NO812853L - Fremgangsmaate for fremstilling av 2,5-dimetyl-2,4-heksadien - Google Patents
Fremgangsmaate for fremstilling av 2,5-dimetyl-2,4-heksadienInfo
- Publication number
- NO812853L NO812853L NO812853A NO812853A NO812853L NO 812853 L NO812853 L NO 812853L NO 812853 A NO812853 A NO 812853A NO 812853 A NO812853 A NO 812853A NO 812853 L NO812853 L NO 812853L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- dimethyl
- dhad
- mol
- hexadiene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 13
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 101100452478 Arabidopsis thaliana DHAD gene Proteins 0.000 description 43
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 43
- 235000011007 phosphoric acid Nutrition 0.000 description 23
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- BBLDTXFLAHKYFJ-UHFFFAOYSA-N 2,2,5,5-tetramethyloxolane Chemical compound CC1(C)CCC(C)(C)O1 BBLDTXFLAHKYFJ-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical compound CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CDLDJGNSVFBIAG-UHFFFAOYSA-N 2,2,3,3-tetramethyloxolane Chemical compound CC1(C)CCOC1(C)C CDLDJGNSVFBIAG-UHFFFAOYSA-N 0.000 description 2
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- KETIPZIBBSVDPW-VMPITWQZSA-N (4e)-2,4-dimethylhexa-2,4-diene Chemical compound C\C=C(/C)C=C(C)C KETIPZIBBSVDPW-VMPITWQZSA-N 0.000 description 1
- ZXLUFQJSMQSMTR-AATRIKPKSA-N (4e)-2-methylhepta-2,4-diene Chemical compound CC\C=C\C=C(C)C ZXLUFQJSMQSMTR-AATRIKPKSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- MXZKRWKJCMNLRW-UHFFFAOYSA-N 2,5-dimethylhepta-2,4-diene Chemical compound CCC(C)=CC=C(C)C MXZKRWKJCMNLRW-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- HOKNEAXKAGETSV-UHFFFAOYSA-N 3,6-dimethylocta-3,5-diene Chemical compound CCC(C)=CC=C(C)CC HOKNEAXKAGETSV-UHFFFAOYSA-N 0.000 description 1
- -1 85% phosphoric acid Chemical class 0.000 description 1
- XSRGEVICXWRCRF-UHFFFAOYSA-N CC=CC=CC.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound CC=CC=CC.C1=CC=CC=C1C1=CC=CC=C1 XSRGEVICXWRCRF-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
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- UDDGYKGCIIVQHJ-UHFFFAOYSA-N benzene-1,4-diol;4-methoxyphenol Chemical compound OC1=CC=C(O)C=C1.COC1=CC=C(O)C=C1 UDDGYKGCIIVQHJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229960004251 hydroquinine Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/055—Sulfates or other compounds comprising the anion (SnO3n+1)2- with alkali metals, copper, gold or silver
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
- C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24353/80A IT1141028B (it) | 1980-08-29 | 1980-08-29 | Procedimento per la preparazione di 2,5-dimetil 2,4-esadiene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO812853L true NO812853L (no) | 1982-03-01 |
Family
ID=11213222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO812853A NO812853L (no) | 1980-08-29 | 1981-08-24 | Fremgangsmaate for fremstilling av 2,5-dimetyl-2,4-heksadien |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4409419A (fr) |
| JP (1) | JPS5777628A (fr) |
| AT (1) | AT375329B (fr) |
| BE (1) | BE890096A (fr) |
| CA (1) | CA1150320A (fr) |
| DD (1) | DD201670A5 (fr) |
| DE (1) | DE3134107C2 (fr) |
| DK (1) | DK364981A (fr) |
| ES (1) | ES505478A0 (fr) |
| FR (1) | FR2489302A1 (fr) |
| GB (1) | GB2083071B (fr) |
| IT (1) | IT1141028B (fr) |
| NL (1) | NL8104014A (fr) |
| NO (1) | NO812853L (fr) |
| SE (1) | SE8105108L (fr) |
| ZA (1) | ZA815429B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3317165A1 (de) * | 1983-05-11 | 1984-11-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von olefinen durch wasserabspaltung aus alkoholen |
| US4507518A (en) * | 1983-12-14 | 1985-03-26 | Penick Corporation | Dehydration of 2,5-dimethyl-2,5-hexanediol |
| JP4915159B2 (ja) * | 2006-07-18 | 2012-04-11 | 三菱化学株式会社 | １，３−シクロヘキサジエン化合物の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1002399A (en) * | 1910-12-27 | 1911-09-05 | Farbenfab Vorm Bayer F & Co | Process of producing beta-gamma-dimethylerythrene. |
| US1179408A (en) * | 1912-12-06 | 1916-04-18 | Farben Fabriken Vorm Friedr Bayer & Co | Process for the production of hydrocarbons of the erythrene series. |
| US1944153A (en) * | 1928-10-04 | 1934-01-23 | Ig Farbenindustrie Ag | Production of diolefines |
| US1923569A (en) * | 1929-07-22 | 1933-08-22 | Ig Farbenindustrie Ag | Production of diolefines |
| US2310809A (en) * | 1939-04-06 | 1943-02-09 | Reppe Walter | Method of preparing diolefins |
| GB587092A (en) * | 1944-01-03 | 1947-04-14 | Shell Dev | Dehydration of polyhydric alcohols |
| US2461362A (en) * | 1945-02-09 | 1949-02-08 | Standard Oil Dev Co | Preparation of 2-3 methyl butadiene 1-3 |
| US2715649A (en) * | 1952-07-26 | 1955-08-16 | Fmc Corp | Catalytic dehydration of a hexanediol to a hexadiene |
| US2957929A (en) * | 1958-06-23 | 1960-10-25 | Shell Oil Co | Production of alpha, omega-diisopropenylalkanes |
-
1980
- 1980-08-29 IT IT24353/80A patent/IT1141028B/it active
-
1981
- 1981-08-06 US US06/290,655 patent/US4409419A/en not_active Expired - Fee Related
- 1981-08-06 ZA ZA815429A patent/ZA815429B/xx unknown
- 1981-08-11 CA CA000383585A patent/CA1150320A/fr not_active Expired
- 1981-08-17 DK DK364981A patent/DK364981A/da not_active Application Discontinuation
- 1981-08-20 FR FR8116017A patent/FR2489302A1/fr active Pending
- 1981-08-24 NO NO812853A patent/NO812853L/no unknown
- 1981-08-25 GB GB8125946A patent/GB2083071B/en not_active Expired
- 1981-08-26 BE BE0/205774A patent/BE890096A/fr not_active IP Right Cessation
- 1981-08-28 DE DE3134107A patent/DE3134107C2/de not_active Expired
- 1981-08-28 DD DD81232877A patent/DD201670A5/de unknown
- 1981-08-28 JP JP56134357A patent/JPS5777628A/ja active Pending
- 1981-08-28 SE SE8105108A patent/SE8105108L/xx not_active Application Discontinuation
- 1981-08-28 AT AT0374581A patent/AT375329B/de not_active IP Right Cessation
- 1981-08-28 NL NL8104014A patent/NL8104014A/nl not_active Application Discontinuation
- 1981-08-28 ES ES505478A patent/ES505478A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8024353A0 (it) | 1980-08-29 |
| US4409419A (en) | 1983-10-11 |
| ES8303271A1 (es) | 1983-02-01 |
| ES505478A0 (es) | 1983-02-01 |
| ATA374581A (de) | 1983-12-15 |
| CA1150320A (fr) | 1983-07-19 |
| AT375329B (de) | 1984-07-25 |
| DK364981A (da) | 1982-03-01 |
| DD201670A5 (de) | 1983-08-03 |
| SE8105108L (sv) | 1982-03-01 |
| NL8104014A (nl) | 1982-03-16 |
| JPS5777628A (en) | 1982-05-15 |
| ZA815429B (en) | 1982-08-25 |
| GB2083071B (en) | 1984-06-06 |
| FR2489302A1 (fr) | 1982-03-05 |
| DE3134107A1 (de) | 1982-04-15 |
| DE3134107C2 (de) | 1983-12-08 |
| BE890096A (fr) | 1982-02-26 |
| IT1141028B (it) | 1986-10-01 |
| GB2083071A (en) | 1982-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3029294A (en) | Purification of phenol | |
| US2516627A (en) | Production of allyl acrylate from acrolein | |
| NO812853L (no) | Fremgangsmaate for fremstilling av 2,5-dimetyl-2,4-heksadien | |
| DE2430520A1 (de) | Verfahren zur reinigung von rohem maleinsaeureanhydrid | |
| Pledger, Jr | Reactions of Allene. I. Diels-Alder Adducts | |
| Cason et al. | Branched-Chain Fatty Acids. XVI. Synthesis of the Optical Isomers of 15-Methyloctadecanoic Acid1 | |
| DE2917779B1 (de) | Verfahren zur Herstellung von 2,3-Dimethylbuten-2 | |
| US4855516A (en) | Method of manufacturing 2-propyn-1-ol | |
| NO140544B (no) | Styreanordning for en kjoerbar skogavvirkningsmaskin | |
| EP0003399B1 (fr) | Procédé pour augmenter la selectivité pour l'acide acétique dans la préparation d'un mélange d'acides monocarboxyliques contenant de 1 à 3 atomes de carbone par oxydation d'hydrocarbures de paraffine | |
| JPS631935B2 (fr) | ||
| US3011003A (en) | Process for the preparation of trivinyl cyclohexanes | |
| DE281802C (fr) | ||
| GB411741A (en) | Process for the conversion of unsaturated alcohols | |
| US2184164A (en) | Production of butadiene from 1, 3-butylene glycol | |
| US1893802A (en) | Method of producing para-cymene | |
| US2789141A (en) | Production of alpha-diketones | |
| Bussert et al. | Synthesis of the Geometrical Isomers of 1, 2, 3-Trimethylcyclohexane1 | |
| US4678544A (en) | Process for the separation of 2MBA from MIPK | |
| SU107542A1 (ru) | Способ получени 3-хлордифениламина | |
| JPH0273033A (ja) | ４，４―ジメチル―１―（ｐ―クロロフエニル）ペンタン―３―オンの製造方法 | |
| DE2510088C2 (de) | Verfahren zur fraktionierten Destillation von Diacetoxybutenisomeren | |
| US4820874A (en) | Increasing the yield of 2.5.6-trimethylcyclohex-2-en-1-one | |
| Bassett et al. | The Production of Isoprene from Rubber | |
| SU294829A1 (ru) | Способ получения диеновых углеводородов |