CA2791500C - A process for preparing an adipic acid composition - Google Patents
A process for preparing an adipic acid composition Download PDFInfo
- Publication number
- CA2791500C CA2791500C CA2791500A CA2791500A CA2791500C CA 2791500 C CA2791500 C CA 2791500C CA 2791500 A CA2791500 A CA 2791500A CA 2791500 A CA2791500 A CA 2791500A CA 2791500 C CA2791500 C CA 2791500C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- adipic acid
- catalyst
- hydrogen
- compositions
- 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.)
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 239000001361 adipic acid Substances 0.000 title claims abstract description 62
- 235000011037 adipic acid Nutrition 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000000047 product Substances 0.000 claims abstract description 34
- 239000000758 substrate Substances 0.000 claims abstract description 27
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000008103 glucose Substances 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052737 gold Inorganic materials 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000004423 acyloxy group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- -1 ammonium ions Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000377 silicon dioxide Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 239000000470 constituent Substances 0.000 description 19
- 229960001031 glucose Drugs 0.000 description 19
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 18
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000007792 addition Methods 0.000 description 13
- 239000002243 precursor Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 7
- 239000010779 crude oil Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000005470 impregnation Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229910052703 rhodium Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- QRFNDAVXJCGLFB-GJPGBQJBSA-N (3r,3ar,6s,6ar)-3,6-dihydroxy-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione Chemical compound O1C(=O)[C@H](O)[C@H]2OC(=O)[C@@H](O)[C@H]21 QRFNDAVXJCGLFB-GJPGBQJBSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920002302 Nylon 6,6 Polymers 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 229910018967 Pt—Rh Inorganic materials 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052702 rhenium Inorganic materials 0.000 description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LSIXBBPOJBJQHN-UHFFFAOYSA-N 2,3-Dimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1C2 LSIXBBPOJBJQHN-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000010364 biochemical engineering Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229940077731 carbohydrate nutrients Drugs 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- XECPAIJNBXCOBO-XHGCLVTGSA-N (2r)-2-[(2s,3r,4s)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O XECPAIJNBXCOBO-XHGCLVTGSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- IUQNAGFJAIOCNL-UHFFFAOYSA-N 2,3,4-trihydroxy-5-oxohexanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)C(=O)C(O)=O IUQNAGFJAIOCNL-UHFFFAOYSA-N 0.000 description 1
- DMCRIWYMGHUFJK-UHFFFAOYSA-N 2,3,5-trihydroxy-4-oxohexanedioic acid Chemical compound OC(=O)C(O)C(O)C(=O)C(O)C(O)=O DMCRIWYMGHUFJK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XECPAIJNBXCOBO-MMPJQOAZSA-N D-glucaro-1,4-lactone Chemical compound OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O XECPAIJNBXCOBO-MMPJQOAZSA-N 0.000 description 1
- 241000748691 Furia Species 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000002210 biocatalytic effect Effects 0.000 description 1
- 229940095625 calcium glucarate Drugs 0.000 description 1
- UGZVNIRNPPEDHM-SBBOJQDXSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical compound [Ca+2].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O UGZVNIRNPPEDHM-SBBOJQDXSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000010791 domestic waste Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(II) nitrate Inorganic materials [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
-
- 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
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
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- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31119010P | 2010-03-05 | 2010-03-05 | |
| US61/311,190 | 2010-03-05 | ||
| US12/814,188 US8669397B2 (en) | 2009-06-13 | 2010-06-11 | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US12/814,188 | 2010-06-11 | ||
| PCT/US2010/060147 WO2011109051A1 (en) | 2010-03-05 | 2010-12-13 | Adipic acid composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2791500A1 CA2791500A1 (en) | 2011-09-09 |
| CA2791500C true CA2791500C (en) | 2021-11-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2791500A Active CA2791500C (en) | 2010-03-05 | 2010-12-13 | A process for preparing an adipic acid composition |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2542519A1 (zh) |
| CN (2) | CN102869642A (zh) |
| AU (1) | AU2010347225B2 (zh) |
| BR (1) | BR112012022136B1 (zh) |
| CA (1) | CA2791500C (zh) |
| NZ (1) | NZ601945A (zh) |
| WO (1) | WO2011109051A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104169259B (zh) * | 2012-02-23 | 2016-09-21 | 莱诺维亚公司 | 从己二酸产生己内酰胺 |
| DE102012006946A1 (de) | 2012-04-10 | 2013-10-10 | Stratley Ag | Verfahren zur Herstellung von Caprolactam |
| EP2849884B1 (en) | 2012-05-15 | 2020-09-09 | Archer-Daniels-Midland Company | Reduction catalysts |
| CN107556186B (zh) * | 2017-10-17 | 2019-06-18 | 北京大学 | 一种由葡萄糖二酸制备己二酸的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472168A (en) * | 1948-10-12 | 1949-06-07 | Charles L Mehltretter | Process for the preparation of d-glucosaccharic acid |
| DE1916601C3 (de) | 1969-04-01 | 1975-01-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Adipinsäuredinitril |
| US3917707A (en) | 1974-07-31 | 1975-11-04 | Du Pont | Suppression of 1,2-diaminocyclohexane formation during production of hexamethylenediamine |
| US4400468A (en) | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
| US4722997A (en) | 1985-05-31 | 1988-02-02 | Stamicarbon, B.V. | Process for the preparation of nylon 4,6 |
| DE3643011A1 (de) | 1986-12-17 | 1988-06-30 | Basf Ag | Verfahren zur herstellung von caprolactam aus 6-aminocapronsaeure, deren estern und amiden |
| US5487987A (en) | 1993-09-16 | 1996-01-30 | Purdue Research Foundation | Synthesis of adipic acid from biomass-derived carbon sources |
| DE19548289A1 (de) | 1995-12-22 | 1997-06-26 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von Caprolactam und Hexamethylendiamin |
| US6008418A (en) | 1996-03-01 | 1999-12-28 | Basf Aktiengesellschaft | Process for preparing 1,6 hexanediol with a level of purity over 99% |
| US5900511A (en) | 1997-03-28 | 1999-05-04 | E. I. De Pont De Nemours And Company | Process for continuous hydrogenation of adiponitrile |
| US5986127A (en) | 1999-03-15 | 1999-11-16 | E. I. Du Pont De Nemours And Company | Aminonitrile production |
| DE19839338A1 (de) | 1998-08-28 | 2000-03-02 | Basf Ag | Verbessertes Verfahren zur gleizeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin |
| FR2785608B1 (fr) | 1998-11-05 | 2000-12-29 | Rhone Poulenc Fibres | Procede d'hemihydrogenation de dinitriles |
| US6087296A (en) | 1998-11-05 | 2000-07-11 | E. I. Du Pont De Nemours & Co. | Raney iron catalyst and a process for hydrogenating organic compounds using said catalyst |
| US6569802B1 (en) | 1999-11-30 | 2003-05-27 | E. I. Du Pont De Nemours And Company | Catalyst for selective hydrogenation of dinitriles |
| US20020111458A1 (en) * | 2000-12-01 | 2002-08-15 | Masato Minami | Method for producing aliphatic polyester |
| CN1313431C (zh) * | 2004-11-26 | 2007-05-02 | 天津大学 | 环己烷氧化液酸洗水硝酸氧化制备无金属离子己二酸方法 |
| CN100537511C (zh) * | 2006-08-30 | 2009-09-09 | 中国石油天然气股份有限公司 | 连续酯化生产己二酸二甲酯的方法及设备 |
-
2010
- 2010-12-13 CN CN2010800651905A patent/CN102869642A/zh active Pending
- 2010-12-13 WO PCT/US2010/060147 patent/WO2011109051A1/en active Application Filing
- 2010-12-13 AU AU2010347225A patent/AU2010347225B2/en not_active Ceased
- 2010-12-13 CN CN201910397901.1A patent/CN110078614A/zh active Pending
- 2010-12-13 BR BR112012022136A patent/BR112012022136B1/pt active IP Right Grant
- 2010-12-13 NZ NZ601945A patent/NZ601945A/en not_active IP Right Cessation
- 2010-12-13 CA CA2791500A patent/CA2791500C/en active Active
- 2010-12-13 EP EP10812827A patent/EP2542519A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN110078614A (zh) | 2019-08-02 |
| NZ601945A (en) | 2014-08-29 |
| CA2791500A1 (en) | 2011-09-09 |
| BR112012022136A2 (pt) | 2016-10-25 |
| WO2011109051A1 (en) | 2011-09-09 |
| AU2010347225A1 (en) | 2012-09-20 |
| CN102869642A (zh) | 2013-01-09 |
| AU2010347225B2 (en) | 2016-04-21 |
| BR112012022136B1 (pt) | 2018-10-09 |
| EP2542519A1 (en) | 2013-01-09 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20151203 |