DE1269618B - Verfahren zur Herstellung von Addukten des Tetrachlorkohlenstoffs an olefinisch ungesaettigten Verbindungen - Google Patents
Verfahren zur Herstellung von Addukten des Tetrachlorkohlenstoffs an olefinisch ungesaettigten VerbindungenInfo
- Publication number
- DE1269618B DE1269618B DEP1269618A DE1269618A DE1269618B DE 1269618 B DE1269618 B DE 1269618B DE P1269618 A DEP1269618 A DE P1269618A DE 1269618 A DE1269618 A DE 1269618A DE 1269618 B DE1269618 B DE 1269618B
- Authority
- DE
- Germany
- Prior art keywords
- carbon tetrachloride
- double bonds
- per
- compounds
- adducts
- 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 title claims description 73
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 20
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- -1 carbalkoxy Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 229920001971 elastomer Polymers 0.000 claims description 8
- 239000005060 rubber Substances 0.000 claims description 8
- 244000028419 Styrax benzoin Species 0.000 claims description 7
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 7
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229960002130 benzoin Drugs 0.000 claims description 7
- 235000019382 gum benzoic Nutrition 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002506 iron compounds Chemical class 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 9
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- CQWHLNCODHOFCT-UHFFFAOYSA-N 4-phenylbut-3-enenitrile Chemical compound N#CCC=CC1=CC=CC=C1 CQWHLNCODHOFCT-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 102000055501 telomere Human genes 0.000 description 3
- 108091035539 telomere Proteins 0.000 description 3
- 210000003411 telomere Anatomy 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- MXUPILKWZJJDFH-UHFFFAOYSA-N acetonitrile;prop-2-enenitrile Chemical compound CC#N.C=CC#N MXUPILKWZJJDFH-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- ASJPOIIEOZWUCC-UHFFFAOYSA-N 1,1,1,5-tetrachloropent-2-ene Chemical compound ClC(C=CCCCl)(Cl)Cl ASJPOIIEOZWUCC-UHFFFAOYSA-N 0.000 description 1
- VZEWJVRACUZHQR-UHFFFAOYSA-N 1,1,1,5-tetrachloropentane Chemical compound ClCCCCC(Cl)(Cl)Cl VZEWJVRACUZHQR-UHFFFAOYSA-N 0.000 description 1
- HIZWVJSDYNNBMS-UHFFFAOYSA-N 1,1,1,7-tetrachloroheptane Chemical compound ClCCCCCCC(Cl)(Cl)Cl HIZWVJSDYNNBMS-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- BSKZVKRRNOOCCA-UHFFFAOYSA-N C(C)#N.C(C=C)(=O)OC Chemical compound C(C)#N.C(C=C)(=O)OC BSKZVKRRNOOCCA-UHFFFAOYSA-N 0.000 description 1
- JNWFRBSYKZNQNF-UHFFFAOYSA-N C(C)(C)O.C(C=C)#N Chemical compound C(C)(C)O.C(C=C)#N JNWFRBSYKZNQNF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- LHMBYTUQIGAEPX-UHFFFAOYSA-N acetonitrile;tetrachloromethane Chemical compound CC#N.ClC(Cl)(Cl)Cl LHMBYTUQIGAEPX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IWQUIQRVAAPHMQ-UHFFFAOYSA-N buta-1,3-diene;methanol Chemical compound OC.C=CC=C IWQUIQRVAAPHMQ-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- WQCBTNCMYAUBGU-UHFFFAOYSA-N ethene propan-2-ol Chemical compound C=C.CC(C)O WQCBTNCMYAUBGU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DXYFFDHUTOBVEK-UHFFFAOYSA-N methanol;styrene Chemical compound OC.C=CC1=CC=CC=C1 DXYFFDHUTOBVEK-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PPBMLXKDVBCHMO-UHFFFAOYSA-N propan-2-ol;styrene Chemical compound CC(C)O.C=CC1=CC=CC=C1 PPBMLXKDVBCHMO-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/12—Incorporating halogen atoms into the molecule
- C08C19/18—Incorporating halogen atoms into the molecule by reaction with hydrocarbons substituted by halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl 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
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL1607961 | 1961-09-28 | ||
| IL1608061 | 1961-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1269618B true DE1269618B (de) | 1968-06-06 |
Family
ID=26320401
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1268605A Pending DE1268605B (de) | 1961-09-28 | 1962-09-26 | Verfahren zur Herstellung von 1:1-Addukten aus Alkenen bzw. Alkadienen und Chloroform |
| DEP1269618A Pending DE1269618B (de) | 1961-09-28 | 1962-09-26 | Verfahren zur Herstellung von Addukten des Tetrachlorkohlenstoffs an olefinisch ungesaettigten Verbindungen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1268605A Pending DE1268605B (de) | 1961-09-28 | 1962-09-26 | Verfahren zur Herstellung von 1:1-Addukten aus Alkenen bzw. Alkadienen und Chloroform |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5347059A (en) * | 1991-07-10 | 1994-09-13 | Solvay (Societe Anonyme) | Process for preparing 1,1-dichloro-1,3,3,3-tetra-fluoropropane |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3399241A (en) * | 1964-02-26 | 1968-08-27 | Olin Mathieson | Process for preparing 2, 4, 4, 4-tetrachlorobutanol from allyl alcohol and ccl4 in the presence of powdered iron catalyst |
| US3399217A (en) * | 1964-03-04 | 1968-08-27 | Olin Mathieson | Catalyst system for reaction of an allyl alcohol and carbon tetrachloride to produce2, 4, 4, 4-tetrachlorobutanol |
| US3993586A (en) * | 1973-04-11 | 1976-11-23 | Bayer Aktiengesellschaft | Water-soluble complex of cuprous chloride, hydrochloric acid and at least one amine or amine salt |
| GB1498931A (en) * | 1975-02-12 | 1978-01-25 | Sumitomo Chemical Co | Tetrahalopentyl ketone derivatives processes for producing them and their conversion to beta-dihaloethenylcyclopropane derivatives |
| JPS5259103A (en) * | 1975-11-10 | 1977-05-16 | Shin Etsu Chem Co Ltd | Process for preparation of tetrachloroalkane |
| US4036897A (en) * | 1976-08-04 | 1977-07-19 | The Lummus Company | Production of hexachlorocyclopentadiene |
| US4271325A (en) * | 1976-11-18 | 1981-06-02 | Stauffer Chemical Company | Process for the manufacture of 1,1-dihalo-4-methyl-1,3-pentadienes |
| FR2425451A1 (fr) * | 1978-05-09 | 1979-12-07 | Anvar | Procede pour l'addition de groupes trihalogenomethyle fonctionnels sur des polyalcadienes |
| DE3111848A1 (de) * | 1981-03-26 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von substituierten (alpha)-halogen-propionsaeuren und ihren derivaten |
| DE3136983A1 (de) * | 1981-09-17 | 1983-03-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,1,1-trichlormethylverbindungen |
| US4691065A (en) * | 1983-11-02 | 1987-09-01 | Occidental Chemical Corporation | Chlorotrifluoroethylene telomerization process |
| KR100256505B1 (ko) * | 1993-07-29 | 2000-05-15 | 크리스 로저 에이치 | 1,1,1,3,3-펜타플루오르 프로판의 제조방법 |
| US5395997A (en) * | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
| HUT75954A (en) * | 1994-07-11 | 1997-05-28 | Allied Signal Inc | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
| DE69626415T2 (de) | 1995-08-01 | 2003-09-25 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur herstellung von halogenkohlenwasserstoffen und ausgewählte verbindungen und azeotrope mit hf |
| US6755942B1 (en) | 1995-08-01 | 2004-06-29 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with HF |
| US5633413A (en) * | 1995-08-08 | 1997-05-27 | Alliedsignal Inc. | Continuous process for the production of vinylidene chloride telomers |
| US5817893A (en) * | 1996-06-18 | 1998-10-06 | E. I. Du Pont De Nemours And Company | Processes for the manufacture and purification of 1,1,2,2,3,3,4,4-octafluorobutane and by-products |
| ES2173567T3 (es) | 1997-01-16 | 2002-10-16 | Du Pont | Proceso para la fabricacion de halocarburos. |
| BE1011319A3 (fr) * | 1997-05-05 | 1999-07-06 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| EP0984911B1 (fr) * | 1997-05-05 | 2004-04-14 | SOLVAY (Société Anonyme) | Procede de preparation d'hydrocarbures halogenes |
| CA2288939A1 (fr) | 1997-05-05 | 1998-11-12 | Solvay (Societe Anonyme) | Procede de preparation de 1,1,1,3,3-pentachlorobutane |
| BE1011249A3 (fr) * | 1997-07-03 | 1999-06-01 | Solvay | Pentachlorobutane, son procede de fabrication et son utilisation, procede de preparation du 1,1-difluoro-2-trifluoromethylpropane et utilisation de ce compose. |
| ES2189240T3 (es) | 1997-08-08 | 2003-07-01 | Solvay | Procedimiento de preparacion de hidrocarburos halogenados. |
| US6187976B1 (en) | 1998-04-09 | 2001-02-13 | Alliedsignal Inc. | Process for the preparation of fluorine containing hydrohalocarbons |
| BE1012268A3 (fr) | 1998-11-05 | 2000-08-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| US7253047B2 (en) * | 1999-09-01 | 2007-08-07 | Micron Technology, Inc. | Semiconductor processing methods of forming transistors, semiconductor processing methods of forming dynamic random access memory circuitry, and related integrated circuitry |
| ES2220547T3 (es) | 1999-10-06 | 2004-12-16 | Solvay (Societe Anonyme) | Procedimiento de preparacion de hidrocarburos halogenados. |
| AU7908900A (en) | 1999-10-06 | 2001-05-10 | Solvay (Societe Anonyme) | Method for obtaining halogenated hydrocarbons in the presence of a co-catalyst |
| WO2004001877A2 (en) * | 2002-06-21 | 2003-12-31 | The Regents Of The University Of California | Electrolytes for electrooptic devices comprising ionic liquids |
| US20040225166A1 (en) * | 2003-05-05 | 2004-11-11 | Vulcan Chemicals A Business Group Of Vulcan Materials Company | Method for producing 1,1,1,3-tetrachloropropane and other haloalkanes with iron catalyst |
| US20050049443A1 (en) * | 2003-08-28 | 2005-03-03 | Vulcan Chemicals A Business Group Of Vulcan Materials Company | Method for producing 1,1,1,3-tetrachloropropane and other haloalkanes using a copper catalyst |
| KR101397113B1 (ko) | 2006-10-03 | 2014-05-19 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| US9738577B2 (en) * | 2006-10-11 | 2017-08-22 | Honeywell International Inc. | Process for the manufacture of 1,1,1,3,3-pentachloropropane |
| CN105646136A (zh) * | 2008-10-13 | 2016-06-08 | 蓝立方知识产权公司 | 用于生产氯化和/或氟化丙烯的方法 |
| WO2011044522A2 (en) * | 2009-10-09 | 2011-04-14 | Dow Global Technologies, Inc | Adiabatic plug flow reactors and processes incorporating the same |
| CN102596387B (zh) | 2009-10-09 | 2015-11-25 | 陶氏环球技术有限责任公司 | 生产氯化和/或氟化丙烯和高级烯烃的等温多管反应器和方法 |
| KR20120084729A (ko) * | 2009-10-09 | 2012-07-30 | 다우 글로벌 테크놀로지스 엘엘씨 | 염화 및/또는 불화 프로펜 및 고급 알켄의 제조 방법 |
| KR20120093857A (ko) * | 2009-10-09 | 2012-08-23 | 다우 글로벌 테크놀로지스 엘엘씨 | 염화 및/또는 불화 프로펜의 제조 방법 |
| US8426655B2 (en) | 2010-03-26 | 2013-04-23 | Honeywell International Inc. | Process for the manufacture of hexafluoro-2-butene |
| EP2714630A1 (en) | 2011-05-31 | 2014-04-09 | Dow Global Technologies LLC | Process for the production of chlorinated propenes |
| CN103562163B (zh) | 2011-05-31 | 2015-12-23 | 陶氏环球技术有限责任公司 | 生产氯化丙烯类的方法 |
| CN103596908A (zh) | 2011-06-08 | 2014-02-19 | 陶氏益农公司 | 生产氯化和/或氟化丙烯的方法 |
| EP2739595B1 (en) | 2011-08-07 | 2018-12-12 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
| EP2739596B1 (en) | 2011-08-07 | 2019-05-01 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
| JP6050372B2 (ja) | 2011-11-21 | 2016-12-21 | ブルー キューブ アイピー エルエルシー | クロロアルカンの製造方法 |
| EP2785671B1 (en) | 2011-12-02 | 2017-03-01 | Blue Cube IP LLC | Process for the production of chlorinated propanes |
| EP2785670B1 (en) | 2011-12-02 | 2017-10-25 | Blue Cube IP LLC | Process for the production of chlorinated alkanes |
| US9334205B2 (en) | 2011-12-13 | 2016-05-10 | Blue Cube Ip Llc | Process for the production of chlorinated propanes and propenes |
| JP2015503523A (ja) | 2011-12-22 | 2015-02-02 | ダウ グローバル テクノロジーズ エルエルシー | テトラクロロメタンの製造方法 |
| CN104159874B (zh) | 2011-12-23 | 2016-08-24 | 陶氏环球技术有限责任公司 | 生产链烯和/或芳族化合物的方法 |
| CA2884435A1 (en) | 2012-09-20 | 2014-03-27 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| WO2014046970A1 (en) | 2012-09-20 | 2014-03-27 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| JP6272878B2 (ja) | 2012-09-30 | 2018-01-31 | ブルー キューブ アイピー エルエルシー | せきクエンチおよびそれを組み込んだ方法 |
| WO2014066083A1 (en) | 2012-10-26 | 2014-05-01 | Dow Global Technologies, Llc | Mixer and reactor and process incorporating the same |
| CA2893841C (en) | 2012-12-18 | 2018-07-24 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| US9475740B2 (en) | 2012-12-19 | 2016-10-25 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| CA2901450A1 (en) | 2013-02-27 | 2014-09-04 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| CA2903760C (en) | 2013-03-09 | 2018-02-20 | Blue Cube Ip Llc | Process for the production of chlorinated alkanes |
| CN104230751B (zh) * | 2014-06-16 | 2016-05-25 | 浙江中欣氟材股份有限公司 | 一种2,4,4,4-四氯丁腈的合成方法 |
| CN104230752B (zh) * | 2014-08-22 | 2016-05-25 | 浙江中欣氟材股份有限公司 | 一种2,4,4,4-四氯丁腈的制备方法 |
| WO2019195248A1 (en) * | 2018-04-03 | 2019-10-10 | Blue Cube Ip Llc | Method for recycling catalyst in the production of chlorinated alkanes |
-
0
- BE BE622938D patent/BE622938A/xx unknown
- BE BE622939D patent/BE622939A/xx unknown
-
1962
- 1962-09-11 GB GB34672/61A patent/GB1023423A/en not_active Expired
- 1962-09-11 GB GB34673/62A patent/GB1022684A/en not_active Expired
- 1962-09-26 DE DEP1268605A patent/DE1268605B/de active Pending
- 1962-09-26 DE DEP1269618A patent/DE1269618B/de active Pending
- 1962-09-27 FR FR910636A patent/FR1334749A/fr not_active Expired
- 1962-09-27 FR FR910638A patent/FR1335343A/fr not_active Expired
-
1965
- 1965-07-27 US US475274A patent/US3651019A/en not_active Expired - Lifetime
-
1966
- 1966-03-22 GB GB12585/66A patent/GB1146463A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5347059A (en) * | 1991-07-10 | 1994-09-13 | Solvay (Societe Anonyme) | Process for preparing 1,1-dichloro-1,3,3,3-tetra-fluoropropane |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1022684A (en) | 1966-03-16 |
| GB1023423A (en) | 1966-03-23 |
| BE622939A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB1146463A (en) | 1969-03-26 |
| BE622938A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US3651019A (en) | 1972-03-21 |
| DE1268605B (de) | 1968-05-22 |
| FR1335343A (fr) | 1963-08-16 |
| FR1334749A (fr) | 1963-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1269618B (de) | Verfahren zur Herstellung von Addukten des Tetrachlorkohlenstoffs an olefinisch ungesaettigten Verbindungen | |
| DE1253719B (de) | Verfahren zur Herstellung von Bromderivaten des Diphenylaethers bzw. der Mischungen aus Diphenylaether und Diphenyl oder Di- bzw. Tri- oder Tetraphenylmethan mit mehr als 3 Bromatomen im Molekuel | |
| DE1568042A1 (de) | Verfahren zur Herstellung von fluorierten AEthern | |
| DE1264444B (de) | Verfahren zum Umwandeln von aliphatischen Halogeniden in Carbonsaeureester | |
| DE1266754B (de) | Verfahren zur Herstellung von 1, 1, 3, 4, 4, 6-Hexamethyl-1, 2, 3, 4-tetrahydronaphthalin | |
| DE1086226B (de) | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) | |
| DE2417985A1 (de) | Diolefindimerisierungskatalysatoren und verfahren zur katalytischen dimerisierung von diolefinen | |
| DE875356C (de) | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Hydroperoxyden | |
| DE1520792A1 (de) | Verfahren zur Polymerisation von Olefinen | |
| DE948088C (de) | Verfahren zur Herstellung von Corpolymerisaten | |
| DE656133C (de) | Verfahren zur Stabilisierung von Polyvinylchlorid | |
| DE844442C (de) | Verfahren zur Herstellung von 1, 1-Dihalogen-1, 3-alkadienen | |
| DE2047140A1 (de) | Verfahren zur Herstellung von Polypropylen und/oder Polybutylen Ölen | |
| DE1520067A1 (de) | Verfahren zur Telomerisation von AEthylen | |
| CH630053A5 (de) | Verfahren zur herstellung eines gemisches aus m-aryloxybenzylchlorid und m-aryloxybenzalchlorid. | |
| DE532271C (de) | Verfahren zur Herstellung kautschuk- oder guttaperchaaehnlicher Massen | |
| DE2120364A1 (en) | Polyfluoroalkane carboxylic acids prepn, polymn emulsifiers | |
| EP0219092A1 (de) | Verfahren zur Herstellubg von Alenylaromaten | |
| DE847150C (de) | Verfahren zur Durchfuehrung von Kettenreaktionen, die durch freie Atome und bzw. oder freie Radikale eingeleitet werden | |
| DE1420490A1 (de) | Endstaendig ungesaettigte Polyalkenylmethane,ihre Herstellung und Verwendung | |
| DE886907C (de) | Verfahren zur Kondensation von Halogenkohlenwasserstoffen | |
| DE1180944B (de) | Verfahren zur Herstellung von trans-(1, 4)-Polybutadien | |
| AT229025B (de) | Verfahren zur Herstellung von Katalysatoren für die Polymerisation von Olefinen | |
| DE1468411C3 (de) | Verfahren zur Herstellung von 2-Methylenglutarsäurenitril | |
| DE671063C (de) | Verfahren zur gleichzeitigen Einfuehrung von Chlor und Alkylresten in organische Verbindungen mit mindestens einer olefinischen Doppelbindung |