JP2020502139A - トリメチロールプロパンの製造方法 - Google Patents
トリメチロールプロパンの製造方法 Download PDFInfo
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- JP2020502139A JP2020502139A JP2019531888A JP2019531888A JP2020502139A JP 2020502139 A JP2020502139 A JP 2020502139A JP 2019531888 A JP2019531888 A JP 2019531888A JP 2019531888 A JP2019531888 A JP 2019531888A JP 2020502139 A JP2020502139 A JP 2020502139A
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- trimethylolpropane
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- YYKMQUOJKCKTSD-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanal Chemical compound CCC(CO)(CO)C=O YYKMQUOJKCKTSD-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexanol group Chemical group C(C)C(CO)CCCC YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 47
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005882 aldol condensation reaction Methods 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000000605 extraction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000005705 Cannizzaro reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XIKVGYYSAJEFFR-UHFFFAOYSA-N 2-(hydroxymethyl)butanal Chemical compound CCC(CO)C=O XIKVGYYSAJEFFR-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
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- B01J8/0285—Heating or cooling the reactor
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- 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
- C07C29/14—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 a —CHO group
- C07C29/141—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 a —CHO group with hydrogen or hydrogen-containing gases
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- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
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- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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Abstract
Description
ジメチロールブタナール(DMB)を金属触媒及びアルコール溶媒下で水素化反応させてトリメチロールプロパン(TMP)を製造するステップを含み、
上記水素化反応の時、ジメチロールブタナールを基準にアルコール溶媒の重量比が2ないし10であるトリメチロールプロパンの製造方法を提供する。
収率(%)=ΔTMP/反応物DMB×100
DMB転換率(%)=100×(1−生成物DMB/反応物DMB)
選択度(%)=ΔTMP/ΔDMB×100=収率×100/転換率
図1によれば、ジメチロールブタナールは配管11を通じて、アルコール溶媒は配管12を通じてそれぞれ反応原料1に投入される。このとき、アルコール溶媒は、炭素数2ないし10のアルコール溶媒であってもよく、好ましくは炭素数8のアルコール溶媒であってもよく、より好ましくは2−エチルヘキサノールであってもよい。上記ジメチロールブタナールは、アルドール縮合反応の後、一連の分離過程を経て得ることができる。上記一連の分離過程は、抽出であってもよい。
図2によれば、貯蔵槽7には、未反応のDMBを含む生成物の一部が少量流入することができる。この場合、未反応のDMBの転換及び水素化反応の反応熱を制御するために、貯蔵槽7にある未反応のDMBを含む生成物の一部が配管19を通じて反応器4に流入して、再循環されることができる。
<製造例1>
10Lのジャケット型(jacket type)反応器において、FA/n−BAL=4のモル比で反応したアルドール縮合反応生成物から、抽出を通じてジメチロールブタナール(DMB)を製造した。
製造例1で得たDMBに2−エチルヘキサノール(2−EH)を添加して水素化原料を調製した。
その後、銅系金属触媒が充填されているL/D(反応区域の高さ(L)を直径(D)で割った値)が30であるFBR(Fixed Bed Reactor)に調製された原料を投入して、水素化反応によってTMPを製造した。
このとき、DMBを基準に2−EHの重量比(2−EH/DMB)は4だった。水素化反応時に添加される水素のモル数は、H2/DMB(mol/mol)=1.5とし、 WHSV(Weight Hourly Space Velocity)=0.3h-1に設定した。反応器の入口と出口にはアルミナボールが中間の触媒層を支持しており、12個の温度センサーが一定の間隔で差し込まれて温度プロファイル(profile)を示した。触媒層の入口温度を反応温度として120℃で実験し、反応圧力は30barに設定した。
実施例1において、DMBを基準に2−EHの重量比(2−EH/DMB)は6であることを除き、実施例1と同一の方法でTMPを製造した。
実施例1において、DMBを基準に2−EHの重量比(2−EH/DMB)は10であることを除き、実施例1と同一の方法でTMPを製造した。
実施例1において、DMBを基準に2−EHの重量比(2−EH/DMB)は12であることを除き、実施例1と同一の方法でTMPを製造した。
実施例1において、2−エチルヘキサノールの代わりに1−ヘキサノール(1−hexanol)を使用し、DMBを基準に1−ヘキサノールの重量比(1−ヘキサノール/DMB)は4であることを除き、実施例1と同一の方法でTMPを製造した。
DMB転換率(%)=100×(1−生成物DMB/反応物DMB)
TMP選択度(%)=ΔTMP/ΔDMB×100=収率×100/転換率
実施例1において、DMBを基準に2−EHの重量比(2−EH/DMB)は1であることを除き、実施例1と同一の方法でTMPを製造した。
[式(1)]
Q=ΣCpi*mi*△Ti
(Q:反応熱、i:各組成成分、Cp:各組成成分の熱容量値、m:水素化反応の生成物各組成の質量(mass)値)
[式(2)]
r=A*e-Ea/RT
(r:反応速度、T:絶対温度、R:気体定数、A:頻度係数または頻度因子、Ea:活性化エネルギで、ここではQ値と同一)
2:水素貯蔵タンク
3:加熱器
4:反応器
5:熱交換器
6:ポンプ
7:貯蔵槽
11、12、13、14、15、16、17、18、19:配管
Claims (9)
- ジメチロールブタナール(DMB)を金属触媒及びアルコール溶媒下で水素化反応させてトリメチロールプロパン(TMP)を製造するステップを含み、
前記水素化反応の時、ジメチロールブタナールを基準にアルコール溶媒の重量比が2ないし10であるトリメチロールプロパンの製造方法。 - 前記アルコール溶媒は、炭素数2ないし10のアルコール溶媒である、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記金属触媒は、銅系金属触媒である、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記水素化反応の反応温度は、80℃ないし160℃である、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記水素化反応の反応圧力は、20barないし70barである、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記アルコール溶媒は、2−エチルヘキサノール(2−ethyl hexanol)である、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記水素化反応の時、ジメチロールブタナールを基準に水素(H2)のモル比が1ないし3である、請求項1に記載のトリメチロールプロパンの製造方法。
- 前記トリメチロールプロパンを製造するステップは、トリメチロールプロパンを98%以上の収率で製造するものである、請求項1に記載のトリメチロールプロパンの製造方法。
- (A)n−ブチルアルデヒド(n−BAL)とホルムアルデヒド(FA)とをアルキルアミン触媒下にアルドール縮合反応させて、ジメチロールブタナール(DMB)混合生成物を製造するステップ;及び
(B)前記ジメチロールブタナール混合生成物からジメチロールブタナールを分離するステップをさらに含む、請求項1ないし8のいずれか一項に記載のトリメチロールプロパンの製造方法。
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KR10-2017-0137495 | 2017-10-23 | ||
KR1020170137495A KR102245932B1 (ko) | 2017-10-23 | 2017-10-23 | 트리메틸올프로판의 제조방법 |
PCT/KR2018/011742 WO2019083188A1 (ko) | 2017-10-23 | 2018-10-04 | 트리메틸올프로판의 제조방법 |
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CN111715238B (zh) * | 2020-07-01 | 2022-08-05 | 万华化学集团股份有限公司 | 一种加氢催化剂及其制备方法和应用 |
CN111848354B (zh) * | 2020-08-03 | 2022-08-05 | 万华化学集团股份有限公司 | 一种三羟甲基丙烷的制备方法 |
CN112517018B (zh) * | 2020-11-30 | 2022-08-05 | 万华化学集团股份有限公司 | 一种2,2-二羟甲基丁醛加氢制备三羟甲基丙烷的催化剂及其制备方法和应用 |
CN114409520B (zh) * | 2022-02-11 | 2023-05-30 | 万华化学集团股份有限公司 | 一种高缩合收率加氢制备三羟甲基丙烷的方法 |
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BE790366A (fr) | 1971-10-21 | 1973-04-20 | Ciba Geigy | Phosphonothionates de triazolyles et produits pesticides qui encontiennent |
DE19542036A1 (de) | 1995-11-10 | 1997-05-15 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
DE19653093A1 (de) | 1996-12-20 | 1998-06-25 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
DE10055180A1 (de) * | 2000-11-08 | 2002-05-29 | Basf Ag | Verfahren zur Hydrierung von Poly- oder Monomethylolalkanalen |
DE10119719A1 (de) * | 2001-04-21 | 2002-10-24 | Basf Ag | Verfahren zur Hydrierung von Carbonylverbindungen |
DE10164264A1 (de) | 2001-12-27 | 2003-07-17 | Bayer Ag | Verfahren zur Herstellung von Trimethylolpropan |
DE102006009838A1 (de) * | 2006-03-01 | 2007-09-06 | Basf Ag | Verfahren zur Hydrierung von Methylolalkanalen |
KR100837523B1 (ko) * | 2006-03-07 | 2008-06-12 | 주식회사 엘지화학 | 트리메틸올프로판의 제조방법 |
US7388116B2 (en) | 2006-06-06 | 2008-06-17 | Basf Aktiengesellschaft | Hydrogenation of methylolalkanals |
US7462747B2 (en) * | 2007-01-05 | 2008-12-09 | Basf Aktiengesellschaft | Process for preparing polyalcohols from formaldehyde having a low formic acid content |
KR101773327B1 (ko) | 2008-12-09 | 2017-08-31 | 바스프 에스이 | 폴리메틸올의 정제 방법 |
TWI490034B (zh) * | 2009-11-17 | 2015-07-01 | Basf Se | 製備具有增強氫化活性之經承載氫化觸媒之方法 |
CN104892364B (zh) * | 2015-06-02 | 2016-06-01 | 万华化学集团股份有限公司 | 一种采用加氢法制备三羟甲基丙烷的方法 |
KR101833055B1 (ko) | 2016-06-03 | 2018-02-27 | 김진욱 | 3차원 측정 장치 |
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EP3539941B1 (en) | 2021-06-23 |
WO2019083188A1 (ko) | 2019-05-02 |
CN110121486A (zh) | 2019-08-13 |
KR20190044907A (ko) | 2019-05-02 |
CN110121486B (zh) | 2022-07-12 |
KR102245932B1 (ko) | 2021-04-28 |
US10947174B2 (en) | 2021-03-16 |
US20200189998A1 (en) | 2020-06-18 |
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JP6817445B2 (ja) | 2021-01-20 |
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