CN108640858A - A kind of 1- ethyls -3-（3- dimethylaminopropyls）The synthetic method of carbodiimides alkylsulfonate - Google Patents
A kind of 1- ethyls -3-（3- dimethylaminopropyls）The synthetic method of carbodiimides alkylsulfonate Download PDFInfo
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- -1 carbodiimides alkylsulfonate Chemical class 0.000 title claims abstract description 41
- 238000010189 synthetic method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 106
- 239000011259 mixed solution Substances 0.000 claims abstract description 55
- 239000003960 organic solvent Substances 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 34
- 238000003756 stirring Methods 0.000 claims abstract description 18
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 32
- 239000004744 fabric Substances 0.000 claims description 31
- 238000001035 drying Methods 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 16
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- DFXBWLAMLDRQPP-UHFFFAOYSA-N CCCCCCCCCCCCCCCC[S] Chemical compound CCCCCCCCCCCCCCCC[S] DFXBWLAMLDRQPP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical class CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 238000000034 method Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229920001184 polypeptide Polymers 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- INQOMBQAUSQDDS-BJUDXGSMSA-N iodomethane Chemical class I[11CH3] INQOMBQAUSQDDS-BJUDXGSMSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C267/00—Carbodiimides
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The synthetic method of one kind 1 ethyl 3 (3 dimethylaminopropyl) carbodiimides alkylsulfonate of the present invention, includes the following steps：One, 3 kilograms~4.3 kilograms of organic solvent is added in a reaction kettle, and put into 11 kilogram of ethyl 3 (3 dimethylaminopropyl) carbodiimides in organic solvent, after stirring evenly, mixed liquor is down to 15 DEG C hereinafter, obtaining mixed solution A；Two, 0.60 kilogram~2.10 kilograms alkyl sulfonic acids are added dropwise in mixed solution A, during dropwise addition, control temperature is at 0 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition organic sulfonic acid, and in reaction process, temperature control is at 25 DEG C hereinafter, obtaining mixed solution B；Three, 2.0 kilograms~3.0 kilograms of organic solvent is added in mixed solution B, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less；Four, the material that step 3 reaction generates is centrifuged and dried, 1 ethyl, 3 1.435 kilograms~2.819 kilograms of (3 dimethylaminopropyl) carbodiimides alkylsulfonate finished product is obtained.
Description
Technical field
The present invention relates to carbodiimides, and in particular to a kind of 1- ethyls -3- (3- dimethylaminopropyls) -
The synthetic method of carbodiimides alkylsulfonate.
Background technology
It is well known that 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides is condensed as a kind of efficient polypeptide
Agent, has that period of storage is short, awkward distinct disadvantage, thus exists in a manner of at salt extensively, and its esters product has
Period of storage length, convenient transportation, using simple advantage, at present apply most 1- ethyls -3- (3- dimethylaminopropyls) -
Carbodiimide hydrochloride and iodomethane salt have certain limitation in its application mode, be mainly shown as chlorion there are shadows
Ringing in certain complicated condensation reactions leads to negative reaction and substitution reaction, to influence the purity of condensation reaction, thus a kind of 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides alkylsulfonate is also widely used for polypeptide, protein, nucleotide
Dehydrating agent in synthesis realizes the polypeptide condensation reaction of complex condition.1- ethyls -3- (3- dimethylaminopropyls)-is carbonized
Diimine alkylsulfonate is water-soluble carbodiimide, the linear structure of molecule, and structural formula is as follows：
In the prior art, it there are no synthesis 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides alkylsulfonate
The document report of method.
Invention content
The present invention provides a kind of conjunctions of 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides alkylsulfonate
At method, reaction condition is mild, and production equipment is simple, and the period is short, and yield is high, it is easy to accomplish the industrial production of scale.
To achieve the above object, a kind of 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides alkyl of the invention
The synthetic method of sulfonate, includes the following steps：
3 kilograms~4.3 kilograms of organic solvent is added in a reaction kettle, and puts into 1- second in organic solvent for step 1
Mixed liquor after stirring evenly, is down to 15 DEG C hereinafter, obtaining by 1 kilogram of base -3- (3- dimethylaminopropyls)-carbodiimides
Mixed solution A.
0.60 kilogram~2.10 kilograms alkyl sulfonic acids are added dropwise in step 2 in mixed solution A, during dropwise addition, control temperature
Degree at 0 DEG C~25 DEG C, be added dropwise alkyl sulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control at 25 DEG C hereinafter,
Obtain mixed solution B；
2.0 kilograms~3.0 kilograms of organic solvent is added in step 3 in mixed solution B, keeps the temperature 2 hours, and temperature control exists
25 DEG C or less；
The material that step 3 reaction generates is centrifuged and is dried, obtains 1- ethyls -3- (3- dimethylaminos third by step 4
Base) 1.435 kilograms~2.819 kilograms of-carbodiimides alkylsulfonate finished product, yield is 88.3%~95.8%；
The chemical equation of mixed solution A dropwise addition alkyl sulfonic acid is in step 2：
Wherein：
The organic solvent select methanol, ethyl alcohol, benzene, toluene, ether, petroleum ether, dichloromethane it is one or more；
Or, the alkyl sulfonic acid in the step 2 selects methanesulfonic acid, or normal-butyl sulfonic acid is selected, or selects cetyl sulphur
Acid；
Or, in the step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and does
It is dry.
Further, in step 1,4 kilograms of benzene is added；
In step 2,0.619 kilogram of methanesulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of benzene is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.553kg, yield 95.5%.
Further, in step 1,4.3 kilograms of toluene is added；
In step 2,0.619 kilogram of methanesulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 3 kilograms of toluene is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.528kg, yield 94.4%；
Further, in step 1,4 kilograms of ether is added；
In step 2,0.63 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.544kg, yield 94.7%；
Further, in step 1,4 kilograms of ether is added；
In step 2,0.850 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of petroleum ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.772kg, yield 95.8%.
Further, in step 1,4 kilograms of ether is added；
In step 2,0.870 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of petroleum ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.754kg, yield 93.8%.
Further, in step 1,4 kilograms of methanol is added；
In step 2,1.99 kilograms of cetyl sulfonic acid are added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of methanol is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.781kg, yield 94%.
Further,
In step 1,4 kilograms of dichloromethane is added；
In step 2,2.1 kilograms of cetyl sulfonic acid are added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.890kg, yield 93.2%.
The beneficial effects of the invention are as follows：
(1) reaction process is simple, generates " 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides organic solvent " one
In place, production process can realize that zero-emission, synthesis technology are environmentally safe to step；
(2) reaction condition is mild safely, and yield is high, and solvent uses popular organic solvent, the chemicals of no hypertoxicity；
(3) feed intake and post-process simply, production cost is low, it is easy to accomplish industrialized production.
Specific implementation mode
With reference to embodiment, the present invention is further elaborated：
Embodiment 1
In step 1,3.0 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2 when temperature drops to 15 DEG C or less, start that 0.600 kilogram of methanesulfonic acid is added dropwise, during dropwise addition, control
Temperature processed at 15 DEG C~25 DEG C, be added dropwise methanesulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control 25 DEG C with
Under, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,2.0 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.435kg, yield 89.7%.
Embodiment 2
In step 1,3.8 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2, when temperature drops to 15 DEG C or less, start that 0.600 kilogram of methanesulfonic acid is added dropwise, during dropwise addition, control
Temperature processed at 15 DEG C~25 DEG C, be added dropwise methanesulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control 25 DEG C with
Under, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,2.4 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.465kg, yield 91.6%.
Embodiment 3
4.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 when temperature drops to 15 DEG C or less starts that 0.619 kilogram of methanesulfonic acid is added dropwise, during dropwise addition, control
Temperature at 15 DEG C~25 DEG C, be added dropwise methanesulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control at 25 DEG C hereinafter,
The chemical equation of mixed solution A dropwise addition alkyl sulfonic acid is in step 2：
。
2.8 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.553kg, yield 95.5%.
Embodiment 4
In step 1,4.0 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2, when temperature drops to 15 DEG C or less, start that 0.630 methanesulfonic acid is added dropwise, during dropwise addition, control temperature
Degree is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition methanesulfonic acid, and in reaction process, temperature control is at 25 DEG C hereinafter, step
The chemical equation of mixed solution A dropwise addition alkyl sulfonic acid is in rapid two：
。
In step 3,2.8 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.544kg, yield 94.7%.
Embodiment 5
In step 1,4.3 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2, when temperature drops to 15 DEG C or less, start that 0.619 kilogram of methanesulfonic acid is added dropwise, during dropwise addition, control
Temperature processed at 15 DEG C~25 DEG C, be added dropwise methanesulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control 25 DEG C with
Under, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,3.0 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.528kg, yield 94.4%.
Embodiment 6
In step 1,3.0 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2, when temperature drops to 15 DEG C or less, starts that 0.840 kilogram of normal-butyl sulfonic acid is added dropwise, process is added dropwise
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition normal-butyl sulfonic acid, in reaction process, temperature control
At 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,2.0 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1-
Ethyl -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.625kg, yield 88.3%.
Embodiment 7
In step 1,3.8 kilograms of organic solvent is added in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
In step 2, when temperature drops to 15 DEG C or less, starts that 0.840 kilogram of normal-butyl sulfonic acid is added dropwise, process is added dropwise
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition normal-butyl sulfonic acid, in reaction process, temperature control
At 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,2.4 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
In step 4, after the material that generation is reacted in step 3 is packed into cloth bag, it is put into centrifuge and drying, is obtained
1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.678kg, yield 91.2%.
Embodiment 8
4.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 when temperature drops to 15 DEG C or less starts that 0.850 kilogram of normal-butyl sulfonic acid is added dropwise, during dropwise addition,
Temperature is controlled at 15 DEG C~25 DEG C, the reaction was continued 1 hour after dropwise addition normal-butyl sulfonic acid, and in reaction process, temperature control exists
25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
2.8 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.772kg, yield 95.8%.
Embodiment 9
4.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 when temperature drops to 15 DEG C or less starts that 0.870 kilogram of normal-butyl sulfonic acid is added dropwise, during dropwise addition,
Temperature is controlled at 15 DEG C~25 DEG C, the reaction was continued 1 hour after dropwise addition normal-butyl sulfonic acid, and in reaction process, temperature control exists
25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
In step 3,2.8 kilograms of organic solvent is added after reaction, keeps the temperature 2 hours, temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.754kg, yield 93.8%.
Embodiment 10
4.3 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 when temperature drops to 15 DEG C or less starts that 0.850 kilogram of normal-butyl sulfonic acid is added dropwise, during dropwise addition,
Temperature is controlled at 15 DEG C~25 DEG C, the reaction was continued 1 hour after dropwise addition normal-butyl sulfonic acid, and in reaction process, temperature control exists
25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
3.0 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.724kg, yield 93.2%.
Embodiment 11
3.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 starts that 1.97 kilograms of cetyl sulfonic acid are added dropwise, process is added dropwise when temperature drops to 15 DEG C or less
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition cetyl sulfonic acid, in reaction process, temperature control
It makes at 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
2.0 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.650kg, yield 89.2%.
Embodiment 12
3.8 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 starts that 1.970 kilograms of cetyl sulfonic acid are added dropwise, process is added dropwise when temperature drops to 15 DEG C or less
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition cetyl sulfonic acid, in reaction process, temperature control
It makes at 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
2.4 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonic acid finished product 2.702kg, yield 91.0%.
Embodiment 13
4.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 starts that 1.990 kilograms of cetyl sulfonic acid are added dropwise, process is added dropwise when temperature drops to 15 DEG C or less
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition cetyl sulfonic acid, in reaction process, temperature control
It makes at 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
2.8 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.810kg, yield 94.0%.
Embodiment 14
4.0 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 starts that 2.10 kilograms of cetyl sulfonic acid are added dropwise, process is added dropwise when temperature drops to 15 DEG C or less
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition cetyl sulfonic acid, in reaction process, temperature control
It makes at 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
2.8 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.890kg, yield 93.2%.
Embodiment 15
4.3 kilograms of organic solvent is added in step 1 in a reaction kettle, puts into 1- ethyls -3- (3- dimethylaminos third
Base) 1.0 kilograms of-carbodiimides, start stirring, is passed through chilled brine, starts to cool down.
Step 2 starts that 1.990 kilograms of cetyl sulfonic acid are added dropwise, process is added dropwise when temperature drops to 15 DEG C or less
In, control temperature is at 15 DEG C~25 DEG C, and the reaction was continued 1 hour after dropwise addition cetyl sulfonic acid, in reaction process, temperature control
It makes at 25 DEG C hereinafter, the chemical equation that alkyl sulfonic acid is added dropwise in mixed solution A in step 2 is：
。
3.0 kilograms of organic solvent is added in step 3 after reaction, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C or less.
Step 4 is put into centrifuge and drying, obtains 1- second after the material that step 3 reaction generates is packed into cloth bag
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.763kg, yield 92.4%.
Finally it should be noted that listed above is only specific embodiments of the present invention.It is clear that the invention is not restricted to
Above example can also have many variations.Those skilled in the art can directly lead from present disclosure
All deformations for going out or associating, are considered as protection scope of the present invention.
Claims (9)
1. a kind of synthetic method of 1- ethyls -3- (3- dimethylaminopropyls)-carbodiimides alkylsulfonate, including it is following
Step：
3 kilograms~4.3 kilograms of organic solvent, and input 1- ethyls -3- in organic solvent is added in step 1 in a reaction kettle
Mixed liquor after stirring evenly, is down to 15 DEG C hereinafter, obtaining mixing molten by 1 kilogram of (3- dimethylaminopropyls)-carbodiimides
Liquid A.
0.60 kilogram~2.10 kilograms alkyl sulfonic acids are added dropwise in step 2 in mixed solution A, and during dropwise addition, control temperature is 0
DEG C~25 DEG C, be added dropwise organic sulfonic acid after the reaction was continued 1 hour, in reaction process, temperature control at 25 DEG C hereinafter, must mix
Solution B；
2.0 kilograms~3.0 kilograms of organic solvent is added in step 3 in mixed solution B, keeps the temperature 2 hours, and temperature is controlled at 25 DEG C
Below；
The material that step 3 reaction generates is centrifuged and is dried, obtains 1- ethyls -3- (3- dimethylaminopropyls)-by step 4
1.435 kilograms~2.819 kilograms of carbodiimides alkylsulfonate finished product, yield are 88.3%~95.8%；
The chemical equation of mixed solution A dropwise addition alkyl sulfonic acid is in step 2：
2. synthetic method as described in claim 1, it is characterised in that：The organic solvent select methanol, ethyl alcohol, benzene, toluene,
Ether, petroleum ether, dichloromethane it is one or more；
Or, the alkyl sulfonic acid in the step 2 selects methanesulfonic acid；Or, selecting normal-butyl sulfonic acid；Or, selecting cetyl sulphur
Acid；
Or, in the step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying.
3. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of benzene is added；
In step 2,0.619 kilogram of methanesulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of benzene is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.553kg, yield 95.5%.
4. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4.3 kilograms of toluene is added；
In step 2,0.619 kilogram of methanesulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 3 kilograms of toluene is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides mesylate finished product 1.528kg, yield 94.4%.
5. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of ether is added；
In step 2,0.63 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.544kg, yield 94.7%.
6. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of ether is added；
In step 2,0.850 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of petroleum ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.772kg, yield 95.8%.
7. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of ether is added；
In step 2,0.870 kilogram of normal-butyl sulfonic acid is added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of petroleum ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides normal-butyl sulfonate finished product 1.754kg, yield 93.8%.
8. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of methanol is added；
In step 2,1.99 kilograms of cetyl sulfonic acid are added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of methanol is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.781kg, yield 94%.
9. synthetic method as claimed in claim 1 or 2, it is characterised in that：
In step 1,4 kilograms of dichloromethane is added；
In step 2,2.1 kilograms of cetyl sulfonic acid are added dropwise in mixed solution A；
In step 3, in mixed solution B, 2.8 kilograms of ether is added and is reacted；
In step 4, after the material that step 3 reaction generates is packed into cloth bag, it is put into centrifuge and drying, obtains 1- second
Base -3- (3- dimethylaminopropyls)-carbodiimides cetyl sulfonate finished product 2.890kg, yield 93.2%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5029519A (en) * | 1973-07-14 | 1975-03-25 | ||
| WO2014083427A2 (en) * | 2012-11-30 | 2014-06-05 | Siemens Healthcare Diagnostics Inc. | Compositions and methods for detecting vitamin d |
-
2018
- 2018-06-11 CN CN201810592643.8A patent/CN108640858A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5029519A (en) * | 1973-07-14 | 1975-03-25 | ||
| WO2014083427A2 (en) * | 2012-11-30 | 2014-06-05 | Siemens Healthcare Diagnostics Inc. | Compositions and methods for detecting vitamin d |
Non-Patent Citations (1)
| Title |
|---|
| RALPH J. STEVENSON ET AL.: "Nitro seco Analogues of the Duocarmycins Containing Sulfonate Leaving Groups as Hypoxia-Activated Prodrugs for Cancer Therapy", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
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