SG193629A1 - Synthesis of diacids - Google Patents
Synthesis of diacids Download PDFInfo
- Publication number
- SG193629A1 SG193629A1 SG2013072400A SG2013072400A SG193629A1 SG 193629 A1 SG193629 A1 SG 193629A1 SG 2013072400 A SG2013072400 A SG 2013072400A SG 2013072400 A SG2013072400 A SG 2013072400A SG 193629 A1 SG193629 A1 SG 193629A1
- Authority
- SG
- Singapore
- Prior art keywords
- acid
- catalyst system
- lactone
- catalyst
- unreacted
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 165
- 239000002253 acid Substances 0.000 claims abstract description 123
- 150000002596 lactones Chemical class 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 59
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000010438 heat treatment Methods 0.000 claims abstract description 28
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 146
- 238000000034 method Methods 0.000 claims description 103
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 80
- 239000001361 adipic acid Substances 0.000 claims description 75
- 235000011037 adipic acid Nutrition 0.000 claims description 73
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims description 59
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 53
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 48
- 229910052763 palladium Inorganic materials 0.000 claims description 43
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical group CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 28
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 27
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 22
- 238000004064 recycling Methods 0.000 claims description 22
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims description 20
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 18
- 150000002941 palladium compounds Chemical class 0.000 claims description 18
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 17
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 16
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims description 12
- 238000000066 reactive distillation Methods 0.000 claims description 12
- 239000010457 zeolite Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 235000011149 sulphuric acid Nutrition 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 229910021536 Zeolite Inorganic materials 0.000 claims description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 9
- 229940040102 levulinic acid Drugs 0.000 claims description 9
- 239000001117 sulphuric acid Substances 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004927 clay Substances 0.000 claims description 7
- DSYQHWPNJZFRCU-UHFFFAOYSA-N 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane Chemical group C1C(P2)(C)OC3(C)CC2(C)OC1(C)O3 DSYQHWPNJZFRCU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 238000005336 cracking Methods 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 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 claims description 3
- 239000011949 solid catalyst Substances 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 239000002815 homogeneous catalyst Substances 0.000 claims description 2
- 229960000250 adipic acid Drugs 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000007789 gas Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 230000006315 carbonylation Effects 0.000 description 9
- 238000005810 carbonylation reaction Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- -1 palladium carboxylates Chemical class 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- SFCNPIUDAIFHRD-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=CC=C1CP(C(C)(C)C)C(C)(C)C SFCNPIUDAIFHRD-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- YLPLXQAQRQCWME-UHFFFAOYSA-N C(C(CC)C(=O)O)C(=O)O.C(CCCCC(=O)O)(=O)O Chemical compound C(C(CC)C(=O)O)C(=O)O.C(CCCCC(=O)O)(=O)O YLPLXQAQRQCWME-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- YIYBQIKDCADOSF-ARJAWSKDSA-N cis-pent-2-enoic acid Chemical compound CC\C=C/C(O)=O YIYBQIKDCADOSF-ARJAWSKDSA-N 0.000 description 1
- UIUWNILCHFBLEQ-IHWYPQMZSA-N cis-pent-3-enoic acid Chemical compound C\C=C/CC(O)=O UIUWNILCHFBLEQ-IHWYPQMZSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010586 diagram Methods 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
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000007518 monoprotic acids Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- ZAIULUYKQLVQFH-UHFFFAOYSA-N n'-(2-aminophenyl)-n-phenylheptanediamide Chemical compound NC1=CC=CC=C1NC(=O)CCCCCC(=O)NC1=CC=CC=C1 ZAIULUYKQLVQFH-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000007519 polyprotic acids Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-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
- C07D307/30—Heterocyclic compounds containing five-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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- C08G69/28—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H8/00—Macromolecular compounds derived from lignocellulosic materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyamides (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161468494P | 2011-03-28 | 2011-03-28 | |
| PCT/SG2012/000107 WO2012134397A1 (en) | 2011-03-28 | 2012-03-28 | Synthesis of diacids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG193629A1 true SG193629A1 (en) | 2013-11-29 |
Family
ID=46931753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2013072400A SG193629A1 (en) | 2011-03-28 | 2012-03-28 | Synthesis of diacids |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20150183703A1 (https=) |
| EP (1) | EP2691361A4 (https=) |
| JP (2) | JP2014519476A (https=) |
| SG (1) | SG193629A1 (https=) |
| WO (1) | WO2012134397A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105102413B (zh) * | 2013-01-18 | 2017-03-08 | 帝斯曼知识产权资产管理有限公司 | 制备甲酰戊酸和己二酸的方法 |
| WO2017135898A1 (en) * | 2016-02-02 | 2017-08-10 | Agency For Science, Technology And Research | Process for preparing mono and dicarboxylic acids |
| WO2017135897A1 (en) * | 2016-02-02 | 2017-08-10 | Agency For Science, Technology And Research | A catalyst for the carbonylation of alkenes |
| JP6997459B2 (ja) * | 2016-03-21 | 2022-02-04 | ノボマー， インコーポレイテッド | 改良されたアクリル酸製造プロセス |
| US20180305286A1 (en) | 2016-03-21 | 2018-10-25 | Novomer, Inc. | Systems and Processes for Producing Organic Acids Direct from Beta-Lactones |
| US20180282251A1 (en) * | 2017-03-21 | 2018-10-04 | Novomer, Inc. | Systems and processes for producing organic acids direct from beta-lactones |
| MX2021001229A (es) * | 2018-08-01 | 2021-06-23 | Braskem America Inc | Composiciones termoplásticas que tienen resistencia mejorada, artículos hechos a partir de las mismas y métodos de uso de las mismas. |
| CN111979819B (zh) * | 2020-08-10 | 2022-08-09 | 齐鲁工业大学 | 分离木质纤维生物质组分的方法 |
| EP4306515B1 (en) * | 2021-03-12 | 2026-02-04 | Toray Industries, Inc. | 3-hydroxyadipic acid 3,6-lactone composition |
| JP7755360B2 (ja) * | 2023-08-04 | 2025-10-16 | 国立研究開発法人農業・食品産業技術総合研究機構 | 植物病原菌の生育を抑制するための組成物及び方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2130948A (en) * | 1937-04-09 | 1938-09-20 | Du Pont | Synthetic fiber |
| JPS59116247A (ja) * | 1982-12-23 | 1984-07-05 | Soda Koryo Kk | 不飽和脂肪酸の製法 |
| US4788333A (en) * | 1985-01-07 | 1988-11-29 | E. I. Du Pont De Nemours And Company | Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids |
| US4897497A (en) * | 1988-04-26 | 1990-01-30 | Biofine Incorporated | Lignocellulose degradation to furfural and levulinic acid |
| JPH026427A (ja) * | 1988-06-27 | 1990-01-10 | Idemitsu Kosan Co Ltd | ジカルボン酸およびホルミルカルボン酸の製造方法 |
| FR2693459B1 (fr) * | 1992-07-09 | 1994-08-26 | Rhone Poulenc Chimie | Procédé de préparation de l'acide adipique par hydrocarboxylation d'acides penténoïques. |
| SK41895A3 (en) * | 1992-10-02 | 1995-09-13 | Rhone Poulenc Chimie | Process for isomerization of lactones into pentenoic acids by acid or basic catalysis |
| FR2749300B1 (fr) * | 1996-06-04 | 1998-07-17 | Rhone Poulenc Fibres | Procede de purification de l'acide adipique par cristallisation |
| FR2749582B1 (fr) * | 1996-06-07 | 1998-07-17 | Rhone Poulenc Fibres | Procede d'hydroxycarbonylation des acides pentenoiques |
| US5710325A (en) * | 1996-11-01 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Manufacture of adipic acid |
| US7348454B2 (en) * | 2003-05-22 | 2008-03-25 | Shell Oil Company | Process for the hydrocarboxylation of ethylenically unsaturated carboxylic acids |
| CA2549458A1 (en) * | 2003-12-15 | 2005-06-30 | Shell Internationale Research Maatschappij B.V. | A process for the liquefaction of lignocellulosic material |
| WO2006125801A1 (en) * | 2005-05-27 | 2006-11-30 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of adipic acid from n-pentenoic acid |
-
2012
- 2012-03-28 WO PCT/SG2012/000107 patent/WO2012134397A1/en not_active Ceased
- 2012-03-28 US US14/007,169 patent/US20150183703A1/en not_active Abandoned
- 2012-03-28 SG SG2013072400A patent/SG193629A1/en unknown
- 2012-03-28 JP JP2014502512A patent/JP2014519476A/ja active Pending
- 2012-03-28 EP EP12764925.9A patent/EP2691361A4/en not_active Withdrawn
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2016
- 2016-10-20 JP JP2016205882A patent/JP2017057204A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012134397A1 (en) | 2012-10-04 |
| JP2017057204A (ja) | 2017-03-23 |
| EP2691361A1 (en) | 2014-02-05 |
| US20150183703A1 (en) | 2015-07-02 |
| EP2691361A4 (en) | 2014-09-17 |
| JP2014519476A (ja) | 2014-08-14 |
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