DE846692C - Verfahren zur Herstellung organischer Bromverbindungen - Google Patents
Verfahren zur Herstellung organischer BromverbindungenInfo
- Publication number
- DE846692C DE846692C DEN1928A DEN0001928A DE846692C DE 846692 C DE846692 C DE 846692C DE N1928 A DEN1928 A DE N1928A DE N0001928 A DEN0001928 A DE N0001928A DE 846692 C DE846692 C DE 846692C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen bromide
- reaction
- compounds
- bromine compounds
- mixture
- 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 17
- 150000005526 organic bromine compounds Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 32
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- -1 methane hydrocarbons Chemical class 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000010471 Markovnikov's rule Methods 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/087—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy
- B01J19/088—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy giving rise to electric discharges
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL149038A NL76888C (en, 2012) | 1949-09-30 | 1949-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE846692C true DE846692C (de) | 1952-08-14 |
Family
ID=19798820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN1928A Expired DE846692C (de) | 1949-09-30 | 1950-09-20 | Verfahren zur Herstellung organischer Bromverbindungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2672439A (en, 2012) |
| DE (1) | DE846692C (en, 2012) |
| FR (1) | FR1025280A (en, 2012) |
| GB (1) | GB668159A (en, 2012) |
| NL (1) | NL76888C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134362B (de) * | 1958-04-09 | 1962-08-09 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von ªÏ-Bromalkanen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773672A (en) * | 1997-06-02 | 1998-06-30 | Albemarle Corporation | Production of 1-bromopropane |
| MY150469A (en) * | 2005-04-18 | 2014-01-30 | Albemarle Corp | Processes for production and purification of normal propyl bromide |
| EP2024314B1 (en) * | 2006-06-02 | 2011-08-10 | Albemarle Corporation | Separation and/or recovery of propyl bromide |
| KR20090045299A (ko) * | 2006-08-30 | 2009-05-07 | 알베마를 코포레이션 | 프로필 브로마이드 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1012149A (en) * | 1911-04-03 | 1911-12-19 | Ignac Pfeifer | Process for the production of halogen derivatives of hydrocarbons. |
| US1710155A (en) * | 1922-07-20 | 1929-04-23 | Universal Oil Prod Co | Process and apparatus for forming oxidation products of hydrocarbon oils |
| NL67369C (en, 2012) * | 1940-10-30 | |||
| US2376675A (en) * | 1942-02-23 | 1945-05-22 | Shell Dev | Process for catalyzed abnormal addition reactions |
| US2398481A (en) * | 1942-02-23 | 1946-04-16 | Shell Dev | Process for catalyzed abnormal addition reactions |
-
1949
- 1949-09-30 NL NL149038A patent/NL76888C/xx active
-
1950
- 1950-09-20 DE DEN1928A patent/DE846692C/de not_active Expired
- 1950-09-22 US US186302A patent/US2672439A/en not_active Expired - Lifetime
- 1950-09-28 GB GB23812/50A patent/GB668159A/en not_active Expired
- 1950-09-29 FR FR1025280D patent/FR1025280A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134362B (de) * | 1958-04-09 | 1962-08-09 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von ªÏ-Bromalkanen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL76888C (en, 2012) | 1954-08-16 |
| GB668159A (en) | 1952-03-12 |
| US2672439A (en) | 1954-03-16 |
| FR1025280A (fr) | 1953-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1107665B (de) | Verfahren zur Herstellung von olefinfreien reinen Aluminiumtrialkylen | |
| DE846692C (de) | Verfahren zur Herstellung organischer Bromverbindungen | |
| DE1198346B (de) | Verfahren zur Herstellung von alpha-Olefinen | |
| DE1086226B (de) | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) | |
| DE875356C (de) | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Hydroperoxyden | |
| EP0025940B1 (de) | Verfahren zur Hydroxylierung olefinisch ungesättigter Verbindungen | |
| DE844442C (de) | Verfahren zur Herstellung von 1, 1-Dihalogen-1, 3-alkadienen | |
| EP0010236A1 (de) | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-butandiol | |
| DE848353C (de) | Verfahren zur Herstellung organischer Chlorverbindungen | |
| DE3431131A1 (de) | Verfahren zur herstellung von jononen | |
| DE824051C (de) | Verfahren zur Herstellung von Umwandlungsprodukten aus ungesaettigten organischen Verbindungen und Stickoxydul (NO) | |
| DE2409920C3 (de) | Verfahren zur Herstellung von Cyclopentadienen durch thermische Spaltung von Dicyclopentadienen in der Gasphase | |
| DE906450C (de) | Verfahren zur Durchfuehrung von Additionsreaktionen zwischen Alkenen einerseits und Wasser oder Chlorwasserstoff andererseits | |
| DE1443794C3 (en, 2012) | ||
| DE2134016A1 (de) | Verfahren zur herstellung von wasserfreiem 1,4-dioxan | |
| DE2405251A1 (de) | Verfahren zur entfaerbung von carbonylverbindungen | |
| EP0564979B1 (de) | Verfahren zur Herstellung von Dixylylpropan | |
| DE886910C (de) | Verfahren zur Herstellung von Dimeren aus Monohalogenolefinen von der Art des Isobutenylchlorids | |
| DE696724C (de) | Verfahren zur Herstellung von Hydrinden und ª‡- und ª‰-Truxen | |
| DE2337158C2 (de) | Verfahren zur Herstellung von Alkancarbonsäuren | |
| DE1247286B (de) | Verfahren zur Alkylierung von Cumol bzw. Benzol mit Propen ueber Aluminiumchlorid | |
| DE1518677C (en, 2012) | ||
| AT229025B (de) | Verfahren zur Herstellung von Katalysatoren für die Polymerisation von Olefinen | |
| DE2921080A1 (de) | Verfahren zur herstellung von diarylaethanderivaten | |
| DE1157598B (de) | Verfahren zur Herstellung von N-substituierten Carbaminsaeureestern |