CSS ONLY Animate Draw Circle with border-radius and transparent background

Solution 1:

This is my solution.

I set a background on body to show it is transparent

body {
  background: repeating-linear-gradient(45deg, white 0px, lightblue 100px);
  height: 500px;
  background-size: 500px 500px;
  background-repeat: no-repeat;
}

html {
  height: 100%;
}

#container {
  position: absolute;
  width: 400px;
  height: 400px;
   border: solid red 1px;
   animation: colors 4s infinite;
}

#halfclip {
  width: 50%;
  height: 100%;
  right: 0px;
  position: absolute;
   overflow: hidden;
   transform-origin: left center;
   animation: cliprotate 16s steps(2) infinite;
   -webkit-animation: cliprotate 16s steps(2) infinite;
}

.halfcircle {
  box-sizing: border-box;
  height: 100%;
  right: 0px;
  position: absolute;
  border: solid 25px transparent;
   border-top-color: blue;
   border-left-color: blue;
   border-radius: 50%;
}
#clipped {
  width: 200%;
   animation: rotate 8s linear infinite;
   -webkit-animation: rotate 8s linear infinite;
}
#fixed {
  width: 100%;
    transform: rotate(135deg);  
   animation: showfixed 16s steps(2) infinite;
   -webkit-animation: showfixed 16s linear infinite;
}

@-webkit-keyframes cliprotate {
  0% {transform: rotate(0deg);}
  100% {transform: rotate(360deg);}
}

@keyframes cliprotate {
  0% {transform: rotate(0deg);}
  100% {transform: rotate(360deg);}
}


@-webkit-keyframes rotate {
  0% {transform: rotate(-45deg);}
  100% {transform: rotate(135deg);}
}

@keyframes rotate {
  0% {transform: rotate(-45deg);}
  100% {transform: rotate(135deg);}
}

@-webkit-keyframes showfixed {
  0% {opacity: 0;}
  49.9% {opacity: 0;}
  50% {opacity: 1;}
 100% {opacity: 1;}
}
<div id="container">
    <div id="halfclip">
        <div class="halfcircle" id="clipped">
        </div>
    </div>
    <div class="halfcircle" id="fixed">
    </div>
</div>

And this is a variation on the solution, to make it run only once on hover

body {
  background: repeating-linear-gradient(45deg, white 0px, lightblue 100px);
  height: 500px;
  background-size: 500px 500px;
  background-repeat: no-repeat;
}

html {
  height: 100%;
}

#container {
  position: absolute;
  width: 300px;
  height: 300px;
   border: solid red 1px;
}

#halfclip {
    width: 50%;
    height: 100%;
    right: 0px;
    position: absolute;
    overflow: hidden;
    transform-origin: left center;
}

#container:hover #halfclip {
    animation: cliprotate 6s 1;
    transform: rotate(180deg);
} 

@keyframes cliprotate {
  0% {transform: rotate(0deg);}
  50% {transform: rotate(0deg);}
  50.01% {transform: rotate(180deg);}
  100% {transform: rotate(180deg);}
}

.halfcircle {
  box-sizing: border-box;
  height: 100%;
  right: 0px;
  position: absolute;
  border: solid 25px transparent;
   border-top-color: blue;
   border-left-color: blue;
   border-radius: 50%;
}

#clipped {
    width: 200%;
    transform: rotate(-45deg);
}
#container:hover #clipped {
    transform: rotate(135deg);
    animation: rotate 3s linear 2;
}


@keyframes rotate {
  0% {transform: rotate(-45deg);}
  100% {transform: rotate(135deg);}
}


#fixed {
  width: 100%;
    transform: rotate(135deg);  
    opacity: 0;
}

#container:hover #fixed {
    opacity: 1;
    animation: showfixed 6s 1;
}



@keyframes showfixed {
  0% {opacity: 0;}
  49.99% {opacity: 0;}
  50% {opacity: 1;}
 100% {opacity: 1;}
}
<div id="container">
    <div id="halfclip">
        <div class="halfcircle" id="clipped">
        </div>
    </div>
    <div class="halfcircle" id="fixed">
    </div>
</div>