CN1269352A - 用丁烯低聚物制备乙烯酯的方法 - Google Patents
用丁烯低聚物制备乙烯酯的方法 Download PDFInfo
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- CN1269352A CN1269352A CN00108619A CN00108619A CN1269352A CN 1269352 A CN1269352 A CN 1269352A CN 00108619 A CN00108619 A CN 00108619A CN 00108619 A CN00108619 A CN 00108619A CN 1269352 A CN1269352 A CN 1269352A
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- Prior art keywords
- vinyl esters
- vinyl
- butene
- acid
- process according
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- 229920001567 vinyl ester resin Polymers 0.000 title claims abstract description 68
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 40
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 229920000642 polymer Polymers 0.000 title description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 47
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000004014 plasticizer Substances 0.000 claims abstract description 7
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- 150000001336 alkenes Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 8
- 230000003606 oligomerizing effect Effects 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000003751 zinc Chemical class 0.000 claims description 3
- 238000007037 hydroformylation reaction Methods 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 16
- -1 Vinyl esters Chemical class 0.000 description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
- 238000006384 oligomerization reaction Methods 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UPSVYNDQEVZTMB-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;1,3,5,7-tetranitro-1,3,5,7-tetrazocane Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O.[O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UPSVYNDQEVZTMB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FCWBXMTVLZGVEG-UHFFFAOYSA-N 2,2,4-trimethylhexanoic acid Chemical compound CCC(C)CC(C)(C)C(O)=O FCWBXMTVLZGVEG-UHFFFAOYSA-N 0.000 description 2
- WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical compound CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- CBQQWWYZSKCIRS-UHFFFAOYSA-N 2,2,3,3-tetramethylpentanoic acid Chemical compound CCC(C)(C)C(C)(C)C(O)=O CBQQWWYZSKCIRS-UHFFFAOYSA-N 0.000 description 1
- OJEWIWBDGBRNFP-UHFFFAOYSA-N 2,2,3-trimethylhexanoic acid Chemical compound CCCC(C)C(C)(C)C(O)=O OJEWIWBDGBRNFP-UHFFFAOYSA-N 0.000 description 1
- BROAOSNULRMVBL-UHFFFAOYSA-N 2,2,5-trimethylhexanoic acid Chemical compound CC(C)CCC(C)(C)C(O)=O BROAOSNULRMVBL-UHFFFAOYSA-N 0.000 description 1
- URGYOSLMFPSHMT-UHFFFAOYSA-N 2,2-diethyl-3-methylbutanoic acid Chemical compound CCC(CC)(C(C)C)C(O)=O URGYOSLMFPSHMT-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- QRMMMWOSHHVOCJ-UHFFFAOYSA-N 2,2-dimethylheptanoic acid Chemical compound CCCCCC(C)(C)C(O)=O QRMMMWOSHHVOCJ-UHFFFAOYSA-N 0.000 description 1
- OWEMTCOXFULTNW-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C)(C(C)C)C(O)=O OWEMTCOXFULTNW-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- SXJBHJCKWQIWHA-UHFFFAOYSA-N 2-ethyl-2,3,3-trimethylbutanoic acid Chemical compound CCC(C)(C(O)=O)C(C)(C)C SXJBHJCKWQIWHA-UHFFFAOYSA-N 0.000 description 1
- JRQAAPYJURVMJK-UHFFFAOYSA-N 2-ethyl-2,3-dimethylpentanoic acid Chemical compound CCC(C)C(C)(CC)C(O)=O JRQAAPYJURVMJK-UHFFFAOYSA-N 0.000 description 1
- MBHRUQBGWAJYDZ-UHFFFAOYSA-N 2-ethyl-2,4-dimethylpentanoic acid Chemical compound CCC(C)(C(O)=O)CC(C)C MBHRUQBGWAJYDZ-UHFFFAOYSA-N 0.000 description 1
- LYIMSMCQBKXQDK-UHFFFAOYSA-N 2-ethyl-2-methylhexanoic acid Chemical compound CCCCC(C)(CC)C(O)=O LYIMSMCQBKXQDK-UHFFFAOYSA-N 0.000 description 1
- JWZJWGCSMSGWPY-UHFFFAOYSA-N 2-methyl-2-propan-2-ylpentanoic acid Chemical compound CCCC(C)(C(C)C)C(O)=O JWZJWGCSMSGWPY-UHFFFAOYSA-N 0.000 description 1
- KTHXOYWHJBTQNC-UHFFFAOYSA-N 2-methyl-2-propylpentanoic acid Chemical compound CCCC(C)(C(O)=O)CCC KTHXOYWHJBTQNC-UHFFFAOYSA-N 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- OWWRMMIWAOBBFK-UHFFFAOYSA-N 3,4-dimethylhex-1-ene Chemical compound CCC(C)C(C)C=C OWWRMMIWAOBBFK-UHFFFAOYSA-N 0.000 description 1
- QDMFTFWKTYXBIW-UHFFFAOYSA-N 3-Methyl-1-heptene Chemical compound CCCCC(C)C=C QDMFTFWKTYXBIW-UHFFFAOYSA-N 0.000 description 1
- JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/02—Esters of monocarboxylic acids
- C08F18/04—Vinyl esters
- C08F18/10—Vinyl esters of monocarboxylic acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
羧酸的链长 | 直链乙烯酯 | 玻璃化点[℃] | 叔乙烯酯 | 玻璃化点[℃] |
C2-乙烯酯 | 乙酸乙烯酯 | +38(33)* | ||
C3-乙烯酯 | 丙酸乙烯酯 | -7(-7)* | ||
C4-乙烯酯 | 丁酸乙烯酯 | -5 | ||
C5-乙烯酯 | -15*** | 2,2-二甲基丙酸 | 86(70)* | |
C6-乙烯酯 | 己酸乙烯酯 | -20 | 2,2-二甲基丁酸 | 41** |
C10-乙烯酯 | 癸酸乙烯酯 | -60 | ||
C12-乙烯酯 | 月桂酸乙烯酯 | -75(-53)* |
叔C9-羧酸 | 玻璃化点[℃] |
2,3-二甲基-2-异丙基-丁酸 | 119 |
2-乙基-2,3,3-三甲基-丁酸 | 115 |
2,2,3,3-四甲基-戊酸 | 91 |
(Veo Va®9,Shell) | 70(60)* |
2,4,4-四甲基-戊酸 | 55 |
2,2,4-三甲基-己酸 | 10 |
实施例1 | 实施例2 | 实施例3 | |
烯烃A | 烯烃B | 烯烃C | |
正辛烯 | ~0% | ~6% | ~13% |
3-甲基-庚烯 | ~5% | ~59% | ~62% |
3,4-二甲基-己烯 | ~70% | ~34% | ~24% |
其他的C8-烯烃 | ~25% | ~1% | ~1% |
实施例4 | 实施例5 | 实施例6 | |
异构体C9-羧酸 | 酸A | 酸B | 酸C |
2,2-二甲基-庚酸 | 0.5% | 6.5% | 7.4% |
2-甲基-2-乙基-己酸 | 3.7% | 48.1% | 55.2% |
2-甲基-2-丙基-戊酸 | 0.5% | 6.3% | 7.2% |
2,2-二甲基-戊酸 | 0.2% | 3.0% | 3.5% |
2,2,5-三甲基-己酸 | 2.1% | 1.1% | 0.8% |
2,2,4-三甲基-己酸 | 2.0% | 1.0% | 0.8% |
2,4-二甲基-2-乙基-戊酸 | 4.4% | 2.2% | 1.6% |
2,2,3-三甲基-己酸 | 6.4% | 3.2% | 2.4% |
2-甲基-2-异丙基-戊酸 | 13.7% | 6.9% | 5.1% |
2,3-二甲基-2-乙基-戊酸 | 37.5% | 19.0% | 13.8% |
2-乙基-2-异丙基-丁酸 | 3.0% | 1.5% | 1.1% |
未知的其他酸 | 25.8% | 1.2% | 1.3% |
单体 | 重量份 |
C9-羧酸乙烯酯 | 100.00 |
水相 | |
VE水 | 70.00 |
阴离子表面活性剂,例如Marlon®A390(85%活性物流) | 0.03 |
非离子表面活性剂,例如Marlophen®820(25%溶液) | 8.00 |
过氧二硫酸钾(K2S2O8) | 0.10 |
碳酸钾 | 0.25 |
羟乙基纤维素,例如Natrosol250L(或LR) | 2.00 |
乙酸(100%) | 0.20 |
引发剂溶液 | |
过氧二硫酸钾 | 0.23 |
VE水 | 12.00 |
实施例10 | 实施例11 | 实施例12 | 实施例13 | 实施例14 | |
加入物 | (对比) | (对比) | 酸A | 酸B | 酸C |
玻璃化点 | -3℃ | ~+60℃ | ~+38℃ | +1℃ | -3℃ |
Claims (13)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19908320.7 | 1999-02-26 | ||
DE19908320A DE19908320A1 (de) | 1999-02-26 | 1999-02-26 | Verfahren zur Herstellung von Vinylestern aus Butenoligomeren |
Publications (2)
Publication Number | Publication Date |
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CN1269352A true CN1269352A (zh) | 2000-10-11 |
CN1185203C CN1185203C (zh) | 2005-01-19 |
Family
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CNB001086197A Expired - Fee Related CN1185203C (zh) | 1999-02-26 | 2000-02-25 | 用丁烯低聚物制备乙烯酯的方法 |
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Country | Link |
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US (1) | US6281372B1 (zh) |
EP (1) | EP1033360B1 (zh) |
JP (1) | JP4681095B2 (zh) |
KR (1) | KR100673279B1 (zh) |
CN (1) | CN1185203C (zh) |
AR (1) | AR022771A1 (zh) |
BR (1) | BR0000963A (zh) |
CA (1) | CA2299587A1 (zh) |
DE (2) | DE19908320A1 (zh) |
ES (1) | ES2204373T3 (zh) |
HK (1) | HK1031866A1 (zh) |
ID (1) | ID24863A (zh) |
MX (1) | MXPA00001956A (zh) |
MY (1) | MY121144A (zh) |
NO (1) | NO20000872L (zh) |
PL (1) | PL338630A1 (zh) |
SG (1) | SG82685A1 (zh) |
TW (1) | TW482760B (zh) |
ZA (1) | ZA200000927B (zh) |
Cited By (4)
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CN103459364A (zh) * | 2011-04-07 | 2013-12-18 | 迈图专业化学股份有限公司 | 生产α,α-支化羧酸乙烯基酯的方法 |
TWI464143B (zh) * | 2012-07-13 | 2014-12-11 | Oxea Gmbh | 從2-乙基己醇進行製造異壬酸羧酸酯之製法及其製品 |
CN104379543A (zh) * | 2012-07-13 | 2015-02-25 | Oxea有限责任公司 | 由2-乙基己醇生产异壬酸的方法 |
CN104411675A (zh) * | 2012-07-13 | 2015-03-11 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
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EP1281700A1 (en) | 2001-07-31 | 2003-02-05 | Resolution Research Nederland B.V. | Manufacturing process for the preparation of alpha, alpha-branched alkane carboxylic acids providing esters with an improved softness |
EP2447241A1 (en) | 2010-10-19 | 2012-05-02 | Momentive Specialty Chemicals Research Belgium | Glycidyl esters of alpha, alpha branched neononanoic acids, synthesis and uses |
PT2630113T (pt) | 2010-10-19 | 2020-03-03 | Momentive Specialty Chemicals Res S A | Ésteres de glicidilo de ácidos neononanóicos alfa, alfaramificados, síntese e utilizações |
EP2476672A1 (en) * | 2010-12-22 | 2012-07-18 | Momentive Specialty Chemicals Research Belgium S.A. | Glycidyl esters of alpha , alpha branched acids compositions |
EP2474537A1 (en) | 2010-12-22 | 2012-07-11 | Momentive Specialty Chemicals Research Belgium S.A. | glycidyl esters of alpha, alpha branched acids compositions |
WO2013056812A1 (en) | 2011-10-19 | 2013-04-25 | Momentive Specialty Chemicals Research Belgium Sa | Acrylic polyol resins compositions |
US20140287252A1 (en) | 2011-10-19 | 2014-09-25 | Momentive Specialty Chemicals Inc. | Polyester polyol resins compositions |
WO2013056814A2 (en) | 2011-10-19 | 2013-04-25 | Momentive Specialty Chemicals Research Beigium S.A. | Polyether polyol resins compositions |
BR112014009484A8 (pt) | 2011-10-19 | 2018-02-06 | Hexion Inc | Composição de resinas acrílicas com função hidroxila, processo para preparar uma composição, composição aglutinante, substrato de metal ou de plástico, poliol acrílico, resina de copolímero de poliol acrílico, e, composição de revestimento |
WO2013075806A2 (en) * | 2011-11-25 | 2013-05-30 | Momentive Specialty Chemicals Research Beigium Sa | Epoxy compositions |
WO2013075805A2 (en) | 2011-11-25 | 2013-05-30 | Momentive Specialty Chemicals Research Beigium S.A. | Epoxy compositions |
DE112014001071B4 (de) | 2013-03-15 | 2021-07-01 | Trane International Inc. | Vorrichtungen, Systeme und Verfahren für einen variablen Frequenzantriebbetrieb und eine entsprechende Steuerung |
DE102013009323B4 (de) | 2013-06-01 | 2018-09-20 | Oxea Gmbh | Verfahren zur Herstellung von Gemischen enthaltend tertiäre Isononansäuren ausgehend von 2-Ethylhexanol |
US9783709B2 (en) | 2013-10-10 | 2017-10-10 | Hexion Inc. | Process for the manufacture of α, α-branched carboxylic acid vinyl esters |
DE102014013123B4 (de) | 2014-08-30 | 2020-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Gemischen enthaltend tertiäre lsononansäuren ausgehend von 2-Ethylhexanol |
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DE972291C (de) * | 1954-05-16 | 1959-07-02 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Monocarbonsaeuren aus Olefinen, Kohlenoxyd und Wasser |
FR2195480A1 (en) | 1972-08-07 | 1974-03-08 | Toa Nenryo Kogyo Kk | Copper carbonyl catalyst solns - made by reacting a copper(1) cpd with carbon monoxide in the presence of boron trifluoride |
GB9102513D0 (en) * | 1991-02-06 | 1991-03-27 | Exxon Chemical Patents Inc | Hydrocarbon production |
WO1993022353A1 (en) * | 1992-05-06 | 1993-11-11 | Shell Internationale Research Maatschappij B.V. | Polymers and polymer latices from vinylesters of saturated monocarboxylic acids |
DE4339713A1 (de) * | 1993-11-22 | 1995-05-24 | Basf Ag | Verfahren zur Oligomerisierung von Olefinen zu hochlinearen Oligomeren und Katalysatoren dafür |
DE19629903A1 (de) * | 1996-07-24 | 1998-01-29 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Buten-Oligomeren aus Feldbutanen |
-
1999
- 1999-02-26 DE DE19908320A patent/DE19908320A1/de not_active Withdrawn
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2000
- 2000-02-22 NO NO20000872A patent/NO20000872L/no not_active Application Discontinuation
- 2000-02-23 EP EP00103784A patent/EP1033360B1/de not_active Expired - Lifetime
- 2000-02-23 ES ES00103784T patent/ES2204373T3/es not_active Expired - Lifetime
- 2000-02-23 DE DE50003683T patent/DE50003683D1/de not_active Expired - Lifetime
- 2000-02-24 MX MXPA00001956A patent/MXPA00001956A/es active IP Right Grant
- 2000-02-25 PL PL00338630A patent/PL338630A1/xx unknown
- 2000-02-25 AR ARP000100846A patent/AR022771A1/es active IP Right Grant
- 2000-02-25 SG SG200001047A patent/SG82685A1/en unknown
- 2000-02-25 MY MYPI20000723A patent/MY121144A/en unknown
- 2000-02-25 ZA ZA200000927A patent/ZA200000927B/xx unknown
- 2000-02-25 CN CNB001086197A patent/CN1185203C/zh not_active Expired - Fee Related
- 2000-02-25 JP JP2000049560A patent/JP4681095B2/ja not_active Expired - Fee Related
- 2000-02-25 TW TW089103521A patent/TW482760B/zh not_active IP Right Cessation
- 2000-02-25 KR KR1020000009301A patent/KR100673279B1/ko not_active IP Right Cessation
- 2000-02-25 CA CA002299587A patent/CA2299587A1/en not_active Abandoned
- 2000-02-28 BR BR0000963-6A patent/BR0000963A/pt not_active Application Discontinuation
- 2000-02-28 US US09/514,355 patent/US6281372B1/en not_active Expired - Lifetime
- 2000-02-28 ID IDP20000149D patent/ID24863A/id unknown
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103459364A (zh) * | 2011-04-07 | 2013-12-18 | 迈图专业化学股份有限公司 | 生产α,α-支化羧酸乙烯基酯的方法 |
TWI464143B (zh) * | 2012-07-13 | 2014-12-11 | Oxea Gmbh | 從2-乙基己醇進行製造異壬酸羧酸酯之製法及其製品 |
CN104379543A (zh) * | 2012-07-13 | 2015-02-25 | Oxea有限责任公司 | 由2-乙基己醇生产异壬酸的方法 |
CN104411675A (zh) * | 2012-07-13 | 2015-03-11 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
CN104411675B (zh) * | 2012-07-13 | 2016-10-12 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
CN104379543B (zh) * | 2012-07-13 | 2016-10-19 | Oxea有限责任公司 | 由2-乙基己醇生产异壬酸的方法 |
Also Published As
Publication number | Publication date |
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US6281372B1 (en) | 2001-08-28 |
DE50003683D1 (de) | 2003-10-23 |
CN1185203C (zh) | 2005-01-19 |
EP1033360A1 (de) | 2000-09-06 |
CA2299587A1 (en) | 2000-08-26 |
BR0000963A (pt) | 2000-09-19 |
NO20000872D0 (no) | 2000-02-22 |
ZA200000927B (en) | 2000-10-16 |
JP4681095B2 (ja) | 2011-05-11 |
ID24863A (id) | 2000-08-31 |
ES2204373T3 (es) | 2004-05-01 |
MXPA00001956A (es) | 2002-03-08 |
MY121144A (en) | 2005-12-30 |
SG82685A1 (en) | 2001-08-21 |
NO20000872L (no) | 2000-08-28 |
PL338630A1 (en) | 2000-08-28 |
DE19908320A1 (de) | 2000-08-31 |
KR100673279B1 (ko) | 2007-01-24 |
TW482760B (en) | 2002-04-11 |
KR20000058191A (ko) | 2000-09-25 |
JP2000248017A (ja) | 2000-09-12 |
HK1031866A1 (en) | 2001-06-29 |
EP1033360B1 (de) | 2003-09-17 |
AR022771A1 (es) | 2002-09-04 |
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