CN110655475A - 一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 - Google Patents
一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 Download PDFInfo
- Publication number
- CN110655475A CN110655475A CN201911023252.5A CN201911023252A CN110655475A CN 110655475 A CN110655475 A CN 110655475A CN 201911023252 A CN201911023252 A CN 201911023252A CN 110655475 A CN110655475 A CN 110655475A
- Authority
- CN
- China
- Prior art keywords
- ethylene bis
- composite doped
- salt
- acid
- stearic acid
- Prior art date
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 34
- 239000011964 heteropoly acid Substances 0.000 title claims abstract description 31
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000002131 composite material Substances 0.000 title claims abstract description 24
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000006555 catalytic reaction Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 17
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 17
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008117 stearic acid Substances 0.000 claims abstract description 17
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 10
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of chromium, molybdenum or tungsten
-
- 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
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
-
- 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
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
技术领域
本发明涉及一种合成乙撑双硬脂酰胺的方法,特别涉及复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法。
背景技术
乙撑双硬脂酰胺(简称为EBS),是一种重要的塑料助剂,具有润滑、脱模、抗静电和增加塑料制品的表面光泽等功能,广泛应用于ABS、PVC和PC等热塑性树脂的加工。在文献报道的EBS合成方法中,以硬脂酸与乙二胺为原料,经中和成盐、催化脱水两步反应制备EBS的成本相对较低,是目前工业化生产的主要方法。
目前,工业生产EBS主要采用硫酸或磷酸等为催化剂(胡丹等,精细化工中间体,2013,43(1): 59-62),具有较高的催化活性,但因反应温度较高,催化剂本身具有氧化能力,容易造成产品发黄,色泽偏高。即使添加抗氧化剂,并在反应系统中通入氮气,产品的白度仍有待提高。此外,硫酸等易腐蚀反应设备,反应完成后残留在产品中,对产品的质量与应用具有影响。
因此,开发具有高效催化性能,不易腐蚀设备,且不会促进产品氧化的催化剂,以实现高纯度、高白度EBS的高效合成,仍然是本领域的技术人员迫切需要解决的技术问题。
发明内容
本发明的目的在于提供一种催化合成乙撑双硬脂酰胺的方法。
本发明提供了一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法,其特征在
于,以复合掺杂杂多酸盐为催化剂,催化硬脂酸和乙二胺合成乙撑双硬脂酰胺,所述复合掺
杂杂多酸盐的结构式为:,其中,R= -C16H33,x=0.4~0.6,y=
0.4~0.6。
进一步地,所述复合掺杂杂多酸盐的制备方法:将硝酸锆、十六烷基三甲基氯化铵与磷钨酸混合于水中,反应后分离得到的沉淀物即为所述复合掺杂杂多酸盐。
进一步地,所述合成乙撑双硬脂酰胺的步骤包括:
(1)加入硬脂酸和抗氧化剂,通入氮气,升温至90~110℃,其中,硬脂酸与抗氧化剂的质量比为100:0.3~0.5;
(2)在步骤(1)的反应体系中加入乙二胺,反应1~2 h,其中,硬脂酸与乙二胺的摩尔比为2:1.12~1.16;
(3)在步骤(2)的反应体系中加入复合掺杂杂多酸盐作为催化剂,升温至190~210℃,反应3~5 h,其中,复合掺杂杂多酸盐与硬脂酸的质量比为0.5~1:100。
进一步地,所述抗氧化剂为亚硫酸氢钠或硼氢化钠。
本发明所涉及的复合掺杂杂多酸盐催化剂分子结构中含有亲油性基团,对原料硬脂酸的亲和性好,且具有较高的比表面积,适宜的酸强度和较高的表面酸量,对合成乙撑双硬脂酰胺的反应具有优异的催化性能,产物的收率高,色泽浅,纯度高。此外,复合掺杂杂多酸盐不会腐蚀反应设备,反应完成后无需分离,不会影响产品乙撑双硬脂酰胺的使用。
具体实施方式
下面对本发明的具体实施方式作进一步的详细说明。对于所属技术领域的技术人员而言,从对本发明的详细说明中,本发明的上述和其他目的、特征和优点将显而易见。
实施例1:
催化剂的制备:称取0.5 mmol十六烷基三甲基氯化铵、 0.5 mmol硝酸锆和1 mmol磷钨酸分别溶解在20 ml去离子水中;完全溶解后,在室温和持续搅拌的条件下,先将十六烷基三甲基氯化铵溶液缓慢滴加至磷钨酸溶液中,再继续缓慢滴加硝酸锆溶液,逐渐生成白色沉淀;滴加完之后,继续搅拌0.5 h,再静置陈化1 h。白色沉淀经过滤分离后,干燥,即可得到分子式为[(C16H33)N(CH3)3]0.5Zr0.5 H0.5PW12O40的复合掺杂杂多酸盐。
实施例2:
催化剂的制备:制备过程同实施例1,仅将十六烷基三甲基氯化铵的加入量改为0.4mmol,硝酸锆的加入量改为0.6 mmol,可得到分子式为[(C16H33)N(CH3)3]0.4Zr0.6H0.2PW12O40的复合掺杂杂多酸盐。
实施例3:
催化剂的制备:制备过程同实施例1,仅将十六烷基三甲基氯化铵的加入量改为0.6mmol,硝酸锆的加入量改为0.4 mmol,可得到分子式为[(C16H33)N(CH3)3]0.6Zr0.4H0.8PW12O40的复合掺杂杂多酸盐。
实施例4:
在反应器中加入100 g硬脂酸和0.4 g抗氧化剂,通入氮气,升温至100℃,加入12.7g乙二胺,中和成盐反应1.5 h后,加入0.7 g实施例1中制备的复合掺杂杂多酸盐催化剂,升温至200℃,脱水反应4 h,得到白色的乙撑双硬脂酰胺产品,产品的酸值:2.6 mg/g,熔程:144~150℃,白度值:90。
实施例5:
采用与实施例4相同的反应条件,仅将催化剂改为实施例2中制备的复合掺杂杂多酸盐,乙撑双硬脂酰胺产品的酸值:3.1 mg/g,熔程:144~149℃,白度值:89。
实施例6:
采用与实施例4相同的反应条件,仅将催化剂改为实施例3中制备的复合掺杂杂多酸盐,乙撑双硬脂酰胺产品的酸值:3.5 mg/g,熔程:143~147℃,白度值:90。
实施例7:
在反应器中加入100 g硬脂酸和0.5 g抗氧化剂,通入氮气,升温至90℃,加入12.4g乙二胺,中和成盐反应2 h后,加入0.5 g实施例1中制备的复合掺杂杂多酸盐催化剂,升温至210℃,脱水反应3 h,得到白色的乙撑双硬脂酰胺产品,产品的酸值:5.1 mg/g,熔程:144~150℃,白度值:88。
实施例8:
在反应器中加入100 g硬脂酸和0.3 g抗氧化剂,通入氮气,升温至110℃,加入12.8g乙二胺,中和成盐反应1 h后,加入1 g实施例1中制备的复合掺杂杂多酸盐催化剂,升温至190℃,脱水反应5 h,得到白色的乙撑双硬脂酰胺产品,产品的酸值:3.7 mg/g,熔程:143~147℃,白度值:90。
根据实施例4-8的结果,本发明涉及的复合掺杂杂多酸盐催化剂对合成乙撑双硬脂酰胺的反应具有优异的催化性能,产物的酸值低,表明其收率高;熔程短,表明纯度高;白度值高,色泽浅。与目前工业上使用的硫酸、磷酸等传统催化剂相比,复合掺杂杂多酸盐对反应设备无腐蚀,不会造成产品的氧化,反应完成后无需分离,不会影响产品乙撑双硬脂酰胺的使用。
应当理解,本发明虽然已通过以上实施例进行了清楚说明,然而在不背离本发明精神及其实质的情况下,所属技术领域的技术人员当可根据本发明作出各种相应的变化和修正,但这些相应的变化和修正都应属于本发明的权利要求的保护范围。
Claims (3)
1.一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法,其特征在于,以复合掺杂
杂多酸盐为催化剂,催化硬脂酸和乙二胺合成乙撑双硬脂酰胺,所述复合掺杂杂多酸盐的
结构式为:,其中,R= -C16H33,x=0.4~0.6,y=0.4~0.6。
2.根据权利要求1所述的合成乙撑双硬脂酰胺的方法,其特征在于,所述合成乙撑双硬脂酰胺的步骤包括:
(1)加入硬脂酸和抗氧化剂,通入氮气,升温至90~110℃,其中,硬脂酸与抗氧化剂的质量比为100:0.3~0.5;
(2)在步骤(1)的反应体系中加入乙二胺,反应1~2 h,其中,硬脂酸与乙二胺的摩尔比为2:1.12~1.16;
(3)在步骤(2)的反应体系中加入复合掺杂杂多酸盐作为催化剂,升温至190~210℃,反应3~5 h,其中,复合掺杂杂多酸盐与硬脂酸的质量比为0.5~1:100。
3.根据权利要求1和2所述的合成乙撑双硬脂酰胺的方法,所述抗氧化剂为亚硫酸氢钠或硼氢化钠。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911023252.5A CN110655475B (zh) | 2019-10-25 | 2019-10-25 | 一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911023252.5A CN110655475B (zh) | 2019-10-25 | 2019-10-25 | 一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110655475A true CN110655475A (zh) | 2020-01-07 |
CN110655475B CN110655475B (zh) | 2022-08-09 |
Family
ID=69041758
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201911023252.5A Active CN110655475B (zh) | 2019-10-25 | 2019-10-25 | 一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110655475B (zh) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101574667A (zh) * | 2009-06-08 | 2009-11-11 | 南京工业大学 | 一种固体酸催化剂及其制备和在酯化反应中的应用 |
CN101665447A (zh) * | 2009-09-22 | 2010-03-10 | 如皋市双马化工有限公司 | 一种硬脂酸合成乙撑硬脂酸酰胺的方法 |
CN102964266A (zh) * | 2012-12-24 | 2013-03-13 | 青岛帅王油脂化学有限公司 | 一种乙撑双硬脂酰胺高收率的合成工艺 |
CN103880695A (zh) * | 2012-12-24 | 2014-06-25 | 青岛帅王油脂化学有限公司 | 一种用硬脂酸合成乙撑双硬脂酸酰胺的方法 |
CN104725261A (zh) * | 2013-12-20 | 2015-06-24 | 丰益精细化学(连云港)有限公司 | N,nˊ-烷撑双饱和脂肪酰胺及其合成方法 |
CN105348128A (zh) * | 2015-10-29 | 2016-02-24 | 安徽助成信息科技有限公司 | 一种乙撑双硬脂酸酰胺的制备方法 |
CN106008207A (zh) * | 2016-05-31 | 2016-10-12 | 邵阳学院 | 一种复合型磷钨酸盐催化合成柠檬酸酯的方法 |
CN108191814A (zh) * | 2018-01-27 | 2018-06-22 | 邵阳学院 | 一种磷钨酸钛铵复合盐催化合成环己酮乙二醇缩酮的方法 |
-
2019
- 2019-10-25 CN CN201911023252.5A patent/CN110655475B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101574667A (zh) * | 2009-06-08 | 2009-11-11 | 南京工业大学 | 一种固体酸催化剂及其制备和在酯化反应中的应用 |
CN101665447A (zh) * | 2009-09-22 | 2010-03-10 | 如皋市双马化工有限公司 | 一种硬脂酸合成乙撑硬脂酸酰胺的方法 |
CN102964266A (zh) * | 2012-12-24 | 2013-03-13 | 青岛帅王油脂化学有限公司 | 一种乙撑双硬脂酰胺高收率的合成工艺 |
CN103880695A (zh) * | 2012-12-24 | 2014-06-25 | 青岛帅王油脂化学有限公司 | 一种用硬脂酸合成乙撑双硬脂酸酰胺的方法 |
CN104725261A (zh) * | 2013-12-20 | 2015-06-24 | 丰益精细化学(连云港)有限公司 | N,nˊ-烷撑双饱和脂肪酰胺及其合成方法 |
CN105348128A (zh) * | 2015-10-29 | 2016-02-24 | 安徽助成信息科技有限公司 | 一种乙撑双硬脂酸酰胺的制备方法 |
CN106008207A (zh) * | 2016-05-31 | 2016-10-12 | 邵阳学院 | 一种复合型磷钨酸盐催化合成柠檬酸酯的方法 |
CN108191814A (zh) * | 2018-01-27 | 2018-06-22 | 邵阳学院 | 一种磷钨酸钛铵复合盐催化合成环己酮乙二醇缩酮的方法 |
Non-Patent Citations (2)
Title |
---|
XI ZHOU ETAL: "Efficient conversion of renewable levulinic acid to n-butyl levulinatecatalyzed by ammonium and silver co-doped phosphotungstic acid", 《JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL 417》 * |
王承锋等: "乙撑双硬脂酰胺的生产技术及应用分析", 《炼油与化工》 * |
Also Published As
Publication number | Publication date |
---|---|
CN110655475B (zh) | 2022-08-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4609761A (en) | Continuous preparation of linear polyethylenepolyamines using novel catalysts derived from titania and a trialkyl phosphate or phosphite | |
US4982003A (en) | Mixed oxide catalyst and process for producing an alkylenamine by using the catalyst | |
CA1143748A (en) | Methanol homologation using cobalt-ruthenium catalysts | |
US4578518A (en) | Catalytic (calcined catalyst and) preparation of linear polyethylenepolyamines (therewith) | |
US4578519A (en) | Catalytic synthesis of linear polyethylenepolyamines (polyethylenepolyamine preparation and catalyst) | |
JPS61236753A (ja) | ジエチレントリアミンの製造法 | |
CN110655475B (zh) | 一种复合掺杂杂多酸盐催化合成乙撑双硬脂酰胺的方法 | |
CN111875489B (zh) | 2-(4-戊基苯甲酰)苯甲酸和2-戊基蒽醌及其制备方法 | |
CN110668966B (zh) | 一种磷钨酸季铵钛盐催化合成乙撑双硬脂酰胺的方法 | |
CN104549295B (zh) | 烯烃异构化催化剂 | |
CN110590589A (zh) | 一种磷钨酸盐催化合成乙撑双硬脂酰胺的方法 | |
CN102464633A (zh) | (甲基)丙烯酸缩水甘油酯的合成方法 | |
CN104549351B (zh) | 异构化催化剂 | |
CN101077853A (zh) | 用固体酸催化合成双酚a的方法 | |
CN113717218A (zh) | 一种磷酸三(2-氯丙基)酯的制备方法 | |
CN108187744B (zh) | 一种磷钨酸铝铵复合盐催化合成糠醛乙二醇缩醛的方法 | |
CN115160110B (zh) | 一种合成双酚z的方法 | |
CN101190930A (zh) | 一种双核茂金属化合物及其制备以及在烯烃聚合中的应用 | |
CN112574007B (zh) | 一种新型环己亚胺类离子液体及催化柠檬酸丁酯和双酚f合成的方法 | |
CN112495391B (zh) | 一种适用于乙腈水合反应制备乙酰胺的负载型复合金属催化剂及其制备方法和应用 | |
CN115364896B (zh) | 用于合成烷基膦酸二烷基酯的催化剂及其制备方法和应用 | |
KR101093819B1 (ko) | 젖산 에스테르의 탈수 반응용 인산칼슘 촉매 및 그의 제조방법 및 이를 이용하여 젖산 에스테르로부터 아크릴계 화합물을 제조하는 방법 | |
US4007220A (en) | Preparation of phthalaldehydic acid from α,α,α,α',α'-pentachloro-o-xylene | |
CA1207744A (en) | Catalysts and preparation of linear polyethylenepolyamines therewith | |
CN105037192A (zh) | 一步法辛烷值促进剂对甲酰胺基苯烷基醚合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 422002 longxutang Shaoyang Tiantang Chemicals Co., Ltd., Shuangqing District, Shaoyang City, Hunan Province Applicant after: Hunan xiongchuangxin Material Technology Co.,Ltd. Address before: 422002 longxutang Shaoyang Tiantang Chemicals Co., Ltd., Shuangqing District, Shaoyang City, Hunan Province Applicant before: HUNAN SHAOYANG TIANTANG AUXILIARIES CHEMICAL Co.,Ltd. |
|
CB02 | Change of applicant information | ||
GR01 | Patent grant | ||
GR01 | Patent grant |