GB387325A - New organic compounds and methods of making the same - Google Patents
New organic compounds and methods of making the sameInfo
- Publication number
- GB387325A GB387325A GB21159/31A GB2115931A GB387325A GB 387325 A GB387325 A GB 387325A GB 21159/31 A GB21159/31 A GB 21159/31A GB 2115931 A GB2115931 A GB 2115931A GB 387325 A GB387325 A GB 387325A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butadiene
- monovinylacetylene
- reaction
- chloro
- chloride
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 6
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 235000019270 ammonium chloride Nutrition 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 abstract 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 abstract 1
- 229940045803 cuprous chloride Drugs 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 abstract 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 1
- 229940079877 pyrogallol Drugs 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
Classifications
-
- 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
- C07C21/19—Halogenated dienes
- C07C21/20—Halogenated butadienes
- C07C21/21—Chloroprene
-
- 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
-
- 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
- C07C21/19—Halogenated dienes
- C07C21/20—Halogenated butadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Halogenated butadienes and butenes are obtained by addition of hydrogen halide to monovinylacetylene. The reaction may be effected in the presence of a catalyst comprising a halide or a compound which will form a halide under the reaction conditions; specified catalysts are mercuric, mercurous, magnesium, calcium, auric and cuprous chlorides and ammonium chloride and bromide and their substitution products, e.g. pyridinium chloride and methylammonium chloride. In the examples, (1) monovinylacetylene and concentrated hydrochloric acid are shaken together in the cold in the presence of cuprous chloride and ammonium chloride, giving chloro-2-butadiene-1 : 3 and dichloro-2 : 4-butene-2; the products may be separated by distillation after addition of a little trinitrobenzene or iodine or an anti-oxidant, e.g. hydroquinone, catechol, pyrogallol, diphenylguanidine, or m-toluylenediamine; details of the distillation process are given; the reaction may also be effected continuously by passing gaseous monovinylacetylene into hydrochloric acid containing a catalyst as specified above, and withdrawing the reaction product from the surface of the liquid phase; the reaction may also be effected in ethereal solution; if the catalyst is omitted, or if one of the less effective catalysts is used, the products include chloro-4-butadiene-1 : 2; thus (example 2) monovinylacetylene and concentrated hydrochloric acid, shaken together in the presence of calcium chloride, yield chloro-4-butadiene-1 : 2 as well as chloro-2-butadiene-1 : 3; (3) monovinylacetylene and concentrated hydrobromic acid are shaken together in the presence of cuprous bromide, giving bromo-2-butadiene-1 : 3 and dibromo-2 : 4-butene-2. Bromo-4-butadiene-1 : 2 may be prepared analogously to chloro-4-butadiene-1 : 2. Specifications 384,654, 387,340, and 387,363 are referred to. The Specification as open to inspection under Sect. 91 refers to reaction products of monovinylacetylene with hydrofluoric and hydriodic acids. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US387325XA | 1930-10-22 | 1930-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB387325A true GB387325A (en) | 1933-01-24 |
Family
ID=21901568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21159/31A Expired GB387325A (en) | 1930-10-22 | 1931-07-24 | New organic compounds and methods of making the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB387325A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427268A (en) * | 1965-12-06 | 1969-02-11 | Nat Starch Chem Corp | Non-phasing neoprene cement compositions |
| EP0826655A1 (en) * | 1996-08-28 | 1998-03-04 | Basf Aktiengesellschaft | Preparation of alkyl bromides from aqueous hydrobromic acid and olefins |
| US5955638A (en) * | 1997-09-24 | 1999-09-21 | Solvay (Societe Anonyme) | Process for preparation of 2-chloro-1-propene |
-
1931
- 1931-07-24 GB GB21159/31A patent/GB387325A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427268A (en) * | 1965-12-06 | 1969-02-11 | Nat Starch Chem Corp | Non-phasing neoprene cement compositions |
| EP0826655A1 (en) * | 1996-08-28 | 1998-03-04 | Basf Aktiengesellschaft | Preparation of alkyl bromides from aqueous hydrobromic acid and olefins |
| US5955638A (en) * | 1997-09-24 | 1999-09-21 | Solvay (Societe Anonyme) | Process for preparation of 2-chloro-1-propene |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB518325A (en) | A process for the production of unsaturated halogen-containing derivatives of propene | |
| GB428361A (en) | Improvements in methods of preparing fluorine derivatives of hydro-carbons | |
| US2344061A (en) | Preparation of 1-chloro-1-fluoro ethylene | |
| GB554499A (en) | Controlled hydrohalogenation of unsaturated organic compounds | |
| GB387325A (en) | New organic compounds and methods of making the same | |
| Ecke et al. | Some Reactions of t-Butylethylene1 | |
| US2243191A (en) | Production of olefins and diolefins | |
| Adam et al. | Stereospecific dehalogenation of vic-dibromides by sodium naphthalenide | |
| US2337912A (en) | Halogenation of nitro compounds | |
| GB600785A (en) | Process for the reaction of hydrogen halides with unsaturated compounds | |
| Linstrumelle et al. | Simple route to mono-, di-, and tri-substituted allenic compounds | |
| US2882323A (en) | Hydrochlorination of myrcene | |
| US2500385A (en) | Process for preparing norcamphor | |
| US2404538A (en) | Manufacture of arylalkene hydrocarbons | |
| GB965048A (en) | Tetrafluoro-dichloroisopropanol and its hydrate and the production thereof | |
| US2107515A (en) | Process for the production of hydrated olefines | |
| US2284467A (en) | Hydrohalogenation of unsaturated hydrocarbons | |
| US1637972A (en) | Process for the production of ethyl chloride | |
| Boozer et al. | Allylic Bromination by N-Bromo-t-butylamine1 | |
| GB798889A (en) | Allylic rearrangement of chlorine substituted butenes | |
| GB1218224A (en) | Vinyl chloride | |
| US2255605A (en) | Manufacture of 1-chloro, 3-bromo propane | |
| GB880029A (en) | Production of trans-1,4-dichlorobutene-2 | |
| SU487054A1 (en) | The method of producing trichlorobutenes | |
| US2051300A (en) | Process for the manufacture of alkyl phenols |