CN106008156A - 一种癸醇的制备方法 - Google Patents
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- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims description 12
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 12
- 239000002808 molecular sieve Substances 0.000 claims description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 12
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 7
- 239000005751 Copper oxide Substances 0.000 claims description 7
- 229910000431 copper oxide Inorganic materials 0.000 claims description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004411 aluminium Substances 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910021417 amorphous silicon Inorganic materials 0.000 claims description 6
- 229910000428 cobalt oxide Inorganic materials 0.000 claims description 6
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 6
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 6
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 6
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 6
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 6
- 238000005245 sintering Methods 0.000 claims description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 6
- 241000269350 Anura Species 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000004898 kneading Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 150000001299 aldehydes Chemical class 0.000 abstract description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- MMFCJPPRCYDLLZ-CMDGGOBGSA-N (2E)-dec-2-enal Chemical compound CCCCCCC\C=C\C=O MMFCJPPRCYDLLZ-CMDGGOBGSA-N 0.000 description 3
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 3
- MMFCJPPRCYDLLZ-UHFFFAOYSA-N dec-2-enal Natural products CCCCCCCC=CC=O MMFCJPPRCYDLLZ-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- 244000020998 Acacia farnesiana Species 0.000 description 1
- 235000003074 Acacia farnesiana Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000015164 Iris germanica var. florentina Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 244000023249 iris florentino Species 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/166—Y-type faujasite
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/7815—Zeolite Beta
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/82—Phosphates
- B01J29/84—Aluminophosphates containing other elements, e.g. metals, boron
- B01J29/85—Silicoaluminophosphates [SAPO compounds]
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/20—After treatment, characterised by the effect to be obtained to introduce other elements in the catalyst composition comprising the molecular sieve, but not specially in or on the molecular sieve itself
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种癸醇的制备方法，包括以下步骤：催化剂制备步骤；加氢步骤，取催化剂20g 装入固定床反应器，氢气流量为 200ml/min，反应温度 240℃，压力 5.0MPa，正丁醛液空速0.5h‑1，氢气与醛体积比为 300:1。本发明采用上述技术方案具有以下技术效果：转化率可达99.7%，纯度可达99.9%，选择性高，工艺简单，副产物少，生产成本低，适合工业生产。
Description
技术领域
本发明涉及化工合成技术领域，尤其涉及一种采用正丁醛制备癸醇的制备方法。
背景技术
癸醇又名正癸醇/癸醇/1-癸醇/十碳醇/壬基甲醇，有具有蜡香、甜香、花香、果香香气，与香茅醇鸢尾根油的混合液相似的无色透明液体。用于制人造玫瑰油、橙花型和金合欢型香精等。也用于制润滑油添加剂、增塑剂、胶粘剂等。
专利公开号为 CN101185893A 的发明专利提出一种用于癸烯醛气相加氢制异癸醇的催化剂及其制备方法，催化剂采用共沉淀法制备，含有氧化铜、氧化锌、氧化铝，活性助剂，用于癸烯醛气相加氢制异癸醇，具有较高的癸烯醛转化率和异癸醇选择性。
目前，液相加氢催化剂的活性和选择性存在矛盾，特别是选择性难以维持在正常水平，副产物多，给生产带来问题，而且为了使产品合格，需要耗费大量蒸汽进行杂质分离。
对于癸醛加氢制备癸醇的反应，需要同时具有高活性和高选择性的加氢催化剂。
发明内容
本发明要解决的技术问题是针对以上问题，提供一种转化率可达99.7%，纯度可达99.9%，选择性高，工艺简单，副产物少，无污染，生产成本低的癸醇
的制备方法。
为解决上述技术问题，本发明采用以下技术方案，一种癸醇的制备方法，包括以下步骤：
1）、催化剂制备步骤；
2）、加氢步骤，取上述催化剂20g 装入固定床反应器，通入氢气，氢气流量为 200ml/min，反应温度 240℃，压力 5.0MPa，正丁醛液空速0.5h-1 ，氢气与醛体积比为 300:1；
步骤1中催化剂由以下重量份的物质组成，二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、二氧化硅4份、氧化铝8份，氧化钼7份,氧化钴4份,氧化钨2份,氧化镍2份，氧化镁4份，氧化铜6份，分子筛8份，无定型硅铝7份。
以下是本发明的进一步改进：
步骤1中催化剂的制备方法如下：首先，将二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、无定型硅铝7份、二氧化硅4份、分子筛8份混合均匀、混捏、成型、干燥、焙烧后制成催化剂载体；干燥温度为 200-250°C，干燥时间为 1-2小时，焙烧温度为1000-1200°C，焙烧时间为3-4小时；
然后，将氧化铝8份，氧化钼7份,氧化钴4份,氧化钨2份,氧化镍2份，氧化镁4份，氧化铜6份浸入硝酸溶液，搅拌至溶解，制成溶液A；
最后，用溶液A喷浸上述催化剂载体，直至饱和，取出，浸渍后干燥、焙烧制成催化剂，干燥温度为 150-200°C，干燥时间为 6-8
小时，焙烧温度为 700-900℃，焙烧时间为 12-24小时。
进一步改进
所述的分子筛为 Y 型分子筛、β 沸石、ZSM 系列分子筛、SAPO 系列分子筛、MCM 系列分子筛中的一种或几种。
进一步改进
硝酸溶液的浓度为3mol/l。
本发明采用上述技术方案具有以下技术效果：转化率可达99.7%，纯度可达99.9%，选择性高，工艺简单，副产物少，生产成本低，适合工业生产。
具体实施方式
实施例，一种癸醇的制备方法，包括以下步骤：
1、催化剂制备步骤；
2、加氢步骤，取上述催化剂A 20g 装入固定床反应器，通入氢气，氢气流量为 200ml/min，反应温度 240℃，压力 5.0MPa，正丁醛液空速0.5h-1 ，氢气与醛体积比为 300:1；
步骤1中催化剂由以下重量份的物质组成，二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、二氧化硅4份、氧化铝8份，氧化钼7份,氧化钴4份,氧化钨2份,氧化镍2份，氧化镁4份，氧化铜6份，分子筛8份，无定型硅铝7份。
所述的分子筛为 Y 型分子筛、β 沸石、ZSM 系列分子筛、SAPO 系列分子筛、MCM 系列分子筛中的一种或几种。
上述催化剂的制备方法如下，将二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、无定型硅铝7份、二氧化硅4份、分子筛8份混合均匀、混捏、成型、干燥、焙烧后制成催化剂载体，干燥温度为 200-250°C，干燥时间为 1-2小时，焙烧温度为1000-1200°C，焙烧时间为3-4小时
；
将氧化铝8份，氧化钼7份,氧化钴4份,氧化钨2份,氧化镍2份，氧化镁4份，氧化铜6份浸入浓度为3mol/l的硝酸溶液，搅拌至溶解，制成溶液A。
用溶液A喷浸上述催化剂载体， 直至饱和，取出，浸渍后干燥、焙烧制成催化剂，干燥温度为 150-200°C，干燥时间为 6-8
小时，焙烧温度为 700-900℃，焙烧时间为 12-24小时。
Claims (4)
1.一种癸醇的制备方法，其特征在于：包括以下步骤：
1）、催化剂制备步骤；
2）、加氢步骤，取上述催化剂 20g 装入固定床反应器，通入氢气，氢气流量为 200ml/min，反应温度为 240℃，压力为5.0MPa，正丁醛液空速为0.5h-1 ，氢气与醛体积比为 300:1；
步骤1中，催化剂由以下重量份的物质组成，二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、二氧化硅4份、氧化铝8份，氧化钼7份、氧化钴4份、氧化钨2份、氧化镍2份、氧化镁4份、氧化铜6份，分子筛8份、无定型硅铝7份。
2.根据权利要求1所述的癸醇的制备方法，其特征在于：所述催化剂制备方法如下：
首先，将二氧化锆10份、二氧化锰15份、三氧化二铁8份、硝酸锰6份、硝酸铁7、无定型硅铝7份、二氧化硅4份、分子筛8份混合均匀、混捏、成型、干燥、焙烧后制成催化剂载体；干燥温度为 200-250°C，干燥时间为 1-2小时，焙烧温度为1000-1200°C，焙烧时间为3-4小时；
然后，将氧化铝8份，氧化钼7份,氧化钴4份,氧化钨2份,氧化镍2份，氧化镁4份，氧化铜6份浸入硝酸溶液，搅拌至溶解，制成溶液A；
最后，用溶液A喷浸上述催化剂载体， 直至饱和，取出，浸渍后干燥、焙烧制成催化剂，干燥温度为 150-200°C，干燥时间为 6-8小时，焙烧温度为 700-900℃，焙烧时间为 12-24小时。
3.根据权利要求1所述的癸醇的制备方法，其特征在于：所述的分子筛为 Y 型分子筛、β 沸石、ZSM 系列分子筛、SAPO 系列分子筛、MCM 系列分子筛中的一种或几种。
4.根据权利要求2所述的癸醇的制备方法，其特征在于：硝酸溶液的浓度为3mol/l。
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