CA2648012C - Cetamides, methodes pour les produire et leurs applications - Google Patents

Info

Publication number

CA2648012C

CA2648012C CA 2648012 CA2648012A CA2648012C CA 2648012 C CA2648012 C CA 2648012C CA 2648012 CA2648012 CA 2648012 CA 2648012 A CA2648012 A CA 2648012A CA 2648012 C CA2648012 C CA 2648012C

Authority

CA

Canada

Prior art keywords

compound

group

amide

flask

cndot

Prior art date

2008-04-16

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.)

Expired - Fee Related

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• -1 amide compounds Chemical class 0.000 title claims abstract description 212
• 238000000034 method Methods 0.000 title abstract description 109
• 150000001875 compounds Chemical class 0.000 claims abstract description 373
• 239000000203 mixture Substances 0.000 claims abstract description 89
• 150000002148 esters Chemical class 0.000 claims abstract description 83
• 150000001412 amines Chemical class 0.000 claims abstract description 32
• 238000009472 formulation Methods 0.000 claims abstract description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 367
• 150000001408 amides Chemical class 0.000 claims description 244
• 229910052757 nitrogen Inorganic materials 0.000 claims description 184
• 229920000642 polymer Polymers 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 96
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 90
• WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 85
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 239000001257 hydrogen Substances 0.000 claims description 81
• 125000005842 heteroatom Chemical group 0.000 claims description 75
• 125000003342 alkenyl group Chemical group 0.000 claims description 67
• 125000000304 alkynyl group Chemical group 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 150000004985 diamines Chemical class 0.000 claims description 58
• 125000004432 carbon atom Chemical group C* 0.000 claims description 50
• 125000005442 diisocyanate group Chemical group 0.000 claims description 45
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 44
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 150000002009 diols Chemical class 0.000 claims description 41
• 125000006165 cyclic alkyl group Chemical group 0.000 claims description 37
• 125000005647 linker group Chemical group 0.000 claims description 36
• 238000006116 polymerization reaction Methods 0.000 claims description 34
• 229920000728 polyester Polymers 0.000 claims description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
• 150000005690 diesters Chemical class 0.000 claims description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 239000002904 solvent Substances 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
• 229910019142 PO4 Inorganic materials 0.000 claims description 18
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 18
• 239000010452 phosphate Substances 0.000 claims description 18
• 239000004094 surface-active agent Substances 0.000 claims description 18
• 229920002635 polyurethane Polymers 0.000 claims description 17
• 239000004814 polyurethane Substances 0.000 claims description 17
• 239000012634 fragment Substances 0.000 claims description 16
• 125000000524 functional group Chemical group 0.000 claims description 15
• 239000004014 plasticizer Substances 0.000 claims description 14
• 229920000515 polycarbonate Polymers 0.000 claims description 14
• 239000004417 polycarbonate Substances 0.000 claims description 14
• 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 229920001634 Copolyester Polymers 0.000 claims description 11
• 239000004698 Polyethylene Substances 0.000 claims description 11
• 229920002873 Polyethylenimine Polymers 0.000 claims description 11
• GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
• 150000004662 dithiols Chemical class 0.000 claims description 11
• 229920000573 polyethylene Polymers 0.000 claims description 11
• 229920002396 Polyurea Polymers 0.000 claims description 10
• 150000008064 anhydrides Chemical class 0.000 claims description 10
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 10
• ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 9
• 239000004604 Blowing Agent Substances 0.000 claims description 9
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
• 239000000194 fatty acid Substances 0.000 claims description 9
• 229930195729 fatty acid Natural products 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000001749 primary amide group Chemical group 0.000 claims description 9
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000005741 alkyl alkenyl group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 150000003949 imides Chemical class 0.000 claims description 8
• 239000003607 modifier Substances 0.000 claims description 8
• 229910052698 phosphorus Inorganic materials 0.000 claims description 8
• 239000011574 phosphorus Substances 0.000 claims description 8
• 229910052710 silicon Inorganic materials 0.000 claims description 8
• 239000010703 silicon Substances 0.000 claims description 8
• YIKQLNRXIWIZFA-UHFFFAOYSA-N silyl dihydrogen phosphate Chemical compound OP(O)(=O)O[SiH3] YIKQLNRXIWIZFA-UHFFFAOYSA-N 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 150000003457 sulfones Chemical class 0.000 claims description 8
• IKRMQEUTISXXQP-UHFFFAOYSA-N tetrasulfane Chemical compound SSSS IKRMQEUTISXXQP-UHFFFAOYSA-N 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 7
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• 229920002554 vinyl polymer Polymers 0.000 claims description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
• 239000005864 Sulphur Substances 0.000 claims description 6
• 239000003999 initiator Substances 0.000 claims description 6
• 239000002667 nucleating agent Substances 0.000 claims description 6
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
• HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 5
• 238000012546 transfer Methods 0.000 claims description 5
• 239000000853 adhesive Substances 0.000 claims description 4
• 230000001070 adhesive effect Effects 0.000 claims description 4
• 239000006184 cosolvent Substances 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 229920002959 polymer blend Polymers 0.000 claims description 2
• 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
• 238000006243 chemical reaction Methods 0.000 abstract description 143
• 239000002253 acid Substances 0.000 abstract description 29
• 150000007513 acids Chemical class 0.000 abstract description 12
• 239000003921 oil Substances 0.000 description 125
• 235000019198 oils Nutrition 0.000 description 124
• 229920001855 polyketal Polymers 0.000 description 121
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 64
• 229920002647 polyamide Polymers 0.000 description 59
• 239000004952 Polyamide Substances 0.000 description 56
• 238000000113 differential scanning calorimetry Methods 0.000 description 51
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 48
• 239000002243 precursor Substances 0.000 description 48
• 230000015572 biosynthetic process Effects 0.000 description 47
• 239000007788 liquid Substances 0.000 description 40
• 229910052720 vanadium Inorganic materials 0.000 description 40
• 229920001577 copolymer Polymers 0.000 description 37
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 35
• 238000003786 synthesis reaction Methods 0.000 description 35
• 229920000768 polyamine Polymers 0.000 description 34
• 239000003054 catalyst Substances 0.000 description 33
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 31
• 229920001228 polyisocyanate Polymers 0.000 description 31
• 239000005056 polyisocyanate Substances 0.000 description 31
• 229920005862 polyol Polymers 0.000 description 31
• 150000003077 polyols Chemical class 0.000 description 31
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• 238000005227 gel permeation chromatography Methods 0.000 description 30
• 238000011049 filling Methods 0.000 description 29
• 238000007872 degassing Methods 0.000 description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 27
• 238000007792 addition Methods 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 24
• 239000007787 solid Substances 0.000 description 24
• 239000007795 chemical reaction product Substances 0.000 description 23
• JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 22
• 229920001002 functional polymer Polymers 0.000 description 22
• 239000012948 isocyanate Substances 0.000 description 22
• 239000000463 material Substances 0.000 description 22
• 239000010936 titanium Substances 0.000 description 22
• 238000007098 aminolysis reaction Methods 0.000 description 21
• WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 21
• 150000002513 isocyanates Chemical class 0.000 description 21
• 238000000576 coating method Methods 0.000 description 20
• 239000007858 starting material Substances 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 235000013877 carbamide Nutrition 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
• 238000004458 analytical method Methods 0.000 description 17
• 125000004122 cyclic group Chemical group 0.000 description 17
• 239000010408 film Substances 0.000 description 17
• 230000009477 glass transition Effects 0.000 description 16
• 239000004202 carbamide Substances 0.000 description 14
• 125000004185 ester group Chemical group 0.000 description 14
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 14
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• 150000003573 thiols Chemical class 0.000 description 13
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 12
• 238000004132 cross linking Methods 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 229940040102 levulinic acid Drugs 0.000 description 11
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
• 229920002472 Starch Polymers 0.000 description 10
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• 239000000306 component Substances 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• 238000007151 ring opening polymerisation reaction Methods 0.000 description 10
• 235000019698 starch Nutrition 0.000 description 10
• UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 9
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
• 239000011248 coating agent Substances 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 239000000835 fiber Substances 0.000 description 9
• 239000006260 foam Substances 0.000 description 9
• 239000000178 monomer Substances 0.000 description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 description 9
• 239000004386 Erythritol Substances 0.000 description 8
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
• 238000007796 conventional method Methods 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 238000005516 engineering process Methods 0.000 description 8
• UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 8
• 229940009714 erythritol Drugs 0.000 description 8
• 235000019414 erythritol Nutrition 0.000 description 8
• 150000002402 hexoses Chemical class 0.000 description 8
• 150000002734 metacrylic acid derivatives Chemical class 0.000 description 8
• 125000000466 oxiranyl group Chemical group 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 230000009257 reactivity Effects 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 8
• 239000008107 starch Substances 0.000 description 8
• 238000005809 transesterification reaction Methods 0.000 description 8
• GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 7
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
• 125000001931 aliphatic group Chemical group 0.000 description 7
• 229920002678 cellulose Polymers 0.000 description 7
• 230000003247 decreasing effect Effects 0.000 description 7
• 238000004817 gas chromatography Methods 0.000 description 7
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 7
• 150000002596 lactones Chemical class 0.000 description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
• 150000003839 salts Chemical class 0.000 description 7
• 238000007056 transamidation reaction Methods 0.000 description 7
• MQDLKAADJTYKRH-UHFFFAOYSA-N 1-aminopropane-1,2,3-triol Chemical compound NC(O)C(O)CO MQDLKAADJTYKRH-UHFFFAOYSA-N 0.000 description 6
• FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 6
• WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 6
• RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
• 150000001241 acetals Chemical class 0.000 description 6
• 239000006227 byproduct Substances 0.000 description 6
• 235000010980 cellulose Nutrition 0.000 description 6
• WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 6
• 150000002430 hydrocarbons Chemical group 0.000 description 6
• 238000005259 measurement Methods 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• 229940107700 pyruvic acid Drugs 0.000 description 6
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
• 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 6
• QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 6
• 150000004072 triols Chemical class 0.000 description 6
• 239000003643 water by type Substances 0.000 description 6
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 125000000746 allylic group Chemical group 0.000 description 5
• 239000001569 carbon dioxide Substances 0.000 description 5
• 229910002092 carbon dioxide Inorganic materials 0.000 description 5
• 230000015556 catabolic process Effects 0.000 description 5
• 239000001913 cellulose Substances 0.000 description 5
• 239000002131 composite material Substances 0.000 description 5
• 238000006731 degradation reaction Methods 0.000 description 5
• 235000013305 food Nutrition 0.000 description 5
• 230000000670 limiting effect Effects 0.000 description 5
• 230000000704 physical effect Effects 0.000 description 5
• 229920003023 plastic Polymers 0.000 description 5
• 239000004033 plastic Substances 0.000 description 5
• 238000012545 processing Methods 0.000 description 5
• 238000010926 purge Methods 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 150000007970 thio esters Chemical class 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• 238000005160 1H NMR spectroscopy Methods 0.000 description 4
• KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
• GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000004677 Nylon Substances 0.000 description 4
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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