CN1323997C - 二丙酮醇的制造方法 - Google Patents
二丙酮醇的制造方法 Download PDFInfo
- Publication number
- CN1323997C CN1323997C CNB2004800128211A CN200480012821A CN1323997C CN 1323997 C CN1323997 C CN 1323997C CN B2004800128211 A CNB2004800128211 A CN B2004800128211A CN 200480012821 A CN200480012821 A CN 200480012821A CN 1323997 C CN1323997 C CN 1323997C
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- Prior art keywords
- basic catalyst
- solid basic
- weight
- equal
- pore volume
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- 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.)
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 62
- 239000011148 porous material Substances 0.000 claims abstract description 61
- 239000007787 solid Substances 0.000 claims abstract description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 10
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 19
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006482 condensation reaction Methods 0.000 claims description 7
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 6
- 206010013786 Dry skin Diseases 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 150000003818 basic metals Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- -1 diacetone alcohols Chemical class 0.000 claims 1
- 230000007774 longterm Effects 0.000 abstract description 5
- 150000004679 hydroxides Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 6
- 229910001863 barium hydroxide Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000011398 Portland cement Substances 0.000 description 2
- 239000002253 acid Substances 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
- 239000010953 base metal Substances 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
-
- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
催化剂构成(重量%) | 细孔容积(ml/g) | 初期活性(%) | 失活速度(%·催化剂kg/丙酮L) | ||||
钡* | 水 | 0.01μm~0.1μm | 0.1μm~1μm | 0.01μm~1μm | |||
实施例1 | 46.7 | 42.3 | 0.84 | 1.21 | 2.05 | 13.9 | 0.00070 |
实施例2 | 46.0 | 42.1 | 0.94 | 1.34 | 2.28 | 15.0 | 0.00088 |
实施例3 | 46.1 | 42.6 | 1.07 | 1.30 | 2.37 | 14.7 | 0.00048 |
实施例4 | 43.0 | 41.6 | 1.01 | 1.21 | 2.22 | 14.5 | 0.00071 |
实施例5 | 44.5 | 41.8 | 0.96 | 1.15 | 2.11 | 14.3 | 0.00069 |
实施例6 | 44.5 | 42.7 | 1.06 | 1.17 | 2.23 | 14.4 | 0.00048 |
实施例7 | 45.5 | 42.1 | 0.83 | 1.22 | 2.05 | 14.9 | 0.00082 |
实施例8 | 45.1 | 42.4 | 0.82 | 1.30 | 2.12 | 14.4 | 0.00070 |
实施例9 | 45.5 | 44.0 | 1.16 | 1.59 | 2.75 | 15.1 | 0.00050 |
实施例10 | 46.6 | 43.4 | 1.10 | 1.77 | 2.87 | 15.7 | 0.00057 |
实施例11 | 46.8 | 43.5 | 1.20 | 1.57 | 2.77 | 15.3 | 0.00039 |
实施例12 | 47.1 | 43.7 | 1.11 | 1.56 | 2.67 | 14.9 | 0.00051 |
实施例13 | 48.7 | 44.7 | 0.99 | 1.21 | 2.20 | 13.8 | 0.00058 |
实施例14 | 48.3 | 44.3 | 1.00 | 1.11 | 2.11 | 14.7 | 0.00063 |
实施例15 | 48.8 | 44.7 | 1.06 | 1.19 | 2.25 | 14.6 | 0.00047 |
实施例16 | 48.5 | 43.6 | 1.00 | 1.09 | 2.09 | 14.5 | 0.00069 |
比较例1 | 45.0 | 41.4 | 0.82 | 0.88 | 1.70 | 14.1 | 0.00106 |
比较例2 | 44.3 | 42.5 | 0.74 | 0.91 | 1.65 | 12.9 | 0.00102 |
比较例3 | 45.1 | 42.3 | 0.71 | 0.86 | 1.57 | 13.8 | 0.00114 |
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003137370 | 2003-05-15 | ||
JP137370/2003 | 2003-05-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1787986A CN1787986A (zh) | 2006-06-14 |
CN1323997C true CN1323997C (zh) | 2007-07-04 |
Family
ID=33447255
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800128211A Expired - Lifetime CN1323997C (zh) | 2003-05-15 | 2004-05-06 | 二丙酮醇的制造方法 |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN1323997C (zh) |
WO (1) | WO2004101485A1 (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102757327B (zh) * | 2011-04-29 | 2014-05-28 | 中国石油化工股份有限公司 | 一种氧化丙酮制备二丙酮醇的方法 |
CN103724172B (zh) * | 2014-01-17 | 2016-01-20 | 天津市道福化工新技术开发有限公司 | 二丙酮醇的合成工艺 |
CN106660917A (zh) | 2014-07-25 | 2017-05-10 | 沙特基础工业全球技术有限公司 | 二丙酮醇和异丙叉丙酮的合成 |
CN104355976B (zh) * | 2014-11-07 | 2016-01-20 | 中国海洋石油总公司 | 一种丙酮一步法合成异丙叉丙酮的方法 |
CN104355975B (zh) * | 2014-11-07 | 2016-01-20 | 中国海洋石油总公司 | 一种丙酮两步法合成甲基异丁基酮的方法 |
CN105037123B (zh) * | 2015-07-28 | 2017-06-23 | 江苏苏源辉普化工有限公司 | 一种连续法生产二丙酮醇的方法 |
CN108383704B (zh) * | 2018-05-01 | 2021-03-23 | 利安隆凯亚(河北)新材料有限公司 | 一种利用合成三丙酮胺过程副产物制备丙酮的方法 |
CN109824498B (zh) * | 2018-12-22 | 2021-12-14 | 谦信化工集团有限公司 | 一种二丙酮醇连续化生产装置及生产工艺 |
CN110183432B (zh) * | 2019-06-28 | 2021-08-31 | 珠海市柏瑞医药科技有限公司 | 一种5,6-o-异亚丙基-l-抗坏血酸的制备工艺 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61259756A (ja) * | 1985-05-14 | 1986-11-18 | Mitsubishi Chem Ind Ltd | アセトン縮合触媒の製造方法 |
JPH11228464A (ja) * | 1998-02-20 | 1999-08-24 | Mitsui Chem Inc | メチルイソブチルケトンおよび/またはメチルイソブチルカルビノールの製造方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63123440A (ja) * | 1986-11-13 | 1988-05-27 | Mitsubishi Kasei Corp | アセトン縮合触媒の製造方法 |
-
2004
- 2004-05-06 CN CNB2004800128211A patent/CN1323997C/zh not_active Expired - Lifetime
- 2004-05-06 WO PCT/JP2004/006408 patent/WO2004101485A1/ja active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61259756A (ja) * | 1985-05-14 | 1986-11-18 | Mitsubishi Chem Ind Ltd | アセトン縮合触媒の製造方法 |
JPH11228464A (ja) * | 1998-02-20 | 1999-08-24 | Mitsui Chem Inc | メチルイソブチルケトンおよび/またはメチルイソブチルカルビノールの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2004101485A1 (ja) | 2004-11-25 |
CN1787986A (zh) | 2006-06-14 |
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Effective date of registration: 20170927 Address after: Tokyo, Japan Patentee after: MITSUBISHI RAYON Co.,Ltd. Address before: Tokyo, Japan, the Port District Zhi four Ding Ding, No. 14, No. 1 Patentee before: MITSUBISHI CHEMICAL Corp. |
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CX01 | Expiry of patent term |
Granted publication date: 20070704 |