CA2871428A1 - Unsaturated fatty alcohol compositions and derivatives from natural oil metathesis - Google Patents
Unsaturated fatty alcohol compositions and derivatives from natural oil metathesis Download PDFInfo
- Publication number
- CA2871428A1 CA2871428A1 CA2871428A CA2871428A CA2871428A1 CA 2871428 A1 CA2871428 A1 CA 2871428A1 CA 2871428 A CA2871428 A CA 2871428A CA 2871428 A CA2871428 A CA 2871428A CA 2871428 A1 CA2871428 A1 CA 2871428A1
- Authority
- CA
- Canada
- Prior art keywords
- oil
- metathesis
- unsaturated
- derived
- hydrocarbyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 238000005649 metathesis reaction Methods 0.000 title claims abstract description 58
- 150000002191 fatty alcohols Chemical class 0.000 title description 44
- 150000002148 esters Chemical class 0.000 claims abstract description 58
- -1 silane compound Chemical class 0.000 claims abstract description 56
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 38
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 229910000077 silane Inorganic materials 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000003921 oil Substances 0.000 claims description 51
- 235000019198 oils Nutrition 0.000 claims description 50
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 34
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 150000001336 alkenes Chemical class 0.000 claims description 26
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 22
- 125000005907 alkyl ester group Chemical group 0.000 claims description 16
- 238000005686 cross metathesis reaction Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- SBIGSHCJXYGFMX-UHFFFAOYSA-N methyl dec-9-enoate Chemical compound COC(=O)CCCCCCCC=C SBIGSHCJXYGFMX-UHFFFAOYSA-N 0.000 claims description 13
- DUWQEMMRMJGHSA-UHFFFAOYSA-N methyl dodec-9-enoate Chemical compound CCC=CCCCCCCCC(=O)OC DUWQEMMRMJGHSA-UHFFFAOYSA-N 0.000 claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 9
- 235000012424 soybean oil Nutrition 0.000 claims description 9
- 239000003549 soybean oil Substances 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 239000012279 sodium borohydride Substances 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
- GJNNIRNIXNLOJP-ONEGZZNKSA-N 9-Dodecen-1-ol Chemical compound CC\C=C\CCCCCCCCO GJNNIRNIXNLOJP-ONEGZZNKSA-N 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 235000019482 Palm oil Nutrition 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 6
- 239000002540 palm oil Substances 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 229910052793 cadmium Inorganic materials 0.000 claims description 5
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 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 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- 229910010277 boron hydride Inorganic materials 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000292 calcium oxide Substances 0.000 claims description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000828 canola oil Substances 0.000 claims description 3
- 235000019519 canola oil Nutrition 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 235000019197 fats Nutrition 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002642 lithium compounds Chemical class 0.000 claims description 3
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 3
- 150000002681 magnesium compounds Chemical class 0.000 claims description 3
- 125000005609 naphthenate group Chemical group 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003346 palm kernel oil Substances 0.000 claims description 3
- 235000019865 palm kernel oil Nutrition 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 230000026731 phosphorylation Effects 0.000 claims description 3
- 238000006366 phosphorylation reaction Methods 0.000 claims description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 150000005691 triesters Chemical class 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 235000019489 Almond oil Nutrition 0.000 claims description 2
- 241000221089 Jatropha Species 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 240000008488 Thlaspi arvense Species 0.000 claims description 2
- 235000008214 Thlaspi arvense Nutrition 0.000 claims description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000008168 almond oil Substances 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 239000010636 coriander oil Substances 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 238000005858 glycosidation reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 239000008164 mustard oil Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 244000144977 poultry Species 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 235000011803 sesame oil Nutrition 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 239000010497 wheat germ oil Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 2
- 239000012312 sodium hydride Substances 0.000 claims 2
- 150000001719 carbohydrate derivatives Chemical class 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000314 lubricant Substances 0.000 abstract description 18
- 239000000654 additive Substances 0.000 abstract description 13
- 239000012530 fluid Substances 0.000 abstract description 12
- 239000000446 fuel Substances 0.000 abstract description 8
- 239000000853 adhesive Substances 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 239000004033 plastic Substances 0.000 abstract description 6
- 229920003023 plastic Polymers 0.000 abstract description 6
- 239000004014 plasticizer Substances 0.000 abstract description 6
- 239000010426 asphalt Substances 0.000 abstract description 5
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 4
- 239000011369 resultant mixture Substances 0.000 abstract description 3
- 239000013538 functional additive Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 34
- 150000001298 alcohols Chemical class 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000003599 detergent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 7
- 150000002194 fatty esters Chemical class 0.000 description 7
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000005872 self-metathesis reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000003158 alcohol group Chemical group 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000011984 grubbs catalyst Substances 0.000 description 5
- 229940073769 methyl oleate Drugs 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 238000006845 Michael addition reaction Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical class 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- GJNNIRNIXNLOJP-UHFFFAOYSA-N dodec-9-en-1-ol Chemical compound CCC=CCCCCCCCCO GJNNIRNIXNLOJP-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000010440 gypsum Substances 0.000 description 3
- 229910052602 gypsum Inorganic materials 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
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- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- PEVGWZNVQRMBJY-UHFFFAOYSA-N nonadec-10-en-2-ol Chemical compound CCCCCCCCC=CCCCCCCCC(C)O PEVGWZNVQRMBJY-UHFFFAOYSA-N 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- SECPZKHBENQXJG-BQYQJAHWSA-N palmitelaidic acid Chemical compound CCCCCC\C=C\CCCCCCCC(O)=O SECPZKHBENQXJG-BQYQJAHWSA-N 0.000 description 1
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- 150000008300 phosphoramidites Chemical class 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 239000003784 tall oil Substances 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- FKLSONDBCYHMOQ-ONEGZZNKSA-N trans-dodec-9-enoic acid Chemical compound CC\C=C\CCCCCCCC(O)=O FKLSONDBCYHMOQ-ONEGZZNKSA-N 0.000 description 1
- HSNQNPCNYIJJHT-ISLYRVAYSA-N trans-octadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCC HSNQNPCNYIJJHT-ISLYRVAYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- KIWIPIAOWPKUNM-UHFFFAOYSA-N tridec-9-enoic acid Chemical compound CCCC=CCCCCCCCC(O)=O KIWIPIAOWPKUNM-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- JOHIXGUTSXXADV-UHFFFAOYSA-N undec-2-ene Chemical class CCCCCCCCC=CC JOHIXGUTSXXADV-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/04—Acyclic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
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| US201261637574P | 2012-04-24 | 2012-04-24 | |
| US61/637,574 | 2012-04-24 | ||
| US201361780490P | 2013-03-13 | 2013-03-13 | |
| US61/780,490 | 2013-03-13 | ||
| PCT/US2013/037568 WO2013163071A1 (en) | 2012-04-24 | 2013-04-22 | Unsaturated fatty alcohol compositions and derivatives from natural oil metathesis |
Publications (1)
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| CA2871428A1 true CA2871428A1 (en) | 2013-10-31 |
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| CA2871428A Abandoned CA2871428A1 (en) | 2012-04-24 | 2013-04-22 | Unsaturated fatty alcohol compositions and derivatives from natural oil metathesis |
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| US (2) | US20130281688A1 (enExample) |
| EP (1) | EP2841407A1 (enExample) |
| CN (1) | CN104271542A (enExample) |
| CA (1) | CA2871428A1 (enExample) |
| IN (1) | IN2014DN08906A (enExample) |
| WO (1) | WO2013163071A1 (enExample) |
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| IN2014KN02369A (enExample) | 2012-04-24 | 2015-05-01 | Stepan Co | |
| AU2013252873B2 (en) | 2012-04-24 | 2016-04-21 | Stepan Company | Unsaturated fatty alcohol derivatives from natural oil metathesis |
| WO2015108874A1 (en) * | 2014-01-16 | 2015-07-23 | Elevance Renewable Sciences, Inc. | Olefinic ester compositions and their use in oil- and gas-related applications |
| US11053430B2 (en) | 2014-01-16 | 2021-07-06 | Wilmar Trading Pte Ltd. | Olefinic ester compositions and their use in stimulating hydrocarbon production from a subterranean formation |
| US10759990B2 (en) | 2014-01-16 | 2020-09-01 | Wilmar Trading Pte Ltd. | Use of olefinic ester compositions in oil and gas fields |
| US10081760B2 (en) | 2014-01-16 | 2018-09-25 | Elevance Renewable Sciences, Inc. | Olefinic ester compositions and their use in stimulating hydrocarbon production from a subterranean formation |
| ES2590220B1 (es) | 2015-05-18 | 2017-12-18 | Neol Biosolutions, S.A. | Producción de aceites microbianos con alto contenido en acido oleico |
| WO2017087710A2 (en) | 2015-11-18 | 2017-05-26 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
| JP6737885B2 (ja) | 2015-11-18 | 2020-08-12 | プロヴィヴィ インコーポレイテッド | 昆虫フェロモンの生成のための微生物及び関連する化合物 |
| WO2017151158A1 (en) | 2016-03-04 | 2017-09-08 | Halliburton Energy Services, Inc. | Improved performance non-emulsifiers that employ branched alcohols and a new high-solvency carrier oil |
| CA3012434C (en) | 2016-03-04 | 2023-01-03 | Halliburton Energy Services, Inc. | Alkyl unsaturated fatty acid ester oil as an oil component in the formulation and application of surfactant flowback aids for subterranean stimulation |
| EP3464311A4 (en) | 2016-06-06 | 2020-03-18 | Provivi, Inc. | HALF-BIOSYNTHETIC PRODUCTION OF FATTY ALCOHOLS AND FATTY ALDEHYDES |
| US20180049970A1 (en) * | 2016-08-18 | 2018-02-22 | The Procter & Gamble Company | Hair care compositions comprising metathesized unsaturated polyol esters |
| WO2018150379A2 (en) | 2017-02-17 | 2018-08-23 | Provivi, Inc. | Synthesis of pheromones and related materials via olefin metathesis |
| CN110914442B (zh) | 2017-05-17 | 2025-02-18 | 普罗维维股份有限公司 | 用于产生昆虫信息素及相关化合物的微生物 |
| CN109231893A (zh) * | 2018-10-19 | 2019-01-18 | 湖北津泰环保科技有限公司 | 一种抗候性好的沥青玛蹄脂碎石混合料及其制备方法 |
| CN110170077B (zh) * | 2019-03-26 | 2021-09-28 | 南京理工大学 | 一种聚离子型生物润滑剂及其制备方法 |
| AR122497A1 (es) * | 2020-06-01 | 2022-09-14 | Provivi Inc | Síntesis de derivados de feromona a través de metátesis de olefinas z-selectiva |
| EP4259597B1 (en) * | 2020-12-08 | 2024-07-24 | Unilever IP Holdings B.V. | Process to produce oleyl alcohol |
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| US2865968A (en) | 1955-05-06 | 1958-12-23 | Nat Distillers Chem Corp | Production of fatty alcohols |
| DE965236C (de) | 1955-08-22 | 1957-06-06 | Dehydag Gmbh | Verfahren zur kontinuierlichen Herstellung einfach ungesaettigter, hoehermolekularerFettalkohole |
| US4545941A (en) * | 1983-06-20 | 1985-10-08 | A. E. Staley Manufacturing Company | Co-metathesis of triglycerides and ethylene |
| US4804790A (en) | 1983-07-14 | 1989-02-14 | Henkel Kommanditgesellschaft Auf Aktien | Process for obtaining fatty alcohols from free fatty acids |
| DE3724254A1 (de) | 1987-07-22 | 1989-02-02 | Henkel Kgaa | Verfahren zur hydrierung von fettsaeuremethylestern im druckbereich von 20 bis 100 bar |
| DE4142515A1 (de) * | 1991-12-21 | 1993-06-24 | Basf Ag | Verfahren zur herstellung von alkenolen |
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| US8501973B2 (en) | 2006-10-13 | 2013-08-06 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| CN101802097B (zh) * | 2007-08-02 | 2012-11-14 | 科莱恩金融(Bvi)有限公司 | 含有通过二醇单元桥接的磷原子的磷酸酯 |
| MX2012004257A (es) | 2009-10-12 | 2012-05-22 | Elevance Renewable Sciences | Metodos de refinacion y produccion de combustible a partir de materiales de alimentacion de aceite natural. |
-
2013
- 2013-04-22 EP EP13720672.8A patent/EP2841407A1/en not_active Withdrawn
- 2013-04-22 CA CA2871428A patent/CA2871428A1/en not_active Abandoned
- 2013-04-22 IN IN8906DEN2014 patent/IN2014DN08906A/en unknown
- 2013-04-22 US US13/867,542 patent/US20130281688A1/en not_active Abandoned
- 2013-04-22 CN CN201380021877.2A patent/CN104271542A/zh active Pending
- 2013-04-22 WO PCT/US2013/037568 patent/WO2013163071A1/en not_active Ceased
-
2015
- 2015-06-12 US US14/738,493 patent/US20150274619A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013163071A1 (en) | 2013-10-31 |
| IN2014DN08906A (enExample) | 2015-05-22 |
| EP2841407A1 (en) | 2015-03-04 |
| CN104271542A (zh) | 2015-01-07 |
| US20150274619A1 (en) | 2015-10-01 |
| US20130281688A1 (en) | 2013-10-24 |
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