- Authority
- DE
- Germany
- Prior art keywords
- dichlorobutene
- trichlorobutane
- tetrachlorobutane
- mixture
- chlorobutadiene
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title description 3
- RMZZAEDPBSKZOM-UHFFFAOYSA-N 1,2,3-trichlorobutane Chemical compound CC(Cl)C(Cl)CCl RMZZAEDPBSKZOM-UHFFFAOYSA-N 0.000 claims description 41
- WSPZFVOCHITLIY-UHFFFAOYSA-N 2,2,3,3-tetrachlorobutane Chemical compound CC(Cl)(Cl)C(C)(Cl)Cl WSPZFVOCHITLIY-UHFFFAOYSA-N 0.000 claims description 31
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- -1 1,2,3-trichlorobutane Phosphonium chlorides Chemical class 0.000 description 6
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000007033 dehydrochlorination reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GVNNGJMKAFLSHZ-NSCUHMNNSA-N (e)-1,3-dichlorobut-1-ene Chemical compound CC(Cl)\C=C\Cl GVNNGJMKAFLSHZ-NSCUHMNNSA-N 0.000 description 1
- ABSHBZODGOHLFR-UHFFFAOYSA-N 1,1,1-trichlorobutane Chemical class CCCC(Cl)(Cl)Cl ABSHBZODGOHLFR-UHFFFAOYSA-N 0.000 description 1
- UNTJXPFYXVCMFE-UHFFFAOYSA-N 2,2,3-trichlorobutane Chemical compound CC(Cl)C(C)(Cl)Cl UNTJXPFYXVCMFE-UHFFFAOYSA-N 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical group ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007038 hydrochlorination reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical group P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/392—Separation; Purification; Stabilisation; Use of additives by crystallisation; Purification or separation of the crystals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
- C07C21/073—Dichloro-alkenes
- C07C21/09—Dichloro-butenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK57687A DE1245360B (de) | 1965-11-17 | 1965-11-17 | Verfahren zur Herstellung eines aus 1,2-Dichlorbuten-(2), 1, 3-Dichlorbuten-(2) und 2 ,3-Dichlorbuten-(1) bestehenden Gemisches |
| DEK0063116 | 1967-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1271107B true DE1271107B (de) | 1968-06-27 |
Family
ID=7230927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1271A Pending DE1271107B (de) | 1965-11-17 | 1967-08-17 | Verfahren zur Herstellung eines aus 1, 2-Dichlorbuten-(2), 1, 3-Dichlorbuten-(2) und 2, 3-Dichlorbuten-(1) bestehenden Gemisches |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3585247A (en:Method) |
| AT (1) | AT279566B (en:Method) |
| BE (1) | BE719570A (en:Method) |
| DE (1) | DE1271107B (en:Method) |
| FR (1) | FR95527E (en:Method) |
| GB (1) | GB1204553A (en:Method) |
| NL (1) | NL6811609A (en:Method) |
-
1967
- 1967-08-17 DE DEP1271A patent/DE1271107B/de active Pending
-
1968
- 1968-07-30 US US748784A patent/US3585247A/en not_active Expired - Lifetime
- 1968-08-08 GB GB37849/68A patent/GB1204553A/en not_active Expired
- 1968-08-14 FR FR163109A patent/FR95527E/fr not_active Expired
- 1968-08-15 NL NL6811609A patent/NL6811609A/xx unknown
- 1968-08-16 BE BE719570D patent/BE719570A/xx unknown
- 1968-08-16 AT AT803068A patent/AT279566B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE719570A (en:Method) | 1969-02-17 |
| GB1204553A (en) | 1970-09-09 |
| US3585247A (en) | 1971-06-15 |
| FR95527E (fr) | 1971-01-22 |
| NL6811609A (en:Method) | 1969-02-19 |
| AT279566B (de) | 1970-03-10 |
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