JP2017534660A - 反応混合物からギ酸塩を得るためのプロセス - Google Patents
反応混合物からギ酸塩を得るためのプロセス Download PDFInfo
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- JP2017534660A JP2017534660A JP2017526689A JP2017526689A JP2017534660A JP 2017534660 A JP2017534660 A JP 2017534660A JP 2017526689 A JP2017526689 A JP 2017526689A JP 2017526689 A JP2017526689 A JP 2017526689A JP 2017534660 A JP2017534660 A JP 2017534660A
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- hydroxide
- formic acid
- water
- reaction mixture
- vapor
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- 239000011541 reaction mixture Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 42
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 title claims abstract description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 122
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 61
- 235000019253 formic acid Nutrition 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims abstract description 12
- 150000002500 ions Chemical class 0.000 claims abstract description 10
- 238000001223 reverse osmosis Methods 0.000 claims abstract description 5
- 239000011368 organic material Substances 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 150000001720 carbohydrates Chemical class 0.000 claims description 8
- 229930182470 glycoside Natural products 0.000 claims description 8
- 150000002338 glycosides Chemical class 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000013589 supplement Substances 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 2
- 239000005750 Copper hydroxide Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 12
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 8
- 235000014633 carbohydrates Nutrition 0.000 description 7
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 229940040102 levulinic acid Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 229920002488 Hemicellulose Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 150000007522 mineralic acids Chemical group 0.000 description 2
- 239000010893 paper waste Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000192700 Cyanobacteria Species 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000002577 cryoprotective agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/02—Formic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F5/00—Compounds of magnesium
- C01F5/14—Magnesium hydroxide
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G39/00—Compounds of molybdenum
- C01G39/006—Compounds containing, besides molybdenum, two or more other elements, with the exception of oxygen or hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/02—Formic acid
- C07C53/06—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/048—Purification of waste water by evaporation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
- C02F1/441—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by reverse osmosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
a)逆浸透によって、および/または、引き続き凝縮される蒸気として、反応混合物からギ酸および水の混合物を分離すること、
b)水溶液中で、ギ酸を水酸化物と反応させてギ酸塩の溶液を形成すること
を含む。
10 反応混合物
12 さらなる有機材料
13 第一の蒸留容器
14 水/水蒸気
16 熱交換器
18 ギ酸蒸気−水蒸気混合物
19 残渣
22 ギ酸−水混合物
23 第二の容器
24 水酸化物
26 ギ酸塩−水混合物
27 第二の蒸留容器
28 濃縮ギ酸溶液
30 タンクトラック
Claims (11)
- 反応混合物(10)からギ酸塩を得るための方法であって、触媒として作用する一般式[PMoxVyO40]n−で表されるポリ酸イオンを、120℃未満の温度で有機材料と接触させ、水溶液中でギ酸を産生し、式中、6≦x≦11、1≦y≦6、x+y=12および3<n<10であり、式中、n、xおよびyは各々整数であり、以下の工程:
a)逆浸透によっておよび/または引き続き凝縮される蒸気(18)として、反応混合物からギ酸および水の混合物を分離すること、および
b)水溶液中で、ギ酸を水酸化物(24)と反応させて、ギ酸塩の溶液を産生すること
を含む、前記方法。 - 工程b)で産生される溶液を、逆浸透によっておよび/または水(14)の部分的もしくは完全な蒸発によって、工程c)において濃縮する、請求項1に記載の方法。
- 有機材料がアルファ−ヒドロキシアルデヒド、アルファ−ヒドロキシカルボン酸、炭水化物またはグリコシドである、請求項1または2に記載の方法。
- さらなる水および/または工程c)において分離される水(14)を、反応混合物(10)に添加し、工程a)において分離された水を補う、請求項1〜3のいずれか一項に記載の方法。
- さらなる有機材料(12)を、反応した有機材料を補うために反応混合物(10)に添加する、請求項1〜4のいずれか一項に記載の方法。
- 接触の維持および/または工程a)による蒸気(18)としての分離が、15〜119.5℃、特に40〜95℃、特に50〜85℃、特に55〜85℃、特に60〜83℃で発生する、請求項1〜5のいずれか一項に記載の方法。
- 工程a)による蒸気(18)としての分離が、大気圧よりも低い気圧で生じる、請求項1〜6のいずれか一項に記載の方法。
- 工程a)による蒸気(18)の凝縮が、蒸気(18)を水、水溶液または工程b)に記載の水溶液に導入することによって生じる、請求項1〜7のいずれか一項に記載の方法。
- 水酸化物(24)が、水酸化アンモニウム、水酸化アルミニウム、水酸化銅、水酸化ニッケル、アルカリ土類金属水酸化物、アルカリ金属水酸化物、水酸化カルシウム、水酸化マグネシウム、水酸化ナトリウム、水酸化カリウム、または水酸化セシウムである、請求項1〜8のいずれか一項に記載の方法。
- 工程b)における水酸化物(24)を、ギ酸に対して、完全にまたはほぼ完全に反応する化学量論比で使用する、請求項1〜9のいずれか一項に記載の方法。
- n=3+yである、請求項1〜10のいずれか一項に記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2014/074930 WO2016078698A1 (de) | 2014-11-18 | 2014-11-18 | Verfahren zum gewinnen eines formiats aus einem reaktionsgemisch |
Publications (3)
Publication Number | Publication Date |
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JP2017534660A true JP2017534660A (ja) | 2017-11-24 |
JP2017534660A5 JP2017534660A5 (ja) | 2018-01-11 |
JP6534444B2 JP6534444B2 (ja) | 2019-06-26 |
Family
ID=51945864
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2017526689A Active JP6534444B2 (ja) | 2014-11-18 | 2014-11-18 | 反応混合物からギ酸塩を得るためのプロセス |
Country Status (7)
Country | Link |
---|---|
US (1) | US10179757B2 (ja) |
EP (1) | EP3221288B1 (ja) |
JP (1) | JP6534444B2 (ja) |
KR (1) | KR102308791B1 (ja) |
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DK3048092T3 (da) | 2015-01-26 | 2017-07-31 | Jbach Gmbh | Fremgangsmåde til katalytisk fremstilling af myresyre ved et oxygenpartialtryk under 1 Bar og regenerering af katalysatoren anvendt deri |
DE102016213099A1 (de) | 2016-07-18 | 2018-01-18 | Oxfa Gmbh | Verfahren zur katalytischen Erzeugung von Ameisensäure und Regeneration des dabei eingesetzten Katalysators bei geringem Überdruck |
DE102016213100A1 (de) * | 2016-07-18 | 2018-01-18 | Oxfa Gmbh | Verfahren zum Absondern von Ameisensäure aus einem Reaktionsgemisch durch Extraktion |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5712882A (en) * | 1980-06-26 | 1982-01-22 | Mitsubishi Heavy Ind Ltd | Recovery of water by-produced in synthesis of aromatic hydrocarbon mixture |
JPH11504935A (ja) * | 1995-05-12 | 1999-05-11 | ノルスク・ヒドロ・アーエスアー | ギ酸の複塩を含有する製品の製造方法 |
JP2004002280A (ja) * | 2001-11-09 | 2004-01-08 | Basf Ag | 金属ギ酸塩/ギ酸混合物の製造方法 |
WO2009130387A2 (en) * | 2008-04-21 | 2009-10-29 | Kemira Oyj | A process for preparation of formate salt |
JP2013540735A (ja) * | 2010-09-17 | 2013-11-07 | ヨットバッハ ゲーエムベーハー | ギ酸を触媒的に製造する方法 |
Family Cites Families (3)
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---|---|---|---|---|
US3357899A (en) * | 1963-08-30 | 1967-12-12 | Celanese Corp | Method of recovering formic acid from a waste liquor |
US4177075A (en) * | 1978-06-05 | 1979-12-04 | M&T Chemicals Inc. | Jet printing ink containing ammonium formate electrolyte |
AT367473B (de) | 1980-04-10 | 1982-07-12 | Kanzler Walter | Verfahren zur gewinnung von furfurol, ameisensaeure, essigsaeure aus sauren hydrolysaten von pflanzen |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5712882A (en) * | 1980-06-26 | 1982-01-22 | Mitsubishi Heavy Ind Ltd | Recovery of water by-produced in synthesis of aromatic hydrocarbon mixture |
JPH11504935A (ja) * | 1995-05-12 | 1999-05-11 | ノルスク・ヒドロ・アーエスアー | ギ酸の複塩を含有する製品の製造方法 |
JP2004002280A (ja) * | 2001-11-09 | 2004-01-08 | Basf Ag | 金属ギ酸塩/ギ酸混合物の製造方法 |
WO2009130387A2 (en) * | 2008-04-21 | 2009-10-29 | Kemira Oyj | A process for preparation of formate salt |
JP2013540735A (ja) * | 2010-09-17 | 2013-11-07 | ヨットバッハ ゲーエムベーハー | ギ酸を触媒的に製造する方法 |
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DK3221288T3 (en) | 2019-04-08 |
EP3221288B1 (de) | 2018-12-26 |
JP6534444B2 (ja) | 2019-06-26 |
EP3221288A1 (de) | 2017-09-27 |
WO2016078698A9 (de) | 2017-10-19 |
CN107108435A (zh) | 2017-08-29 |
US10179757B2 (en) | 2019-01-15 |
KR20170084277A (ko) | 2017-07-19 |
WO2016078698A1 (de) | 2016-05-26 |
KR102308791B1 (ko) | 2021-10-05 |
US20170327451A1 (en) | 2017-11-16 |
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