<!--

       Copyright 2011 Peter Murray-Rust et. al.

       Licensed under the Apache License, Version 2.0 (the "License");
       you may not use this file except in compliance with the License.
       You may obtain a copy of the License at

           http://www.apache.org/licenses/LICENSE-2.0

       Unless required by applicable law or agreed to in writing, software
       distributed under the License is distributed on an "AS IS" BASIS,
       WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
       See the License for the specific language governing permissions and
       limitations under the License.

-->

<cml xmlns="http://www.xml-cml.org/schema">
  <moleculeList>
    <molecule id="m1" title="Monomethoxy poly(ethylene glycol), MW = 5000, ex Aldrich">
      <property dictRef="cml:molarMass">
        <scalar dataType="xsd:double" units="units:g.mol-1">5000</scalar>
      </property>
    </molecule>
    <molecule id="m2" title="triethylamine">
      <formula concise="C 6 H 15 N 1"/>
      <property name="density">
        <scalar dataType="xsd:float" dictRef="cml:density" units="units:g.cm-3">0.728</scalar>
      </property>
    </molecule>
    <molecule id="m3" title="Polymer-bound 4-(dimethylamino)pyridine">
      <formula concise="C 6 H 10 N 2"/>
    </molecule>
    <molecule id="m4" title="2-Bromoisobutyryl bromide">
      <formula concise="C 4 H 6 Br 2 O 1"/>
      <property name="density">
        <scalar dataType="xsd:float" dictRef="cml:density" units="units:g.cm-3">1.40</scalar>
      </property>
    </molecule>
    <molecule id="2a" title="poly(ethylene glycol) (PEG) macroinitiator">
    </molecule>
  </moleculeList>

  <reactionScheme title="Preparation of poly(ethylene glycol) (PEG) macroinitiator " id="ex2">
    <reaction title="Synthesis of 2a">
      <reactantList>
        <reactant id="r1">
          <molecule ref="m1"/>
          <amount id="a1" units="units:g" unitType="unitType:mass">50</amount>
          <amount id="a1m" units="units:mmol">0.01</amount>
        </reactant>
        <reactant id="r2" count="1" title="ET3N">
          <molecule ref="m2"/>
          <amount id="a2" units="units:g">2.025</amount>
          <amount id="a2m" units="units:mmol">0.02</amount>
        </reactant>
        <reactant id="r3" count="1">
          <molecule ref="m3"/>
          <amount id="a3" units="units:ml">2.0</amount>
          <amount id="a3m" units="units:mmol/g">1.25</amount>
        </reactant>
      </reactantList>
      
      <substanceList>
        <substance id="ss1" count="2" role="cml:Solvent">
          <molecule id="s1" ref="toluene">
          </molecule>
          <amount id="a4" units="units:ml">250</amount>
        </substance>
      </substanceList>
      
      <productList>
        <product id="p1" color="white" state="solid">
          <molecule ref="2a"/>
          <amount id="a5" units="units:g">0.52</amount>
          <amount id="a6" units="units:percent">41</amount>
        </product>
      </productList>
    </reaction>
  </reactionScheme>
    
  <actionList title="Preparation of poly(ethylene glycol) (PEG) macroinitiator ">
    <action role="reaction">
      <object id="o1" type="apparatus">2-necked round bottom flask + suba seal + CaCl2 guard tube</object>
      <object id="o1" type="apparatus">magnetic stirrer</object>
      <reaction ref="r1"/>
      <conditionList>
      <scalar id="sc5" dictRef="cml:temp" units="units:celsius">21</scalar>
      <scalar id="sc6" dictRef="cml:time">overnight</scalar>
      </conditionList>
    </action>
    
    <action role="reactionContinuation">
      <conditionList>
        <scalar id="sc5" dictRef="cml:temp" units="units:celsius">21</scalar>
        <scalar id="sc6" dictRef="cml:time">overnight</scalar>
      </conditionList>
    </action>
  
    <actionList role="workup">
      <action role="filtration"/>
      <action role="solventEvaporation"/>
      <action role="redissolve">
        <substance id="ss2" role="cml:solvent">
          <molecule id="m5" ref="CH2CL2"/>
        </substance>
      </action>
      
      <action role="neutralize">
        <substance id="ss3" role="cml:base">
          <molecule id="m6" ref="NA2CO3"/>
        </substance>
      </action>
      
      <action role="dry">
        <substance id="ss4" role="cml:drier">
          <molecule id="m7" ref="NA2SO4"/>
        </substance>
      </action>
      
      <action role="purification">
        <substanceList role="cml:solvent">
          <substance id="ss5">
            <molecule id="m8" ref="hexane"/>
            <amount id="a5" unitType="unitType:vol">8</amount>
          </substance>
          <substance id="ss6">
            <molecule id="m9" ref="ethyl"/>
            <amount id="a6" unitType="unitType:vol">2</amount>
          </substance>
        </substanceList>
      </action>
      
    </actionList>
    
  </actionList>
  
</cml>
