SU1240350A3 - Способ получени этиленовых @ -галогенацеталей - Google Patents
Способ получени этиленовых @ -галогенацеталей Download PDFInfo
- Publication number
- SU1240350A3 SU1240350A3 SU823523097A SU3523097A SU1240350A3 SU 1240350 A3 SU1240350 A3 SU 1240350A3 SU 823523097 A SU823523097 A SU 823523097A SU 3523097 A SU3523097 A SU 3523097A SU 1240350 A3 SU1240350 A3 SU 1240350A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- chlorine
- carbon atoms
- gamma
- halogenacetals
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 3
- 239000005977 Ethylene Substances 0.000 title claims description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- VEEFADFWCHSFIU-UHFFFAOYSA-N 3-methylbut-3-enal Chemical compound CC(=C)CC=O VEEFADFWCHSFIU-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims 2
- 238000005658 halogenation reaction Methods 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003511 tertiary amides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 -halo acetals Chemical class 0.000 description 2
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- MVQDNWRPFWUJRQ-UHFFFAOYSA-N 1-methoxy-3-methylbut-2-ene Chemical compound COCC=C(C)C MVQDNWRPFWUJRQ-UHFFFAOYSA-N 0.000 description 1
- QIACXWLIFNNZDL-UHFFFAOYSA-N 4,4-diethoxy-2-methylbut-1-ene Chemical compound CCOC(CC(C)=C)OCC QIACXWLIFNNZDL-UHFFFAOYSA-N 0.000 description 1
- CYCYEISIQAEGOF-UHFFFAOYSA-N 4-chloro-3-methylbut-2-enal Chemical compound ClCC(C)=CC=O CYCYEISIQAEGOF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ACWQBUSCFPJUPN-UHFFFAOYSA-N Tiglaldehyde Natural products CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 description 1
- KRROLIZNADPOLD-SNAWJCMRSA-N [(1e)-3-methylbuta-1,3-dienyl] acetate Chemical compound CC(=O)O\C=C\C(C)=C KRROLIZNADPOLD-SNAWJCMRSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8123685A FR2518534A1 (fr) | 1981-12-18 | 1981-12-18 | Procede de preparation d'halogenoacetals ethyleniques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1240350A3 true SU1240350A3 (ru) | 1986-06-23 |
Family
ID=9265169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823523097A SU1240350A3 (ru) | 1981-12-18 | 1982-12-17 | Способ получени этиленовых @ -галогенацеталей |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4503239A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0082782B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS58110532A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE12220T1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1184208A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3262724D1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2518534A1 (cg-RX-API-DMAC10.html) |
| SU (1) | SU1240350A3 (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2555162B1 (fr) * | 1983-11-18 | 1986-09-26 | Rhone Poulenc Sante | Procede de preparation de derives ethyleniques chlores |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA625178A (en) * | 1961-08-08 | Union Carbide And Carbon Corporation | Process for the production of 2-chloroacrolein and derivatives thereof | |
| US3160636A (en) * | 1961-10-12 | 1964-12-08 | Universal Oil Prod Co | Halocycloalkenic derivatives of haloalkenyl dioxanes |
| FR1371230A (fr) * | 1963-05-31 | 1964-09-04 | Basf Ag | Procédé pour la préparation de dérivés de l'aldéhyde omega-hydroxytiglique |
| DE1188577B (de) * | 1963-08-23 | 1965-03-11 | Basf Ag | Verfahren zur Herstellung von omega-Chlor bzw. omega-Bromtiglinaldehyd, deren AcetaleAcylaten |
| NL175906C (nl) * | 1976-02-25 | 1985-01-16 | Rhone Poulenc Ind | Werkwijze voor het bereiden van halogeenacetalen van alkenisch onverzadigde aldehyden. |
| NL176165C (nl) * | 1976-02-25 | 1985-03-01 | Rhone Poulenc Ind | Werkwijze voor het bereiden van halogeenacetalen van alkenisch onverzadigde aldehyden. |
| FR2342265A1 (fr) * | 1976-02-25 | 1977-09-23 | Rhone Poulenc Ind | Procede de preparation d'halogenoacetals a partir d'esters |
| FR2342266A1 (fr) * | 1976-02-25 | 1977-09-23 | Rhone Poulenc Ind | Procede de preparation d'halogenoacetals a partir d'enoxysilanes |
| DE2917413A1 (de) * | 1979-04-28 | 1980-11-06 | Basf Ag | Verfahren zur herstellung von cyclischen acetalen von trans-4-chlor-3-methyl- 2-buten-1-al sowie von trans-3-methyl-2- buten-1,4-dial-1-monoacetalen |
-
1981
- 1981-12-18 FR FR8123685A patent/FR2518534A1/fr active Granted
-
1982
- 1982-12-15 CA CA000417787A patent/CA1184208A/fr not_active Expired
- 1982-12-16 JP JP57219343A patent/JPS58110532A/ja active Granted
- 1982-12-16 US US06/450,447 patent/US4503239A/en not_active Expired - Fee Related
- 1982-12-17 AT AT82402327T patent/ATE12220T1/de not_active IP Right Cessation
- 1982-12-17 SU SU823523097A patent/SU1240350A3/ru active
- 1982-12-17 EP EP82402327A patent/EP0082782B1/fr not_active Expired
- 1982-12-17 DE DE8282402327T patent/DE3262724D1/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Патент СССР № 880250, кл. С 07 С 43/313, опублик. 07.11.81. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1184208A (fr) | 1985-03-19 |
| EP0082782B1 (fr) | 1985-03-20 |
| ATE12220T1 (de) | 1985-04-15 |
| FR2518534B1 (cg-RX-API-DMAC10.html) | 1984-03-09 |
| US4503239A (en) | 1985-03-05 |
| FR2518534A1 (fr) | 1983-06-24 |
| JPS58110532A (ja) | 1983-07-01 |
| DE3262724D1 (en) | 1985-04-25 |
| EP0082782A1 (fr) | 1983-06-29 |
| JPH0212457B2 (cg-RX-API-DMAC10.html) | 1990-03-20 |
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