DE1967158C2 - Verfahren zur Herstellung von 2-Chlorbutadien-03) - Google Patents
Verfahren zur Herstellung von 2-Chlorbutadien-03)Info
- Publication number
- DE1967158C2 DE1967158C2 DE1967158A DE1967158A DE1967158C2 DE 1967158 C2 DE1967158 C2 DE 1967158C2 DE 1967158 A DE1967158 A DE 1967158A DE 1967158 A DE1967158 A DE 1967158A DE 1967158 C2 DE1967158 C2 DE 1967158C2
- Authority
- DE
- Germany
- Prior art keywords
- iodide
- reaction
- chlorobutadiene
- sulfonium
- hydroxide
- 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 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 15
- -1 sulfonium compound Chemical class 0.000 claims description 9
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical class CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical class ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RABUZJZUBFMWSH-UHFFFAOYSA-N sulfane;hydroiodide Chemical compound [SH3+].[I-] RABUZJZUBFMWSH-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 1
- ZTFDWEJBCDWTBA-UHFFFAOYSA-N 1-(2-hydroxytetradecylsulfanyl)tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(O)CSCC(O)CCCCCCCCCCCC ZTFDWEJBCDWTBA-UHFFFAOYSA-N 0.000 description 1
- LHNRHYOMDUJLLM-UHFFFAOYSA-N 1-hexylsulfanylhexane Chemical compound CCCCCCSCCCCCC LHNRHYOMDUJLLM-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KVYWVRHLHBGLKQ-UHFFFAOYSA-M CCCCCCCCCCCC[S+](CCO)CCO.[Cl-] Chemical compound CCCCCCCCCCCC[S+](CCO)CCO.[Cl-] KVYWVRHLHBGLKQ-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000004821 distillation Methods 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
- CSSXFMXXEQYDFF-UHFFFAOYSA-M dodecyl-ethyl-methylsulfanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[S+](C)CC CSSXFMXXEQYDFF-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- QGASWLPHNZXFCZ-UHFFFAOYSA-M methyl(dioctyl)sulfanium;iodide Chemical compound [I-].CCCCCCCC[S+](C)CCCCCCCC QGASWLPHNZXFCZ-UHFFFAOYSA-M 0.000 description 1
- WZZMHOBVLAEJOD-UHFFFAOYSA-N methylsulfanylmethane;hydrobromide Chemical compound [Br-].C[SH+]C WZZMHOBVLAEJOD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- MCOWGUNDBBHKAM-UHFFFAOYSA-N thiohypoiodous acid Chemical compound IS MCOWGUNDBBHKAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/34—Dehalogenation using reactive chemical agents able to degrade
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- 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
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/22—Organic substances containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71289868A | 1968-02-28 | 1968-02-28 | |
| US71289568A | 1968-02-28 | 1968-02-28 | |
| US00712899A US3754044A (en) | 1968-02-28 | 1968-02-28 | Dehydrohalogenation of halogenated compounds |
| US708801A US3639492A (en) | 1968-02-28 | 1968-02-28 | Dehydrohalogenation of halogenated compounds |
| US712896*A US3639493A (en) | 1968-02-28 | 1968-02-28 | Dehydrohalogenation of halogenated compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1967158B1 DE1967158B1 (de) | 1979-09-13 |
| DE1967158C2 true DE1967158C2 (de) | 1980-06-12 |
Family
ID=27542118
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967158A Expired DE1967158C2 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-03) |
| DE1967156A Expired DE1967156C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-<13) |
| DE1909952A Expired DE1909952C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
| DE1967157A Expired DE1967157C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
| DE1967155A Expired DE1967155C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967156A Expired DE1967156C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-<13) |
| DE1909952A Expired DE1909952C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
| DE1967157A Expired DE1967157C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
| DE1967155A Expired DE1967155C3 (de) | 1968-02-28 | 1969-02-27 | Verfahren zur Herstellung von 2-Chlorbutadien-(13) |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4945379B1 (https=) |
| BE (1) | BE728755R (https=) |
| DE (5) | DE1967158C2 (https=) |
| GB (1) | GB1235591A (https=) |
| NL (1) | NL6903151A (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5112031U (https=) * | 1974-07-15 | 1976-01-29 | ||
| DE3046461A1 (de) * | 1980-12-10 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,1-dichloralkylenverbindungen |
| JPS5857576U (ja) * | 1981-10-15 | 1983-04-19 | 三菱電機株式会社 | 密閉形電動圧縮機 |
| KR100862281B1 (ko) | 2000-12-04 | 2008-10-15 | 시바 홀딩 인크 | 오늄 염, 이를 포함하는 화학적으로 증폭된 감광성 내식막 조성물 및 감광성 내식막의 제조방법 |
| CN105452200A (zh) * | 2013-08-01 | 2016-03-30 | 索尔维公司 | 用于卤代有机非聚合化合物的脱卤化氢的方法 |
| KR20240073882A (ko) * | 2021-10-04 | 2024-05-27 | 가부시끼가이샤 레조낙 | 헥사플루오로-1,3-부타디엔의 제조 방법 |
-
1969
- 1969-02-21 BE BE728755A patent/BE728755R/fr active
- 1969-02-25 GB GB9982/69A patent/GB1235591A/en not_active Expired
- 1969-02-27 DE DE1967158A patent/DE1967158C2/de not_active Expired
- 1969-02-27 DE DE1967156A patent/DE1967156C3/de not_active Expired
- 1969-02-27 DE DE1909952A patent/DE1909952C3/de not_active Expired
- 1969-02-27 DE DE1967157A patent/DE1967157C3/de not_active Expired
- 1969-02-27 DE DE1967155A patent/DE1967155C3/de not_active Expired
- 1969-02-28 JP JP44014962A patent/JPS4945379B1/ja active Pending
- 1969-02-28 NL NL6903151A patent/NL6903151A/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1235591A (en) | 1971-06-16 |
| JPS4945379B1 (https=) | 1974-12-04 |
| DE1967157B2 (de) | 1979-05-31 |
| DE1967156C3 (de) | 1980-03-20 |
| DE1967158B1 (de) | 1979-09-13 |
| BE728755R (fr) | 1969-08-01 |
| NL6903151A (nl) | 1969-09-01 |
| DE1909952C3 (de) | 1980-12-11 |
| DE1967155C3 (de) | 1980-03-20 |
| DE1967156B2 (de) | 1979-05-31 |
| DE1967157C3 (de) | 1980-03-20 |
| DE1967155B2 (de) | 1979-05-31 |
| DE1909952A1 (de) | 1970-08-27 |
| DE1909952B2 (de) | 1980-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination |