TWI739856B - 二羧酸結晶及其製造方法 - Google Patents
二羧酸結晶及其製造方法 Download PDFInfo
- Publication number
- TWI739856B TWI739856B TW106121388A TW106121388A TWI739856B TW I739856 B TWI739856 B TW I739856B TW 106121388 A TW106121388 A TW 106121388A TW 106121388 A TW106121388 A TW 106121388A TW I739856 B TWI739856 B TW I739856B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- dicarboxylic acid
- less
- mass
- manufacturing
- Prior art date
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 211
- 239000013078 crystal Substances 0.000 title claims abstract description 132
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 48
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 47
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 320
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 174
- 239000001530 fumaric acid Substances 0.000 claims description 160
- -1 polyoxyethylene chains Polymers 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 69
- 238000003756 stirring Methods 0.000 claims description 66
- 229920000642 polymer Polymers 0.000 claims description 63
- 238000001816 cooling Methods 0.000 claims description 57
- 239000002736 nonionic surfactant Substances 0.000 claims description 57
- 239000007864 aqueous solution Substances 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 50
- 238000002425 crystallisation Methods 0.000 claims description 46
- 230000008025 crystallization Effects 0.000 claims description 46
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 41
- 238000001556 precipitation Methods 0.000 claims description 41
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 25
- 239000000194 fatty acid Substances 0.000 claims description 25
- 229930195729 fatty acid Natural products 0.000 claims description 25
- 239000001384 succinic acid Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 13
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 12
- 229920006317 cationic polymer Polymers 0.000 claims description 11
- 230000002093 peripheral effect Effects 0.000 claims description 10
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 9
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 9
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 150000005215 alkyl ethers Chemical class 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 4
- 229930182478 glucoside Natural products 0.000 claims description 4
- 229920003174 cellulose-based polymer Polymers 0.000 claims description 3
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 229920003179 starch-based polymer Polymers 0.000 claims description 3
- 239000004628 starch-based polymer Substances 0.000 claims description 3
- JWNWCEAWZGLYTE-UHFFFAOYSA-N 2-(trimethylazaniumyl)butanoate Chemical compound CCC(C([O-])=O)[N+](C)(C)C JWNWCEAWZGLYTE-UHFFFAOYSA-N 0.000 claims description 2
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 claims description 2
- LGPCLLQCHLRRDE-UHFFFAOYSA-N OC(=O)C=C.CNCCOC(=O)C(C)=C Chemical compound OC(=O)C=C.CNCCOC(=O)C(C)=C LGPCLLQCHLRRDE-UHFFFAOYSA-N 0.000 claims description 2
- 229920000831 ionic polymer Polymers 0.000 claims description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 2
- RVPHHDRVNKOUEJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid [4-(2-methylprop-2-enoyloxy)-1-(trimethylazaniumyl)butan-2-yl] hydrogen phosphate Chemical compound CC(=C)C(O)=O.CC(=C)C(=O)OCCC(C[N+](C)(C)C)OP(O)([O-])=O RVPHHDRVNKOUEJ-UHFFFAOYSA-N 0.000 claims 1
- RUIYSHWWARQKKK-UHFFFAOYSA-N C(C(=C)C)(=O)OCCN.C(C(=C)C)(=O)O Chemical compound C(C(=C)C)(=O)OCCN.C(C(=C)C)(=O)O RUIYSHWWARQKKK-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 89
- 235000011087 fumaric acid Nutrition 0.000 description 158
- 239000003921 oil Substances 0.000 description 92
- 235000019198 oils Nutrition 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 27
- 238000001035 drying Methods 0.000 description 25
- 238000005342 ion exchange Methods 0.000 description 24
- 239000000725 suspension Substances 0.000 description 23
- 239000012065 filter cake Substances 0.000 description 20
- 238000002156 mixing Methods 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- 235000011044 succinic acid Nutrition 0.000 description 18
- 239000011976 maleic acid Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
- 238000004090 dissolution Methods 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 9
- 239000000600 sorbitol Substances 0.000 description 9
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 7
- 239000004359 castor oil Substances 0.000 description 7
- 235000019438 castor oil Nutrition 0.000 description 7
- 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 description 7
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 238000003287 bathing Methods 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 239000000944 linseed oil Substances 0.000 description 5
- 235000021388 linseed oil Nutrition 0.000 description 5
- 239000001630 malic acid Substances 0.000 description 5
- 235000011090 malic acid Nutrition 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229940035044 sorbitan monolaurate Drugs 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VFKZECOCJCGZQK-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCO VFKZECOCJCGZQK-UHFFFAOYSA-M 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229920006318 anionic polymer Polymers 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical group 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- STGNLGBPLOVYMA-KDTZGSNLSA-N (z)-but-2-enedioic acid;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C/C(O)=O STGNLGBPLOVYMA-KDTZGSNLSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 101000983850 Homo sapiens Phosphatidate phosphatase LPIN3 Proteins 0.000 description 1
- 102100025728 Phosphatidate phosphatase LPIN3 Human genes 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 239000001744 Sodium fumarate Substances 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920006319 cationized starch Polymers 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 1
- FBELJLCOAHMRJK-UHFFFAOYSA-L disodium;2,2-bis(2-ethylhexyl)-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCC(CC)CC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CC(CC)CCCC FBELJLCOAHMRJK-UHFFFAOYSA-L 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- DLFDEDJIVYYWTB-UHFFFAOYSA-N dodecyl(dimethyl)azanium;bromide Chemical compound Br.CCCCCCCCCCCCN(C)C DLFDEDJIVYYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 229940048848 lauryl glucoside Drugs 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229920003170 water-soluble synthetic polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/362—Polycarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP??2016-176416 | 2016-09-09 | ||
| JP2016176416 | 2016-09-09 | ||
| JP2017118805A JP6944746B2 (ja) | 2016-09-09 | 2017-06-16 | ジカルボン酸結晶及びその製造方法 |
| JP??2017-118805 | 2017-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201811727A TW201811727A (zh) | 2018-04-01 |
| TWI739856B true TWI739856B (zh) | 2021-09-21 |
Family
ID=61693577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW106121388A TWI739856B (zh) | 2016-09-09 | 2017-06-27 | 二羧酸結晶及其製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP6944746B2 (enExample) |
| CN (1) | CN109689609B (enExample) |
| TW (1) | TWI739856B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108474013A (zh) | 2015-12-24 | 2018-08-31 | 花王株式会社 | 富马酸的制造方法 |
| JP7236285B2 (ja) * | 2019-02-13 | 2023-03-09 | 花王株式会社 | テトラアセチルエチレンジアミン結晶の製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034105A (en) * | 1989-07-27 | 1991-07-23 | Michigan Biotechnology Institute | Carboxylic acid purification and crystallization process |
| CN1252048A (zh) * | 1997-02-12 | 2000-05-03 | Basf公司 | 二羧酸结晶 |
| EP2246319A1 (en) * | 2009-04-28 | 2010-11-03 | DSM IP Assets B.V. | Fumaric acid crystallization process |
| JP2012180306A (ja) * | 2011-03-01 | 2012-09-20 | Mitsubishi Chemicals Corp | 脂肪族ジカルボン酸結晶および脂肪族ジカルボン酸の製造方法 |
| WO2016083749A1 (fr) * | 2014-11-26 | 2016-06-02 | Roquette Freres | Procede de recuperation de cristaux d'acide succinique avec mise en œuvre de tensioactifs au cours de la cristallisation et cristaux obtenus |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS415729B1 (enExample) * | 1964-10-24 | 1966-03-29 | ||
| JP4170079B2 (ja) * | 2002-11-26 | 2008-10-22 | 花王株式会社 | 粉末洗浄剤組成物 |
| JP2004238321A (ja) * | 2003-02-05 | 2004-08-26 | Kao Corp | 口腔用組成物 |
| JP4842119B2 (ja) * | 2006-12-28 | 2011-12-21 | 花王株式会社 | 粉末洗剤の製造方法 |
| JP7053220B2 (ja) * | 2017-06-15 | 2022-04-12 | 花王株式会社 | ジカルボン酸結晶の製造方法 |
-
2017
- 2017-06-16 JP JP2017118805A patent/JP6944746B2/ja active Active
- 2017-06-27 TW TW106121388A patent/TWI739856B/zh active
- 2017-06-27 CN CN201780051200.1A patent/CN109689609B/zh active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034105A (en) * | 1989-07-27 | 1991-07-23 | Michigan Biotechnology Institute | Carboxylic acid purification and crystallization process |
| CN1252048A (zh) * | 1997-02-12 | 2000-05-03 | Basf公司 | 二羧酸结晶 |
| EP2246319A1 (en) * | 2009-04-28 | 2010-11-03 | DSM IP Assets B.V. | Fumaric acid crystallization process |
| JP2012180306A (ja) * | 2011-03-01 | 2012-09-20 | Mitsubishi Chemicals Corp | 脂肪族ジカルボン酸結晶および脂肪族ジカルボン酸の製造方法 |
| WO2016083749A1 (fr) * | 2014-11-26 | 2016-06-02 | Roquette Freres | Procede de recuperation de cristaux d'acide succinique avec mise en œuvre de tensioactifs au cours de la cristallisation et cristaux obtenus |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018043972A (ja) | 2018-03-22 |
| CN109689609A (zh) | 2019-04-26 |
| TW201811727A (zh) | 2018-04-01 |
| JP6944746B2 (ja) | 2021-10-06 |
| CN109689609B (zh) | 2021-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5727660B1 (ja) | セルロースナノファイバー水分散体の製造方法 | |
| CN114502626B (zh) | 乙酸纤维素及乙酸纤维素组合物 | |
| CN102099412A (zh) | 无羧甲基纤维素组分的含细菌纤维素配方 | |
| CN102731608A (zh) | 茶皂素丁二酸酯表面活性剂的制备方法及产品 | |
| TWI739856B (zh) | 二羧酸結晶及其製造方法 | |
| TWI242575B (en) | Preparation method of solvent-free water dispersible hydroxypropyl methyl cellulose phthalate nanoparticle | |
| CN109790226B (zh) | 水溶性羟乙基纤维素的制造方法 | |
| CN102907746B (zh) | 利用辛烯基琥珀酸淀粉钠制备橙油饮料乳液的方法 | |
| WO2021123206A1 (en) | Water and thermal treatment of purified 2,5-furandicarboxylic acid | |
| CN102558124A (zh) | 一种食品级脱氢乙酸钠的制备方法 | |
| TWI746724B (zh) | 二羧酸結晶之製造方法 | |
| TWI557139B (zh) | 纖維素醚粉粒體的製造方法 | |
| JP7053220B2 (ja) | ジカルボン酸結晶の製造方法 | |
| CN103461988A (zh) | 一种高含量α-亚麻酸微胶囊及其制造方法 | |
| KR102341902B1 (ko) | 디카르복실산 결정 및 그 제조 방법 | |
| CN106831678B (zh) | 一种灰黄霉素微晶体的制备方法 | |
| CN115043959A (zh) | 一种高收率依诺肝素钠的制备方法 | |
| JP2003277637A (ja) | 水性ゲルおよびその製造方法 | |
| JP3648573B2 (ja) | カルボキシメチルセルロースナトリウム塩の溶解方法 | |
| JP2019156754A (ja) | フマル酸結晶の製造方法 | |
| CN105085940A (zh) | 壳聚糖的快速溶解方法 | |
| CN103980278B (zh) | 右佐匹克隆微晶及其制备方法 | |
| CN109965176B (zh) | 琼胶食用悬浮剂及其制备方法 | |
| CN117264239A (zh) | 低粉尘易分散黄原胶及其制备方法 | |
| WO2022114076A1 (ja) | 気泡含有組成物製造用添加剤 |