EP4153556A1 - Method for preparing acrylic acid from beta-propiolactone - Google Patents
Method for preparing acrylic acid from beta-propiolactoneInfo
- Publication number
- EP4153556A1 EP4153556A1 EP21725208.9A EP21725208A EP4153556A1 EP 4153556 A1 EP4153556 A1 EP 4153556A1 EP 21725208 A EP21725208 A EP 21725208A EP 4153556 A1 EP4153556 A1 EP 4153556A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- chosen
- propiolactone
- acrylic acid
- crown
- methyl
- 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.)
- Pending
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 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 76
- 238000000034 method Methods 0.000 title claims abstract description 71
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 title claims description 65
- 229960000380 propiolactone Drugs 0.000 title claims description 65
- 230000008569 process Effects 0.000 claims abstract description 51
- -1 alkyl radical Chemical class 0.000 claims description 50
- 239000003054 catalyst Substances 0.000 claims description 49
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 26
- 150000005840 aryl radicals Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 8
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 7
- 239000002250 absorbent Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003973 paint Substances 0.000 claims description 7
- 229920001155 polypropylene Polymers 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 229920002972 Acrylic fiber Polymers 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000003337 fertilizer Substances 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 239000003292 glue Substances 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000575 pesticide Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920006243 acrylic copolymer Polymers 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000012847 fine chemical Substances 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005202 decontamination Methods 0.000 claims description 4
- 230000003588 decontaminative effect Effects 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920003051 synthetic elastomer Polymers 0.000 claims description 4
- 239000005061 synthetic rubber Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 3
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- HBZDPWBWBJMYRY-UHFFFAOYSA-N decanenitrile Chemical compound CCCCCCCCCC#N HBZDPWBWBJMYRY-UHFFFAOYSA-N 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- 238000007306 functionalization reaction Methods 0.000 claims description 3
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 3
- GZORJAFFPJJJQU-UHFFFAOYSA-N n,n-dimethylacetamide;1-methylpyrrolidin-2-one Chemical compound CN(C)C(C)=O.CN1CCCC1=O GZORJAFFPJJJQU-UHFFFAOYSA-N 0.000 claims description 3
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 claims description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims description 2
- HELCSRZMDRYPIJ-UHFFFAOYSA-N 1,4,7,10,13,16-hexathiacyclooctadecane Chemical compound C1CSCCSCCSCCSCCSCCS1 HELCSRZMDRYPIJ-UHFFFAOYSA-N 0.000 claims description 2
- RVJABZUDCPZPPM-UHFFFAOYSA-N 1,4,7,10,13,16-hexazacyclooctadecane Chemical compound C1CNCCNCCNCCNCCNCCN1 RVJABZUDCPZPPM-UHFFFAOYSA-N 0.000 claims description 2
- LIVCAIOLNUODDU-UHFFFAOYSA-N 1,5,9,13-tetrathiacyclohexadecane Chemical compound C1CSCCCSCCCSCCCSC1 LIVCAIOLNUODDU-UHFFFAOYSA-N 0.000 claims description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 claims description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 2
- DSFHXKRFDFROER-UHFFFAOYSA-N 2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(22),18,20-triene Chemical compound O1CCOCCOCCOCCOCCOC2=CC=CC=C21 DSFHXKRFDFROER-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- FNEPSTUXZLEUCK-UHFFFAOYSA-N benzo-15-crown-5 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C21 FNEPSTUXZLEUCK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002739 cryptand Substances 0.000 claims description 2
- QSBFECWPKSRWNM-UHFFFAOYSA-N dibenzo-15-crown-5 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOC2=CC=CC=C21 QSBFECWPKSRWNM-UHFFFAOYSA-N 0.000 claims description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 2
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 claims description 2
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229940093499 ethyl acetate Drugs 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 1
- 229940090181 propyl acetate Drugs 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000009257 reactivity Effects 0.000 abstract description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 10
- 150000002596 lactones Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000003983 crown ethers Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZOMPBXWFMAJRRU-UHFFFAOYSA-N 3-ethyloxiran-2-one Chemical compound CCC1OC1=O ZOMPBXWFMAJRRU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920002392 Novomer Polymers 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 238000003911 water pollution Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910017299 Mo—O Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 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
- 125000002704 decyl 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])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28033—Membrane, sheet, cloth, pad, lamellar or mat
- B01J20/28038—Membranes or mats made from fibers or filaments
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3206—Organic carriers, supports or substrates
- B01J20/3208—Polymeric carriers, supports or substrates
- B01J20/321—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
- B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3268—Macromolecular compounds
- B01J20/3278—Polymers being grafted on the carrier
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
- B01J20/3293—Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/288—Treatment of water, waste water, or sewage by sorption using composite sorbents, e.g. coated, impregnated, multi-layered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/32—Materials not provided for elsewhere for absorbing liquids to remove pollution, e.g. oil, gasoline, fat
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/20—Polyalkenes, polymers or copolymers of compounds with alkenyl groups bonded to aromatic groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
Definitions
- TITLE PROCESS FOR PREPARING ACRYLIC ACID FROM ⁇ -PROPIOLACTONE
- the present invention relates to a process for preparing acrylic acid from ⁇ -propiolactone and its uses.
- the process of the invention is based on a specific reactivity of ⁇ -propiolactone which, under mild operating conditions, in particular in terms of temperature, selectively leads to the formation of acrylic acid.
- Technical background Acrylic acid is the simplest and most common of the ⁇ , ⁇ -unsaturated acids, it is widely used on an industrial scale. This resource was produced to the tune of 5.94 Mt in 2014 and demand is growing every year.
- Acrylic acid is mainly used for the production of super-absorbent materials, the formulation of resins and paints, but also as an intermediate for the synthesis of monomers, making it possible to diversify its applications.
- the industrial acrylic acid synthesis process is based mainly on the oxidation of propylene, obtained from petrochemicals.
- the increase in the price of acrylic acid in Europe is correlated with the price of propylene.
- the latter experienced an increase in its price of 60% between 2013 and 2014, which requires the development of new technologies and synthetic routes as shown schematically in [FIG.1].
- There is a growing number of publications on the formation of acrylic acid from lactic acid or glycerol in order to avoid products derived from petroleum R. Beerthuis et al., Green Chem.
- the first step is based on the oxidation of propylene to acrolein using a catalyst based on of Bismuth and Molybdenum (Bi / Mo-O) at 320 ° C.
- the intermediate thus formed is then directly converted into acrylic acid using a second oxidation involving a catalyst based on bismuth and vanadium (Bi / VO) at 280 ° C.
- the object of the present invention is precisely to meet these needs by providing a process for the preparation of acrylic acid from ⁇ -propiolactone, characterized in that the ⁇ -propiolactone is brought into contact with a catalyst of formula (I): YX (I) in which Y represents an alkali metal cation, quaternary ammonium of formula [NR 1 R 2 R 3 R 4 ] + , in which R 1 , R 2 , R 3 and R 4 , identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 12 carbon atoms, an aryl radical comprising from 6 to 20 carbon atoms, said alkyl and aryl radicals being optionally substituted, phosphonium of formula [PR 1 R 2 R 3 R 4 ] + , in which R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 12 carbon atoms, an aryl radical comprising from 6
- ⁇ -propiolactone can be produced by carbonylation of ethylene oxide, derived from the oxidation of ethylene, the latter possibly being biobased or petrosourced.
- ⁇ -propiolactone can also be obtained from formaldehyde and ketene. It is also available commercially.
- the process of the invention is based on a specific reactivity of ⁇ -propiolactone which, under mild operating conditions, in particular in terms of temperature, selectively leads to the formation of acrylic acid. Indeed, the inventors have observed, quite unexpectedly, that the same mild operating conditions applied to other lactones were totally ineffective. As shown in [Fig.
- the lactide under operating conditions in accordance with the invention, in particular in terms of catalyst, solvent, reaction time and temperature, the lactide is not at all transformed and the ⁇ -butyrolactone, the structure of which is not differs from that of ⁇ -propiolactone only by the presence of a methyl group, undergoes a decarboxylation reaction to form propylene and CO2.
- Another object of the invention is the use of a process for preparing acrylic acid from ⁇ -propiolactone according to the invention, in the manufacture of: - super-absorbent materials, - layers, - rubbers synthetic, - plastics, - coatings, - paints, - ink, - organic glasses, - glues, - acrylic fibers, - synthetic leathers, - pharmaceuticals, - pesticides, - d 'fertilizer, - detergents, - reagents for fine chemicals, - intermediates for the manufacture of acrylic esters, and - acrylic polymers and copolymers.
- the invention also relates to a method of manufacturing super-absorbent materials, layers, synthetic rubbers, plastics, coatings, paints, ink, organic glasses, glues, acrylic fibers, synthetic leathers. , pharmaceuticals, pesticides, fertilizers, detergents, reagents for fine chemicals, intermediates for the manufacture of acrylic esters, and acrylic polymers and copolymers, characterized in that it comprises: ( i) a step of preparing acrylic acid from ⁇ -propiolactone by the process according to the invention, and optionally (ii) a step of separating acrylic acid, for example, by distillation.
- the method of the invention can be used in water pollution control (https://surfacechemistry.nouryon.com/SiteAssets/pdfs/techbulletin-water-treatment-product- selection-guide-global-2.pdf; https: / / grandviewresearchinc.blogspot.com/2017/12/polyacrylic- acid-based-polymers-to-simplify-industrial-waste-water-treatment.html).
- a further subject of the invention is a process for the functionalization of technical textiles based on polypropylene (PP) intended for the decontamination of water, characterized in that it comprises a step of preparing acrylic acid from ⁇ -propiolactone by the process according to the invention.
- PP polypropylene
- FIG. 1 shows a diagram of the production and use of acrylic acid as described in T. Bonnotte et al., ChemBioEng Rev 2018, 5, No. 1, 34-56; R. Beerthuis et al., Green Chem., 2015, 17, 1341 (Propylene to Acrylic Acid + Applications); V. Mahadevan et al., Angew. Chem.
- FIG. 2 shows the inventive nature and the specificity of the process for preparing acrylic acid from ⁇ -propiolactone according to the invention.
- the present invention relates to a process for preparing acrylic acid from ⁇ -propiolactone, characterized in that the ⁇ -propiolactone is brought into contact with a catalyst of formula (I): YX (I) in which Y represents an alkali metal cation, quaternary ammonium of the formula [NR 1 R 2 R 3 R 4 ] + , in which R 1 , R 2 , R 3 and R 4 , identical or different, represent a hydrogen atom , an alkyl radical comprising 1 to 12 carbon atoms, an aryl radical comprising from 6 to 20 carbon atoms, said alkyl and aryl radicals being optionally substituted, said alkyl and aryl radicals being optionally substituted, phosphonium of formula [PR 1 R 2 R 3 R 4 ] + , in which R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent a hydrogen atom, an alkyl radical comprising 1 to 12 carbon atom
- alkyl is understood to mean a linear, branched or cyclic, saturated, optionally substituted carbon radical comprising 1 to 12 carbon atoms, for example 1 to 8 carbon atoms, for example 1 to 6. carbon atoms.
- saturated, linear or branched alkyl mention may be made, for example, of the methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, decyl, undecyl, dodecanyl radicals and their branched isomers.
- aryl denotes a cyclic aromatic substituent comprising from 6 to 20 carbon atoms.
- the aryl group can comprise, for example, 6 to 10 carbon atoms.
- the aryl group can include, for example, 6 carbon atoms.
- the alkyl and aryl radicals can be optionally substituted by one or more alkoxy (-O-alkyl) groups; one or more halogen atoms chosen from fluorine, chlorine, bromine and iodine atoms; one or more nitro groups (-NO 2 ); one or more nitrile (- CN) groups; one or more alkyl radicals, one or more aryl radicals, with alkyl and aryl as defined in the context of the present invention.
- X is a halide anion chosen from chloride (Cl-), bromide (Br-) and iodide (I-).
- X is a bromide anion. According to another preferred embodiment of the invention, X is an iodide anion.
- Y is an alkali metal cation, it can be chosen from Li + , Na + , K + , and Cs + . According to a preferred embodiment of the invention, the alkali metal cation is K + . According to another preferred embodiment of the invention, the alkali metal cation is Cs + .
- R 1 , R 2 , R 3 and R 4 which may be identical or different, may represent a hydrogen atom, an alkyl radical comprising 1 with 8 carbon atoms, an aryl radical comprising from 6 to 10 carbon atoms, said alkyl and aryl radicals being optionally substituted.
- Y is a quaternary ammonium cation of formula [NR 1 R 2 R 3 R 4 ] + , in which R 1 , R 2 , R 3 and R 4 represent an alkyl radical chosen from among methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and their branched isomers; a radical phenyl chosen from phenyl, benzyl, naphthyl, said alkyl and aryl radicals being optionally substituted.
- Y is advantageously [N (n-Bu) 4] + .
- R 1 , R 2 , R 3 and R 4 which may be identical or different, may represent a hydrogen atom, an alkyl radical comprising 1 to 8 carbon atoms, an aryl radical comprising from 6 to 10 carbon atoms, said alkyl and aryl radicals being optionally substituted.
- Y is a phosphonium cation of formula [PR 1 R 2 R 3 R 4 ] + , R 1 , R 2 , R 3 and R 4 , in which R 1 , R 2 , R 3 and R 4 represent an alkyl radical chosen from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and their branched isomers; a phenyl radical chosen from phenyl, benzyl and naphthyl, said alkyl and aryl radicals being optionally substituted.
- Y is advantageously [PPh4] + .
- the catalyst can, where appropriate, be immobilized on a heterogeneous support, for example, in order to ensure easy separation of said catalyst and / or its recycling.
- Said heterogeneous supports can be chosen from supports based on silica gel or on cationic polymers such as, for example, poly (ethyleneimine) (PEI), poly-L- (lysine) (PLL), or based on polysaccharides.
- the catalyst can be on a solid polymer support such as that available from Sigma Aldrich under the reference Sigma-Aldrich-572942, in particular for the ammonium and phosphonium cations, or that described in https://onlinelibrary.wiley.com/doi/abs/10.1002 /app.35297 (Iodination of stable aromatic diazonium salt using crosslinked poly (4-vinylpyridine) - supported iodide), or the one described in https://pubs.acs.org/doi/abs/10.1021/acs.macromol.9b02266 (Recyclable Solid-Supported Catalysts for Quaternary Ammonium Iodide-Catalyzed Living Radical Polymerization).
- a solid polymer support such as that available from Sigma Aldrich under the reference Sigma-Aldrich-572942, in particular for the ammonium and phosphonium cations, or that described in https://onlinelibrary.wiley.com/doi/
- the catalysts used in the process of the invention which are salts of halides as described above have a low cost. A large part of these catalysts are solids with little or no toxicities and easy to use.
- the process of the invention in particular bringing ⁇ -propiolactone into contact with the catalyst of formula (I), can take place in the absence of solvent. In this case, the presence of a polymerization inhibitor such as those described below could prove to be advantageous.
- the process of the invention, in particular bringing ⁇ -propiolactone into contact with the catalyst of formula (I) can also take place in one or a mixture of at least two solvent (s).
- the solvents used can be anhydrous or non-anhydrous. Solvents which can react with ⁇ -propiolactone or acrylic acid should be avoided.
- the solvent may be chosen from: - ethers, linear or cyclic, chosen from the group consisting of diethyl ether, dibutyl ether, THF, 2-methyl THF, dioxane and diglyme; - esters, linear or cyclic, chosen from the group consisting of methyl acetate, ethyl acetate, propyl ketate, isopropyl acetate, n-butyl acetate, acetate isobutyl, ethyl lactate, ⁇ -butyrolactone, dimethyl adipate, dimethyl glutarate, dimethyl succinate; - ketones, linear or cyclic ⁇ -butyrolactone s, chosen from the group consisting of acetone or propanone, butanone or methyl ethyl ketone, 4-methyl-2-pentanone or methylisobutyl ketone, acetophenone or phenylmethyl ketone,
- the solvent can be chosen from: - ethers, linear or cyclic, chosen from the group consisting of diethyl ether, dibutyl ether, THF, 2-methyl THF , dioxane and diglyme; - esters, linear or cyclic, chosen from the group consisting of methyl acetate, ethyl acetate, propyl ketate, isopropyl acetate, n-butyl acetate, acetate isobutyl, ethyl lactate, ⁇ -butyrolactone, dimethyl adipate, dimethyl, dimethyl succinate; - ketones, linear or cyclic ⁇ -butyrolactone s, chosen from the group consisting of acetone or propanone, butanone or methyl ethyl ketone, 4-methyl-2-pentanone or methylisobutyl ketone, acetophenone or phenylmethyl ketone, cyclo
- the preparation process acrylic acid from ⁇ -propiolactone according to the invention is carried out under mild conditions, in particular in terms of temperature and pressure.
- the temperature at which the process of the invention is implemented is less than or equal to 100 ° C, preferably less than or equal to 80 ° C, more preferably less than or equal to 50 ° C. More particularly, the temperature can be between 10 ° C and 80 ° C, preferably between 15 and 55 ° C, more preferably between 20 and 45 ° C.
- the implementation of the method of the invention does not require reduced pressure and can be done at atmospheric pressure.
- the process can be operated under an inert atmosphere (nitrogen, argon for example) or in air without affecting either the selectivity or the activity of the catalyst.
- the duration of the process can vary from one hour or even from a few hours to a few days, depending on the solvent, the catalyst, the amount of catalyst, the ⁇ -propiolactone concentration and the temperature. In particular, the duration can be between 1 hour and 120 hours, preferably between 1 and 80 hours, more preferably between 4 and 20 hours.
- the concentration of ⁇ -propiolactone in the reaction medium can vary from several mmol.L -1 to several mol.L -1 .
- the catalyst can be between 0.1 and 16 mol.L -1 , preferably between 0.1 and 10 mol.L -1 , more preferably between 0.1 and 5 mol.L -1 .
- the catalyst is used in a catalytic amount, that is to say in an amount less than the stoichiometric amount.
- the amount of catalyst can be between 0.01 and 20 mol%, of preferably from 0.05 to 15 mol%, more preferably from 1 to 10 mol%, relative to the lactone.
- the increase in the catalyst concentration makes it possible to reduce the reaction time.
- the presence of a catalyst at low cost, low toxicity, available in abundance and chemical simplicity is an added value compared to the catalytic systems of the state of the art.
- Acrylic acid is very reactive and capable of carrying out explosive polymerizations.
- the additive which has the role of improving the solubility of the catalyst for the transformation of ⁇ -propiolactone, can be chosen from the group consisting of: - crown ethers chosen from 12-crown-4, 15-crown -5, 18-crown-6, dibenzo-18-crown-6, benzo-18-crown-6, benzo-15-crown-5, or dibenzo-15-crown-5; - the aza-crowns chosen from 1,4,7,10-tetraazacyclodoecane (cyclene), 1,4,7,10,13,16-hexaazacyclooctadecane (hexacyclene), or diaza-18-crown-6; - Crown thioethers chosen from 1,5,9,13-tetrathiacyclohexadecane (16-Ane-S 4 ), or 1,4,7,10,13,16-hexathiacyclooctadecane (18-Ane-S6); or
- the amount of said additive in the reaction medium can be between 0.01 and 20 mol%, preferably between 0.05 and 15 mol%, more preferably between 1 and 10 mol%, relative to the lactone.
- the implementation of a method according to the invention does not need a specific reactor.
- the process for preparing acrylic acid from ⁇ -propiolactone in the presence of solvent is shown schematically in [Fig. 3].
- the process of the invention allows the preparation of acrylic acid with good yields and a selectivity at least comparable to that of the known systems.
- the only by-product present in the medium is an oligomer having polyester functions and an olefin end, generally present in the form of a dimer and / or of trimer, which allows the mixture to be used as is for subsequent applications and operations.
- an oligomer of acrylic acid for example by simple distillation. It should be noted that the oligomer could be obtained from the addition of Michael by reaction of two molecules of acrylic acid, or one molecule of acrylic acid and a reaction intermediate.
- the process of the invention does not require the presence of a polymerization inhibitor in order to obtain a high selectivity for acrylic acid, it can be envisaged to use it in order to avoid the side reactions of polymerization, and thus to conserve high selectivity.
- a polymerization inhibitor could prove to be advantageous.
- copper powder, hydroquinone, hydroquinone monomethyl ether, and phenothiazine there may be mentioned, for example, copper powder, hydroquinone, hydroquinone monomethyl ether, and phenothiazine.
- the amount of polymerization inhibitor may be greater than or equal to 20 ppm, preferably greater than or equal to 50 ppm, more preferably greater than or equal to 100 ppm, even more preferably greater than or equal to 200 ppm.
- the mild conditions developed for the process of the invention make it possible to overcome several problems concerning in particular the use of ⁇ -propiolactone as starting reagent, and the acrylic acid obtained.
- the gentle operating conditions of the process of the invention in particular in terms of temperatures, make it possible to avoid thermal decomposition of ⁇ -propiolactone (162 ° C.).
- the mild operating conditions of the process of the invention in particular in terms of temperatures, make it possible to limit the degradation of acrylic acid by the irreversible formation of a dimer by reaction of two molecules of acrylic acid. Thus, the good selectivity for the desired product is maintained.
- the method of the invention allows lower energy consumption than the methods of the state of the art.
- Another object of the invention is the use of a process for preparing acrylic acid from ⁇ -propriolactone according to the invention, in the manufacture of: - super-absorbent materials, - layers, - rubbers synthetic, - plastics, - coatings, - paints, - ink, - organic glasses, - glues, - acrylic fibers, - synthetic leathers, - pharmaceuticals, - pesticides, - d 'fertilizers, - detergents, - reagents for fine chemicals, - intermediates for the manufacture of acrylic esters, and - acrylic polymers and copolymers.
- the invention also relates to a method of manufacturing super-absorbent materials, layers, synthetic rubbers, plastics, coatings, paints, ink, organic glasses, glues, acrylic fibers, synthetic leathers. , pharmaceuticals, pesticides, fertilizers, detergents, reagents for fine chemicals, intermediates for the manufacture of acrylic esters, and acrylic polymers and copolymers, characterized in that it comprises: ( i) a step of preparing acrylic acid from ⁇ -propiolactone by the process according to the invention, and optionally (ii) a step of separating acrylic acid, for example, by distillation.
- the process of the invention can be used in the decontamination of water.
- a further subject of the invention is a process for the functionalization of technical textiles based on polypropylene (PP) intended for the decontamination of water, characterized in that it comprises a step of preparing acrylic acid from ⁇ -propiolactone by the method according to invention.
- PP polypropylene
- the use of technical textiles thus functionalized makes it possible to retain the metallic trace elements such as cadmium, chromium, lead, copper, zinc, mercury, nickel, etc., present in an aqueous medium.
- technical textile can denote a fabric, non-woven, cord, braid, etc., made up of fibers called technical fibers, having characteristics chosen for one or more well-defined applications (water pollution control for example) .
- the fibers can be, for example, carbon, glass, polyester, polypropylene, aramid, polyethylene fibers.
- EXAMPLES 1 Preparation of acrylic acid from ⁇ -propiolactone according to the process of the invention
- the various reagents and solvents used in the process of the invention and in the examples ( ⁇ -propiolactone, the catalyst, etc. ) are, in general, commercial compounds or can be prepared by any process known to those skilled in the art. 1. Under an inert atmosphere or in air, the catalyst (x mol%), the ⁇ -propiolactone (x 'mol.L -1 ) and the solvent (x''mL) are introduced into an NMR tube.
- an internal standard can be added.
- the order of introduction of the reagent, solvent, internal standard or catalyst has no influence on the reaction.
- the NMR tube is then placed at a temperature between 15 and 80 ° C. 3.
- the conversion of ⁇ -propiolactone and the yield of acrylic acid can be followed by 1 H NMR (Bruker Avance Neo 400 MHz) or GC-MS (Shimadzu GCMS-QP2010 Ultra).
- the solvents and the various reagents used in the process of the invention are, in general, commercial compounds or can be prepared by any process known to those skilled in the art. Non-anhydrous solvents can be used.
- Example 2 Potassium iodide (4.1 mg, 0.025 mmol, 0.05 eq), ⁇ -propiolactone (31 ⁇ L, 0.500 mmol, 1 eq) and acetone-d 6 (500 ⁇ L) are added in a sealed tube. Finally, mesitylene (14 ⁇ L, 0.100 mmol, 0.1 eq) is added as an internal standard. The reaction is stirred for 16 hours at 45 ° C.
- Example 3 Potassium iodide (1.0 mg, 0.006 mmol, 0.05 eq), ⁇ -propiolactone (7.75 ⁇ L, 0.125 mmol, 1 eq) and acetone-d 6 (500 ⁇ L) are added in a sealed tube.
- mesitylene (3.5 ⁇ L, 0.025 mmol, 0.1 eq) is added as an internal standard. The reaction is stirred for 16 hours at 45 ° C.
- Example 4 Potassium iodide (4.1 mg, 0.025 mmol, 0.05 eq), crown ether 18-c-6 (6.6 mg, 0.025 mmol, 0.05 eq), ⁇ - propiolactone (31 ⁇ L, 0.500 mmol, 1 eq.) and acetone-d 6 (500 ⁇ L) are added in a sealed tube. Finally, mesitylene (14 ⁇ L, 0.100 mmol, 0.1 eq) is added as an internal standard. The reaction is stirred for 16 hours at 45 ° C.
- Example 5 Potassium iodide (41 mg, 0.25 mmol, 0.05 eq), ⁇ -propiolactone (310 ⁇ L, 5 mmol, 1 eq) and acetone-d6 (5 mL) are added to a single-neck balloon. Finally, mesitylene (14 ⁇ L, 0.100 mmol, 0.1 eq) is added as an internal standard. The reaction is stirred for 10 hours at 45 ° C. for a conversion of 99% with a selectivity of 73%. 2. Influence of the various parameters on the production of acrylic acid 2.1. Solvent test The influence of the solvent on the production of acrylic acid was studied.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2005098A FR3110570B1 (en) | 2020-05-19 | 2020-05-19 | METHOD FOR THE PREPARATION OF ACRYLIC ACID FROM β-PROPIOLACTONE |
PCT/EP2021/063014 WO2021233839A1 (en) | 2020-05-19 | 2021-05-17 | METHOD FOR PREPARING ACRYLIC ACID FROM β-PROPIOLACTONE |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4153556A1 true EP4153556A1 (en) | 2023-03-29 |
Family
ID=72178727
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP21725208.9A Pending EP4153556A1 (en) | 2020-05-19 | 2021-05-17 | Method for preparing acrylic acid from beta-propiolactone |
Country Status (5)
Country | Link |
---|---|
US (1) | US20230192585A1 (en) |
EP (1) | EP4153556A1 (en) |
JP (1) | JP2023526331A (en) |
FR (1) | FR3110570B1 (en) |
WO (1) | WO2021233839A1 (en) |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3176042A (en) | 1959-10-20 | 1965-03-30 | Celanese Corp | Treating propiolactone with heated phosphoric acid to produce acrylic acid |
WO2012156921A1 (en) | 2011-05-16 | 2012-11-22 | Council Of Scientific & Industrial Research | An improved process for catalytic dehydration of lactic acid to acrylic acid |
MY189275A (en) | 2012-02-22 | 2022-01-31 | Novomer Inc | Acrylic acid production methods |
US10106484B2 (en) | 2012-04-11 | 2018-10-23 | The Procter & Gamble Company | Catalysts for the conversion of hydroxypropionic acid or its derivatives to acrylic acid or its derivatives |
DE102013210840A1 (en) * | 2013-06-11 | 2014-12-11 | Evonik Industries Ag | Synthesis of α, β-unsaturated carboxylic acids (meth) acrylates from olefins and CO2 |
BR112018069019A2 (en) | 2016-03-21 | 2019-01-22 | Novomer Inc | acrylic acid and production methods |
US10307744B2 (en) | 2016-07-29 | 2019-06-04 | The Procter & Gamble Company | Catalysts for making acrylic acid from lactic acid or its derivatives in liquid phase |
-
2020
- 2020-05-19 FR FR2005098A patent/FR3110570B1/en active Active
-
2021
- 2021-05-17 JP JP2022569522A patent/JP2023526331A/en active Pending
- 2021-05-17 US US17/926,107 patent/US20230192585A1/en active Pending
- 2021-05-17 EP EP21725208.9A patent/EP4153556A1/en active Pending
- 2021-05-17 WO PCT/EP2021/063014 patent/WO2021233839A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
WO2021233839A1 (en) | 2021-11-25 |
FR3110570A1 (en) | 2021-11-26 |
US20230192585A1 (en) | 2023-06-22 |
FR3110570B1 (en) | 2022-05-20 |
JP2023526331A (en) | 2023-06-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10745369B2 (en) | Processes for producing 2,5-furandicarboxylic acid and derivatives thereof and polymers made therefrom | |
CA2902493C (en) | Process for making 2,5-furandicarboxylic acid | |
US8609895B2 (en) | Process for the oxidation of alcohol and/or aldehyde groups | |
EP2365964B1 (en) | Method for manufacturing compounds including nitrile functions | |
EP3604290B1 (en) | Furan monomer having bifunctional hydroxymethyl group and preparation method therefor | |
EP2791124B1 (en) | Method for manufacturing compounds including nitrile functions | |
EA025474B1 (en) | Process to produce valerolactone from levulinic acid | |
US10081611B2 (en) | Method for acid-catalyzed acylation of the reduction products of 5-hydroxymethyl furfural | |
FR2977586A1 (en) | PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRIL FUNCTIONS | |
FR3008409A1 (en) | PROCESS FOR THE PRODUCTION OF 2,5-DICARBOXALDEHYDE FURANE FROM HYDROXYMETHYLFURFURAL AND HALOGENATED DERIVATIVES NOT USING METAL CATALYST | |
EP4153556A1 (en) | Method for preparing acrylic acid from beta-propiolactone | |
CA3199380A1 (en) | Improved method for recycling pet by alcoholysis | |
JP5076313B2 (en) | Process for producing purified 2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester and intermediate thereof | |
BE1029669B1 (en) | Process for the preparation of acrylic acid or acrylic acid ester by catalytic dehydration from a recycle stream of a process for the production of polylactic acid | |
CN115197116B (en) | Preparation method of N-phenylmaleimide | |
JP2019043922A (en) | Method for producing composition derived from ester compound using acid |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20221115 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20231012 |