KR20170134374A - 연속 카보닐화 방법 - Google Patents
연속 카보닐화 방법 Download PDFInfo
- Publication number
- KR20170134374A KR20170134374A KR1020177025875A KR20177025875A KR20170134374A KR 20170134374 A KR20170134374 A KR 20170134374A KR 1020177025875 A KR1020177025875 A KR 1020177025875A KR 20177025875 A KR20177025875 A KR 20177025875A KR 20170134374 A KR20170134374 A KR 20170134374A
- Authority
- KR
- South Korea
- Prior art keywords
- lewis acid
- carbonylation
- reaction vessel
- catalyst
- metal carbonyl
- 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.)
- Withdrawn
Links
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 316
- 238000000034 method Methods 0.000 title claims abstract description 166
- 230000006315 carbonylation Effects 0.000 title claims abstract description 106
- 230000008569 process Effects 0.000 title claims description 83
- 239000003054 catalyst Substances 0.000 claims abstract description 260
- 150000002596 lactones Chemical class 0.000 claims abstract description 44
- 229910052751 metal Inorganic materials 0.000 claims description 328
- 239000002184 metal Substances 0.000 claims description 327
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 217
- 239000002841 Lewis acid Substances 0.000 claims description 189
- 150000007517 lewis acids Chemical class 0.000 claims description 185
- 239000002243 precursor Substances 0.000 claims description 93
- 239000003446 ligand Substances 0.000 claims description 74
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 48
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 48
- 230000007935 neutral effect Effects 0.000 claims description 48
- 125000001931 aliphatic group Chemical group 0.000 claims description 44
- 238000000354 decomposition reaction Methods 0.000 claims description 37
- 239000012528 membrane Substances 0.000 claims description 13
- 238000001728 nano-filtration Methods 0.000 claims description 13
- 150000002924 oxiranes Chemical class 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 8
- 239000013626 chemical specie Substances 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 abstract description 97
- 238000012544 monitoring process Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 90
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 65
- -1 hydroxylmethyl group Chemical group 0.000 description 56
- 125000004429 atom Chemical group 0.000 description 51
- 150000001728 carbonyl compounds Chemical class 0.000 description 43
- 125000004432 carbon atom Chemical group C* 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 33
- 229910052760 oxygen Inorganic materials 0.000 description 33
- 239000001301 oxygen Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 125000005842 heteroatom Chemical group 0.000 description 31
- 238000007792 addition Methods 0.000 description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 28
- 229910052717 sulfur Inorganic materials 0.000 description 28
- 239000011593 sulfur Substances 0.000 description 28
- 125000000129 anionic group Chemical group 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 27
- 125000000623 heterocyclic group Chemical group 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 24
- 241000894007 species Species 0.000 description 22
- 239000011651 chromium Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 239000007857 degradation product Substances 0.000 description 15
- 239000007789 gas Substances 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000010936 titanium Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 238000011065 in-situ storage Methods 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 229920002125 Sokalan® Polymers 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 230000000737 periodic effect Effects 0.000 description 9
- 239000010948 rhodium Substances 0.000 description 9
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000010949 copper Chemical group 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229940014800 succinic anhydride Drugs 0.000 description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000001639 boron compounds Chemical class 0.000 description 7
- 229910052804 chromium Inorganic materials 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000003180 beta-lactone group Chemical group 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 235000019256 formaldehyde Nutrition 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical class OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 210000002706 plastid Anatomy 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229960000380 propiolactone Drugs 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000004435 EPR spectroscopy Methods 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229920000140 heteropolymer Polymers 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001145 hydrido group Chemical group *[H] 0.000 description 3
- 150000002500 ions Chemical group 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000000466 oxiranyl group Chemical group 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229910052802 copper Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Chemical group 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- AQZRARFZZMGLHL-UHFFFAOYSA-N 2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1CO1 AQZRARFZZMGLHL-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- NAORGNSYBDQEPT-UHFFFAOYSA-N 3-phenylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1.OC(=O)C=CC1=CC=CC=C1 NAORGNSYBDQEPT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BWRRWBIBNBVHQF-UHFFFAOYSA-N 4-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)butanoic acid Chemical compound O1C(CCCC(=O)O)=NC(C=2N=CC=CC=2)=N1 BWRRWBIBNBVHQF-UHFFFAOYSA-N 0.000 description 1
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010021639 Incontinence Diseases 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- RYQWRHUSMUEYST-UHFFFAOYSA-N [14]annulene Chemical compound C1=CC=CC=CC=CC=CC=CC=C1 RYQWRHUSMUEYST-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002065 inelastic X-ray scattering Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- UMRZSTCPUPJPOJ-UHFFFAOYSA-N norbornane Chemical compound C1CC2CCC1C2 UMRZSTCPUPJPOJ-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/37—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by reaction of ethers with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562116089P | 2015-02-13 | 2015-02-13 | |
| US62/116,089 | 2015-02-13 | ||
| PCT/US2016/017875 WO2016130998A1 (en) | 2015-02-13 | 2016-02-12 | Continuous carbonylation processes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20170134374A true KR20170134374A (ko) | 2017-12-06 |
Family
ID=56614998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177025875A Withdrawn KR20170134374A (ko) | 2015-02-13 | 2016-02-12 | 연속 카보닐화 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US10221150B2 (enExample) |
| EP (2) | EP3256441B1 (enExample) |
| JP (3) | JP7053264B2 (enExample) |
| KR (1) | KR20170134374A (enExample) |
| CN (1) | CN107428656B (enExample) |
| AU (1) | AU2016218996A1 (enExample) |
| CA (1) | CA2976253A1 (enExample) |
| HK (1) | HK1245761A1 (enExample) |
| MX (1) | MX2017010408A (enExample) |
| SA (1) | SA517382089B1 (enExample) |
| WO (1) | WO2016130998A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019143220A1 (ko) * | 2018-01-22 | 2019-07-25 | 국민대학교 산학협력단 | 전이금속 기반 비균질계 카보닐화 반응촉매 및 이를 이용한 락톤 또는 숙신산 무수물의 제조방법 |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103649038A (zh) | 2011-05-13 | 2014-03-19 | 诺沃梅尔公司 | 催化羰基化催化剂和方法 |
| WO2013063191A1 (en) | 2011-10-26 | 2013-05-02 | Novomer, Inc. | Process for production of acrylates from epoxides |
| JP2017506286A (ja) | 2013-12-07 | 2017-03-02 | ノボマー, インコーポレイテッド | ナノろ過膜および使用の方法 |
| EP3140292B1 (en) | 2014-05-05 | 2021-02-24 | Novomer, Inc. | Catalyst recycle methods |
| WO2015184289A1 (en) | 2014-05-30 | 2015-12-03 | Novomer Inc. | Integrated methods for chemical synthesis |
| JP6670011B2 (ja) | 2014-07-25 | 2020-03-18 | ノボマー, インコーポレイテッド | 金属錯体の合成およびその使用 |
| MA41507A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production de polymères |
| EP3256510B1 (en) | 2015-02-13 | 2020-12-09 | Novomer, Inc. | Process and system for production of polypropiolactone |
| MA41514A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédés intégrés de synthèse chimique |
| MA41513A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de distillation pour la production d'acide acrylique |
| US20180029005A1 (en) | 2015-02-13 | 2018-02-01 | Novomer, Inc. | Flexible chemical production platform |
| EP3256441B1 (en) | 2015-02-13 | 2020-04-08 | Novomer, Inc. | Continuous carbonylation processes |
| MA41508A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production d'acide polyacrylique |
| MA41510A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| BR112018002143A2 (pt) | 2015-07-31 | 2018-09-18 | Novomer Inc | sistema de produção/processo de produção para ácido acrílico e precursores do mesmo |
| US20180305286A1 (en) | 2016-03-21 | 2018-10-25 | Novomer, Inc. | Systems and Processes for Producing Organic Acids Direct from Beta-Lactones |
| AU2017236914A1 (en) | 2016-03-21 | 2018-11-08 | Novomer, Inc. | Improved acrylic acid production process |
| CN108884009A (zh) | 2016-03-21 | 2018-11-23 | 诺沃梅尔公司 | 制造超吸收性聚合物的系统和方法 |
| MA46720A (fr) | 2016-11-02 | 2019-09-11 | Novomer Inc | Polymères absorbants, procédés et systèmes de production et utilisations correspondantes |
| US10144802B2 (en) | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US10500104B2 (en) | 2016-12-06 | 2019-12-10 | Novomer, Inc. | Biodegradable sanitary articles with higher biobased content |
| KR102303686B1 (ko) * | 2017-02-28 | 2021-09-17 | 샌트랄 글래스 컴퍼니 리미티드 | 드라이 에칭제, 드라이 에칭 방법 및 반도체 장치의 제조방법 |
| US10065914B1 (en) | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10676426B2 (en) | 2017-06-30 | 2020-06-09 | Novomer, Inc. | Acrylonitrile derivatives from epoxide and carbon monoxide reagents |
| US10590099B1 (en) | 2017-08-10 | 2020-03-17 | Novomer, Inc. | Processes for producing beta-lactone with heterogenous catalysts |
| TW202000723A (zh) | 2018-06-14 | 2020-01-01 | 美商諾沃梅爾公司 | 透過封端劑封端以穩定聚丙內酯 |
| JP7676023B2 (ja) | 2018-07-13 | 2025-05-14 | ノボマー, インコーポレイテッド | ポリラクトン発泡体及びその製造方法 |
| US11498894B2 (en) | 2019-03-08 | 2022-11-15 | Novomer, Inc. | Integrated methods and systems for producing amide and nitrile compounds |
| US11401251B2 (en) * | 2019-03-18 | 2022-08-02 | Novomer, Inc. | Membrane separation system, and uses thereof |
| CN114144404B (zh) | 2019-08-01 | 2024-09-06 | 埃克森美孚技术与工程公司 | 制备取代的内酯的方法和系统 |
| WO2021252607A1 (en) | 2020-06-12 | 2021-12-16 | Novomer, Inc. | Beta-propiolactone compounds and ring opened beta-propiolactone compounds and uses for same |
| CN114409541A (zh) * | 2020-10-28 | 2022-04-29 | 上海浦景化工技术股份有限公司 | 一种乙烯羰基化制丙酸酯类的系统 |
| WO2022187010A1 (en) * | 2021-03-02 | 2022-09-09 | Novomer, Inc. | Process for the recovery and/or regeneration of catalyst components |
| CN114656426B (zh) * | 2021-12-13 | 2023-02-10 | 上海中化科技有限公司 | 一种环氧化合物连续羰基化制备β-内酯的方法 |
| CN115007222B (zh) * | 2022-07-15 | 2024-07-05 | 宁波天研精开技术有限公司 | 一种液相法生产碳酸二甲酯的铜基催化剂在线再生方法及装置 |
| CN115785030A (zh) * | 2022-12-19 | 2023-03-14 | 上海中化科技有限公司 | 一种环氧化合物高效制备β-内酯的方法 |
| WO2024259296A1 (en) | 2023-06-16 | 2024-12-19 | Novomer, Inc. | Synthesis of carbonylation catalyst from cobalt salts |
| WO2024259298A1 (en) | 2023-06-16 | 2024-12-19 | Novomer, Inc. | Synthesis of carbonylation catalyst using an alkylaluminum reduction |
| CN117658953A (zh) * | 2023-12-04 | 2024-03-08 | 上海中化科技有限公司 | 手性环氧化合物、手性β-内酯及聚羟基脂肪酸酯的制备方法 |
Family Cites Families (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2302321A (en) | 1942-11-17 | Process for the production of the | ||
| US2245404A (en) | 1939-02-03 | 1941-06-10 | Solvay Process Co | Manufacture of succinic anhydride |
| US2469704A (en) | 1946-04-06 | 1949-05-10 | Eastman Kodak Co | Continuous process of producing beta lactones at reduced pressure |
| US2526554A (en) | 1947-07-28 | 1950-10-17 | Goodrich Co B F | Preparation of beta-hydroxy carboxylic acid esters by alcoholysis of linear polyesters derived from beta-lactones |
| GB762138A (en) | 1953-05-07 | 1956-11-21 | Pechiney Prod Chimiques Sa | Improvements in or relating to processes for the preparation of hydracrylic esters |
| US3002017A (en) | 1959-07-13 | 1961-09-26 | Goodrich Co B F | Method for preparing acrylic acid |
| US3326938A (en) | 1962-11-09 | 1967-06-20 | Du Pont | Beta-lactone production |
| US3418338A (en) | 1966-02-28 | 1968-12-24 | Halcon International Inc | Water extractive distillation of an ethylene oxide stream containing formaldehyde |
| US3800006A (en) | 1968-05-25 | 1974-03-26 | Denki Onkyo Co Ltd | Graft polymers from vinyl compounds with beta-propiolactone, epsilon-caprolactone and ethylene oxide |
| NL7002062A (enExample) | 1970-02-13 | 1970-04-22 | ||
| US4026967A (en) | 1976-06-25 | 1977-05-31 | E. I. Du Pont De Nemours And Company | Process for making grafted polymeric material |
| US4081253A (en) | 1976-12-10 | 1978-03-28 | Texaco Development Corporation | Production of purified synthesis gas and carbon monoxide |
| US4221727A (en) | 1979-08-17 | 1980-09-09 | The Dow Chemical Company | Ethylene oxide recovery |
| JPS5714596A (en) | 1980-06-30 | 1982-01-25 | Denki Kagaku Kogyo Kk | Accelerating method of disproportionation |
| US4590293A (en) | 1982-01-18 | 1986-05-20 | Ashland Oil, Inc. | Process and apparatus for further processing of pressurized exothermic reactions |
| US5198578A (en) | 1986-07-17 | 1993-03-30 | Union Carbide Chemicals | Anhydrous diluents for the propylene oxidation reaction to acrolein and acrolein oxidation to acrylic acid |
| US4873378A (en) | 1986-08-20 | 1989-10-10 | Hoechst Celanese Corporation | Process for making 1,3-diols from epoxides |
| CA1339317C (en) | 1988-07-25 | 1997-08-19 | Ann Marie Lauritzen | Process for producing ethylene oxide |
| CA2034971A1 (en) | 1990-02-05 | 1991-08-06 | Eit Drent | Carbonylation catalyst system |
| US5096470A (en) | 1990-12-05 | 1992-03-17 | The Boc Group, Inc. | Hydrogen and carbon monoxide production by hydrocarbon steam reforming and pressure swing adsorption purification |
| FR2736912B1 (fr) | 1995-07-18 | 1997-08-22 | Atochem Elf Sa | Procede de purification de l'acide acrylique obtenu par oxydation catalytique du propylene |
| EP0920407B1 (en) | 1995-10-27 | 2002-12-11 | Hoechst Celanese Corporation | Process for improving productivity of a carbonylation catalyst solution by removing corrosion metals |
| DE19542829A1 (de) | 1995-11-17 | 1997-05-22 | Basf Ag | Verfahren zur Destillation von Ethylenoxid |
| IT1298535B1 (it) | 1998-02-02 | 2000-01-12 | Lonza Spa | Procedimento per la produzione di gamma-butirrolattone |
| US6147126A (en) | 1998-02-10 | 2000-11-14 | Exxon Research And Engineering Company | Gas conversion using hydrogen from syngas gas and hydroconversion tail gas |
| DE19829477A1 (de) | 1998-07-01 | 2000-01-05 | Basf Ag | Verfahren zur Reinigung von Acrylsäure oder Methacrylsäure durch Kristallisation und Destillation |
| KR100282039B1 (ko) | 1999-03-09 | 2001-02-15 | 윤종용 | 에폭사이드 유도체의 카르보닐화 방법 |
| US6392078B1 (en) | 2000-06-12 | 2002-05-21 | Catalytic Distillation Technologies | Process and catalyst for making dialkyl carbonates |
| JP2004505120A (ja) | 2000-07-28 | 2004-02-19 | ダウ グローバル テクノロジーズ インコーポレイティド | スルホン化した実質的にランダムなインターポリマーをベースとした吸収性材料 |
| US6573340B1 (en) | 2000-08-23 | 2003-06-03 | Biotec Biologische Naturverpackungen Gmbh & Co. Kg | Biodegradable polymer films and sheets suitable for use as laminate coatings as well as wraps and other packaging materials |
| US6773578B1 (en) | 2000-12-05 | 2004-08-10 | Chevron U.S.A. Inc. | Process for preparing lubes with high viscosity index values |
| KR100447932B1 (ko) | 2001-10-19 | 2004-09-08 | 한국화학연구원 | 실리콘이 함유된 내유기용매성 폴리아미드 나노복합막과 이의 제조방법 |
| DK1461315T3 (da) | 2001-12-06 | 2009-11-16 | Cornell Res Foundation Inc | Katalytisk carbonylering af tre- og fireleddede heterocykler |
| CN1315771C (zh) | 2002-05-06 | 2007-05-16 | 伊斯曼化学公司 | 连续羰基化工艺 |
| DE10221176A1 (de) | 2002-05-13 | 2003-11-27 | Basf Ag | Verfahren zur Herstellung geruchsarmer Hydrogelbildender Polymerisate |
| DE10235316A1 (de) | 2002-08-01 | 2004-02-12 | Basf Ag | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| DE10235317A1 (de) * | 2002-08-01 | 2004-02-12 | Basf Ag | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| US6872753B2 (en) | 2002-11-25 | 2005-03-29 | Conocophillips Company | Managing hydrogen and carbon monoxide in a gas to liquid plant to control the H2/CO ratio in the Fischer-Tropsch reactor feed |
| KR20050121247A (ko) | 2003-04-09 | 2005-12-26 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | 에폭시드의 카보닐화 |
| KR101143206B1 (ko) | 2003-07-25 | 2012-05-18 | 디에스엠 아이피 어셋츠 비.브이. | 팔라듐 촉매 시스템을 사용하여 공액 다이엔을카본일화시키는 방법 |
| CN1946656B (zh) | 2004-02-17 | 2011-08-24 | 托马斯·E·约翰逊 | 形成大环化合物的方法、组合物和设备 |
| US20050196343A1 (en) | 2004-02-27 | 2005-09-08 | Molecular Therapeutics, Inc. | Degradable nanoparticles |
| EP1732874A1 (en) | 2004-04-02 | 2006-12-20 | Ciba Speciality Chemicals Water Treatments Limited | Preparation of acrylic acid derivatives from alpha or beta-hydroxy carboxylic acids |
| JP4759236B2 (ja) | 2004-07-28 | 2011-08-31 | 住友精化株式会社 | カルボキシル基含有水溶性重合体の製造方法 |
| EP1796822A4 (en) | 2004-10-06 | 2008-09-17 | Res Foundation Suny | INTENSE FLOW FILTRATION MEDIA WITH LOW ENCRYPTION |
| TW200630156A (en) | 2005-02-03 | 2006-09-01 | Shell Int Research | Treatment of an aqueous mixture containing an alkylene oxide with an ion exchange resin |
| GB2423300A (en) | 2005-02-17 | 2006-08-23 | Membrane Extraction Tech Ltd | Separating enantiomers & isomers by formation, separation & decomposition of host-guest complex, & separation of host & guest molecules with membrane |
| DE102005017049A1 (de) | 2005-04-12 | 2006-10-19 | Basf Ag | Verfahren zur Herstellung von Polyhydroxyalkanoaten |
| DE102005039156B4 (de) | 2005-08-17 | 2014-12-24 | Evonik Degussa Gmbh | Verfahren zur Herstellung von (Meth)Acrylsäure mit Schwersiedeaufarbeitung durch Kristallisation |
| WO2007064841A2 (en) | 2005-11-30 | 2007-06-07 | North Carolina State University | Porphyrinic compounds for use in flow cytometry |
| US7569709B2 (en) | 2006-03-10 | 2009-08-04 | Cornell Research Foundation, Inc. | Low pressure carbonylation of heterocycles |
| DE102006019242A1 (de) | 2006-04-21 | 2007-10-25 | Bayer Technology Services Gmbh | Prozessanalysensystem mit steriler Probenahme von mechanisch empfindlichem Material aus einem Bioreaktor |
| US7582792B2 (en) | 2006-06-15 | 2009-09-01 | Eastman Chemical Company | Carbonylation process |
| KR101477491B1 (ko) | 2006-09-15 | 2014-12-31 | 알케마 인코포레이티드 | 아크릴산의 제조방법 |
| DE102006045282C5 (de) | 2006-09-22 | 2012-11-22 | Helmholtz-Zentrum Geesthacht Zentrum für Material-und Küstenforschung GmbH | Isoporöse Membran und Verfahren zu ihrer Herstellung |
| US20100323885A1 (en) | 2007-03-12 | 2010-12-23 | Basf Se A German Corporation | Process for Producing Re-Moisturised Surface-Crosslinked Superabsorbents |
| US20080290033A1 (en) | 2007-05-25 | 2008-11-27 | Camp Dresser & Mckee, Inc. | Method and apparatus for recovery of water containing silica |
| JP5315679B2 (ja) | 2007-11-30 | 2013-10-16 | 三菱化学株式会社 | フラン化合物の製造方法 |
| EP3441048B1 (en) | 2008-05-15 | 2025-08-13 | Angelini Pharma Inc. | Portable moist heat system |
| US7858729B2 (en) | 2008-05-29 | 2010-12-28 | Novomer, Inc. | Methods of controlling molecular weight distribution of polymers and compositions thereof |
| CN102245218B (zh) | 2008-12-19 | 2014-10-22 | Sca卫生用品公司 | 包含超吸收聚合物和纤维素纳米纤丝的超吸收聚合物复合物 |
| CA2757835A1 (en) * | 2009-04-08 | 2010-10-14 | Novomer, Inc. | Process for beta-lactone production |
| WO2010137974A1 (en) | 2009-05-25 | 2010-12-02 | Universiteit Twente | Polymer composition comprising a blend of a multi-block thermoplastic elastomer and a polymer comprising a group 14 metal |
| KR101238782B1 (ko) | 2009-07-03 | 2013-02-28 | 주식회사 엘지화학 | 고흡수성 수지 제조용 중합 반응기 및 상기 중합 반응기를 사용한 고흡수성 수지의 제조 방법 |
| WO2011035195A1 (en) | 2009-09-18 | 2011-03-24 | Nano Terra Inc. | Functional nanofibers and methods of making and using the same |
| JP5731390B2 (ja) | 2009-09-30 | 2015-06-10 | 株式会社日本触媒 | ポリアクリル酸(塩)系吸水性樹脂およびその製造方法 |
| EP2325214B1 (en) | 2009-11-20 | 2015-11-18 | King Saud University | Synthesis of acrylic or methacrylic acid/acrylate or methacrylate ester polymers using pervaporation |
| WO2011110441A2 (en) | 2010-03-09 | 2011-09-15 | Polymers Crc Ltd | Polyurethane block copolymer based on poly siloxane tenside for membranes |
| EP2371869A1 (en) | 2010-03-30 | 2011-10-05 | Evonik Stockhausen GmbH | A process for the production of a superabsorbent polymer |
| WO2011123558A1 (en) | 2010-04-01 | 2011-10-06 | Novomer, Inc. | Synthesis of metal complexes |
| WO2011163309A2 (en) | 2010-06-22 | 2011-12-29 | Cornell University | Carbonylative polymerization methods |
| US9156803B2 (en) | 2010-08-28 | 2015-10-13 | Novomer, Inc. | Succinic anhydride from ethylene oxide |
| HUE046261T2 (hu) | 2010-10-11 | 2020-02-28 | Novomer Inc | Polimerkeverékek |
| EP2476724A1 (en) | 2011-01-17 | 2012-07-18 | ETH Zurich | Pourous polymer membranes |
| US9555401B2 (en) | 2011-01-25 | 2017-01-31 | Zeochem Llc | Molecular sieve adsorbent blends and uses thereof |
| CN103649038A (zh) | 2011-05-13 | 2014-03-19 | 诺沃梅尔公司 | 催化羰基化催化剂和方法 |
| US20110319849A1 (en) | 2011-07-01 | 2011-12-29 | Dimitris Ioannis Collias | Absorbent article comprising a synthetic polymer derived from a renewable resource and methods of producing said article |
| WO2013063191A1 (en) | 2011-10-26 | 2013-05-02 | Novomer, Inc. | Process for production of acrylates from epoxides |
| WO2013067460A1 (en) | 2011-11-04 | 2013-05-10 | Novomer, Inc. | Metal complexes for the copolymerization of carbon dioxide and epoxides |
| IN2014CN04115A (enExample) | 2011-11-09 | 2015-07-10 | Evonik Membrane Extraction Technology Ltd | |
| US9403788B2 (en) | 2012-02-13 | 2016-08-02 | Novomer, Inc. | Process for the production of acid anhydrides from epoxides |
| SI2817285T1 (sl) | 2012-02-22 | 2019-04-30 | Novomer, Inc. | Postopki proizvodnje akrilne kisline |
| US9630901B2 (en) | 2012-04-11 | 2017-04-25 | The Procter & Gamble Company | Poly(acrylic acid) from bio-based acrylic acid and its derivatives |
| US20150136690A1 (en) | 2012-06-01 | 2015-05-21 | National Unibersity of Singapore | Method of making a membrane and a membrane for water filtration |
| WO2013185009A1 (en) | 2012-06-08 | 2013-12-12 | Metabolix, Inc. | Renewable acrylic acid production and products made therefrom |
| JP6299086B2 (ja) | 2012-06-08 | 2018-03-28 | 三菱ケミカル株式会社 | フルフラールの精製方法 |
| CA2877903A1 (en) | 2012-06-27 | 2014-01-03 | Novomer, Inc. | Catalysts and methods for polyester production |
| EP2867189A4 (en) * | 2012-07-02 | 2016-03-16 | Novomer Inc | PROCESS FOR PRODUCING ACRYLATE |
| DE102012212424A1 (de) | 2012-07-16 | 2014-01-16 | Basf Se | Verfahren zur Herstellung von Acrylsäure durch eine mit wenigstens einer molekularen Wirkverbindung katalysierte Thermolyse von Poly-3-hydroxypropionat |
| DE102012212437A1 (de) * | 2012-07-16 | 2014-01-16 | Basf Se | Verfahren zur Herstellung von Acrylsäure aus Ethylenoxid und Kohlenmonoxid |
| JP6253155B2 (ja) | 2013-09-25 | 2017-12-27 | 富士フイルム株式会社 | 固体電解質組成物、これを用いた電池用電極シートおよび全固体二次電池 |
| JP2017506286A (ja) | 2013-12-07 | 2017-03-02 | ノボマー, インコーポレイテッド | ナノろ過膜および使用の方法 |
| JP6516760B2 (ja) | 2014-01-24 | 2019-05-22 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | モノマー溶液の液滴の重合による吸水性ポリマー粒子の製造方法 |
| CN103822811B (zh) | 2014-02-28 | 2016-01-27 | 中国地质大学(武汉) | 一种测试有机物类样品14c丰度的前处理方法和设备 |
| CA2941714A1 (en) | 2014-03-14 | 2015-09-17 | Novomer, Inc. | Catalysts for epoxide carbonylation |
| EP3140292B1 (en) | 2014-05-05 | 2021-02-24 | Novomer, Inc. | Catalyst recycle methods |
| EP3848011A1 (en) | 2014-05-08 | 2021-07-14 | The Procter & Gamble Company | Waist to side silhouettes of adult disposable absorbent articles and arrays |
| WO2015184289A1 (en) | 2014-05-30 | 2015-12-03 | Novomer Inc. | Integrated methods for chemical synthesis |
| JP6670011B2 (ja) | 2014-07-25 | 2020-03-18 | ノボマー, インコーポレイテッド | 金属錯体の合成およびその使用 |
| US20180029005A1 (en) | 2015-02-13 | 2018-02-01 | Novomer, Inc. | Flexible chemical production platform |
| MA41508A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production d'acide polyacrylique |
| EP3256510B1 (en) | 2015-02-13 | 2020-12-09 | Novomer, Inc. | Process and system for production of polypropiolactone |
| EP3256441B1 (en) * | 2015-02-13 | 2020-04-08 | Novomer, Inc. | Continuous carbonylation processes |
| MA41507A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production de polymères |
| MA41513A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de distillation pour la production d'acide acrylique |
| MA41510A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| MA41514A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédés intégrés de synthèse chimique |
| BR112018002143A2 (pt) | 2015-07-31 | 2018-09-18 | Novomer Inc | sistema de produção/processo de produção para ácido acrílico e precursores do mesmo |
| CN108884009A (zh) | 2016-03-21 | 2018-11-23 | 诺沃梅尔公司 | 制造超吸收性聚合物的系统和方法 |
| AU2017236914A1 (en) | 2016-03-21 | 2018-11-08 | Novomer, Inc. | Improved acrylic acid production process |
| US20180282251A1 (en) | 2017-03-21 | 2018-10-04 | Novomer, Inc. | Systems and processes for producing organic acids direct from beta-lactones |
| US20180305286A1 (en) | 2016-03-21 | 2018-10-25 | Novomer, Inc. | Systems and Processes for Producing Organic Acids Direct from Beta-Lactones |
| MA46720A (fr) | 2016-11-02 | 2019-09-11 | Novomer Inc | Polymères absorbants, procédés et systèmes de production et utilisations correspondantes |
| CN109843947A (zh) | 2016-11-02 | 2019-06-04 | 诺沃梅尔公司 | 吸收性聚合物和其制造方法及其用途 |
| US10144802B2 (en) | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US20180155490A1 (en) | 2016-12-05 | 2018-06-07 | Novomer, Inc. | Biodegradable polyols having higher biobased content |
| US10500104B2 (en) | 2016-12-06 | 2019-12-10 | Novomer, Inc. | Biodegradable sanitary articles with higher biobased content |
| AR110833A1 (es) | 2017-01-19 | 2019-05-08 | Novomer Inc | Métodos y sistemas para el tratamiento de óxido de etileno |
| EP3596156A4 (en) | 2017-03-17 | 2020-12-30 | Novomer, Inc. | POLYAMIDES AND PROCESSES FOR THE PRODUCTION OF THESE POLYAMIDES |
| US10065914B1 (en) | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10676426B2 (en) | 2017-06-30 | 2020-06-09 | Novomer, Inc. | Acrylonitrile derivatives from epoxide and carbon monoxide reagents |
| US20190002385A1 (en) | 2017-06-30 | 2019-01-03 | Novomer, Inc. | Compositions for improved production of acrylic acid |
| US10781156B2 (en) | 2017-06-30 | 2020-09-22 | Novomer, Inc. | Compositions for improved production of acrylic acid |
| US10899622B2 (en) | 2017-06-30 | 2021-01-26 | Novomer, Inc. | Biobased carbon fibers and carbon black and methods of making the same |
| US10961209B2 (en) | 2017-08-10 | 2021-03-30 | Novomer, Inc. | Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts |
| CN111094237A (zh) | 2017-09-09 | 2020-05-01 | 诺沃梅尔公司 | 酰胺化合物和腈化合物及其生产与使用方法 |
| US20190076835A1 (en) | 2017-09-11 | 2019-03-14 | Novomer, Inc. | Processses using multifunctional catalysts |
| US20190076834A1 (en) | 2017-09-11 | 2019-03-14 | Novomer, Inc. | Processes Using Multifunctional Catalysts |
| US11288976B2 (en) | 2017-10-05 | 2022-03-29 | Fluent Forever Inc. | Language fluency system |
| CN111182968A (zh) | 2017-10-05 | 2020-05-19 | 诺沃梅尔公司 | 异氰酸酯、其衍生物及它们的生产方法 |
-
2016
- 2016-02-12 EP EP16750021.4A patent/EP3256441B1/en active Active
- 2016-02-12 WO PCT/US2016/017875 patent/WO2016130998A1/en not_active Ceased
- 2016-02-12 KR KR1020177025875A patent/KR20170134374A/ko not_active Withdrawn
- 2016-02-12 CA CA2976253A patent/CA2976253A1/en not_active Abandoned
- 2016-02-12 HK HK18105401.2A patent/HK1245761A1/zh unknown
- 2016-02-12 JP JP2017542467A patent/JP7053264B2/ja active Active
- 2016-02-12 CN CN201680018399.3A patent/CN107428656B/zh active Active
- 2016-02-12 AU AU2016218996A patent/AU2016218996A1/en not_active Abandoned
- 2016-02-12 MX MX2017010408A patent/MX2017010408A/es unknown
- 2016-02-12 EP EP20168015.4A patent/EP3696161A1/en not_active Withdrawn
- 2016-02-12 US US15/550,217 patent/US10221150B2/en active Active
-
2017
- 2017-08-09 SA SA517382089A patent/SA517382089B1/ar unknown
-
2019
- 2019-01-15 US US16/248,509 patent/US10738022B2/en active Active
- 2019-02-26 JP JP2019032485A patent/JP2019116486A/ja active Pending
-
2020
- 2020-07-02 US US16/919,644 patent/US10927091B2/en active Active
-
2021
- 2021-08-05 JP JP2021128752A patent/JP7170351B2/ja active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019143220A1 (ko) * | 2018-01-22 | 2019-07-25 | 국민대학교 산학협력단 | 전이금속 기반 비균질계 카보닐화 반응촉매 및 이를 이용한 락톤 또는 숙신산 무수물의 제조방법 |
| KR20190089312A (ko) * | 2018-01-22 | 2019-07-31 | 국민대학교산학협력단 | 전이금속 기반 비균질계 카보닐화 반응촉매 및 이를 이용한 락톤 또는 숙신산 무수물의 제조방법 |
| US11071973B2 (en) | 2018-01-22 | 2021-07-27 | Kookmin University Industry Academy Cooperation Foundation | Transition metal-based heterogeneous carbonylation reaction catalyst and method for preparing lactone or succinic anhydride using catalyst |
| US11648545B2 (en) | 2018-01-22 | 2023-05-16 | Kookmin University Industry Academy Cooperation Foundation | Transition metal-based heterogeneous carbonylation reaction catalyst and method for preparing lactone or succinic anhydride using catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| US10927091B2 (en) | 2021-02-23 |
| JP2021185147A (ja) | 2021-12-09 |
| JP7170351B2 (ja) | 2022-11-14 |
| SA517382089B1 (ar) | 2022-06-19 |
| US10221150B2 (en) | 2019-03-05 |
| JP2018507855A (ja) | 2018-03-22 |
| JP7053264B2 (ja) | 2022-04-12 |
| US10738022B2 (en) | 2020-08-11 |
| CN107428656B (zh) | 2021-06-08 |
| EP3256441A1 (en) | 2017-12-20 |
| HK1245761A1 (zh) | 2018-08-31 |
| WO2016130998A1 (en) | 2016-08-18 |
| CA2976253A1 (en) | 2016-08-18 |
| EP3256441B1 (en) | 2020-04-08 |
| AU2016218996A1 (en) | 2017-08-24 |
| EP3696161A1 (en) | 2020-08-19 |
| US20180030015A1 (en) | 2018-02-01 |
| US20200331878A1 (en) | 2020-10-22 |
| MX2017010408A (es) | 2018-02-23 |
| CN107428656A (zh) | 2017-12-01 |
| JP2019116486A (ja) | 2019-07-18 |
| US20190345125A1 (en) | 2019-11-14 |
| EP3256441A4 (en) | 2018-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7170351B2 (ja) | 連続的カルボニル化方法 | |
| US11492443B2 (en) | Process and system for production of polypropiolactone | |
| KR20170129734A (ko) | 폴리아크릴산 제조를 위한 시스템 및 방법 | |
| EP3116646A1 (en) | Catalysts for epoxide carbonylation | |
| KR20170047248A (ko) | 금속 착체의 합성 및 이의 용도 | |
| KR20170012479A (ko) | 화학 합성을 위한 통합된 방법 | |
| KR20170117542A (ko) | 화학 합성을 위한 통합된 방법 | |
| KR20150036034A (ko) | 폴리에스터 제조를 위한 촉매 및 방법 | |
| HK1241850A1 (zh) | 连续羰基化方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20170913 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination |