BE439587A - - Google Patents

Info

Publication number

BE439587A

BE439587A BE439587DA BE439587A BE 439587 A BE439587 A BE 439587A BE 439587D A BE439587D A BE 439587DA BE 439587 A BE439587 A BE 439587A

Authority

BE

Belgium

Prior art keywords

parts

condensation

weight

ethyl

reaction

Prior art date

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• 238000009833 condensation Methods 0.000 claims description 12
• 230000005494 condensation Effects 0.000 claims description 12
• -1 aliphatic aldehydes Chemical class 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 150000001247 metal acetylides Chemical class 0.000 claims description 3
• 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
• 150000004679 hydroxides Chemical class 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 description 8
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
• 235000011941 Tilia x europaea Nutrition 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
• 239000004571 lime Substances 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 150000002334 glycols Chemical class 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000000920 calcium hydroxide Substances 0.000 description 2
• 235000011116 calcium hydroxide Nutrition 0.000 description 2
• BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
• 239000000292 calcium oxide Substances 0.000 description 2
• ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
• 238000005194 fractionation Methods 0.000 description 2
• XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 description 1
• IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
• 239000005997 Calcium carbide Substances 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
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 238000005882 aldol condensation reaction Methods 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910052788 barium Inorganic materials 0.000 description 1
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
• MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 238000009533 lab test Methods 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 229940072033 potash Drugs 0.000 description 1
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 238000005086 pumping Methods 0.000 description 1
• 230000000717 retained effect Effects 0.000 description 1
• 230000000630 rising effect Effects 0.000 description 1
• 238000004062 sedimentation Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
• 239000002966 varnish Substances 0.000 description 1