CA2994403A1 - Production system/production process for acrylic acid and precursors thereof - Google Patents
Production system/production process for acrylic acid and precursors thereof Download PDFInfo
- Publication number
- CA2994403A1 CA2994403A1 CA2994403A CA2994403A CA2994403A1 CA 2994403 A1 CA2994403 A1 CA 2994403A1 CA 2994403 A CA2994403 A CA 2994403A CA 2994403 A CA2994403 A CA 2994403A CA 2994403 A1 CA2994403 A1 CA 2994403A1
- Authority
- CA
- Canada
- Prior art keywords
- stream
- bpl
- propiolactone
- solvent
- carbonylation
- 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.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 296
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 95
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 239000002243 precursor Substances 0.000 title description 17
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims abstract description 531
- 229960000380 propiolactone Drugs 0.000 claims abstract description 503
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 194
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 194
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 160
- 238000000034 method Methods 0.000 claims abstract description 96
- 238000001149 thermolysis Methods 0.000 claims abstract description 50
- 239000003054 catalyst Substances 0.000 claims description 536
- 238000005810 carbonylation reaction Methods 0.000 claims description 519
- 230000006315 carbonylation Effects 0.000 claims description 407
- 239000002904 solvent Substances 0.000 claims description 352
- 238000006116 polymerization reaction Methods 0.000 claims description 254
- 238000000746 purification Methods 0.000 claims description 152
- 238000006243 chemical reaction Methods 0.000 claims description 139
- -1 alkali metal salts Chemical class 0.000 claims description 138
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 118
- 239000012528 membrane Substances 0.000 claims description 106
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 97
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 88
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 74
- 229940014800 succinic anhydride Drugs 0.000 claims description 74
- 238000000926 separation method Methods 0.000 claims description 71
- 239000003505 polymerization initiator Substances 0.000 claims description 69
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 58
- 238000004821 distillation Methods 0.000 claims description 50
- 238000004064 recycling Methods 0.000 claims description 48
- 230000008569 process Effects 0.000 claims description 43
- 125000000129 anionic group Chemical group 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 229910052782 aluminium Inorganic materials 0.000 claims description 38
- 239000007787 solid Substances 0.000 claims description 35
- 238000005342 ion exchange Methods 0.000 claims description 32
- 150000002500 ions Chemical class 0.000 claims description 30
- 229910017052 cobalt Inorganic materials 0.000 claims description 29
- 239000010941 cobalt Substances 0.000 claims description 29
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 29
- 239000003999 initiator Substances 0.000 claims description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 18
- 239000012466 permeate Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- 238000011084 recovery Methods 0.000 claims description 14
- 239000012465 retentate Substances 0.000 claims description 13
- 239000010408 film Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 125000002091 cationic group Chemical group 0.000 claims description 11
- 229960004132 diethyl ether Drugs 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 238000012545 processing Methods 0.000 claims description 9
- 238000010526 radical polymerization reaction Methods 0.000 claims description 9
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- 229940052303 ethers for general anesthesia Drugs 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
- OXMIDRBAFOEOQT-UHFFFAOYSA-N 2,5-dimethyloxolane Chemical compound CC1CCC(C)O1 OXMIDRBAFOEOQT-UHFFFAOYSA-N 0.000 claims description 6
- 229940048053 acrylate Drugs 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 5
- HWJKSUASHASQGB-UHFFFAOYSA-M prop-2-enoate tetraphenylphosphanium Chemical compound [O-]C(=O)C=C.c1ccc(cc1)[P+](c1ccccc1)(c1ccccc1)c1ccccc1 HWJKSUASHASQGB-UHFFFAOYSA-M 0.000 claims description 5
- DGUTXSBBNRQOKD-UHFFFAOYSA-M prop-2-enoate trimethyl(phenyl)azanium Chemical compound [O-]C(=O)C=C.C[N+](C)(C)c1ccccc1 DGUTXSBBNRQOKD-UHFFFAOYSA-M 0.000 claims description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- DLSULYIQRAZOPW-UHFFFAOYSA-M trimethyl(phenyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C1=CC=CC=C1 DLSULYIQRAZOPW-UHFFFAOYSA-M 0.000 claims description 5
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 4
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims description 4
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
- 229960002479 isosorbide Drugs 0.000 claims description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 4
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims description 3
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- 229940047670 sodium acrylate Drugs 0.000 claims description 3
- 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 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- BLJNPOIVYYWHMA-UHFFFAOYSA-N alumane;cobalt Chemical compound [AlH3].[Co] BLJNPOIVYYWHMA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000011552 falling film Substances 0.000 claims description 2
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 claims 1
- OIQOECYRLBNNBQ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] OIQOECYRLBNNBQ-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- RIZPLDXMQXJTTJ-UHFFFAOYSA-N phosphane;prop-2-enoic acid Chemical compound [PH4+].[O-]C(=O)C=C RIZPLDXMQXJTTJ-UHFFFAOYSA-N 0.000 claims 1
- TWWBIMNLBUYJKB-UHFFFAOYSA-N phosphanyl acetate Chemical compound CC(=O)OP TWWBIMNLBUYJKB-UHFFFAOYSA-N 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000010977 unit operation Methods 0.000 abstract description 14
- 239000000047 product Substances 0.000 description 221
- 229910052751 metal Inorganic materials 0.000 description 133
- 239000002184 metal Substances 0.000 description 133
- 239000002685 polymerization catalyst Substances 0.000 description 74
- 238000009835 boiling Methods 0.000 description 51
- 239000000463 material Substances 0.000 description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
- 150000001728 carbonyl compounds Chemical class 0.000 description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 229910052760 oxygen Inorganic materials 0.000 description 36
- 239000001301 oxygen Substances 0.000 description 36
- 239000002841 Lewis acid Substances 0.000 description 35
- 238000002955 isolation Methods 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 29
- 238000001816 cooling Methods 0.000 description 29
- 238000001728 nano-filtration Methods 0.000 description 29
- 239000007789 gas Substances 0.000 description 28
- 125000000623 heterocyclic group Chemical group 0.000 description 28
- 239000012535 impurity Substances 0.000 description 28
- 125000001931 aliphatic group Chemical group 0.000 description 26
- 150000007517 lewis acids Chemical class 0.000 description 26
- 239000007788 liquid Substances 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 22
- 230000007935 neutral effect Effects 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 19
- 230000036961 partial effect Effects 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- 241000894007 species Species 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- 239000011593 sulfur Substances 0.000 description 19
- 239000003446 ligand Substances 0.000 description 18
- 238000002156 mixing Methods 0.000 description 18
- 150000007942 carboxylates Chemical class 0.000 description 17
- 150000001768 cations Chemical class 0.000 description 17
- 125000005842 heteroatom Chemical group 0.000 description 17
- 239000002608 ionic liquid Substances 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
- 239000006227 byproduct Substances 0.000 description 15
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000003456 ion exchange resin Substances 0.000 description 14
- 229920003303 ion-exchange polymer Polymers 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 238000010517 secondary reaction Methods 0.000 description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 12
- 239000003463 adsorbent Substances 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 12
- 229910001429 cobalt ion Inorganic materials 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- 239000002879 Lewis base Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 238000005349 anion exchange Methods 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 11
- 150000007527 lewis bases Chemical class 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 230000002051 biphasic effect Effects 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000004642 Polyimide Substances 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 150000001639 boron compounds Chemical class 0.000 description 8
- 238000005341 cation exchange Methods 0.000 description 8
- 239000003426 co-catalyst Substances 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 229920001721 polyimide Polymers 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 238000010926 purge Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 229910021645 metal ion Inorganic materials 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 230000035699 permeability Effects 0.000 description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 7
- 238000000638 solvent extraction Methods 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 6
- 238000012674 dispersion polymerization Methods 0.000 description 6
- 239000002638 heterogeneous catalyst Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 238000000622 liquid--liquid extraction Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920002239 polyacrylonitrile Polymers 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 238000004435 EPR spectroscopy Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 239000004584 polyacrylic acid Substances 0.000 description 4
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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Classifications
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- 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
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1862—Stationary reactors having moving elements inside placed in series
-
- 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
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/785—Preparation processes characterised by the apparatus used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Absorbent Articles And Supports Therefor (AREA)
Applications Claiming Priority (3)
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| BR112018002143A2 (pt) | 2018-09-18 |
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| US10703702B2 (en) | 2020-07-07 |
| WO2017023777A9 (en) | 2017-10-12 |
| WO2017023777A1 (en) | 2017-02-09 |
| JP2018525374A (ja) | 2018-09-06 |
| CN108026013A (zh) | 2018-05-11 |
| US20220251018A1 (en) | 2022-08-11 |
| WO2017023820A1 (en) | 2017-02-09 |
| JP7398124B2 (ja) | 2023-12-14 |
| CN108026013B (zh) | 2022-09-13 |
| KR20180027632A (ko) | 2018-03-14 |
| KR20180027631A (ko) | 2018-03-14 |
| HK1249496A1 (zh) | 2018-11-02 |
| US20170029352A1 (en) | 2017-02-02 |
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