CN115477596A - Sulfuric acid ester compound and preparation method thereof - Google Patents
Sulfuric acid ester compound and preparation method thereof Download PDFInfo
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- CN115477596A CN115477596A CN202211151841.3A CN202211151841A CN115477596A CN 115477596 A CN115477596 A CN 115477596A CN 202211151841 A CN202211151841 A CN 202211151841A CN 115477596 A CN115477596 A CN 115477596A
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 40
- -1 Sulfuric acid ester compound Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 238000003756 stirring Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 description 5
- HBRLMDFVVMYNFH-UHFFFAOYSA-N 1-ethoxy-1,1,2,2-tetrafluoroethane Chemical compound CCOC(F)(F)C(F)F HBRLMDFVVMYNFH-UHFFFAOYSA-N 0.000 description 3
- 229910000975 Carbon steel Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000010962 carbon steel Substances 0.000 description 3
- MPUOMQIWMPWPBB-UHFFFAOYSA-N 4-chloro-2-(4-chloro-1,1,1,3,3-pentafluorobutan-2-yl)oxy-1,1,1,3,3-pentafluorobutane Chemical compound ClCC(F)(F)C(C(F)(F)F)OC(C(F)(F)F)C(CCl)(F)F MPUOMQIWMPWPBB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- YQQHEHMVPLLOKE-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-methoxyethane Chemical compound COC(F)(F)C(F)F YQQHEHMVPLLOKE-UHFFFAOYSA-N 0.000 description 1
- MAQRTHXLIHZJNT-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-chloroacetate Chemical compound FC(F)(F)COC(=O)CCl MAQRTHXLIHZJNT-UHFFFAOYSA-N 0.000 description 1
- AQKCWZOXYGNDRI-UHFFFAOYSA-N 2-chloro-1,1-difluoro-1-methoxyethane Chemical compound COC(F)(F)CCl AQKCWZOXYGNDRI-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
技术领域technical field
本发明涉及有机合成技术领域，具体是一种硫酸酯类化合物及其制备方法。The invention relates to the technical field of organic synthesis, in particular to a sulfuric acid ester compound and a preparation method thereof.
背景技术Background technique
氢氟醚的GWP低，ODP为零，且大气停留时间很短，被认为是现有HFCs型制冷剂的替代品之一。除此之外，氢氟醚还被用作麻醉剂、清洗剂等，在进行氢氟醚的合成研究过程中，将氢氟醚与浓硫酸混合后，我们意外的制得了一种稳定的新的化合物，并最终确定了其结构形式。Hydrofluoroether has low GWP, zero ODP, and short atmospheric residence time, and is considered to be one of the substitutes for existing HFCs refrigerants. In addition, hydrofluoroether is also used as an anesthetic, cleaning agent, etc. During the research on the synthesis of hydrofluoroether, after mixing hydrofluoroether with concentrated sulfuric acid, we unexpectedly prepared a stable new compound, and finally determined its structural form.
现有技术中公开的醚与硫酸反应制得硫酸酯类化合物的过程中均未公开上述新的化合物，具体如下：The above-mentioned new compounds are not disclosed in the process of preparing sulfuric acid ester compounds from the reaction of ether and sulfuric acid disclosed in the prior art, as follows:
专利CN2014107151695中公开的是一种4,4-二氟乙酰乙酸烷基酯的制备方法，其具体公开了“在反应装置中加入硫酸，然后依次加入水和1,1,2,2-四氟乙基乙基醚，进行水解反应，分离得到二氟乙酸乙酯和氟化氢”。此专利中制备二氟乙酸乙酯的方法是在酸性条件下进行的水解反应，硫酸作为催化剂使用，这与本发明的制备方法中硫酸作为反应物使用是完全不同的。Patent CN2014107151695 discloses a preparation method of
而《有机氟化工》2017年第4期的《四氟乙烯合成二氟乙酸乙酯的研究》文章中指出硫酸若要参与反应，其浓度必须是90％以上，综合上述分析可以进一步合理的推出该专利中的硫酸仅仅是作为催化剂而不是反应物，其反应过程中并不会形成本申请中所要保护的化合物。However, in the article "Research on the Synthesis of Ethyl Difluoroacetate from Tetrafluoroethylene" in the 4th issue of 2017 in "Organic Fluorine Chemical Industry", it is pointed out that if sulfuric acid is to participate in the reaction, its concentration must be above 90%. Based on the above analysis, it can be further reasonably introduced The sulfuric acid in this patent is only used as a catalyst rather than a reactant, and the compound to be protected in this application will not be formed during the reaction.
在《有机氟工业》2017年第1期的《二氟乙酸乙酯的合成研究》的二氟乙酸乙酯的制备内容里，根据其记载的内容可以得知，该文章中浓硫酸的作用是催化剂，根据其反应机理推断，也没有生成本申请中所要求保护的化合物。According to the content of the preparation of ethyl difluoroacetate in the "Research on the Synthesis of Ethyl Difluoroacetate" in the first issue of "Organic Fluorine Industry" in 2017, it can be known from the content of the record that the role of concentrated sulfuric acid in this article is The catalyst, deduced according to its reaction mechanism, did not generate the compound claimed in this application.
基于此，本发明中对此类硫酸酯类化合物及其制备方法展开了研究。Based on this, research has been carried out on such sulfuric acid ester compounds and preparation methods thereof in the present invention.
发明内容Contents of the invention
本发明的目的是：提供一种硫酸酯类化合物及其制备方法，用于填补行业内的空白。The purpose of the present invention is: provide a kind of sulfuric acid ester compound and preparation method thereof, be used for filling up the blank in the industry.
为实现上述目的，本发明采用的技术方案如下：To achieve the above object, the technical scheme adopted in the present invention is as follows:
一种硫酸酯类化合物，所述化合物的结构如式I所示，A kind of sulfuric acid ester compound, the structure of described compound is shown in formula I,
其中：R1、R2、R3、R6、R7、R8选用H、F、Cl、C1～C3的直链或支链烷基、卤素取代的C1～C3的直链或支链烷基中的一种。Among them: R1, R2, R3, R6, R7, R8 select one of H, F, Cl, C1~C3 straight chain or branched chain alkyl, halogen substituted C1~C3 straight chain or branched chain alkyl .
一种硫酸酯类化合物的制备方法，其反应式如下：A kind of preparation method of sulfuric acid ester compound, its reaction formula is as follows:
反应釜中加入式Ⅱ所示醚类化合物，在一定的温度下，滴加浓硫酸，加完继续反应至反应结束，得到式I所示化合物；Add the ether compound shown in formula II to the reaction kettle, add concentrated sulfuric acid dropwise at a certain temperature, continue the reaction until the reaction is completed, and obtain the compound shown in formula I;
其中：式Ⅱ中的R4/R5选用F或Cl，式I和式Ⅱ中的R1、R2、R3、R6、R7、R8选用H、F、Cl、C1～C3的直链或支链烷基、卤素取代的C1～C3的直链或支链烷基中的一种。Among them: R4/R5 in formula II is selected from F or Cl, R1, R2, R3, R6, R7, R8 in formula I and formula II are selected from H, F, Cl, C1 ~ C3 straight chain or branched chain alkyl , One of C1-C3 straight-chain or branched-chain alkyl groups substituted with halogen.
进一步的，所述式Ⅱ化合物包括以下化合物：
进一步的，所述反应温度为10～100℃，浓硫酸的浓度为90～99％。Further, the reaction temperature is 10-100° C., and the concentration of concentrated sulfuric acid is 90-99%.
进一步的，反应温度为20～60℃，浓硫酸的浓度为90～96％。Further, the reaction temperature is 20-60° C., and the concentration of concentrated sulfuric acid is 90-96%.
进一步的，搅拌速度为150-180转/分钟。Further, the stirring speed is 150-180 rpm.
进一步的，所述式Ⅱ所示的醚类化合物和95％浓硫酸的摩尔配比为1:1～2。Further, the molar ratio of the ether compound represented by the formula II to 95% concentrated sulfuric acid is 1:1-2.
进一步的，所述式Ⅱ所示的醚类化合物和95％浓硫酸的摩尔配比为1:1.5。Further, the molar ratio of the ether compound represented by the formula II to 95% concentrated sulfuric acid is 1:1.5.
采用本发明的技术方案的有益效果是：The beneficial effects of adopting the technical solution of the present invention are:
本发明所涉及的反应不需要添加催化剂，反应条件温和，设备简单，且由于反应为常压反应，可以随时监测反应情况，本发明中采用气相色谱仪分析原料含量是不是反应完全，没反应完全的可以延长反应时间或者补加浓硫酸，这样可以使得反应可以一次性反应完全，避免二次回收处理，显著降低了原料的损耗，此外，反应过程中产生的尾气可以用水吸收，避免造成环境污染。The reaction involved in the present invention does not need to add a catalyst, the reaction conditions are mild, the equipment is simple, and because the reaction is a normal pressure reaction, the reaction situation can be monitored at any time. In the present invention, a gas chromatograph is used to analyze whether the raw material content is completely reacted or not. The reaction time can be extended or concentrated sulfuric acid can be added, so that the reaction can be completed at one time, avoiding secondary recycling treatment, and significantly reducing the loss of raw materials. In addition, the tail gas generated during the reaction can be absorbed by water to avoid environmental pollution. .
此外，本申请中的化合物性质稳定易储存，所以便于作为制备其他诸多化合物的中间体。In addition, the compounds in this application are stable and easy to store, so they are convenient to be used as intermediates for the preparation of many other compounds.
附图说明Description of drawings
图1为本发明中制得的2-氯-(1,1-二硫酸酯)乙基-2,2,2-三氟乙基醚化合物质谱图。Figure 1 is the mass spectrum of 2-chloro-(1,1-disulfate)ethyl-2,2,2-trifluoroethyl ether compound prepared in the present invention.
图2为实施例1中制得的2-氯-(1,1-二硫酸酯)乙基-2,2,2-三氟乙基醚化合物气相色谱图。FIG. 2 is a gas chromatogram of 2-chloro-(1,1-disulfate)ethyl-2,2,2-trifluoroethyl ether compound prepared in Example 1.
具体实施方式detailed description
下面将结合本发明具体实施例对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the specific embodiments of the present invention. Obviously, the described embodiments are only some of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.
本发明中的原料均为普通市售。The raw materials in the present invention are generally commercially available.
1,1,2,2-四氟乙基甲基醚99％、1,1,2,2-四氟乙基乙基醚99％、1,1,2,2-四氟乙基-1,2,2-乙基醚99％(山东华氟化工有限责任公司)1,1,2,2-tetrafluoroethyl methyl ether 99%, 1,1,2,2-tetrafluoroethyl ethyl ether 99%, 1,1,2,2-tetrafluoroethyl-1 ,2,2-Ethyl ether 99% (Shandong Huafu Chemical Co., Ltd.)
2-氯-1,1-二氟乙基甲基醚99％、2-氯-1,1-二氟乙基乙基醚99％、2-氯-1,1-二氟乙基-2,2,2-三氟乙基醚99％(江苏蓝色星球环保科技股份有限公司)2-chloro-1,1-difluoroethyl methyl ether 99%, 2-chloro-1,1-difluoroethyl ethyl ether 99%, 2-chloro-1,1-difluoroethyl-2 ,2,2-Trifluoroethyl ether 99% (Jiangsu Blue Planet Environmental Protection Technology Co., Ltd.)
图1为本发明中制得的2-氯-(1,1-二硫酸酯)乙基-2,2,2-三氟乙基醚化合物质谱图。Figure 1 is the mass spectrum of 2-chloro-(1,1-disulfate)ethyl-2,2,2-trifluoroethyl ether compound prepared in the present invention.
图2为实施例1中制得的2-氯-(1,1-二硫酸酯)乙基-2,2,2-三氟乙基醚化合物气相色谱图。FIG. 2 is a gas chromatogram of 2-chloro-(1,1-disulfate)ethyl-2,2,2-trifluoroethyl ether compound prepared in Example 1.
实施例1Example 1
将199克2-氯-1,1-二氟乙基-2,2,2-三氟乙基醚加入1升的碳钢搅拌反应釜中，在搅拌的状态下滴加155克95％浓度的浓硫酸，控制反应温度在60℃以下，滴加结束后，维持温度在30℃左右搅拌反应4小时得到硫酸酯产物，收率99％。反应过程中，尾气用水吸收。Add 199 grams of 2-chloro-1,1-difluoroethyl-2,2,2-trifluoroethyl ether into a 1-liter carbon steel stirred reactor, and add 155 grams of 95% concentration dropwise under stirring concentrated sulfuric acid, control the reaction temperature below 60°C, after the dropwise addition, keep the temperature at about 30°C and stir for 4 hours to obtain the sulfuric acid ester product with a yield of 99%. During the reaction, the tail gas is absorbed with water.
实施例2Example 2
将238克1,1,2,2-四氟乙基乙基醚加入1升的碳钢搅拌反应釜中，在搅拌的状态下滴加248克95％浓度的浓硫酸，控制反应温度在40℃以下，滴加结束后，维持温度在30℃左右搅拌反应2小时得到硫酸酯产物，收率98％。反应过程中，尾气用水吸收。Add 238 grams of 1,1,2,2-tetrafluoroethyl ethyl ether into a 1-liter carbon steel stirred reactor, add 248 grams of 95% concentrated sulfuric acid dropwise under stirring, and control the reaction temperature at 40 °C, after the dropwise addition, maintain the temperature at about 30 °C and stir the reaction for 2 hours to obtain the sulfuric acid ester product with a yield of 98%. During the reaction, the tail gas is absorbed with water.
实施例3Example 3
将211克2-氯-1,1-二氟乙基苯乙基醚加入1升的碳钢搅拌反应釜中，在搅拌的状态下滴加155克95％浓度的浓硫酸，控制反应温度在60℃以下，滴加结束后，维持温度在30℃左右搅拌反应4小时得到硫酸酯产物，收率98％。反应过程中，尾气用水吸收。Add 211 grams of 2-chloro-1,1-difluoroethyl phenethyl ether into a 1-liter carbon steel stirred reactor, add 155 grams of 95% concentrated sulfuric acid dropwise under stirring, and control the reaction temperature at
实施例4Example 4
在5升带搅拌的内衬四氟塑料的搅拌釜中加入3500克水，在搅拌状态下于1小时内滴加3580克例一反应中制得的硫酸酯，反应釜温度控制在30℃以下，滴加结束后静置分层，分出下层有机物得到1589克氯乙酸-2,2,2-三氟乙酯，收率90％。Add 3,500 grams of water in a 5-liter stirred tank lined with PTFE, and add 3,580 grams of sulfuric acid ester dropwise within 1 hour under stirring, and the temperature of the reactor is controlled below 30°C. , after the dropwise addition, the mixture was left to stand and separated, and the organic matter in the lower layer was separated to obtain 1589 g of 2,2,2-trifluoroethyl chloroacetate, with a yield of 90%.
此外，应当理解，虽然本说明书按照实施方式加以描述，但并非每个实施方式仅包含一个独立的权利方案，说明书的这种叙述方式仅仅是为清楚起见，本领域技术人员应当将说明书作为一个整体，各实施例中的技术方案也可以经适当组合，形成本领域技术人员可以理解的其他实施方式。In addition, it should be understood that although this specification is described according to implementation modes, not every implementation mode includes only one independent claim. , the technical solutions in the various embodiments can also be properly combined to form other implementations that can be understood by those skilled in the art.
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| JP2008169162A (en) * | 2007-01-12 | 2008-07-24 | Sumitomo Seika Chem Co Ltd | Method for producing methylene disulfonate compound |
| CN104447328A (en) * | 2014-12-01 | 2015-03-25 | 金凯(辽宁)化工有限公司 | Method for preparing alkyl 4,4-difluoroacetylacetate |
| CN113164864A (en) * | 2018-12-06 | 2021-07-23 | 格里洛工厂股份有限公司 | Process for recycling or disposing of halogenated hydrocarbons |
| CN114085151A (en) * | 2021-12-08 | 2022-02-25 | 四川福思达生物技术开发有限责任公司 | Preparation method of high-purity ethyl difluoroacetate |
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