CA3221040A1 - Technologies ramifiees - Google Patents
Technologies ramifiees Download PDFInfo
- Publication number
- CA3221040A1 CA3221040A1 CA3221040A CA3221040A CA3221040A1 CA 3221040 A1 CA3221040 A1 CA 3221040A1 CA 3221040 A CA3221040 A CA 3221040A CA 3221040 A CA3221040 A CA 3221040A CA 3221040 A1 CA3221040 A1 CA 3221040A1
- Authority
- CA
- Canada
- Prior art keywords
- branched
- mixture
- alcohols
- product
- composition
- 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
- 238000005516 engineering process Methods 0.000 title description 17
- 150000001298 alcohols Chemical class 0.000 claims abstract description 394
- 238000000034 method Methods 0.000 claims abstract description 212
- 230000008569 process Effects 0.000 claims abstract description 186
- 239000004094 surface-active agent Substances 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims description 861
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 228
- -1 2-ethyl Chemical group 0.000 claims description 157
- 150000002148 esters Chemical class 0.000 claims description 60
- 150000001735 carboxylic acids Chemical class 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 15
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 230000001180 sulfating effect Effects 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 10
- 125000003158 alcohol group Chemical group 0.000 claims description 9
- 150000005690 diesters Chemical class 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 abstract description 684
- 150000001336 alkenes Chemical class 0.000 abstract description 226
- 238000006317 isomerization reaction Methods 0.000 abstract description 120
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 116
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 74
- 238000006243 chemical reaction Methods 0.000 abstract description 47
- 239000000047 product Substances 0.000 description 366
- 239000003054 catalyst Substances 0.000 description 278
- 239000004711 α-olefin Substances 0.000 description 265
- 239000010948 rhodium Substances 0.000 description 154
- 229910052703 rhodium Inorganic materials 0.000 description 142
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 141
- 239000003446 ligand Substances 0.000 description 135
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 127
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 115
- 229910002091 carbon monoxide Inorganic materials 0.000 description 114
- 238000004821 distillation Methods 0.000 description 94
- 150000001412 amines Chemical class 0.000 description 77
- 239000007795 chemical reaction product Substances 0.000 description 67
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 51
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 50
- 125000002524 organometallic group Chemical group 0.000 description 49
- 239000000126 substance Substances 0.000 description 47
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 43
- 239000012298 atmosphere Substances 0.000 description 41
- 238000004519 manufacturing process Methods 0.000 description 39
- 238000010977 unit operation Methods 0.000 description 38
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 36
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 36
- 239000001257 hydrogen Substances 0.000 description 34
- 229910052739 hydrogen Inorganic materials 0.000 description 34
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 32
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 30
- 238000011084 recovery Methods 0.000 description 27
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 25
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical class CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 23
- PPJRQOPBVSCJCN-UHFFFAOYSA-N 2-ethylundecanal Chemical compound CCCCCCCCCC(CC)C=O PPJRQOPBVSCJCN-UHFFFAOYSA-N 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 229940069096 dodecene Drugs 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- MCGQXFHGPRZIFZ-UHFFFAOYSA-N 2-ethyltridecanal Chemical group CCCCCCCCCCCC(CC)C=O MCGQXFHGPRZIFZ-UHFFFAOYSA-N 0.000 description 19
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 19
- KQKICLRRTKEFJT-UHFFFAOYSA-N 2-ethyltridecan-1-ol Chemical compound CCCCCCCCCCCC(CC)CO KQKICLRRTKEFJT-UHFFFAOYSA-N 0.000 description 18
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 229910017052 cobalt Inorganic materials 0.000 description 17
- 239000010941 cobalt Substances 0.000 description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 17
- OVNMDGHHVKQVQA-UHFFFAOYSA-N 2-ethylundecan-1-ol Chemical compound CCCCCCCCCC(CC)CO OVNMDGHHVKQVQA-UHFFFAOYSA-N 0.000 description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 16
- 230000008901 benefit Effects 0.000 description 16
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical class CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 11
- 239000012442 inert solvent Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- ISZREKMLQKLUDD-UHFFFAOYSA-N 2-methyldodecanal Chemical compound CCCCCCCCCCC(C)C=O ISZREKMLQKLUDD-UHFFFAOYSA-N 0.000 description 9
- 239000000314 lubricant Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 8
- 229920013639 polyalphaolefin Polymers 0.000 description 8
- MJHNFOWITPQFBW-UHFFFAOYSA-N 2-methyltetradecanal Chemical group CCCCCCCCCCCCC(C)C=O MJHNFOWITPQFBW-UHFFFAOYSA-N 0.000 description 7
- BMYWYGFRNQXKDP-UHFFFAOYSA-N 2-propyldodecanal Chemical compound CCCCCCCCCCC(C=O)CCC BMYWYGFRNQXKDP-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- XARVANDLQOZMMJ-CHHVJCJISA-N 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-oxo-2-(2-oxoethylamino)ethylidene]amino]oxy-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)O\N=C(/C(=O)NCC=O)C1=CSC(N)=N1 XARVANDLQOZMMJ-CHHVJCJISA-N 0.000 description 6
- CGTBUYCHHZHYBU-UHFFFAOYSA-N 2-methyltetradecan-1-ol Chemical compound CCCCCCCCCCCCC(C)CO CGTBUYCHHZHYBU-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WRHQJRQYHZNETJ-UHFFFAOYSA-N 2-propyldecanal Chemical compound CCCCCCCCC(C=O)CCC WRHQJRQYHZNETJ-UHFFFAOYSA-N 0.000 description 5
- 239000010953 base metal Substances 0.000 description 5
- SUCYXRASDBOYGB-UHFFFAOYSA-N cobalt rhodium Chemical compound [Co].[Rh] SUCYXRASDBOYGB-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000010970 precious metal Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- NWUCYANQRMAJJA-UHFFFAOYSA-N 2-butylnonanal Chemical compound CCCCCCCC(C=O)CCCC NWUCYANQRMAJJA-UHFFFAOYSA-N 0.000 description 4
- SCHAAFQMJJWGJM-UHFFFAOYSA-N 2-methyldodecan-1-ol Chemical compound CCCCCCCCCCC(C)CO SCHAAFQMJJWGJM-UHFFFAOYSA-N 0.000 description 4
- FYDUJOZFUFRISC-UHFFFAOYSA-N 2-pentyloctanal Chemical compound CCCCCCC(C=O)CCCCC FYDUJOZFUFRISC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000003879 lubricant additive Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000010215 titanium dioxide Nutrition 0.000 description 4
- QCOAIZCMIUWLAO-UHFFFAOYSA-N 2-hexylnonanal Chemical compound CCCCCCCC(C=O)CCCCCC QCOAIZCMIUWLAO-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- PIYDVAYKYBWPPY-UHFFFAOYSA-N heptadecanal Chemical class CCCCCCCCCCCCCCCCC=O PIYDVAYKYBWPPY-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical class CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical class CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 3
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- BNTLPYDMDDEHHD-UHFFFAOYSA-N 2-butylnonan-1-ol Chemical compound CCCCCCCC(CO)CCCC BNTLPYDMDDEHHD-UHFFFAOYSA-N 0.000 description 2
- YZEGZZUYINZQHB-UHFFFAOYSA-N 2-butylundecanal Chemical compound CCCCCCCCCC(C=O)CCCC YZEGZZUYINZQHB-UHFFFAOYSA-N 0.000 description 2
- RDVXPVLRPMHRBN-UHFFFAOYSA-N 2-propyldecan-1-ol Chemical compound CCCCCCCCC(CO)CCC RDVXPVLRPMHRBN-UHFFFAOYSA-N 0.000 description 2
- KRAVTZSBXJSGFH-UHFFFAOYSA-N 2-propyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCC KRAVTZSBXJSGFH-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 229910001119 inconels 625 Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 2
- HGEMCUOAMCILCP-UHFFFAOYSA-N isotridecane Natural products CCCCCCCCCCC(C)C HGEMCUOAMCILCP-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ADOQBZAVKYCFOI-HWKANZROSA-N (E)-2-dodecene Chemical compound CCCCCCCCC\C=C\C ADOQBZAVKYCFOI-HWKANZROSA-N 0.000 description 1
- WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 1
- MQCPPZLYNIKBNK-UHFFFAOYSA-N 2-butylundecan-1-ol Chemical compound CCCCCCCCCC(CO)CCCC MQCPPZLYNIKBNK-UHFFFAOYSA-N 0.000 description 1
- GNFCYNVMPBEXSR-UHFFFAOYSA-N 2-pentyldecan-1-ol Chemical compound CCCCCCCCC(CO)CCCCC GNFCYNVMPBEXSR-UHFFFAOYSA-N 0.000 description 1
- HSZDCONVHXPTFQ-UHFFFAOYSA-N 2-pentyldecanal Chemical compound CCCCCCCCC(C=O)CCCCC HSZDCONVHXPTFQ-UHFFFAOYSA-N 0.000 description 1
- SPFBHWHDOHCHHB-UHFFFAOYSA-N 2-pentyloctan-1-ol Chemical compound CCCCCCC(CO)CCCCC SPFBHWHDOHCHHB-UHFFFAOYSA-N 0.000 description 1
- HXUYUZCPGPKNGS-UHFFFAOYSA-N 3-Methyltetradecane Chemical compound CCCCCCCCCCCC(C)CC HXUYUZCPGPKNGS-UHFFFAOYSA-N 0.000 description 1
- UZTXSMATBUWDDZ-UHFFFAOYSA-N 4-methyldodecane Chemical compound CCCCCCCCC(C)CCC UZTXSMATBUWDDZ-UHFFFAOYSA-N 0.000 description 1
- ONQXEQPEKDADGM-UHFFFAOYSA-N 6-methyltetradecane Chemical compound CCCCCCCCC(C)CCCCC ONQXEQPEKDADGM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SXIYYZWCMUFWBW-UHFFFAOYSA-N Nonadecanal Chemical compound CCCCCCCCCCCCCCCCCCC=O SXIYYZWCMUFWBW-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CLNGVCNNXPOBQG-UHFFFAOYSA-N [Co+2].CCCCCC(=O)OCC Chemical compound [Co+2].CCCCCC(=O)OCC CLNGVCNNXPOBQG-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002382 heptanals Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- YFKIWUQBRSMPMZ-UHFFFAOYSA-N methane;nickel Chemical compound C.[Ni] YFKIWUQBRSMPMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical group CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical class CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne un procédé de production d'oléfines isomérisées, d'aldéhydes ramifiés, d'alcools ramifiés, de tensioactifs ramifiés et d'autres dérivés ramifiés par des réactions d'isomérisation, d'hydroformylation, d'hydrogénation, de formation de tensioactifs et d'autres réactions de formation de dérivés.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163196679P | 2021-06-03 | 2021-06-03 | |
| US63/196,679 | 2021-06-03 | ||
| US17/541,235 US20220194886A1 (en) | 2020-12-17 | 2021-12-02 | Branched Products |
| US17/541,235 | 2021-12-02 | ||
| US17/553,427 US11993565B2 (en) | 2021-12-16 | Branched products | |
| USPCT/US2021/063934 | 2021-12-16 | ||
| PCT/US2021/063934 WO2022133157A1 (fr) | 2020-12-17 | 2021-12-16 | Technologie de ramification |
| US17/553,427 | 2021-12-16 | ||
| PCT/US2022/031481 WO2022256272A1 (fr) | 2021-06-03 | 2022-05-29 | Technologies ramifiées |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3221040A1 true CA3221040A1 (fr) | 2022-12-08 |
Family
ID=84324441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3221040A Pending CA3221040A1 (fr) | 2021-06-03 | 2022-05-29 | Technologies ramifiees |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4347770A1 (fr) |
| CA (1) | CA3221040A1 (fr) |
| WO (1) | WO2022256272A1 (fr) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9524488D0 (en) * | 1995-11-30 | 1996-01-31 | Unilever Plc | Detergent compositions containing soil release polymers |
| BR112012004297A2 (pt) * | 2009-08-27 | 2017-05-30 | Otc Gmbh | concentrado perolado e método para a fabricação do mesmo. |
| US20170051195A1 (en) * | 2015-08-21 | 2017-02-23 | Cytec Industries Inc. | Surfactant Compositions |
| US20210387933A1 (en) * | 2020-06-05 | 2021-12-16 | SCION Holdings LLC | Branched Products |
-
2022
- 2022-05-29 WO PCT/US2022/031481 patent/WO2022256272A1/fr active Application Filing
- 2022-05-29 EP EP22816694.8A patent/EP4347770A1/fr active Pending
- 2022-05-29 CA CA3221040A patent/CA3221040A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022256272A1 (fr) | 2022-12-08 |
| EP4347770A1 (fr) | 2024-04-10 |
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